Organic electroluminescent materials and devices

Abstract

Organic boron compounds are provided. Formulations containing these organic boron compounds are also provided. OLEDs and related consumer products utilizing these organic boron compounds are further provided.

Description

Technology Field

[0001] Cross-reference regarding related applications

[0002] This application claims priority to U.S. Provisional Application No. 62 / 966,662 filed January 28, 2020, under 35 USC § 119(e), the whole of which is incorporated herein by reference.

[0003] field

[0004] The present invention generally relates to organic boron compounds and formulations, and various uses thereof, including as emitters and hosts in devices such as organic light-emitting diodes and related electronic devices. Background Technology

[0005] Optoelectronic devices using organic materials are becoming increasingly important for various reasons. Since many of the materials used to manufacture such devices are relatively inexpensive, organic optoelectronic devices have potential in terms of cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, can make them highly suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic phototransistors, organic photovoltaics, and organic photodetectors. In the case of OLEDs, organic materials can have performance advantages over conventional materials.

[0006] OLEDs use organic thin films that emit light when voltage is applied to the device. OLEDs are a technology that is becoming increasingly important for applications such as flat panel displays, lighting, and backlighting.

[0007] One application of phosphorescent emitting molecules is full-color displays. Industrial standards for such displays require pixels tuned to emit specific colors referred to as "saturated" colors. Specifically, these standards require saturated red, green, and blue pixels. Alternatively, OLEDs can be designed to emit white light. In conventional liquid crystal displays, light from a white backlight is filtered using absorption filters to produce red, green, and blue light. The same technique can also be applied to OLEDs. White OLEDs can be single-emissive layer (EML) devices or stacked structures. Color can be measured using CIE coordinates known in the art. means of solving the problem

[0008] outline

[0009] The present invention discloses a new series of high triplet host compounds based on triaz-trivorinine or tetraaz-tetravorinine. The new hosts have triplet energies higher than 3.1 eV (<400 nm), which are desirable for deep blue phosphorescent emitters.

[0010] In one embodiment, the present invention provides a compound comprising the structure of the following formula I, wherein formula I can be combined with one or more identical structures or polymer compounds:

[0011]

[0012] During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; and R for each case A is independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2is each independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; and any two adjacent R, R 1 , R 2 , or R A It can combine or fuse to form a ring.

[0013] In another aspect, the present invention provides a composition of compounds comprising the structure of Formula I as described herein.

[0014] In another aspect, the present invention provides an OLED having an organic layer comprising a compound having the structure of Formula I as described herein.

[0015] In another aspect, the present invention provides a consumer product comprising an OLED having an organic layer comprising a compound having the structure of Formula I as described herein. Brief explanation of the drawing

[0016] Figure 1 illustrates an organic light-emitting device. Figure 2 illustrates an inverted organic light-emitting device that does not have a separate electron transport layer. Specific details for implementing the invention

[0017] details

[0018] A. Terms

[0019] Unless otherwise specified, the following terms used herein are defined as follows:

[0020] As used herein, the term “organic” includes not only polymeric materials that can be used to fabricate organic optoelectronic devices, but also small molecule organic materials. “Small molecule” refers to any organic material that is not a polymer, and “small molecule” can actually be quite large. Small molecules may contain repeating units in some situations. For example, using a long-chain alkyl group as a substituent does not exclude the molecule from the “small molecule” type. Small molecules may also be incorporated into the polymer, for example, as pendant groups on the polymer main chain or as part of the main chain. Small molecules may also act as the core moiety of a dendrimer, which consists of a series of chemical shells formed on the core moiety. The core moiety of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and all dendrimers currently used in the OLED field are considered to be small molecules.

[0021] As used herein, "top part" means furthest from the substrate, and "bottom part" means closest to the substrate. If the first layer is described as being "placed on top of" the second layer, the first layer is placed far from the substrate. If the first layer is not specified as being "in contact" with the second layer, other layers may exist between the first layer and the second layer. For example, even if various organic layers exist between the cathode and the anode, the cathode may be described as being "placed on top of" the anode.

[0022] As used herein, "solution processability" means that it can be dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension, or can be deposited from a liquid medium.

[0023] If a ligand is considered to directly contribute to the photoactive properties of a luminescent material, the ligand may be referred to as "photoactive." If a ligand is considered not to contribute to the photoactive properties of the luminescent material, even though an auxiliary ligand may alter the properties of the photoactive ligand, the ligand may be referred to as "auxiliary."

[0024] As used herein, and as generally understood by those skilled in the art, where the first energy level is closer to the vacuum energy level, the first "highest occupied molecular orbital (HOMO)" or "lowest unoccupied molecular orbital (LUMO)" energy level is "greater" or "higher" than the second HOMO or LUMO energy level. Since the ionization potential (IP) is measured as negative energy with respect to the vacuum level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (less negative IP). Likewise, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (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. "Higher" HOMO or LUMO energy levels appear closer to the top of the diagram than "lower" HOMO or LUMO energy levels.

[0025] As used herein, and as generally understood by those skilled in the art, if the absolute value of the first work function is greater, the first work function is "greater" or "higher" than the second work function. Since work functions are generally measured as negative numbers with respect to vacuum levels, this implies that the "higher" work function is more negative. In a typical energy level diagram with vacuum levels at the top, the "higher" work function is exemplified as being further down from the vacuum level. Therefore, the definition of HOMO and LUMO energy levels follows a different convention than that of work functions.

[0026] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0027] The term "acyl" refers to a substituted carbonyl radical (C(O)-R s It refers to ).

[0028] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s or -C(O)-OR s ) refers to radicals.

[0029] The term "ether" is -OR s It refers to radicals.

[0030] The terms "sulfanil" or "thio-ether" are used interchangeably, and -SR s It refers to radicals.

[0031] The term "sulfinyl" is -S(O)-R s It refers to radicals.

[0032] The term "sulfonyl" is -SO2-R s It refers to radicals.

[0033] The term "phosphino" is -P(R s Refers to )3 radicals, and each R s It may be the same or different.

[0034] The term "silyl" is -Si(R sRefers to )3 radicals, and each R s It may be the same or different.

[0035] The term "boril" is -B(R s )2 radical or its Lewis adduct -B(Rs)3 radical, where Rs may be the same or different.

[0036] In each of the above, R s may 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 R s is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0037] The term "alkyl" refers to and includes both straight-chain and branched-chain alkyl radicals. Preferred alkyl groups are those containing 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, 2,2-dimethylpropyl, etc. Additionally, the alkyl groups may be optionally substituted.

[0038] The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl radicals. Preferred cycloalkyl groups are those containing 3 to 12 cyclic carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Additionally, cycloalkyl groups may be optionally substituted.

[0039] The terms "heteroalkyl" or "heterocycloalkyl" each refer to an alkyl or cycloalkyl radical having one or more carbon atoms substituted by a heteroatom. Optionally, one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Additionally, the heteroalkyl or heterocycloalkyl group may optionally be substituted.

[0040] The term "alkenyl" refers to and includes both straight-chain and branched-chain alkene radicals. An alkenyl group is essentially an alkyl group comprising one or more carbon-carbon double bonds in an alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group comprising one or more carbon-carbon double bonds within a cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl radical having one or more carbon atoms substituted by a heteroatom. Optionally, one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. A preferred alkenyl, cycloalkenyl, or heteroalkenyl group contains 2 to 15 carbon atoms. Additionally, an alkenyl, cycloalkenyl, or heteroalkenyl group may optionally be substituted.

[0041] The term "alkynyl" refers to and includes both straight-chain and branched-chain alkyne radicals. An alkynyl group is essentially an alkyl group comprising one or more carbon-carbon triple bonds in the alkyl chain. A preferred alkynyl group contains 2 to 15 carbon atoms. Additionally, the alkynyl group may be optionally substituted.

[0042] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. Additionally, the aralkyl group may be optionally substituted.

[0043] The term “heterocyclic group” refers to and includes aromatic and non-aromatic cyclic radicals containing one or more heteroatoms. Optionally, one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, S, or N. Heteroaromatic cyclic radicals may also be used interchangeably with heteroaryls. Preferred heteronon-aromatic cyclic groups are those containing one or more heteroatoms and containing 3 to 7 ring atoms, including cyclic amines such as morpholino, piperidino, pyrrolidino, etc., and cyclic ethers / thio-ethers such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. Additionally, the heterocyclic group may be optionally substituted.

[0044] The term "aryl" refers to and includes both monocyclic aromatic hydrocarbyl groups and polycyclic aromatic ring systems. A polycyclic ring may have two or more rings in which two carbons are common to two adjacent rings (these rings are "fused"), wherein one or more of the rings are aromatic hydrocarbyl groups, and, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. A preferred aryl group contains 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. An aryl group having 6, 10, or 12 carbons is particularly preferred. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl groups may be optionally substituted.

[0045] The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems comprising one or more heteroatoms. Heteroatoms include, but are not limited to, O, S, N, P, B, Si, and Se. In many cases, O, S, or N is a preferred heteroatom. A heteromonocyclic aromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and said ring may have 1 to 6 heteroatoms. A heteropolycyclic ring system may have two or more rings in which two carbons are common to two adjacent rings (these rings are "fused"), wherein one or more of the rings are heteroaryls, and, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryls. The heteropolycyclic aromatic ring system may have 1 to 6 heteroatoms per ring of the polycyclic aromatic ring system. The preferred heteroaryl group contains 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 12 carbon atoms.Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenopene, furan, thiophene, benzofuran, benzothiophene, benzoselenopene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazol, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazolin, quinoxaline, naphthiridine, phthalazine, pteridine, xanthen, acridine, phenazine, Includes phenothiazine, phenoxazine, benzopuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenofenofyridine and selenofenodipyridine, preferably dibenzothiophen, dibenzofuran, dibenzoselenofen, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azabolin, 1,3-azabolin, 1,4-azabolin, borazine and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.

[0046] Among the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenopene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and their respective aza-analogs are of particular interest.

[0047] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl are independently unsubstituted or independently substituted with one or more common substituents.

[0048] In many cases, common substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0049] In some cases, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

[0050] In some cases, preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and combinations thereof.

[0051] In another case, more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0052] The terms "substituted" and "substituted" refer to substituents other than H bonded to the relevant positions, such as carbon or nitrogen. For example, R 1 In the case where this represents a uniform substitution, one R 1 must be something other than H (i.e., substitution). Similarly, R 1 In the case where this represents a bisubstitution, R 1 Two of them must be something other than H. Similarly, R 1 If this represents no substitution or no substitution, R 1The available valence of the ring atom can be hydrogen, for example, the carbon atom of benzene and the nitrogen atom of pyrrole, or simply nothing for the ring atom with a fully charged valence, such as the nitrogen atom of pyridine. The maximum number of substitutions possible in a ring structure depends on the total number of available valences in the ring atom.

[0053] As used herein, “combinations thereof” indicates that one or more components of the applicable list are combined to form a known or chemically stable arrangement that a person skilled in the art can conceive from the applicable list. For example, alkyl and deuterium may be combined to form a partially or wholly deuteriden alkyl group; halogen and alkyl may be combined to form a halogenated alkyl substituent; and halogen, alkyl, and aryl may be combined to form a halogenated arylalkyl. In one case, the term substitution comprises a combination of two to four of the listed groups. In another case, the term substitution comprises a combination of two to three groups. In yet another case, the term substitution comprises a combination of two groups. A preferred combination of substituents is one containing up to 50 atoms that are not hydrogen or deuterium, or one containing up to 40 atoms that are not hydrogen or deuterium, or one containing up to 30 atoms that are not hydrogen or deuterium. In many cases, the preferred combination of substituents will include up to 20 atoms that are not hydrogen or deuterium.

[0054] In the fragments described herein, namely aza-dibenzofuran, aza-dibenzothiophene, etc., the notation "aza" signifies that one or more of the CH groups in each aromatic ring can be substituted with nitrogen atoms, for example, azatriphenylene is dibenzo[ f,h ]Quinoxaline and dibenzo[ f,h] Includes, but is not limited to, all quinoline. Those skilled in the art may readily consider other nitrogen analogs of the aforementioned aza derivatives, and all such analogs are intended to be encompassed by the terms described herein.

[0055] 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. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951, and U.S. Patent Application Publication No. US 2011 / 0037057, the entire text of which is incorporated herein by reference, describe the preparation of deuterium-substituted organometallic complexes. Additionally, the literature [Ming Yan, et al ., Tetrahedron 2015, 71, 1425-30] and literature[Atzrodt et al ., Angew. Chem. Int. Ed. (Reviews) See [2007, 46, 7744-65], the full text of which is incorporated herein by reference, and which each describe efficient routes for the deuteration of methylene hydrogens in benzylamine and the substitution of aromatic ring hydrogens with deuteration.

[0056] Where a molecular segment is described as a substituent or, if not, as attached to another moiety, it should be understood that its name may be described as the segment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or as the whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, different notations of such substituents or attached segments are considered equivalent.

[0057] In some cases, pairs of adjacent substituents may be arbitrarily combined (linked) or fused to form a ring. A preferred ring is a pentagonal, hexagonal, or heptagonal carbocyclic or heterocyclic ring, including cases where part of the ring formed by the pair of substituents is saturated and cases where part of the ring formed by the pair of substituents is unsaturated. As used herein, “adjacent” means that two related substituents may exist on two adjacent rings having the two closest substituable positions, e.g., the 2, 2’ position of biphenyl or the 1, 8 position of naphthalene, or on the same ring adjacent to each other, as long as a stable fused ring system can be formed.

[0058] B. Compounds of the present invention

[0059] In one embodiment, the present invention provides a compound comprising the structure of the following formula I, wherein formula I can be combined with one or more identical structures or polymer compounds:

[0060]

[0061] During the meal,

[0062] R A represents no substitution, identical substitution, or identical substitution for its related loop;

[0063] R for each case A is independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein;

[0064] R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;

[0065] R 1 and R 2 Each is independently a hydrogen, or a substituent selected from the group consisting of general substituents defined herein;

[0066] Any 2 adjacent R, R1 , R 2 , or R A It can combine or fuse to form a ring.

[0067] In some embodiments, the compound of Formula I may have the structure of Formula II below:

[0068]

[0069] During the meal, R 3 and R 4 is each independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; and any two adjacent R, R 1 , R 2 , R 3 , R 4 , or R A It can combine or fuse to form a ring.

[0070] In some embodiments, the compound of Formula I may have the structure of Formula III below:

[0071]

[0072] During the meal, L 1 It is a linker selected from the group consisting of a 1-atom main chain, a 2-atom main chain, a 3-atom main chain, a 4-atom main chain, a 5-atom main chain, and a 6-atom main chain.

[0073] In some embodiments, the main chain atoms may be selected from the group consisting of B, N, Si, C, O, S, and P. In some embodiments, L 1 It may be a linker comprising a two-atom main chain of B and N atoms. In some embodiments, L 1 It may be a linker containing a 4-atom main chain of 2 B and 2 N atoms.

[0074] In some embodiments, R for each case Amay independently be a substituent selected from the group consisting of hydrogen, or deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof. In some embodiments, R may be an aryl or heteroaryl group. In some embodiments, R may be a benzene or pyridine ring. In some embodiments, R 2 may be an aryl or heteroaryl group. In some embodiments, R 2 can be a benzene or pyridine ring. In some embodiments, R 1 can be an amino group. In some embodiments, R 1 can be an aryl or heteroaryl substituted amino group. In some embodiments, two Rs A Substituents can combine to form a fused six-membered aromatic ring. In some embodiments, R for each case A can be H.

[0075] In some embodiments, the compound of formula I may have the structure of formula IV below:

[0076]

[0077] During the meal, L 2 is a direct bond, or a linker selected from the group consisting of a 1-atom main chain, a 2-atom main chain, a 3-atom main chain, and a 4-atom main chain group, where the main chain atoms are selected from B, N, Si, C, O, S, and P; R 5 and R 6 is each independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; and any two adjacent R, R 1 , R 2 , R 5 , R 6 , or R A It can combine or fuse to form a ring.

[0078] In some embodiments, L 2 can be a direct bond between B and N, and the compound has the structure of the following chemical formula V:

[0079] .

[0080] In some embodiments, R 1 can be an amino or arylamino group. In some embodiments, R 5 may be an aryl or heteroaryl group. In some embodiments, R 5 The aryl or heteroaryl group of, and R 1 The amino or aryl amino groups of can combine to form a fused ring system. In some embodiments, R 6 can be an amino or arylamino group. In some embodiments, R 2 may be an aryl or heteroaryl group. In some embodiments, R 2 The aryl or heteroaryl group of, and R 6 The amino or arylamino groups of can combine to form a fused ring system.

[0081] In some embodiments, L 2 The linker may be a two-atom main chain of B and N atoms. In some embodiments, the compound may have the structure of the following formula VI:

[0082]

[0083] During the meal, R 7 and R 8 is each independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; and any two adjacent R, R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , or R A It can combine or fuse to form a ring.

[0084] In some embodiments, R 1 can be an amino or arylamino group. In some embodiments, R 5 may be an aryl or heteroaryl group. In some embodiments, R 5 The aryl or heteroaryl group of, and R 1 The amino or arylamino groups of can combine to form a fused ring system. In some embodiments, R 7 can be an amino or arylamino group. In some embodiments, R 8 can be an aryl or heteroaryl group. In some embodiments, R 8 The aryl or heteroaryl group of, and R 7 The amino or arylamino groups of can combine to form a fused ring system. In some embodiments, R 6 can be an amino or arylamino group. In some embodiments, R 2 may be an aryl or heteroaryl group. In some embodiments, R 2 The aryl or heteroaryl group of, and R 6 The amino or arylamino groups of can combine to form a fused ring system.

[0085] In some embodiments, two Rs A Substituents may bond together to form a fused six-membered aromatic ring. In some embodiments, the fused six-membered aromatic ring may be pyrimidine, pyridine, pyridazine, pyrazine, triazine, or benzene. In some embodiments, two Rs A Substituents can combine to form a fused benzene ring.

[0086] In some embodiments, the compound may further include one or more carbazole groups.

[0087] In some embodiments, the compound may be selected from the group consisting of the following:

[0088]

[0089] During the meal, R B , R C , and R D represents no substitution, identical substitution, or identical substitution for its associated loop, respectively;

[0090] R for each case B , R C , and R D is independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein;

[0091] R A' , R B' , R C' , and R D' Each represents no substitution, identical substitution, or the maximum number of permutations allowed for its associated loop;

[0092] R B , R C , R D , R A' , R B' , R C' , R D' , R 1' , R 2' , R 3' , and R 4 Each is independently a hydrogen, or a substituent selected from the group consisting of general substituents defined herein;

[0093] Two adjacent substituents can combine or fuse to form a ring;

[0094] R A is the same as previously defined for Chemical Formula I.

[0095] In some embodiments, the compound may be selected from the group consisting of:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] Among the formulas, R1 to R70 have the following structure:

[0103]

[0104]

[0105] .

[0106] In some embodiments, the compound may be selected from the group consisting of the following:

[0107]

[0108]

[0109]

[0110]

[0111] .

[0112] C. OLED and device of the present invention

[0113] In another aspect, the present invention also provides an OLED device comprising a first organic layer comprising a compound disclosed in the compound section of the present invention.

[0114] In some embodiments, the organic layer may comprise a compound having a structure of the following formula I, wherein formula I may be combined with one or more identical structures or polymer compounds:

[0115]

[0116] During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; and R for each case Ais independently hydrogen or a general substituent as described herein; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2 Each is independently hydrogen, or a general substituent as described herein; and any two adjacent R, R 1 , R 2 , or R A It can combine or fuse to form a ring.

[0117] In some embodiments, the first organic layer may be a light-emitting layer, and the compound described herein may be a light-emitting dopant or a non-light-emitting dopant.

[0118] In some embodiments, the compound may be a fluorescent emitter.

[0119] In some embodiments, the first organic layer may further include a phosphorescent sensitizer, and the compound is a fluorescent acceptor.

[0120] In some embodiments, the OLED may include a second organic layer disposed between the anode and the cathode, wherein the second organic layer includes a phosphorescent sensitizer, and the compound is a fluorescent acceptor.

[0121] In some embodiments, the phosphorescent sensitizer may be at least one ligand selected from the group consisting of the following, or a transition metal complex having a portion of the ligand when the ligand has more than two sites:

[0122]

[0123]

[0124] Among the formulas, each Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen; Y' is BR e , NR e , PR e, O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f and GeR e R f Selected from a group consisting of; R e and R f is arbitrarily fused or combined to form a ring; each R a , R b , R c and R d is independently denoted as no substitution, uniform substitution, or maximum permissible substitution for its associated loop; R a , R b , R c , R d , R e and R f is a substituent selected from the group consisting of hydrogen, or deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R a , R b , R c and R d Two adjacent substituents among them may fuse or combine to form a ring or a multidentate ligand.

[0125] In some embodiments, one or more organic layers disposed between the anode and the cathode comprise a host, wherein the host comprises at least one chemical group selected from the group consisting of anthracene, naphthalene, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenopene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenopene.

[0126] In some embodiments, the host may be selected from a group of hosts consisting of the following:

[0127]

[0128]

[0129] and combinations thereof.

[0130] In another aspect, the OLED of the present invention may also include a light-emitting region comprising a compound disclosed in the compound section of the present invention.

[0131] In some embodiments, the light-emitting region may comprise a compound having the structure of the following formula I, and formula I may be combined with one or more identical structures or polymer compounds:

[0132]

[0133] During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; and R for each case A is independently hydrogen or a general substituent as described herein; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2 is each independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; and any two adjacent R, R 1 , R 2 , or R A It can combine or fuse to form a ring.

[0134] In some embodiments, at least one of the new layers disposed on the anode, cathode, or organic light-emitting layer functions as an enhancement layer. The enhancement layer comprises a plasmonic material that exhibits surface plasmon resonance, which non-radiatively binds to the emitter material and transfers excited state energy from the emitter material to the non-radiative mode of a surface plasmon polariton. The enhancement layer is provided to be located below a critical distance from the organic light-emitting layer, wherein the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer, and the critical distance is where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer opposite the organic light-emitting layer. In some embodiments, the outcoupling layer is disposed on the light-emitting layer opposite the enhancement layer but still outcouples energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polariton. In some embodiments, the energy is scattered into free space as photons. In other embodiments, the energy is scattered from a surface plasmon mode, for example, but not limited to, an organic waveguide mode, a substrate mode, or other modes of the device, such as other waveguide modes. If the energy is scattered into a non-free space mode of the OLED, other outcoupling schemes may be introduced to extract the energy into free space. In some embodiments, one or more interlayers may be disposed between the enhancement layer and the outcoupling layer. Examples of the interlayer(s) may be dielectric materials, including organic, inorganic, perovskite, and oxide materials, and may include stacks and / or mixtures of these materials.

[0135] The enhancement layer modifies the effective properties of the medium in which the emitter material is present, thereby changing any one or all of the following: a reduction in emission rate, modification of the emission line shape, a change in emission intensity with respect to angle, a change in the stability of the emitter material, a change in OLED efficiency, and a reduction in the roll-off of the OLED device. By placing the enhancement layer on the cathode side, the anode side, or both the cathode and the anode sides, an OLED device utilizing any one of the aforementioned effects can be made. In addition to the specific functional layer exemplified in the various OLED examples mentioned herein and illustrated in the drawings, the OLED according to the present invention may also include any other functional layer commonly found in OLEDs.

[0136] The enhancement layer may be composed of a plasmonic material, an optically active metamaterial, or a hyperbolic metamaterial. As used herein, a plasmonic material is a material in which the real part of the permittivity is non-zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material comprises at least one metal. In these embodiments, the metal may comprise at least one of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of these materials, and stacks of these materials. Generally, a metamaterial is a medium composed of different materials in which the entire medium acts differently from the sum of its parts. In particular, the inventors define an optically active metamaterial as a material having both negative permittivity and negative transmittance. On the other hand, a hyperbolic metamaterial is an anisotropic medium in which the permittivity or transmittance has different signs for different spatial directions. Optically active metamaterials and hyperbolic metamaterials are strictly distinguished from various other photonic structures, such as dispersive Bragg reflectors ("DBRs"), in that the corresponding medium must appear uniform in terms of wavelength in the direction of light propagation. Using terms understood by those skilled in the art: the permittivity of a metamaterial in the direction of propagation can be described by the effective medium approximation. Plasmon materials and metamaterials provide a method for controlling light propagation that can improve OLED performance in various ways.

[0137] In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has wavelength-sized features arranged periodically, quasi-periodically, or randomly, or has wavelength-smaller features arranged periodically, quasi-periodically, or randomly. In some embodiments, the wavelength-sized features and wavelength-smaller features have sharp edges.

[0138] In some embodiments, the outcoupling layer has wavelength-sized features arranged periodically, quasi-periodically, or randomly, or has features smaller than wavelengths arranged periodically, quasi-periodically, or randomly. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed on a material. In these embodiments, outcoupling may be adjusted by at least one of changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the said material, changing the refractive index or additional layer of the material disposed on the plurality of nanoparticles, changing the thickness of the enhancement layer and / or changing the material of the enhancement layer. The plurality of nanoparticles of the device may be formed from at least one of a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layer of one or more materials, and / or a core made of one type of material coated with a shell of different types of materials. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of Ag, Al, Au, Ir, Pt, Ni, Cu, W, Ta, Fe, Cr, Mg, Ga, Rh, Ti, Ru, Pd, In, Bi, Ca, alloys or mixtures of said materials, and stacks of said materials. Multiple nanoparticles may have additional layers disposed on top of them. In some embodiments, the polarization of the emission can be adjusted using the outcoupling layer. By varying the dimensions and periodicity of the outcoupling layer, a type of polarization that preferentially outcouples with air can be selected. In some embodiments, the outcoupling layer also acts as an electrode of the device.

[0139] In another aspect, the present invention 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, wherein the organic layer may comprise a compound disclosed in the compound section of the present invention.

[0140] In some embodiments, the consumer product comprises an organic light-emitting device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound having a structure of the following formula I, and formula I may be combined with one or more identical structures and / or polymer compounds:

[0141]

[0142] During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; and R for each case A is independently hydrogen or a general substituent as described herein; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2 is each independently hydrogen, or a substituent selected from the group consisting of general substituents defined herein; and any two adjacent R, R 1 , R 2 , or R A It can combine or fuse to form a ring.

[0143] In some embodiments, the consumer product may be one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor lighting and / or signal light, 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 information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay with a diagonal of less than 2 inches, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.

[0144] Generally, an OLED comprises one or more organic layers disposed between an anode and a cathode and electrically connected to them. When current is applied, the anode injects holes into the organic layer(s), and the cathode injects electrons. The injected holes and electrons move toward oppositely charged electrodes, respectively. When electrons and holes are localized on the same molecule, "excitons" are generated, which are localized electron-hole pairs with excited energy states. Light is emitted when excitons relax through a photo-emission mechanism. In some cases, excitons may be localized on excimers or exciplexes. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.

[0145] Various OLED materials and compositions are described in U.S. Patents No. 5,844,363, 6,303,238 and 5,707,745, the full text of which is incorporated herein by reference.

[0146] Early OLEDs used light-emitting molecules that emit light ("fluorescence") from a singlet state, such as disclosed in, for example, U.S. Patent No. 4,769,292, the entirety of which is incorporated by reference. Fluorescence emission generally occurs in a time frame of less than 10 nanoseconds.

[0147] More recently, OLEDs having a light-emitting material that emits light ("phosphorescence") from a triplet state have been presented. The literature [Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, vol. 395, 151-154, 1998; ("Baldo-I")] and the literature [Baldo et al., "Very high-efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) ("Baldo-II")] are incorporated by reference in their entirety. Phosphorescence is described in more detail in columns 5-6 of U.S. Patent No. 7,279,704, incorporated by reference.

[0148] FIG. 1 illustrates an organic light-emitting device (100). The drawing is 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), a light-emitting 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 layers in the order described. The properties and functions of the exemplary materials, as well as these various layers, are described more specifically in columns 6-10 of U.S. Patent No. 7,279,704, which is incorporated by reference.

[0149] Further examples for each of these layers are also available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, the full text of which is incorporated by reference. An example of a p-doped hole transport layer is one in which m-MTDATA is doped with F4-TCNQ in a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, the full text of which is incorporated by reference. Examples of luminescent and host materials are disclosed in U.S. Patent No. 6,303,238 (Thompson et al.), the full text of which is incorporated by reference. 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, the full text of which is incorporated by reference. Examples of cathodes are disclosed in U.S. Patents No. 5,703,436 and No. 5,707,745, the full text of which is incorporated by reference, including compound cathodes having thin layers of metals such as Mg:Ag with stacked transparent, electrically conductive sputter-deposited ITO layers. The theory and applications 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, the full text of which is incorporated by reference. An example of an injection layer is provided in U.S. Patent Application Publication No. 2004 / 0174116, the full text of which is incorporated by reference. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, the full text of which is incorporated by reference.

[0150] FIG. 2 illustrates an inverted structure OLED (200). The device comprises a substrate (210), a cathode (215), a light-emitting layer (220), a hole transport layer (225), and an anode (230). The device (200) can be fabricated by depositing layers in the order described. Since the most common OLED configuration has the cathode positioned above the anode and the device (200) has the cathode (215) positioned below the anode (230), the device (200) may be referred to as an "inverted structure" OLED. A material similar to that described for the device (100) may be used for the corresponding layers of the device (200). FIG. 2 provides an example of how some layers may be omitted from the structure of the device (100).

[0151] The simple stacked structure illustrated in FIGS. 1 and 2 is provided as a non-limiting example, and it is understood that embodiments of the present invention may be used in connection with various other structures. The specific materials and structures described are for illustrative purposes only, and other materials and structures may also be used. Functional OLEDs may be achieved by combining the various layers described in different 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. Although many examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of a host and a dopant, or more generally a mixture, may be used. Additionally, layers may have various underlying layers. The names given herein for the various layers are not intended to be strictly limited. For example, in the device (200), the hole transport layer (225) transports holes and injects holes into the light-emitting layer (220), and may be described as a hole transport layer or a hole injection layer. In one embodiment, the OLED may be described as having an "organic layer" disposed between the cathode and the anode. This organic layer may comprise a single layer, or may further comprise a plurality of layers of different organic materials, for example, as described in relation to FIGS. 1 and 2.

[0152] OLEDs (PLEDs) comprising structures and materials not specifically described, such as polymer materials as disclosed in U.S. Patent No. 5,247,190 (Friend et al.), may also be used, the full text of which is incorporated herein by reference. As an additional example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example, as described in U.S. Patent No. 5,707,745 (Forrest et al.), the full text of which is incorporated herein by reference. OLED structures may deviate from the simple stacked structures shown in FIGS. 1 and 2. For example, the substrate may include angled reflective surfaces to improve out-coupling, such as a mesa structure as described in U.S. Patent No. 6,091,195 (Forrest et al.) and / or a pit structure as described in U.S. Patent No. 5,834,893 (Bulovic et al.), the full text of which is incorporated herein by reference.

[0153] Unless otherwise specified, any layer of any embodiment may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation as described in U.S. Patents No. 6,013,982 and 6,087,196 (the full text of which is incorporated by reference), ink-jet, organic vapor deposition (OVPD) as described in U.S. Patent No. 6,337,102 (Forrest et al.) (the full text of which is incorporated by reference), and organic vapor jet printing (OVJP) as described in U.S. Patent No. 7,431,968 (the full text of which is incorporated by reference). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably carried out in nitrogen or an inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred pattern formation methods include pattern formation associated with some deposition methods such as deposition through a mask, cold welding as described in U.S. Patents No. 6,294,398 and 6,468,819 (the full text of which is incorporated by reference), ink-jet, and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to be compatible with a specific deposition method. For example, branched or unbranched substituents, such as alkyl and aryl groups containing three or more carbons, may be used on small molecules to improve their solution processing capabilities. Substituents having 20 or more carbons may be used, with 3 to 20 carbons being a preferred range. Since asymmetric materials may have a lower tendency for recrystallization, materials with asymmetric structures may have better solution processing capabilities than materials with symmetric structures. Dendrimer substituents may be used to improve the solution processing capabilities of small molecules.

[0154] A device fabricated according to an embodiment of the present invention may optionally further include a barrier layer. One purpose of the barrier layer is to protect the electrode and organic layer from damage caused by exposure to harmful species in an environment containing moisture, vapor and / or gas. The barrier layer may be deposited on any other part of the device including the edge, on the electrode or, on the underside or side of the substrate. 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 comprise a composition having multiple phases as well as a composition having a single phase. Any suitable material or combination of materials may be used in the barrier layer. The barrier layer may comprise inorganic or organic compounds or both. A preferred barrier layer comprises a mixture of polymeric and non-polymeric materials as described in U.S. Patent No. 7,968,146, PCT Application Nos. PCT / US2007 / 023098 and PCT / US2009 / 042829, the full text of which is incorporated herein by reference. To be considered a "mixture," the aforementioned polymer and nonpolymer materials, including the barrier layer, must be deposited under the same reaction conditions and / or at the same time. The weight ratio of the polymer to the nonpolymer material may be in the range of 95:5 to 5:95. The polymer and nonpolymer materials may be produced from the same precursor material. In one example, the mixture of the polymer and nonpolymer materials essentially consists of polymeric silicon and inorganic silicon.

[0155] A device manufactured according to an embodiment of the present invention may be contained within a wide variety of electronic component modules (or units) that may be included in various electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, light-emitting devices, such as individual light source devices or lighting panels, which may be used by end consumer product manufacturers. Such electronic component modules may optionally include driving electronic devices and / or power source(s). A device manufactured according to an embodiment of the present invention may be contained within a wide variety of consumer products that include one or more electronic component modules (or units). A consumer product comprising an OLED that includes a compound of the present invention in an organic layer within the OLED is disclosed. Such consumer products may include any type of product comprising one or more light source(s) and / or one or more of any type of image display. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lights, head-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablets, phablets, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays (displays with a diagonal of less than 2 inches), 3D displays, virtual reality or augmented reality displays, vehicles, video walls including multiple displays tiled together, theater or stadium screens, phototherapy devices, and signage. Devices manufactured according to the present invention can be controlled using various control mechanisms, including passive matrices and active matrices.Many devices are intended to be used in a temperature range that provides comfort to people, such as 18°C ​​to 30°C, more preferably at room temperature (20°C to 25°C), but can also be used at temperatures outside the above temperature range, such as -40 to +80°C.

[0156] Further details regarding OLEDs and the foregoing definitions can be found in U.S. Patent No. 7,279,704, the full text of which is incorporated herein by reference.

[0157] The materials and structures described herein may have applications 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.

[0158] In some embodiments, the OLED has one or more properties selected from the group consisting of flexible, rollable, foldable, stretchable, and curved properties. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer containing carbon nanotubes.

[0159] In some embodiments, the OLED further comprises a layer containing a delay fluorescence emitter. In some embodiments, the OLED comprises an array of RGB pixels, or an array of white plus color filter pixels. 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 with 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 with a diagonal of 10 inches or more or an area of ​​50 square inches or more. In some embodiments, the OLED is a lighting panel.

[0160] In some embodiments, the compound may be a luminescent dopant. In some embodiments, the compound may produce luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, for example, U.S. Patent Application No. 15 / 700,352, the full text of which is incorporated herein by reference), triplet-triplet extinction, or a combination of these processes. In some embodiments, the luminescent dopant may be a racemic mixture or may be rich in one enantiomer. In some embodiments, the compound may be homoligandic (each ligand is identical). In some embodiments, the compound may be heteroligandic (at least one ligand is different from the others). Where more than one ligand is coordinated to the metal, the ligands may all be identical in some embodiments. In some other embodiments, at least one ligand is different from the remaining ligands. In some embodiments, all ligands may be different from each other. This also applies to embodiments in which a ligand coordinated to a metal may be connected to another ligand coordinated to the metal to form a triad, tetraad, quintad, or hexaadad. Thus, when the coordination ligands are connected together, all ligands may be the same in some embodiments, and at least one of the connected ligands may be different from the remaining ligand(s) in some other embodiments.

[0161] In some embodiments, the compound may be used as a phosphorescent sensitizer in an OLED, wherein one or more layers within the OLED contain acceptors in the form of one or more fluorescent and / or delayed fluorescent emitters. In some embodiments, the compound may be used as one component of an exciplex used as a sensitizer. As a phosphorescent sensitizer, the compound must be able to transfer energy to the acceptor, and the acceptor releases energy or additionally transfers energy to the final emitter. The acceptor concentration may be in the range of 0.001% to 100%. The acceptor may 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, luminescence may occur from any or all of the sensitizer, the acceptor, and the final emitter.

[0162] According to another embodiment, a formulation comprising the compound described herein is also disclosed.

[0163] The OLED disclosed herein may be included in one or more of consumer products, electronic component modules, and lighting panels. The organic layer may be a light-emitting layer, and the compound may be a light-emitting dopant in some embodiments, while the compound may be a non-light-emitting dopant in other embodiments.

[0164] In another aspect of the present invention, a formulation comprising a novel compound disclosed herein is described. The formulation may comprise 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.

[0165] The present invention comprises any chemical structure comprising the novel compound of the present invention, or a monovalent or polyvalent variant thereof. That is, the compound of the present invention, or a monovalent or polyvalent variant thereof, may be part of a larger chemical structure. Such chemical structures may be selected from the group consisting of monomers, polymers, macromolecules, and supramolecules (also known as supermacromolecules). As used herein, a “monovalent variant of the compound” exhibits the same moiety as the compound except that one hydrogen is removed and replaced by a bond to the remainder of the chemical structure. As used herein, a “polyvalent variant of the compound” exhibits the same moiety as the compound except that one or more hydrogens are removed and replaced by a bond or bonds to the remainder of the chemical structure. In the case of supramolecules, the compound of the present invention may also be incorporated into a supramolecular complex without covalent bonding.

[0166] D. Combination of the compound of the present invention and other substances

[0167] The materials described herein as useful for a specific layer in an organic light-emitting device may be used in combination with a wide variety of other materials present in the device. For example, the light-emitting dopant disclosed herein may be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and those skilled in the art may readily refer to the literature to identify other materials that may be useful in combination.

[0168] a) Conductive dopant:

[0169] The charge transport layer can be doped with a conductive dopant to substantially change its charge carrier density, which will consequently change its conductivity. Conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the semiconductor's Fermi level 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.

[0170] Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing the materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047, and US2012146012.

[0171] .

[0172] b) HIL / HTL :

[0173] The hole injection / transport material intended for use in the present invention is not specifically limited, and any compound commonly used as a hole injection / transport material may be used. Non-limiting examples of materials include phthalocyanine or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; polymers comprising fluorohydrocarbons; polymers having conductive dopants; conductive polymers, e.g., PEDOT / PSS; self-assembling monomers derived from compounds such as phosphonic acids and silane derivatives; and metal oxide derivatives, e.g., MoO₂ x; p-type semiconductor organic compounds, such as 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; metal complexes and crosslinkable compounds may be examples.

[0174] Non-limiting examples of aromatic amine derivatives used in HIL or HTL include the following structural formulas:

[0175] .

[0176] Each Ar 1 or Ar 9is a group composed of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; Dibenzothiophen, Dibenzofuran, Dibenzoselenopene, Furan, Thiophene, Benzofuran, Benzothiophene, Benzoselenopene, Carbazole, Indolocarbazole, Pyridylindole, Pyrrolodipyridine, Pyrazol, Imidazole, Triazole, Oxazole, Thiazole, Oxadiazole, Oxatriazole, Dioxazole, Thiadiazole, Pyridine, Pyridazine, Pyrimidine, Pyrazine, Triazine, Oxazine, Oxathiazine, Oxadiazine, Indole, Benzimidazole, Indazole, Indoxazine, Benzoxazole, Benzisoxazole, Benzothiazole, Quinoline, Isoquinoline, Sinnoline, Quinazolin, Quinoxaline, Naphthiridine, Phthalasine, Pteridine, Xanthen, Acridine, Phenazine, Phenothiazine, A group consisting of aromatic heterocyclic compounds such as phenoxazine, benzopuropyridine, propipyridine, benzothiopyridine, thienodipyridine, benzoselenofenopyridine, and selenofenopyridine; and a group of the same or different types selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and a group consisting of 2 to 10 cyclic structural units that are bonded through or directly bonded to each other through one or more 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 Ar may 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.

[0177] In one mode, Ar 1 or Ar 9 is independently selected from the group consisting of the following chemical formulas:

[0178]

[0179] Here, k is an integer from 1 to 20; X 101 To X 108 is C (including CH) or N; Z 101 eu NAr 1 , O or S and; Ar 1 It has the same mechanism as defined above.

[0180] Non-limiting examples of metal complexes used in HIL or HTL include the following chemical formulas:

[0181]

[0182] Here, Met is a metal and can have an atomic weight greater than 40; (Y 101 -Y 102 ) is a 2-position ligand, and Y 101 and Y 102 is independently selected from C, N, O, P, and S; L 101 is an auxiliary ligand; k' is an integer value of the maximum number of ligands that can be attached to the metal, ranging 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.

[0183] In one mode, (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 versus Fc in solution of less than about 0.6 V. + / Fc has a couple.

[0184] Non-limiting examples of HIL and HTL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, US06517957, US20020158242, US20030162053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US20080106190, US20080124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US2011007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, US5061569, US5639914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812,WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018.,

[0185]

[0186]

[0187]

[0188]

[0189] .

[0190] c) EBL:

[0191] An electron blocking layer (EBL) can be used to reduce the number of electrons and / or excitons leaving the emissive layer. The presence of such a blocking layer within the device can lead to significantly higher efficiency and / or longer lifetime compared to a similar device without a blocking layer. Additionally, the blocking layer can be used to confine light emission to a desired area of ​​the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and / or 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 higher triplet energy than one or more of the hosts closest to the EBL interface. In one embodiment, the compound used in the EBL contains the same molecule or functional group as one of the hosts described below.

[0192] d) Host:

[0193] The light-emitting layer of the organic EL device of the present invention preferably comprises at least a metal complex as a light-emitting material and may comprise a host material using a metal complex as a dopant material. Examples of host materials are 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 the triplet energy of the dopant. Any host material may be used with any dopant as long as the triplet criterion is satisfied.

[0194] An example of a metal complex used as a host preferably has the following chemical formula:

[0195]

[0196] Here, Met is a metal; (Y 103 -Y 104 ) is a 2-position ligand, and Y 103 and Y 104 is independently selected from C, N, O, P, and S; L 101 is another ligand; k' is an integer value of the maximum number of ligands that can be attached to the metal, from 1 to; and k'+k" is the maximum number of ligands that can be attached to the metal.

[0197] In one embodiment, the metal complex , where (ON) is a 2-bed ligand having a metal coordinated to atoms O and N.

[0198] In another embodiment, Met is selected from Ir and Pt. In an additional embodiment, (Y 103 -Y 104 ) is a carbene ligand.

[0199] In one embodiment, the host compound is an aromatic hydrocarbon cyclic compound, such as a group consisting of benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; Aromatic heterocyclic compounds, e.g., dibenzothiophene, dibenzofuran, dibenzoselenopene, furan, thiophene, benzofuran, benzothiophene, benzoselenopene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazol, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazolin, quinoxaline, naphthiridine, phthalazine, pteridine, xanthen, acridine, It contains at least one of the group selected from the group consisting of phenazine, phenothiazine, phenoxazine, benzopuropyridine, purodipyridine, benzothienopyridine, thienodipyridine, benzoselenofenofyridine and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units that are of the same or different type selected from aromatic hydrocarbon cyclic groups and aromatic heterocyclic groups, and are bonded through or directly bonded to each other through one or more 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 may 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.

[0200] In one embodiment, the host compound contains one or more of the following groups in the molecule:

[0201]

[0202] Here, 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 if it is aryl or heteroaryl, it has a definition similar to that of Ar described above. k is an integer from 0 to 20 or from 1 to 20. X 101 To X 108 is independently selected from C (including CH) or N. Z 101 and Z 102 is independently NR 101 , is selected from O or S.

[0203] Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, US7154114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, US9466803,

[0204]

[0205]

[0206]

[0207]

[0208] .

[0209] e) Additional Emitter:

[0210] One or more additional emitter dopants may be used in combination with the compound of the present invention. Examples of additional emitter dopants are not particularly limited, and any compound that is typically used as an emitter material may be used. Examples of suitable emitter materials include, but are not limited to, compounds capable of producing luminescence through phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet quenching, or a combination of these processes.

[0211] Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, US06699599, US06916554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US20070231600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US20080233410, US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663,US20100244004, US20100295032, US2010102716, US2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US2011285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US2014103305, US6303238, US6413656, US6653654, US6670645, US6687266, US6835469, US6921915, US7279704, US7332232, US7378162, US7534505, US7675228, US7728137, US7740957, US7759489, US7951947, US8067099, US8592586, US8871361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.,

[0212]

[0213]

[0214]

[0215]

[0216]

[0217] .

[0218] f) HBL:

[0219] A hole blocking layer (HBL) can be used to reduce the number of holes and / or excitons leaving the emissive layer. The presence of such a blocking layer within the device can lead to significantly higher efficiency and / or longer lifetime compared to similar devices without a blocking layer. Additionally, the blocking layer can be used to confine light emission to a desired area of ​​the OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and / or higher triplet energy than one or more of the hosts closest to the HBL interface.

[0220] In one embodiment, the compound used in the HBL contains the same molecule or functional group as the aforementioned host.

[0221] In another embodiment, the compound used in HBL contains one or more of the following groups in the molecule:

[0222]

[0223] Here, k is an integer from 1 to 20; L 101 is another ligand, and k' is an integer from 1 to 3.

[0224] g) ETL:

[0225] The electron transport layer (ETL) may comprise a material capable of transporting electrons. The electron transport layer may be native (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 may be used as long as it is typically used to transport electrons.

[0226] In one embodiment, the compound used for ETL contains one or more of the following groups in the molecule:

[0227]

[0228] Here, R 101 Ar 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 if it is aryl or heteroaryl, it has a definition similar to that of Ar described above. 1 or Ar 3 has a definition similar to Ar described above. k is an integer from 1 to 20. X 101 To X 108 It is selected from C (including CH) or N.

[0229] In another embodiment, the metal complex used in the ETL includes, but is not limited to, the following chemical formula:

[0230]

[0231] Here, (ON) or (NN) is a 2-bed ligand having a metal coordinated to atoms O, N or N, N; L 101 is another ligand; k' is an integer value ranging from 1 to the maximum number of ligands to which a metal can be attached.

[0232] Non-limiting examples of ETL materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below together with the references disclosing such materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

[0233]

[0234]

[0235] .

[0236] h) Charge Generation Layer (CGL):

[0237] In tandem or stacked OLEDs, the CGL plays an essential role in terms of performance and consists of an n-doped layer and a p-doped layer for injecting electrons and holes, respectively. Electrons and holes are supplied from the CGL and the electrodes. Electrons and holes consumed in the CGL are replenished by electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Conventional CGL materials include n and p conductive dopants used in the transport layer.

[0238] In any of the aforementioned compounds used in each layer of the OLED device, hydrogen atoms may be partially or completely deuterinated. Thus, any specifically listed substituents, e.g., methyl, phenyl, pyridyl, etc., may be in their non-deuterinated, partially deuterinated, and fully deuterinated forms. Likewise, substituent types, e.g., non-deuterinated, alkyl, aryl, cycloalkyl, heteroaryl, etc., may also be in their non-deuterinated, partially deuterinated, and fully deuterinated forms.

[0239] It should be understood that the various embodiments described herein are merely illustrative and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the invention. Accordingly, as will be apparent to those skilled in the art, the claimed invention may include variations derived from the specific embodiments and preferred embodiments described herein. It should be understood that there is no intention to limit the various theories regarding why the invention is effective.

[0240] E. Experimental Section

[0241] Compound I-(R 31 )(R 31 )(R 31 )Synthesis of

[0242] N -(2-nitrophenyl)-[1,1':3',1''-terphenyl]-2,2'',3,3'',4,4'',5,5'',6,6''- d 10-2'-amine Synthesis of: (phenyl- d 5) Boronic acid (28.0 g, 220 mmol), 2,6-dibromo- N (2-nitrophenyl)aniline (39 g, 105 mmol) and potassium carbonate (36.2 g, 262 mmol) were dissolved / suspended in 1,4-dioxane (900 ml) and water (100 ml). After purging the solution with nitrogen for 30 minutes, SPhos-Pd-G2 (0.714 g, 1.048 mmol) was added. The reaction mixture was heated and refluxed for 16 hours. It was partitioned between ethyl acetate and water and extracted with ethyl acetate. The mixture was concentrated to obtain the desired product (79% yield).

[0243] N -(2-nitrophenyl)-[1,1':3',1''-terphenyl]-2,2'',3,3'',4,4'',5,5'',6,6''- d 10-2'-amine Synthesis of: A solution of Pd2(dba)3 (0.123 g, 0.134 mmol) and S-Phos (0.166 g, 0.403 mmol) was stirred in 1,4-dioxane (200 mL) and water (20 mL) and sprayed under nitrogen at room temperature. 2,6-dibromo- N -(2-nitrophenyl)aniline (10 g, 26.9 mmol), N -(2-nitrophenyl)-[1,1':3',1''-terphenyl]-2,2'',3,3'',4,4'',5,5'',6,6''- d 10-2'-amine and potassium carbonate (9.29 g, 67.2 mmol) were added, and the reaction mixture was stirred at 90°C for 16 hours. The reaction mixture was cooled, diluted with toluene (500 mL) and water (200 mL), extracted with toluene, and washed with brine. The crude product was ground in heptane and filtered to obtain a desired product (99% yield).

[0244] N 1-([1,1':3',1''-terphenyl]-2'-il-2,2'',3,3'',4,4'',5,5'',6,6''- d 10) Benzene-1,2-Diamine Synthesis of: N -(2-nitrophenyl)-[1,1':3',1''-terphenyl]-2,2'',3,3'',4,4'',5,5'',6,6''- d 10-2'-amine (753 mg, 2.000 mmol), 10% Pd / C (150 mg, 0.075 mmol), ammonium formate (1 g, 15.86 mmol), and 2-propanol (20 ml) were charged with nitrogen. The reaction mixture was heated at 80°C for 16 hours. The reaction mixture was cooled to room temperature (RT) and filtered through a Celite pad. The product was rinsed with water and air-dried to obtain the desired product (75% yield).

[0245] Compound I-(R 31 )(R 31 )(R 31 ) Synthesis of: N 1-([1,1':3',1''-terphenyl]-2'-yl-2,2'',3,3'',4,4'',5,5'',6,6''-d10)benzene-1,2-diamine (304 mg, 0.877 mmol) was backfilled under vacuum with nitrogen. 1,2-dichlorobenzene (2 ml) in toluene (2.63 ml, 2.63 mmol), N -ethyl- N - Isopropylpropane-2-amine (0.46 ml, 2.63 mmol) and trichloroborane were added at RT and refluxed for 2 days. Specific mass hits (m / z: 1063) were obtained by LC-MS (Liquid Chromatography-Mass Spectrometry) and MALDI (Matrix Assisted Laser Desorption / Ionization). Specific products were isolated using preparative HPLC (High Performance Liquid Chromatography) (3% isolation yield).

[0246]

[0247] Table 1 shows compound I-(R 31 )(R 31 )(R 31Shows the PL spectra of ) at RT and 77 K. The T1 (lowest triplet) energy (405 nm) is determined by the onset of the phosphorescence spectrum at 77 K. The HOMO / LUMO energies are determined by cyclic voltammetry. The HOMO is compound I-(R 31 )(R 31 )(R 31 It is much thinner than carbazole, a commonly used h-type host component that makes it a potentially good hole-aqueous material.

[0248] Solution cyclic voltammetry and differential pulse voltammetry were performed using an H Instruments Model 6201B potentiostat with dimethylformamide anhydrous solvent and tetrabutylammonium hexafluorophosphate as the supporting electrolyte. Glassy carbon, platinum, and silver wires were used as the working, counter, and reference electrodes, respectively. The electrochemical potential was referenced to the internal ferrocene-ferroconium redox couple (Fc / Fc+) by measuring the peak potential difference from differential pulse voltammetry. The corresponding highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies were referenced from the literature [(a) Fink, R.; Heischkel, Y.; Thelakkat, M.; Schmidt, H.-W. Chem. Mater. 1998 , 10 , 3620-3625. (b) Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R.F.; Bassler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995 , 7 The cation and anion redox potentials for ferrocene were determined by referring to [4.8 eV versus vacuum] according to , 551.

Claims

Claim 1 A compound comprising the structure of the following chemical formula I, wherein chemical formula I can be combined with one or more identical structures or polymer compounds: During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; R for each case A is independently a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2 Each is a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any two adjacent R, R 1 , R 2 or R A It can combine or fuse to form a ring. Claim 2 In claim 1, the compound is a compound having the structure of the following chemical formula III: During the meal, L 1 is a linker selected from the group consisting of a 1-atom main chain, a 2-atom main chain, a 3-atom main chain, a 4-atom main chain, a 5-atom main chain, and a 6-atom main chain, and R, R 1 , R 2 and R A is as defined in Paragraph 1. Claim 3 In paragraph 2, the main chain atom is a compound selected from the group consisting of B, N, Si, C, O, S, and P. Claim 4 In paragraph 2, L 1 A compound that is a linker containing a two-atom main chain of B and N atoms. Claim 5 In paragraph 2, L 1 A compound that is a linker containing a 4-atom main chain of 2 B and 2 N atoms. Claim 6 In paragraph 2, 2 Rs A A compound in which substituents bond together to form a fused six-membered aromatic ring. Claim 7 In paragraph 2, the above compound is a compound having the structure of the following chemical formula IV: During the meal, L 2 is a direct linker, or a linker selected from the group consisting of a 1-atom main chain, a 2-atom main chain, a 3-atom main chain, and a 4-atom main chain group, wherein the main chain atoms are selected from B, N, Si, C, O, S, and P; R 5 and R 6 Each is a substituent selected independently from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R, R 1 , R 2 and R A is as defined in paragraph 1; and any two adjacent R, R 1 , R 2 , R 5 , R 6 or R A It can combine or fuse to form a ring. Claim 8 In Paragraph 7, L 2 is a direct coupling between B and N, and R, R 1 , R 2 , R A , R 5 and R 6 ...is as defined in Clause 7, and the compound is a compound having the structure of the following chemical formula V: . Claim 9 In paragraph 8, R 1 or R 6 is an amino or arylamino group, or R 2 or R 5 is a compound of aryl or heteroaryl origin. Claim 10 In claim 1, the compound is a compound that is partially or completely deuteriumized. Claim 11 In paragraph 2, the above compound is a compound having the structure of the following chemical formula VI: During the meal, R 5 , R 6 , R 7 and R 8 Each is independently a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R, R 1 , R 2 and R A is as defined in paragraph 1; and any two adjacent R, R 1 , R 2 , R 5 , R 6 , R 7 , R 8 or R A It can combine or fuse to form a ring. Claim 12 In Paragraph 11, R 1 , R 6 or R 7 is an amino or arylamino group, or R 2 , R 5 or R 8 It is a compound of aryl or heteroaryl origin. Claim 13 In paragraph 2, the compound is a compound selected from the group consisting of the following: During the meal, R A is as defined in Paragraph 1, and R B , R C and R D represents no substitution, identical substitution, or identical substitution for its associated loop, respectively;R B , R C and R D is a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R A' , R B' , R C' and R D' represents no substitution, uniform substitution, or maximum allowed substitution for its associated loop, respectively;R A' , R B' , R C' and R D' is a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R 1' , R 2' , R 3' and R 4' Each is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof. Claim 14 In claim 1, the compound is selected from the group consisting of the following: In the formula, R1 to R70 are compounds having the following structure: . Claim 15 In claim 1, the compound is a compound selected from the group consisting of the following: . Claim 16 In paragraph 15, the above compound is a completely deuteriumized compound. Claim 17 An organic light-emitting device (OLED) comprising an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of the following chemical formula I, and chemical formula I can be combined with one or more identical structures and / or polymer compounds: During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; and R for each case A is independently a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2 Each is a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and any two adjacent R, R 1 , R 2 , or R A It can combine or fuse to form a ring. Claim 18 In paragraph 17, the compound is a host, and the organic layer is an OLED that is a light-emitting layer containing a phosphorescent emitter. Claim 19 In paragraph 18, the phosphorescent emitter is an OLED that is a transition metal complex having at least one ligand selected from the group consisting of the following, or, if the ligand has more than two sites, a portion of the ligand: In the formula, T is B, Al, Ga, In and Y 1 to Y 13 Each is independently selected from the group consisting of carbon and nitrogen; Y' is BR e , NR e , PR e , O, S, Se, C=O, S=O, SO2, CR e R f , SiR e R f and GeR e R f Selected from a group consisting of; R e and R f can fuse or combine to form a ring; and each R a , R b , R c and R d is independently denoted as no substitution, uniform substitution, or substitution up to the maximum allowed number for its associated loops; R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f Each is independently a substituent selected from the group consisting of hydrogen, or deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any two adjacent R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f It can fuse or combine to form a ring or a multidentate ligand. Claim 20 A consumer product comprising an organic light-emitting device (OLED) comprising an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of the following chemical formula I, and chemical formula I can be combined with one or more identical structures or polymer compounds: During the meal, R A represents no substitution, identical substitution, or identical substitution for its related loop; and R for each case A is independently a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; R is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R 1 and R 2 Each is a substituent selected from the group consisting of hydrogen, or deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and any two adjacent R, R 1 , R 2 or R A It can combine or fuse to form a ring.

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