Organic light-emitting device

Abstract

The invention discloses an organic light-emitting device which sequentially comprises a substrate, a first electrode, an organic functional layer and a second electrode, the organic functional layer comprises a hole transmission region, a light-emitting region and an electron transmission region, the light-emitting region comprises a compound shown in a formula (1), and the hole transmission region comprises a compound shown in a formula (2); the matching of the # imgabs0 # in the organic device can simultaneously display the effects of improving the efficiency of the device and prolonging the service life of the device, and particularly, the service life of the device is remarkably prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs) can be used to manufacture new display products as well as new lighting products. They are expected to replace existing liquid crystal displays and fluorescent lighting, and have a wide range of applications. Organic light-emitting diodes are like sandwich structures, including electrode material films and organic functional materials sandwiched between different electrode material films. Various organic functional materials are superimposed on each other according to their uses to form organic light-emitting diodes. As a current device, when voltage is applied to the electrodes at both ends of the organic light-emitting diode, the positive and negative charges in the organic layer functional material film layer are further compounded in the light-emitting layer through the electric field, generating organic electroluminescence.

[0003] Currently, organic electroluminescent display technology has been applied in smart phones, tablet computers, televisions and other fields. However, compared with the actual product application requirements, the luminous efficiency and service life of organic electroluminescent devices need to be further improved. Research on improving the performance of organic electroluminescent devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device. In order to continuously improve the performance of organic electroluminescent devices, it is necessary not only to innovate the structure and manufacturing process of organic electroluminescent devices, but also to continuously study and innovate organic functional materials to create higher performance organic functional materials.

[0004] Blue organic electroluminescent devices have always been the weak point in the development of full-color OLEDs. Up to now, the performance of blue light devices such as efficiency and life span has been difficult to be comprehensively improved. Therefore, how to improve the performance of blue light devices remains a crucial issue and challenge facing this field. Summary of the invention

[0005] In view of the above problems existing in the prior art, the present invention provides an organic electroluminescent device. The organic electroluminescent device of the present invention can effectively improve the life and efficiency of the organic electroluminescent device by selecting a boron nitrogen compound with a specific structure in the light-emitting region and a carbazole compound with a specific structure in the hole transport region.

[0006] The technical solution of the present invention to solve the above technical problems is as follows: an organic electroluminescent device comprises a substrate, a first electrode, an organic functional layer and a second electrode in sequence, the organic functional layer comprises a hole transport region, a light emitting region and an electron transport region; the light emitting region comprises a compound represented by formula (1); the hole transport region comprises a compound represented by formula (2);

[0007]

[0008] In formula (1), C and D are independently represented by R-substituted or unsubstituted C6-C 30 Aromatic ring, R substituted or unsubstituted 5-30 membered heteroaromatic ring, R substituted or unsubstituted C6-C 30 aliphatic ring;

[0009] Ar1 and Ar2 are independently represented by R substituted or unsubstituted C6-C 30 Aryl, R substituted or unsubstituted 5-30 membered heteroaryl, R substituted or unsubstituted C6-C 30 aliphatic cyclic group;

[0010] The R may be the same or different each time and may represent a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0011] The R a , R b , R c Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0012] The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups;

[0013] The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si, and B;

[0014] In formula (2), R1 and R2 are independently substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0015] The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0016] The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;

[0017] The p and q are independently represented by the numbers 0, 1, 2, 3 or 4, and p+q≧1;

[0018] The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring;

[0019] The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0020] The heteroatom may be selected from one or more of oxygen, sulfur or nitrogen atoms.

[0021] In a preferred embodiment, at least one hydrogen atom in the compound represented by formula (2) is replaced by a deuterium atom.

[0022] In a preferred embodiment, the light-emitting region comprises a main material and a doping material, and the doping material comprises a compound represented by formula (1).

[0023] In a preferred embodiment, the hole transport region comprises a hole injection layer, a hole transport layer and a light-emitting layer auxiliary layer in sequence, and the light-emitting auxiliary layer comprises a compound represented by formula (2); preferably, the hole injection layer comprises an aromatic amine compound and an alkylene compound.

[0024] In a preferred embodiment, the formula (1) is represented by any one of the following formulas (1-1) to (1-5):

[0025]

[0026] In formula (1-1) to formula (1-5), Ar1 and Ar2 are independently represented by R-substituted or unsubstituted C6-C 30 Aryl, R substituted or unsubstituted 5-30 membered heteroaryl, R substituted or unsubstituted C6-C 30 aliphatic ring;

[0027] The R may be the same or different each time and may represent a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0028] The R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R mEach occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0029] The X represents one of C(Q1)(Q2), Si(Q3)(Q4), N-Q5, O, and S, wherein Q1, Q2, Q3, Q4, and Q5 represent substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0030] The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups;

[0031] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0032] In a preferred embodiment, the formula (1) is expressed as any one of the following formulas (1-6) to (1-7):

[0033]

[0034] In formula (1-6) to formula (1-7), the R a , R b , R c , R d , R e , R f , R h , Ri , R j , R k , R m , R n , R o , R p , R q , R s , R f , R w , R x , R y , R z Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group;

[0035] The X represents one of C(Q1)(Q2), Si(Q3)(Q4), N-Q5, O, and S, wherein Q1, Q2, Q3, Q4, and Q5 represent substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0036] The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups;

[0037] The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

[0038] In a preferred embodiment, C and D represent the following groups which are substituted or unsubstituted by R: any one of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl and spirofluorenyl;

[0039] The R represents a deuterium atom, a tritium 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, linoyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0040] The R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R m , R n , R o , R p , R q , R s , R f , R w , R x , R y , R zEach of the above is independently a hydrogen atom, a deuterium atom, a tritium 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0041] Ar1 and Ar2 are independently substituted or unsubstituted 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0042] The Q1, Q2, Q3, Q4, and Q5 are independently substituted or unsubstituted 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl;

[0043] The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group.

[0044] Preferably, the R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R m , R n , R o , R p , R q , R s , R f , R w , R x , R y , R z They are independently represented as follows:

[0045] Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl,

[0046] Any of;

[0047] The Ar1 and Ar2 are represented by the following structures:

[0048]

[0049] Any one of.

[0050] The present invention also provides a deuterium-containing aromatic amine compound, the structure of the deuterium-containing aromatic amine compound is shown in formula (2);

[0051]

[0052] In formula (2), R1 and R2 are independently substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0053] The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0054] The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;

[0055] The p and q are independently represented by the numbers 0, 1, 2, 3 or 4, and p+q≧1;

[0056] The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring;

[0057] The substituents of the above substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0058] The heteroatom is selected from one or more of oxygen atoms, sulfur atoms or nitrogen atoms.

[0059] At least one hydrogen atom in the compound represented by formula (2) is replaced by a deuterium atom.

[0060] Preferably, the formula (2) is represented by any one of formula (2-1) to formula (2-2):

[0061]

[0062] In formula (2-1)-formula (2-2), R1 and R2 are independently represented by substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0063] The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0064] The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;

[0065] The p and q are independently represented by the numbers 0, 1, 2, 3 or 4, and p+q≧1;

[0066] The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring;

[0067] The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0068] The heteroatom may be selected from one or more of oxygen, sulfur or nitrogen atoms.

[0069] Preferably, the formula (2) is represented by any one of formula (2-3) to formula (2-8):

[0070]

[0071]

[0072] In formula (2-1)-formula (2-2), R1 and R2 are independently represented by substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0073] The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl;

[0074] The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene;

[0075] The p and q are independently represented by the numbers 0, 1, 2, 3 or 4;

[0076] The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring;

[0077] The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0078] The heteroatom may be selected from one or more of oxygen, sulfur or nitrogen atoms.

[0079] Preferably, the formula (2) is represented by any one of formula (2-9) to formula (2-16):

[0080]

[0081]

[0082] Preferably, the formula (2) is represented by any one of formula (2-17) to formula (2-24):

[0083]

[0084]

[0085] Preferably, the formula (2) is represented by any one of formula (2-25) to formula (2-28):

[0086]

[0087] Said R1 and R2 are independently represented by substituted or substituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl;

[0088] The L1 and L2 are independently represented by a direct bond, a phenylene group, a naphthylene group or a biphenylene group;

[0089] The substituents are selected from one or more of deuterium atoms, cyano groups, halogen groups, phenyl groups, naphthyl groups, biphenyl groups, methyl groups, tert-butyl groups, and adamantyl groups.

[0090] In a preferred embodiment, R1 and R2 are respectively represented by any of the following structures: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted indolyl;

[0091] The L1 and L2 are respectively one of a single bond, a substituted or substituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group;

[0092] The R5-R 12 Respectively represent any of the following structures: one of a hydrogen atom, a methyl group, a deuterated methyl group, an ethyl group, a tert-butyl group, a phenyl group, an adamantyl group, a naphthyl group, and a biphenyl group;

[0093] The substituent replacing the above substitutable group is selected from one or more of a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a carbazolyl group, a phenanthryl group, a dibenzothienyl group, and a benzofuranyl group;

[0094] In a preferred embodiment, R1, R2, R3, and R4 are respectively represented by any of the following structures:

[0095]

[0096] The L1 and L2 are respectively represented by a direct bond or any of the structures shown below:

[0097]

[0098] Preferably, the formula (2) is selected from any one of the following specific structures:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] The formula (1) is selected from any one of the following specific structures:

[0126]

[0127] Compared with the prior art, the beneficial technical effects of the present invention are:

[0128] The organic electroluminescent device of the present invention can effectively block excitons by selecting a boron nitrogen compound with a specific structure in the light-emitting region and a carbazole compound with a specific structure in the hole transport region, and can efficiently transport holes to the light-emitting layer to ensure the carrier balance of the light-emitting layer, thereby effectively improving the life and efficiency of the organic electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0129] Figure 1 is a schematic structural diagram of the organic electroluminescent device described in the embodiment;

[0130] In the figure, 1 is a glass substrate layer; 2 is an anode layer; 3 is a hole injection layer; 4 is a hole transport layer; 5 is a light-emitting auxiliary 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; 10 is a cathode layer; 11 is a CPL layer. DETAILED DESCRIPTION

[0131] The technical solutions in the embodiments of the present invention will be described clearly and completely below in conjunction with the accompanying drawings in the embodiments of the present invention.

[0132] In the present invention, when a layer or element is referred to as being "on" another layer or substrate, the layer or element may be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intervening layers may also be present.

[0133] In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, the words "upper", "lower", "top" and "bottom" used to indicate orientation only indicate the orientation in a certain state, and do not mean that the related structure can only exist in the orientation described; on the contrary, if the structure can change its position, such as inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" or "upper" side.

[0134] In this specification, the term "substituted" means that one or more hydrogen atoms on a designated atom or group are replaced by a designated group, provided that the normal valency of the designated atom is not exceeded under the existing circumstances.

[0135] In this specification, the hole characteristic refers to a characteristic that can donate electrons when an electric field is applied and holes formed in the anode are easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristic according to the highest occupied molecular orbital (HOMO) level.

[0136] In this specification, the electronic characteristics refer to the characteristics that electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristics according to the lowest unoccupied molecular orbital (LUMO) level when an electric field is applied.

[0137] The organic electroluminescent device of the present invention may be a bottom-emitting organic electroluminescent device, a top-emitting organic electroluminescent device, or a stacked organic electroluminescent device, without any particular limitation.

[0138] The organic electroluminescent device of the present invention comprises a substrate, a first electrode, an organic functional layer and a second electrode. The organic functional layer comprises a hole transport region, a light emitting region and an electron transport region, the hole transport region comprises a hole injection layer, a hole transport layer and a light emitting auxiliary layer, the electron transport region comprises a hole blocking layer, an electron transport layer and an electron injection layer, and a CPL layer may be arranged on the second electrode.

[0139] The first electrode may be an anode or a cathode, and the second electrode may be a cathode or an anode.

[0140] In the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples thereof are transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; flexible polyimide (PI) film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, its use direction is different. In the present invention, a transparent glass substrate is preferably used. The thickness of the substrate is not particularly limited.

[0141] anode:

[0142] In the present invention, an anode may be formed on a substrate. The anode and the cathode are opposite to each other. The anode may be made of a conductor having a higher work function to facilitate hole injection, and may be, for example, a metal such as nickel, platinum, copper, zinc, silver, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and a metal oxide such as ZnO and Al or ITO and Ag; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) and polyaniline, but not limited thereto. The thickness of the anode depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm. In the present invention, metal Ag is preferably used.

[0143] cathode:

[0144] The cathode can be made of a conductor with a lower work function to facilitate electron injection, such as a metal or its alloy, such as magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; a multilayer structure material, such as LiF / Al, Li2O / Al, and BaF2 / Ca, but not limited thereto. The thickness of the cathode depends on the material used, and is generally 10-50 nm, preferably 15-20 nm.

[0145] Emitting area:

[0146] In the present invention, the light-emitting region can be arranged between the anode and the cathode, and can include at least one host material and at least one guest material. As the host material and the guest material of the light-emitting region of the organic electroluminescent device of the present invention, the light-emitting layer materials for organic electroluminescent devices known in the prior art can be used.

[0147] In a preferred embodiment of the present invention, the light emitting region comprises one or two host material compounds.

[0148] In a preferred embodiment of the present invention, the host material of the light-emitting region used is selected from one or more of the following compounds BH1-BH6:

[0149]

[0150] In the present invention, the light-emitting region may contain a phosphorescent or fluorescent guest material to improve the fluorescent or phosphorescent properties of the organic electroluminescent device. Specific examples of phosphorescent guest materials include metal complexes of iridium, platinum, etc. For fluorescent guest materials, those commonly used in the art can be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds BD1 to BD3:

[0151]

[0152] In the light emitting region of the present invention, the ratio of the host material to the guest material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0153] The thickness of the light emitting region may be 10-50 nm, preferably 15-30 nm, but the thickness is not limited to this range.

[0154] Hole transport region:

[0155] In the organic electroluminescent device of the present invention, the hole transport region is arranged between the anode and the light emitting region, and includes a hole injection layer, a hole transport layer and a light emitting layer auxiliary layer.

[0156] Hole injection layer:

[0157] The hole injection material used in the hole injection layer (also called the anode interface buffer layer) is a material that can fully accept holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of a main organic material and a P-type doping material. In order to smoothly inject holes from the anode into the organic film layer, the HOMO energy level of the main organic material must have certain characteristics with the P-type doping material, so that it is expected to realize the occurrence of charge transfer states between the main material and the doping material, and realize the ohmic contact between the hole injection layer and the anode, thereby realizing efficient injection of holes from the electrode to the hole injection layer. This feature is summarized as: the difference between the HOMO energy level of the main material and the LUMO energy level of the P-type doping material is ≤0.4eV. Therefore, for hole-type main materials with different HOMO energy levels, different P-type doping materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0158] Preferably, the host organic material is an aromatic amine-based organic material, but is not limited thereto.

[0159] Preferably, the P-type doping material is selected from the compounds with charge conductivity disclosed in the prior art, and the P-type dopant can be selected from the compounds disclosed in the following patent documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE102007031220A 1. US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but are not limited thereto.

[0160] In a preferred embodiment of the present invention, the P-type doping material used is selected from any one of the following compounds HI1 to HI8:

[0161]

[0162] In one embodiment of the present invention, the ratio of the host organic material to the P-type doping material used is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0163] In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of an aromatic amine compound and a P-type doping material.

[0164] The thickness of the hole injection layer of the present invention may be 5-20 nm, preferably 8-15 nm, but the thickness is not limited to this range.

[0165] Hole transport layer:

[0166] In the organic electroluminescent device of the present invention, a hole transport layer may be disposed above the hole injection layer. The hole transport material is a suitable material with high hole mobility, which can accept holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include: aromatic amine organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto. In a preferred embodiment, the hole transport layer comprises the same aromatic amine organic compound as the hole injection layer.

[0167] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art:

[0168]

[0169] The thickness of the hole transport layer of the present invention may be 80, 100 or 200 nm, preferably 100-150 nm, but the thickness is not limited to this range.

[0170] Luminous layer auxiliary layer:

[0171] In the organic electroluminescent device of the present invention, the light-emitting layer auxiliary layer may be arranged between the hole transport layer and the light-emitting layer, and in particular contact the light-emitting layer. The light-emitting layer auxiliary layer is arranged to contact the light-emitting layer, and therefore, the hole transfer at the interface between the light-emitting layer and the hole transport layer can be accurately controlled. In one embodiment of the present invention, the light-emitting layer auxiliary layer material is selected from the aromatic amine compounds described in the general formula (1). The thickness of the light-emitting layer auxiliary layer may be 5-20 nm, preferably 8-15 nm, but the thickness is not limited to this range.

[0172] Electron transport region:

[0173] In the organic electroluminescent device of the present invention, the electron transport region is disposed between the light emitting region and the cathode, and includes a hole blocking layer, an electron transport layer and an electron injection layer, but is not limited thereto.

[0174] Electron injection layer:

[0175] The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer material for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide.

[0176] The thickness of the electron injection layer of the present invention may 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.

[0177] Electron transport layer:

[0178] The electron transport layer may be disposed on the light-emitting film layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. A material having a high electron mobility is preferred. As the electron transport layer of the organic electroluminescent device of the present invention, the electron transport layer material for organic electroluminescent devices known in the prior art can be used.

[0179] As the electron transport layer of the organic electroluminescent device of the present invention, the following compounds disclosed in the prior art can be used as electron transport layer materials of the organic electroluminescent device:

[0180]

[0181]

[0182] The electron transport layer further includes other compounds conventionally used in electron transport layers, for example, Alq3, LiQ, preferably LiQ.

[0183] The thickness of the electron transport layer of the present invention may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0184] Hole blocking layer

[0185] The hole blocking layer may be disposed between the light-emitting layer and the electron transport layer. The hole blocking layer is used to block the holes injected from the anode from passing through the light-emitting layer and entering the electron transport layer. As the hole blocking layer of the organic electroluminescent device of the present invention, the hole blocking layer materials for organic electroluminescent devices disclosed in the following prior art may be used:

[0186]

[0187] Cover:

[0188] In order to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (ie, CPL layer, also called covering layer) may be added on the cathode of the device. The compounds disclosed in the prior art may be used as the CPL layer material.

[0189]

[0190]

[0191] The thickness of the CPL cover layer is typically 5-300 nm, preferably 20-100 nm and more preferably 40-80 nm.

[0192] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign 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 can or a metal can; or a thin film covering the entire surface of the organic layer.

[0193] The method for preparing an organic electroluminescent device of the present invention comprises laminating an anode, a hole injection layer, a hole transport layer, a light-emitting layer auxiliary layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0194] In addition, it should be noted that the materials used to form each layer described in the present invention can be formed into a film alone and used as a single layer, or can be mixed with other materials to form a film and used as a single layer. It can also be a stacked structure between layers formed into films alone, a stacked structure between layers formed into films after mixing, or a stacked structure of layers formed into films alone and layers formed into films after mixing.

[0195] Preparation Example

[0196] Example 1: Synthesis of Intermediate M-1

[0197]

[0198]

[0199] (1) In a three-necked flask, under nitrogen protection, add 0.01 mol (1.67 g) of raw material A-1, 0.012 mol (3.81 g) of raw material B-1, and 150 ml of toluene, stir and mix, then add 5×10 -5 mol(0.046g)Pd2(dba)3,5×10 -5 mol (0.010g) tri-tert-butyl phosphine, 0.03mol (2.88g) sodium tert-butoxide, heated to 105°C, refluxed for 18 hours, sampling point plate, showing no raw material A-1 remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated until there was no fraction, passed through a neutral silica gel column to obtain intermediate K-1.

[0200] (2) Under nitrogen atmosphere, add 0.06 mol (21.40 g) of intermediate K-1 to a three-necked flask, add a mixed solvent (300 ml toluene, 90 ml H2O) to dissolve it, stir for 1 hour under nitrogen, then slowly add 0.05 mol (6.10 g) of raw material C-1, 0.1 mol (13.82 g) of K2CO3, and 0.005 mol (5.78 g) of Pd(PPh3)4, heat to 90°C, react for 8 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Cool naturally, filter, and rotary evaporate the filtrate, and pass it through a silica gel column to obtain intermediate Q-1.

[0201] (3) Under nitrogen atmosphere, add 0.06mol (21.23g) of intermediate Q-1 to a three-necked flask, add a mixed solvent (300ml toluene, 90ml H2O) to dissolve it, stir for 1 hour under nitrogen, then slowly add 0.05mol (7.82g) of raw material D-1, 0.1mol (13.82g) K2CO3, 0.005mol (5.78g) Pd(PPh3)4, heat to 95°C, react for 10 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Naturally cool, filter, rotary evaporate the filtrate, and pass it through a silica gel column to obtain intermediate M-1. The synthesis of other intermediates M-2 to intermediate M-7 is similar to the synthesis method of intermediate M-1, and its specific raw materials are shown in Table 1 below:

[0202] Table 1

[0203]

[0204]

[0205] Synthesis of intermediate M-8:

[0206]

[0207] (1) Under nitrogen atmosphere, 0.06 mol (19.04 g) of raw material B-4 was added to a three-necked flask, and a mixed solvent (300 ml toluene, 90 ml H2O) was added to dissolve it. The mixture was stirred for 1 hour under nitrogen atmosphere, and then 0.05 mol (14.36 g) of raw material E-1, 0.1 mol (13.82 g) of K2CO3, and 0.004 mol (4.62 g) of Pd(PPh3)4 were slowly added. The mixture was heated to 90°C and reacted for 7 hours. The reaction was observed by thin layer chromatography (TLC) until the reaction was complete. The mixture was cooled naturally, filtered, and the filtrate was evaporated by rotary evaporation and passed through a silica gel column to obtain intermediate L-1.

[0208] (2) Under nitrogen atmosphere, add 0.06mol (25.97g) of intermediate L-1 to a three-necked flask, add a mixed solvent (300ml toluene, 90ml H2O) to dissolve it, stir for 1.5 hours under nitrogen, then slowly add 0.05mol (6.10g) of raw material C-1, 0.1mol (13.82g) K2CO3, 0.005mol (5.78g) Pd(PPh3)4, heat to 90°C, react for 8 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Naturally cool, filter, rotary evaporate the filtrate, and pass it through a silica gel column to obtain intermediate M-8. The synthesis of other intermediates M-9 to intermediate M-12 is similar to the synthesis method of intermediate M-8, and its specific raw materials are shown in Table 2 below:

[0209] Table 2

[0210]

[0211] Synthesis of intermediate R-1:

[0212]

[0213] Under nitrogen atmosphere, add 0.06mol (11.73g) of raw material H-1 to a three-necked flask, add a mixed solvent (300ml toluene, 90ml H2O) to dissolve it, stir for 1 hour under nitrogen, then slowly add 0.05mol (6.10g) of raw material C-1, 0.1mol (13.82g) K2CO3, 0.0052mol (6.01g) Pd(PPh3)4, heat to 90°C, react for 8 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain intermediate R-1. The synthesis of other intermediates R-2 to intermediate R-10 is similar to the synthesis method of intermediate R-1, and its specific raw materials are shown in Table 3 below:

[0214] Table 3

[0215]

[0216]

[0217] Synthesis of intermediate P-1:

[0218]

[0219] Under nitrogen atmosphere, add 0.06mol (7.90g) of raw material H-3 to a three-necked flask, add a mixed solvent (300ml toluene, 90ml H2O) to dissolve it, stir for 1.5 hours with nitrogen, then slowly add 0.05mol (6.10g) of raw material C-1, 0.1mol (13.82g) K2CO3, 0.005mol (5.78g) Pd(PPh3)4, heat to 95°C, react for 10 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Naturally cool, filter, rotary evaporate the filtrate, and pass through a silica gel column to obtain intermediate P-1. The synthesis of other intermediates P-2 to intermediate P-9 is similar to the synthesis method of intermediate P-1, and its specific raw materials are shown in Table 4 below:

[0220] Table 4

[0221]

[0222]

[0223] Example 2: Synthesis of Compound 23

[0224]

[0225] (1) In a three-necked flask, under nitrogen protection, add 0.01 mol (2.42 g) of intermediate R-3, 0.012 mol (2.63 g) of raw material F-1, and 150 ml of toluene, stir and mix, then add 4.5×10 -5 mol(0.041g)Pd2(dba)3,4.5×10 -5 mol (0.010g) tri-tert-butyl phosphine, 0.03mol (2.88g) sodium tert-butoxide, heated to 110°C, refluxed for 18 hours, sampling point plate, showing no raw material F-1 remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated until there was no fraction, passed through a neutral silica gel column to obtain intermediate N-1.

[0226] (2) In a three-necked flask, under nitrogen protection, add 0.01 mol (4.25 g) of intermediate N-1, 0.012 mol (5.21 g) of intermediate M-4, and 150 ml of toluene, stir and mix, then add 5×10 -5 mol(0.046g)Pd2(dba)3,5×10 - 5 mol (0.010g) tri-tert-butylphosphine, 0.03mol (2.88g) sodium tert-butoxide, heated to 115°C, refluxed for 16 hours, sampled the plate, showed no intermediate N-1 remained, the reaction was complete; cooled naturally to room temperature, filtered, the filtrate was evaporated until there was no fraction, passed through a neutral silica gel column, and compound 23 was obtained. Elemental analysis structure (molecular formula C 62 H 34 D8N2): Elemental analysis test value: C, 90.43; H, 6.14; N, 3.42. LC-MS: Measured value: 823.27 ([M+H] + ).

[0227] The following compounds were prepared in the same manner as in Example 2, and the synthetic raw materials are shown in Table 5 below;

[0228] Table 5

[0229]

[0230]

[0231]

[0232]

[0233] Example 3: Synthesis of Compound 540

[0234]

[0235] In a three-necked flask, under nitrogen protection, 0.01 mol (3.71 g) of raw material H-5, 0.012 mol (5.22 g) of intermediate M-7, and 150 ml of toluene were added and stirred, and then 5.3 × 10 -5 mol(0.049g)Pd2(dba)3,5.3×10 -5 mol (0.011g) tri-tert-butylphosphine, 0.03mol (2.88g) sodium tert-butoxide, heated to 115°C, refluxed for 14 hours, sampled and plated, showing no intermediate M-7 remaining, the reaction was complete; cooled naturally to room temperature, filtered, the filtrate was evaporated until there was no fraction, and passed through a neutral silica gel column to obtain compound 540. Elemental analysis structure (molecular formula C 58 H 35 D5N2): Elemental analysis test value: C, 90.48; H, 5.85; N, 3.67. LC-MS: Measured value: 770.41 ([M+H] + ).

[0236] Example 4: Synthesis of Compound 598

[0237]

[0238] In a polytetrafluoroethylene container, add 1.5mmol (0.34g) PtO2, 100mLD2O, 30mmol (0.5g) raw material A-1. The container is placed in an autoclave, sealed and heated at 250°C for 15 hours. The container is then cooled to room temperature. The mixture in the container is extracted several times with dichloromethane. The combined organic layer is dried with Na2SO4 and concentrated in vacuo. The crude product is purified by silica gel column chromatography to obtain intermediate J-1.

[0239]

[0240] Under H2 atmosphere, 10% Pd / C (30 mg) and 10% Pt / C (75 mg) were added to a solution of raw material B-1 (0.64 g, 2.0 mmol) in D2O (12 mL), and the reaction mixture was heated in a sealed tube at 180 ° C for 24 h, and after cooling, the reaction mixture was treated with methanol (40 mL), stirred, and the catalyst was filtered. The filtrate was concentrated under reduced pressure, and the residue was triturated with n-hexane, filtered and dried in an oven to obtain the desired intermediate Y-1.

[0241]

[0242]

[0243] (1) In a three-necked flask, under nitrogen protection, add 0.01 mol (1.76 g) of intermediate J-1, 0.012 mol (3.85 g) of intermediate Y-1, and 150 ml of toluene, stir and mix, then add 4×10 -5 mol(0.037g)Pd2(dba)3,4×10 - 5 mol (0.008g) tri-tert-butyl phosphine, 0.03mol (2.88g) sodium tert-butoxide, heated to 115°C, refluxed for 23 hours, sampling point plate, showed no intermediate J-1 remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated until there was no fraction, passed through a neutral silica gel column, and intermediate Z-1 was obtained.

[0244] (2) Under nitrogen atmosphere, add 0.06 mol (22.0 g) of intermediate Z-1 to a three-necked flask, add a mixed solvent (300 ml toluene, 90 ml H2O) to dissolve it, stir for 1 hour under nitrogen, then slowly add 0.05 mol (6.35 g) of raw material C-2, 0.1 mol (13.82 g) of K2CO3, and 0.005 mol (5.78 g) of Pd(PPh3)4, heat to 95°C, react for 9 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Cool naturally, filter, and rotary evaporate the filtrate, and pass it through a silica gel column to obtain intermediate X-1.

[0245] (3) Under nitrogen atmosphere, add 0.06 mol (22.14 g) of intermediate X-1 to a three-necked flask, add a mixed solvent (300 ml toluene, 90 ml H2O) to dissolve it, stir for 1 hour under nitrogen, then slowly add 0.05 mol (8.02 g) of raw material D-3, 0.1 mol (13.82 g) of K2CO3, and 0.006 mol (6.93 g) of Pd(PPh3)4, heat to 95°C, react for 11 hours, and observe the reaction by thin layer chromatography (TLC) until the reaction is complete. Cool naturally, filter, and rotary evaporate the filtrate, and pass it through a silica gel column to obtain intermediate W-1.

[0246] (4) In a three-necked flask, under nitrogen protection, add 0.01 mol (3.91 g) of intermediate N-5, 0.012 mol (5.40 g) of intermediate W-1, and 150 ml of toluene, stir and mix, then add 5.4×10 -5 mol(0.050g)Pd2(dba)3,5.4×10 -5mol (0.011 g) tri-tert-butylphosphine, 0.03 mol (2.88 g) sodium tert-butoxide, heated to 115°C, refluxed for 21 hours, sampled the plate, showed no intermediate N-5 remained, the reaction was complete; cooled to room temperature naturally, filtered, the filtrate was evaporated until there was no fraction, passed through a neutral silica gel column, and compound 598 was obtained. Elemental analysis structure (molecular formula C 58 HD 39 N2): Elemental analysis test value: C, 86.68; H, 9.87; N, 3.44. LC-MS: Measured value: 804.31 ([M+H] + ).

[0247] The following describes in detail the application effect of the synthesized mechanical functional material of the present invention in the device through device examples 1-35 and device comparative examples 1-10. The device manufacturing process of device examples 1-25 and device comparative examples 2-5 of the present invention is exactly the same as that of device comparative example 1, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also consistent. The difference is that the light-emitting auxiliary layer material in the device is replaced.

[0248] Compared with device comparative example 1, device embodiments 26-35 and device comparative examples 6-10 of the present invention have exactly the same manufacturing process, and use the same substrate material and electrode material, and the film thickness of the electrode material is also consistent. The only difference is that the light-emitting auxiliary layer material and the light-emitting layer doping material in the device are replaced.

[0249] Preparation of organic electroluminescent devices

[0250] Device Comparison Example 1

[0251] The organic electroluminescent device was prepared by following the steps below:

[0252] like Figure 1As shown, the glass substrate layer 1 is an anode layer 2 (Ag (100nm)) formed by vacuum evaporation. On the anode layer 2, a vacuum evaporation device is used to evaporate HT1 and HI1 with a film thickness of 10nm as a hole injection layer 3, and the mass ratio of HT1 and HI1 is 97:3. Then, HT1 with a thickness of 120nm is evaporated as a hole transport layer 4. Then, EB-1 with a thickness of 10nm is evaporated as a light-emitting auxiliary layer 5. After the evaporation of the above-mentioned light-emitting auxiliary materials is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared, and its structure includes BH1 used as the main material of the OLED light-emitting layer 6, BD1 as the doping material, the doping ratio of the doping material is 3% by weight, and the thickness of the light-emitting layer is 20nm. After the above-mentioned light-emitting layer 6, HB1 is continuously evaporated with a film thickness of 5nm as a hole blocking layer 7. On top of the above-mentioned hole blocking layer 7, ET-1 and Liq are continuously evaporated, and the mass ratio of ET-1 and Liq is 1:1. The vacuum-evaporated film thickness of the material is 30 nm, and this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is made by a vacuum evaporation device, and this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 16 nm is made by a vacuum evaporation device, and the mass ratio of Mg to Ag is 1:9, and this layer is used as the cathode layer 10. On the cathode layer 10, 65 nm of CP-1 is vacuum-evaporated as a covering layer 11.

[0253] The specific structures of device examples 1-35 and device comparative examples 2-10 are shown in Table 6.

[0254] The molecular structure formula of the relevant materials is shown below:

[0255]

[0256]

[0257] Among them, boron nitrogen materials BD1 and BD2 come from the structure synthesized in patent CN111357128A, BD3 comes from the structure synthesized in patent JP2021064779A, and BD4, BD5, BD6, BD7, BD8, EB-1, EB-2, EB-3, EB-4, EB-5, EB-6, EB-7, EB-8, EB-9, and EB-10 are all prior art.

[0258] Table 6

[0259]

[0260]

[0261]

[0262] In the above table, taking Example 1 as an example, "HI1:HT1=3:9710nm" in the second column means that the materials used for the hole injection layer are compound HT1 and P-type doping material HI1, 3:97 means that the weight ratio of P-type doping material HI and compound HT1 is 3:97, and 10nm means the thickness of the layer; "210nm" in the fourth column means that the material used is compound 2, and the thickness of the layer is 10nm. The meanings in other tables can be deduced by analogy.

[0263] After the OLED light emitting device is prepared as described above, the cathode and the anode are connected by a known driving circuit, and various properties of the device are measured. The measured performance results of the devices of Comparative Examples 1-10 and Examples 1-35 are shown in Table 7.

[0264] Table 7

[0265]

[0266] Note: LT95 refers to the current density of 30mA / cm 2 The time taken for the device brightness to decay to 95% of the original brightness under the condition of 100V. The current efficiency and color coordinates were tested using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.) at a current density of 10 mA / cm 2 The life test system is the EAS-62C OLED life test system produced by Japan System Research Co., Ltd.

[0267] It can be seen from the device data results in Table 7 that compared with device comparison examples 1-10, the deuterated aromatic amine compounds applied in the present invention can effectively improve the device life compared with the undeuterated aromatic amine compounds as the light-emitting auxiliary layer material. The deuterated aromatic amine compounds applied in the present invention and the devices prepared by using boron nitrogen materials in the light-emitting layer can effectively improve the device life, and the device efficiency is also improved to a certain extent.

[0268] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are exhaustively listed. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0269] For those skilled in the art, several modifications and improvements may be made without departing from the concept of the present invention, all of which belong to the protection scope of the present invention. The protection scope of the present invention shall be based on the attached claims.

Claims

1. An organic electroluminescent device, comprising a substrate, a first electrode, an organic functional layer and a second electrode in sequence, characterized in that: The organic functional layer includes a hole transport region, a light emitting region and an electron transport region; The light-emitting region comprises a compound represented by formula (1); The hole transport region comprises a compound represented by formula (2); In formula (1), C and D are independently represented by R-substituted or unsubstituted C6-C 30 Aromatic ring, R substituted or unsubstituted 5-30 membered heteroaromatic ring, R substituted or unsubstituted C6-C 30 aliphatic ring; Ar1 and Ar2 are independently represented by R substituted or unsubstituted C6-C 30 Aryl, R substituted or unsubstituted 5-30 membered heteroaryl, R substituted or unsubstituted C6-C 30 aliphatic cyclic group; The R may be the same or different each time and may be a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The R a , R b , R c Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups; The heteroatoms in the heteroaryl group are selected from one or more of O, S, N, Si, and B; In formula (2), R1 and R2 are independently substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene; The p and q are independently represented by the numbers 0, 1, 2, 3 or 4, and p+q≧1; The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring; The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom is selected from one or more of oxygen atoms, sulfur atoms and nitrogen atoms.

2. The organic electroluminescent device according to claim 1, characterized in that: The light-emitting region comprises a host material and a doping material, and the doping material comprises a compound represented by formula (1).

3. The organic electroluminescent device according to claim 1, characterized in that: The hole transport region comprises a hole injection layer, a hole transport layer and a light-emitting layer auxiliary layer in sequence, and the light-emitting auxiliary layer comprises a compound represented by formula (2); preferably, the hole injection layer comprises an aromatic amine compound and an alkylene compound.

4. The organic electroluminescent device according to claim 1, characterized in that: The formula (1) is represented by any one of the following formulas (1-1) to (1-5): In formula (1-1) to formula (1-5), Ar1 and Ar2 are independently represented by R-substituted or unsubstituted C6-C 30 Aryl, R substituted or unsubstituted 5-30 membered heteroaryl, R substituted or unsubstituted C6-C 30 aliphatic ring; The R may be the same or different each time and may be a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R m Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The X represents one of C(Q1)(Q2), Si(Q3)(Q4), N-Q5, O, and S, wherein Q1, Q2, Q3, Q4, and Q5 represent substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

5. The organic electroluminescent device according to claim 1, characterized in that: The formula (1) is expressed as any one of the following formulas (1-6) to (1-7): In formula (1-6) to formula (1-7), the R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R m , R n , R o , R p , R q , R s , R f , R w , R x , R y , R z Each occurrence of the same or different radicals may be represented by a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Alkynyl, substituted or unsubstituted C1~C 10 Alkoxy, substituted or unsubstituted C1~C 10 Aryloxy, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 one of a heteroaryl group, and a substituted or unsubstituted borane group; The X represents one of C(Q1)(Q2), Si(Q3)(Q4), N-Q5, O, and S, wherein Q1, Q2, Q3, Q4, and Q5 represent substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The substituents of the above-mentioned substitutable groups may be selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any one or more of heteroaryl groups; The heteroatom in the heteroaryl group may be selected from one or more of O, S, N, Si and B.

6. The organic electroluminescent device according to any one of claims 1 to 5, characterized in that: The C and D represent the following groups which are substituted or unsubstituted by R: any one of phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazolyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl and spirofluorenyl; The R represents a deuterium atom, a tritium 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, linoyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; The R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R m , R n , R o , R p , R q , R s , R f , R w , R x , R y , R z Each of the above is independently a hydrogen atom, a deuterium atom, a tritium 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; Ar1 and Ar2 are independently substituted or unsubstituted 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; The Q1, Q2, Q3, Q4, and Q5 are independently substituted or unsubstituted 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 biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amine, substituted or unsubstituted triazinyl; The substituent for the substituent group is optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furanyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthryl group. Preferably, the R a , R b , R c , R d , R e , R f , R h , R i , R j , R k , R m , R n , R o , R p , R q , R s , R f , R w , R x , R y , R z They are independently represented as follows: Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl, Any of; The Ar1 and Ar2 are represented by the following structures: Any one of.

7. A deuterium-containing aromatic amine compound, characterized in that: The structure of the deuterium-containing aromatic amine compound is shown in formula (2); In formula (2), R1 and R2 are independently substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene; The p and q are independently represented by the numbers 0, 1, 2, 3 or 4, and p+q≧1; The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring; The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom is selected from one or more of oxygen atoms, sulfur atoms or nitrogen atoms. At least one hydrogen atom in the compound represented by formula (2) is replaced by a deuterium atom.

8. The organic electroluminescent device according to claim 1, characterized in that: The formula (2) represents any one of formula (2-1) to formula (2-2): In formula (2-1)-formula (2-2), R1 and R2 are independently represented by substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene; The p and q are independently represented by the numbers 0, 1, 2, 3 or 4, and p+q≧1; The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring; The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom is selected from one or more of oxygen atoms, sulfur atoms and nitrogen atoms.

9. The organic electroluminescent device according to claim 1, characterized in that: The formula (2) represents any one of formulas (2-3) to (2-8): In formula (2-1)-formula (2-2), R1 and R2 are independently represented by substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The R3 and R4 are independently represented by a deuterium atom, a substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted 5-30 membered heteroaryl; The L1 and L2 are independently represented by a direct bond, a substituted or unsubstituted C6-C 30 Arylene, substituted or unsubstituted 5-30 membered heteroarylene; The p and q are independently represented by the numbers 0, 1, 2, 3 or 4; The R5-R 12 Each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted 5-30 membered heteroaryl, and R5-R 12 Any two adjacent groups can be fused to form a ring; The substituents of the above-mentioned substitutable groups can be selected from deuterium atoms, cyano groups, halogen groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom is selected from one or more of oxygen atoms, sulfur atoms and nitrogen atoms.

10. The organic electroluminescent device according to claim 1, characterized in that: The formula (2) represents any one of formulas (2-9) to (2-16): Preferably, the formula (2) represents any one of formula (2-17) to formula (2-24): Preferably, the formula (2) represents any one of formula (2-25) to formula (2-28): Said R1 and R2 are independently represented by substituted or substituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted carbazolyl; The L1 and L2 are independently represented by a direct bond, a phenylene group, a naphthylene group or a biphenylene group; The substituents are selected from one or more of deuterium atoms, cyano groups, halogen groups, phenyl groups, naphthyl groups, biphenyl groups, methyl groups, tert-butyl groups, and adamantyl groups.

11. The organic electroluminescent device according to claim 1, characterized in that: Said R1 and R2 are respectively represented by any of the following structures: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted indenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted indolyl; The L1 and L2 are respectively one of a single bond, a substituted or substituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; The R5-R 12 Respectively represent any of the following structures: one of a hydrogen atom, a methyl group, a deuterated methyl group, an ethyl group, a tert-butyl group, a phenyl group, an adamantyl group, a naphthyl group, and a biphenyl group; The substituent replacing the above substitutable group is selected from one or more of a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a carbazolyl group, a phenanthryl group, a dibenzothienyl group, and a benzofuranyl group; Preferably, R1, R2, R3, and R4 are respectively represented by any of the following structures: The L1 and L2 are respectively represented by a direct bond or any of the structures shown below:

12. The organic electroluminescent device according to claim 1, characterized in that: The formula (2) is selected from any one of the following specific structures: The formula (1) is selected from any one of the following specific structures:

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