Boron-containing resonance type organic compound and organic electroluminescent device containing same

Abstract

The invention relates to a boron-containing resonance type organic compound and an organic electroluminescent device containing the same, and belongs to the technical field of semiconductor materials. The structure of the boron-containing resonance type organic compound is shown as a general formula (A). When the boron-containing resonance type organic compound is used as a doping material in a light-emitting layer material of an organic electroluminescent device, the boron-containing resonance type organic compound can be used as a green light doping material of the light-emitting layer of the organic electroluminescent device, so that the light-emitting efficiency of the device is improved, and the service life of the device is prolonged.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of semiconductor materials, and in particular to a boron-containing resonance organic compound and an organic electroluminescent device comprising the same. BACKGROUND

[0002] Compared with liquid crystal display (LCD), organic light-emitting diode (OLED) has the technical advantages of lighter and thinner, high color contrast, low power consumption, fast response, high definition, and flexibility, and is considered to dominate the future display terminal products. With the advent of the 5G era, the new information display industry urgently needs to develop iteratively, and the early lower color gamut standards (BT.709 and DCIP3) cannot meet the high-quality technical development needs of display products. To achieve the performance requirements of ultra-high definition and higher picture quality of display products, the new generation of display standards (BT.2020) drive the development of organic electroluminescent materials towards high color purity, which requires core light-emitting materials to have a narrower emission spectrum. Among the three color display technologies of commercially available OLEDs, blue light uses the traditional fluorescent three triplet-three triplet conversion (TTF) technology, which has a low efficiency but a high color purity and has basically met the BT.2020 display index; green light and red light use phosphorescent light-emitting technology, which has a high efficiency, and red light has approached the BT.2020 display index. However, green light is limited by the relatively wide emission spectrum of phosphorescent light, and there is a large difference between the high shoulder peak of green phosphorescent light and the high-definition display index requirement. Therefore, it is relatively difficult to improve the color gamut display under the traditional device structure, and thus it is very crucial to develop a new generation of high-color-purity green organic electroluminescent material.

[0003] Since 2020, narrow half-peak width green light materials (half-peak width < 30 nm) based on boron-nitrogen resonance structures have been reported one after another, and from 2022 to 2023, a number of green boron-nitrogen narrow emission materials and device effects have been reported: DOI: 10.1002 / anie.202301930, DOI: 10.1038 / s41566-022-01106-8, DOI: 10.1002 / anie.202313254, DOI: 10.1038 / s41566-022-01083-y, DOI: 10.1002 / anie.202202380, etc., which exhibit high color purity and efficiency, and have great potential as a new generation of green organic electroluminescent display materials. However, there are still many technical difficulties in the development of green light ultra-high color purity materials containing boron-nitrogen structures, and the existing materials also have defects such as efficiency and service life that cannot meet the needs of mass production. Therefore, it is a key technical point to develop boron-nitrogen resonance structure-based narrow half-peak width green light materials that can meet actual application requirements, in order to face the next generation of display devices with high color purity, high color gamut coverage, high efficiency, and high immersion.

[0004] In addition, the sensitization technology combines the triplet exciton sensitization material (including but not limited to TADF material and phosphorescent material) with the fluorescent dopant material, uses the triplet exciton sensitization material as an exciton sensitization medium, fully utilizes the triplet exciton, and transfers the energy to the fluorescent dopant material through energy transfer, so that the device internal quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4) can also reach 100%, which can make up for the shortcomings of insufficient utilization of excitons of the fluorescent dopant material, effectively play the characteristics of high fluorescent quantum yield, high device stability, high color purity and low cost of the fluorescent dopant material, and has broad prospects in OLEDs application. In CN 107507921A and CN 110492006A, a combination technology of a light-emitting layer containing a TADF material with a lowest singlet and a lowest triplet energy level difference less than or equal to 0.2eV as a host and a boron-containing material as a dopant is disclosed; and in CN 110492005A and CN 110492009A, a combination scheme of a light-emitting layer containing a boron-containing material as a dopant and a host of an exciplex is disclosed; both of which can achieve an efficiency comparable to phosphorescence and a relatively narrow half peak width. Therefore, the development of a sensitization technology based on a boron-containing light-emitting material with a narrow half peak width has unique advantages and strong potential in the face of BT.2020 display indicators. SUMMARY

[0005] In view of the above problems existing in the prior art, the present application provides a boron-containing resonant organic compound and an organic electroluminescent device comprising the same, and the compound of the present application can realize green light emission.

[0006] The technical scheme provided by the present application is as follows: a boron-containing resonant organic compound, the structure of the boron-containing resonant organic compound is shown in general formula (A):

[0007]

[0008] In general formula (A), ring A is represented by the structure shown in general formula (A-1);

[0009] X is represented by one of a carbon atom or a silicon atom;

[0010] M1, M2, M3, M4, M5, and M6 are independently represented by one of a C6-C30 aromatic ring substituted or unsubstituted by one or more R, or a C2-C30 heteroaromatic ring substituted or unsubstituted by one or more R;

[0011] R represents, the same or different at each occurrence, one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C10 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted borane group;

[0012] R is substituted by a single bond or a ring connection;

[0013] Ar1, Ar2 respectively independently represents one of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C10 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C10 silyl group;

[0014] R1, R2, R3 respectively independently represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C10 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted borane group, a substituted or unsubstituted C3-C10 silyl group;

[0015] Any two of R1, R2 and R3 are not connected or connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c )-, -Si(R d R e )- or -C(R p )=C(R q )- into a ring;

[0016] M1 and R3 are not connected or connected by a single bond, a double bond, -O-, -S-, -N(R a )-, -C(R b R c)-、-Si(R d R e - or -C(R) p )=C(R q - Connect into a loop;

[0017] The R a R b R c R d R e R p R q Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C5-C 10 aryloxy group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane;

[0018] The R b and R c They are either not connected or connected in a loop by a single key;

[0019] The R d and R e They are either not connected or connected in a loop by a single key;

[0020] The substituents used for the substituents are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0021] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0022] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (1) to (4):

[0023]

[0024] In General Formula (1), General Formula (2), General Formula (3), and General Formula (4), M1, M2, M3, M4, M5, M6, Ar1, Ar2, X, R1, R2, and R3 are as defined in General Formula (A).

[0025] Y represents one of a carbon atom or a silicon atom;

[0026] M7and M8independently represent one of a C6to C30aromatic ring substituted with one or more R or unsubstituted, a C2to C30heteroaromatic ring substituted with one or more R or unsubstituted;

[0027] Each occurrence of R, which is the same or different, represents one of a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1to C10alkyl group, a substituted or unsubstituted C3to C10cycloalkyl group, a substituted or unsubstituted C2to C10alkenyl group, a substituted or unsubstituted C2to C10alkynyl group, a substituted or unsubstituted C1to C10alkoxy group, a substituted or unsubstituted C1to C10aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6to C30aryl group, a substituted or unsubstituted C2to C30heteroaryl group, a substituted or unsubstituted borane group, or a substituted or unsubstituted C3to C10silyl group;

[0028] R is substituted with a single bond or a fused ring;

[0029] The substituents for the substituent group are optionally one or more of a deuterium atom, a halogen atom, a cyano group, a C1to C10alkyl group, a deuterium-substituted C1to C10alkyl group, a C6to C30aryl group, a deuterium-substituted C6to C30aryl group, a C5to C30heteroaryl group, and a deuterium-substituted C2to C30heteroaryl group;

[0030] The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, and B.

[0031] Further, the boron-containing resonance-type organic compound has a structure as represented by any one of General Formula (5) to General Formula (8):

[0032]

[0033] In General Formula (5) to General Formula (8), M1, M2, Ar1, Ar2, X, R1, R2, and R3 are as defined in General Formula (A).

[0034] Y represents one of a carbon atom or a silicon atom;

[0035] M7and M8independently represent one of a C6to C30aromatic ring substituted with one or more R or unsubstituted, a C2to C30heteroaromatic ring substituted with one or more R or unsubstituted;

[0036] The R, whether appearing the same or different each time, is represented by one of the following: deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 alkenyl group, substituted or unsubstituted C2-C10 alkoxy group, substituted or unsubstituted C1-C10 aryloxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted boraneyl group, and substituted or unsubstituted C3-C10 silaneyl group.

[0037] The replacement of R is either a single bond or a parallel ring connection;

[0038] Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-(R0);

[0039] The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One or more of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0040] The substituents used for the substituents are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0041] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si, and B.

[0042] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (9) to (18):

[0043]

[0044] In general formulas (9) to (18), the definitions of Ar1, Ar2, X, R1, R2, and R3 are the same as those in general formula (A);

[0045] Y represents either a carbon atom or a silicon atom;

[0046] Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-(R0);

[0047] The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0048] The substituents used for the substituents are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0049] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0050] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (19) to (34):

[0051]

[0052]

[0053] In general formulas (19)-34, the definitions of Ar1, Ar2, R1, and R2 are the same as those in general formula (A);

[0054] Y represents either a carbon atom or a silicon atom;

[0055] Each occurrence of Z that is independent is represented as N, C-(H), or C-(R0);

[0056] The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C5-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0057] The substituents used for the substituents are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0058] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0059] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (35) to (38):

[0060]

[0061] In general formulas (35)-(38), the definitions of M1, M2, Ar1, Ar2, R1, R2, and R3 are the same as those in general formula (A);

[0062] Y represents either a carbon atom or a silicon atom;

[0063] Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-(R0);

[0064] The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0065] The substituents used for the substituents are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0066] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0067] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (39) to (42):

[0068]

[0069] In general formulas (39)-42, the definitions of Ar1, Ar2, R1, R2, and R3 are the same as those in general formula (A);

[0070] Y represents either a carbon atom or a silicon atom;

[0071] R'1, R'2, R'3, and R'4 are each independently represented as one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 alkenyl group, substituted or unsubstituted C2-C10 alkoxy group, substituted or unsubstituted C6-C10 aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted boroalkyl group, and substituted or unsubstituted C3-C10 silyl group.

[0072] Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-(R0);

[0073] The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0074] The substituents used for the substituents are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl.

[0075] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0076] Furthermore, each of M1-M8 is independently represented by one or more R-substituted or unsubstituted groups of the following: phenyl, naphthyl, anthracene, phenanthryl, pyridinyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, spirofluorenyl;

[0077] R and R0 are independently represented as a deuterium atom, a halogen atom, a cyano group, a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), an anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), and a group substituted or unsubstituted. Unsubstituted pyridyl, quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spiroyl (substituted or unsubstituted) Fluorenyl, amino group substituted or unsubstituted, triazine group substituted or unsubstituted, propyl group substituted or unsubstituted, butyl group substituted or unsubstituted, isobutyl group substituted or unsubstituted, sec-butyl group substituted or unsubstituted, neopentyl group substituted or unsubstituted, n-pentyl group substituted or unsubstituted, isopentyl group substituted or unsubstituted, tert-pentyl group substituted or unsubstituted, 1-methylpentyl group substituted or unsubstituted, 2-methylpentyl group substituted or unsubstituted, 3-methylpentyl group substituted or unsubstituted, and so on. One of the following: unsubstituted 1-butylpentyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted tert-butyldimethylsilyl;

[0078] The R1, R2, R3, R a R b R c R d R e R p R qEach of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), and [other groups are listed separately]. Pyridyl, quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorene (substituted or unsubstituted). The following groups are listed: amino group (substituted or unsubstituted), triazine group (substituted or unsubstituted), propyl group (substituted or unsubstituted), butyl group (substituted or unsubstituted), isobutyl group (substituted or unsubstituted), sec-butyl group (substituted or unsubstituted), neopentyl group (substituted or unsubstituted), n-pentyl group (substituted or unsubstituted), isopentyl group (substituted or unsubstituted), tert-pentyl group (substituted or unsubstituted), 1-methylpentyl group (substituted or unsubstituted), 2-methylpentyl group (substituted or unsubstituted), 3-methylpentyl group (substituted or unsubstituted), and so on. One of the following: unsubstituted 1-butylpentyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted tert-butyldimethylsilyl;

[0079] Ar1 and Ar2 represent hydrogen atoms, deuterium atoms, halogen atoms, methyl groups (substituted or unsubstituted), ethyl groups (substituted or unsubstituted), isopropyl groups (substituted or unsubstituted), tert-butyl groups (substituted or unsubstituted), cyclohexyl groups (substituted or unsubstituted), adamantyl groups (substituted or unsubstituted), phenyl groups (substituted or unsubstituted), diphenyl groups (substituted or unsubstituted), terphenyl groups (substituted or unsubstituted), naphthyl groups (substituted or unsubstituted), anthracene groups (substituted or unsubstituted), phenanthryl groups (substituted or unsubstituted), and other substituents. Substituted pyridyl, quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorene (substituted or unsubstituted). The following groups are listed: amino group (substituted or unsubstituted), triazine group (substituted or unsubstituted), propyl group (substituted or unsubstituted), butyl group (substituted or unsubstituted), isobutyl group (substituted or unsubstituted), sec-butyl group (substituted or unsubstituted), neopentyl group (substituted or unsubstituted), n-pentyl group (substituted or unsubstituted), isopentyl group (substituted or unsubstituted), tert-pentyl group (substituted or unsubstituted), 1-methylpentyl group (substituted or unsubstituted), 2-methylpentyl group (substituted or unsubstituted), 3-methylpentyl group (substituted or unsubstituted), and so on. One of the following: unsubstituted 1-butylpentyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted tert-butyldimethylsilyl;

[0080] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, and diphenylamino.

[0081] Furthermore, R'1, R'2, R'3, and R'4 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), and so on. Unsubstituted phenanthrene, pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), and others. Specified or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazine, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted neopentyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted isopentyl, substituted or unsubstituted tert-pentyl, substituted or unsubstituted 1-methylpentyl, substituted or unsubstituted 2-methylpentyl, substituted or unsubstituted 3-methylpentyl, substituted or unsubstituted... One of the following: 1-butylpentyl (substituted or unsubstituted), 2-methylbutyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiopheneyl (substituted or unsubstituted), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl (substituted or unsubstituted), diphenylamino (substituted or unsubstituted), indolyl (substituted or unsubstituted), benzoindolyl (substituted or unsubstituted), trimethylsilyl (substituted or unsubstituted), and tert-butyldimethylsilyl (substituted or unsubstituted).

[0082] Furthermore, R and R0 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl The substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, diphenylamino;

[0083] The R1, R2, R3, R a R b R c R d R e R p R qEach of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl One of the following: isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, and diphenylamino.

[0084] Ar1 and Ar2 are represented as methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted One of the following: phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl;

[0085] The M1-M8 groups represent phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, and methyl-substituted... One of the following: diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, oxanthoneyl, and phenyl-substituted triazineyl;

[0086] The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, and diphenylamino.

[0087] Preferably, the M1 and M2 rings are represented by the following groups:

[0088] Any one of them;

[0089] Preferably, the M3, M4, M5, M7, and M8 rings are represented by the following groups:

[0090] Any one of them;

[0091] Preferably, the M6 ​​ring is represented by the following groups:

[0092] Any one of them;

[0093] Each occurrence of Z being the same or different is represented as C-R0;

[0094] R, R0, R1, R2, and R3 are independently represented by the following structures: hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group, etc. Any one of them. Ar1 and Ar2 are independently represented as shown in the following structures:

[0095] Any one of them.

[0096] Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] The present invention also provides an organic electroluminescent device comprising a substrate, a first electrode, an organic functional material layer, and a second electrode. The first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the organic functional material layer. The organic functional material layer comprises a light-emitting layer, which comprises a host material and a dopant material. The dopant material is the boron-containing resonant organic compound of the present invention.

[0113] Furthermore, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is a boron-containing resonant organic compound as described in this invention.

[0114] Furthermore, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the boron-containing organic compound described in this invention.

[0115] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0116] (1) The compound of the present invention can be used in organic electroluminescent devices as a doping material for the light-emitting layer. It can emit green fluorescence under the action of an electric field and can be applied in the fields of OLED lighting or OLED display.

[0117] (2) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0118] (3) The compound of the present invention, as a green light doping material, can significantly improve device efficiency and device lifetime. Attached Figure Description

[0119] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0120] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation

[0121] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0122] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0123] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q1 and Q2 represent substituted or unsubstituted aromatic groups, and Q1 and Q2 preferably represent substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heteroaryl.

[0124] In this invention, the substituted or unsubstituted silane refers to Where Q3, Q4, and Q5 represent substituted or unsubstituted C1 to C2. 10 Alkyl or substituted or unsubstituted C3-C 10 Cycloalkyl groups, wherein the substituted or unsubstituted silyl group is preferably substituted or unsubstituted C3-C4. 10 Silyl group.

[0125] In this invention, the substituted or unsubstituted borane refers to Where Q6 and Q7 represent substituted or unsubstituted C1 to C2. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 heteroaryl groups.

[0126] In this invention, substituted or unsubstituted C6-C30 aryl refers to an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, preferably an aryl group with 6 to 20 substituted or unsubstituted carbon atoms, preferably an aryl group with 6 to 10 substituted or unsubstituted carbon atoms, preferably substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, substituted or unsubstituted The group may contain, but is not limited to, substituted or unsubstituted triphenyl, substituted or unsubstituted peryl, substituted or unsubstituted indole, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and combinations thereof or fused rings of the aforementioned groups.

[0127] In this invention, C6 to C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 18 carbon atoms, and even more preferably an aryl group having 6 to 12 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, diphenyl, terphenyl, anthracene, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, condensed tetraphenyl, and pyrene. Fused rings of methyl, triphenyl, peryl, indole, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0128] In this invention, the deuterium-substituted C6 to C6 are... 30 Aryl refers to a deuterated aryl group having 6 to 30 carbon atoms, preferably a deuterated aryl group having 6 to 18 carbon atoms, preferably a deuterated aryl group having 6 to 12 carbon atoms, preferably a deuterated phenyl, deuterated naphthyl, deuterated diphenyl, deuterated terphenyl, deuterated anthracene, deuterated phenanthyl, deuterated dimethylfluorenyl, deuterated diphenylfluorenyl, deuterated spirofluorenyl, deuterated tetraphenyl, deuterated pyrene, or deuterated... The group may contain, but is not limited to, deuterated triphenylene, deuterated perylene, deuterated indene, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, combinations thereof, or fused rings of the aforementioned groups.

[0129] In this invention, substituted or unsubstituted C2-C30 heteroaryl groups refer to heteroaryl groups with 5 to 30 substituted or unsubstituted cyclic atoms, preferably heteroaryl groups with 5 to 20 substituted or unsubstituted cyclic atoms, preferably heteroaryl groups with 5 to 10 substituted or unsubstituted cyclic atoms, preferably substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted The fused ring of benzothiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benzizinyl, substituted or unsubstituted benzizinyl, substituted or unsubstituted benzizinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted benzoindolyl, and combinations thereof or combinations of the foregoing groups, but not limited thereto.

[0130] In this invention, the 5-30 member heteroaryl refers to a heteroaryl with 2 to 30 carbon atoms, preferably a heteroaryl with 2 to 20 carbon atoms, preferably a heteroaryl with 4 to 20 carbon atoms, preferably a heteroaryl with 4 to 12 carbon atoms, preferably a heteroaryl with 5 to 12 carbon atoms, preferably furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrimidyl Fused rings of pyridyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, quinoxolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, benzopyrimidinyl, acridineyl, benzimineyl, benzimineyl, benzimineyl, fentanyl, dibenzofuranyl, dibenzothiaphenyl, carbazolyl, N-phenylcarbazolyl, benzoindolyl, and combinations thereof or combinations of the foregoing groups, but not limited thereto.

[0131] In this invention, the deuterated 5-30-membered heteroaryl group refers to a heteroaryl group with 2 to 30 deuterated carbon atoms, preferably a heteroaryl group with 2 to 20 deuterated carbon atoms, preferably a heteroaryl group with 4 to 12 deuterated carbon atoms, preferably a heteroaryl group with 5 to 12 deuterated carbon atoms, preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazinyl, or deuterated benzofuranyl. yl, deuterium-substituted benzothiophene, deuterium-substituted benzimidazolyl, deuterium-substituted indolyl, deuterium-substituted quinolinyl, deuterium-substituted isoquinolinyl, deuterium-substituted quinazolinyl, deuterium-substituted quinoxalinyl, deuterium-substituted naphthidyl, deuterium-substituted benzoxazinyl, deuterium-substituted benzothiazinyl, deuterium-substituted benzopyrimidinyl, deuterium Substituted acridine, deuterated benzinyl, deuterated benzithiazinyl, deuterated benzoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated carbazolyl, deuterated substituted N-phenylcarbazolyl, deuterated benzoindolyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0132] In this invention, the number of heteroatoms in the substituted or unsubstituted C2-C30 heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0133] The substituted or unsubstituted C1-C of this invention 10Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, preferably alkyl groups with 1 to 5 substituted or unsubstituted carbon atoms, preferably alkyl groups with 1 to 4 substituted or unsubstituted carbon atoms, preferably substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted neopentyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted isopentyl, substituted or unsubstituted octyl, substituted or unsubstituted heptyl, substituted or unsubstituted n-decyl, substituted or unsubstituted 1-methylpentyl, substituted or unsubstituted 2-methylpentyl, substituted or unsubstituted 3-methylpentyl, substituted or unsubstituted 1-butylpentyl, etc., but not limited to these.

[0134] In this invention, C1 to C 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, tert-pentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, 2-methylbutyl, etc., but not limited to these.

[0135] In this invention, the deuterium-substituted C1 to C1 are... 10 Alkyl groups (including straight-chain alkyl groups and branched alkyl groups) refer to deuterated alkyl groups having 1 to 10 carbon atoms, preferably deuterated alkyl groups having 1 to 6 carbon atoms, preferably deuterated alkyl groups having 1 to 5 carbon atoms, preferably deuterated alkyl groups having 1 to 4 carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, or deuterated tert-butyl. Butyl, deuterium-substituted isobutyl, deuterium-substituted sec-butyl, deuterium-substituted neopentyl, deuterium-substituted n-pentyl, deuterium-substituted isopentyl, deuterium-substituted tert-pentyl, deuterium-substituted octyl, deuterium-substituted heptyl, deuterium-substituted n-decyl, deuterium-substituted 1-methylpentyl, deuterium-substituted 2-methylpentyl, deuterium-substituted 3-methylpentyl, deuterium-substituted 1-butylpentyl, deuterium-substituted 2-methylbutyl, etc., but not limited to these.

[0136] The substituted or unsubstituted C3-C described in this invention 10Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, substituted or unsubstituted C4-C9 cycloalkyl groups are preferred, more preferably substituted or unsubstituted C5-C8 cycloalkyl groups, and particularly preferably substituted or unsubstituted C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted 4-methylcyclohexyl, substituted or unsubstituted 4,4-dimethylcyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted cycloheptyl, etc.

[0137] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0138] The C1-C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0139] The C2-C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.

[0140] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent PI film substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent glass substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0141] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, or it may be an alloy of several metals, or a combination of metals, metal oxides, or metal alloys. The thickness of the first electrode layer depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0142] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light-emitting layer, and an electron transport region.

[0143] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0144] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in organic electroluminescent devices.

[0145] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0146] Based on the above empirical summary, for hole-based host organic materials with different HOMO energy levels, it is necessary to select different P-doped materials to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0147] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from compounds disclosed in the prior art:

[0148]

[0149] Preferably, the p-type doped material is a charge-conducting compound disclosed in the prior art. The p-type dopant can be selected from compounds disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122. 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.

[0150] In one embodiment of the invention, the hole injection layer comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0151] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0152] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0153] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0154]

[0155] Preferably, the main organic material used as the hole transport layer material and the hole injection layer of the present invention is selected from the same compound.

[0156] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0157] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0158]

[0159] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0160] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0161] The light-emitting layer may include a host material and a dopant material. The host material may be a green light host material commonly used in the art, and the dopant material may be a boron-containing resonant organic compound represented by the general formula (1) of this invention.

[0162] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0163] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15, and more preferably 97:3-87:13, based on mass.

[0164] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0165] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0166] A hole-blocking layer is a layer that prevents holes injected from the anode from penetrating the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, for example:

[0167]

[0168] The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, more preferably 5-50nm, but the thickness is not limited to this range.

[0169] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these received electrons to the light-emitting layer. Preferably, a material with high electron mobility is used. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:

[0170]

[0171] In a preferred embodiment of the invention, the electron transport layer further includes other compounds conventionally used in electron transport layers, such as Alq3, Liq, preferably Liq.

[0172] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0173] An electron injection layer can be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of this invention, electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as LiF, Cs₂CO₃, CsF, Csq, NaF, MgF₂, CaF₂, Al₂O₃, Yb, etc.

[0174] The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0175] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0176] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0177] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0178] Synthesis Examples

[0179] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0180] Synthesis of intermediates C1 and D1:

[0181]

[0182] Add raw material B1 (25 mmol, 4.46 g), potassium carbonate (62.5 mmol, 8.64 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 1 hour. Add raw material A1 (25 mmol, 8.29 g) under nitrogen protection and stir at 150 °C for 16 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediates C1 and D1.

[0183] Synthesis of intermediates C2 and D2:

[0184]

[0185] The synthesis of intermediates C2 and D2 is similar to that of intermediates C1 and D1, except that raw material B2 is used instead of raw material B1.

[0186] Synthesis of intermediates C3 and D3:

[0187]

[0188] The synthesis of intermediates C3 and D3 is similar to that of intermediates C1 and D1, except that raw material B1 is replaced by raw material B3.

[0189] Synthesis of compound 3:

[0190]

[0191] Synthesis of intermediate G1: Add starting material E1 (20 mmol, 5.38 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add starting material F1 (20 mmol, 5.59 g) under nitrogen protection. Reflux the solution under magnetic stirring for 24 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate G1.

[0192] Synthesis of intermediate H1: Intermediate G1 (15 mmol, 7.93 g) and cesium carbonate (30 mmol, 9.77 g) were added to a two-necked flask. Under nitrogen protection, 80 mL of anhydrous DMF was added and the mixture was stirred at room temperature for 25 minutes. Under nitrogen protection, intermediate C2 (15 mmol, 9.30 g) was added. The solution was refluxed for 20 hours with magnetic stirring. After cooling, filtration, washing with water, drying, and column chromatography, intermediate H1 was obtained.

[0193] Synthesis of Compound 3: In a three-necked flask under nitrogen protection, intermediate H1 (10 mmol, 11.28 g) and 120 mL of o-dichlorobenzene were added. A 2.5 M solution of n-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, and the system was heated to 62 °C and reacted for 3.5 h. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 7 h. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, and the system was heated to 210 °C and reacted for 13 h. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 3. Compound 3 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0194] Synthesis of compound 34:

[0195]

[0196] The synthesis of intermediate G2 is similar to that of intermediate G1, except that raw material E1 is replaced by raw material E2.

[0197] The synthesis of intermediate H2 is similar to that of intermediate H1, except that intermediate G2 replaces intermediate G1 and intermediate C1 replaces intermediate C2.

[0198] The synthesis of compound 34 is similar to that of compound 3, except that intermediate H1 is replaced by intermediate H2. Compound 34 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0199] Synthesis of compound 167:

[0200]

[0201] The synthesis of intermediate H3 is similar to that of intermediate H1, except that intermediate C2 is replaced by intermediate D3.

[0202] The synthesis of compound 167 is similar to that of compound 3, except that intermediate H1 is replaced by intermediate H3. Compound 167 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0203] Synthesis of compound 254:

[0204]

[0205] Synthesis of intermediate G4: Add starting material E4 (20 mmol, 6.71 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 150 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 50 minutes. Add starting material F1 (20 mmol, 5.59 g) under nitrogen protection. Reflux the solution under magnetic stirring for 28 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate G4.

[0206] Synthesis of intermediate I4: Intermediate G4 (10 mmol, 5.95 g) was dissolved in 40 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 30 mL of tetrahydrofuran solution of starting material H4 (10 mmol, 1.80 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 30 mL of dilute hydrochloric acid (1.0 M) solution, distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate I4.

[0207] Synthesis of intermediate J4: Intermediate I4 (5 mmol, 3.16 g), intermediate C1 (5 mmol, 2.54 g), CuI catalyst (1 mmol, 0.19 g), and K3PO4 (25 mmol, 5.31 g) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (1.8 mmol, 0.2 g) and 85 mL of dioxane were added. The mixture was stirred at 120 °C for 18 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate J4.

[0208] The synthesis of compound 254 was carried out in a three-necked flask under nitrogen protection. Intermediate J4 (10 mmol, 10.58 g) and 80 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, and the system was heated to 60 °C and reacted for 3.5 h. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 8 h. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, and the mixture was heated to 200 °C and reacted for 12 h. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 254. Compound 254 was dissolved in toluene solution (1 × 10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0209] Synthesis of compound 256:

[0210]

[0211] The synthesis of intermediate J5 is similar to that of intermediate J4, except that intermediate C1 is replaced by intermediate C3.

[0212] The synthesis of compound 256 is similar to that of compound 254, except that intermediate J4 is replaced by intermediate J5. Compound 256 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 25 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0213] Synthesis of compound 287:

[0214]

[0215] The synthesis of intermediate I6 is similar to that of intermediate I4, except that raw material H4 is replaced by raw material H6.

[0216] The synthesis of intermediate J6 is similar to that of intermediate J4, except that intermediate I4 is replaced by intermediate I6.

[0217] The synthesis of compound 287 is similar to that of compound 254, except that intermediate J4 is replaced by intermediate J6. Compound 287 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0218] Synthesis of compound 322:

[0219]

[0220] The synthesis of intermediate J7 is similar to that of intermediate J4, except that intermediate C1 is replaced by intermediate D1.

[0221] The synthesis of compound 322 is similar to that of compound 254, except that intermediate J4 is replaced by intermediate J7. Compound 322 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width at half maximum (WHM) was 23 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0222] Synthesis of compound 353:

[0223]

[0224] The synthesis of intermediate J8 is similar to that of intermediate J4, except that intermediate C1 is replaced by intermediate D1 and intermediate I4 is replaced by intermediate I6.

[0225] The synthesis of compound 353 is similar to that of compound 254, except that intermediate J4 is replaced by intermediate J8. Compound 353 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0226] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0227] Table 1

[0228]

[0229]

[0230] The following describes in detail the application effects of the organic electroluminescent materials synthesized in this invention in devices through device examples 1-8 and device comparative examples 1-3. Device examples 2-8 and device comparative examples 1-3 of this invention have the same fabrication process as device example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 2 and 3, respectively.

[0231] Device Example 1

[0232] The transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 as the first dopant, and compound 3 as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 3 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30 nm. After the light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated by vacuum evaporation device, with a Mg:Ag mass ratio of 1:9. This layer is used as the cathode layer 10.

[0233] The molecular structural formulas of the relevant materials are shown below:

[0234]

[0235]

[0236] After the organic electroluminescent device was completed as described above, the anode and cathode were connected using a known driving circuit, and the current efficiency and lifetime of the device were measured. Examples and comparative examples of devices prepared using the same method are shown in Table 2; the test results for the CIEy, emission peak, current efficiency, and lifetime of the obtained devices are shown in Table 3.

[0237] Table 2

[0238]

[0239]

[0240] Table 3

[0241]

[0242] Note: Current efficiency and peak luminance were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device's brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0243] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1 and ref-2, the compound of the present invention can achieve the green light emission effect very well and has higher current efficiency; compared with the devices of comparative examples 1-2, the current efficiency and lifetime of the device are significantly improved compared with the devices of known materials.

[0244] As can be seen from the device data results in Table 3, compared with the comparative compound ref-3, the CIEy value and emission peak value of the comparative compound ref-3 cannot meet the display requirements of wide color gamut Adobe RGB (0.21, 0.75). The emission peak value of the boron-containing resonant organic compound of the present invention is between 515 and 525 nm, and the CIEy value is >0.75, which can better meet the display requirements of wide color gamut Adobe RGB (0.21, 0.75). The CIEy and emission peak value of the organic light-emitting device of the boron-containing resonant organic compound of the present invention are more in line with the requirements of wide color gamut display standards than the organic electroluminescent device of the known material ref-3.

[0245] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-containing resonance-type organic compound, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in general formula (A): In general formula (A), ring A is represented by the structure shown in general formula (A-1); X represents either a carbon atom or a silicon atom; M1, M2, M3, M4, M5, and M6 are each independently represented as one of the following: a C6-C30 aromatic ring substituted or unsubstituted with one or more Rs, or a C2-C30 heteroaromatic ring substituted or unsubstituted with one or more Rs. The R, whether appearing the same or different each time, is represented by one of the following: deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 alkenyl group, substituted or unsubstituted C2-C10 alkoxy group, substituted or unsubstituted C6-C10 aryloxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted boraneyl group, and substituted or unsubstituted C3-C10 silaneyl group. The replacement of R is either a single bond or a parallel ring connection; Ar1 and Ar2 are independently represented as one of the following: hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkoxy, substituted or unsubstituted C6-C10 aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted C3-C10 silyl. R1, R2, and R3 are each independently represented as one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 alkenyl group, substituted or unsubstituted C2-C10 alkoxy group, substituted or unsubstituted C6-C10 aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted boroalkyl group, and substituted or unsubstituted C3-C10 silyl group. R1, R2, and R3 are either not connected to each other or are connected by a single bond, double bond, -O-, -S-, or -N(R). a )-、-C(R b R c )-、-Si(R d R e - or -C(R) p )=C(R q - Connect into a loop; M1 and R3 are not connected or are connected via a single key, double key, -O-, -S-, or -N(R). a )-、-C(R b R c )-、-Si(R d R e - or -C(R) p )=C(R q - Connect into a loop; The R a R b R c R d R e R p R q Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Silyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C5-C 10 aryloxy group, substituted or unsubstituted C6-C 30 One of aryl, substituted or unsubstituted 5-30-membered heteroaryl, or substituted or unsubstituted borane; The R b and R c They are either not connected or connected in a loop by a single key; The R d and R e They are either not connected or connected in a loop by a single key; The substituents used for the substituent groups are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl. The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (1) to (4): In general formulas (1), (2), (3) and (4), the definitions of M1, M2, M3, M4, M5, M6, Ar1, Ar2, X, R1, R2 and R3 are the same as those in general formula (A); Y represents either a carbon atom or a silicon atom; M7 and M8 are respectively represented independently as one of the following: a C6-C30 aromatic ring substituted or unsubstituted with one or more Rs, or a C2-C30 heteroaromatic ring substituted or unsubstituted with one or more Rs; The R, whether appearing the same or different each time, is represented by one of the following: deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 alkenyl group, substituted or unsubstituted C2-C10 alkoxy group, substituted or unsubstituted C1-C10 aryloxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted boraneyl group, and substituted or unsubstituted C3-C10 silaneyl group. The replacement of R is either a single bond or a parallel ring connection; The substituents used for the substituent groups are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl. The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

3. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (5) to (8): In general formulas (5) to (8), the definitions of M1, M2, Ar1, Ar2, X, R1, R2, and R3 are the same as those in general formula (A); Y represents either a carbon atom or a silicon atom; M7 and M8 are respectively represented independently as one of the following: a C6-C30 aromatic ring substituted or unsubstituted with one or more Rs, or a C2-C30 heteroaromatic ring substituted or unsubstituted with one or more Rs; The R, whether appearing the same or different each time, is represented by one of the following: deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 alkenyl group, substituted or unsubstituted C2-C10 alkoxy group, substituted or unsubstituted C1-C10 aryloxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted boraneyl group, and substituted or unsubstituted C3-C10 silaneyl group. The replacement of R is either a single bond or a parallel ring connection; Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-(R0); The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents used for the substituent groups are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl. The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (9) to (18): In general formulas (9) to (18), the definitions of Ar1, Ar2, X, R1, R2, and R3 are the same as those in general formula (A); Y represents either a carbon atom or a silicon atom; Each occurrence of Z, whether the same or different, is represented as N, C-(H), or C-(R0); The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents used for the substituent groups are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl. The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

5. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (19) to (34): In general formulas (19)-34, the definitions of Ar1, Ar2, R1, and R2 are the same as those in general formula (A); Y represents either a carbon atom or a silicon atom; Each occurrence of Z that is independent is represented as N, C-(H), or C-(R0); The presence of R0, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C5-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, C2-C30 heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents used for the substituent groups are selected from any one or more of deuterium, halogen atoms, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C6-C30 aryl, deuterated C6-C30 aryl, C5-C30 heteroaryl, and deuterated C2-C30 heteroaryl. The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

6. The boron-containing organic compound according to any one of claims 1-5, characterized in that, The M1-M8 are each independently represented by one or more R-substituted or unsubstituted groups of the following: phenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, spirofluorenyl; R and R0 are independently represented as a deuterium atom, a halogen atom, a cyano group, a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), an anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), and a group substituted or unsubstituted. Unsubstituted pyridyl, quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spiroyl (substituted or unsubstituted) Fluorenyl, amino group substituted or unsubstituted, triazine group substituted or unsubstituted, propyl group substituted or unsubstituted, butyl group substituted or unsubstituted, isobutyl group substituted or unsubstituted, sec-butyl group substituted or unsubstituted, neopentyl group substituted or unsubstituted, n-pentyl group substituted or unsubstituted, isopentyl group substituted or unsubstituted, tert-pentyl group substituted or unsubstituted, 1-methylpentyl group substituted or unsubstituted, 2-methylpentyl group substituted or unsubstituted, 3-methylpentyl group substituted or unsubstituted, and so on. One of the following: unsubstituted 1-butylpentyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted tert-butyldimethylsilyl; The R1, R2, R3, R a R b R c R d R e R p R q Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), and [other groups are listed separately]. Pyridyl, quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorene (substituted or unsubstituted). The following groups are listed: amino group (substituted or unsubstituted), triazine group (substituted or unsubstituted), propyl group (substituted or unsubstituted), butyl group (substituted or unsubstituted), isobutyl group (substituted or unsubstituted), sec-butyl group (substituted or unsubstituted), neopentyl group (substituted or unsubstituted), n-pentyl group (substituted or unsubstituted), isopentyl group (substituted or unsubstituted), tert-pentyl group (substituted or unsubstituted), 1-methylpentyl group (substituted or unsubstituted), 2-methylpentyl group (substituted or unsubstituted), 3-methylpentyl group (substituted or unsubstituted), and so on. One of the following: unsubstituted 1-butylpentyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted tert-butyldimethylsilyl; Ar1 and Ar2 represent hydrogen atoms, deuterium atoms, halogen atoms, methyl groups (substituted or unsubstituted), ethyl groups (substituted or unsubstituted), isopropyl groups (substituted or unsubstituted), tert-butyl groups (substituted or unsubstituted), cyclohexyl groups (substituted or unsubstituted), adamantyl groups (substituted or unsubstituted), phenyl groups (substituted or unsubstituted), diphenyl groups (substituted or unsubstituted), terphenyl groups (substituted or unsubstituted), naphthyl groups (substituted or unsubstituted), anthracene groups (substituted or unsubstituted), phenanthryl groups (substituted or unsubstituted), and other substituents. Substituted pyridyl, quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorene (substituted or unsubstituted). The following groups are listed: amino group (substituted or unsubstituted), triazine group (substituted or unsubstituted), propyl group (substituted or unsubstituted), butyl group (substituted or unsubstituted), isobutyl group (substituted or unsubstituted), sec-butyl group (substituted or unsubstituted), neopentyl group (substituted or unsubstituted), n-pentyl group (substituted or unsubstituted), isopentyl group (substituted or unsubstituted), tert-pentyl group (substituted or unsubstituted), 1-methylpentyl group (substituted or unsubstituted), 2-methylpentyl group (substituted or unsubstituted), 3-methylpentyl group (substituted or unsubstituted), and so on. One of the following: unsubstituted 1-butylpentyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted indolyl, substituted or unsubstituted benzoindolyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted tert-butyldimethylsilyl; The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, and diphenylamino.

7. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

8. An organic electroluminescent device, comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the organic functional material layer, characterized in that: The organic functional material layer includes a light-emitting layer, which includes a host material and a dopant material, wherein the dopant material is a boron-containing resonant organic compound as described in any one of claims 1-7.

9. The organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a first host material, a second host material, and a dopant material, characterized in that: At least one of the first host material and the second host material is a TADF material, and the doping material is a boron-containing resonant organic compound as described in any one of claims 1-7.

10. The organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing organic compound as described in any one of claims 1-7.

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