An organic compound with triarylamine as core and its application

Abstract

The present invention discloses an organic compound with triarylamine as the core and its application, belonging to the field of semiconductor technology. The structure of the organic compound with triarylamine as the core of the present invention is shown in general formula (1); the organic compound of the present invention has a higher triplet energy level and a wider band gap, and also has a higher mobility. The device using the organic compound provided by the present invention can effectively improve the life of the OLED device through structural optimization.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and in particular to an organic compound with triarylamine as a core and application thereof. Background Art

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

[0003] The OLED optoelectronic functional material film layer that constitutes the OLED device includes at least two layers of structure. The OLED device structure used in the industry includes multiple film layers such as hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, and electron injection layer. In other words, the optoelectronic functional materials used in OLED devices at least include hole injection materials, hole transport materials, light-emitting materials, and electron transport materials. The material types and matching forms are rich and diverse. In addition, for the matching of OLED devices with different structures, the optoelectronic functional materials used have strong selectivity, and the performance of the same material in devices with different structures may also be completely different.

[0004] Therefore, in view of the current industrial application requirements of OLED devices, the different functional film layers of OLED devices, and the optoelectronic properties of the devices, it is necessary to select more suitable OLED functional materials or material combinations with high performance to achieve the comprehensive characteristics of high efficiency, long life and low voltage of the devices.

[0005] Generally, if an OLED device is driven or stored in a high temperature environment, adverse effects such as changes in color light, reduced luminous efficiency, increased driving voltage, and shortened luminous life will occur. In order to prevent the above adverse effects, the hole transport side material is required to have a higher glass transition temperature and better heat resistance stability. However, for compounds with high symmetry or high planarity and multiple aromatic groups in the molecule, crystallization is likely to occur and block the outlet of the crucible used for evaporation, or crystallization may cause film defects, resulting in low yield of OLED devices. In addition, for compounds with multiple aromatic groups in the molecule, although they have a higher glass transition temperature, considering the high sublimation temperature, decomposition during evaporation or uneven evaporation may occur, and thus there is a problem of short life.

[0006] Although there are many reports on amine compounds in which N-carbazole is bonded to amine via an aromatic group, the performance of these compounds as OLED devices is not sufficient, and the development of OLED devices with better performance is highly anticipated. Summary of the invention

[0007] In view of the above problems existing in the prior art, the applicant of the present invention provides an organic compound with triarylamine as the core and its application in an organic electroluminescent device. The organic compound provided by the present invention has a higher triplet energy level and a wider band gap, a higher mobility, and excellent industrial processing performance. The device using the organic compound provided by the present invention can effectively improve the life of the OLED device through structural optimization.

[0008] The technical solution of the present invention is as follows:

[0009] An organic compound with triarylamine as the core, the structure of the organic compound is shown in the general formula (1):

[0010]

[0011] A and B are independently represented by hydrogen atom, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, and the connection mode of A and B with general formula (1) is single substitution or forming a ring;

[0012] R2 and R3 are independently represented by a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a biphenyl group, a carbazole group, a structure represented by the general formula (2), the general formula (3) or the general formula (4), and at least one of R2 and R3 is represented by the structure represented by the general formula (2), the general formula (3) or the general formula (4), and R2 is not represented by the structure represented by the general formula (2);

[0013] Said R0, R1, and R4 are independently represented by hydrogen atoms, deuterium atoms, phenyl groups, dibenzofuranyl groups, naphthyl groups, biphenyl groups, or carbazole groups, and at least two of R0, R1, R2, R3, and R4 are not represented by hydrogen atoms or deuterium atoms; when R3 is represented by the general formula (2), R1 is represented by a hydrogen atom;

[0014]

[0015] The m, n, p, and q are independently represented by the number 1 or 2;

[0016] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with general formula (2) includes two connection modes: substitution and cyclization; the connection mode of R5 and R6 with general formula (3) or general formula (4) includes two connection modes: substitution and cyclization;

[0017] R7 is a hydrogen atom, a deuterium atom, a phenyl group, a naphthyl group or a biphenyl group;

[0018] The substituent of the substitutable group may be selected from a deuterium atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group or a carbazolyl group.

[0019] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), R1 and R4 are hydrogen atoms, and only one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl.

[0020] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), R3 and R4 are hydrogen atoms, and only one of R1 and R0 is phenyl, carbazolyl or dibenzofuranyl.

[0021] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), R3 and R4 are hydrogen atoms, at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and at least one of A and B is represented by phenyl, naphthyl or dibenzofuranyl.

[0022] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), R1 and R4 are hydrogen atoms, at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and at least one of A and B is represented by phenyl, naphthyl or dibenzofuranyl.

[0023] In a preferred embodiment, only two of R0, R3, R4, R1 and R2 are not hydrogen atoms or deuterium atoms.

[0024] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), and at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl.

[0025] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), and at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl.

[0026] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and R3 and R4 are represented by hydrogen atoms.

[0027] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and at least one of A and B is represented by phenyl, naphthyl, phenanthryl or dibenzofuranyl.

[0028] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and at least one of A and B is represented by phenyl, phenanthryl, naphthyl or dibenzofuranyl.

[0029] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), and at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and m+n=3.

[0030] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), and at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, and m+n=3.

[0031] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of R5 and R6 is represented by phenyl or benzofuranyl, and they are connected by a ring-bonding manner.

[0032] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of R5 and R6 is represented by phenyl or benzofuranyl, and they are connected by a ring-bonding manner.

[0033] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuran, and at least one of R5 and R6 is represented by phenyl, naphthyl or dibenzofuran, and they are connected by substitution.

[0034] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of R5 and R6 is represented by phenyl, naphthyl or benzofuran, and they are connected by substitution.

[0035] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of A and B is represented by phenyl or benzofuranyl, and they are connected by a ring-bonding manner.

[0036] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of A and B is represented by phenyl or benzofuranyl, and they are connected by a ring-bonding manner.

[0037] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of A and B is represented by phenyl, naphthyl, phenanthryl or dibenzofuranyl, and they are connected by substitution.

[0038] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, at least one of A and B is represented by phenyl, phenanthryl, naphthyl or dibenzofuranyl, and they are connected by substitution.

[0039] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), one and only one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, R3 and R4 are represented by hydrogen atoms, and at least one of R5 and R6 is represented by phenyl or benzofuranyl, and they are connected by a ring-bonding manner.

[0040] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), one and only one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuran, R1 and R4 are represented by hydrogen atoms, and at least one of R5 and R6 is represented by phenyl, naphthyl or dibenzofuran, and they are connected by substitution.

[0041] In a preferred embodiment, R2 is represented by the structure shown in general formula (3) or general formula (4), at least one of R1 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, R3 and R4 are represented by hydrogen atoms, at least one of A and B is represented by phenyl, naphthyl, phenanthryl or dibenzofuranyl, and they are connected by substitution.

[0042] In a preferred embodiment, R3 is represented by the structure shown in general formula (2), general formula (3) or general formula (4), at least one of R2 and R0 is represented by phenyl, naphthyl, biphenyl, carbazole or dibenzofuranyl, R1 and R4 are represented by hydrogen atoms, at least one of A and B is represented by phenyl, phenanthryl, naphthyl or dibenzofuranyl, and they are connected by substitution.

[0043] Preferably, the structure of the organic compound is as shown in general formula (1-1):

[0044]

[0045] In the general formula (1-1), the * represents a connection site;

[0046] A and B are independently represented by hydrogen atom, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, and the connection mode of A and B with general formula (1-1) is single substitution or forming a ring;

[0047] The R3 is a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a biphenyl group, a carbazole group, or a structure represented by the general formula (2), the general formula (3) or the general formula (4);

[0048] The R2 is a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a biphenyl group, a carbazole group, or a structure represented by the general formula (3) or the general formula (4);

[0049] At least one of R2 and R3 is represented by the structure of general formula (2), general formula (3) or general formula (4);

[0050] Said R0, R1, and R4 are independently represented by hydrogen atoms, deuterium atoms, phenyl groups, dibenzofuranyl groups, naphthyl groups, biphenyl groups, or carbazole groups, and at least two of R0, R1, R2, R3, and R4 are not represented by hydrogen atoms or deuterium atoms; when R3 is represented by the general formula (2), R1 is represented by a hydrogen atom;

[0051]

[0052] The m, n, p, and q are independently represented by the number 1 or 2;

[0053] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with general formula (2), general formula (3) or general formula (4) is substitution and cyclization;

[0054] The R7 is a hydrogen atom, a deuterium atom, a phenyl group, a naphthyl group or a biphenyl group;

[0055] The substituent of the substitutable group may be selected from a deuterium atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group or a carbazolyl group.

[0056] In a preferred embodiment, in the general formula (1-1), A is represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (1-1) is a monosubstituted group or a cyclic group;

[0057] The B is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection between B and the general formula (1-1) is a monosubstituted or cyclic form;

[0058] The R3 is represented by the structure shown in the general formula (2) or the general formula (4);

[0059] R2 is a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group or a carbazole group;

[0060] The R0, R1, and R4 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a biphenyl group, or a carbazole group, and at least one of R0, R1, R2, and R4 is not represented by a hydrogen atom or a deuterium atom; when R3 is represented by the general formula (2), R1 is represented by a hydrogen atom;

[0061] The m and n are independently represented by the number 1 or 2;

[0062] The p and q are independently represented by the number 1;

[0063] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and R5 and R6 are connected with the general formula (2) or the general formula (4) in two ways: substitution and cyclization;

[0064] The R7 is a hydrogen atom or a deuterium atom;

[0065] The substituent of the substitutable group may be selected from a deuterium atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group or a carbazolyl group.

[0066] Preferably, in the general formula (1-1), R1 and R4 are independently represented by a hydrogen atom or a deuterium atom;

[0067] The R2 represents a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group;

[0068] The R0 represents a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group;

[0069] and only one of R0 and R2 is phenyl, naphthyl, biphenyl or dibenzofuranyl;

[0070] Preferably, the structure of the organic compound is shown in general formula (A-1):

[0071]

[0072] The * indicates the connection site;

[0073] A is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (A-1) is a monosubstituted group or a cyclic group;

[0074] The B is represented by a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection mode between B and the general formula (A-1) is a monosubstituted or cyclic form;

[0075] The m and n are independently represented by the number 1 or 2;

[0076] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl group or benzofuranyl group, and the connection mode of R5 and R6 with the general formula (A-1) includes substitution and cyclization;

[0077] The R2 represents a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group;

[0078] The R0 represents a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group;

[0079] and only one of R0 and R2 is phenyl, naphthyl, biphenyl or dibenzofuranyl;

[0080] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0081] In a preferred embodiment, in the general formula (1-1), A is represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (1-1) is a monosubstituted group or a cyclic group;

[0082] The B is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection between B and the general formula (1-1) is a monosubstituted or cyclic form;

[0083] The R3 is represented by the structure shown in the general formula (3);

[0084] R2 is a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group or a carbazole group;

[0085] R0, R1, and R4 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group, or a carbazole group, and at least one of R0, R1, R2, and R4 is not represented by a hydrogen atom or a deuterium atom;

[0086] The m and n are independently represented by the number 1 or 2;

[0087] The p and q are independently represented by the number 1;

[0088] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with the general formula (3) is substitution and cyclization;

[0089] The R7 is a hydrogen atom or a deuterium atom;

[0090] The substituent of the substitutable group may be selected from a deuterium atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group or a carbazolyl group.

[0091] Preferably, in the general formula (1-1), R1 and R4 are independently represented by a hydrogen atom or a deuterium atom;

[0092] The R2 is a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a biphenyl group, or a carbazole group;

[0093] The R0 represents a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group or a carbazole group;

[0094] And only one of R0 and R2 is phenyl, naphthyl, biphenyl or dibenzofuranyl.

[0095] Preferably, the structure of the organic compound is as shown in the general formula (B-1) or (B-2):

[0096]

[0097] In the general formula (B-1) and (B-2), A is represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode between A and the general formula (B-1) or the general formula (B-2) is a monosubstituted group or a cyclic group;

[0098] The m is represented by the number 1 or 2;

[0099] The R2 represents a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group;

[0100] The R0 represents a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group;

[0101] and only one of R0 and R2 is phenyl, naphthyl, biphenyl or dibenzofuranyl;

[0102] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with general formula (B-1) or general formula (B-2) includes substitution and cyclization;

[0103] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0104] Preferably, the structure of the organic compound is as shown in the general formula (C-1) or (C-2):

[0105]

[0106] In the general formulas (C-1) and (C-2), the * represents a connection site;

[0107] A is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A with the general formula (C-1) or the general formula (C-2) is a monosubstituted group or a cyclic group;

[0108] B is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection between B and the general formula (C-1) or the general formula (C-2) is a monosubstituted or cyclic form;

[0109] The m and n are independently represented by the number 1 or 2;

[0110] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with general formula (C-1) or general formula (C-2) includes substitution and cyclization;

[0111] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0112] In a preferred embodiment, in the general formula (1-1), A is represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (1-1) is a monosubstituted group or a cyclic group;

[0113] The B is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection between B and the general formula (1-1) is a monosubstituted or cyclic form;

[0114] The R3 represents a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group or a carbazole group;

[0115] The R2 is represented by the structure shown in the general formula (4);

[0116] R0, R1, and R4 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group, or a carbazole group, and at least one of R0, R1, R3, and R4 is not represented by a hydrogen atom or a deuterium atom;

[0117] The m and n are independently represented by the number 1 or 2;

[0118] The p and q are independently represented by the number 1;

[0119] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with the general formula (4) is substitution and cyclization;

[0120] The R7 is a hydrogen atom or a deuterium atom;

[0121] The substituent of the substitutable group may be selected from a deuterium atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group or a carbazolyl group.

[0122] Preferably, in the general formula (1-1), R3 and R4 are independently represented by a hydrogen atom or a deuterium atom;

[0123] Said R0 and R1 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group, and one and only one of R0 and R1 is represented by a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group;

[0124] Preferably, the structure of the organic compound is shown in the general formula (D-1):

[0125]

[0126] In the general formula (D-1), the * represents a connection site;

[0127] A is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (D-1) is a monosubstituted group or a cyclic group;

[0128] The B is represented by a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection mode between B and the general formula (D-1) is a single substitution or a cyclic formation;

[0129] The m and n are independently represented by the number 1 or 2;

[0130] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl group or benzofuranyl group, and the connection mode of R5 and R6 with the general formula (D-1) includes substitution and cyclization;

[0131] Said R0 and R1 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group, and one and only one of R0 and R1 is represented by a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group;

[0132] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0133] In a preferred embodiment, in the general formula (1-1), A is represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (1-1) is a monosubstituted group or a cyclic group;

[0134] The B is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection between B and the general formula (1-1) is a monosubstituted or cyclic form;

[0135] The R3 represents a hydrogen atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group or a carbazole group;

[0136] The R2 is represented by the structure shown in the general formula (3);

[0137] R0, R1, and R4 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group, a diphenyl group, or a carbazole group, and at least one of R0, R1, R3, and R4 is not represented by a hydrogen atom or a deuterium atom;

[0138] The m and n are independently represented by the number 1 or 2;

[0139] The p and q are independently represented by the number 1;

[0140] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with the general formula (3) is substitution and cyclization;

[0141] The R7 is a hydrogen atom or a deuterium atom;

[0142] The substituent of the substitutable group may be selected from a deuterium atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group or a carbazolyl group.

[0143] Preferably, in the general formula (1-1), R3 and R4 are independently represented by a hydrogen atom or a deuterium atom;

[0144] Said R0 and R1 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group, and one and only one of R0 and R1 is represented by a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group;

[0145] Preferably, the structure of the organic compound is shown in the general formula (E-1):

[0146]

[0147] In the general formula (E-1), A is represented by a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (E-1) is a monosubstituted group or a cyclic group;

[0148] The m is represented by the number 1 or 2;

[0149] Said R0 and R1 are independently represented by a hydrogen atom, a deuterium atom, a phenyl group, a dibenzofuranyl group, a naphthyl group or a biphenyl group, and one and only one of R0 and R1 is represented by a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group;

[0150] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl, naphthyl, biphenyl, benzofuranyl or carbazole, and the connection mode of R5 and R6 with the general formula (E-1) is substitution and cyclization;

[0151] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0152] Preferably, the structure of the organic compound is shown in general formula (F-1):

[0153]

[0154] In the general formula (F-1), the * represents a connection site;

[0155] A is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (F-1) is a monosubstituted group or a cyclic group;

[0156] The B is represented by a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection mode between B and the general formula (F-1) is a monosubstituted or cyclic form;

[0157] The m and n are independently represented by the number 1 or 2;

[0158] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl group or benzofuranyl group, and the connection mode of R5 and R6 with the general formula (F-1) includes substitution and cyclization;

[0159] The R0 represents phenyl, naphthyl, biphenyl or dibenzofuranyl;

[0160] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0161] Preferably, the structure of the organic compound is shown in the general formula (F-2):

[0162]

[0163] In the general formula (F-1), the * represents a connection site;

[0164] A is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and the connection mode of A to the general formula (F-1) is a monosubstituted group or a cyclic group;

[0165] The B is represented by a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted phenanthryl, and the connection mode between B and the general formula (F-1) is a monosubstituted or cyclic form;

[0166] The m and n are independently represented by the number 1 or 2;

[0167] R5 and R6 are independently represented by hydrogen atom, deuterium atom, phenyl group or benzofuranyl group, and the connection mode of R5 and R6 with the general formula (F-1) includes substitution and cyclization;

[0168] The R1 represents phenyl, naphthyl, biphenyl or dibenzofuranyl;

[0169] The substituent of the substitutable group may be selected from a deuterium atom, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group or a dibenzofuranyl group.

[0170] In a preferred embodiment, the organic compound with triarylamine as the core has a specific structure as follows:

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] One of (556).

[0187] The second aspect of the present invention is to provide the use of the above organic compound with triarylamine as the core in the preparation of organic electroluminescent devices.

[0188] The third aspect of the present invention is to provide an organic electroluminescent device, comprising a cathode, an anode and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode, and the organic functional layer contains the organic compound with the triarylamine as the core.

[0189] The fourth aspect of the present invention is to provide an organic electroluminescent device, comprising an electron blocking layer, wherein the electron blocking layer contains the organic compound with the triarylamine as the core.

[0190] The fifth aspect of the present invention is to provide an organic electroluminescent device having the following characteristics: the organic electroluminescent device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and an electron transport region, the electron blocking layer is adjacent to the light-emitting layer, the hole injection layer includes a P-doped material and an aromatic amine organic material, and the hole transport layer includes the same aromatic amine organic material as the hole injection layer.

[0191] The sixth aspect of the present invention is to provide an organic electroluminescent device having the following characteristics: the organic electroluminescent device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and an electron transport region, the electron blocking layer is adjacent to the light-emitting layer, the hole injection layer comprises a P-doped material and an aromatic amine organic material, the hole transport layer comprises the same aromatic amine organic material as the hole injection layer, and the electron blocking layer comprises a structure represented by general formula (1).

[0192] The seventh aspect of the present invention is to provide a full-color display device, which includes, from bottom to top, a substrate, a first electrode, an organic functional material layer and a second electrode, wherein the organic functional material layer includes: a hole transport region, which is located above the first electrode; a light-emitting layer, which is located above the hole transport region, and the light-emitting layer has a red light-emitting layer, a green light-emitting layer and a blue light-emitting layer, which are respectively composed in a red pixel region, a green pixel region and a blue pixel region; an electron transport region, which is located above the light-emitting layer; wherein the hole transport region includes, from bottom to top, a hole injection layer, a hole transport layer and an electron blocking layer, wherein the hole injection layer contains a P-type doping material, wherein the red pixel unit, the green pixel unit and the blue pixel unit have a common hole injection layer and a hole transport layer, and have respective electron blocking layers, wherein the blue pixel electron blocking layer contains an organic compound with a triarylamine as the core as described in general formula (1).

[0193] The eighth aspect of the present invention is to provide a lighting or display element having the following characteristics, comprising the above-mentioned organic electroluminescent device.

[0194] The beneficial technical effects of the present invention are:

[0195] The compounds provided by the present invention have relatively poor planarity and poor molecular equivalence compared to the comparative patents CN107459478A, KR101692253B1, and KR101891432B1, so that the compounds applied for by the present invention are not prone to blockage problems, and have a higher glass transition temperature and excellent film phase stability, which can effectively improve the problem of poor device life.

[0196] The compound of the present invention contains a carbazole group, which can transfer both electrons and holes, and can effectively improve the problem of interfacial charge accumulation under high current density, prevent exciton quenching, and improve device life.

[0197] The structure of the compound of the present invention has poor molecular planarity, which effectively reduces the intermolecular interaction force, so that the molecules have a lower evaporation temperature during evaporation, and are molten materials, so that the compound of the present invention has excellent industrial processing performance.

[0198] The compounds of the present invention contain substituted or unsubstituted carbazole groups, which have high electron tolerance. Since the EB layer is adjacent to the light-emitting layer, the material of this layer has high electron tolerance and can inhibit material degradation caused by electrons not consumed in the light-emitting layer (e.g., reduce or prevent), thereby allowing the OLED device to have a long life. BRIEF DESCRIPTION OF THE DRAWINGS

[0199] Figure 1This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0200] In the figure: 1 is a transparent substrate layer, 2 is an ITO 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 / electron transport layer, 8 is an electron injection layer, 9 is a cathode reflective electrode layer, and 10 is a light extraction layer.

[0201] Figure 2 It is the DSC spectrum of compound 2 of the present invention.

[0202] Figure 3 This is the DSC spectrum of compound 292 of the present invention.

[0203] Figure 4 This is the DSC spectrum of compound 336 of the present invention.

[0204] Figure 5 This is the DSC spectrum of compound 78 of the present invention.

[0205] Figure 6 It is the NMR spectrum of compound 2 of the present invention.

[0206] Figure 7 This is the NMR spectrum of compound 14 of the present invention.

[0207] Figure 8 This is the NMR spectrum of compound 244 of the present invention. DETAILED DESCRIPTION

[0208] The present invention is described in detail below in conjunction with the accompanying drawings and embodiments.

[0209] Example 1: Synthesis of Compound 1:

[0210]

[0211]

[0212] In a three-necked flask, under nitrogen protection, add 0.012 mol of raw material A-1, 0.01 mol of raw material B-1, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105°C, refluxed for 24 hours, sampled, and the plate showed no raw material B-1 remaining, indicating complete reaction; cooled naturally to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate E-1. Elemental analysis structure (molecular formula C 24 H 15BrClN): theoretical value C, 66.61; H, 3.49; Br, 18.46; N, 3.24; Cl, ​​8.19; found value: C, 66.63; H, 3.47; Br, 18.45; N, 3.22; Cl, ​​8.21. ESI-MS (m / z) (M + ): The theoretical value is 431.01, and the measured value is 431.14.

[0213] In a three-necked flask, under nitrogen protection, add 0.01 mol of raw material C-1, 0.012 mol of intermediate E-1, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105°C, refluxed for 24 hours, sampled, and the plate showed no C-1 residue, indicating complete reaction; cooled to room temperature, filtered, and the filtrate was evaporated under reduced pressure (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate F-1. Elemental analysis structure (molecular formula C 30 H 20 ClN): theoretical value C, 83.81; H, 4.69; N, 3.26; Cl, ​​8.25; found value: C, 83.79; H, 4.68; N, 3.28; Cl, ​​8.27. ESI-MS (m / z) (M + ): The theoretical value is 429.13, and the measured value is 429.32.

[0214] In a 250 ml three-necked flask, under a nitrogen atmosphere, 0.012 mol of raw material D-1, 0.01 mol of intermediate F-1, 0.03 mol of potassium tert-butoxide, 1×10 -4 mol Pd2(dba)3,1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, sample point plate, showed no intermediate F-1 remaining, the reaction was complete; natural cooling, filtration, rotary evaporation of the filtrate, silica gel column, to obtain the target compound 1; elemental analysis structure (molecular formula C 54 H 38 N2): theoretical value C, 90.72; H, 5.36; N, 3.92; measured value: C, 90.73; H, 5.34; N, 3.91. ESI-MS (m / z) (M + ): The theoretical value is 714.30, and the measured value is 714.43.

[0215] Example 2: Synthesis of Compound 2:

[0216]

[0217] In a 250 ml three-necked flask, under a nitrogen atmosphere, add 0.012 mol of raw material A-1, 0.01 mol of raw material B-2, 0.03 mol of potassium tert-butoxide, 1×10 -4 mol Pd2(dba)3,1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, sampled the plate, showed no raw material B-2 remaining, the reaction was complete; cooled naturally, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the intermediate E-2; elemental analysis structure (molecular formula C 30 H 21 BrClN): theoretical value C, 70.53; H, 4.14; Br, 15.64; N, 2.74; Cl, ​​6.94; measured value: C, 70.34; H, 4.18; Br, 15.65; N, 2.80; Cl, ​​6.96. ESI-MS (m / z) (M + ): The theoretical value is 509.05, and the measured value is 509.17.

[0218] In a three-necked flask, under nitrogen protection, add 0.012 mol of intermediate E-2, 0.01 mol of raw material C-2, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105°C, refluxed for 24 hours, sampled, and the plate showed no C-2 residue, indicating complete reaction; cooled to room temperature, filtered, and the filtrate was evaporated under reduced pressure (-0.09 MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate F-2. Elemental analysis structure (molecular formula C 48 H 33 ClN2): theoretical value C, 85.63; H, 4.94; N, 4.16; Cl, ​​5.27; measured value: C, 85.52; H, 4.96; N, 4.18; Cl, ​​5.29. ESI-MS (m / z) (M + ): The theoretical value is 672.23, and the measured value is 672.09.

[0219] In a three-necked flask, under nitrogen protection, add 0.01 mol of intermediate F-2, 0.012 mol of raw material D-2, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105°C, refluxed for 24 hours, sampled the plate, showed no intermediate F-2 remained, the reaction was complete; cooled to room temperature naturally, filtered, the filtrate was vacuum evaporated (-0.09MPa, 85°C), passed through a neutral silica gel column, and the target compound 2 was obtained. Elemental analysis structure (molecular formula C 54H 38 N2): theoretical value C, 90.72; H, 5.36; N, 3.92; measured value: C, 90.73; H, 5.37; N, 3.90. ESI-MS (m / z) (M + ): The theoretical value is 714.30, and the measured value is 714.29.

[0220] Example 3: Synthesis of Compound 3:

[0221]

[0222] In a three-necked flask, under nitrogen protection, add 0.012 mol of intermediate E-2, 0.01 mol of raw material C-3, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105°C, refluxed for 24 hours, sampled, and the plate showed no C-3 residue, indicating complete reaction; cooled naturally to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C), and passed through a neutral silica gel column to obtain intermediate F-3. Elemental analysis structure (molecular formula C 36 H 26 ClN): theoretical value C, 85.11; H, 5.16; N, 2.76; Cl, ​​6.98; found value: C, 85.03; H, 5.19; N, 2.82; Cl, ​​7.00. ESI-MS (m / z) (M + ): The theoretical value is 507.18, and the measured value is 507.31.

[0223] In a three-necked flask, under nitrogen protection, add 0.01 mol of intermediate F-3, 0.012 mol of raw material D-3, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105°C, refluxed for 24 hours, sampled the plate, showed no intermediate F-3 remained, the reaction was complete; cooled to room temperature naturally, filtered, the filtrate was vacuum evaporated (-0.09MPa, 85°C), passed through a neutral silica gel column, and the target compound 3 was obtained. Elemental analysis structure (molecular formula C 54 H 38 N2): theoretical value C, 90.72; H, 5.36; N, 3.92; measured value: C, 90.70; H, 5.35; N, 3.95. ESI-MS (m / z) (M + ): The theoretical value is 714.30, and the measured value is 714.35.

[0224] Example 4: Synthesis of Compound 252:

[0225]

[0226]

[0227] In a 250 ml three-necked flask, under a nitrogen atmosphere, 0.01 mol of raw material C-4, 0.012 mol of intermediate E-1, 0.03 mol of potassium tert-butoxide, 1×10 -4 mol Pd2(dba)3,1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, sample point plate, showed no raw material C-4 remaining, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, silica gel column, to obtain intermediate F-4; elemental analysis structure (molecular formula C 54 H 35 ClN2O): theoretical value C, 84.97; H, 4.62; N, 3.67; Cl, ​​4.64; measured value: C, 84.90; H, 4.65; N, 3.70; Cl, ​​4.62. ESI-MS (m / z) (M + ): The theoretical value is 764.24, and the measured value is 764.21.

[0228] In a three-necked flask, under nitrogen protection, add 0.012 mol of raw material D-2, 0.01 mol of intermediate F-4, 0.02 mol of sodium carbonate, 150 ml of toluene and 45 ml of water, stir and mix, then add 1×10 -4 mol Pd(PPh3)4, heated to 105℃, refluxed for 24 hours, sampled the plate, showed no intermediate F-4 remained, the reaction was complete; cooled to room temperature naturally, filtered, the filtrate was vacuum evaporated (-0.09MPa, 85℃), passed through a neutral silica gel column, and the target compound was obtained. Elemental analysis structure (molecular formula C 60 H 40 N2O): theoretical value C, 89.52; H, 5.01; N, 3.48; measured value: C, 89.47; H, 5.03; N, 3.50. ESI-MS (m / z) (M + ): The theoretical value is 804.31, and the measured value is 804.24.

[0229] The following compounds were prepared in the same manner as in Example 1, 2 or 3 (all raw materials were purchased from China Energy Conservation Wanrun Co., Ltd.), and the synthetic raw materials are shown in Table 1 below;

[0230] Table 1

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] The compounds of the present invention are used in light-emitting devices and can be used as electron blocking layer materials. The compounds prepared in the above embodiments of the present invention were tested for thermal properties, T1 energy level, and HOMO energy level, and the test results are shown in Table 2 and Table 2-1:

[0237] Table 2

[0238]

[0239]

[0240]

[0241] Table 2-1

[0242]

[0243] Note: The glass transition temperature Tg was measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter from NETZSCH, Germany), with a heating rate of 10°C / min; the thermal weight loss temperature Td was the temperature at which the weight loss was 1% in a nitrogen atmosphere, measured on a TGA-50H thermogravimetric analyzer from Shimadzu, Japan, with a nitrogen flow rate of 20 mL / min; the triplet energy level T1 was measured by a F4600 fluorescence spectrometer from Hitachi, and the material test conditions were 2*10 -5 mol / mL toluene solution; the highest occupied molecular orbital HOMO energy level is tested by photoelectron spectroscopy (IPS3), the test is in an atmospheric environment, the hole mobility test, the material of the present invention is made into a single charge device, and is measured by the SCLC method; Eg is tested by a UV spectrometer.

[0244] As can be seen from the data in the above table, the organic compound of the present invention has a high glass transition temperature, which can improve the phase stability of the material film and further improve the service life of the device; it has a higher T1 energy level, which can block the energy loss of the light-emitting layer, thereby improving the luminous efficiency of the device; a wider band gap (Eg) ensures that the compound of the present invention has no absorption in the visible light field; and a suitable HOMO energy level can solve the problem of carrier injection. Therefore, the compound with triarylamine as the core of the present invention can effectively improve the luminous efficiency and service life of the device after being applied to different functional layers of the OLED device.

[0245] Figure 2 This is the DSC spectrum of compound 2. From the figure, we can see that the glass transition temperature of compound 2 is 130℃ and the melting point is 249℃. The sublimation temperature of this material is 290℃ and the evaporation temperature is 305℃. This material is a molten material and is completely melted at the evaporation temperature. Therefore, it will not cause material blockage problems during the evaporation process. Because of its low sublimation temperature, this material has excellent processability.

[0246] Figure 3 This is the DSC spectrum of compound 292. From the figure, we can see that the glass transition temperature of compound 292 is 140℃, the melting point is 266℃, the sublimation temperature of this material is 301℃, the evaporation temperature is 320℃, and the evaporation phase is molten. The material is completely melted at the evaporation temperature, so it will not cause material blockage problems during the evaporation process. Due to its low sublimation temperature, the material has excellent processability.

[0247] Figure 4 This is the DSC spectrum of compound 336. From the figure, we can see that the glass transition temperature of compound 336 is 133°C, there is no melting point peak in the spectrum, the sublimation temperature is 295°C, the evaporation temperature is 341°C, and the evaporation phase is a molten material. In the evaporation state, the material is in a completely melted state, so it will not cause material blockage problems during the evaporation process. Because of its low sublimation temperature, the material has excellent process processing performance.

[0248] Figure 5 This is the DSC spectrum of compound 78. From the figure, we can see that the glass transition temperature of compound 78 is 126°C, there is no melting point peak in the spectrum, the sublimation temperature is 310°C, the evaporation temperature is 354°C, and the evaporation phase is a molten material. In the evaporation state, the material is in a completely melted state, so there will be no clogging problem during the evaporation process. Due to the low sublimation temperature, the material has excellent processability.

[0249] The following describes in detail the application effect of the OLED material synthesized by the present invention in the device through device embodiments 1-65 and device comparison examples 1-4. The device manufacturing process of device embodiments 2-65, device comparison example 1, device comparison example 2, device comparison example 3, and device comparison example 4 of the present invention are exactly the same as that of device embodiment 1, and the same substrate material and electrode material are used. The film thickness of the electrode material is also the same. The difference is that the electron blocking layer material in the device is replaced. The structural composition of the device obtained in each embodiment is shown in Table 3, and the performance test results of the device obtained in each embodiment are shown in Table 4.

[0250] Device Example 1

[0251] Substrate layer 1 / ITO anode layer 2 / hole injection layer 3 (HT-1: P1, 3% 10nm) / hole transport layer 4 (HT-1, thickness 120nm) / electron blocking layer 5 (compound 1, thickness 10nm) / light-emitting layer 6 (BH-1 and BD-1 are mixed in a weight ratio of 97:3, thickness 20nm) / hole blocking / electron transport layer 7 (ET-1 and Liq, mixed in a weight ratio of 1:1, thickness 30nm) / electron injection layer 8 (LiF, thickness 1nm) / cathode layer 9 (Mg and Ag, mixed in a weight ratio of 1:9, thickness 16nm) / light extraction layer 10 (compound CP-1, thickness 70nm).

[0252] The specific preparation process is as follows:

[0253] like Figure 1 As shown, the substrate layer 1 washes the ITO anode layer 2 (film thickness is 10nm), that is, alkali washing, pure water washing, drying, and then ultraviolet-ozone washing are performed in sequence to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1:P1 with a film thickness of 10nm, and the P1 doping ratio is 3% as a hole injection layer 3. Then, the compound HT-1 with a thickness of 120nm is evaporated as the hole transport layer 4. Subsequently, the compound 1 with a thickness of 10nm is evaporated as the electron blocking layer 5. After the evaporation of the above-mentioned electron blocking layer 5 material is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared, and its structure includes BH-1 used as the main material of the OLED light-emitting layer 6, BD-1 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, the electron transport layer material is vacuum evaporated as ET-1 and Liq. The vacuum-deposited film thickness of this material is 30nm, and this layer is the hole blocking / electron transport layer 7. On the hole blocking / electron transport layer 7, a lithium fluoride (LiF) layer with a film thickness of 1nm is made by a vacuum evaporation device, and this layer is the electron injection layer 8. On the electron injection layer 8, a Mg:Ag electrode layer with a film thickness of 16nm is made by a vacuum evaporation device, and this layer is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 is vacuum-deposited as the light extraction layer 10.

[0254] Device Example 2-64: The process of Device Example 1 is followed, except that the material of the electron blocking layer 5 is replaced. The specific device structure is shown in Table 3, and the device performance test is shown in Table 4;

[0255] Device Comparative Example 1 was carried out according to the process of Device Example 1, except that the material of the electron blocking layer 5 was EB-1;

[0256] Device Comparative Example 2 is carried out according to the process of Device Example 1, except that the material of the electron blocking layer 5 is D1;

[0257] Device Comparative Example 3 is carried out according to the process of Device Example 1, except that the material of the electron blocking layer 5 is D2;

[0258] Device Comparative Example 4 is carried out according to the process of Device Example 1, except that the material of the electron blocking layer 5 is D3; the specific device structure is shown in Table 3, and the device performance test is shown in Table 4;

[0259] The structural formulas of the materials involved in the above preparation process are as follows:

[0260]

[0261] Table 3

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] The test data of the obtained electroluminescent device are shown in Table 4.

[0268] Table 4

[0269]

[0270]

[0271] Note: The life test system is the EAS-62C OLED device life tester from Japan System Research Co., Ltd. The LT95 life is defined as the time it takes for the brightness of the organic electroluminescent device to decay to 95% of its initial brightness.

[0272] The voltage, current efficiency and color coordinates were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.) to evaluate the driving voltage, current efficiency and color of the organic electroluminescent devices prepared in Examples 1-65 and Comparative Examples 1-4. The current density during measurement was 10 mA / cm 2 .

[0273] It can be seen from the results in Table 4 that the compound with triarylamine as the core prepared in the present invention can be applied to the manufacture of OLED light-emitting devices, and compared with the device comparison example, the life span is increased by more than 14%.

[0274] In summary, the above are only 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 in the protection scope of the present invention.

Claims

1. An organic compound with triarylamine as the core, characterized in that: The structure of the organic compound is shown in the general formula (1): A is phenyl or naphthyl, B is naphthyl, and the connection between A and B and the general formula (1) is a monosubstituted form; The R2 and R3 are independently represented by a hydrogen atom, a phenyl group or a structure represented by the general formula (4), and only one of R2 and R3 is represented by the structure represented by the general formula (4); R0 and R1 are independently represented by a hydrogen atom or a phenyl group, R4 is represented by a hydrogen atom, and at least two of R0, R1, R2, R3, and R4 are not represented by hydrogen atoms; The m, n, p, and q are independently represented by the number 1; Said R5 and R6 are independently represented by hydrogen atoms; The R7 is a hydrogen atom.

2. The organic compound according to claim 1, characterized in that The structure of the organic compound is shown in the general formula (1-1): In the general formula (1-1), the * represents a connection site; A is phenyl or naphthyl, B is naphthyl, and the connection between A and B and the general formula (1-1) is a monosubstituted form; The R3 is a hydrogen atom, a phenyl group or a structure represented by the general formula (4); R2 is a hydrogen atom, a phenyl group or a structure represented by the general formula (4); And one and only one of R2 and R3 is represented by the structure shown in general formula (4); R0 and R1 are independently represented by a hydrogen atom or a phenyl group, R4 is represented by a hydrogen atom, and at least two of R0, R1, R2, R3, and R4 are not represented by hydrogen atoms; The m, n, p, and q are independently represented by the number 1; Said R5 and R6 are independently represented by hydrogen atoms; The R7 is a hydrogen atom.

3. The organic compound according to claim 2, characterized in that In the general formula (1-1), A is a phenyl group or a naphthyl group, and the connection between A and the general formula (1-1) is a monosubstituted form; The B is a naphthyl group, and the connection between B and the general formula (1-1) is in the form of monosubstitution; The R3 is represented by the structure shown in the general formula (4); The R2 is a hydrogen atom or a phenyl group; R0 and R1 are independently represented by a hydrogen atom or a phenyl group, R4 is represented by a hydrogen atom, and at least one of R0, R1, R2, and R4 is not represented by a hydrogen atom; The m and n are independently represented by the number 1; The p and q are independently represented by the number 1; Said R5 and R6 are independently represented by hydrogen atoms; The R7 is a hydrogen atom.

4. The organic compound according to claim 3, characterized in that Said R1 and R4 are independently represented by hydrogen atoms; The R2 is a hydrogen atom or a phenyl group; The R0 represents a hydrogen atom or a phenyl group; And only one of R0 and R2 is phenyl.

5. The organic compound according to claim 2, characterized in that In the general formula (1-1), A is a phenyl group or a naphthyl group, and the connection between A and the general formula (1-1) is a monosubstituted form; The B is a naphthyl group, and the connection between B and the general formula (1-1) is in the form of monosubstitution; The R3 is a hydrogen atom or a phenyl group; The R2 is represented by the structure shown in the general formula (4); R0 and R1 are independently represented by a hydrogen atom or a phenyl group, R4 is represented by a hydrogen atom, and at least one of R0, R1, R3, and R4 is not represented by a hydrogen atom; The m and n are independently represented by the number 1; The p and q are independently represented by the number 1; Said R5 and R6 are independently represented by hydrogen atoms; The R7 is a hydrogen atom.

6. The organic compound according to claim 5, characterized in that Said R3 and R4 are independently represented by hydrogen atoms; The R0 and R1 are independently represented by a hydrogen atom or a phenyl group, and only one of R0 and R1 is represented by a phenyl group.

7. The organic compound according to claim 5, characterized in that The structure of the organic compound is shown in the general formula (D-1): In the general formula (D-1), the * represents a connection site; A is phenyl or naphthyl, and the connection between A and the general formula (D-1) is in the form of monosubstitution; The B is a naphthyl group, and the connection between B and the general formula (D-1) is a monosubstituted form; The m and n are independently represented by the number 1; Said R5 and R6 are independently represented by hydrogen atoms; The R0 and R1 are independently represented by a hydrogen atom or a phenyl group, and only one of R0 and R1 is represented by a phenyl group.

8. The organic compound according to claim 1, characterized in that The specific structure of the compound is: One of them.

9. An organic electroluminescent device, comprising a cathode, an anode and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode, characterized in that: The organic functional layer contains the organic compound with triarylamine as the core as claimed in any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, wherein the organic functional layer comprises an electron blocking layer, characterized in that: The electron blocking layer contains the organic compound with triarylamine as the core as claimed in any one of claims 1 to 8.

Images