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CN-122010999-A - Boron-nitrogen compound and organic electroluminescent device comprising same

CN122010999ACN 122010999 ACN122010999 ACN 122010999ACN-122010999-A

Abstract

The invention relates to the technical field of organic photoelectric material preparation, in particular to a boron-nitrogen compound and an organic electroluminescent device containing the same. The boron nitrogen compound has good electron and hole receiving capability, and can effectively inhibit interaction between luminescent molecules by introducing spiro groups. The boron-nitrogen compound is used as a functional layer, and particularly the current efficiency of the organic electroluminescent device manufactured by the boron-nitrogen compound as a luminescent layer is improved, and the efficiency and the service life of the device are greatly improved. It is explained that after most of electrons and holes are recombined, energy is effectively transferred to the boron nitride compound, thereby achieving higher luminous efficiency.

Inventors

  • ZHANG LEI
  • ZHU XU
  • RAO MINYU
  • ZHAO XIAOYU

Assignees

  • 宇瑞(上海)化学有限公司

Dates

Publication Date
20260512
Application Date
20260413

Claims (12)

  1. 1. A boron nitride compound, characterized in that the boron nitride compound has a general structure represented by the following formula I: ; In the formula I, the ring A is selected from one or more Rn substituted or unsubstituted C5-C30 cycloalkyl groups, rn is independently represented by one or more of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C24 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy, C6-C10 aryloxy, arylamino, C6-C30 aryl and C5-C30 heteroaryl groups, the Rn is singly connected or connected in parallel, and Rn can be replaced by deuterium, C1-C10 alkyl and C6-C30 aryl again; R 1 -R 5 is mono-substituted or poly-substituted, each R 1 -R 5 is independently selected from one or more of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, when substituted, each of the substituents is independently selected from deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, and adjacent groups may be linked to form a ring.
  2. 2. The boron nitride according to claim 1, wherein the ring a is selected from the following structures: ; Ra, rb are mono-or poly-substituted, each occurrence of Ra, rb being independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, t-butyl substituted or unsubstituted phenyl, t-butyl substituted or unsubstituted biphenyl.
  3. 3. The boronitride of claim 1, wherein R 1 -R 5 is mono-, di-, or maximum substituted, R 1 -R 5 is each independently selected from one or more of hydrogen, deuterium, F, methyl, ethyl, propyl, t-butyl, pentyl, cyclohexenyl, cyclopentyl, adamantyl, phenyl, methylphenyl, t-butylphenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridinyl, quinolinyl, phenoxy, thiophenyl, furanyl, thiophenyl, benzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, t-butyl substituted carbazolyl, 9-dimethylfluorenyl, diphenylamino.
  4. 4. The boron nitride according to claim 1, wherein the boron nitride has a general structure represented by the following formula I-1: ; In the formula I-1, R 1 、R 2 、R 5 and a ring A are defined as in claim 1, R 6 、R 7 is mono-substituted, di-substituted or tri-substituted, R 6 、R 7 is selected from one or more of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C5-C30 heteroaryl groups, when substituted, each substituent is independently selected from one or more of deuterium, C1-C10 alkyl groups and C6-C18 aryl groups, and adjacent substituents can be connected to form a ring.
  5. 5. The boron nitride according to claim 1, wherein R 3 and R 4 in the boron nitride are linked to form a ring having a general structure represented by formula I-2: ; In the formula I-2, R 1 、R 2 、R 5 and a ring A are defined as in the formula I, R 8 is independently selected from one or more of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C5-C30 heteroaryl in each occurrence, when substituted, each of the substituents is independently selected from one or more of deuterium and C1-C10 alkyl, and n is selected from 1, 2,3 and 4;R 5 and adjacent R 8 can be selectively connected to form a ring.
  6. 6. The boron nitride according to claim 1, wherein the boron nitride is selected from any one of the following chemical structures, wherein "D" represents deuterium: 。
  7. 7. use of a boron nitride compound according to any one of claims 1 to 6 for the preparation of an organic optoelectronic device or an organic electroluminescent device.
  8. 8. An organic electroluminescent device, comprising a cathode, an anode and an organic functional layer therebetween, wherein the organic functional layer comprises a light-emitting layer comprising the boron-nitrogen compound according to any one of claims 1 to 6.
  9. 9. An organic photoelectric device comprising a first electrode, a second electrode facing the first electrode, and a luminescent material layer disposed between the first electrode and the second electrode, wherein the luminescent material layer comprises the boron-nitrogen compound according to any one of claims 1 to 6.
  10. 10. A composition comprising a boron nitrogen compound according to any one of claims 1 to 6.
  11. 11. A formulation comprising a boron nitrogen compound according to any one of claims 1 to 6 and at least one solvent.
  12. 12. A display or lighting device, characterized in that the device comprises one or more of the organic electroluminescent device of claim 8 and/or the organic optoelectronic device of claim 9.

Description

Boron-nitrogen compound and organic electroluminescent device comprising same Technical Field The invention relates to the technical field of organic photoelectric material preparation, in particular to a boron-nitrogen compound and an organic electroluminescent device containing the same. Background With the development of multimedia technology and the improvement of informatization requirements, the requirements on the performance of panel displays are higher and higher. The OLED has a series of advantages of autonomous luminescence, low-voltage direct current drive, full solidification, wide viewing angle, rich colors and the like, and is widely paid attention to potential application in a new-generation display and illumination technology, so that the OLED has a very wide application prospect. The organic electroluminescent device is a spontaneous luminescent device, and the mechanism of OLED luminescence is that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and decay in an organic material under the action of an external electric field to generate luminescence. Typical structures of OLEDs include one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer. Although research on organic electroluminescence is rapidly progressed, there are still many problems to be solved, for example, a green light material having high efficiency and long lifetime and narrow emission has been a problem to be solved by those skilled in the art. Disclosure of Invention In view of the shortcomings in the prior art, the invention aims to provide a boron-nitrogen compound and an organic electroluminescent device comprising the same. The invention effectively inhibits the interaction between luminescent molecules by introducing the spiro large steric hindrance group. Meanwhile, the electron and hole receiving capability of the boron-nitrogen compound is optimized by introducing a rigid spiro structure, so that the energy transmission performance between a host and a guest can be improved, the concentration of high-energy excitons in a light-emitting layer is reduced, and a green light material with high efficiency, long service life and narrow emission is realized. In order to achieve the purpose of the invention, the technical scheme of the invention is as follows: according to one or more embodiments, the present invention provides a boron nitride compound having a general structure represented by the following formula I; ; In the formula I, the ring A is selected from one or more Rn substituted or unsubstituted C5-C30 cycloalkyl groups, rn is independently represented by one or more of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C24 cycloalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy, C6-C10 aryloxy, arylamino, C6-C30 aryl and C5-C30 heteroaryl groups, the Rn is singly connected or connected in parallel, and Rn can be replaced by deuterium, C1-C10 alkyl and C6-C30 aryl again; R 1-R5 is mono-substituted or poly-substituted, each R 1-R5 is independently selected from one or more of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, when substituted, each of the substituents is independently selected from deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, and adjacent groups may be linked to form a ring. Preferably, the ring a is selected from the following structures: ; Ra, rb are mono-or poly-substituted, each occurrence of Ra, rb being independently selected from one or more of hydrogen, deuterium, methyl, ethyl, propyl, t-butyl substituted or unsubstituted phenyl, t-butyl substituted or unsubstituted biphenyl. Preferably, R 1-R5 is mono-, di-or maximum number of substitutions, R 1-R5 is each independently selected from one or more of hydrogen, deuterium, F, methyl, ethyl, propyl, tert-butyl, pentyl, cyclohexenyl, cyclopentyl, adamantyl, phenyl, methylphenyl, tert-butylphenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridinyl, quinolinyl, phenoxy, thiophenyl, furanyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, tert-butyl substituted carbazolyl, 9-dimethylfluorenyl, diphenylamino. Preferably, the boron nitrogen compound has a general structure shown in the following formula I-1: ; In the formula I-1, R 1、R2、R5 and a ring A are defined as in the formula I, R 6、R7 is mono-substituted, di-substituted or tri-substituted, R 6、R7 is selected from one or more of hydrogen, deuterium, halogen atoms, cyano groups, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups and substi