CN-116554217-B - Condensed heterocyclic compound and organic electroluminescent device thereof

CN116554217BCN 116554217 BCN116554217 BCN 116554217BCN-116554217-B

Abstract

The invention provides a condensed heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. The fused heterocyclic compound provided by the invention has good electron transmission capability, proper HOMO and LUMO energy levels and higher triplet state energy level, can reduce electron transmission potential barrier, improve electron and hole transmission balance, can effectively limit holes in a luminescent layer, and can improve effective recombination probability of excitons, thereby reducing driving voltage, improving luminous efficiency and prolonging service life of a device.

Inventors

GUO JIANHUA
MIAO YUHE
DU MINGZHU

Assignees

长春海谱润斯科技股份有限公司

Dates

Publication Date: 20260505
Application Date: 20230516

Claims (8)

1. A fused heterocyclic compound, wherein the fused heterocyclic compound is selected from the following structures: in formula I, the said' "Any one selected from the following groups: ; Said p 4 is independently selected from 1,2, 3, 4, 5, 6, or 7; r 2 is independently selected from any one of hydrogen, deuterium and tritium; the R 0 is independently selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl and A group, wherein the substituent represented by the substituent in the substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl and substituted or unsubstituted pyridyl is selected from deuterium, tritium and cyano; The X 0 is selected from O, S or N (R 3 ); the R 3 is selected from any one of substituted or unsubstituted C6-C12 aryl, and the substituent represented by the substituent in the substituted or unsubstituted C6-C12 aryl is selected from deuterium and tritium; and L 0 is selected from a single bond or one of the following groups: ; the L 1 、L 2 is independently selected from a single bond or one of the following groups: ; Rx is independently selected from any one of hydrogen, deuterium and tritium; rx' is independently selected from any one of hydrogen, deuterium and tritium; The n 1 is independently selected from 1, 2, 3 or 4, and the n 2 is independently selected from 1, 2 or 3; Ar 1 、Ar 2 is independently selected from any one of the following groups: ; The a 1 is independently selected from 1,2, 3,4 or 5, the a 2 is independently selected from 1,2, 3 or 4, the a 3 is independently selected from 1,2 or 3, the a 4 is independently selected from 1 or 2, the a 5 is independently selected from 1,2, 3,4,5, 6 or 7, the a 9 is independently selected from 1,2, 3,4,5 or 6, and the a 10 is independently selected from 1,2, 3,4,5, 6, 7 or 8; R 4 is independently selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; r 7a is independently selected from any one of hydrogen, deuterium and A groups; r 7b is independently selected from any one of hydrogen, deuterium and phenyl; R 7 is independently selected from any one of hydrogen and deuterium; R 10 ' is any one selected from phenyl, biphenyl and naphthyl; R 10 is independently selected from any one of hydrogen, deuterium, tritium, methyl and deuterated methyl; R 1 is independently selected from any one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl; said m is selected from 1, 2 or 3; Provided that one or two a groups are contained in the structure of formula I, and R 0 is selected from a groups, or one of the R 7a of Ar 1 is selected from a groups and 0 or one of the R 7a of Ar 2 is selected from a groups, or one of the R 7a of Ar 2 is selected from a groups and 0 or one of the R 7a of Ar 1 is selected from a groups; said A is represented by the group of formula II: Ra, rb, rc in formula II are independently selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, unsubstituted or substituted by deuterium; The L 3 is selected from any one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene and substituted or unsubstituted pyridyl, and L 3 in the A group in Ar 1 、Ar 2 is selected from single bond, and the substituent represented by the substituent in the substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene and substituted or unsubstituted pyridyl is selected from deuterium and tritium.
2. The fused heterocyclic compound according to claim 1, wherein the group represented by formula II is selected from any one of the following groups: 。
3. the fused heterocyclic compound according to claim 1, wherein Ar 1 、Ar 2 is independently selected from any one of the following groups: 。
4. The fused heterocyclic compound according to claim 1, wherein L 0 is selected from a single bond or at least one of the following groups: 。
5. the fused heterocyclic compound according to claim 1, wherein the fused heterocyclic compound is selected from any one of the following structures: 。
6. An organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of the condensed heterocyclic compounds according to any one of claims 1 to 5.
7. An organic electroluminescent device as claimed in claim 6, wherein the organic layer comprises a light-emitting layer comprising a host material comprising at least one of the fused heterocyclic compounds as claimed in any one of claims 1 to 5.
8. An organic electroluminescent device according to claim 6, wherein the organic layer comprises at least one of an electron transport layer or a hole blocking layer, the at least one of an electron transport layer or a hole blocking layer comprising at least one of the condensed heterocyclic compounds according to any one of claims 1 to 5.

Description

Condensed heterocyclic compound and organic electroluminescent device thereof Technical Field The invention relates to the technical field of organic electroluminescent materials, in particular to a condensed heterocyclic compound and an organic electroluminescent device thereof. Background OLED (Organic LIGHT EMITTING Diode) is a luminescent device using Organic solid semiconductor as luminescent material, has the advantages of full solid state, high luminous efficiency, high color contrast, quick response speed, no viewing angle limitation, ultra-thin, low power consumption, easy realization of flexible display and 3D display, and the like, and is a novel display technology with wide development prospect. The light-emitting principle of the organic electroluminescent device is mainly that holes and electrons are respectively injected into an organic layer from a cathode and an anode under the action of an external electric field, enter a light-emitting layer through a hole transmission area and an electron transmission area respectively, then the holes and the electrons are combined in the light-emitting layer to generate excitons, and the excitons are subjected to radiation attenuation to emit light. At present, the device structure of an OLED is often in a sandwich shape, and includes a cathode, an anode, and an organic layer disposed therebetween, where the organic layer is also divided into a hole transport region, an electron transport region, and a light emitting layer according to different functions of the organic layer. The electron transport region can be divided into an electron injection layer, an electron transport layer and a hole blocking layer, and the light-emitting layer is divided into a host material and a guest material by adopting a host-guest doping mode. With the continuous development of organic electroluminescent devices, organic electroluminescent materials therein have become a research hotspot in the field. At present, the electron transport region material and the luminescent layer material still have some problems, the electron transport region material mainly shows low electron transport efficiency, unbalanced electron and hole transport, and can not be effectively transported to the luminescent layer, and the energy level is not matched, so that a part of electrons and holes escape to the outside of the luminescent layer, and the luminescent efficiency of the organic electroluminescent device is reduced, and the driving voltage is improved. The light-emitting layer also has the problems of unbalanced migration of electrons and holes, mismatching of triplet energy levels of host and guest materials, and the like, so that the efficiency of forming excitons by combining electrons and holes is low, and the light-emitting efficiency of the organic electroluminescent device is further affected. Optimization and performance enhancement of OLED devices can be further achieved by improving the materials of the different functional layers in the device. Accordingly, in order to solve the problems of the current electron transport region materials and light emitting layer materials, there is a need to develop an electron transport material, a hole blocking material, and a light emitting layer host material having more excellent properties. Disclosure of Invention Aiming at the problems in the prior art, the invention provides a condensed heterocyclic compound and an organic electroluminescent device thereof, which can solve the problems of high driving voltage, low luminous efficiency and short service life of the organic electroluminescent device in the prior art. Specifically, the invention provides a condensed heterocyclic compound which is selected from structures represented by a formula I: In formula I, said E is selected from any one of the following groups: the "x" sites are parallel ring sites; the X is independently selected from C (R 2) or N atoms; R 0、R2 is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; The X 0 is selected from O, S or N (R 3); R 3 is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; l 0、L1、L2 is independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C2-C30 heteroarylene; Ar 1、Ar2 is independently selected from any one of substituted or unsubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C2-C30, fused ring groups of substituted or unsubst