Organic compound and application thereof
1. An organic compound having a structure represented by formula (1):
wherein:
D1and D2Each independently selected from NR5、NR6One of O or S;
W1and W2Each independently is C, CH or CR7；
Ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from an aromatic ring of C6-C60 or a heteroaromatic ring of C3-C60;
ring Ar3And R6Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
ring Ar4And ring R5Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
R6and W2Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
R5and W1Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
R1、R2、R3and R4Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aryloxy60 of arylboron, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
n1, n2, n3 and n4 are each independently selected from integers of 0 to 10;
when n1 is an integer greater than 1, multiple R1Are the same or different, and a plurality of R1Can be connected into a ring;
when n2 is an integer greater than 1, multiple R2Are the same or different, and a plurality of R2Can be connected into a ring;
when n3 is an integer greater than 1, multiple R3Are the same or different, and a plurality of R3Can be connected into a ring;
when n4 is an integer greater than 1, multiple R4Are the same or different, and a plurality of R4Can be connected into a ring;
R5and R6Each independently selected from one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
R7one selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
R8、R9and R10Each independently selected from substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 aryl amino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 cyclic aliphatic chain hydrocarbon amino30 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
when R is as defined above1、R2、R3、R4、R5、R6、R7、R8、R9And R10When the above substituents independently exist, the substituents independently exist, and are selected from one or a combination of two of halogen, cyano, chain alkyl of C1-C20, cycloalkyl of C3-C20, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryloxy of C6-C30, aryl of C6-C30, substituted or unsubstituted arylboron of C6-C60, and heteroaryl of C3-C30.
2. The organic compound of claim 1, the n1, n2, n3, and n4 are each independently selected from an integer of 1-5;
the R is5And R6Each independently selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; preferably, said R is5And R6Each independently selected from any one of substituted or unsubstituted benzene ring, naphthalene ring and anthracene ring; most preferably, said R5And R6Each independently is a substituted or unsubstituted benzene ring;
the R is7One selected from deuterium, halogen, cyano, chain alkyl of C1-C6, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; preferably, said R is7One selected from deuterium, halogen, cyano, substituted or unsubstituted benzene ring;
the R is8、R9And R10Each independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl.
3. The organic compound according to claim 1, wherein in formula (1)D is1Is NR5，D2Is NR6And R is5And R6The same or different; preferably, R5And R6The same is true.
4. The organic compound according to claim 1, having a structure represented by any one of the following structural formulae (1-1), (1-2) or (1-3):
wherein, W1、W2、R1-R6、Ar1-Ar4And n1-n4 are each as defined in formula (1).
5. The organic compound according to claim 1, having a structure represented by any one of the following structural formulae (1-4), (1-5) or (1-6):
wherein R is1-R4、Ar1-Ar4And n1-n4 are each as defined in formula (1).
6. The organic compound according to any one of claims 1 to 5, the ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from an aromatic ring of C6-C60 or a heteroaromatic ring of C3-C30;
preferably, ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from an aromatic ring of C6-C30 or a heteroaromatic ring of C3-C20;
more preferably, ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from any one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan or thiophene;
most preferably, the ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently a benzene ring.
7. The organic compound according to any one of claims 1 to 5, wherein R is1、R2、R3And R4Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluorescent anthracyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, spirodicloro-yl, dihydrophenanthryl, anthryl, and spiromesic-or trans-indenofluorenyl, Isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalyl, 1, 3-thiazolyl, pyrrolyl, isoindolyl, indazolyl, quinoxalinyl, phenanthrolinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 15-diazanthryl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, one of 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, diphenylboryl, dimyridylbinyl, dipentafluorophenylboryl, bis (2,4, 6-triisopropylphenyl) boryl, or a combination selected from two of the foregoing groups;
said R5And R6Each independently selected from the following substituents: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridecyl, spiroisotridecyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, benzoquinonyl, phenanthrenyl, peryll, phenanthrenyl, pentacenyl, benzopyrenyl, terphenyl, biphenyl, fluorenyl, cis-or trans-indenofluorenyl, Pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinylamidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazoanthrenyl, 2, 7-diazenyl, 23-diazenyl group, 1, 6-diazenyl group, 1, 8-diazenyl group, 4,5,9, 10-tetraazaperyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 4-diazenyl group, 4-triazolyl group, 1,2, 4-thiadiazolyl group, 1, 3-triazinyl group, 1, 3-thiadiazolyl group, 1,2, 3-thiadiazolyl group, and the like, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination selected from the two groups;
said R7A substituent selected from: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluorescent anthracyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, spirodicloro-yl, dihydrophenanthryl, anthryl, and spiromesic-or trans-indenofluorenyl, Isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazoylOxazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthronyl, 2, 7-diazylpyryl, 2, 3-diazylpyryl, 1, 6-diazylpyryl, 1, 8-diazylpyryl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,2, 4-thiadiazolyl, One of 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination selected from the two groups;
said R8、R9And R10Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, terp, Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolylPyridoimidazolyl, pyrazinoyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthracenyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthronyl, 2, 7-diazepyryl, 2, 3-diazepyryl, 1, 6-diazepyryl, 1, 8-diazepyryl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, one of 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two groups selected therefrom.
8. The compound of claim 1, selected from the compounds of the following specific structures:
9. use of a compound according to any one of claims 1 to 8 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
further, the compound is applied to be used as a luminescent layer material in an organic electroluminescent device, and particularly used as a luminescent material in a luminescent layer.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain therein a compound according to any one of claims 1 to 8;
furthermore, the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, wherein the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is arranged between the hole transport region and the electron transport region; wherein the light-emitting layer contains the compound according to any one of claims 1 to 8.
Background
Organic Light Emission Diodes (OLED) are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
In the aspect of selection of OLED luminescent materials, the singlet luminescent fluorescent material has the advantages of long service life, low price and low efficiency; triplet-emitting phosphorescent materials are efficient, but expensive, and the problem of lifetime of blue materials has not been solved. Adachi at kyushu university of japan proposes a new class of organic light emitting materials, i.e., Thermally Activated Delayed Fluorescence (TADF) materials. Singlet-triplet energy gap (Delta E) of the materialST) Very small (<0.3eV), triplet excitons may be converted into singlet excitons by reverse intersystem crossing (RISC) to emit light, and thus the internal quantum efficiency of the device may reach 100%.
In the prior art, a new structural compound design is performed by adopting a multiple resonance induced thermal activation delayed fluorescence (MR-TADF) strategy, for example, patent applications CN107851724, CN108431984, CN110407858 and the like design polycyclic aromatic compounds formed by connecting a plurality of aromatic rings by boron atoms and nitrogen atoms or oxygen atoms, i.e., a special rigid molecular system containing boron (B) atoms, nitrogen (N) atoms/oxygen (O) atoms is constructed. Although the thermally activated delayed fluorescence molecules can have both high radiative transition rate and high color purity, the larger HOMO-LUMO overlap leads to larger single and triplet state energy range difference (delta Est) of the material, thereby generating serious device efficiency roll-off.
Disclosure of Invention
In one aspect, the present invention provides an organic compound having a structure represented by formula (1):
in formula (1):
D1and D2Each independently selected from NR5、NR6One of O or S;
W1and W2Each independently is C, CH or CR7；
Ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from an aromatic ring of C6-C60 or a heteroaromatic ring of C3-C60, wherein the heteroatom in the heteroaromatic ring group is selected from one or more of Si, Ge, N, P, O, S and Se;
ring Ar3And R6Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
ring Ar4And ring R5Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
R6and W2Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
R5and W1Are not connected to each other, or are connected by C-C single bonds, or are connected by O, S or Se, or are connected by CR8R9Or NR10Connecting;
R1、R2、R3and R4Each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted chain alkyl of C1-C30, substituted or unsubstituted cycloalkyl of C3-C20, substituted or unsubstituted aralkyl of C7-C30, substituted or unsubstituted alkoxy of C1-C30, substituted or unsubstituted aliphatic chain hydrocarbon amine of C2-C30, substituted or unsubstituted cyclic aliphatic chain hydrocarbon amine of C4-C30, substituted or unsubstituted arylamine of C6-C30, substituted or unsubstituted heteroaryl of C3-C30, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted arylboron of C6-C60, and substituted or unsubstituted C3-C60 heteroaryl;
n1, n2, n3 and n4 are each independently selected from integers of 0 to 10; preferably, n1, n2, n3 and n4 are each independently selected from integers of 1 to 5;
when n1 is an integer greater than 1, multiple R1Are identical to each otherOr are different, and a plurality of R1Can be connected into a ring;
when n2 is an integer greater than 1, multiple R2Are the same or different, and a plurality of R2Can be connected into a ring;
when n3 is an integer greater than 1, multiple R3Are the same or different, and a plurality of R3Can be connected into a ring;
when n4 is an integer greater than 1, multiple R4Are the same or different, and a plurality of R4Can be connected into a ring;
R5and R6Each independently selected from one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; preferably, said R is5And R6Each independently selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; more preferably, R is5And R6Each independently selected from any one of substituted or unsubstituted benzene ring, naphthalene ring and anthracene ring; most preferably, said R5And R6Each independently a substituted or unsubstituted benzene ring.
R7One selected from deuterium, halogen, cyano, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; preferably, said R is7One selected from deuterium, halogen, cyano, chain alkyl of C1-C6, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; more preferably, R is7Any one selected from deuterium, halogen, cyano, and substituted or unsubstituted benzene rings;
R8、R9and R10Each independentlyOne selected from substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; preferably, R8And R9Each independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
when R is as defined above1、R2、R3、R4、R5、R6、R7、R8、R9And R10When the above substituents independently exist, the substituents independently exist, and are selected from one or a combination of two of halogen, cyano, chain alkyl of C1-C20, cycloalkyl of C3-C20, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryloxy of C6-C30, aryl of C6-C30, substituted or unsubstituted arylboron of C6-C60, and heteroaryl of C3-C30.
Further, in the general formula (1), D is1Is NR5，D2Is NR6And R is5And R6The same or different; preferably, R5And R6The same is true.
Still further, the general formula (1) is more preferably the following structural formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1-6):
in the formulae (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), W1And W2、R1-R6、Ar1-Ar4And n1-n4 are each as defined in formula (1).
Further preferably, the ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from an aromatic ring of C6-C60 or a heteroaromatic ring of C3-C30; more preferably, ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from an aromatic ring of C6-C30 or a heteroaromatic ring of C3-C20; more preferably, ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently selected from any one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan or thiophene; most preferably, the ring Ar1Ring Ar2Ring Ar3And ring Ar4Each independently a benzene ring.
Further, R mentioned above1、R2、R3And R4Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluorescent anthracyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, spirodicloro-yl, dihydrophenanthryl, anthryl, and spiromesic-or trans-indenofluorenyl, Isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzoImidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazoanthrylyl, 2, 7-diazapyl, 2, 3-diazapyl, 1, 6-diazapyl, 1, 8-diazapyl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocaineyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, pyrazinyl, naphthoxazolyl, phenanthrolinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocyclonyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, One of benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, diphenylboryl, dimyristylboryl, dipentafluorophenylboryl, bis (2,4, 6-triisopropylphenyl) boryl, or a combination of two or more selected from these groups.
Said R5And R6Each independently selected from the following substituents: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridecyl, spiroisotridecyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, benzoquinonyl, phenanthrenyl, peryll, phenanthrenyl, pentacenyl, benzopyrenyl, terphenyl, biphenyl, fluorenyl, cis-or trans-indenofluorenyl, Pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthrimidazolylPyridoimidazolyl, pyrazinoyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthracenyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthronyl, 2, 7-diazepyryl, 2, 3-diazepyryl, 1, 6-diazepyryl, 1, 8-diazepyryl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, one of 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two groups selected therefrom;
said R7A substituent selected from: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluorescent anthracyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, spirodicloro-yl, dihydrophenanthryl, anthryl, and spiromesic-or trans-indenofluorenyl, Isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzofuranyl, dibenzofuranyl, thiophenyl, and thiophenyl-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaloiyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazahrenyl, 2, 7-diazapyl, 2, 3-diazapyl, 1, 6-diazapyl, 1, 8-diazapyl, 4,5,9, 10-tetraazapyryl, perylene, One of pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazinyl, or a combination selected from the two above.
Said R8、R9And R10Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, etc., p-o, etc Dibenzofuranyl, thienyl, benzoThienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthrenyl, 2, 7-diazainyl pyrenyl, pyridyl, quinolyl, isoquinolyl, quinoxalinyl, 1, 5-diazaanthrenyl, 2, 7-diazainyl, 2, 3-diazenylene group, 1, 6-diazenylene group, 1, 8-diazenylene group, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 4-diazenylene group, 4-tetrazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 3-thiadiazolyl group, 1, 3-thiadiazolyl group, 1,2, 3-thiadiazolyl group, and a, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two of the foregoing.
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings. The monocyclic aryl group means that one or at least two phenyl groups are contained in a molecule, and when the at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are connected by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the specification, the C6-C60 aryl group, preferably the C6-C30 aryl group, preferably the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthyl, triphenylene, pyrenyl, perylenyl, perylene, and the like,A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 99 '-dimethylfluorene, 9' -spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
In the specification, the heteroaryl group of C3-C60 is preferably a heteroaryl group of C4-C30, preferably the heteroaryl group is furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl or derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
The aryloxy group in the present specification includes a monovalent group composed of the above aryl group, heteroaryl group and oxygen.
Examples of the alkoxy group in the present specification include the above-mentioned linear alkyl group or a monovalent group composed of a cycloalkyl group and oxygen.
Examples of the arylamine group having C6 to C60 mentioned in the present specification include: phenylamino, methylphenylamino, naphthylamino, anthracylamino, phenanthrylamino, biphenylamino and the like.
Examples of the heteroarylamino group having C6 to C60 mentioned in the present specification include: pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.
Further, the compound represented by the general formula (1) of the present invention may preferably be a compound having the following specific structure: c1-1 to C1-135, C2-1 to C2-78, C3-1 to C3-78, C4-1 to C4-43, C5-1 to C5-43, C6-1 to C6-43, these compounds being representative only:
the structural characteristics of the compounds of the invention are as follows: in the mother nucleus structure shown as the general formula (1), two boron atoms are designed at the 1 and 4 positions of a central benzene ring, and two nitrogen atoms are designed and introduced at the 2 and 5 positions of the central benzene ring, or the combination of every two of the nitrogen atoms, the oxygen atoms and the sulfur atoms is introduced. On one hand, the separation of HOMO and LUMO can be realized by utilizing the resonance effect between boron atoms and nitrogen atoms, or between boron atoms and oxygen atoms, or between boron atoms and nitrogen atoms and oxygen atoms, and meanwhile, the hybridized condensed ring units of boron atoms, nitrogen atoms, oxygen atoms and sulfur atoms have rigid skeleton structures, so that the relaxation degree of an excited state structure can be reduced, and the narrower half-peak width is realized. On the other hand, compared with the multiple resonance structural schemes of nitrogen boron nitrogen, oxygen boron oxygen, nitrogen boron oxygen, boron nitrogen boron and the like commonly used in the prior art, the general structural scheme of the compound limits the resonance of boron atoms with nitrogen and oxygen atoms, so that the compound does not have the thermal activation delayed fluorescence property. Therefore, when the compound of the present invention is used as a material of a light emitting layer in a sensitized organic electroluminescent device, the exciton life in the device can be effectively shortened, thereby the roll-off of the device at high luminance is reduced, and the life of the device is prolonged.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
The second aspect of the present invention also protects the use of a compound represented by any one of the above general formula (1), general formula (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6) as a functional material in an organic electronic device comprising: an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper, preferably an organic electroluminescent device.
In a third aspect, the present invention also provides an organic electroluminescent device comprising a substrate including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers contain a compound represented by any one of the above general formula (1), general formula (1-1), (1-2), (1-3), (1-4), (1-5), and (1-6).
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains the compound represented by the general formula (1) of the present invention.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
The basic chemical materials of various chemicals used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, methylene chloride, acetic acid, potassium carbonate, etc., are commercially available from Shanghai Tantake technology, Inc. and Xiong chemical, Inc. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthetic route:
more specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthetic examples
Synthesis example 1:
synthesis of Compound C1-1
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 6 hours of reaction with phenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) at room temperature, the solvent was removed by vacuum spin-drying and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to give the title compound C1-1(2.80g, 32% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 584.36 elemental analysis results: theoretical value: 86.33 percent of C; 5.18 percent of H; 3.70 percent of B; 4.79 percent of N; experimental values: 86.31 percent of C; 5.19 percent of H; n is 4.82 percent.
Synthesis example 2:
synthesis of Compound C1-11
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-11(3.61g, 36% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 668.41 elemental analysis results: theoretical value: 86.24 percent of C; 6.33 percent of H; 3.23 percent of B; 4.19 percent of N; experimental values: 86.20 percent of C; 6.34 percent of H; and 4.22 percent of N.
Synthetic example 3:
synthesis of Compound C1-16
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.49g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature for reaction for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-16(4.49g, 45% yield, HPLC analytical purity 99%) as an orange yellow solid. MALDI-TOF-MS results: molecular ion peaks: 664.41 elemental analysis results: theoretical value: 86.77 percent of C; 5.76 percent of H; 3.25 percent of B; 4.22 percent of N; experimental values: 86.74 percent of C; 5.75 percent of H; n is 4.21 percent.
Synthetic example 4:
synthesis of Compound C1-17
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.49g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried by vacuum and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-17(0.89g, 9% yield, HPLC analytical purity 99%) as an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 664.52 elemental analysis results: theoretical value: 86.77 percent of C; 5.76 percent of H; 3.25 percent of B; 4.22 percent of N; experimental values: 86.78 percent of C; 5.79 percent of H; and 4.19 percent of N.
Synthesis example 5:
synthesis of Compound C1-21
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trifluoromethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-21(3.11g, 21% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 988.43 elemental analysis results: theoretical value: 58.34 percent of C; 2.04 percent of H; 2.19 percent of B; 2.83 percent of N; 34.60 percent of F; experimental values: 58.78 percent of C; 2.06 percent of H; 2.81 percent of N.
Synthetic example 6:
synthesis of Compound C1-28
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.55g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After a 2-thiophenemagnesium bromide solution in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being spin-dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-28(2.77g, 31% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 596.22 elemental analysis results: theoretical value: 76.53 percent of C; 4.39 percent of H; 3.63 percent of B; 4.70 percent of N; 10.75 percent of S; experimental values: 76.50 percent of C; 4.39 percent of H; 10.72 percent of S.
Synthetic example 7:
synthesis of Compound C1-38
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.97g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-38(2.92g, 28% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 696.52 elemental analysis results: theoretical value: 82.78 percent of C; 5.50 percent of H; 3.10 percent of B; 4.02 percent of N; 4.59 percent of O; experimental values: 82.79 percent of C; 5.49 percent of H; and 4.05 percent of N.
Synthesis example 8:
synthesis of Compound C1-42
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (11.86g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature for reaction for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-42(4.67g, 35% yield, HPLC analytical purity 99%) as an orange yellow solid. MALDI-TOF-MS results: molecular ion peaks: 888.78 elemental analysis results: theoretical value: 86.48 percent of C; 7.94 percent of H; 2.43 percent of B; 3.15 percent of N; experimental values: 86.51 percent of C; 7.88 percent of H; and 3.17 percent of N.
Synthetic example 9:
synthesis of Compound C1-78
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (11.50g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2, 6-dimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature to react for 6 hours, the solvent was stopped from being dried by vacuum spin-drying, and a silica gel column was passed over (developing agent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-78(1.88g, 15% yield, HPLC analytical purity 99%) as a reddish brown solid. MALDI-TOF-MS results: molecular ion peaks: 836.51 elemental analysis results: theoretical value: 89.01 percent of C; 5.06 percent of H; 2.58 percent of B; 3.35 percent of N; experimental values: 88.96 percent of C; 5.02 percent of H; n is 3.37 percent.
Synthetic example 10:
synthesis of Compound C1-117
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (10.18g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature for reaction for 6 hours, the solvent was stopped from being dried by vacuum spin-drying, and the mixture was passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-117(2.33g, 20% yield, HPLC analytical purity 99%) as an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 776.51 elemental analysis results: theoretical value: 86.60 percent of C; 7.01 percent of H; b, 2.78 percent; 3.61 percent of N; experimental values: 86.65 percent of C; 6.96 percent of H; and 3.59 percent of N.
Synthetic example 11:
synthesis of Compound C1-121
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br precursor (13.45g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried by vacuum spin-drying and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-121(1.79g, 12% yield, HPLC analytical purity 99%) as a deep red solid. MALDI-TOF-MS results: molecular ion peaks: 994.71 elemental analysis results: theoretical value: 86.93 percent of C; 5.27 percent of H; 2.17 percent of B; 5.63 percent of N; experimental values: 86.85 percent of C; 5.21 percent of H; and 5.59 percent of N.
Synthetic example 12:
synthesis of Compound C1-129
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.19g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried by vacuum and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-129(1.93g, 20% yield, HPLC analytical purity 99%) as an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 644.45 elemental analysis results: theoretical value: 82.01 percent of C; 5.32 percent of H; 3.36 percent of B; 4.35 percent of N; o: 4.97% Experimental value: 82.05 percent of C; 5.31 percent of H; n is 4.31 percent.
Synthetic example 13:
synthesis of Compound C2-7
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (7.40g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C1-117(2.93g, 33% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 591.41 elemental analysis results: theoretical value: 85.30 percent of C; 5.97 percent of H; 3.66 percent of B; 2.37 percent of N; 2.71 percent of O; experimental values: 85.35 percent of C; 5.96 percent of H; 2.39 percent of N.
Synthesis example 14:
synthesis of Compound C2-21
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.06g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C2-21(2.67g, 28% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 635.31 elemental analysis results: theoretical value: 85.06 percent of C; 6.82 percent of H; 3.40 percent of B; 2.20 percent of N; 2.52 percent of O; experimental values: 85.08 percent of C; 6.86 percent of H; 2.19 percent of N.
Synthetic example 15:
synthesis of Compound C2-48
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.93g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2, 6-dimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature to react for 6 hours, the solvent was stopped from being dried by vacuum spin-drying, and a silica gel column was passed (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C2-48(1.50g, 15% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 665.63 elemental analysis results: theoretical value: 86.64 percent of C; 5.60 percent of H; 3.25 percent of B; 2.10 percent of N; 2.40 percent of O; experimental values: 85.58 percent of C; 5.56 percent of H; 2.13 percent of N.
Synthetic example 16:
synthesis of Compound C3-7
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (7.64g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature for reaction for 6 hours, the solvent was stopped from being dried by vacuum spin-drying, and the mixture was passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C3-7(1.69g, 16% yield, HPLC analytical purity 99%) as an orange yellow solid. MALDI-TOF-MS results: molecular ion peaks: 703.31 elemental analysis results: theoretical value: 61.49 percent of C; 2.86 percent of H; 3.07 percent of B; 27.02 percent of F; 1.99 percent of N; 4.56 percent of S; experimental values: 61.45 percent of C; 2.88 percent of H; 2.02 percent of N; 4.58 percent of S; .
Synthetic example 17:
synthesis of Compound C3-37
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (7.64g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 6 hours of reaction with a tetrahydrofuran solution of pentafluorophenyl magnesium bromide (30mL,1.0M,30mmol) at room temperature, the solvent was stopped from being dried by vacuum, and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to give the title compound C3-37(2.10g, 23% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 607.41 elemental analysis results: theoretical value: 83.05 percent of C; 5.81 percent of H; 3.56 percent of B; 2.31 percent of N; 5.28 percent of S; experimental values: 83.09 percent of C; 5.78 percent of H; 2.32 percent of N; 5.31 percent of S; .
Synthetic example 18:
synthesis of Compound C4-2
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (6.30g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C4-2(2.33g, 30% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 518.31 elemental analysis results: theoretical value: 83.43 percent of C; 6.22 percent of H; 4.17 percent of B; 6.17 percent of O; experimental values: 83.45 percent of C; h is 6.28 percent.
Synthetic example 19:
synthesis of Compound C4-20
Under a nitrogen atmosphere, a solution of n-butyllithium in pentane (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (8.34g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C4-20(2.36g, 24% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 654.38 elemental analysis results: theoretical value: 69.76 percent of C; 4.62 percent of H; 3.30 percent of B; 17.42 percent of F; 4.89 percent of O; experimental values: 69.78 percent of C; h is 4.58 percent.
Synthesis example 20:
synthesis of Compound C5-2
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (6.54g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C5-2(1.76g, 22% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 534.31 elemental analysis results: theoretical value: 80.92 percent of C; 6.04 percent of H; b, 4.05 percent; 2.99 percent of O; 6.00 percent of S; experimental values: 80.95 percent of C; 5.98 percent of H; 6.02 percent of S.
Synthetic example 21:
synthesis of Compound C5-4
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (6.96g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C5-4(2.36g, 28% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 562.48 elemental analysis results: theoretical value: 81.16 percent of C; 6.45 percent of H; 3.84 percent of B; 2.84 percent of O; 5.70 percent of S; experimental values: 81.15 percent of C; 6.42 percent of H; 5.72 percent of S.
Synthetic example 22:
synthesis of Compound C6-2
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (12mL, 2.50M, 30mmol) was slowly added to a solution of Br generation precursor (6.78g, 15mmol) in tert-butylbenzene (150mL) at 0 deg.C, followed by heating to 25 deg.C for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (7.52g, 30mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (7.76g, 60mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 h. After 2,4, 6-trimethylphenylmagnesium bromide in tetrahydrofuran (30mL,1.0M,30mmol) was added at room temperature and reacted for 6 hours, the solvent was stopped from being dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether ═ 1:10) to obtain the objective compound C6-2(1.95g, 23% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 565.58 elemental analysis results: theoretical value: 78.60 percent of C; 6.24 percent of H; 3.82 percent of B; 11.34 percent of S; experimental values: 78.55 percent of C; 6.30 percent of H; 11.38 percent of S.
The photophysical properties of representative fused ring compounds of the present invention prepared in the above synthesis examples of the present invention are shown in Table 1.
Table 1:
note that in Table 1,. DELTA.EST is the difference between the singlet level and the triplet level, and the difference between the initial (onset) value of the fluorescence spectrum and the phosphorescence spectrum was measured by dissolving the compound in toluene at a concentration of 10-5mol/L to prepare a sample to be measured. The instrument is Edinburg FLS1000 (UK); the half-peak width is the peak width at half of the peak height of the fluorescence spectrum at room temperature, namely a straight line parallel to the peak bottom is drawn through the midpoint of the peak height, and the straight line and the distance between two intersecting points at two sides of the peak are determined, wherein the fluorescence spectrum is obtained by dissolving a compound in toluene at a concentration of 10-5mol/L to prepare a sample to be tested and testing the sample by using a fluorescence spectrometer (Edinburg FLS1000 (UK)).
As can be seen from table 1, the fused ring compounds in the examples provided by the present invention have a large Δ EST (>0.3eV) and do not have a thermally activated delayed fluorescence effect. Meanwhile, the luminescent compound provided by the invention shows narrower half-peak width (<35 nm).
The technical effects and advantages of the invention are shown and verified by testing practical use performance by specifically applying the compound of the invention to an organic electroluminescent device.
The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material may be divided into a plurality of regions, for example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
As a material of the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), or zinc oxide (ZnO), or any combination thereof can be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives, and the like.
The light emitting layer includes a light emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include both a sensitizer (sensitizer) and a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
1. the anode material coated glass plate was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
2. placing the glass plate with the anode in a vacuum chamber, vacuumizing to 1 x 10 < -5 > to 8 x 10 < -4 > Pa, and performing vacuum evaporation on the anode layer film to form a hole injection layer by using a hole injection material, wherein the evaporation rate is 0.1-0.5 nm/s;
3. vacuum evaporating a hole transport material on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1-0.5 nm/s;
4. the organic light-emitting layer of the device is vacuum evaporated on the hole transport layer, the organic light-emitting layer material comprises a main body material, a sensitizing agent and a dye, and the evaporation rate of the main body material, the evaporation speed of the sensitizing agent material and the evaporation rate of the dye are adjusted by a multi-source co-evaporation method to enable the dye to reach a preset doping proportion;
5. forming an electron transport layer on the organic light-emitting layer by vacuum evaporation of an electron transport material of the device, wherein the evaporation rate is 0.1-0.5 nm/s;
6. LiF is evaporated on the electron transport layer in vacuum at a speed of 0.1-0.5nm/s to serve as an electron injection layer, and an Al layer is evaporated on the electron transport layer in vacuum at a speed of 0.5-1nm/s to serve as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device provided as above. The display device can be specifically a display device such as an OLED display, and any product or component with a display function including the display device, such as a television, a digital camera, a mobile phone, a tablet computer, and the like. The display device has the same advantages as the organic electroluminescent device compared with the prior art, and the description is omitted here.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
Device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-1 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D1 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, sky blue light emission (driving voltage of 2.6V) having a wavelength of 495nm, a half-peak width of 30nm, CIE color coordinates (x, y) (0.11,0.52), and an external quantum efficiency EQE of 28.3% was obtained.
Device example 2
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-11(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-11 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D2 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, a sky blue light emission (driving voltage of 2.5V) having a wavelength 497nm, a half-peak width of 2920nm, CIE color coordinates (x, y) (0.12,0.55) and an external quantum efficiency EQE of 29.1% was obtained.
Device example 3
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-16(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-16 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D3 prepared in this example were as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, green light emission (driving voltage of 2.4V) with a wavelength of 521nm, a half-peak width of 27nm, CIE color coordinates (x, y) ((0.23, 0.70)) and an external quantum efficiency EQE of 32.6% was obtained.
Device example 4
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-17(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-17 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D4 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, yellow light emission (driving voltage of 2.3V) with a wavelength of 552nm, a peak width at half maximum of 25nm, CIE color coordinates (x, y) (0.40,0.60), and external quantum efficiency EQE of 31.2% was obtained.
Device example 5
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-21(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-21 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D5 prepared in this example were as follows: when a dc voltage was applied and the characteristics of 10cd/m2 light emission were measured, yellow light emission (driving voltage of 2.3V) with a wavelength of 565nm, a half-peak width of 27nm, CIE color coordinates (x, y) (0.47,0.53), and an external quantum efficiency EQE of 25.2% was obtained.
Device example 6
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-28(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-28 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D6 prepared in this example were as follows: when a dc voltage was applied and the characteristics of 10cd/m2 light emission were measured, green light emission (driving voltage of 2.3V) having a wavelength of 535nm, a peak width at half maximum of 33nm, CIE color coordinates (x, y) (0.30,0.68), and an external quantum efficiency EQE of 28.7% was obtained.
Device example 7
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-38(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-38 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D7 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, green light emission (driving voltage of 2.4V) with a wavelength of 540nm, a peak width at half maximum of 33nm, CIE color coordinates (x, y) (0.33,0.65), and external quantum efficiency EQE of 29.3% was obtained.
Device example 8
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-42(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-42 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D8 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, green light emission (driving voltage of 2.4V) with a wavelength of 536nm, a half-peak width of 30nm, CIE color coordinates (x, y) (0.33,0.63), and an external quantum efficiency EQE of 32.0% was obtained.
Device example 9
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-78(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-78 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D9 prepared in this example were as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, orange light emission (driving voltage of 2.2V) having a wavelength of 572nm, a peak width at half maximum of 32nm, CIE color coordinates (x, y) (0.50,0.49), and external quantum efficiency EQE of 26.8% was obtained.
Device example 10
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-117(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-117 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D10 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, yellow light emission (driving voltage of 2.3V) with a wavelength of 560nm, a peak width at half maximum of 26nm, CIE color coordinates (x, y) ((0.44, 0.55)) and an external quantum efficiency EQE of 27.9% was obtained.
Device example 11
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-121(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-121 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D11 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, red light emission (driving voltage of 2.1V) having a wavelength of 612nm, a half-peak width of 32nm, CIE color coordinates (x, y) (0.66,0.33), and external quantum efficiency EQE of 26.6% was obtained.
Device example 12
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1-129(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1-129 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D12 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, yellow light emission (driving voltage of 2.3V) with a wavelength of 556nm, a peak width at half maximum of 34nm, CIE color coordinates (x, y) ((0.42, 0.57)) and an external quantum efficiency EQE of 28.1% was obtained.
Device example 13
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C2-7(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C2-7 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D13 prepared in this example were as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, green light emission (driving voltage of 2.4V) with a wavelength of 505nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) (0.15,0.63), and external quantum efficiency EQE of 29.7% was obtained.
Device example 14
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C2-21(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C2-21 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D14 prepared in this example were as follows: when a dc voltage was applied and the characteristics of 10cd/m2 light emission were measured, green light emission (driving voltage of 2.1V) with a wavelength of 512nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) (0.21,0.68), and external quantum efficiency EQE of 30.2% was obtained.
Device example 15
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C2-48(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C2-48 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D15 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, yellow light emission (driving voltage of 2.3V) having a wavelength of 550nm, a peak width at half maximum of 33nm, CIE color coordinates (x, y) (0.39,0.59), and external quantum efficiency EQE of 27.7% was obtained.
Device example 16
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C3-7(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C3-7 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D16 prepared in this example were as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, green light emission (driving voltage of 2.4V) with a wavelength of 510nm, a half-peak width of 32nm, CIE color coordinates (x, y) (0.18,0.67), and an external quantum efficiency EQE of 29.1% was obtained.
Device example 17
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C3-37(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C3-37 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D17 prepared in this example were as follows: when a dc voltage was applied and the characteristics of 10cd/m2 light emission were measured, green light emission (driving voltage of 2.4V) having a wavelength of 529nm, a half-peak width of 31nm, CIE color coordinates (x, y) (0.26,0.68), and an external quantum efficiency EQE of 28.3% was obtained.
Device example 18
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C4-2(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C4-2 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D18 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, blue light emission (driving voltage of 2.6V) with a wavelength of 483nm, a half-peak width of 29nm, CIE color coordinates (x, y) (0.12,0.28) and an external quantum efficiency EQE of 29.8% was obtained.
Device example 19
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C4-20(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20 wt%, C4-20 is dye and has a doping concentration of 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D19 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, blue light emission (driving voltage of 2.7V) with a wavelength of 475nm, a half-peak width of 29nm, CIE color coordinates (x, y) (0.13,0.22), and an external quantum efficiency EQE of 28.2% was obtained.
Device example 20
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C5-2(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C5-2 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D20 prepared in this example were as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, sky blue light emission (driving voltage of 2.6V) having a wavelength of 496nm, a half-peak width of 30nm, CIE color coordinates (x, y) ((0.13, 0.56)) and an external quantum efficiency EQE of 28.7% was obtained.
Device example 21
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C5-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C5-4 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D21 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, green light emission (driving voltage of 2.4V) with a wavelength of 501nm, a half-peak width of 30nm, CIE color coordinates (x, y) (0.14,0.60), and external quantum efficiency EQE of 29.1% was obtained.
Device example 22
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C6-2(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C6-2 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, this embodiment is 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device D22 prepared in this example were as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, green light emission (driving voltage of 2.4V) with a wavelength of 508nm, a peak width at half maximum of 32nm, CIE color coordinates (x, y) (0.16,0.67), and an external quantum efficiency EQE of 28.2% was obtained.
Comparative device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C1 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device CD1 prepared in this example are as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, blue light emission (driving voltage of 2.9V) having a wavelength of 464nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) ((0.15, 0.09)) and an external quantum efficiency EQE of 26.2% was obtained.
Comparative device example 2
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C2(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C2 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device CD2 prepared in this example are as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, yellow light emission (driving voltage of 3.0V) with a wavelength of 451nm, a half-peak width of 31nm, CIE color coordinates (x, y) (0.13,0.16), and external quantum efficiency EQE of 27.2% was obtained.
Comparative device example 3
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C3(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C3 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device CD3 prepared in this example are as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, blue light emission (driving voltage of 3.4V) having a wavelength of 431nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) ((0.13, 0.06)) and an external quantum efficiency EQE of 18.2% was obtained.
Comparative device example 4
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C4 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device CD4 prepared in this example are as follows: when a dc voltage was applied and the characteristics were measured at 10cd/m2 light emission, blue light emission (driving voltage of 3.4V) with a wavelength of 428nm, a half-peak width of 29nm, CIE color coordinates (x, y) ((0.12, 0.06)) and an external quantum efficiency EQE of 16.5% was obtained.
Comparative device example 5
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:3wt％C5(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5 nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30 nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20 wt%, C2 is dye and doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
The device performance results of the organic electroluminescent device CD2 prepared in this example are as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, blue light emission (driving voltage of 3.2V) with a wavelength of 452nm, a half-peak width of 32nm, CIE color coordinates (x, y) ((0.13, 0.08)) and an external quantum efficiency EQE of 21.1% was obtained.
The structural formulas of the various organic materials used in the above examples are as follows:
the above C1-C5 as comparative compounds are compounds in the prior art, and the synthesis methods thereof can be found in patent applications CN107851724, CN108431984, CN110407858, CN110776509 and the like, and are not described herein again.
The properties of the organic electroluminescent devices prepared in the above examples and comparative examples are shown in Table 2 below.
Table 2:
in the case of examples 1 to 22 and comparative examples 1 and 2, the compounds according to the present invention have a very narrow electroluminescence spectrum in the case where other materials are the same in the structure of the organic electroluminescent device. Meanwhile, compared with the multiple resonance TADF dye with a nitrogen-boron-nitrogen structure in a comparative example, the device prepared by the compound provided by the invention has lower lighting voltage and greatly improved roll-off. This is mainly because the structure of the compound of the present invention limits the resonance of boron atoms with nitrogen and oxygen atoms, and does not have the property of thermal activation delayed fluorescence. When the compound of the present invention is used as a light emitting layer material in a sensitized organic electroluminescent device, excitons do not stay in a triplet state, thereby reducing roll-off of the device at high luminance and extending the lifetime of the device.
In the case of examples 1 to 22 and comparative examples 3,4 and 5, the compounds according to the present invention have a very narrow electroluminescence spectrum in the case where other materials are the same in the structure of the organic electroluminescent device. Meanwhile, compared with the situation that boron nitrogen or boron oxygen is in the ortho position in the comparative example, the device prepared by the compound provided by the invention has lower lighting voltage and greatly improved efficiency and roll-off.
The experimental data show that the novel organic material is used as a light-emitting object of an organic electroluminescent device, is an organic light-emitting functional material with good performance, and is expected to be popularized and applied commercially.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
