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 semiconductors, and the structure of the compound provided by the invention is shown as a general formula (1). The material can be used as a luminescent layer green light doping material of an organic electroluminescent device, so that the service life of the device is prolonged.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of semiconductor technology, 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, such as: 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, sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it fully utilizes triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4). This technology can compensate for the insufficient exciton utilization of fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects for OLED applications. For example, CN 107507921A and CN 110492006A disclose a light-emitting layer combination technology using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005A and CN 110492009A disclose a light-emitting layer combination scheme using excitocomplexes as the main body and boron-containing materials as dopants; both can achieve efficiencies comparable to phosphorescence and relatively narrow half-peak widths (HWHM). Therefore, developing sensitization technologies based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for improving BT.2020 display performance. Summary of the Invention

[0005] To address the aforementioned problems in the prior art, this invention provides a boron-containing resonant organic compound and an organic electroluminescent device containing the same. The compound of this invention is used as a green light doping material in the light-emitting layer of an organic electroluminescent device, which can significantly improve the efficiency and lifespan of the device.

[0006] The technical solution of the present invention is as follows: a boron-containing resonance organic compound, the structure of which is shown in general formula (1):

[0007]

[0008] In general formula (1), each occurrence of M1 being the same or different is represented by C6 to C6 being substituted or unsubstituted by one or more R. 30 The aromatic ring, or a 5-30 membered heteroaromatic ring substituted or unsubstituted with one or more Rs;

[0009] Each occurrence of R, whether the same or different, represents 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 10alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 30 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted;

[0010] said R is connected by a single bond or annelated;

[0011] R1~R 14 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1-C20 alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, an aryl group, a 5- to 30-membered heteroaryl group, a boryl group, a silyl group, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 30 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted;

[0012] R1~R 14 are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)-, or -C(R'6)=C(R'7)-;

[0013] each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a C1-C20 alkyl group, a C3-C20 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, an aryl group, a 5- to 30-membered heteroaryl group, a boryl group, a silyl group, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 10 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted; 30 alkyl, aryl, heteroaryl, boryl, silyl, each of which is substituted or unsubstituted;

[0014] are not connected or are connected by a single bond, a double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)-, or -C(R'6)=C(R'7)-;

[0015] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as C1 to C2 groups, 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, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0016] R a Represented as cyano, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0017] R b Represented as hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0018] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0019] The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, B.

[0020] Further, R a represents a cyano group, an arylamine group substituted with a substituent or unsubstituted, a C6-C 10 cycloalkyl group substituted with a substituent or unsubstituted, a C2-C 10 alkenyl group substituted with a substituent or unsubstituted, a C2-C 16 alkynyl group substituted with a substituent or unsubstituted, an aryl group, a 5-30 membered heteroaryl group substituted with a substituent or unsubstituted, a borane group substituted with a substituent or unsubstituted, a silane group substituted with a substituent or unsubstituted.

[0021] Further, the boron-containing resonance-type organic compound has a structure represented by General Formula (A):

[0022]

[0023] In General Formula (A), R1to R 14 , R a , and R b are the same as defined above.

[0024] R 15 to R 21 each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group substituted with a substituent or unsubstituted, a C3-C 10 cycloalkyl group substituted with a substituent or unsubstituted, a C2-C 10 alkenyl group substituted with a substituent or unsubstituted, a C2-C 10 alkynyl group substituted with a substituent or unsubstituted, an arylamine group substituted with a substituent or unsubstituted, a C6-C 30 aryl group substituted with a substituent or unsubstituted, a 5-30 membered heteroaryl group substituted with a substituent or unsubstituted, a borane group substituted with a substituent or unsubstituted, a silane group substituted with a substituent or unsubstituted.

[0025] The substituent is optionally one or more of a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a deuterium-substituted C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a deuterium-substituted C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a deuterium-substituted C6-C 30 aryl group, a 5-30 membered heteroaryl group, a deuterium-substituted 5-30 membered heteroaryl group.

[0026] The heteroatom in the heteroaryl group is optionally one or more of O, S, N, Si, B.

[0027] Further, the boron-containing resonance-type organic compound has a structure represented by any one of General Formula (B-1) to General Formula (B-3):

[0028]

[0029]

[0030] In General Formula (B-1) to General Formula (B-3), R1to R 14 , Ar1, Ar2, R a , R b are the same as defined above;

[0031] R 15 to R 19 each independently represent one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a C1to C 10 alkyl group which is substituted or unsubstituted with a substituent, a C3to C 10 cycloalkyl group which is substituted or unsubstituted with a substituent, a C2to C 10 alkenyl group which is substituted or unsubstituted with a substituent, a C2to C 10 alkynyl group which is substituted or unsubstituted with a substituent, an arylamine group which is substituted or unsubstituted with a substituent, a C6to C 30 aryl group which is substituted or unsubstituted with a substituent, a 5- to 30-membered heteroaryl group which is substituted or unsubstituted with a substituent, a borane group which is substituted or unsubstituted with a substituent, and a silane group which is substituted or unsubstituted with a substituent;

[0032] The substituent is optionally selected from a deuterium atom, a halogen atom, a cyano group, a C1to C 10 alkyl group, a deuterium-substituted C1to C 10 alkyl group, a C3to C 10 cycloalkyl group, a deuterium-substituted C3to C 10 cycloalkyl group, a C6to C 30 aryl group, a deuterium-substituted C6to C 30 aryl group, a 5- to 30-membered heteroaryl group, and a deuterium-substituted 5- to 30-membered heteroaryl group;

[0033] The heteroatom in the heteroaryl group is optionally selected from one or more of O, S, N, Si, and B.

[0034] Further, the boron-containing resonance-type organic compound has a structure represented by any one of General Formula (C-1) to General Formula (C-3):

[0035]

[0036] In General Formula (C-1) to General Formula (C-3), R1to R 21 , R b are the same as defined above;

[0037] Each time Z appears, it is independently represented as C-(H) or C-(R0), where R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group that is 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0038] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0039] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0040] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (D-1) to (D-6):

[0041]

[0042] In general formulas (D-1) to (D-3), R1 to R 19 R b The definition is the same as the definition above;

[0043] Each time Z appears, it is independently represented as C-(H) or C-(R0), where R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group that is 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0044] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0045] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0046] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (E-1) to (E-3):

[0047]

[0048] In general formulas (E-1) to (E-3), R2, R5, R8, and R 13 R 16 R 19 The definitions of Z and Z are the same as those in the above text.

[0049] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (F-1) to (F-3):

[0050]

[0051] In general formulas (F-1) to (F-3), R2, R5, R8, and R 13 R 16 R 17 The definitions of Z and Z are the same as those in the above text.

[0052] Further, M1 represents any one of the following groups that are substituted or unsubstituted by R: phenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, quinolinyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl;

[0053] R, R0each independently represents a deuterium atom, a halogen atom, a cyano group, a methyl group substituted or non-substituted with a substituent, an ethyl group substituted or non-substituted with a substituent, an isopropyl group substituted or non-substituted with a substituent, a tert-butyl group substituted or non-substituted with a substituent, a cyclohexyl group substituted or non-substituted with a substituent, an adamantyl group substituted or non-substituted with a substituent, a phenyl group substituted or non-substituted with a substituent, a biphenyl group substituted or non-substituted with a substituent, a terphenyl group substituted or non-substituted with a substituent, a naphthyl group substituted or non-substituted with a substituent, an anthryl group substituted or non-substituted with a substituent, a phenanthryl group substituted or non-substituted with a substituent, a pyridyl group substituted or non-substituted with a substituent, a quinolyl group substituted or non-substituted with a substituent, a furanyl group substituted or non-substituted with a substituent, a thienyl group substituted or non-substituted with a substituent, a benzofuranyl group substituted or non-substituted with a substituent, a benzothienyl group substituted or non-substituted with a substituent, a dibenzofuranyl group substituted or non-substituted with a substituent, a dibenzothienyl group substituted or non-substituted with a substituent, a carbazolyl group substituted or non-substituted with a substituent, an N-phenylcarbazolyl group substituted or non-substituted with a substituent, a 9,9-dimethylfluorenyl group substituted or non-substituted with a substituent, a 9,9-diphenylfluorenyl group substituted or non-substituted with a substituent, a spirofluorenyl group substituted or non-substituted with a substituent, an amine group substituted or non-substituted with a substituent, a triazinyl group substituted or non-substituted with a substituent;

[0054] R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 R 21 R brespectively independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group;

[0055] the R a a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group;

[0056] R'1, R'2, R'3, R'4, R'5, R'6, R'7, respectively, independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group;

[0057] Ar1, Ar2, respectively, independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted triazinyl group;

[0058] The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0059] The R, R0, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 R 21 R b Ar1 and Ar2 are independently represented as hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-tert-butyl group, iso-tert-butyl group, trifluoromethyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated n-tert-butyl group, phenyl group, etc.

[0060] Any one of them;

[0061] The Ra is represented as cyano, cyclohexyl, adamantyl, phenyl, deuterium-substituted phenyl, fluorine-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, isopropyl-substituted phenyl, cyano-substituted phenyl, naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, cyano-substituted naphthyl, methyl-substituted naphthyl, deuterium-substituted naphthyl, fluorine-substituted naphthyl, tert-butylphenyl-substituted naphthyl, phenanthryl, pyrene, diphenyl, terphenyl, pyrimidinyl, phenyl-substituted pyridinyl, phenyl-substituted triazine, benzofuranyl, phenyl-substituted benzofuranyl, benzothiophene, phenyl-substituted benzothiophene, dibenzofuranyl, dibenzothiophene, benzodibenzofuranyl, benzodibenzothiophene.

[0062] Any one of them;

[0063] The substituent is represented by a deuterium atom, a fluorine atom, a cyano group, a cyclohexyl group, an adamantyl group, a phenyl group, a naphthyl group, a tert-butyl group, a methyl group, an isopropyl group, a phenanthryl group, a pyrenyl group, a biphenylyl group, a terphenylyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzo-dibenzofuranyl group, a benzo-dibenzothiophenyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, a deuterated phenyl group, a deuterated naphthyl group,

[0064] Any one of the above, wherein the mark indicates a bonding position.

[0065] Further, the specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] The present application also provides an organic light-emitting device, comprising a substrate, a first electrode, a functional layer and a second electrode in sequence, the functional layer is located between the first electrode and the second electrode, and the functional layer comprises the boron-containing resonance-type organic compound according to the present application.

[0076] Preferably, the functional layer comprises an emitting layer, the emitting layer comprises a host material and a dopant material, and the dopant material is the boron-containing resonance-type organic compound according to the present application.

[0077] Further, the functional layer comprises an emitting layer, the emitting layer comprises a host material, an exciton sensitization material and a dopant material, the exciton sensitization material is a complex containing a metal element, and the dopant material is the boron-containing resonance-type organic compound according to the present application.

[0078] Further, the host material comprises a first host material and a second host material.

[0079] Preferably, at least one of the first host material and the second host material is a TADF material

[0080] Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprising a first host material, a second host material and a dopant material, at least one of the first host material and the second host material being a TADF material, and the dopant material being the boron-containing resonance-type organic compound described above.

[0081] Further, the functional layer comprises a light-emitting layer, the light-emitting layer comprising a host material, an exciton sensitization material and a dopant material, the exciton sensitization material being a metal element-containing complex, and the dopant material being the boron-containing resonance-type organic compound described above.

[0082] Compared with the prior art, the present application has the beneficial technical effects that:

[0083] (1) The compound of the present application can be applied to an OLED device and can be used as a dopant material of a light-emitting layer, can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

[0084] (2) The spectral FWHM of the compound of the present application is narrow, which can effectively improve the color gamut of the device;

[0085] (3) The compound of the present application can be used as a green light dopant material, which can effectively improve the efficiency and service life of the device;

[0086] The compound of the present application has a narrow half-peak width characteristic and can be used as a green light dopant material of a light-emitting layer of an organic electroluminescent device, thereby improving the efficiency and service life of the device. BRIEF DESCRIPTION OF DRAWINGS

[0087] Figure 1 The structure schematic diagram of the material listed in the present application applied to an OLED device;

[0088] Among them, 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;

[0089] Figure 2 The nuclear magnetic resonance hydrogen spectrum of the compound 17 of the present application;

[0090] Figure 3 The PL spectrum of the compound 17 (1×10 -5 M toluene solution) of the present application;

[0091] Figure 4 The PL spectrum of the compound 145 (1×10 -5PL spectrum of M toluene solution;

[0092] Figure 5 The 1H NMR spectrum of compound 146 of this invention;

[0093] Figure 6 Compound 146 (1×10) of this invention -5 PL spectrum of M toluene solution. Detailed Implementation

[0094] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0095] 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.

[0096] In this invention, the substituted or unsubstituted aromatic amino group referred to in this invention means... Wherein W1 and W2 represent aromatic groups that are substituted or unsubstituted, and W1 and W2 preferably represent C6-C groups that are substituted or unsubstituted. 30 Aryl groups are 5-30 membered heteroaryl groups, either substituted or unsubstituted.

[0097] In this invention, C6-C is substituted or unsubstituted. 30 Aryl refers to an aryl group with 6 to 30 carbon atoms, substituted or unsubstituted, preferably an aryl group with 10 to 20 carbon atoms, preferably an aryl group with 10 to 16 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 a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a combination thereof, or a condensed ring of the foregoing, but is not limited thereto.

[0098] In the present application, the substituted or unsubstituted 5- to 30-membered heteroaryl means a heteroaryl having 5 to 30 ring-forming atoms, preferably a heteroaryl having 5 to 15 ring-forming atoms, preferably a heteroaryl having 5 to 10 ring-forming atoms, preferably a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthpyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazine group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a condensed ring of the foregoing, but is not limited thereto.

[0099] The substituted or unsubstituted C1-C 10Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to, but are not limited to, 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 (substituted or unsubstituted), etc.

[0100] The C3-C substituted or unsubstituted C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups, whether substituted or unsubstituted, are preferred; C5-C8 cycloalkyl groups, whether substituted or unsubstituted, are more preferred; and C5-C7 cycloalkyl groups, whether substituted or unsubstituted, are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, etc., whether substituted or unsubstituted.

[0101] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0102] The C1-C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0103] 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.

[0104] The substituents described in this invention are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0105] 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.

[0106] 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, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following compounds disclosed in the prior art: JP1996048656A, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0113] 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.

[0114] 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.

[0115] 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 meter.

[0116] 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.

[0117] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0118]

[0119] 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.

[0120] 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.

[0121] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0122]

[0123]

[0124] 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.

[0125] 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.

[0126] 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.

[0127] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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:

[0132]

[0133] 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.

[0134] 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:

[0135]

[0136]

[0137] 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.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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, BaF, 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, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0142] 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.

[0143] 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.

[0144] Preparation of compounds

[0145] 1. Synthesis of intermediate P

[0146] Synthesis of intermediate P1:

[0147]

[0148] Add raw material T1 (25 mmol, 4.5 g), potassium carbonate (62.5 mmol, 8.6 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 30 minutes. Add raw material R1 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P1.

[0149] Synthesis of intermediate P2:

[0150]

[0151] Add raw material T1 (25 mmol, 4.5 g), potassium carbonate (62.5 mmol, 8.6 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 30 minutes. Add raw material R2 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 10 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P2.

[0152] 2. Synthesis of intermediate Q

[0153] Synthesis of intermediate Q1:

[0154]

[0155] Add raw material M1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material M2 (20.2 mmol, 5.6 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 Y1.

[0156]

[0157] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.6 mL of n-butyllithium (1.2 M, 5.5 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M3 (5.5 mmol, 1.0 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), 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 Q1.

[0158] Synthesis of intermediate Q2:

[0159]

[0160] Intermediate Y1 (5.1 mmol, 3.0 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.6 mL of n-butyllithium (1.2 M, 5.5 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M4 (5.5 mmol, 1.6 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), 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 sodium bicarbonate (NaHCO3) solution. 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 Q2.

[0161] Synthesis of intermediate Q3:

[0162]

[0163] Add raw material M1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material M5 (20.2 mmol, 6.1 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 Y2.

[0164]

[0165] Intermediate Y2 (5.1 mmol, 3.2 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.6 mL of n-butyllithium (1.2 M, 5.5 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material M3 (5.5 mmol, 1.0 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 mL of dilute hydrochloric acid (1.0 M), 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 Q3.

[0166] 3. Synthesis of the Examples

[0167] Example 1: Synthesis of Compound 17:

[0168]

[0169] Intermediate Q1 (5 mmol, 3.2 g), starting material M2 (5 mmol, 1.4 g), CuI (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 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 80 mL of dioxane were added. The mixture was refluxed and stirred for 15 hours. The reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate J1.

[0170]

[0171] In a three-necked flask under nitrogen protection, intermediate J1 (10 mmol, 8.3 g) and 90 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 2 hours. 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 4 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was refluxed for 9 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K1.

[0172] Intermediate K1 (20.0 mmol, 16.1 g) was added sequentially to a three-necked flask, followed by 200 mL of 1,4-dioxane. The mixture was then cooled to 0°C under nitrogen protection and strictly protected from light. NBS (25 mmol, 4.45 g) was added in portions, and the mixture was stirred at 0°C for 12 hours. The reaction solution was concentrated and purified by silica gel column chromatography to obtain intermediate L1.

[0173]

[0174] Intermediate L1 (10 mmol, 8.8 g) and starting material A1 (11 mmol, 2.8 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 25 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 12 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 17. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 28 nm.

[0175] Example 2: Synthesis of compound 53:

[0176]

[0177] In a three-necked flask under nitrogen protection, intermediate L1 (5 mmol, 4.4 g), pinacol diboronate (10 mmol, 2.5 g), potassium acetate (15 mmol, 1.5 g), S-phos (1 mmol, 0.4 g), and Pd2(dba)3 (0.12 mmol, 0.1 g) were added to 150 mL of 1,4-dioxane. The mixture was refluxed for 8 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and purified by vacuum distillation and silica gel column chromatography to obtain intermediate L2.

[0178]

[0179] Starting material A2 (11 mmol, 3.4 g) and intermediate L2 (10 mmol, 9.3 g) were added to a three-necked flask and dissolved in a mixed solvent (80 mL toluene, 40 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 30 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 14 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 53. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 26 nm.

[0180] Example 3: Synthesis of Compound 66:

[0181]

[0182] Intermediate Q2 (5 mmol, 3.7 g), starting material A3 (5 mmol, 1.6 g), CuI (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 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 80 mL of dioxane were added. The mixture was refluxed and stirred for 15 hours. The reaction mixture was cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate J3.

[0183]

[0184] In a three-necked flask under nitrogen protection, intermediate J3 (10 mmol, 9.8 g) and 110 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 2 hours. 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 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was refluxed for 10 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K3.

[0185] Intermediate K3 (20.0 mmol, 19.1 g) was added sequentially to a three-necked flask, followed by 200 mL of 1,4-dioxane. The mixture was then cooled to 0°C under nitrogen protection and strictly protected from light. NBS (25 mmol, 4.45 g) was added in portions, and the mixture was stirred at 0°C for 12 hours. The reaction solution was concentrated and purified by silica gel column chromatography to obtain intermediate L3.

[0186]

[0187] Intermediate L3 (10 mmol, 10.3 g) and starting material A4 (11 mmol, 3.8 g) were added to a three-necked flask and dissolved in a mixed solvent (90 mL toluene, 45 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 35 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 12 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 66. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 23 nm.

[0188] Example 4: Synthesis of Compound 75:

[0189]

[0190] Intermediate Q1 (5 mmol, 3.2 g), intermediate P1 (5 mmol, 1.6 g), CuI (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 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 80 mL of dioxane were added. The mixture was refluxed and stirred for 12 hours. The reaction mixture was 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.

[0191]

[0192] In a three-necked flask under nitrogen protection, intermediate J4 (10 mmol, 8.7 g) and 90 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 2 hours. 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 5 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was refluxed for 11 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K4.

[0193] Intermediate K4 (20.0 mmol, 16.9 g) was added sequentially to a three-necked flask, followed by 200 mL of 1,4-dioxane. The mixture was then cooled to 0°C under nitrogen protection and strictly protected from light. NBS (25 mmol, 4.45 g) was added in portions, and the mixture was stirred at 0°C for 12 hours. The reaction solution was concentrated and purified by silica gel column chromatography to obtain intermediate L4.

[0194]

[0195] Intermediate L4 (10 mmol, 9.2 g) and starting material A5 (11 mmol, 2.2 g) were added to a three-necked flask and dissolved in a mixed solvent (90 mL toluene, 45 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 25 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 13 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 75. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0196] Example 5: Synthesis of Compound 110:

[0197]

[0198] Intermediate Q1 (5 mmol, 3.2 g), intermediate P2 (5 mmol, 1.6 g), CuI (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 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 80 mL of dioxane were added. The mixture was refluxed and stirred for 12 hours. The reaction mixture was 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 J5.

[0199]

[0200] In a three-necked flask under nitrogen protection, intermediate J5 (10 mmol, 8.7 g) and 90 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 hours. 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 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was refluxed for 12 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K5.

[0201] Intermediate K5 (20.0 mmol, 16.9 g) was added sequentially to a three-necked flask, followed by 200 mL of 1,4-dioxane. The mixture was then cooled to 0°C under nitrogen protection and strictly protected from light. NBS (25 mmol, 4.45 g) was added in portions, and the mixture was stirred at 0°C for 12 hours. The reaction solution was concentrated and purified by silica gel column chromatography to obtain intermediate L5.

[0202]

[0203] Intermediate L5 (10 mmol, 9.2 g) and starting material A5 (11 mmol, 2.2 g) were added to a three-necked flask and dissolved in a mixed solvent (90 mL toluene, 45 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 25 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 13 hours. A TLC sample was taken to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 110. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 28 nm.

[0204] Example 6: Synthesis of Compound 145:

[0205]

[0206] Intermediate L1 (10 mmol, 8.8 g) and starting material A6 (11 mmol, 2.9 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 25 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 12 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 145. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 26 nm.

[0207] Example 7: Synthesis of Compound 146:

[0208]

[0209] Intermediate Q3 (5 mmol, 3.3 g), starting material M5 (5 mmol, 1.5 g), CuI (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 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 80 mL of dioxane were added. The mixture was refluxed and stirred for 15 hours. The reaction mixture was 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 J7.

[0210]

[0211] In a three-necked flask under nitrogen protection, intermediate J7 (10 mmol, 8.8 g) and 90 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 4 hours. 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 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added to the system at 0 °C, and the mixture was refluxed for 15 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate K7.

[0212]

[0213] Intermediate K7 (20.0 mmol, 17.0 g) was added sequentially to a three-necked flask, followed by 200 mL of 1,4-dioxane. The mixture was then cooled to 0°C under nitrogen protection and strictly protected from light. NBS (25 mmol, 4.45 g) was added in portions, and the mixture was stirred at 0°C for 12 hours. The reaction solution was concentrated and purified by silica gel column chromatography to obtain intermediate L7.

[0214]

[0215] Intermediate L7 (10 mmol, 9.3 g) and starting material A6 (11 mmol, 2.9 g) were added to a three-necked flask and dissolved in a mixed solvent (90 mL toluene, 45 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 30 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 12 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 146. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0216] Example 8: Synthesis of Compound 1:

[0217]

[0218] Intermediate L1 (10 mmol, 8.8 g) and starting material A1 (11 mmol, 2.2 g) were added to a three-necked flask and dissolved in a mixed solvent (70 mL toluene, 35 mL ethanol). Then, Pd(PPh3)4 (0.10 mmol, 0.12 g) and 25 mL of 3 mol / L K2CO3 aqueous solution were added. The mixture was heated to reflux under nitrogen protection for 12 hours. A sample was spotted onto a TLC plate to confirm complete reaction. After cooling to room temperature, the reaction mixture was filtered through a diatomaceous earth filter, washed with chloroform, and the resulting filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel to give compound 1. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 29 nm.

[0219] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0220] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0221] Table 1

[0222]

[0223]

[0224] The following describes in detail the application effects of the OLED materials synthesized in this invention in devices through device examples 1-8 and device comparative examples 1-2. Device examples 2-8 and device comparative examples 1-2 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 doping material in the light-emitting layer. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0225] Device Example 1

[0226] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (SemicleanM-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, HT-1 and HI-1 with a thickness of 10nm are 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. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 17 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 17 of 69:30:1, and a film thickness of 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as 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 serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0227] The application effects of the OLED materials synthesized in this invention in devices are described in detail below through device examples 9-16 and device comparative examples 3-4. Device examples 10-16 and device comparative examples 3-4 of this invention have the same fabrication process as device example 9, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the doping material in the light-emitting layer. The layer structure and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0228] Device Example 9

[0229] The transparent substrate layer 1 is a transparent PI film. 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 emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 17 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 17 is 66.5:30:3:0.5, and the thickness of the emitting layer is 30 nm. After the 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.

[0230] The molecular structural formulas of the relevant materials are shown below:

[0231]

[0232] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0233] Table 2-1

[0234]

[0235]

[0236] Table 2-2

[0237]

[0238]

[0239] Table 3

[0240]

[0241] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) 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 brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0242] As can be seen from the device data results in Table 3, the emission peak of the compound of the present invention is between 510 and 540 nm, which can achieve the effect of green light emission very well. Compared with the devices in Comparative Examples 1-4, the organic light-emitting device of the present invention has a significantly improved current efficiency and lifetime compared with OLED devices made of known materials, whether in a single-doped system or a double-doped system. When using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with the single-doped system.

[0243] 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 organic compound is shown in general formula (1): In general formula (1), each occurrence of M1 being the same or different indicates that C6 to C6 are substituted or unsubstituted by one or more R. 30 The aromatic ring, or a 5-30 membered heteroaromatic ring substituted or unsubstituted with one or more Rs; Each occurrence of R, whether the same or different, represents 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The replacement of R is either a single bond or a parallel ring connection; R1~R 14 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); R1~R 14 The two adjacent groups are not connected or are connected by a single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-; Ar1 and Ar2 are independently represented as hydrogen atoms, deuterium atoms, halogen atoms, and C1-C atoms with or without substituents, respectively. 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); Ar1 and Ar2 are not connected or are connected by a single bond, double bond, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-; R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as C1 to C2 groups, 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, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); R a Represented as cyano, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 One of aryl, substituted or unsubstituted 5-30 membered heteroaryl; R b Represented as hydrogen atom, deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 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-type organic compound is shown in general formula (A): In general formula (A), R1~R 14 R a R b The definition is the same as that in claim 1; R 15 ~R 21 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 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 (B-1) to (B-3): In general formulas (B-1) to (B-3), R1 to R 14 Ar1, Ar2, R a R b The definition is the same as that in claim 1; R 15 ~R 19 Each of the following can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C1 atoms 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 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 2, characterized in that, The structure of the boron-containing resonance organic compound is shown in any one of general formulas (C-1) to (C-3): In general formulas (C-1) to (C-3), R1 to R 21 R b The definition is the same as that in claim 2; Each time Z appears, it is independently represented as C-(H) or C-(R0), where R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group that is 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 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 3, characterized in that, The structure of the boron-containing resonance organic compound is shown in any one of general formulas (D-1) to (D-6): In general formulas (D-1) to (D-3), R1 to R 19 R b The definition is the same as that in claim 3; Each time Z appears, it is independently represented as C-(H) or C-(R0), where R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group that is 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

6. The boron-containing resonance-type organic compound according to claim 4, characterized in that, The structure of the boron-containing resonance organic compound is shown in any one of general formulas (E-1) to (E-3): In general formulas (E-1) to (E-3), R2, R5, R8, and R 13 R 16 R 19 The definitions of Z and Z are the same as those in claim 4.

7. The boron-containing resonance-type organic compound according to claim 5, characterized in that, The structure of the boron-containing resonance organic compound is shown in any one of general formulas (F-1) to (F-3): In general formulas (F-1) to (F-3), R2, R5, R8, and R 13 R 16 R 17 The definitions of Z and Z are the same as those in claim 5.

8. The boron-containing resonance-type organic compound according to any one of claims 1-7, characterized in that, M1 represents any one of the following groups, substituted or unsubstituted with R: 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, and 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), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), and a group with a substituted or unsubstituted group. Substituted quinolinyl, 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), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted). The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 R 17 R 18 R 19 R 20 R 21 R b 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), pyridyl group (substituted or unsubstituted), and [other groups, substituted or unsubstituted]. Quinolinyl, 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), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted). The R a Represented as cyano, cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraquinyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), and so on. 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), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted); R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are respectively independently represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), and so on. Quinolinyl group (substituted or unsubstituted), furanyl group (substituted or unsubstituted), thiophene group (substituted or unsubstituted), benzofuranyl group (substituted or unsubstituted), benzothiophene group (substituted or unsubstituted), dibenzofuranyl group (substituted or unsubstituted), dibenzothiophene group (substituted or unsubstituted), carbazoyl group (substituted or unsubstituted), N-phenylcarbazoyl group (substituted or unsubstituted), 9,9-dimethylfluorenyl group (substituted or unsubstituted), 9,9-diphenylfluorenyl group (substituted or unsubstituted), spirofluorenyl group (substituted or unsubstituted), amino group (substituted or unsubstituted), triazine group (substituted or unsubstituted). Ar1 and Ar2 are independently represented as hydrogen atom, deuterium atom, halogen atom, 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), pyridyl group (substituted or unsubstituted), and substituted... Or unsubstituted quinolinyl, furanyl substituted or unsubstituted, thiophene substituted or unsubstituted, benzofuranyl substituted or unsubstituted, benzothiophene substituted or unsubstituted, dibenzofuranyl substituted or unsubstituted, dibenzothiophene substituted or unsubstituted, carbazoyl substituted or unsubstituted, N-phenylcarbazoyl substituted or unsubstituted, 9,9-dimethylfluorenyl substituted or unsubstituted, 9,9-diphenylfluorenyl substituted or unsubstituted, spirofluorenyl substituted or unsubstituted, amino substituted or unsubstituted, triazine substituted or unsubstituted; The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

9. 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:

10. An organic light-emitting device, comprising a substrate, a first electrode, a functional layer, and a second electrode in sequence, wherein the functional layer is located between the first electrode and the second electrode, characterized in that, The functional layer comprises a boron-containing resonance-type organic compound as described in any one of claims 1-9; Preferably, the functional layer includes a light-emitting layer, which comprises 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 1-9.

11. The organic light-emitting device according to claim 10, characterized in that, The functional layer includes a light-emitting layer, which 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 a boron-containing resonant organic compound as described in any one of claims 1-9.

12. The organic light-emitting device according to claim 10 or 11, characterized in that, The main material includes a first main material and a second main material; Preferably, at least one of the first main material and the second main material is TADF material.

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