A boron atom-containing carbazole derivative and use thereof

Abstract

The application relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative containing boron atoms and application thereof. The structural formula of the carbazole derivative containing boron atoms is shown as formula (I); the carbazole derivative shown as formula (I) provided by the application has a high triplet energy level, improves the thermal stability and the ability of transporting carriers of the material; the carbazole derivative is applied in an organic electroluminescent element, and the driving voltage can be remarkably reduced, the luminous efficiency and the service life are improved.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, and in particular to a boron-containing carbazole derivative and its applications. Background Technology

[0002] Generally speaking, organic light emission refers to the phenomenon that organic materials emit light when electrical energy is applied to them. That is, when an organic layer is placed between the anode and the cathode, if a voltage is applied between the two electrodes, holes will be injected from the anode into the organic layer, and electrons will be injected from the cathode into the organic layer. When the injected holes and electrons meet, they will form excitons. When the excitons transition to the ground state, they will emit light and heat.

[0003] In recent years, organic light-emitting diode (OLED) display technology has matured, and some products have entered the market. However, many problems still need to be solved in the process of industrialization. In particular, many issues remain unresolved regarding the various organic materials used to fabricate the elements, such as carrier injection and transport performance, electroluminescence properties, lifespan, color purity, and the matching between various materials and electrodes. Especially concerning is that the luminous efficiency and lifespan of the light-emitting elements do not yet meet the requirements for practical application, which greatly limits the development of OLED technology. While triplet-state phosphorescent materials possess high luminous efficiency, and their green and red light materials have met the requirements for use, these materials require matching with phosphorescent materials or hole materials with high triplet energy levels. Therefore, developing phosphorescent materials or hole materials with high triplet energy levels is an urgent need for the current development of OLEDs.

[0004] With current technological advancements, improvements are still needed for both fluorescent and phosphorescent materials, particularly in terms of operating voltage, efficiency, lifetime, and thermal stability during sublimation, especially in their application in organic electroluminescent devices.

[0005] Therefore, in order to overcome the technical problems mentioned above and further improve the characteristics of organic electroluminescent devices, there is a continued demand for the development of more stable and effective substances that can be used as phosphorescent or hole materials in organic electroluminescent devices.

[0006] In view of this, the present invention is proposed. Summary of the Invention

[0007] The purpose of this invention is to provide a boron-containing carbazole derivative that effectively improves the triplet energy level, thermal stability, and carrier transport capability of the material. Organic electroluminescent devices prepared using this carbazole derivative can significantly reduce the driving voltage, improve luminous efficiency, and increase lifetime. Another purpose of this invention is to provide applications of this boron-containing carbazole derivative.

[0008] Specifically, the present invention provides the following technical solutions:

[0009] This invention provides a boron-containing carbazole derivative, the structural formula of which is shown in formula (I):

[0010]

[0011] Among them, ring C and ring D are each independently selected from C6-C. 60 Aryl or C2-C 60 Heterocyclic aryl;

[0012] X 1 X 2 X 3 Each is independently selected from single bonds, o, S, Se, and CR. 5 R 6 SiR 5 R 6 NR 5 Or it may be empty;

[0013] R 1 R 2 R 3 R 4 R 5 R 6 Each is independently selected from hydrogen, deuterium, halogen atom, nitrile group, and C1-C. 40 Alkyl, C3-C 40 Cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Fused aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, substituted or unsubstituted C2-C 60 Groups composed of heterocyclic aryl groups; R 1 R 2 R 3 R 4 Each is replaced by one or more saturated substitutions;

[0014] Ar 1 Choose either freely substituted or unsubstituted C2-C 60 heteroaryl, or substituted or unsubstituted C2-C 60 A group composed of heteroaryl amines;

[0015] n is an integer selected from 0 to 5;

[0016] L 1 Selected from single-bonded, substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C2-C 60 Hybrid aryl.

[0017] In this invention, in the substituted or unsubstituted rings formed by the combination of adjacent groups, "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0018] Preferably, the boron-containing carbazole derivative is selected from the group consisting of the following structures:

[0019]

[0020] Among them, X 1 X 2 X 3 R 1 R 2 R 3 R 4 Ar 1 and L 1 The meaning is the same as the definition of equation (I);

[0021] Preferably, the X 1 X 2 X 3 Each can be independently selected from a single key, O, S, or empty.

[0022] Preferably, the R 1 R 2 R 3 R 4 Each is either hydrogen or deuterium.

[0023] Preferably, the Ar 1 Selected from substituted or unsubstituted C2-C 60 Mixed aromatic compounds.

[0024] In this invention, "aryl" refers to both monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. A polycyclic system may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group; for example, other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. Preferred aryl groups are those containing 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Particularly preferred are aryl groups having six, ten, or twelve carbon atoms. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracene, ferroyl, phenanthryl, fluorenyl, pyrene, perylene, etc. The aryl group is preferably phenyl, biphenyl, terphenyl, triphenylene, fluorenyl, or naphthyl. Additionally, the aryl group may optionally be substituted.

[0025] In this invention, "heteroaryl" refers to a monocyclic aromatic group and a polycyclic aromatic ring system comprising at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases, oxygen, sulfur, or nitrogen are preferred heteroatoms. A monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. A heteropolycyclic system may have two or more rings in which two atoms are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is a heteroaryl group, and other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and / or heteroaryl. A heteropolycyclic aromatic ring system may have one to six heteroatoms on each ring of the polycyclic aromatic ring system. Preferred heteroaryls are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indole-carbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, inoxazine, benzoxazole, benziisoxazole, benzothiazole, quinoline, isoquinoline, cinnamoline, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, oxanthracene ( xanthene), acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophene, selenophenodipyridine, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazynylene and their aza analogs, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazynylene and their aza analogs. Additionally, the heteroaryl group may optionally be substituted.

[0026] The fused aryl group used in this invention refers to a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon with 6 to 60 carbon atoms that has two or more rings. In this case, the two or more rings can be simply attached to each other or attached in a condensed form. Non-limiting examples include phenanthrene, anthracene, fluoranthracene, pyrene, triphenylene, perylene, etc. Base, etc.

[0027] The aromatic amine group used in this invention refers to an amine substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of aromatic amine groups include diphenylamine, N-phenyl-1-naphthylamine, and N-(1-naphthyl)-2-naphthylamine. The heteroaryl amine group refers to an amine substituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms. Non-limiting examples of heteroaryl amine groups include N-phenylpyridin-3-amine, N-([1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine, and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine.

[0028] Preferably, the aryl and heteroaryl groups refer in particular to groups derived from the following substances: phenyl, naphthyl, anthracene, benzanthracene, phenanthryl, pyrene, etc. alkyl, perylene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, triphenylene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans indo[a]carbazoyl, cis or trans indole[a]carbazoyl, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole , isoindolyl, carbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenotoxazinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthiazoleyl, phenanthreneimidazoleyl, pyridinimidazoleyl, pyrazinimidazoleyl, quinoxolinimidazoleyl, oxazolyl, benzoxoxazolyl, naphthiazoleyl, anthraquinoxazolyl, phenanthreneoxazolyl, isoxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexa- Azabenzophenanthryl, benzopyridinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenthiazinyl, fluoresceinyl, naphridinyl, azacarbazolyl, benzocarbazolyl, carbazolyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl , 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purine, pteridine, indazinyl, quinazolinyl, benzothiadiazolyl, or groups derived from combinations of these systems.

[0029] Furthermore, the Ar 1 Choose from the groups consisting of the groups shown in II-1 to II-17 below:

[0030]

[0031] in,

[0032] z1 and z2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amido, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 40Alkyl, C2-C 40 alkenyl, C2-C 40 alkynyl group, C1-C 40 Alkoxy, C3-C 40 Cycloalkanes, C3-C 40 Cycloolefinic, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 arylthio, or substituted or unsubstituted C2-C 60 Groups composed of heteroaryl groups;

[0033] x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5;

[0034] T1 represents O, S, CR'R” or NAr';

[0035] R' and R” are each independently selected from hydrogen, deuterium, and C1 to C2. 40 Alkyl groups, C1-C 40 heteroalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, or substituted or unsubstituted C2-C 60 The group of heteroaryl groups, R' and R" may optionally be joined or fused to form another ring with multiple substituted or unsubstituted rings, the ring containing or not containing one or more heteroatoms N, P, B, O or S; preferably, R' and R" are each independently selected from hydrogen or deuterium;

[0036] Ar' chooses freely from C1 to C. 40 Alkyl groups, C1-C 40 heteroalkyl, C3-C 40 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Fused aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, or substituted or unsubstituted C2-C 60 A group composed of heteroaryl groups.

[0037] Qr 1 Choose from the groups consisting of the groups shown in III-1 to III-13 below:

[0038]

[0039] Wherein, T2 is selected from O or S;

[0040] R14 R 15 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C. 60 Aryl, substituted or unsubstituted C2-C 60 Groups composed of heteroaryl groups;

[0041] R 16 Choose freely from hydrogen, deuterium, C1 to C2. 40 Alkyl, substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C2-C 60 Groups composed of heteroaryl groups; R 16 One or more substitutions to saturation;

[0042] * indicates Ar 1 Substituents and L 1 The connection key.

[0043] The alkyl group used in this invention refers to a monovalent functional group obtained by removing a hydrogen atom from a straight-chain or branched saturated hydrocarbon with 1 to 40 carbon atoms. Non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

[0044] In this invention, a heteroalkyl group refers to an alkyl group in which a hydrogen atom or -CH2- is substituted by at least one heteroatom, wherein the heteroatom is selected from halogens, nitrile groups, N, O, S, or silicon. Non-limiting examples include difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, etc. A haloalkyl group refers to an alkyl group in which a hydrogen atom is partially or completely substituted by a halogen. Non-limiting examples include fluorotoluene, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, etc.

[0045] The alkenyl or ynyl group used in this invention contains at least two carbon atoms. As a non-limiting example, the alkenyl or ynyl group is preferably considered to refer to the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentyynyl, hexynyl, heptenyl, or octyynyl.

[0046] The alkoxy or alkathioyl groups used in this invention are preferably alkoxy or alkathioyl groups having 1 to 40 carbon atoms, and are considered to be methyl methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy, and 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio 2,2,2-trifluoroethylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butenthio, butenoxy, pentenoxy, pententhio, cyclopentenoxy, cyclopententhio, hexenoxy, hexenthio, cyclohexenoxy, cyclohexenthio, acetylenoxy, acetylenthio, propylenoxy, propylenthio, butylenoxy, butylenthio, pentylenoxy, pentylenthio, hexylenoxy, hexylenthio.

[0047] Generally, the cycloalkyl and cycloalkenyl groups according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, or cycloheptenyl, wherein one or more -CH2- groups can be replaced by N, O, or S to form heterocyclic alkyl or heterocyclic alkenyl groups. For example, one -CH2- group in cyclopentyl is replaced by O to form tetrahydrofuranyl, and one -CH2- group in cyclohexyl is replaced by O to form tetrahydropyranyl, etc. In addition, one or more hydrogen atoms can be replaced by deuterium atoms, halogen atoms, or nitrile groups.

[0048] The aryloxy group used in this invention refers to the monovalent functional group represented by R′O-, where R′ is an aryl group with 6 to 60 carbon atoms. Non-limiting examples of such aryloxy groups include phenoxy, naphthoxy, and biphenyloxy groups.

[0049] The aryl thio group used in this invention refers to the monovalent functional group represented by R″S-, where R″ is an aryl group with 6 to 60 carbon atoms. Non-limiting examples of such aryl thio groups include phenylthio, naphthio, and biphenylthio.

[0050] The alkylsilyl group used in this invention refers to a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the alkylsilyl group having at least 3 carbon atoms. Non-limiting examples of alkylsilyl groups include trimethylsilyl and triethylsilyl. The arylsilyl group refers to an alkylsilyl group substituted with at least one aryl group having 6 to 60 carbon atoms. Non-limiting examples include phenyldimethylsilyl, naphthyldimethylsilyl, phenyldiethylsilyl, diphenylmethylsilyl, diphenylethylsilyl, and triphenylsilyl.

[0051] In the context of this invention, "alkyl carbonyl", "alkoxy carbonyl", "aryl carbonyl", "arylboron carbonyl", and "alkylboron carbonyl" refer to the substituted carbonyl group (-COR*), wherein R* is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboron, and alkylboron.

[0052] The arylphospho group used in this invention refers to a diarylphospho group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylphospho groups include diphenylphospho and di(4-trimethylsilylphenyl)phospho. Aryloxophospho is formed when the phosphorus atom of a diarylphospho group is oxidized to its highest valence state.

[0053] The arylboryl group used in this invention refers to a diarylboryl group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylboryl groups include diphenylboryl and di(2,4,6-trimethylphenyl)boryl. Alkylboryl group refers to a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms. Non-limiting examples of alkylboryl groups include di-tert-butylboryl and diisobutylboryl.

[0054] In this invention, arylene refers to a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon with 6 to 60 carbon atoms. Non-limiting examples include phenylene, naphthylene, phenanthrene, anthracene, fluorene, and spirodifluorene.

[0055] In this invention, heteroaryl or hetero-aryl refers to a divalent functional group obtained by removing two hydrogen atoms from a heteroaromatic hydrocarbon with 5 to 60 carbon atoms. Non-limiting examples include pyridyl, quinoline, isoquinoline, carbamoline, pyrimidinyl, and triazineyl.

[0056] Preferably, z1 and z2 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, methyl, tert-butyl, phenyl, naphthyl, phenanthryl, diphenyl, terphenyl, dibenzofuranyl, dibenzothiophene, fluorenyl or carbazole.

[0057] Preferably, T1 is selected from O, S or NAr'.

[0058] Preferably, Ar' is selected from the group consisting of phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, naphthyl, phenanthryl, fluorenyl, spirodifluorenyl or carbazoleyl.

[0059] Preferably, the L 1 Selected from single bonds or groups consisting of groups shown in IV-1 to IV-23 below:

[0060]

[0061] In this context, the dashed lines represent the connection sites of functional groups.

[0062] Preferably, n is selected from 0, 1, or 2.

[0063] As used herein, “combination of” or “group” means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by one of ordinary skill in the art from the applicable list. For example, alkyl and deuterium can be combined to form partially or fully deuterated alkyl groups; halogen and alkyl groups can be combined to form haloalkyl substituents, such as trifluoromethyl; and halogen, alkyl and aryl groups can be combined to form haloaralkyl groups.

[0064] In one instance, the term substitution includes a combination of two to four listed groups.

[0065] In this invention, the terms "halogen", "halogen", "halogen atom", and "halogen group" are used interchangeably and refer to fluorine, chlorine, bromine, or iodine.

[0066] In this invention, the term "substituted or unsubstituted" refers to a group selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy groups, C3-C 60 cycloalkyl, C3-C 60 Cycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy groups, C6-C 60 aryl sulfide group and C2-C 60 The heterocyclic aryl group is substituted or unsubstituted by one or more substituents, or is substituted or unsubstituted by a substituent formed by linking two or more substituents of the substituents exemplified above.

[0067] Preferably, the structural formula of the boron-containing carbazole derivative is selected from the group consisting of C600 to C839:

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] Wherein, *-T2-* is selected from *-O-*, *-S-*, or one of the following structures:

[0080]

[0081] Preferably, the *-T2-* is selected from *-O-*, *-S-*, or one of the following structures:

[0082]

[0083] *- and -* represent connector keys.

[0084] The present invention also provides an organic electroluminescent material, the raw materials of which include the above-mentioned boron-containing carbazole derivatives; the organic electroluminescent material including the boron-containing carbazole derivatives of the present invention has the ability of carrier transport.

[0085] Preferably, the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light-emitting layer material, an electron transport layer material, an electron injection layer material, a CPL layer material, or an electron blocking layer material.

[0086] This invention also provides the application of the boron-containing carbazole derivatives described above in the preparation of organic electroluminescent elements.

[0087] The present invention also provides an organic electroluminescent element, comprising: a first electrode, a second electrode, a CPL layer, and one or more organic layers disposed between the first electrode and the second electrode; at least one of the organic layers and the CPL layer comprises the above-described carbazole derivative containing boron atoms.

[0088] The organic electroluminescent element comprises a cathode, an anode, a CPL (Chemical Polarizing Layer), and at least one emitting layer. In addition to these layers, it may also comprise other layers, such as, in each case, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. An intermediate layer having, for example, exciton blocking functionality may also be introduced between two emitting layers. However, it should be noted that each of these layers is not necessarily required. The organic electroluminescent element described herein may comprise one emitting layer, or it may comprise multiple emitting layers. That is, various luminescent compounds capable of emitting light are used in the emitting layers. A system having three emitting layers is particularly preferred, wherein the three layers can exhibit blue, green, and red light emission. If more than one emitting layer is present, according to the invention, at least one of these layers comprises a compound of the invention.

[0089] Furthermore, the organic electroluminescent element according to the present invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0090] In the other layers of the organic electroluminescent element according to the invention, particularly in the hole transport layer and the light-emitting layer, and in the CPL, all materials can be used in accordance with the manner commonly used in the prior art. Those skilled in the art will therefore be able to use all materials known about organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.

[0091] Furthermore, the following organic electroluminescent elements are preferred, which can be applied with one or more layers by means of a sublimation method, wherein in a vacuum sublimation apparatus at temperatures below 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may be even lower, for example, below 10 Pa. -7 Pa.

[0092] Similarly, the organic electroluminescent element as described below can also be applied by means of organic vapor deposition or by means of carrier gas sublimation, wherein, in 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is therefore structured.

[0093] Furthermore, the following organic electroluminescent elements are preferred, which produce one or more layers from solution, for example by spin coating, or by any desired printing method such as screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, for example, are obtained by means of compounds represented by suitable substitution formula (I). These methods are also particularly suitable for oligomers, dendritic macromolecules, and polymers. Additionally, mixing methods are feasible, in which one or more layers are applied from solution and one or more additional layers are applied by vapor deposition.

[0094] These methods are generally known to those skilled in the art, and they can be applied to organic electroluminescent elements containing compounds according to the present invention without any inventive effort.

[0095] Therefore, the present invention also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and / or by means of an organic vapor deposition method or by means of carrier gas sublimation, and / or by means of spin coating or printing method from a solution to apply at least one layer.

[0096] Furthermore, the present invention relates to compounds comprising at least one of the compounds of the present invention as described above. The same preferred embodiments as noted above regarding organic electroluminescent elements apply to the compounds of the present invention. In particular, the compounds may also preferably contain other compounds. Processing the compounds of the present invention from the liquid phase, for example by spin coating or printing methods, requires formulations for processing the compounds of the present invention, which may be, for example, solutions, dispersions, or emulsions. For this purpose, mixtures of two or more solvents may preferably be used. Suitable and preferred solvents include, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthalene, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methyl anisole, 3,4-dimethyl anisole, 3,5-dimethyl anisole, acetophenone, α-terpenes. Alcohol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-methylisopropylbenzene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentabenzene, hexene, heptene, octene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0097] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a CPL layer, or an electron blocking layer.

[0098] Preferably, the light-emitting layer comprises a boron-containing carbazole derivative as described in this invention.

[0099] The present invention also provides a consumer product comprising the organic electroluminescent element described above.

[0100] In addition, unless otherwise specified, all raw materials used in this invention can be obtained commercially available. Any range described in this invention includes the end value and any value between the end values, as well as any subrange formed by the end value or any value between the end values.

[0101] The beneficial effects achieved by this invention are as follows:

[0102] The boron-containing carbazole derivative shown in formula (I) provided by this invention utilizes boron-nitrogen and boron-oxygen resonance effects to improve the triplet stability and carrier transport capability of the carbazole derivative. Applying this carbazole derivative to organic electroluminescent devices can significantly reduce the driving voltage and improve luminous efficiency and lifetime. Attached Figure Description

[0103] Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. The diagram is not necessarily drawn to scale. Device 100 may include a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode layer 110, and a capping layer (cPL) 111. Device 100 can be fabricated by sequentially depositing the described layers.

[0104] Figure 2 A schematic diagram of an organic light-emitting device 200 with two light-emitting layers is shown. The device includes a substrate 201, an anode layer 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode layer 213. The device 200 can be fabricated by sequentially depositing the described layers. Because most common OLED devices have one light-emitting layer, and device 200 has a first light-emitting layer and a second light-emitting layer, the emission peaks of the first and second light-emitting layers can be overlapping, cross-overlapping, or non-overlapping. Materials similar to those described with respect to device 100 can be used in the corresponding layers of device 200. Figure 2 Provides an example of how to add layers from the structure of device 100. Detailed Implementation

[0105] The following examples are used to illustrate the present invention, but are not intended to limit the scope of the invention.

[0106] In the description of this invention, unless otherwise stated, "a plurality of" means two or more; the terms "upper," "lower," etc., indicate the orientation or positional relationship based on the orientation or positional relationship shown in the drawings, and are only for the convenience of describing the invention and simplifying the description, and do not indicate or imply that the device or element referred to must have a specific orientation, or be constructed and operated in a specific orientation, and therefore should not be construed as a limitation of the invention.

[0107] Unless otherwise specified, the experimental methods used in the following embodiments are conventional methods. Unless otherwise specified, the experimental materials and related equipment used in the following embodiments are commercially available, and all percentages are by mass.

[0108] The following embodiments use the following testing instruments and methods for performance testing of OLED materials and components:

[0109] OLED component performance testing conditions:

[0110] Luminosity and chromaticity coordinates: tested using a PhotoResearch PR-715 spectral scanner;

[0111] Current density and turn-on voltage: tested using a Keithley 2420 digital source meter;

[0112] Power efficiency: Tested using NEWPORT 1931-C.

[0113] Example 1

[0114] The preparation method of compound C613 includes the following steps:

[0115] Step 1: Preparation of intermediate Int-1

[0116]

[0117] 20.0 mmol of 4-bromo-3-hydroxycarbazole, 22.0 mmol of 3-phenoxyphenylboronic acid, 20.0 mmol of anhydrous copper acetate, and 100 mL of 1,2-dichloroethane were added, followed by the addition of 40.0 mmol of triethylamine. The mixture was stirred at room temperature for 24 hours, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give compound Int-1 as a yellow solid, yield: 74%.

[0118] Step 2: Preparation of intermediate Int-2

[0119]

[0120] Under nitrogen protection, 20.0 mmol of Int-1 was dissolved in 60 mL of dry xylene and 20 mL of dry THF. The solution was cooled to -78 °C with liquid nitrogen, and 25.0 mmol of 2.5 M n-lithium hexane solution was added dropwise. The mixture was stirred for 10 minutes, followed by the addition of 24.0 mmol of boron triiodide. The mixture was then heated to room temperature and stirred for 1 hour. 40.0 mmol of diisopropylethylamine was added, and the mixture was stirred and heated to reflux. During this process, low-boiling solvents were evaporated. The reaction was carried out for 12 hours, cooled to room temperature, and 20 mL of water was added dropwise. The organic phase was separated, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give compound Int-2 as a yellow solid, with a yield of 57%.

[0121] Step 3: Preparation of compound C613

[0122]

[0123] Under nitrogen protection, 20.0 mmol of Int-2 was dissolved in 80 mL of dry THF, cooled to 0 °C, and 24.0 mmol of 60% sodium hydride solid was added in portions. The mixture was stirred for 1 hour, then 24.0 mmol of 2-([1,1′-biphenyl]-3-yl)-3-chloroquinoxaline was added, and the mixture was heated to room temperature and stirred for 15 hours. 50 mL of water was added dropwise, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was collected, dried, concentrated under reduced pressure, and purified by silica gel column chromatography to give compound C613 as a yellow solid, yield: 76%, MS (TOF): m / z = 640.2134 [M+H]. + .

[0124] Following a similar synthetic method described above, the compounds shown in Table 1 were prepared:

[0125] Table 1

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] Example 2

[0134] The preparation method of compound C694 includes the following steps:

[0135] Step 1: Preparation of intermediate Int-3

[0136]

[0137] Under nitrogen protection, 20.0 mmol of 1-bromo-7H-benzo[c]carbazole was dissolved in 50 mL of DMF, and 22.0 mmol of N-iodosuccinimide was added in portions. The mixture was stirred for 2 hours, and the reaction solution was poured into 150 mL of water. The mixture was filtered, the filter cake was washed with water, dried, and purified by silica gel column chromatography to give compound Int-3 as a yellow solid with a yield of 93%.

[0138] Step 2: Preparation of intermediate Int-4

[0139]

[0140] Under nitrogen protection, 24.0 mmol of phenol was dissolved in 50 mL of dry DMF, cooled to 0 °C, and 29.0 mmol of 60% sodium hydride solid was added in portions. The mixture was stirred for 1 hour, then 20.0 mmol of Int-3 and 2.0 mmol of cuprous iodide were added. The mixture was stirred and heated to 150 °C for 12 hours. After cooling to room temperature, the reaction solution was poured into 150 mL of water, filtered, the filter cake was washed with water, dried, and purified by silica gel column chromatography to give compound Int-4 as a yellow solid, yield: 65%.

[0141] Step 3: Preparation of intermediate Int-5

[0142]

[0143] Under nitrogen protection, 20.0 mmol of Int-4 was dissolved in 40 mL of dry xylene and 40 mL of dry THF. The solution was cooled to -78 °C with liquid nitrogen, and 25.0 mmol of 2.5 M n-lithium hexane solution was added dropwise. The mixture was stirred for 10 minutes, followed by the addition of 24.0 mmol of boron triiodide. The mixture was stirred for 1 hour, and then 40.0 mmol of triethylamine was added. The mixture was stirred and heated to 140 °C, during which time low-boiling solvents were evaporated. The reaction was carried out for 12 hours, cooled to room temperature, and 20 mL of water was added dropwise. The organic phase was separated, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give compound Int-5 as a yellow solid, with a yield of 62%.

[0144] Step 4: Preparation of compound C694

[0145]

[0146] Under nitrogen protection, 20.0 mmol of Int-5 was dissolved in 50 mL of dry DMF. The mixture was cooled to 0 °C, and 22.0 mmol of sodium hydride solid was added in portions. The mixture was stirred for 1 hour, followed by the addition of 22.0 mmol of 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine. The mixture was heated to 55 °C and stirred for 12 hours. The reaction mixture was poured into 150 mL of water, filtered, and the filter cake was washed with water, dried, and purified by silica gel column chromatography to give compound C694 as a yellow solid. Yield: 83%. MS (TOF): m / z = 599.2047 [M+H] + .

[0147] Following a similar synthetic method described above, the compounds shown in Table 2 were prepared:

[0148] Table 2

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] Example 3

[0155] The preparation method of compound C771 includes the following steps:

[0156] Step 1: Preparation of intermediate Int-6

[0157]

[0158] Following the synthesis method of step 2 in Example 2, except that Int-3 in step 2 of Example 2 was replaced with 5-bromo-3-iodocarbazole, compound Int-6 was prepared with a yield of 70%.

[0159] Step 2: Preparation of intermediate Int-7

[0160]

[0161] Under nitrogen protection, 20.0 mmol of Int-6, 22.0 mmol of o-bromophenylboronic acid, 0.01 mmol of Pd(PPh3)4 catalyst, 40.0 mmol of anhydrous sodium carbonate, 50 mL of toluene, 20 mL of ethanol, and 20 mL of water were added. The mixture was heated to reflux and stirred for 15 hours, then cooled to room temperature. 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was collected, dried, concentrated under reduced pressure, and purified by silica gel column chromatography to give compound Int-7 as a yellow solid, yield: 75%.

[0162] Step 3: Preparation of compound Int-8

[0163]

[0164] Under nitrogen protection, 20.0 mmol of Int-7 was dissolved in 60 mL of dry xylene and 40 mL of dry THF. The solution was cooled to -78 °C with liquid nitrogen, and 25.0 mmol of 2.5 M n-lithium hexane solution was added dropwise. The mixture was stirred for 10 minutes, followed by the addition of 24.0 mmol of boron triiodide. The mixture was then heated to room temperature and stirred for 1 hour. 40.0 mmol of tributylamine was added, and the mixture was heated to 140 °C with stirring, during which low-boiling solvents were evaporated. The reaction was carried out for 12 hours, cooled to room temperature, and 20 mL of saturated ammonium chloride aqueous solution was added dropwise. The organic phase was separated, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give compound Int-8 as a yellow solid, with a yield of 64%.

[0165] Step 4: Preparation of compound C771

[0166]

[0167] Following the synthetic method in step four of Example 2, Int-5 was replaced with Int-8, and 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4-phenylbenzo[h]quinazoline, yielding compound C771, a yellow solid, in 77% yield. MS (TOF): m / z = 598.2106 [M+H] + .

[0168] Following a similar synthetic method as described above, the compounds shown in Table 3 were prepared:

[0169] Table 3

[0170]

[0171]

[0172] Example 4

[0173] The preparation method of compound C793 includes the following steps:

[0174] Step 1: Preparation of intermediate Int-9

[0175]

[0176] Under nitrogen protection, 20.0 mmol of 4,5-dibromocarbazole, 22.0 mmol of 3-phenoxyphenylboronic acid, 0.01 mmol of Pd(PPh3)4 catalyst, 40.0 mmol of anhydrous sodium carbonate, 50 mL of toluene, 20 mL of ethanol, and 20 mL of water were added. The mixture was heated to reflux and stirred for 12 hours, then cooled to room temperature. 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was collected, dried, concentrated under reduced pressure, and purified by silica gel column chromatography to give compound Int-9 as a yellow solid, yield: 78%.

[0177] Step 2: Preparation of intermediate Int-10

[0178]

[0179] Under nitrogen protection, 20.0 mmol of Int-9 was dissolved in 60 mL of dry xylene and 40 mL of dry THF. The solution was cooled to -78 °C with liquid nitrogen, and 25.0 mmol of 2.5 M n-lithium hexane solution was added dropwise. The mixture was stirred for 10 minutes, followed by the addition of 24.0 mmol of boron triiodide. The mixture was then heated to room temperature and stirred for 1 hour. 40.0 mmol of triethylamine was added, and the mixture was heated to 140 °C with stirring, during which low-boiling solvents were evaporated. The reaction was carried out for 12 hours, cooled to room temperature, and 20 mL of saturated ammonium chloride aqueous solution was added dropwise. The organic phase was separated, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to give compound Int-10 as a yellow solid, with a yield of 66%.

[0180] Step 3: Preparation of compound C793

[0181]

[0182] Following the synthetic method in step four of Example 2, Int-5 was replaced with Int-10, and 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4-biphenylquinazoline, yielding compound C793, a yellow solid, in 75% yield. MS (TOF): m / z = 624.2185 [M+H] + .

[0183] Following a similar synthetic method described above, the compounds shown in Table 4 were prepared:

[0184] Table 4

[0185]

[0186]

[0187]

[0188]

[0189] Example 5: Preparation of compound C835:

[0190]

[0191] Under nitrogen protection, 20.0 mmol of Int-10, 22.0 mmol of 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 0.2 mmol of Pd2(dba)3 catalyst, 30.0 mmol of sodium tert-butoxide, 0.4 mmol of 30% tri-tert-butylphosphine toluene solution, and 60 mL of xylene were added. The mixture was heated to 110 °C and stirred for 15 hours. After cooling to room temperature, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, and the organic phase was collected, dried, concentrated under reduced pressure, and purified by silica gel column chromatography to give compound C835 as a yellow solid, yield: 86%. MS (TOF): m / z = 651.2296 [M+H] + .

[0192] Following a similar synthetic method described above, the compounds shown in Table 5 were prepared:

[0193] Table 5

[0194]

[0195]

[0196] In the above embodiments, *-T2-* is selected from *-O-*, *-S-*, or one of the following structures:

[0197]

[0198] Example 6

[0199] An organic electroluminescent device 100, the structure of which is as follows: Figure 1 As shown, the device includes a substrate 101, an anode layer 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The fabrication method of the device, omitting the hole blocking layer 107, includes the following steps:

[0200] 1) The glass substrate coated with the ITO conductive layer was ultrasonically treated in the cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in the acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with a UV cleaner for 10 minutes, and bombarded with a low-energy cation beam.

[0201] 2) Place the prepared ITO glass substrate into a vacuum chamber and evacuate to a vacuum level less than 1 × 10⁻⁶. -5 Pa, metallic silver is deposited as the anode layer on the above ITO film, and the thickness of the deposited film is [missing information]. Vaporized compounds HI01 and HI102 were used as hole injection layers, wherein HI102 accounted for 3% of the mass of HI01, and the vapor-deposited film thickness was [missing information].

[0202] 3) The compound HTM is then deposited onto the aforementioned hole injection layer as a hole transport layer, with a deposition thickness of [missing information].

[0203] 4) Further depositing compound EBM as an electron blocking layer on the aforementioned hole transport layer, with a film thickness of [missing information].

[0204] 5) The carbazole derivative of this invention, formula (I), as the host material and RD010 as the dopant material, of this invention are further deposited on the electron blocking layer as an organic light-emitting layer. The deposited film thickness is [missing information].

[0205] 6) A LiQ and ETO6 layer is deposited on the organic light-emitting layer as an electron transport layer, with a LiQ to ETO6 mass ratio of 50:50, and the deposited film thickness is...

[0206] 7) A LiF layer is deposited on top of the electron transport layer as an electron injection layer, with a deposition thickness of [missing information].

[0207] 8) Magnesium and silver are vapor-deposited as a transparent cathode layer on top of the electron injection layer, with a magnesium to silver mass ratio of 1:10, and the vapor-deposited film thickness is [missing information].

[0208] 9) An NPB layer is deposited on top of the transparent cathode layer as the CPL layer of the element, with a deposition thickness of [missing information]. The OLED element provided by this invention is obtained.

[0209] The structures of the compounds HI01, HI102, HTM, EBM, RD010, ET06, and LiQ used in Example 6 are as follows:

[0210]

[0211] Example 7

[0212] An organic electroluminescent device 200, the structure of which is as follows: Figure 2As shown, the device includes a substrate 201, an anode layer 202, a hole injection layer 203, a hole transport layer 204, a first light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light-emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode layer 213. The device 200 can be fabricated by sequentially depositing the described layers. Because the most common OLED devices have one light-emitting layer, and the device 200 has a first light-emitting layer and a second light-emitting layer, the emission peaks of the first and second light-emitting layers can be overlapping, cross-overlapping, or non-overlapping. Materials similar to those described with respect to device 100 can be used in the corresponding layers of the device 200.

[0213] Comparative Example 1

[0214] Following the same steps as in Example 6, the compound shown in formula (I) in step 5) was replaced with B-1 to obtain comparative element 1; the structural formula of B-1 is as follows:

[0215]

[0216] Comparative Example 2

[0217] Following the same steps as in Example 6, the compound shown in formula (I) in step 5) was replaced with B-2 to obtain comparative element 2; the structural formula of B-2 is as follows:

[0218]

[0219] The performance test data of the obtained components were normalized based on comparison component 1, and the results are listed in Table 6. The driving voltage and luminous efficiency were calculated at a current density of 10 mA / cm². 2 Under these conditions, the LT95% lifetime of the component is determined to be at a current density of 50 mA / cm². 2 It was measured under the following conditions.

[0220] The organic electroluminescent devices prepared in Examples 6, 7, Comparative Example 1, and Comparative Example 2 were subjected to performance testing. Specifically, the voltage was increased at a rate of 0.1V per second, and the luminance of the organic electroluminescent device was measured when it reached 1000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the LT90% lifespan test is as follows: using a luminance meter at 1000 cd / m² 2 At a constant current under the given brightness, the brightness decay of the organic electroluminescent element was measured to be 900 cd / m². 2 The time is in hours. The data listed in Table 6 are relative to Comparative Example 1 (data in parentheses are measured data). The results are shown in Table 6.

[0221] Table 6 Performance test results of each component

[0222]

[0223]

[0224]

[0225]

[0226]

[0227] Where Ph is phenyl and FR is 9,9-fluorenyl.

[0228] As shown in Table 6, the light-emitting element prepared using the boron-containing carbazole derivative of the present invention as the main material of the light-emitting layer also achieves a light-emitting efficiency of 10 mA / cm². 2 Under the same conditions, the driving voltage is lower than that of B-1 and B-2, the luminous efficiency is higher, and the LT90% lifetime performance is excellent, indicating that the exciton transport performance and stability of the compound are improved, making it a high-performance luminescent material.

[0229] Although the present invention has been described in detail above with general descriptions and specific embodiments, modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, all such modifications or improvements made without departing from the spirit of the present invention fall within the scope of protection claimed by the present invention.

Claims

1. A carbazole derivative containing a boron atom, characterized by, The carbazole derivative is selected from the following structures: ； Among them, X 1 X 2 Each is independently selected from a single bond, O, or empty, and X 1 X 2 Not both can be empty at the same time; The R 1 R 2 R 3 R 4 Each is either hydrogen or deuterium; Ar 1 is selected from the group consisting of the following groups III-1 to III-13: 、 、 、 、 、 、 、 、 、 、 、 、 ； Wherein, T2 is selected from O or S; R 14 , R 15 are each independently selected from the group consisting of hydrogen, deuterium, C6-C10aryl, or C2-C10heteroaryl; 60 C6-C10aryl, or C2-C10heteroaryl; 60 C6-C10aryl, or C2-C10heteroaryl; R 16 selected from hydrogen, deuterium, Ci-C 40 alkyl, C6-C 60 aryl or C2-C 60 heteroaryl; R 16 is one or more to saturated substitutions; *— indicates Ar 1 Substituents and L 1 The connection key; The L 1 Selected from single bonds or groups shown in IV-1 to IV-23 below: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ； In this context, the dashed lines represent the bonding sites of functional groups.

2. A carbazole derivative containing a boron atom, characterized by, The structural formula of the carbazole derivative is selected from the following structures: Wherein, *—T2—* is selected from *—O—*, *—S—* or one of the following structures: 、 、 ； *— and —* represent connector keys.

3. An organic electroluminescent material, characterized in that, Its raw materials include the boron-containing carbazole derivatives as described in claim 1 or 2.

4. An organic electroluminescent element characterized by comprising the compound according to claim 1. It includes: A first electrode, a second electrode, a CPL layer, and one or more organic layers disposed between the first electrode and the second electrode; At least one of the organic layer and the CPL layer comprises the boron-containing carbazole derivative as described in claim 1 or 2.

5. The organic electroluminescent element according to claim 4, wherein The organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a CPL layer, or an electron blocking layer; the light-emitting layer includes the boron-containing carbazole derivative as described in claim 1 or 2.

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