Search

CN-122010995-A - Organic compound containing boron and nitrogen and organic electroluminescent device

CN122010995ACN 122010995 ACN122010995 ACN 122010995ACN-122010995-A

Abstract

The application belongs to the field of organic electroluminescence, and in particular relates to an organic compound containing boron and nitrogen and an organic electroluminescent device. The application provides a boron-nitrogen-containing organic compound which comprises a specific nitrogen-containing heterocyclic parent nucleus, wherein at least one boron-nitrogen-containing condensed ring group is introduced into an R 1 -R 3 substituent of the parent nucleus. Through the structural design, the synergistic effect is realized by utilizing the hole transmission characteristic of the nitrogen-containing heterocycle and the electron transmission and luminescence regulation characteristic of the boron-nitrogen-containing condensed ring group, so that the defects of the existing material in the aspects of carrier balance, luminescence efficiency, thermal stability and the like are overcome, the preparation of an OLED device with high efficiency, long service life and low driving voltage is finally realized, and a key material support is provided for the industrialized development of OLED technology in the fields of high-end display and intelligent illumination.

Inventors

  • HUANG HONG
  • JIA TAO
  • HUA TAO
  • ZHANG YOUMING

Assignees

  • 深圳信息职业技术大学
  • 深圳市黑金工业制造有限公司

Dates

Publication Date
20260512
Application Date
20260126

Claims (10)

  1. 1. An organic compound containing boron and nitrogen, characterized by having a structure represented by the general formula (I): (I) Wherein: Z is selected from CR 4 R 5 or c=o; R 4 、R 5 is independently selected from substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aromatic group with 6-20 carbon atoms, or substituted or unsubstituted heteroaromatic group with 5-20 ring atoms, R 4 、R 5 are mutually cyclic or acyclic; R 1 、R 2 、R 3 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 5-20 ring atoms, or formula (A), and at least one of R 1 、R 2 、R 3 is selected from formula (A); (A) Ar 1 、Ar 2 、Ar 3 、Ar 4 is independently selected from a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms; 、 is independently selected from the group consisting of no, single bond, Or (b) ; * Represents a ligation site; The substituted or unsubstituted means that the defined group is unsubstituted or substituted with one or more substituents R * , the R * , for each occurrence, is independently selected from one or a combination of at least two of deuterium, halogen, cyano, alkyl having 1 to 20 carbon atoms, aromatic having 6 to 20 carbon atoms, heteroaromatic having 5 to 20 ring atoms.
  2. 2. The boron-nitrogen-containing organic compound according to claim 1, wherein said general formula (I) is selected from the group consisting of Or (b) And R 4 、R 5 is independently selected from alkyl with 1-10 carbon atoms, substituted or unsubstituted aromatic group with 6-10 carbon atoms, or substituted or unsubstituted heteroaromatic group with 5-10 ring atoms, wherein R 4 、R 5 are mutually cyclic or acyclic.
  3. 3. The boron-nitrogen-containing organic compound according to claim 2, wherein said R 4 、R 5 are mutually cyclic and said Selected from the group consisting of Wherein n is selected from 0, 1, 2,3 or 4 and R a is independently selected from one or a combination of at least two of deuterium, halogen, cyano, alkyl having 1 to 6 carbon atoms, aromatic group having 6 to 10 carbon atoms, heteroaromatic group having 5 to 10 ring atoms for each occurrence.
  4. 4. The boron-nitrogen-containing organic compound according to claim 2, wherein said Selected from the following groups: 。
  5. 5. The boron-nitrogen-containing organic compound according to claim 1, wherein the boron-nitrogen-containing organic compound is selected from any one of the structures of the general formulae (II-1) to (II-6): 。
  6. 6. The boron-nitrogen-containing organic compound of claim 5, wherein R 1 in said general formula (II-2), (II-3), (II-5), (II-6) is independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms substituted or unsubstituted with one or more R b , a heteroaromatic group having 5 to 20 ring atoms substituted or unsubstituted with one or more R b ; R 2 in the general formula (II-1), (II-3), (II-4), (II-6) is independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1-20 carbon atoms, an aryl group having 6-20 carbon atoms substituted or unsubstituted with one or more R b , a heteroaryl group having 5-20 ring atoms substituted or unsubstituted with one or more R b ; R 3 in the general formula (II-1), (II-2), (II-4), (II-5) is independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1-20 carbon atoms, an aryl group having 6-20 carbon atoms substituted or unsubstituted with one or more R b , a heteroaryl group having 5-20 ring atoms substituted or unsubstituted with one or more R b ; Each occurrence of R b is independently selected from one or a combination of at least two of deuterium, halogen, cyano, alkyl having 1-6 carbon atoms, aromatic having 6-20 carbon atoms, heteroaromatic having 5-20 ring atoms.
  7. 7. The boron-nitrogen-containing organic compound of claim 5, wherein Ar 1 、Ar 2 、Ar 3 、Ar 4 is independently selected from an aromatic group having 6 to 20 carbon atoms substituted or unsubstituted with one or more R c , or a heteroaromatic group having 5 to 20 ring atoms substituted or unsubstituted with one or more R c ; Each occurrence of R c is independently selected from one or a combination of at least two of deuterium, halogen, cyano, alkyl having 1-6 carbon atoms, aromatic having 6-20 carbon atoms, heteroaromatic having 5-20 ring atoms; preferably, the structural formula (a) is selected from any one of the following structures: ; Wherein: Z is independently selected from O, S or Se for each occurrence; m1 is selected from 0,1, 2, 3 or 4, m2 is selected from 0,1, 2, 3, 4 or 5, and m3 is selected from 0,1, 2 or 3.
  8. 8. The boron-nitrogen-containing organic compound of claim 1, wherein said boron-nitrogen-containing organic compound is selected from any one of the following structures: 。
  9. 9. A mixture comprising the boron-nitrogen containing organic compound according to any one of claims 1 to 8, and further comprising at least another organic functional material selected from the group consisting of a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting guest material, and a light emitting host material.
  10. 10. An organic electroluminescent device comprising an anode, a cathode and at least one organic functional layer between the anode and the cathode, the at least one organic functional layer comprising the boron-nitrogen containing organic compound of any one of claims 1 to 8 or the mixture of claim 9; preferably, the organic electroluminescent device comprises a substrate, and an anode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode layer sequentially laminated on the substrate, wherein the light emitting layer comprises the organic compound containing boron and nitrogen according to any one of claims 1 to 8 or the mixture according to claim 9.

Description

Organic compound containing boron and nitrogen and organic electroluminescent device Technical Field The application belongs to the field of organic electroluminescence, and in particular relates to an organic compound containing boron and nitrogen and an organic electroluminescent device. Background The Organic Light Emitting Diode (OLED) technology has become a core technology in the field of flat panel display and new generation illumination by virtue of the remarkable advantages of self-luminescence, high contrast, wide viewing angle, low power consumption, flexible preparation and the like, and is widely applied to terminal products such as smart phones, smart televisions, wearable devices and the like. The performance of the OLED device is highly dependent on the molecular structures of organic functional materials, especially the luminescent layer (main body and doped material) and the carrier transmission layer material, which directly determine the key indexes of the device such as luminous efficiency, service life, color purity, driving voltage and the like, so the research and development of the novel high-efficiency OLED material is always the core focus of industry competition. However, there are still a number of technical bottlenecks with existing OLED materials. In terms of luminous performance, the blue light OLED material has the common problem of 'efficiency roll off' of rapid efficiency decay under high brightness due to high difficulty in molecular energy level regulation, the service life of the device is far lower than that of red and green light materials, and in terms of carrier transmission, most main materials (such as carbazole and triarylamine) have strong hole transmission capability but insufficient electron transmission, so that a carrier composite region deviates from the center of a luminous layer, thereby reducing luminous efficiency and increasing driving voltage. In order to solve the problems, researchers respectively research a nitrogen-containing heterocycle (such as indolocarbazole derivatives) and a boron-containing organic material, wherein the nitrogen-containing heterocycle material has a rigid plane structure, high carrier mobility and a tunable energy level structure, but is difficult to realize balanced hole and electron transmission at the same time, and the boron-containing material can enhance the electron transmission capability and realize high-efficiency luminescence (especially blue light emission) and has the defects of insufficient thermal stability and insufficient hole transmission capability. At present, the design of molecular integration of a nitrogen-containing heterocyclic parent nucleus and a boron-containing aryl substituent is still limited, and the synergistic advantages of the nitrogen-containing heterocyclic parent nucleus and the boron-containing aryl substituent are not fully exerted. Disclosure of Invention Aiming at the defects of the prior art, the application aims to provide a boron-nitrogen-containing organic compound and an organic electroluminescent device, and aims to solve the technical problems that the design of molecular integration of a nitrogen-containing heterocyclic parent nucleus and a boron-containing aryl substituent group by an OLED material in the prior art is still limited, and defects still exist in the aspects of carrier balance, luminous efficiency, thermal stability and the like. In order to achieve the above object, in a first aspect, the present application provides a boron-nitrogen-containing organic compound having a structure as shown in general formula (I): (I) Wherein: Z is selected from CR 4R5 or c=o; R 4、R5 is independently selected from substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted aryl with 6-20 carbon atoms, or substituted or unsubstituted heteroaryl with 5-20 ring atoms, R 4、R5 are mutually cyclic or acyclic; R 1、R2、R3 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted aromatic group having 6-20 carbon atoms, substituted or unsubstituted heteroaromatic group having 5-20 ring atoms, or structural formula (A), and at least one of R 1、R2、R3 is selected from structural formula (A); (A) ar 1、Ar2、Ar3、Ar4 is independently selected from a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms; 、 Each independently selected from the group consisting of no, single bond, Or (b); * Represents a ligation site; The term "substituted or unsubstituted" means that the defined group is unsubstituted or substituted with one or more substituents R *, each occurrence of which R * is independently selected from one or a combination of at least two of deuterium, halogen, cyano, alkyl having 1 to 20 carbon atoms, aromatic having 6 to 20 carbon atoms, heteroaromatic having 5 to 2