1. Has a formula Ir (L)_A)_n(L_B)_3-nA compound of (a), having the structure:

wherein A is¹、A²、A³、A⁴、A⁵、A⁶、A⁷And A⁸Each independently is carbon or nitrogen;

wherein A is¹、A²、A³、A⁴、A⁵、A⁶、A⁷And A⁸At least one of which is nitrogen;

wherein ring B is bonded to ring A via a C-C bond;

wherein iridium is bonded to ring a via an Ir-C bond;

wherein X is O, S or Se;

wherein R is¹、R³And R⁴Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;

wherein R is²Represents a mono-substituent, a di-substituent or no substituent;

wherein R is¹、R²、R³And R⁴Any adjacent substituents of (a) are optionally linked together to form a ring;

wherein R is¹、R²、R³、R⁴And R⁵Each independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein n is an integer from 1 to 3.

2. The compound of claim 1, wherein n is 1.

3. The compound of claim 1, wherein the compound has the formula:

4. the compound of claim 1, wherein a¹To A⁸Only one of which is nitrogen.

5. The compound of claim 1, wherein X is O.

6. According toThe compound of claim 1, wherein R¹、R³And R⁴Independently selected from the group consisting of: hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

7. The compound of claim 1, wherein R²Represents no substituent.

8. The compound of claim 1, wherein R²Represents a di-substituent and taken together to form a phenyl ring fused to ring B, and wherein the phenyl ring is optionally further substituted.

9. The compound of claim 1, wherein R⁵Is an alkyl or cycloalkyl group.

10. The compound of claim 1, wherein R⁵Is that

Wherein R is¹' and R²' each is independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein R is¹' and R²At least one of' is not hydrogen or deuterium; and

wherein ring C is a 5 or 6 membered carbocyclic or heterocyclic ring optionally further substituted.

11. The compound of claim 1, wherein the compound has a structure according to formula II:

wherein R is selected from the group consisting of: hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

12. The compound of claim 1, wherein L_ASelected from the group consisting of:

and

13. the compound of claim 12, wherein the compound has a structure selected from the group consisting of structure 1 through structure 16,362, wherein each structure x has the formula Ir (L)_Ak)_n(L_Bj)_3-nWhere x is 101j + k-101, k is an integer from 1 to 101, and j is an integer from 1 to 162, and where L_B1To L_B162The definition is as follows:

and

14. the compound of claim 1, wherein L_BSelected from the group consisting of:

and

15. a first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, the organic layer comprising Ir having the formula (L)_A)_n(L_B)_3-nA compound of (a), having the structure:

wherein A is¹、A²、A³、A⁴、A⁵、A⁶、A⁷And A⁸Each independently is carbon or nitrogen;

wherein A is¹、A²、A³、A⁴、A⁵、A⁶、A⁷And A⁸At least one of which is nitrogen;

wherein ring B is bonded to ring A via a C-C bond;

wherein iridium is bonded to ring a via an Ir-C bond;

wherein X is O, S or Se;

wherein R is¹、R³And R⁴Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;

wherein R is²Represents a mono-substituent, a di-substituent or no substituent;

wherein R is¹、R²、R³And R⁴Any adjacent substituents of (a) are optionally linked together to form a ring;

wherein R is¹、R²、R³、R⁴And R⁵Each independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein n is an integer from 1 to 3.

16. The first device of claim 15, wherein the first device is selected from the group consisting of: consumer products, electronic component modules, organic light emitting devices, and lighting panels.

17. The first device of claim 15, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

18. The first device of claim 15, wherein the organic layer further comprises a host; wherein the host comprises triphenylene comprising benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of: c_nH_2n+1、OC_nH_2n+1、OAr₁、N(C_nH_2n+1)₂、N(Ar₁)(Ar₂)、CH＝CH-C_nH_2n+1、C≡CC_nH_2n+1、Ar₁、Ar₁-Ar₂、C_nH_2n-Ar₁Or no substituent;

wherein n is 1 to 10; and

wherein Ar is₁And Ar₂Independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

19. The first device of claim 15, wherein the organic layer further comprises a host and the host is selected from the group consisting of:

and combinations thereof.

20. A formulation comprising Ir (L)_A)_n(L_B)_3-nThe compound of (1), said compound having the structure:

wherein A is¹、A²、A³、A⁴、A⁵、A⁶、A⁷And A⁸Each independently is carbon or nitrogen;

wherein A is¹、A²、A³、A⁴、A⁵、A⁶、A⁷And A⁸At least one of which is nitrogen;

wherein ring B is bonded to ring A via a C-C bond;

wherein iridium is bonded to ring a via an Ir-C bond;

wherein X is O, S or Se;

wherein R is¹、R³And R⁴Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;

wherein R is²Represents a mono-substituent, a di-substituent or no substituent;

wherein R is¹、R²、R³And R⁴Any adjacent substituents of (a) are optionally linked together to form a ring;

wherein R is¹、R²、R³、R⁴And R⁵Each independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein n is an integer from 1 to 3.

Background

Photovoltaic devices utilizing organic materials are becoming increasingly popular for a variety of reasons. Many of the materials used to make such devices are relatively inexpensive, and therefore organic photovoltaic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (such as their flexibility) may make them more suitable for particular applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include Organic Light Emitting Devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials. For example, the wavelength at which the organic emissive layer emits light can generally be readily tuned with appropriate dopants.

OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for applications such as flat panel displays, lighting, and backlighting. Several OLED materials and configurations are described in U.S. patent nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

One application of phosphorescent emissive molecules is in full color displays. Industry standards for such displays require pixels adapted to emit a particular color, known as a "saturated" color. In particular, these standards require saturated red, green, and blue pixels. Color can be measured using CIE coordinates well known in the art.

An example of a green emissive molecule is tris (2-phenylpyridine) iridium, which is denoted Ir (ppy)₃It has the following structure:

in this and the following figures herein, we depict the coordinate bond of nitrogen to metal (here Ir) in the form of a straight line.

As used herein, the term "organic" includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" may actually be quite large. In some cases, the small molecule may include a repeat unit. For example, the use of long chain alkyl groups as substituents does not remove a molecule from the "small molecule" class. Small molecules can also be incorporated into polymers, for example as pendant groups on the polymer backbone or as part of the backbone. Small molecules can also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and it is believed that all dendrimers currently used in the OLED art are small molecules.

As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed over" a second layer, the first layer is disposed farther away from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, there may be other layers between the first layer and the second layer. For example, a cathode may be described as being "disposed over" an anode even though various organic layers are present between the cathode and the anode.

As used herein, "solution processable" means in the form of a solution or suspension capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium.

A ligand may be referred to as "photoactive" when it is believed that the ligand contributes directly to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

As used herein, and as will be generally understood by those skilled in the art, a first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since Ionization Potential (IP) is measured as negative energy relative to vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO energy level corresponds to an Electron Affinity (EA) having a smaller absolute value (a less negative EA). On a conventional energy level diagram with vacuum levels at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. The "higher" HOMO or LUMO energy level appears closer to the top of this figure than the "lower" HOMO or LUMO energy level.

As used herein, and as will be generally understood by those skilled in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Since work function is typically measured as negative relative to vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram with vacuum level at the top, a "higher" work function is illustrated as being further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different rule than work functions.

More details regarding OLEDs and the definitions described above can be found in U.S. patent No. 7,279,704, which is incorporated herein by reference in its entirety.

Disclosure of Invention

According to one embodiment, a light emitting diode having the formula Ir (L)_A)_n(L_B)_3-nA compound of formula I having the structure of formula I:in the formula Ir (L)_A)_n(L_B)_3-nIn the structure of (1):

A¹、A²、A³、A⁴、A⁵、A⁶、A⁷and A⁸Each independently is carbon or nitrogen;

A¹、A²、A³、A⁴、A⁵、A⁶、A⁷and A⁸At least one of which is nitrogen;

ring B is bonded to ring A via a C-C bond;

iridium is bonded to ring a via an Ir-C bond;

x is O, S or Se;

R¹、R³and R⁴Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;

R²represents a mono-substituent, a di-substituent or no substituent;

R¹、R²、R³and R⁴Any adjacent substituents of (a) are optionally linked together to form a ring;

R¹、R²、R³、R⁴and R⁵Each independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

n is an integer of 1 to 3.

According to another embodiment, a device is also provided that includes one or more organic light emitting devices. At least one of the one or more organic light emitting devices may comprise an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise the formula Ir (L)_A)_n(L_B)_3-nA compound is provided. The device may be a consumer product, an electronic assembly module, an organic light emitting device and/or a lighting panel.

According to yet another embodiment, a formulation is provided comprising formula Ir (L)_A)_n(L_B)_3-nA compound is provided.

Drawings

Fig. 1 shows an organic light emitting device.

Fig. 2 shows an inverted organic light emitting device without a separate electron transport layer.

FIG. 3 shows formula Ir (L) as disclosed herein_A)_n(L_B)_3-n。

Detailed Description

Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and a hole are located on the same molecule, an "exciton," which is a localized electron-hole pair with an excited energy state, is formed. When the exciton relaxes via a light emission mechanism, light is emitted. In some cases, the exciton may be localized on an excimer or an excited complex. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.

The initial OLEDs used emissive molecules that emitted light from a singlet state ("fluorescence"), as disclosed, for example, in U.S. patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in a time frame of less than 10 nanoseconds.

More recently, OLEDs having emissive materials that emit light from the triplet state ("phosphorescence") have been demonstrated. Baldo (Baldo) et al, "high efficiency Phosphorescent Emission from Organic Electroluminescent Devices," Nature (Nature), 395 th volume, pages 151 to 154, 1998; ("Baldolo-I") and Bardolo et al, "Very high efficiency green organic light-emitting devices based on electrophosphorescence" (Very high-efficiency green organic light-emitting devices), applied Physics (appl. Phys. Lett.), Vol.75, No. 3, 4-6(1999) ("Baldolo-II"), which are incorporated herein by reference in their entirety. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704, columns 5 to 6, which is incorporated by reference.

Fig. 1 shows an organic light emitting device 100. The figures are not necessarily to scale. Device 100 can include substrate 110, anode 115, hole injection layer 120, hole transport layer 125, electron blocking layer 130, emissive layer 135, hole blocking layer 140, electron transport layer 145, electron injection layer 150, protective layer 155, cathode 160, and barrier layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704, columns 6 to 10, which is incorporated by reference.

More instances of each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:1₄TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes comprising composite cathodes having a thin layer of a metal (e.g., Mg: Ag) with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of barrier layers is described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

Fig. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. The device 200 may be fabricated by sequentially depositing the described layers. Because the most common OLED configuration has a cathode disposed above the anode and device 200 has a cathode 215 disposed below anode 230, device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in corresponding layers of device 200. Fig. 2 provides an example of how some layers may be omitted from the structure of device 100.

The simple layered structure illustrated in fig. 1 and 2 is provided by way of non-limiting example, and it should be understood that embodiments of the present invention can be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be realized by combining the various layers described in different ways, or several layers may be omitted entirely, based on design, performance and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it is understood that combinations of materials may be used, such as mixtures of hosts and dopants, or more generally mixtures. Further, the layer may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to fig. 1 and 2.

Structures and materials not specifically described may also be used, such as oleds (pleds) comprising polymeric materials, as disclosed in U.S. patent No. 5,247,190 to frand (Friend), et al, which is incorporated by reference in its entirety. As another example, an OLED having a single organic layer may be used. OLEDs can be stacked as described, for example, in U.S. patent No. 5,707,745 to florist (Forrest), et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling (out-coupling), e.g., a mesa structure as described in U.S. Pat. No. 6,091,195 to Flrister et al, and/or a recess structure as described in U.S. Pat. No. 5,834,893 to Boolean (Bulovic) et al, which are incorporated by reference in their entirety.

Any of the layers of the various embodiments may be deposited by any suitable method, unless otherwise specified. For organic layers, preferred methods include thermal evaporation, ink jetting (as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, both incorporated by reference in their entirety), organic vapor deposition (OVPD) (as described in U.S. Pat. No. 6,337,102 to Flrister et al, both incorporated by reference in their entirety), and deposition by Organic Vapor Jet Printing (OVJP) (as described in U.S. Pat. No. 7,431,968, both incorporated by reference in their entirety). Other suitable deposition methods include spin coating and other solution-based processes. The solution-based process is preferably carried out in a nitrogen or inert atmosphere. For other layers, a preferred method includes thermal evaporation. Preferred patterning methods include deposition via a mask, cold welding (as described in U.S. Pat. nos. 6,294,398 and 6,468,819, incorporated by reference in their entirety), and patterning associated with some of the deposition methods such as inkjet and OVJP. Other methods may also be used. The material to be deposited may be modified to make it compatible with a particular deposition process. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, can be used in small molecules to enhance the ability of the small molecule to undergo solution processing. Substituents having 20 carbons or more may be used, and 3 to 20 carbons is a preferred range. A material with an asymmetric structure may have better solution processibility than a material with a symmetric structure because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

Devices fabricated according to embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damage from exposure to harmful substances in the environment including moisture, vapor, and/or gas. The barrier layer may be deposited on, under or beside the substrate, electrode, or on any other part of the device, including the edge. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic compound or an organic compound or both. Preferred barrier layers comprise a mixture of polymeric and non-polymeric materials as described in U.S. patent No. 7,968,146, PCT patent application No. PCT/US2007/023098, and PCT/US2009/042829, which are incorporated herein by reference in their entirety. To be considered a "mixture," the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same reaction conditions and/or simultaneously. The weight ratio of polymeric material to non-polymeric material may be in the range of 95:5 to 5: 95. The polymeric material and the non-polymeric material may be produced from the same precursor material. In one example, the mixture of polymeric material and non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

Devices manufactured according to embodiments of the present invention may be incorporated into a wide variety of electronic component modules (or units), which may be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices (e.g., discrete light source devices or lighting panels), etc., which may be utilized by end-user product manufacturers. Such electronics module may optionally include drive electronics and/or a power source. Devices manufactured in accordance with embodiments of the present invention can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Such consumer products shall include any kind of product that contains one or more light sources and/or one or more of some type of visual display. Some examples of such consumer products include flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cell phones, tablet computers, tablet phones, Personal Digital Assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, large area walls, theater or stadium screens, or signs. Various control mechanisms may be used to control devices made in accordance with the present invention, including passive matrices and active matrices. Many of the devices are intended to be used in a temperature range that is comfortable for humans, such as 18 to 30 degrees celsius, and more preferably at room temperature (20 to 25 degrees celsius), but may be used outside this temperature range (e.g., -40 to +80 degrees celsius).

The materials and structures described herein may be applied to devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices such as organic transistors may employ the materials and structures.

As used herein, the term "halo", "halogen" or "halo" includes fluorine, chlorine, bromine and iodine.

As used herein, the term "alkyl" encompasses both straight-chain and branched-chain alkyl groups. Preferred alkyl groups are those containing one to fifteen carbon atoms and include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. In addition, the alkyl group may be optionally substituted.

As used herein, the term "cycloalkyl" encompasses cyclic alkyl groups. Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, and the like. In addition, cycloalkyl groups may be optionally substituted.

As used herein, the term "alkenyl" encompasses both straight-chain and branched-chain olefinic groups. Preferred alkenyl groups are those containing from two to fifteen carbon atoms. In addition, the alkenyl group may be optionally substituted.

As used herein, the term "alkynyl" encompasses both straight-chain and branched alkyne groups. Preferred alkynyl groups are those containing from two to fifteen carbon atoms. In addition, the alkynyl group may be optionally substituted.

As used herein, the terms "aralkyl" or "arylalkyl" are used interchangeably and encompass alkyl groups having an aromatic group as a substituent. In addition, the aralkyl group may be optionally substituted.

As used herein, the term "heterocyclyl" encompasses aromatic and non-aromatic cyclic groups. Aromatic heterocyclic groups are also intended to mean heteroaryl groups. Preferred non-aromatic heterocyclic groups are heterocyclic groups containing 3 or 7 ring atoms including at least one heteroatom and include cyclic amines such as morpholinyl, piperidinyl, pyrrolidinyl, and the like, and cyclic ethers such as tetrahydrofuran, tetrahydropyran, and the like. In addition, the heterocyclic group may be optionally substituted.

As used herein, the term "aryl" or "aromatic group" encompasses monocyclic groups and polycyclic ring systems. Polycyclic rings can have two or more rings in which two carbons are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. In addition, the aryl group may be optionally substituted.

As used herein, the term "heteroaryl" encompasses monocyclic heteroaromatic groups that can include one to three heteroatoms, such as pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, and pyrimidine, and the like. The term heteroaryl also includes polycyclic heteroaromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocycles and/or heteroaryls. In addition, heteroaryl groups may be optionally substituted.

The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl groups may be optionally substituted with one or more substituents selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, cyclic amino, silane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

As used herein, "substituted" means that a substituent other than H is bonded to the relevant position, such as carbon. Thus, for example, at R¹In the case of being monosubstituted, then one R¹Must not be H. Similarly, at R¹In the case of disubstituted, then two R¹Must not be H. Similarly, at R¹In the unsubstituted case, R¹Hydrogen for all available locations.

The "aza" designation in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more C-H groups in each fragment can be replaced by a nitrogen atom, e.g., and without any limitation, azatriphenylene encompasses dibenzo [ f, H ] quinoxaline and dibenzo [ f, H ] quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of skill in the art, and all such analogs are intended to be encompassed by the term as set forth herein.

It is understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different methods of naming substituents or attached fragments are considered equivalent.

According to one embodiment, a method is described having the formula Ir (L)_A)_n(L_B)_3-nOf the formula IThe structure of (1). In the formula Ir (L)_A)_n(L_B)_3-nIn the structure of (1):

A¹、A²、A³、A⁴、A⁵、A⁶、A⁷and A⁸Each independently is carbon or nitrogen;

A¹、A²、A³、A⁴、A⁵、A⁶、A⁷and A⁸At least one of which is nitrogen;

ring B is bonded to ring A via a C-C bond;

iridium is bonded to ring a via an Ir-C bond;

x is O, S or Se;

R¹、R³and R⁴Each independently represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent;

R²represents a mono-substituent, a di-substituent or no substituent;

R¹、R²、R³and R⁴Any adjacent substituents of (a) are optionally linked together to form a ring;

R¹、R²、R³、R⁴and R⁵Each independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

n is an integer of 1 to 3.

In some embodiments, R¹And R²Is cycloalkyl or includes alkyl having at least 2 carbon atoms, either of which may be fully or partially deuterated. In some embodiments, R¹And R²At least one of which is a cycloalkyl group or includes an alkyl group having at least 3 carbon atoms, either of which may beTo be fully or partially deuterated. In some embodiments, R¹And R²Is cycloalkyl or includes alkyl having at least 4 carbon atoms, either of which may be fully or partially deuterated.

In some embodiments, R¹、R²、R³And R⁴At least one set of adjacent substituents in (a) are linked together to form an aryl or heteroaryl ring. In some embodiments, R¹、R²、R³And R⁴At least one set of adjacent substituents in (a) are linked together to form a non-aryl ring.

In some embodiments, A₁-A₄And A₆-A₈Is carbon and A₅Is N.

In some embodiments, the compounds are homoleptic, while in other embodiments, the compounds are heteroleptic.

In some embodiments, n is 1, while in other embodiments, n is 2.

In some embodiments, the compound has the formula:

in some embodiments, A¹And A²Is C and A³And A⁴Bonded to Ir and ring B. In some embodiments, A¹To A⁸Only one of which is nitrogen. In some embodiments, A⁵To A⁸Is only one of nitrogen, and A¹To A⁴Is carbon. In some embodiments, X is O.

In some embodiments, R¹、R³And R⁴Independently selected from the group consisting of: hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

In some embodiments, R²Represents no substituent. In some embodiments, R²Represents a disubstituted group and linked together to form a phenyl ring fused to ring B, and wherein the phenyl ring is optionallyIs further substituted. In some embodiments, each position of the phenyl ring fused to ring B is substituted with a substituent independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In some embodiments, R⁵Is an alkyl or cycloalkyl group.

In some embodiments, R⁵Is thatWherein ring C is a 5 or 6 membered carbocyclic or heterocyclic ring optionally further substituted; and R is¹' and R²' each is independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof. In some embodiments, R¹' and R²At least one of' is not hydrogen or deuterium.

In some embodiments, each substitutable position of ring C may be substituted with a substituent independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof. In some embodiments, R¹' and R²At least one of' is not hydrogen or deuterium.

In some embodiments, R¹' and R²' each is independently selected from the group consisting of: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2-dimethylpropyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, partially or fully deuterated variants thereof, and combinations thereof.

In some embodiments, the compound has a structure according to formula II:formula II. In the structure of formula II, R is selected from the group consisting of: hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof. In some embodiments of formula II, R is selected from the group consisting of: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2-dimethylpropyl, cyclopentyl, cyclohexyl, partially or fully deuterated versions thereof, and combinations thereof.

In some embodiments, L_ASelected from the group consisting of:

and

in some embodiments, L_BSelected from the group consisting of:

and

in some embodiments, the compound has a structure selected from the group consisting of structure 1 through structure 16,362, wherein each structure x has the formula Ir (L)_Ak)(L_Bj)₂Where x is 101j + k-101, k is an integer from 1 to 101, and j is an integer from 1 to 162, and where L_A1To L_A101And L_B1To L_B162Having the meaning as provided above.

In some embodiments, the compound may be an emissive dopant. In some embodiments, the compounds may produce emission via phosphorescence.

According to another aspect of the present invention, there is also provided a device comprising one or more organic light emitting devices. At least one of the one or more organic light emitting devices may include an anode; a cathode; and an organic layer disposed between the anode and the cathode. The organic layer may include a host and a phosphorescent dopant. The emissive layer may comprise a material according to formula M (L) as described herein_A)_n(L_B)_3-nAnd variations thereof.

The device may be one or more of a consumer product, an electronic component module, an organic light emitting device, and a lighting panel. The organic layer may be an emissive layer, and the compound may be an emissive dopant in some embodiments, while the compound may be a non-emissive dopant in other embodiments.

The organic layer may further include a host. In some embodiments, the body may include a metal complex. The host may be triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the subject may be an unfused substituent independently selected from the group consisting of: c_nH_2n+1、OC_nH_2n+1、OAr₁、N(C_nH_2n+1)₂、N(Ar₁)(Ar₂)、CH＝CH-C_nH_2n+1、C≡C-C_nH_2n+1、Ar₁、Ar₁-Ar₂And C_nH_2n-Ar₁Or no substituent. In the foregoing substituents, n may vary from 1 to 10; and Ar₁And Ar₂May be independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

The host may be a compound comprising at least one chemical group selected from the group consisting of: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. The body may include a metal complex. The host may be a specific compound selected from the group consisting of:

and combinations thereof.

In yet another aspect of the invention, a formulation is described comprising a compound according to formula M (L)_A)_n(L_B)_3-nThe compound of (1). The formulation may include one or more of the components disclosed herein selected from the group consisting of: a solvent, a host, a hole injection material, a hole transport material, and an electron transport layer material.

In combination with other materials

Materials described herein as suitable for use in a particular layer in an organic light emitting device can be used in combination with a wide variety of other materials present in the device. For example, the emissive dopants disclosed herein may be used in conjunction with a wide variety of host, transport, barrier, implant, electrode, and other layers that may be present. The materials described or referenced below are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one of ordinary skill in the art can readily review the literature to identify other materials that can be used in combination.

HIL/HTL：

The hole injecting/transporting material used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of materials include (but are not limited to): phthalocyanine or porphyrin derivatives; an aromatic amine derivative; indolocarbazole derivatives; a fluorocarbon-containing polymer; a polymer having a conductive dopant; conductive polymers such as PEDOT/PSS; self-assembling monomers derived from compounds such as phosphonic acids and silane derivatives; metal oxide derivatives, e.g. MoO_x(ii) a p-type semiconducting organic compounds, such as 1,4,5,8,9, 12-hexaazatriphenylhexacyano-nitrile; a metal complex; and a crosslinkable compound.

Examples of aromatic amine derivatives for use in the HIL or HTL include, but are not limited to, the following general structures:

and

Ar¹to Ar⁹Each of which is selected from: groups consisting of cyclic compounds of aromatic hydrocarbons, e.g. benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene,Perylene and azulene; by aromatic heterocyclesA group composed of compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, benzoselenenopyridine, and selenophenobipyridine; and a group composed of 2 to 10 cyclic structural units which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Wherein each Ar is further substituted with a substituent selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, Ar¹To Ar⁹Independently selected from the group consisting of:

and

wherein k is an integer from 1 to 20; x¹⁰¹To X¹⁰⁸Is C (including CH) or N; z¹⁰¹Is NAr¹O or S; ar (Ar)¹Having the same groups as defined above.

Examples of metal complexes used in HILs or HTLs include, but are not limited to, the following general formulas:

wherein Met is a metal which may have an atomic weight greater than 40; (Y)¹⁰¹-Y¹⁰²) Is a bidentate ligand, Y¹⁰¹And Y¹⁰²Independently selected from C, N, O, P and S; l is¹⁰¹Is an ancillary ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k' + k "is the maximum number of ligands that can be attached to the metal.

In one aspect, (Y)¹⁰¹-Y¹⁰²) Is a 2-phenylpyridine derivative. In another aspect, (Y)¹⁰¹-Y¹⁰²) Is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In another aspect, the metal complex has a relative Fc to Fc⁺A minimum oxidation potential in solution of less than about 0.6V for/Fc coupling.

A main body:

the light-emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as a light-emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is larger than that of the dopant. Although the following table classifies the host material as preferred for devices emitting various colors, any host material may be used with any dopant so long as the triplet criteria are met.

Examples of the metal complex used as the host preferably have the following general formula:

wherein Met is a metal; (Y)¹⁰³-Y¹⁰⁴) Is a bidentate ligand, Y¹⁰³And Y¹⁰⁴Independently selected from C, N, O, P and S; l is¹⁰¹Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal; and k' + k "is the maximum number of ligands that can be attached to the metal.

In one aspect, the metal complex is:

wherein (O-N) is a bidentate ligand having a metal coordinated to the O and N atoms.

In another aspect, Met is selected from Ir and Pt. In another aspect, (Y)¹⁰³-Y¹⁰⁴) Is a carbene ligand.

Examples of organic compounds used as hosts are selected from: groups consisting of cyclic compounds of aromatic hydrocarbons, e.g. benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene,Perylene and azulene; groups composed of aromatic heterocyclic compounds, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzoselenophenselenophene, benzoselenophene selenopheneAnd pyrido and selenopheno bipyridine; and a group composed of 2 to 10 cyclic structural units which are groups of the same type or different types selected from aromatic hydrocarbon ring groups and aromatic heterocyclic groups and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an aliphatic ring group. Wherein each group is further substituted with a substituent selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, the host compound contains in the molecule at least one of the following groups:

and

wherein R is¹⁰¹To R¹⁰⁷Independently selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, which when aryl or heteroaryl has a similar definition to Ar mentioned above. k is an integer from 0 to 20 or 1 to 20; k' "is an integer of 0 to 20. X¹⁰¹To X¹⁰⁸Selected from C (including CH) or N. Z¹⁰¹And Z¹⁰²Selected from NR¹⁰¹O or S.

HBL：

A Hole Blocking Layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a barrier layer in the device may result in substantially higher efficiency compared to a similar device lacking a barrier layer. In addition, a blocking layer can be used to limit the emission to the desired area of the OLED.

In one aspect, the compound used in the HBL contains the same molecule or the same functional group as used as the host described above.

In another aspect, the compound used in the HBL contains in the molecule at least one of the following groups:

wherein k is an integer from 1 to 20; l is¹⁰¹Is another ligand, and k' is an integer of 1 to 3.

ETL：

The Electron Transport Layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complex or organic compound may be used as long as it is typically used to transport electrons.

In one aspect, the compound used in the ETL contains in the molecule at least one of the following groups:

wherein R is¹⁰¹Selected from the group consisting of: hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid group, carboxyl, amino, carboxyl, amino, carboxyl, amino, carbonyl, amino, carboxyl, or amino,Ester groups, nitrile groups, isonitrile groups, thio groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, which when aryl or heteroaryl have similar definitions as those mentioned above for Ar. Ar (Ar)¹To Ar³Have similar definitions as Ar mentioned above. k is an integer of 1 to 20. X¹⁰¹To X¹⁰⁸Selected from C (including CH) or N.

In another aspect, the metal complexes used in the ETL include (but are not limited to) the following general formula:

wherein (O-N) or (N-N) is a bidentate ligand having a metal coordinated to atom O, N or N, N; l is¹⁰¹Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.

In any of the above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any specifically listed substituent, such as (but not limited to) methyl, phenyl, pyridyl, and the like, encompasses non-deuterated, partially deuterated, and fully deuterated forms thereof. Similarly, substituents in the class such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, and the like also encompass non-deuterated, partially deuterated, and fully deuterated forms thereof.

Many hole injection materials, hole transport materials, host materials, dopant materials, exciton/hole blocking layer materials, electron transport, and electron injection materials can be used in OLEDs in addition to and/or in combination with the materials disclosed herein. Non-limiting examples of materials that can be used in OLEDs in combination with the materials disclosed herein are listed in table a below. Table a lists non-limiting classes of materials, non-limiting examples of compounds of each class, and references disclosing the materials.

TABLE A

Experiment of

Synthesis examples:

synthesis of Compound 46(Ir (L)_A46)(L_B1)₂)

_A46Synthesis of Compound 46(Ir (L)) _B1(L) ₂)：

Benzimidazole ligand (1.85g, 4.33mmol) and iridium complex (1.85g, 2.59mmol) were charged to a reaction flask with 30mL DMF and 30mL 2-ethoxyethanol. This mixture was degassed with nitrogen and then heated in an oil bath set at 130 ℃ for 2 days. The reaction mixture was concentrated and then dried under vacuum. This crude product was dissolved in 300mL of DCM, which was then passed through a plug of silica gel. Fractions containing the desired product were combined and concentrated in vacuo. This crude residue was passed through a silica gel column using 65% to 80% DCM/heptane. The clean product fractions were combined and concentrated in vacuo to yield 0.9g of Compound 46(Ir (L)_A46)(L_B1)₂)。

Example of the apparatus:

all example devices were passed through high vacuum: (<10^-7Torr) thermal evaporation. The anode electrode isIndium Tin Oxide (ITO). Cathode made ofAfter LiF is connectedAnd Al. After fabrication, all devices were immediately encapsulated in a nitrogen glove box with epoxy-sealed glass lids ((R))<1ppm of H₂O and O₂) And incorporating a moisture getter into the package interior. The organic stack of the device example consists of an ITO surface,LG101 as a Hole Injection Layer (HIL),Compound D (as a Hole Transport Layer (HTL)), (ii) and (iii) a salt thereof,A compound of the invention doped in a compound B (as host) and 10 or 15 weight percent of an iridium phosphorescent compound (compound 46) (as emissive layer (EML)),compound C as a Barrier Layer (BL)), (as a barrier layer(s),Alq (tris-8-hydroxyquinolinylaluminum) (as ETL). Comparative examples with compound a were made in a similar manner to the device examples. The device results and data are summarized in tables 1 and 2. As used herein, Alq, compound A, B, C, and D have the following structures:

TABLE 1 device Structure of inventive and comparative Compounds

Table 2VTE device results

Table 2 is a summary of EL for the comparative and inventive devices at 1000 nits. For compound a of comparative examples 1 and 2 at dopant concentrations of 10% and 15%, the EQE values at 1000 nits were 18.9% and 17.7%, respectively, relative to 22.3% and 22.8% of compound 46 of device examples 1 and 2 at dopant concentrations of 10% and 15%, respectively. Similar EQE results were observed at 9000 nits. These device results show that the aza-DBF containing complexes show better device performance than the standard DBF containing complexes according to EQE.

It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. The invention as claimed may thus comprise variations of the particular examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that various theories as to why the invention works are not intended to be limiting.