JP7618938B2 - Organic electroluminescent materials and devices - Google Patents

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application No. 62/850,800, filed May 21, 2019, the disclosure of which is incorporated herein by reference in its entirety.

This disclosure relates generally to organometallic compounds and compositions and their various uses, including as light emitters in devices such as organic light emitting diodes and related electronic devices.

Optoelectronic devices that utilize organic materials are becoming increasingly desirable for a variety of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as flexibility, may make them well suited for certain applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over conventional materials.

OLEDs use thin organic films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting and backlighting.

One application of phosphorescent emissive molecules is full color displays. Industry standards for such displays require pixels adapted to emit specific colors, referred to as "saturated" colors. In particular, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. Conventional liquid crystal display emission from a white backlight is filtered with absorbing filters to produce red, green, and blue emission. Similar techniques can be used with OLEDs. White OLEDs can be either single emissive layer (EML) devices or stack structures. Color can be measured using CIE coordinates, which are well known in the art.

Transition metal compounds having naphthylene-aryl bidentate ligands that are rigid and conjugated moieties are disclosed. Such transition metal complexes are useful as emitter materials in organic electroluminescent devices.

In one aspect, the present disclosure provides a compound comprising a first ligand L 1 _A of formula 1:
wherein each X ¹ -X ¹⁰ is C or N; the maximum number of N of X ¹ -X ¹⁰ in the same ring is 3; R ^A and R ^B each represent the maximum allowable substitution from mono or no substitution; L _A is complexed with a metal M; each R ^A and R ^B is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; M can be coordinated with other ligands; said ligand L _A can be combined with other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be bonded or fused together to form a ring.

In another aspect, the present disclosure provides a composition of the disclosed compounds.

In yet another aspect, the present disclosure provides an OLED having an organic layer comprising a compound of the present disclosure.

In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a compound of the present disclosure.

FIG. 1 shows an organic light emitting device.

FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.

FIG. 3 shows a photoluminescence (PL) spectrum of the present invention example compound I-A34 obtained in a 2-methyl THF solution at room temperature.

A. Terminology Unless otherwise stated, the following terms used herein are defined as follows.

As used herein, the term "organic" includes polymeric and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" can actually be quite large. Small molecules can include repeat units in some circumstances. For example, the use of long chain alkyl groups as a substituent does not remove a molecule from the "small molecule" class. Small molecules can be incorporated into polymers, for example, as pendant groups on a 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 can be a fluorescent or phosphorescent small molecule emitter. Dendrimers can be "small molecules," and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

As used herein, "top" means furthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as "disposed over" a second layer, the first layer is disposed further from the substrate. There may be other layers between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode may be described as "disposed over" an anode, even though there may be various organic layers in between.

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

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

As used herein, and as 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. Because ionization potentials (IPs) are measured as negative energies relative to the vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (a less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (a less negative EA). In a conventional energy level diagram with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears to be closer to the top of such a diagram than a "lower" HOMO or LUMO energy level.

As used herein, as 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 functions are generally measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. In a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being further away from the vacuum level in a downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.

The terms "halo", "halogen" and "halide" are used interchangeably and refer to fluorine, chlorine, bromine and iodine.

The term "acyl" refers to a substituted carbonyl group (C(O)-- _R.sub.s ).

The term "ester" refers to a substituted oxycarbonyl (--O--C(O)-- _R.sub.s or --C(O)--O-- _R.sub.s ) group.

The term "ether" refers to the group -OR _s .

The terms "sulfanyl" and "thioether" are used interchangeably and refer to the group _--SR.sub.s .

The term "sulfinyl" refers to the group -S(O) _-Rs .

The term "sulfonyl" refers to the group -SO _{2 -Rs} .

The term "phosphino" refers to the group --P( _R.sub.s ) _.sub.3 , where each _R.sub.s can be the same or different.

The term "silyl" refers to the group --Si( _R.sub.s ) _.sub.3 , where each _R.sub.s can be the same or different.

The term "boryl" refers to the group --B( _R.sub.s ) _.sub.2 , or its Lewis adduct, --B( _R.sub.s ) _.sub.3 , where _R.sub.s can be the same or different.

In each of the above, _Rs can be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. Preferred _Rs are selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

The term "alkyl" refers to and includes both straight and branched chain alkyl groups. Preferred alkyl groups contain from 1 to 15 carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, and 2,2-dimethylpropyl. Additionally, the alkyl groups may be optionally substituted.

The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl groups may be optionally substituted.

The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Furthermore, the heteroalkyl or heterocycloalkyl group may be optionally substituted.

The term "alkenyl" refers to and includes both straight and branched chain alkene groups. Alkenyl groups are essentially alkyl groups containing at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl groups are essentially cycloalkyl groups containing at least one carbon-carbon double bond in the cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group having at least one carbon atom replaced by a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Preferred alkenyl, cycloalkenyl, or heteroalkenyl groups are those containing 2 to 15 carbon atoms. Additionally, said alkenyl, said cycloalkenyl, or said heteroalkenyl groups may be optionally substituted.

The term "alkynyl" refers to and includes both straight-chain and branched-chain alkyne groups. An alkynyl group is essentially an alkyl group that contains at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those that contain 2 to 15 carbon atoms. Additionally, said alkynyl groups may be optionally substituted.

The terms "aralkyl" and "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. Additionally, the aralkyl group may be optionally substituted.

The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Heteroaromatic cyclic groups may be used interchangeably with heteroaryl. Preferred heteronon-aromatic cyclic groups are those containing 3-7 ring atoms and contain at least one heteroatom, including cyclic amines such as morpholino, piperidino, pyrrolidino, and cyclic ethers/thioethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Additionally, the heterocyclic groups may be optionally substituted.

The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. A polycyclic ring can have two or more rings with two carbons shared between two adjacent rings (the rings are "fused"), at least one of the rings being an aromatic hydrocarbyl group, and the other rings can be, for example, a cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Preferred aryl groups are those containing 6 to 30 carbon atoms, preferably those containing 6 to 20 carbon atoms, and more preferably those containing 6 to 12 carbon atoms. Aryl groups having 6 carbons, 10 carbons, or 12 carbons are particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, and are preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Furthermore, the aryl group may be optionally substituted.

The term "heteroaryl" refers to and includes both monocyclic aromatic groups and polycyclic aromatic ring systems that contain at least one heteroatom. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many instances, O, S, or N are the preferred heteroatoms. Heteromonocyclic aromatic systems are preferably monocyclic rings having 5 or 6 ring atoms, and the rings can have 1 to 6 heteroatoms. Heteropolycyclic ring systems can have two or more rings in which two atoms are common to two adjacent rings (the rings are "fused"), and at least one of the rings is heteroaryl, and the other rings can be, for example, cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Heteropolycyclic aromatic ring systems can have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those that contain 3 to 30 carbon atoms, preferably those that contain 3 to 20 carbon atoms, and more preferably those that contain 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benziso ... Examples of the heteroaryl group include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza analogs thereof. Furthermore, the heteroaryl group may be optionally substituted.

Of the aryl and heteroaryl groups listed above, the triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole groups, and their respective aza analogues, are of particular interest.

As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic, aryl, and heteroaryl are independently unsubstituted or independently substituted with one or more common substituents.

In many instances, the typical substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.

In some examples, preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof.

In some examples, more preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and combinations thereof.

In yet other examples, the most preferred common substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

The terms "substituted" and "substitution" refer to a substituent other than H attached to the relevant position (e.g., carbon or nitrogen). For example, if R ¹ represents monosubstitution, one R ¹ must be other than H (i.e., substituted). Similarly, if R 1 represents disubstitution ^, two of R ¹ must be other than H. Similarly, if R ¹ represents zero or no substitution, R ¹ can be hydrogen at the available valence of the ring atom, as in the case of carbon atoms in benzene and nitrogen atoms in pyrrole, or simply nothing in the case of ring atoms with fully filled valences (e.g., nitrogen in pyridine). The maximum number of substitutions possible in a ring structure depends on the total number of available valences at the ring atoms.

As used herein, "combinations thereof" refers to one or more members of the applicable list being combined to form a known or chemically stable configuration that one of skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group; halogen and alkyl can be combined to form a halogenated alkyl substituent; halogen, alkyl, and aryl can be combined to form a halogenated aryl alkyl. In one example, the term substituted includes combinations of 2-4 of the listed groups. In another example, the term substituted includes combinations of 2-3 groups. In yet another example, the term substituted includes combinations of 2 groups. Preferred combinations of substituents include those that contain up to 50 atoms that are not hydrogen or deuterium, or those that contain up to 40 atoms that are not hydrogen or deuterium, or those that contain up to 30 atoms that are not hydrogen or deuterium. In many examples, preferred combinations of substituents include up to 20 atoms that are not hydrogen or deuterium.

The designation "aza" in the fragments described herein, e.g., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C-H groups in each aromatic ring can be replaced by a nitrogen atom, e.g., but without any limitation, azatriphenylene includes both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of skill in the art can easily imagine other nitrogen analogs of the above aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Pat. No. 8,557,400, International Publication No. WO 2006/095951, and U.S. Patent Application Publication No. 2011/0037057, the contents of which are incorporated by reference in their entireties, describe the preparation of deuterium-substituted organometallic complexes. Further references include Tetrahedron 2015, 71, 1425-30 (Ming Yan et al.) and Angew. Chem. Int. Ed., the contents of which are incorporated by reference in their entireties. (Reviews) 2007, 46, 7744-65 (Atzrodt et al.), which describes efficient routes for deuteration of methylene hydrogens in benzylamines and replacement of aromatic ring hydrogens with deuterium, respectively.

When a molecular fragment is described as being a substituent or attached to another moiety, it is understood that the name may be described as being the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). Different designations of the substituents or attached fragments are considered equivalent herein.

In some cases, the adjacent substituents of a pair can be optionally bonded or fused to form a ring. Preferred rings are 5-, 6-, or 7-membered carbocyclic or heterocyclic rings, including both cases where the portion of the ring formed by the pair of substituents is saturated and cases where the portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two related substituents can be on the same ring adjacent to each other, or on the two adjacent rings with the two nearest available substitutable positions, such as 2- and 2'-positions in biphenyl and 1- and 8-positions in naphthalene, as long as a stable fused ring system can be formed.
B. Compounds of the Disclosure

In one aspect, the present disclosure provides a compound comprising a first ligand L 1 _A of formula 1:
wherein each X ¹ -X ¹⁰ is C or N; the maximum number of N of X ¹ -X ¹⁰ in the same ring is 3; R ^A and R ^B each represent the maximum allowable substitution from mono or no substitution; L _A is complexed with a metal M; each R ^A and R ^B is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; M can be coordinated with other ligands; said ligand L _A can be combined with other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be bonded or fused together to form a ring.

In some embodiments of the compounds, each R ^A and R ^B is independently hydrogen or a substituent selected from the group of preferred general substituents defined herein.

In some embodiments, M is selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au. In some embodiments, M is Pt. In embodiments where M is Pt, the first ligand L _A can be combined with one or two other ligands to form a tridentate or tetradentate ligand.

In some embodiments, at least one of R ^A and R ^B is a 5- or 6-membered heterocycle. In some embodiments, at least one of R ^A and R ^B is selected from the group consisting of pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, and N-heterocyclic carbene.

In some embodiments, at least one of X ¹ -X ¹⁰ is N. In some embodiments, X ³ is N. In some embodiments, X ³ is N and the remainder of X ¹ -X ¹⁰ are C. In some embodiments, each of X ¹ -X ¹⁰ is C. In some embodiments, two R ^A substituents are bonded together to form a 6-membered carbocyclic or heterocyclic ring. In some embodiments, two or more R ^B substituents are bonded together to form one or more 6-membered carbocyclic or heterocyclic rings.

In some embodiments of the compound, the compound is a compound of formula 2:
In the formula, M is Pd or Pt; Ring C and Ring D are each independently a 5- or 6-membered carbocyclic or heterocyclic ring; Z ¹ and Z ² are each independently C or N; W ¹ and W ² are each independently C or N; R ^C and R ^D are each independently mono to maximum allowable substitution or no substitution; L ¹ , L ² and L ³ are each independently a 1-atom or 2-atom linker or a direct bond; m, n and p are each independently 0 or 1; m + n + p = 2 or 3; each R ^C and R ^D is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; any two substituents can be bonded or fused together to form a ring. In some embodiments, each R ^C and R ^D is independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein. In some embodiments, p=0 and ^L1 and ^L2 are each independently selected from the group consisting of a direct bond, O, S, CRR', SiRR', BR, and NR; each R and R' is independently hydrogen or a substituent selected from the group of general substituents defined herein. In some embodiments, each R and R' is independently hydrogen or a substituent selected from the group of preferred general substituents defined herein.

In some embodiments of the compound, the compound is selected from the group consisting of:
wherein A ¹ -A ¹⁰ are each independently C or N, and the maximum number of N atoms in the same ring is 3; X ¹¹ -X ¹⁴ have the same definition as X ¹ -X ¹⁰ ; R ^E and R ^F have the same definition as R ^C and R ^D ; L ⁴ represents a linker; R ^X and R ^Y are each independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; and any two substituents can be bonded or fused together to form a ring.

In some embodiments of the compound, the compound is selected from the group consisting of:
wherein i is an integer from 1 to 2000, and for each i, R ¹ , R ² , R ³ , R ⁴ , Y ¹ , and Y ² in Formulas I-LVIII are defined as follows:
wherein R ^A1 to R ^A53 have the following structures:
R ^B1 to R ^B46 have the following structures:
R ^C1 to R ^C292 have the following structures:

In some embodiments of the compound, the compound is selected from the group consisting of:
C. OLEDs and Devices of the Present Disclosure

In another aspect, the present disclosure also provides an OLED device comprising a first organic layer containing a compound disclosed in the Compounds section of the present disclosure.

In some embodiments, an OLED includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer can include a compound including a first ligand L _A of Formula 1:
wherein each X ¹ -X ¹⁰ is C or N; the maximum number of N of X ¹ -X ¹⁰ in the same ring is 3; R ^A and R ^B each represent the maximum allowable substitution from mono or no substitution; L _A is complexed with a metal M; each R ^A and R ^B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; M can be coordinated with other ligands; said ligand L _A can be linked to other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be linked or fused together to form a ring.

In some embodiments, the organic layer can be an emissive layer, and the compounds described herein can be emissive or non-emissive dopants.

In some embodiments, the organic layer can further comprise a host, the host comprising a triphenylene, including a benzo-fused thiophene or a benzo-fused furan, any substituent in the host can be independently a non-fused substituent selected from the group consisting of C _n H _2n+1 , OC _n H _2n+1 , OAr ₁ , N(C _n H _2n+1 ) ₂ , N(Ar ₁ )(Ar ₂ ), CH═CH—C _n H _2n+1 , C≡C—C _n H _2n+1 , Ar ₁ , Ar ₁ -Ar ₂ , C _n H _2n -Ar ₁ or unsubstituted, where n is 1 to 10, and Ar ₁ and Ar ₂ can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

In some embodiments, the organic layer may further include a host, the host including at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boronaphtho[3,2,1-de]anthracene).

In some embodiments, the host may be selected from the group of hosts selected from the group consisting of:

In some embodiments, the organic layer can further include a host, the host including a metal complex.

In some embodiments, the compounds described herein can be sensitizers and the device can further include an acceptor, which can be selected from fluorescent emitters, delayed fluorescent emitters, and combinations thereof.

In yet another aspect, the OLED of the present disclosure can also include a light-emitting region that includes a compound disclosed in the Compounds section of the present disclosure.

In some embodiments, the emissive region can include a compound that includes a first ligand L 1 _A of Formula 1:
wherein each X ¹ -X ¹⁰ is C or N; the maximum number of N of X ¹ -X ¹⁰ in the same ring is 3; R ^A and R ^B each represent the maximum allowable substitution from mono or no substitution; L _A is complexed with a metal M; each R ^A and R ^B is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; M can be coordinated with other ligands; said ligand L _A can be combined with other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be bonded or fused together to form a ring.

In yet another aspect, the present disclosure also provides a consumer product comprising an organic light emitting device (OLED) having an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound disclosed in the Compounds section of the present disclosure.

In some embodiments, the consumer product comprises an OLED having an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer can comprise a compound comprising a first ligand L _A of Formula 1:
wherein each X ¹ -X ¹⁰ is C or N; the maximum number of N of X ¹ -X ¹⁰ in the same ring is 3; R ^A and R ^B each represent the maximum allowable substitution from mono or no substitution; L _A is complexed with a metal M; each R ^A and R ^B is independently hydrogen or a substituent selected from the group consisting of general substituents defined herein; M can be coordinated with other ligands; said ligand L _A can be combined with other ligands to include tridentate, tetradentate, pentadentate, or hexadentate ligands; any two substituents can be bonded or fused together to form a ring.

In some embodiments, the consumer product can be one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor illumination and/or signaling, a head-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays aligned together, a theater or stadium screen, a light therapy device, and a sign.

In general, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons migrate to the oppositely charged electrode, respectively. When an electron and hole localize on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. Light is emitted via a photoemissive mechanism when the exciton relaxes. In some cases, the exciton may be localized on an excimer or exciplex. Nonradiative mechanisms such as thermal relaxation can also occur, but are generally considered undesirable.

Some OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated by reference in their entireties.

Early OLEDs used emissive molecules that emitted light from their singlet state ("fluorescence"), as disclosed, for example, in U.S. Pat. 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 triplet states ("phosphorescence") have been demonstrated. See Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, Vol. 395, pp. 151-154, 1998; ("Baldo-I") and Baldo et al., "Very high-efficiency green organic light emitting devices based on electrophosphorescence," Appl. Phys. Lett., 1998, pp. 151-154, 1998, all of which are incorporated by reference in their entireties. 75, No. 3, 4-6 (1999) ("Baldo-II"). Phosphorescence is described in further detail in U.S. Pat. No. 7,279,704, columns 5-6, which are incorporated by reference.

Figure 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. The cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in US 7,279,704, columns 6-10, which are incorporated by reference.

Further examples are available for each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F ₄ -TCNQ in a 50:1 molar ratio 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 in a 1:1 molar ratio as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The theory and use of blocking layers are 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 protective layers can be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

Figure 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. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has the cathode disposed above the anode, and device 200 has the cathode 215 disposed below the 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 the corresponding layers of device 200. Figure 2 provides an example of how some layers may be omitted from the structure of device 100.

The simple layer structures illustrated in Figures 1 and 2 are provided as non-limiting examples, and it is understood that embodiments of the present disclosure may be used in conjunction with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. A functional OLED may be achieved by combining the various layers described in various ways, or 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. While many of the examples provided herein describe the various layers as including a single material, it is understood that combinations of materials, such as mixtures of hosts and dopants, or more generally mixtures, may be used. Layers may also have various sublayers. 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. The organic layer may include a single layer, or may further include multiple layers of different organic materials, such as those described with respect to Figures 1 and 2.

Structures and materials not specifically described may be used, such as OLEDs (PLEDs) composed of polymeric materials such as those disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. As a further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example, as described in U.S. Pat. No. 5,707,745 to Forrest et al., which is incorporated by reference in its entirety. OLED structures may deviate from the simple layered structures illustrated in FIGS. 1 and 2. For example, the substrate may include angled reflective surfaces to improve outcoupling, such as the mesa structures described in U.S. Pat. No. 6,091,195 to Forrest et al. and/or the recessed structures described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entirety.

Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include deposition by thermal evaporation, such as those described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entirety, inkjet, organic vapor phase deposition (OVPD), such as that described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and organic vapor jet printing (OVJP), such as that described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include patterning associated with some of the deposition methods such as deposition via mask, cold welding, and inkjet and organic vapor jet printing (OVJP), such as those described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety. Other methods may be used. The material to be deposited may be modified to be compatible with the particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents with 20 or more carbons may be used, with 3-20 carbons being a preferred range. Materials with asymmetric structures may have better solution processability than those with symmetric structures, since asymmetric materials may be less prone to recrystallization. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

Devices fabricated according to embodiments of the present disclosure may further include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment, including moisture, vapors and/or gases. The barrier layer may be deposited on, under or next to the substrate, the electrodes, or on any other portion of the device, including the edges. The barrier layer may include 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 and compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferred barrier layers include mixtures of polymeric and non-polymeric materials, as described in U.S. Pat. No. 7,968,146, PCT Patent Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are incorporated herein by reference in their entireties. To be considered a "mixture," the polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or simultaneously. The weight ratio of polymeric to non-polymeric materials can be in the range of 95:5 to 5:95. The polymeric and non-polymeric materials can be made from the same precursor materials. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.

Devices made according to embodiments of the present disclosure can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into various electrical products or intermediate components. Such electrical products or intermediate components include display screens, lighting devices (such as discrete light source devices or lighting panels) that can be utilized by end-user product manufacturers. Such electronic component modules can optionally include driving electronics and/or power sources. Devices made according to embodiments of the present disclosure can be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Disclosed are consumer products that include OLEDs that include compounds of the present disclosure in the organic layer of the OLED. Such consumer products include any type of product that includes one or more light sources and/or one or more visual displays of some kind. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cell phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays aligned together, theater or stadium screens, phototherapy devices, and signage. A variety of control mechanisms, including passive matrix and active matrix, can be used to control devices made according to the present disclosure. Many of the devices are intended for use within a temperature range that is comfortable for humans, such as 18 degrees Celsius to 30 degrees Celsius, and more preferably room temperature (20-25° C.), but may also be used outside this temperature range, for example, −40 degrees Celsius to +80 degrees Celsius.

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

The materials and structures described herein may have application in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. More generally, organic devices such as organic transistors may use the materials and structures.

In some embodiments, the OLED has one or more properties selected from the group consisting of being flexible, rollable, foldable, stretchable, and bendable. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED comprises an RGB pixel array or a white and color filter pixel array. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is a lighting panel.

In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, or TADF (also called E-type delayed fluorescence; see, e.g., U.S. Application No. 15/700,352, incorporated by reference in its entirety), triplet-triplet annihilation, or a combination of these processes. In some embodiments, the emissive dopant can be a racemic mixture or can be enriched in one enantiomer. In some embodiments, the compound can be homoleptic (each ligand is the same). In some embodiments, the compound can be heteroleptic (at least one ligand is different from the others). When there is more than one ligand that coordinates to the metal, in some embodiments, the ligands can all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, all of the ligands can be different from each other. This is true even in embodiments where a ligand coordinated to a metal can be bonded to other ligands coordinated to the metal to form tridentate, tetradentate, pentadentate, or hexadentate ligands. Thus, when the coordinating ligands are bonded to one another, in some embodiments, all of the ligands can be the same, and in some other embodiments, at least one of the bonded ligands can be different from the other ligands.

In some embodiments, the compound can be used as a phosphorescent sensitizer in an OLED, where one or more layers in the OLED contain an acceptor in the form of one or more fluorescent and/or delayed fluorescent emitters. In some embodiments, the compound can be used as one component of an exciplex used as a sensitizer. As a phosphorescent sensitizer, the compound must be capable of energy transfer to the acceptor, which either emits energy or further transfers energy to the final emitter. The acceptor concentration can range from 0.001% to 100%. The acceptor can be in the same layer as the phosphorescent sensitizer or in one or more different layers. In some embodiments, the acceptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission can come from any or all of the sensitizer, the acceptor, and the final emitter.

According to another aspect, compositions including the compounds described herein are also disclosed.

The OLEDs disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer, and in some embodiments, the compound can be an emissive dopant, and in other embodiments, the compound can be a non-emissive dopant.

In yet another aspect of the present disclosure, a composition is described that includes the novel compounds disclosed herein. The composition may also include one or more components selected from the group consisting of a solvent, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material disclosed herein.

The present disclosure encompasses any chemical structure that includes the novel compounds of the present disclosure, or monovalent or polyvalent variants thereof. In other words, the compounds of the present invention, or monovalent or polyvalent variants thereof, can be part of a larger chemical structure. Such chemical structures can be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also known as supermolecules). As used herein, a "monovalent variant of a compound" refers to a moiety that is identical to the compound, except that one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. As used herein, a "polyvalent variant of a compound" refers to a moiety that is identical to the compound, except that more than one hydrogen has been removed and replaced with a bond to the remainder of the chemical structure. In the example of a supramolecule, the compounds of the present invention can also be incorporated into the supramolecular complex without a covalent bond.
D. Combinations of Compounds of the Present Disclosure with Other Materials

The materials described herein as useful for 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 can be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present.The materials described or referenced below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that may be useful in combination.
a) Conductive dopants:

The charge transport layer is doped with a conductive dopant to significantly change the density of charge carriers and therefore its conductivity. The conductivity can be increased by creating charge carriers in the matrix material or, depending on the type of dopant, a change in the Fermi level of the semiconductor can also be achieved. The hole transport layer can be doped with a p-type conductive dopant and an n-type conductive dopant is used in the electron transport layer.

Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials.
EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012
b) HIL/HTL:

The hole injection/transport material used in the present disclosure is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injection/transport material. Examples of the material include, but are not limited to, phthalocyanine or porphyrin derivatives, aromatic amine derivatives, indolocarbazole derivatives, polymers containing fluorocarbons, polymers with conductive dopants, conductive polymers such as PEDOT/PSS, self-assembly monomers derived from compounds such as phosphonic acid and silane derivatives, metal oxide derivatives such as _MoOx , p-type semiconducting organic compounds such as 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile, metal complexes, and crosslinkable compounds.

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

Each of Ar ¹ to Ar ⁹ is a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indo and aromatic heterocyclic compounds such as xazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and aromatic hydrocarbon ring groups and aromatic heterocyclic groups, which may be of the same or different types 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. Each Ar can be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one embodiment, Ar ¹ to Ar ⁹ are
wherein k is an integer from 1 to 20; X ¹⁰¹ to X ¹⁰⁸ are C (including CH) or N; Z ¹⁰¹ is NAr ¹ , O, or S; and Ar ¹ has the same group as defined above.

Examples of metal complexes used in the HIL or HTL include, but are not limited to, the following general formula:
where Met is a metal which may have an atomic weight greater than 40; (Y ¹⁰¹ -Y ¹⁰² ) is a bidentate ligand, where Y ¹⁰¹ and Y ¹⁰² are independently selected from C, N, O, P and S; L ¹⁰¹ is an ancillary ligand; k' is an integer value from 1 to the maximum number of ligands which may be bound to the metal; and k'+k'' is the maximum number of ligands which may be bound to the metal.

In one embodiment, (Y ¹⁰¹ -Y ¹⁰² ) is a 2-phenylpyridine derivative. In another embodiment, (Y ¹⁰¹ -Y ¹⁰² ) is a carbene ligand. In another embodiment, Met is selected from Ir, Pt, Os, and Zn. In a further embodiment, the metal complex has a minimum oxidation potential in solution of less than about 0.6 V relative to the Fc ⁺ /Fc couple.

Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials.
CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP0205 5701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP200 5112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898 , KR20130077473, TW201139402, US06517957, US20020158242, US2003016 2053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US200 80106190, US20080124572, US20080145707, US20080220265, US20080233 434, US20080303417, US2008107919, US20090115320, US20090167161, US 2009066235, US2011007385, US20110163302, US2011240968, US20112785 51, US2012205642, US2013241401, US20140117329, US2014183517, US506 1569, US5639914, WO05075451, WO07125714, WO08023550, WO08023759, WO 2009145016, WO2010061824, WO2011075644, WO2012177006, WO201301853 0, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO20131 57367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2 014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018
c) EBL:

An electron blocking layer (EBL) can be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and/or longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine emission to a desired region of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or a higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or a higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or the same functional group used as one of the hosts described below.
d) Host:

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. The host material is not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is greater than that of the dopant. Any host material may be used with any dopant as long as the triplet criteria are met.

Examples of metal complexes used as host materials preferably have the general formula:
where Met is a metal; (Y ¹⁰³ -Y ¹⁰⁴ ) is a bidentate ligand, Y ¹⁰³ and Y ¹⁰⁴ are independently selected from C, N, O, P and S; L ¹⁰¹ is another ligand; k' is an integer value from 1 to the maximum number of ligands that may be bound to the metal; and k'+k'' is the maximum number of ligands that may be bound to the metal.

In one embodiment, the metal complex is a complex:
In the formula, (O--N) is a bidentate ligand with the metal coordinated to atoms O and N.

In another embodiment, Met is selected from Ir and Pt. In a further embodiment, (Y ¹⁰³ -Y ¹⁰⁴ ) is a carbene ligand.

In one embodiment, the host compound is a group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazo and aromatic heterocyclic compounds such as benzofuropyridine, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine; and aromatic hydrocarbon ring groups and aromatic heterocyclic groups, which may be of the same or different types and which 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 cyclic group. Each option within each group can be unsubstituted or substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one embodiment, the host compound contains at least one of the following groups in the molecule:
wherein R ¹⁰¹ is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, has the same definition as that of Ar mentioned above. k is an integer from 0 to 20 or 1 to 20. X ¹⁰¹ to X ¹⁰⁸ are independently selected from C (including CH) or N. ^{Z 101} and Z ¹⁰² are independently selected from NR ¹⁰¹ , O, or S.

Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references that disclose these materials.
EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564 , TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US2 0090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012 126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO200706375 4, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO20100 56066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO 2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803
e) Additional illuminants:

One or more additional emitter dopants can be used with the compounds of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compound can be used as long as the compound is typically used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can generate luminescence via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also known as E-type delayed fluorescence), triplet-triplet annihilation, or a combination of these processes.

Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials.
CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP184 1834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW20 1332980, US06699599, US06916554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123 788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134 462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US200702 31600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US2008023341 0, US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663, US20100244004, US20100295032, US2010102716, U S2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US20 11285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US201410 3305, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US7332232, US7378162, US753 4505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586, US8871361, WO06081973, WO06121811, WO0 7018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008 054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731 , WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO201 3107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450
f) HBL:

A hole blocking layer (HBL) can be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device can result in significantly higher efficiency and/or longer lifetime compared to a similar device lacking a blocking layer. A blocking layer can also be used to confine emission to a desired region of the OLED. In some embodiments, the HBL material has a lower HOMO (further away from the vacuum level) and/or a higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further away from the vacuum level) and/or a higher triplet energy than one or more of the hosts closest to the HBL interface.

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

In another embodiment, the compound used in the HBL comprises at least one of the following groups in the molecule:
wherein k is an integer from 1 to 20; L ¹⁰¹ is another ligand, and k′ is an integer from 1 to 3.
g) 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 ETL materials are not particularly limited, and any metal complex or organic compound typically used to transport electrons may be used.

In one embodiment, the compound used in the ETL contains at least one of the following groups in the molecule:
In the formula, R ¹⁰¹ is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the same definition as that of Ar mentioned above. ^{Ar 1} to Ar ³ have the same definition as that of Ar mentioned above. k is an integer from 1 to 20. X ¹⁰¹ to X ¹⁰⁸ are selected from C (including CH) or N.

In another embodiment, the metal complex used in the ETL comprises, but is not limited to, the following general formula:
where (O-N) or (N-N) is a bidentate ligand with the metal coordinated to atoms O, N or N,N; L ¹⁰¹ is another ligand; and k' is an integer value from 1 to the maximum number of ligands that may be bound to the metal.

Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are illustrated below along with references that disclose these materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, U S20070104977, US2007018155, US20090101870, US20090115316, US200901 40637, US20090179554, US2009218940, US2010108990, US2011156017, US20 11210320, US2012193612, US2012214993, US2014014925, US2014014927, U S20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO20 09148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, W O2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535
h) Charge Generation Layer (CGL)

In tandem or stacked OLEDs, the CGL plays a key role in performance and consists of an n-doped layer and a p-doped layer for the injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are replenished by electrons and holes injected from the cathode and anode, respectively, after which the bipolar current gradually reaches a steady state. Typical CGL materials contain n-type and p-type conductive dopants used in the transport layers.

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 of the specifically mentioned substituents, such as but not limited to methyl, phenyl, pyridyl, etc., can be non-deuterated, partially deuterated, and fully deuterated versions thereof. Similarly, the classes of substituents, such as but not limited to alkyl, aryl, cycloalkyl, heteroaryl, etc., can be non-deuterated, partially deuterated, and fully deuterated versions thereof.

It is 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 can be substituted with other materials and structures without departing from the spirit of the invention. Thus, the invention as claimed may include variations from the specific examples and preferred embodiments described herein, as will be apparent to those of skill in the art. It is understood that the various theories as to why the invention works are not intended to be limiting.

Material synthesis

Synthesis of 7-bromo-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate
7-Bromo-3,4-dihydronaphthalen-1(2H)-one (45.0 g, 200 mmol) and 1,1,1-trifluoro-N-phenyl-N-((trifluoromethyl)sulfonyl)methanesulfonamide (79.0 g, 220 mmol) were dissolved in dry THF (1000 ml). This was cooled to -78°C and a 15% solution of potassium bis(trimethylsilyl)amide in toluene (314 ml, 220 mmol) was added. The reaction mixture was stirred at -78°C for 3 hours. The reaction mixture was left overnight and allowed to warm to room temperature under nitrogen. After all the 7-bromo-3,4-dihydronaphthalen-1(2H)-one had been consumed the reaction was quenched by adding water (50 ml). The crude product was then purified by flash chromatography on standard silica gel using a mixture of heptane and dichloromethane to give 7-bromo-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (68.9 g, 193 mmol, 96% yield) as a pale yellow oil.

Synthesis of 6-bromo-4-(3-chlorophenyl)-1,2-dihydronaphthalene
7-Bromo-3,4-dihydronaphthalen-1-yl trifluoromethanesulfonate (68.9 g, 193 mmol), (3-chlorophenyl)boronic acid (30.2 g, 193 mmol), and Cs ₂ CO ₃ (157 g, 482 mmol) were dissolved in deoxygenated dioxane (1000 ml). [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane) (7.86 g, 9.65 mmol) was added and the reaction mixture was stirred overnight (-16 h) at room temperature under nitrogen. (3-Chlorophenyl)boronic acid (2.00 g, 12.8 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane) (3.00 g, 3.67 mmol) were added and the reaction mixture was stirred overnight at room temperature under nitrogen. The reaction mixture was then heated to 50° C. for 4 h. The solvent was evaporated and the crude product was then purified by flash chromatography on standard silica gel column with heptane to give 6-bromo-4-(3-chlorophenyl)-1,2-dihydronaphthalene (53.9 g, 169 mmol, 87% yield) as a colorless oil.

Synthesis of 7-bromo-1-(3-chlorophenyl)naphthalene
6-Bromo-4-(3-chlorophenyl)-1,2-dihydronaphthalene (53.9 g, 169 mmol) was dissolved in DCM (1000 ml). 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) (57.4 g, 253 mmol) was added at room temperature and the reaction mixture was stirred at 50° C. overnight under nitrogen. The reaction mixture was cooled to room temperature and NaHCO ₃ (sat. aq., 800 ml) and DCM (300 ml) were added. The organic layer was separated and the aqueous layer was washed with DCM (500 ml). The combined organic layers were dried over MgSO ₄ and the volatiles were evaporated. The resulting crude brown oil was purified by flash chromatography in standard silica gel with heptane to give 7-bromo-1-(3-chlorophenyl)naphthalene (41.0 g, 129 mmol, 77% yield) as a pale yellow oil.

Synthesis of 4,4,5,5-tetramethyl-2-(3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,2-dioxaborolane
7-Bromo-1-(3-chlorophenyl)naphthalene (6.00 g, 18.9 mmol), bis(pinacolato)diboron (19.19 g, 75.6 mmol), potassium acetate (9.27 g, 94.5 mmol), and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhos) (1.55 g, 3.78 mmol) were dissolved in dry dioxane (120 mL) in a 500 mL 3-neck round bottom flask connected to a reflux condenser. The mixture was sparged with nitrogen for 15 minutes, after which tris(dibenzylideneacetone)dipalladium(0) (1.73 g, 1.89 mmol) was added and further degassed for an additional 15 minutes. The reaction mixture was then stirred at 100° C. for 18 hours. After cooling to room temperature, the reaction mixture was filtered through a Celite cartridge and the volatiles were removed under vacuum. The resulting dark brown crude mixture was extracted with ethyl acetate (100 mL x 2) and washed with brine (100 mL). The combined organic phases were dried over magnesium sulfate and the solvent was removed under vacuum. The resulting crude mixture was purified by flash chromatography on a standard silica gel column using a mixture of isohexane and ethyl acetate to give a pale yellow solid (4.18 g, 9.26 mmol, 49%).

Synthesis of 4-(tert-butyl)-2-(3-(7-(4-(tert-butyl)pyridin-2-yl)naphthalen-1-yl)phenyl)pyridine
4,4,5,5-Tetramethyl-2-[3-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthyl]phenyl]-1,3,2-dioxaborolane (3.50 g, 7.67 mmol), 4-tert-butyl-2-chloro-pyridine (5.21 g, 30.7 mmol), and tripotassium phosphate (6.51 g, 30.7 mmol) were dissolved in N,N-dimethylformamide (106 mL) in a 500 mL 3-neck round bottom flask connected to a reflux condenser. The mixture was sparged with nitrogen for 15 minutes, after which tetrakis(triphenylphosphine)palladium(0) (1.42 g, 1.23 mmol) was added and further degassed for an additional 15 minutes. The reaction mixture was then stirred at 100° C. for 18 hours. After cooling to room temperature, the reaction mixture was filtered through a celite cartridge and the volatiles were removed under vacuum. The resulting dark brown crude mixture was extracted with ethyl acetate (100 mL x 2) and washed with brine (100 mL). The combined organic phases were dried over magnesium sulfate and the solvent was removed under vacuum. The resulting crude mixture was purified by flash chromatography on a standard silica gel column using a mixture of isohexane and acetone, followed by trituration with isohexane to give a white solid (2.32 g, 4.91 mmol, 64%).

Synthesis of Compound I-A34
A mixture of 4-(tert-butyl)-2-(3-(7-(4-(tert-butyl)pyridin-2-yl)naphthalen-1-yl)phenyl)pyridine (2.7 g, 5.74 mmol) and dichloro(1,5-cyclooctadiene)palladium(II) (2.15 g, 5.74 mmol) in 1,2-dichlorobenzene (10 mL) was sparged with nitrogen for 15 minutes. After refluxing for 6 days, the volatiles were removed under reduced pressure. The crude residue was purified by flash chromatography on a standard silica gel column using mixtures of ethyl acetate and dochloromethane, followed by trituration with methanol to give a brown solid (0.25 g, 0.38 mmol, 6.5%).

Table 1 above shows the results of DFT calculations performed to determine the HOMO/LUMO levels, HOMO-LUMO gap, and lowest triplet (T ₁ ) excited state energy of each compound. Data were collected using the program Gaussian 16. The geometries were optimized using the B3LYP function and CEP-31G basis set. The excited state energies were computed by TDDFT with the optimized ground state geometries. THF solvent was simulated using a self-consistent reaction field to further improve the agreement with experiment. The _T1 energies of the present invention examples Compound I-A1, Compound I-A34, Compound I-A501, Compound II-A1, Compound XXXII-A1, and Compound XXXV-A1 were calculated to be 713, 706, 732, 825, 718, and 710 nm. All of the compounds exhibit phosphorescence in the deep red to near infrared (NIR) region due to the phenyl-naphthalene conjugate moiety.

The photoluminescence (PL) spectrum of the present invention example compound I-A34 obtained in 2-methyl-THF solution at room temperature is shown in Figure 3. The PL intensity was normalized to the maximum first emission peak. The maximum and second emission peaks of the present invention example compound I-A34 are 658 nm and 723 nm. Due to the highly rigid and conjugated phenyl-naphthalene, the present invention example exhibits deep red to near infrared emission. When the present invention example compound is used as an emitting dopant in an organic electroluminescence device, it is expected to emit deep red to near infrared light with good device performance.

The calculations with the DFT functions and basis sets mentioned above are theoretical. Computational hybridization protocols such as Gaussian09 with B3LYP and CEP-31G protocols used herein rely on the assumption that electronic effects are additive, and therefore larger basis sets can be used to extrapolate to the complete basis set (CBS) limit. However, when the goal of the study is to understand the variability of HOMO, LUMO, S ₁ , T ₁ , bond dissociation energies, etc. in a series of structurally related compounds, the additive effects are expected to be similar. Thus, although the absolute errors from using B3LYP may be significant compared to other computational methods, the relative differences between the HOMO, LUMO, S ₁ , T ₁ , and bond dissociation energy values calculated with the B3LYP protocol are expected to reproduce the experiments very well. See, e.g., Hong et al., Chem. Mater. 2016, 28, 5791-98, 5792-93 and Supplemental Information (discussing the reliability of DFT calculations with respect to OLED materials). Moreover, for iridium or platinum complexes useful in OLED technology, the data obtained with DFT calculations correlate very well with actual experimental data. Tavasli et al., J. Mater. Chem. 2012, 22, 6419-29, 6422 (Table 3) (showing that DFT calculations correlate very well with actual data for various emissive complexes); Morello, G. R., J. Mol. Model. 2017, 23:174 (studying a variety of DFT functions and basis sets and concluding that the combination of B3LYP and CEP-31G is particularly accurate for luminescent complexes).

100 organic light emitting device 110 substrate 115 anode 120 hole injection layer 125 hole transport layer 130 electron blocking layer 135 emissive layer 140 hole blocking layer 145 electron transport layer 150 electron injection layer 155 protective layer 160 cathode 162 first conductive layer 164 second conductive layer 170 barrier layer 200 inverted OLED device 210 substrate 215 cathode 220 emissive layer 225 hole transport layer 230 anode

Claims (10)

A compound selected from the group consisting of :
(Wherein,
Each X ² to X ⁹ is C or N;
A ¹ to A ⁸ are each independently C or N, the maximum number of N atoms in the same ring being 3;
R ^A , R ^B , R ^C , and R ^D each represent the maximum allowable substitution from mono or no substitution;
M is Pd or Pt;
each R ^A and R ^B is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine , alkyl, cycloalkyl, aryl , heteroaryl, and combinations thereof;
Each R ^C and R ^D is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof;
R ^X and R ^Y are each independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
Any two substituents can be bonded or fused to each other to form a ring.
However, the compound is
When the formula is as follows, it is limited to the case where at least any two R ^C and any two R ^D are bonded to or fused with each other to form a ring. R ^A and R ^B The compound according to claim 1, wherein at least one of is a 5- or 6-membered heterocycle. R ^A and R ^B 2. The compound of claim 1, wherein at least one of is selected from the group consisting of pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, and N-heterocyclic carbene. Any R ^A and any R ^C do not bond or condense to each other to form a ring, and any two R ^A are not bonded or fused to each other to form a ring, any R ^B and any R ^C do not bond or condense to each other to form a ring, and any two R ^B The compound according to claim 1 , wherein are not bonded or fused to each other to form a ring. Each R ^C and R ^D 2. The compound of claim 1, wherein: is independently hydrogen or a substituent selected from the group consisting of alkyl, alkenyl, aryl, and combinations thereof. 2. The compound of claim 1 selected from the group consisting of:
where i is an integer from 1 to 2000, and for each i, R ¹ , R ² , R ³ , R ⁴ , Y ¹ , and Y ² is defined as follows:
(Here, R ^A1 ~R ^A53 has the following structure:
(R ^B1 ~R ^B46 has the following structure:
(R ^C1 ~R ^C292 has the following structure:
7. The compound of claim 6 selected from the group consisting of:
An anode;
A cathode;
an organic layer disposed between the anode and the cathode,
13. An organic light emitting device (OLED) characterized in that the organic layer comprises a compound according to claim 1. A consumer product comprising the OLED of claim 8. A composition comprising the compound of claim 1.