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CN-122011000-A - Boron-nitrogen compound, organic electroluminescent device containing boron-nitrogen compound and application of boron-nitrogen compound

CN122011000ACN 122011000 ACN122011000 ACN 122011000ACN-122011000-A

Abstract

The invention relates to the technical field of organic photoelectric material preparation, in particular to a boron-nitrogen compound, an organic electroluminescent device containing the same and application of the organic electroluminescent device. The boron nitrogen compound has good electron and hole receiving capability, and can effectively inhibit close packing among luminous molecules by introducing a large steric-hindrance spiro structure and asymmetric substituent groups on two acridine rings. 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 (10)

  1. 1. A boron nitride compound, characterized in that the boron nitride compound has a general structure represented by 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 2 is selected from substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, when R 1 、R 2 contains substitution, each of the substitutions is independently selected from deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, R 3 -R 6 is mono-or poly-substituted, and R 3 -R 6 is independently selected from deuterium, halogen, cyano, C1-C24 alkyl.
  2. 2. The boron nitride compound according to claim 1, wherein R 1 -R 2 is each selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, naphthyl, tetrahydronaphthyl, anthryl, phenanthryl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, spirofluorenyl, and diphenylamino, and wherein when substituted, the substitution is single, double, or maximum number of substitutions, each of which is independently selected from deuterium, F, methyl, ethyl, propyl, t-butyl, phenyl t-butyl, and adamantyl.
  3. 3. The boron nitride compound according to claim 1, wherein ring a of formula I 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.
  4. 4. 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: 。
  5. 5. use of the boron nitride compound according to any one of claims 1 to 4 for the preparation of an organic electroluminescent device.
  6. 6. 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 4.
  7. 7. 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 4.
  8. 8. A composition comprising a boron nitride compound according to any one of claims 1 to 4.
  9. 9. A formulation comprising the boron nitride compound of any one of claims 1-4 and at least one solvent.
  10. 10. A display or lighting device comprising one or more of the organic electroluminescent device of claim 6 and/or the organic optoelectronic device of claim 7.

Description

Boron-nitrogen compound, organic electroluminescent device containing boron-nitrogen compound and application of boron-nitrogen compound Technical Field The invention relates to the technical field of organic photoelectric material preparation, in particular to a boron-nitrogen compound, an organic electroluminescent device containing the same and application of the organic electroluminescent device. 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 The invention aims at overcoming the defects of the prior art and provides a boron-nitrogen compound and an organic electroluminescent device comprising the same. The invention effectively inhibits the close packing among luminescent molecules by introducing asymmetric substituent groups. 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 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、R2 is selected from substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, when R 1、R2 contains substitution, each of the substitutions is independently selected from deuterium, C1-C24 alkyl, C3-C24 cycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, R 3-R6 is mono-or poly-substituted, and R 3-R6 is independently selected from deuterium, halogen, cyano, C1-C24 alkyl. Preferably, R 1 and R 2 are linked by only one carbon atom, and there is no other way of linking. Preferably, each R 1-R2 is the same or different and is selected from one or more of substituted or unsubstituted phenyl, biphenyl, naphthyl, tetrahydronaphthyl, anthryl, phenanthryl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, spirofluorenyl and diphenylamino, and when substituted, the substitution is single substitution, double substitution or maximum substitution, and each substitution is independently selected from deuterium, F, methyl, ethyl, propyl, tertiary butyl, phenyl tertiary butyl and adamantyl. Preferably, each R 3-R6 is identically selected from methyl, ethyl, isopropyl, tert-butyl. Preferably, ring A in formula I is selected from adamantyl, norbornyl, rn substituted or unsubstituted cyclopentyl, rn substituted or unsubstituted cyclohexenyl, and each Rn is independently selected from one or more of hydrogen, deuterium, F, cyano, C1-C10 alkyl, C3-C12 cycloalkyl, C6-C18 aryl, C5-C18 heteroaryl. More preferably, ring a in formula I 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, p