1. A spirobifluorene compound having a structural formula as shown in formula (I) or formula (II):

wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

r is selected from H, D, halogen, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C1-C40 cycloalkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C1-C40 heteroaryl, substituted or unsubstituted C1-C60 silicon base, substituted or unsubstituted C6-C60 aromatic fused ring or substituted or unsubstituted C1-C60 heteroaromatic fused ring, and n is an integer from 0 to 10.

2. The spirobifluorene compound according to claim 1, wherein said compound is selected from the group consisting of:

wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

r is selected from H, D, halogen, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C1-C40 cycloalkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C1-C40 heteroaryl, substituted or unsubstituted C1-C60 silicon base, substituted or unsubstituted C6-C60 aromatic fused ring or substituted or unsubstituted C1-C60 heteroaromatic fused ring, and n is an integer from 0 to 10.

3. The spirobifluorene compound according to claim 1 or 2, wherein R in said compound is selected from the group consisting of:

wherein, the un-deuterated group in the structure can be partially or completely deuterated.

4. The spirobifluorene compound according to claim 1 or 2, wherein Ar1 and Ar2 in said compound are each independently selected from the group consisting of:

wherein, the un-deuterated group in the structure can be partially or completely deuterated.

5. The spirobifluorene compound according to claim 1 or 2, wherein said compound is selected from the group consisting of:

。

6. a formulation comprising the spirobifluorene compound according to claim 1 or 2 and at least one solvent, wherein the solvent is an unsaturated hydrocarbon solvent, a saturated hydrocarbon solvent, an ether solvent or an ester solvent.

7. An organic light emitting device comprising a cathode layer, an anode layer, and an organic functional layer which is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, wherein the organic functional layer comprises the spirobifluorene compound according to claim 1 or 2.

8. The organic light-emitting device according to claim 7, wherein the organic functional layer is a light-emitting layer further comprising a guest compound, wherein,

the volume ratio of the spirobifluorene compound to the guest compound is 1: 99 to 99: 1; the guest material is a fluorescent material or a phosphorescent material.

9. An organic light-emitting device according to claim 7, wherein the light-emitting layer further comprises the spirobifluorene compound according to claim 1 or 2 as a first host and another organic compound as a second host, the volume ratio of the first host to the second host being 8: 2 to 2: 8.

10. the organic light-emitting device according to claim 7, wherein the organic functional layer is an electron transport layer, and the spirobifluorene compound may form the electron transport layer alone or together with a dopant; when the dopant is contained in the electron transport layer, the volume ratio of the spirobifluorene compound to the dopant is 2: 8-8: 2; wherein the dopant is an n-type dopant.

11. A display or lighting apparatus comprising the organic light emitting device of claim 7.

Background

The organic light emitting device (OLED device) has the advantages of wide viewing angle, high response speed, high color quality, capability of realizing flexible light emission and the like, and has wide application prospect. Common OLED devices typically comprise the following classes of organic materials: a hole injection material, a hole transport material, an electron transport material, and light emitting materials (dyes or doped guest materials) of respective colors and corresponding host materials, and the like. Generally, the electron transport rate of a hole transport material is two orders of magnitude higher than the electron transport rate of an electron transport material. Therefore, in order to make the electron and the hole be well combined in the light emitting layer to form an exciton and emit light, a hole blocking layer is generally used to prevent the hole from reaching the electron transport layer in the fabrication of the organic light emitting device. The hole blocking material should have a lower HOMO level, a higher electron transfer rate, a higher triplet level, a higher oxidation potential and a wider band gap to improve the electron transport capability and the hole and exciton blocking capability thereof, so that excitons are limited in the light emitting layer, the loss of light energy is reduced, and the efficiency of the organic light emitting device is greatly improved.

Many organic materials can effectively transport holes, and therefore, in order to improve the light emitting efficiency of the organic light emitting device, in many cases, an electron transport/hole blocking layer is additionally added on the cathode side to block hole transport, so that carrier recombination is limited in the light emitting layer region.

Therefore, it is necessary to develop a Hole-blocking layer (HBL) or an electron-transporting material with high triplet energy level, so that the recombination probability of electrons and holes in the light-emitting layer is increased, the loss of light energy is reduced, and the efficiency of the device is greatly improved; on the other hand, a high triplet energy level is advantageous for the use of high efficiency phosphorescent or TADF materials.

Disclosure of Invention

In order to overcome the problems of the existing organic electron transport materials/hole blocking materials, it is an object of the present invention to provide a spirobifluorene compound having improved electron transport ability and blocking ability of holes and excitons, which confines excitons in a light emitting layer, reduces energy loss, thereby further improving efficiency and lifetime of an organic light emitting device, and reducing operating voltage.

In order to realize the purpose of the invention, the technical scheme of the invention is as follows:

the invention provides a spirobifluorene compound, wherein the structural formula of the spirobifluorene compound is shown as the following formula (I) or formula (II):

。

wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

R is selected from H, D, halogen, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C1-C40 cycloalkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C1-C40 heteroaryl, substituted or unsubstituted C1-C60 silicon base, substituted or unsubstituted C6-C60 aromatic fused ring or substituted or unsubstituted C1-C60 heteroaromatic fused ring, and n is an integer from 0 to 10.

Preferably, the spirobifluorene compound of the present invention is selected from the group consisting of:

。

wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

R is selected from H, D, halogen, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C1-C40 cycloalkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C1-C40 heteroaryl, substituted or unsubstituted C1-C60 silicon base, substituted or unsubstituted C6-C60 aromatic fused ring or substituted or unsubstituted C1-C60 heteroaromatic fused ring, and n is an integer from 0 to 10.

More preferably, the spirobifluorene compound of the present invention has a structural formula in which R is selected from the group consisting of:

。

wherein, the un-deuterated group in the structure can be partially or completely deuterated.

More preferably, the spirobifluorene compound of the present invention has a structural formula in which Ar1 and Ar2 are each independently selected from the group consisting of:

。

wherein, the un-deuterated group in the structure can be partially or completely deuterated.

More preferably, the spirobifluorene compound of the present invention is selected from the group consisting of:

。

the present invention also provides a formulation comprising a spirobifluorene compound and at least one solvent, which may be an unsaturated hydrocarbon solvent (e.g., toluene, xylene, mesitylene, tetralin, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.), a halogenated saturated hydrocarbon solvent (e.g., carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.), a halogenated unsaturated hydrocarbon solvent (e.g., chlorobenzene, dichlorobenzene, trichlorobenzene, etc.), an ether solvent (e.g., tetrahydrofuran, tetrahydropyran, etc.) or an ester solvent (e.g., alkyl benzoate, etc.) known to those skilled in the art.

The invention also provides an organic light-emitting device which comprises a cathode layer, an anode layer and an organic functional layer, wherein the organic functional layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and an electron injection layer, and the organic functional layer contains a spirobifluorene compound or a preparation. The hole transport layer and the electron transport layer of the organic light emitting device of the present invention further comprise one or more p-type dopants (e.g., LiQ).

Preferably, the luminescent layer of the organic luminescent device contains the spirobifluorene compound and at least one guest material, wherein the volume ratio of the spirobifluorene compound to the guest material is 1: 99 to 99: 1; the guest material is a fluorescent material or a phosphorescent material.

More preferably, the luminescent layer of the organic luminescent device contains the spirobifluorene compound as a first host and another organic compound as a second host, and the volume ratio of the first host to the second host is 8: 2 to 2: 8.

preferably, the electron transport layer of the organic light-emitting device contains the spirobifluorene compound of the present invention; the spirobifluorene compound can form an electron transport layer independently or can form an electron transport layer together with a dopant; when the electron transport layer contains a dopant, the volume ratio of the spirobifluorene compound to the dopant is 2: 8-8: 2; the dopant is an n-type dopant.

The organic light emitting device of the present invention may be classified as top emission, bottom emission, or double-sided emission. The spirobifluorene compound of the present invention can be applied to an illuminating OLED, a flexible OLED, and the like as well.

The invention also provides a display or lighting device, wherein the display or lighting device comprises the organic light-emitting device.

The spirobifluorene compound is applied to an organic light-emitting device due to asymmetric structural characteristics, so that the efficiency, the service life, the film forming performance and other performances of the device are improved, and the spirobifluorene compound has higher triplet state energy level, so that the energy transfer is more sufficient, the transfer of electrons and holes is more balanced, and the efficiency and the service life of the device are higher under the condition of keeping low operating voltage.

The spirobifluorene compound is mainly characterized in that a substituted triazine group and a pyridine unit are introduced at the same time, and the spirobifluorene compound has the following remarkable effects:

(1) under the synergistic effect of pyridine ring and substituted triazine group, the spirobifluorene compound has higher glass transition temperature;

(2) compared with similar compounds without pyridine groups (such as aryl triazine spirobifluorene compounds), the spirobifluorene compound provided by the invention is applied to an organic light-emitting device, and can improve the efficiency and the service life of the device;

(3) the spirobifluorene compound can well balance the transmission of holes and electrons, so that the operating voltage of an organic light-emitting device is reduced;

drawings

Fig. 1 is a schematic structural view of an organic light emitting device of the present invention, and fig. 2 is a differential thermal scanning (DSC) graph of compound 12 of the present invention.

Detailed Description

In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.

The OLED device of the invention comprises a hole transport layer, which may be selected from known materials, particularly preferably, but not representing a limitation of the invention, from the following structures:

。

the OLED devices of the present invention contain a hole transport layer that includes one or more p-type dopants. Preferred p-type dopants of the present invention are, but do not represent a limitation of the present invention to:

。

the electron transport layer may be selected from one of the reference compounds ET-1 to ET-6 or the spirobifluorene compounds described in the present invention, but does not represent that the present invention is limited to the following structures:

。

the electron transport layer may be formed from an organic material in combination with one or more n-type dopants (e.g., LiQ).

The light-emitting layer is composed of BH-1 as a host and BD-1 as a guest material

。

Synthetic examples

。

The above intermediates 1 to 10 were synthesized by methods known in the art.

Example 1: synthesis of Compound 1

Under nitrogen protection, a reaction vessel was charged with intermediate 1 (10 mmol), 3, 5-diphenyl-1-chlorotriazine (10 mmol), toluene: 105 ml, ethanol: 26 ml, then, potassium carbonate: 5 g of the compound is dissolved in H₂O: 30 ml of the resulting aqueous solution while introducing nitrogen. Adding palladium acetate: 0.1 g, three0.4 g of phenylphosphine was stirred under heating at reflux for 12 hours. After natural cooling, the organic layer was separated and concentrated to give a crude product. After passing the crude product through a silica gel column using a dichloromethane/petroleum ether mixed solution as an eluent, a white solid was obtained, 5.5 g (yield 88%);¹h NMR (400 MHz): Δ 7.21-7.54 (M, 13H), 7.75 (d,1H), 7.81 (d,1H), 7.86-7.98 (M, 6H), 8.12-8.27 (M, 5H), 8.55 (d,1H), 8.68 (s, 1H), LC-MS: M/Z found 625.2 (M + H)⁺Theory 624.23.

Example 2: synthesis of Compound 2

The synthesis steps of the compound 2 are similar to those of the compound 1, the intermediate 2 is selected as a reactant, and the yield is 87%;¹h NMR (400 MHz): Δ 7.26 (dd, 2H), 7.36-7.58 (M, 9H), 7.62 (d, 2H), 7.65 (d, 2H),7.79-7.82 (M, 3H), 7.86 (d, 2H), 8.01 (d,1H), 8.12-8.27 (M, 5H), 8.63 (d, 2H), LC-MS: M/Z found 625.2 (M + H)⁺Theory 624.23.

Example 3: synthesis of Compound 3

The synthesis steps of the compound 3 are similar to those of the compound 1, the intermediate 3 is selected as a reactant, and the yield is 85%;¹h NMR (400 MHz): Δ 7.26 (dd, 2H), 7.46-7.58 (M, 7H), 7.60 (dd, 2H), 7.65 (d, 2H), 7.70-7.78 (M, 3H), 7.92 (d, 2H), 8.11-8.33 (M, 8H), 8.62 (d,1H), 8.71 (s, 1H), LC-MS: M/Z found 625.2 (M + H)⁺Theory 624.23.

Example 4: synthesis of Compound 4

The synthesis steps of the compound 4 are similar to those of the compound 1, the intermediate 4 is selected as a reactant, and the yield is 82%;¹h NMR (400 MHz): delta 7.4-7.62 (M, 16H), 7.80 (d, 2H), 7.85 (d, 2H), 8.21-8.37 (M, 6H), 8.65 (d, 2H), LC-MS, M/Z found 625.2 (M + H)⁺Theory 624.23.

Example 5: synthesis of Compound 5

The synthesis steps of the compound 5 are similar to those of the compound 1, the intermediate 5 is selected as a reactant, and the yield is 82%;¹h NMR (400 MHz): Δ 7.35 (dd, 1H), 7.46-7.52 (M, 8H), 7.53 (dd, 1H), 7.65-7.82 (M, 7H), 7.92 (d,1H), 8.13-8.32 (M, 8H), 8.35 (d,1H), 8.52-8.60 (M, 3H), LC-MS: M/Z found 675.2 (M+H)⁺Theory 674.25.

Example 6: synthesis of Compound 6

The synthesis steps of the compound 6 are similar to those of the compound 1, the intermediate 6 is selected as a reactant, and the yield is 82%;¹h NMR (400 MHz): Δ 7.35 (dd, 1H), 7.46-7.52 (M, 8H), 7.53 (dd, 1H), 7.65-7.82 (M, 7H), 7.92 (d,1H), 8.13-8.32 (M, 8H), 8.35 (d,1H), 8.52-8.60 (M, 3H), LC-MS: M/Z675.2 (M + H) measured⁺Theory 674.25.

Example 7: synthesis of Compound 7

The synthesis steps of the compound 7 are similar to those of the compound 1, the intermediate 7 is selected as a reactant, and the yield is 77%;¹h NMR (400 MHz): Δ 7.25 (dd, 1H), 7.41-7.72 (M, 17H), 7.83 (d,1H), 7.89 (d,1H), 8.13-8.25 (M, 4H), 8.33-8.42 (M, 3H), 8.57-8.66 (M, 3H), LC-MS, M/Z675.2 (M + H) measured⁺Theory 674.25.

Example 8: synthesis of Compound 8

The synthesis steps of the compound 8 are similar to those of the compound 1, the intermediate 2 is selected as a reactant, and the yield is 79%;¹h NMR (400 MHz): Δ 7.35 (dd, 1H), 7.40-7.58 (M, 10H), 7.63 (d, 2H),7.79 (d, 2H), 7.73 (d, 2H),7.79-7.82 (M, 4H), 7.92 (d, 2H), 8.01-8.06 (M, 2H), 8.21-8.33 (M, 4H), 8.36 (d,1H), 8.69 (d, 2H); LC-MS: M/Z found 715.2 (M + H)⁺Theory 714.24.

Example 9: synthesis of Compound 9

The synthesis procedure of the compound 9 is similar to that of the compound 1, the intermediate 3 is selected as a reactant, and the yield is 83%; LC-MS M/Z actual measurement 715.2 (M + H)⁺Theory 714.24.

Example 10: synthesis of Compound 10

The synthesis steps of the compound 10 are similar to those of the compound 1, the intermediate 4 is selected as a reactant, and the yield is 75%;¹h NMR (400 MHz): Δ 7.31(dd, 1H), 7.40-7.68 (M, 16H), 7.75 (d, 2H), 7.99 (d, 2H), 8.01-8.06 (M, 2H), 8.21-8.32 (M, 3H), 8.35 (s, 1H), 8.66 (d, 2H), 8.70 (s, 1H), LC-MS: M/Z found 715.2 (M + H)⁺Theory 714.24.

Example 11: synthesis of Compound 11

The synthesis procedure of compound 11 is similar to that of compound 1, intermediate 5 is selected as a reactant, and the yield is 81%; LC-MS M/Z actual measurement 765.2 (M + H)⁺Theory 764.26.

Example 12: synthesis of Compound 12

The synthesis procedure of the compound 12 is similar to that of the compound 1, the intermediate 7 is selected as a reactant, and the yield is 71%;¹h NMR (400 MHz): Δ 7.23 (dd, 1H), 7.33 (dd, 1H), 7.42-7.61 (M, 10H), 7.65-7.81 (M, 7H), 7.83 (d, 2H), 7.91-8.03 (M, 3H), 8.19 (d,1H), 8.26 (d, 2H), 8.33 (s, 1H), 8.46 (d,1H), 8.56-8.72 (M, 4H); LC-MS: M/Z found 765.2 (M + H)⁺Theory 764.26; glass transition temperature Tg (162.5 degrees).

Example 13: synthesis of Compound 13

The synthesis procedure of compound 13 is similar to that of compound 1, intermediate 8 is selected as a reactant, and the yield is 87%; LC-MS M/Z actual measurement 715.2 (M + H)⁺Theory 714.24.

Example 14: synthesis of Compound 14

The synthesis procedure of compound 14 is similar to that of compound 1, intermediate 4 is selected as a reactant, and the yield is 76%; LC-MS M/Z actual measurement 675.2(M + H)⁺Theory 674.25.

Example 15: synthesis of Compound 15

The synthesis procedure of compound 15 is similar to that of compound 1, intermediate 4 is selected as a reactant, and the yield is 74%;¹h NMR (400 MHz): δ 7.30 (t, 1H), 7.38-7.71 (m, 22H), 7.71 (d,1H), 7.85 (d,1H), 7.93-8.11 (m, 5H), 8.29 (d,1H), 8.36 (s, 1H), 8.39 (s, 1H), 8.46 (d,1H), 8.69 (d, 2H), 8.92 (s, 1H); LC-MS M/Z found 751.3(M + H)⁺Theory 750.28.

Example 16: synthesis of Compound 16

The synthesis procedure of compound 16 is similar to that of compound 1, intermediate 4 is selected as a reactant, and the yield is 79%; LC-MS M/Z actual measurement 791.3(M + H)⁺Theory 790.27.

Example 17: synthesis of Compound 17

Synthesis of Compound 17The synthesis steps are similar to those of the compound 1, the intermediate 7 is selected as a reactant, and the yield is 71%; LC-MS M/Z actual measurement 725.3(M + H)⁺Theory 724.26.

Example 18: synthesis of Compound 18

The synthesis procedure of compound 18 is similar to that of compound 1, intermediate 9 is selected as a reactant, and the yield is 75%; LC-MS M/Z actual measurement 675.2(M + H)⁺Theory 674.25.

Example 19: synthesis of Compound 19

The synthesis procedure of compound 19 is similar to that of compound 1, intermediate 10 is selected as a reactant, and the yield is 82%; LC-MS M/Z found 751.3(M + H)⁺Theory 750.28.

Device embodiments

As shown in fig. 1, the organic light emitting device (bottom-emitting OLED device) of the present invention includes a substrate 110, an anode 120, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Each layer of the organic light emitting device of the present invention can be formed by vacuum evaporation, sputtering, ion plating, or the like, or by wet film formation such as spin coating, printing, or the like, and the solvent used is not particularly limited.

Production of device examples 1-22:

on the surface or anode of ITO glass with the size of 2 mm multiplied by 2 mm, HT-1 and P-3 are co-evaporated or HT-1 is evaporated to form a Hole Injection Layer (HIL) with the thickness of 10nm (wherein, the volume ratio of HT-1 to P-3 is 97: 3), a Hole Transport Layer (HTL) with the thickness of 90 nm, then HT-10 is evaporated on the hole transport layer to form an Electron Blocking Layer (EBL) with the thickness of 10nm, then a host compound (BH-1) and a guest compound (BD-1) are co-evaporated on the electron blocking layer to form a light emitting layer (EML) (which can contain the compound of the invention) with the thickness of 25nm (wherein, the volume ratio of BH-1 to BD-1 is 97: 3), and finally the light emitting layer is formed by using the compound 1-19 of the invention: LiQ (where the volume ratio of the compounds 1 to 19 of the present invention to LiQ was 1:1) formed an Electron Transport Layer (ETL) of 35 nm, and then a cathode Al 40 nm was evaporated, thereby manufacturing an organic light emitting element.

Fabrication of comparative devices 1-6:

comparative devices 1-6 were fabricated similarly to device examples 1-22, except that corresponding comparative OLED devices were prepared using ET-1 through ET-6 (as the electron transport layer material) in comparative devices 1-6 in place of compounds 1-19 of the present invention.

The OLED devices of the invention and the comparative devices 1-6 were characterized by the same standard methods known in the art.

Table 1 shows the results of performance tests of the organic light-emitting devices in comparative devices 1 to 6 and device examples 1 to 19, in which LT95 lifetime was compared with the lifetime of comparative device 1 being 100%.

TABLE 1

。

Compared with the comparison device 1 (the material of the electron transport layer is ET-1), the electron transport materials adopted by the comparison devices 2-3 are ET-2 and ET-3, the electron transport materials have higher efficiency in the blue OLED device and also have longer service life which is 169 percent and 120 percent of that of the comparison device 1 respectively, but the operation voltages of the electron transport materials are higher and do not meet the requirement of the light-emitting device on low energy consumption, so that a compound is needed, after the electron transport materials are used, the voltage of the organic light-emitting device is equal to or reduced from that of the comparison device 1, and the efficiency and the service life are improved compared with that of the comparison device 1.

In comparative devices 4-6, the addition of benzene ring substitution in the triazine-substituted spirobifluorene system reduced the voltage of the devices compared to comparative devices 2-3, but the efficiency and lifetime were completely without advantage. On the basis, the pyridine group is introduced into the triazine substituted spirobifluorene system, and the invention unexpectedly finds that after the pyridine group is introduced (compound 1), the operation voltage of the device example 1 is equal to that of the comparative device 1, the service life is slightly poor, and the current efficiency is improved. Compared with pyridine on a spirobifluorene ring (a comparison device 2-3), the voltage of the organic light-emitting device in the comparison device 1 is reduced obviously, the efficiency is kept flat or slightly improved, but the service life is shorter than that of the comparison device 2-3. The operating voltages of the devices of examples 1 to 19 are all lower than those of the comparative devices 2 to 6, and are substantially equal to or slightly lower than those of the device of comparative device 1, but the efficiency of the device is greatly improved, and the service life of the device is remarkably prolonged, for example, in the device of example 18, the compound 18 is used as an electron transport layer material, the operating voltage of the device is reduced by 0.1 volt, the current efficiency of the device is improved by 10 percent, and the service life of the device is improved by 20 percent. The efficiency of the device in device example 12 was improved by 8%, but the lifetime was improved by 32%. Therefore, the spirobifluorene compound provided by the invention has pyridine and substituted triazine, so that the spirobifluorene compound is applied to an organic light-emitting device, and the efficiency and the service life of the device are improved while the operating voltage is reduced.

The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.