CN113666913A - Organic compound and application thereof in organic light-emitting field - Google Patents

Organic compound and application thereof in organic light-emitting field Download PDF

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CN113666913A
CN113666913A CN202010406714.8A CN202010406714A CN113666913A CN 113666913 A CN113666913 A CN 113666913A CN 202010406714 A CN202010406714 A CN 202010406714A CN 113666913 A CN113666913 A CN 113666913A
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李之洋
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I. The compounds provided by the invention are carboThe azole group is a main structure, and a large conjugated substituent group is introduced, so that the large conjugated plane structure is beneficial to the transmission of current carriers, and the overall performance of the molecule is effectively improved. When the compound is used as an organic electroluminescent device, particularly as a luminescent layer material, the carrier transmission balance in the device can be effectively improved, so that the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.

Description

Organic compound and application thereof in organic light-emitting field
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
In recent years, Organic Light Emitting Diodes (OLEDs) have been developed very rapidly, and have a place in the field of information display, which is mainly benefited from the fact that OLED devices can prepare full-color display devices using three primary colors of high saturation, red, green and blue, and can realize bright, light, thin and soft colors without additional backlight sources.
The Organic Light Emitting Diode (OLED) device plays an important role in a thin-layer structure containing various organic functional materials, and common organic functional materials comprise a light emitting layer material, an electron blocking layer material, an electron transport layer material, a hole blocking layer material, a hole transport layer material and the like. After the power is switched on, electrons and holes are respectively injected and transmitted to the light-emitting layer and are recombined to generate excitons, so that light is emitted. Therefore, the research on organic functional materials in OLED devices is a key research topic for those skilled in the art.
At present, researchers have developed various organic functional materials for various specific device structures, which play roles in improving carrier mobility, regulating carrier balance, breaking through electroluminescence efficiency, and delaying device attenuation.
Conventional fluorescent emitters emit light primarily using singlet excitons generated upon recombination of holes and electrons, and such emitters are still used in various OLED devices. In addition, a phosphorescent emitter, that is, a material which can emit light by using both triplet excitons and singlet excitons, such as an iridium complex or the like, is also included. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. The thermal excitation sensitization fluorescence (TASF) technology is to adopt TADF material to sensitize the luminophor in an energy transfer mode, so that higher luminous efficiency is realized, and the TADF material has wide application prospect in the OLED field.
Although various organic functional layer materials have been developed, nowadays, the requirements of people on the performance of the OLED device are higher and higher, and the existing organic functional materials cannot be applied to new OLED devices with higher performance.
Therefore, there is a need in the art to develop a wider variety of organic functional materials, which can improve the light emitting efficiency, reduce the driving voltage, and prolong the service life when applied to OLED devices.
Disclosure of Invention
An object of the present invention is to provide a compound capable of improving light emitting efficiency and reducing driving voltage when applied to an OLED device.
In order to achieve the purpose, the invention adopts the following technical scheme:
a compound having the structure shown in formula I;
Figure BDA0002491591490000021
said X1～X22Each independently selected from C, CR1Or N, said R1Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of C, B, C, B, C, B6, B3624, B1Independently with the attached aromatic ring to form a ring or not;
ar is1One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
said L1And L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
The above "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from different substituents.
Further, the compound of the present invention has a structure represented by any one of the following formulae (I-1) to (I-4):
Figure BDA0002491591490000022
Figure BDA0002491591490000031
in formulae (I-1) to (I-4), Ar1、L1、L2、X1～X22Are as defined in formula I.
Preferably, the compound of the present invention has a structure represented by the formula (I-1) or the formula (I-2);
still preferably, the compound of the present invention has the structure represented by the formula (I-2).
Further, the compound of the present invention has a structure represented by the following formula (I-a) or formula (I-b):
Figure BDA0002491591490000032
in the formulae (I-a) and (I-b), Ar1、L1、L2、X1～X22Are as defined in formula I.
Further preferably, in the above formula I, formulae (I-1) to (I-4), formula (I-a) and formula (I-b), said X15-X18Are each independently selected from CR1Said R is1Independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstitutedSubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of1Independently fused with the connected benzene ring to form a ring or not fused to form a ring, and is connected to form a ring through-O-, -S-, -CR8R9-, C ═ C or single bond, and R8And R9Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
Still more preferably, said X15-X18Are each independently selected from CR1Said R is1Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of C, B, C, B, C, B6, B3624, B1Independently not fused with the connected benzene ring to form a ring;
or, more preferably, X15-X18Are each independently selected from CR1Said R is1Independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and the R1Independently fused with the attached benzene ring to form a ring, linked to form a ring via-O-, -S-, -CR8R9-, C ═ C or single bond, and R8And R9Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
Further, the compound of the present invention has a structure represented by any one of the following formulae (I-A-1), (I-A-2), (I-A-3), (I-B-1), (I-B-2), (I-B-3), (I-B-4), (I-B-5), (I-B-6) or (I-D):
Figure BDA0002491591490000041
in the formulae (I-A-1), (I-A-2) and (I-A-3), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and each is independently one selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
Figure BDA0002491591490000051
In the formula (I-B-1), the formula (I-B-2), the formula (I-B-3), the formula (I-B-4), the formula (I-B-5) and the formula (I-B-6), Ar is1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said Y is selected from S or O, said R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Figure BDA0002491591490000052
in the formula (I-D), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1One selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
Still further, the compound of the present invention has a structure represented by any one of the following formulae (I-A-1), (I-A-2), and (I-A-3):
Figure BDA0002491591490000061
in the formulae (I-A-1), (I-A-2) and (I-A-3), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and each is independently selected from one of hydrogen, a substituted or unsubstituted C1 to C10 chain alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C10 silyl group, a substituted or unsubstituted C6 to C30 arylamino group, a substituted or unsubstituted C3 to C30 heteroarylamino group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group;
preferably, the compound has a structure represented by any one of the following formulae (I-A-1-1), (I-A-1-2), (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4):
Figure BDA0002491591490000062
Figure BDA0002491591490000071
formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), wherein Ar is defined in formula (I-A-3-4)1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and is each independently selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a halogen atom, a salt, or a salt thereof, or a salt thereof,One of cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
alternatively, it is preferable that the compound has a structure represented by any one of the following formulae (I-A-1-a), (I-A-1-b), (I-A-2-a), (I-A-2-b), (I-A-3-a), (I-A-3-b):
Figure BDA0002491591490000072
Figure BDA0002491591490000081
in the formula (I-A-1-a), the formula (I-A-1-b), the formula (I-A-2-a), the formula (I-A-2-b), the formula (I-A-3-a), the formula (I-A-3-b), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and each is independently one selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
Further, the compound of the present invention has a structure represented by any one of the following formulae (I-B-1), (I-B-2), (I-B-3), (I-B-4), (I-B-5), and (I-B-6):
Figure BDA0002491591490000082
Figure BDA0002491591490000091
in the formula (I-B-1), the formula (I-B-2), the formula (I-B-3), the formula (I-B-4), the formula (I-B-5) and the formula (I-B-6), Ar is1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said Y is selected from S or O, said R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
preferably, the compound has the following formula (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), A structure represented by any one of formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4):
Figure BDA0002491591490000092
Figure BDA0002491591490000101
Figure BDA0002491591490000111
formula (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), In the formula (I-B-5-1), the formula (I-B-5-2), the formula (I-B-5-3), the formula (I-B-5-4), the formula (I-B-6-1), the formula (I-B-6-2), the formula (I-B-6-3) and the formula (I-B-6-4), Ar is represented by the formula1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said Y is selected from S or O, said R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
alternatively, it is preferable that the compound has a structure represented by any one of the following formulae (I-B-1-a), (I-B-1-B), (I-B-2-a), (I-B-2-B), (I-B-3-a), (I-B-3-B), (I-B-4-a), (I-B-4-B), (I-B-5-a), (I-B-5-B), (I-B-6-a), and (I-B-6-B):
Figure BDA0002491591490000121
Figure BDA0002491591490000131
formula (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4)-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a), formula (I-B-6-B), said Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said Y is selected from S or O, said R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
More preferably, the compound of the present invention has a structure represented by any one of the following formulae (I-C-1), (I-C-2), (I-C-3), (I-C-4), (I-C-5), (I-C-6), (I-C-7), (I-C-8), (I-C-9), (I-C-10), (I-C-11), and (I-C-12):
Figure BDA0002491591490000132
Figure BDA0002491591490000141
Figure BDA0002491591490000151
formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), wherein Ar is Ar1、L1、L2、X1～X14、X19～X22Are uniformly defined in formula I,the R is4、R5、R6And R7Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
Still further preferably, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), Formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), Formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
said X1～X14Are each independently C or CR1Preferably, said R1Are all hydrogen;
said X19～X22Are each independently C or CR1Preferably, said R1Are all hydrogen.
Still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), Formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), Formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
ar is1Selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl; more preferably, Ar is1Selected from nitrogen-containing substituted or unsubstituted C3-C30 electron-deficient heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
The "electron-deficient heteroaryl group (may be referred to as an electron-deficient group)" in the present specification means a group in which the electron cloud density on the benzene ring is decreased after the group substitutes for hydrogen on the benzene ring, and usually such a group has a Hammett value of more than 0.6. The Hammett value is a representation of the charge affinity for a particular group and is a measure of the electron withdrawing group (positive Hammett value) or electron donating group (negative Hammett value). The Hammett equation is described In more detail In Thomas H.Lowry and Kathelen Schueler Richardson, "mechanics and Theory In Organic Chemistry", New York,1987, 143-. Such groups may be listed but are not limited to: triazinyl, pyrimidinyl, benzopyrimidinyl, benzopyridyl, naphthyridinyl, phenanthridinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, and alkyl-or aryl-substituted ones of the foregoing.
Still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-b), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1).-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), In the formula (I-B-5-4), the formula (I-B-6-1), the formula (I-B-6-2), the formula (I-B-6-3), the formula (I-B-6-4), (I-B-1-a), the formula (I-B-1-B), the formula (I-B-2-a), the formula (I-B-2-B), the formula (I-B-3-a), the formula (I-B-3-B), the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B), ar is1Has one of the following structures (3-1) to (3-4):
Figure BDA0002491591490000171
in the formula (3-1), the Z1、Z2、Z3、Z4And Z5Each independently selected from CR10Or an N atom, and Z1、Z2、 Z3、Z4And Z5At least one of which is an N atom,
in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13Each independently selected from CR10Or an N atom, and Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least one of which is an N atom,
in the formula (3-3), the Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23Each independently selected from CR10Or an N atom, and Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23At least one of which is an N atom,
in the formula (3-4), Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33Each independently selected from CR10Or an N atom, and Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33At least one of which is an N atom,
the R is10One selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein represents an access bond to a group;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
Still more preferably, Ar is1Has the structure shown in (3-1) or (3-2).
Still more preferably, in the formula (3-1), Z1、Z2、Z3、Z4And Z5At least two of which are N atoms; in the formula (3-2), Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least two of which are N atoms.
Still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2)Formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), Formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), Formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), Formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), In the formulae (I-B-5-B), (I-B-6-a) and (I-B-6-B), Ar1One selected from the following substituted or unsubstituted groups: pyridyl, quinolyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl.
Still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2) Formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), Formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B), wherein Ar is as defined above1One selected from substituted or unsubstituted A1-A14 groups:
Figure BDA0002491591490000181
Figure BDA0002491591490000191
wherein denotes the access bond of the group.
Still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A)-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), Formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), In the formula (I-B-2-a), the formula (I-B-2-B), the formula (I-B-3-a), the formula (I-B-3-B), the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B), Ar is represented by the formula1One selected from the group consisting of B1-B19:
Figure BDA0002491591490000192
still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), Formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2),Formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), In the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B), L1Selected from single bonds or substituted or unsubstituted groups as follows: one of phenylene, naphthylene and biphenylene;
still further, the above-mentioned formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), Formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), Formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), Formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), In the formula (I-B-6-1), the formula (I-B-6-2), the formula (I-B-6-3), the formula (I-B-6-4), (I-B-1-a), the formula (I-B-1-B), the formula (I-B-2-a), the formula (I-B-2-B), the formula (I-B-3-a), the formula (I-B-3-B), the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B), the L2 is selected from a single bond or the following substituted or unsubstituted groups: one of phenylene, naphthylene and biphenylene.
When the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
The hetero atom in the present invention generally means an atom or a group of atoms selected from N, O, S, P, Si and Se, preferably N, O, S.
The atomic names given in this disclosure, including their respective isotopes, for example, hydrogen (H) includes1H (protium or H),2H (deuterium or D), etc.; carbon (C) then comprises12C、13C and the like.
In the above substituents, the number of carbon atoms of the chain alkyl group having from C1 to C10 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, or the like; the carbon number of the C3-C10 cycloalkyl group can be C4, C5, C6, C7, C8, C9, C10 and the like; the C1-C10 alkoxy group may have C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the C1-C10 thioalkoxy group may have C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.; the C6-C30 monocyclic aryl group may have C6, C12, C14, C16, C18, C20, C26, C28 and the like; the number of carbons of the C10-C30 condensed ring aryl group may be C10, C12, C14, C16, C18, C20, C26, C28, etc.; the C3-C30 monocyclic heteroaryl group may have C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, etc.; the carbon number of the C6-C30 fused ring heteroaryl group may be C6, C10, C12, C14, C16, C18, C20, C26, C28, and the like.
More preferably, the substituent is selected from any one of C6 to C30 monocyclic aryl, C10 to C30 fused ring aryl, C3 to C30 monocyclic heteroaryl, and C6 to C30 fused ring heteroaryl, and specifically, phenyl, naphthyl, biphenyl, pyridyl, pyrimidyl, quinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothienyl, and the like are preferable.
In the present specification, the C3-C10 cycloalkyl group includes monocycloalkyl groups and polycycloalkyl groups.
In the present specification, the chain alkyl group having C1 to C10 is preferably a chain alkyl group having C1 to C6, and examples thereof include: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl and the like.
Further, the compounds described by the general formula of the present invention may preferably be compounds of specific structures shown by the following P1-P121, which are merely representative:
Figure BDA0002491591490000211
Figure BDA0002491591490000221
Figure BDA0002491591490000231
Figure BDA0002491591490000241
Figure BDA0002491591490000251
Figure BDA0002491591490000261
Figure BDA0002491591490000271
Figure BDA0002491591490000281
Figure BDA0002491591490000291
Figure BDA0002491591490000301
Figure BDA0002491591490000311
Figure BDA0002491591490000321
the second object of the present invention is to provide the use of the compound according to the first object for the application in organic electronic devices.
Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper, preferably an organic electroluminescent device.
Preferably, the compound is used as a host material of a light emitting layer in the organic electroluminescent device.
The invention also provides an organic electroluminescent device which comprises a substrate, a first electrode, a second electrode and at least one organic layer positioned between the first electrode and the second electrode, wherein the organic layer contains at least one compound for one purpose.
Preferably, the organic layer includes a light-emitting layer containing at least one compound described for one of the purposes.
Preferably, the compound serves as a host material of the light-emitting layer.
More specifically, the organic electroluminescent device will be described in detail.
The OLED device includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), and aromatic amine derivatives as shown below in HT-1 to HT-51; or any combination thereof.
Figure BDA0002491591490000331
Figure BDA0002491591490000341
Figure BDA0002491591490000351
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
Figure BDA0002491591490000361
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
Figure BDA0002491591490000362
Figure BDA0002491591490000371
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described below; mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77 may also be used, but are not limited thereto.
Figure BDA0002491591490000372
Figure BDA0002491591490000381
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-65 listed below.
Figure BDA0002491591490000391
Figure BDA0002491591490000401
Figure BDA0002491591490000411
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but is not limited to, one or more compounds of ET-1 to ET-65 described above, or one or more compounds of PH-1 to PH-46 described below; mixtures of one or more compounds from ET-1 to ET-65 with one or more compounds from PH-1 to PH-46 may also be used, but are not limited thereto.
Figure BDA0002491591490000412
Figure BDA0002491591490000421
Figure BDA0002491591490000431
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
Liq、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
The cathode is metal, metal mixture or oxide such as magnesium silver mixture, LiF/Al, ITO, etc.
The specific reason why the above-mentioned compound of the present invention is excellent in performance is not clear, and it is presumed that the following reasons may be:
the compound provided by the invention takes carbazole containing a specific substituted 7-membered ring as a parent nucleus structure, and the addition of the 7-membered ring makes up for the defect of hole transmission capability of the carbazole structure, thereby being beneficial to improving the hole mobility of the whole molecule. When the compound is used in an organic electroluminescent device, particularly as a luminescent layer material, the compound is beneficial to realizing the balanced transmission of current carriers in an organic functional layer of the device, so that the electron injection and migration efficiency in the device can be effectively improved, and the excellent effects of high luminescent efficiency and low starting voltage of the device are ensured.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The synthesis of the compounds of formula I of the present invention is represented as follows:
Figure BDA0002491591490000441
the above symbols all have the same meaning as in formula I.
Compounds of synthetic methods not mentioned in the following synthetic examples of the present invention are all commercially available starting products. Solvents and reagents used in the present invention, such as methylene chloride, ethanol, 1, 8-dibromonaphthalene, phenylboronic acid, carbazole, quinazoline, quinoxaline, triazine, and other chemical reagents, are commercially available from the domestic chemical product markets, such as from national drug group reagents, TCI, shanghai Biyao pharmaceuticals, and carbofuran. In addition, they can be synthesized by a known method by those skilled in the art.
Synthesis of intermediate M1-M4:
Figure BDA0002491591490000442
1, 8-dibromonaphthalene (0.1mol, 1eq), phenylboronic acid (0.1mol, 1eq), potassium carbonate (0.2mol, 2eq), tetrakis (triphenylphosphine) palladium (0.001mol, 0.01eq), dioxane (300ml) and water (50ml) were added to a three-necked flask. The oil bath was heated to 90 ℃ for 6 hours and the reaction was monitored by TLC. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. And purifying the obtained crude product by column chromatography to obtain an intermediate M-A.
M-A (0.08mol, 1eq), pinacol o-aminobenzeneboronic acid ester (0.1mol, 1.2eq), potassium carbonate (0.12mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.0008mol, 0.01eq), dioxane (250ml) and water (40ml) were added to a three-necked flask. The oil bath was heated to 110 ℃ for 6 hours and the reaction was monitored by TLC. And cooling the reaction liquid to room temperature, and carrying out reduced pressure rotary evaporation to remove the solvent to obtain a crude product, and carrying out column chromatography purification to obtain an intermediate M-B.
Adding M-B (0.05mol) into 200ml of acetic acid, adding sulfuric acid (0.25mol), cooling to 10 ℃, dropwise adding an aqueous solution (0.1mol) of sodium nitrite, recovering the reaction at room temperature for 4 hours after dropwise adding, detecting by GC-MS to confirm that the reaction is complete, and purifying by column chromatography to obtain the intermediate M.
By replacing only the pinacol ester of orthoaminophenylboronic acid with the equivalent amount of the pinacol ester of chloroorthoaminophenylboronic acid according to the same method as described above, we can easily obtain the following intermediates:
Figure BDA0002491591490000451
synthesis of intermediate M5:
Figure BDA0002491591490000452
adding M (0.05mol) into 200ml of DMF, cooling to 0 ℃, dropwise adding a DMF solution (0.075mol) of NBS, recovering the reaction at room temperature for 4h after dropwise adding, detecting by GC-MS to confirm that the reaction is complete, and purifying by column chromatography to obtain an intermediate M5.
Synthesis of intermediate M6:
Figure BDA0002491591490000453
adding (0.1mol) 2-nitro-1-naphthol into 300ml dichloromethane, adding triethylamine (0.15mol), cooling to 0 ℃, dropwise adding 0.2mol trifluoromethanesulfonic anhydride, reacting at room temperature for 2h after dropwise addition, monitoring by TLC to complete reaction, slowly adding water to separate an organic phase, concentrating to obtain brown oily matter, and heating petroleum ether to obtain a yellow solid after boiling.
M6-A (0.1mol, 1eq), 2'- (pinacolato-2-yl borate) - [1,1' -biphenyl ] -2-amine (0.12mol, 1.2eq), potassium carbonate (0.15mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.001mol, 0.01eq), dioxane (250ml) and water (40ml) were added to a three-necked flask. The oil bath was heated to 110 ℃ for 6 hours and the reaction was monitored by TLC. And cooling the reaction liquid to room temperature, and carrying out reduced pressure rotary evaporation to remove the solvent to obtain a crude product, and carrying out column chromatography purification to obtain an intermediate M6-B.
M6-B (0.05mol, 1eq), sulfuric acid (0.1mol), acetic acid (200ml) were added to a three-necked flask. And (3) cooling to 10 ℃, dropwise adding a sodium nitrite aqueous solution (0.1mol), and after dropwise adding, reacting at room temperature for 2hTLC to monitor that the reaction is finished. Adding water and ethyl acetate for extraction, decompressing and rotary distilling to remove the solvent to obtain a crude product, and carrying out column chromatography purification to obtain an intermediate M6-C.
Adding M6-C (0.04mol, 1eq), iron powder (0.2mol) and ethanol (200ml) into a three-neck flask, heating and refluxing for reaction for 24 hours, directly spin-drying the ethanol after the reaction is completed, washing residues with dichloro, and concentrating an organic phase to obtain brown oily matter.
Adding M6-D (0.04mol), cuprous bromide (0.1mol) and hydrochloric acid (0.1mol) into 200ml of acetonitrile, cooling to 0 ℃, dropwise adding tert-butyl nitrite (0.1mol), reacting at 50 ℃ for 4 hours after dropwise adding, monitoring the reaction completion by GC-MS, and carrying out column chromatography to obtain an intermediate M6.
Synthesis example 1
Synthesis of Compound P1
Figure BDA0002491591490000461
Adding carbazole-3-boric acid (10mmol), M5(10mmol), potassium carbonate (15mmol), palladium tetrakis (triphenyl) phosphine (0.1mmol), 50mL of water and 200mL of dioxane into a reaction bottle, heating to 110 ℃ for reaction for 4h, monitoring the reaction by TLC (thin layer chromatography), cooling, adding water and dichloromethane, separating an organic phase, concentrating, adding ethanol, stirring to separate out a large amount of solid, and filtering to obtain P1-A.
Adding P1-A (5mmol), 2-chloro-4-phenylquinazoline (6mmol), potassium carbonate (10mmol) and 100mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reaction for 6h, monitoring the reaction by TLC, cooling, adding water, filtering, and purifying a filter cake by column chromatography to obtain the compound P1.
Synthesis example 2
Synthesis of Compound P5
The difference from synthesis example 1 is that carbazole-3-boronic acid was replaced with carbazole-4-boronic acid in an equivalent amount to obtain compound P5.
Synthesis example 3:
synthesis of Compound P8
Figure BDA0002491591490000471
Adding carbazole-4-boric acid (10mmol), M5(10mmol), potassium carbonate (15mmol), palladium tetrakis (triphenyl) phosphine (0.1mmol), 50mL of water and 200mL of dioxane into a reaction bottle, heating to 110 ℃ for reaction for 4h, monitoring the reaction by TLC (thin layer chromatography), cooling, adding water and dichloromethane, separating an organic phase, concentrating, adding ethanol, stirring to separate out a large amount of solid, and filtering to obtain P8-A.
Adding P8-A (5mmol), 2- (4-fluorophenyl) -4-phenylquinazoline (6mmol), cesium carbonate (7.5mmol) and 100mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 6h, monitoring the reaction by TLC, cooling, adding water, filtering, and purifying a filter cake column chromatography purified compound P8.
Synthesis example 4:
synthesis of Compound P10
Figure BDA0002491591490000472
M5(0.1mol), pinacol diboron (0.15mol), potassium acetate (0.2mol) and [1,1' -bis (diphenylphosphino) ferrocene]Adding palladium dichloride (0.001mol) and 300mL of dioxane into a reaction bottle, heating to 110 ℃ for reaction for 5h, monitoring the reaction by TLC, cooling, adding water, extracting by dichloromethane, and concentrating an organic phase to obtain P10-A.
Adding P10-A (50mmol), 10-bromo-7H benzocarbazole (50mmol), potassium carbonate (10mmol), tetrakis (triphenyl) phosphine palladium (0.1mmol), 50mL of water and 150mL of dioxane into a reaction bottle, heating to 110 ℃ for reaction for 5 hours, monitoring by TLC to complete reaction, cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain a compound P10-B.
Adding P10-B (30mmol), 2-chloro-3-phenylquinoxaline (50mmol), potassium carbonate (60mmol) and 150mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 6h, monitoring the reaction by TLC, cooling, adding water, filtering, and purifying a filter cake column chromatography to obtain the compound P10.
Synthesis example 5:
synthesis of Compound P18
The difference from Synthesis example 4 was that 10-bromo-7H-benzocarbazole was replaced with equal amounts of 2-bromo-5H-benzocarbazole, yielding Compound P18.
Synthesis example 6:
synthesis of Compound P33
Figure BDA0002491591490000481
Adding P1(10mmol) and 100mL of N, N-dimethylformamide into a reaction bottle, cooling to 0 ℃, dropwise adding a solution of NBS (12mmol) and N, N-dimethylformamide (30mmol), keeping the temperature for reaction for 2 hours after dropwise adding, monitoring the reaction by HPLC, cooling, adding water, filtering and drying to obtain P33-A.
Adding P33-A (6mmol), diphenylamine (8mmol), sodium tert-butoxide (10mmol), tris (dibenzylideneacetone) dipalladium (0.06 mmol), tri-tert-butylphosphine (0.12mmol) and 100mL of xylene into a reaction bottle, heating to 140 ℃ for reaction for 15h, monitoring the reaction by TLC (thin layer chromatography), cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain the compound P33.
Synthesis example 7:
synthesis of Compound P51
The difference from Synthesis example 4 was that 10-bromo-7H-benzocarbazole was replaced with an equivalent amount of 11-bromo-benzofuran [2,3-c ] carbazole and 2-chloro-3-phenylquinoxaline was replaced with an equivalent amount of 2- (2-fluorophenyl) -4, 6-diphenyl- (1,3,5) triazine to give compound P51.
Synthesis example 8:
synthesis of Compound P72
Figure BDA0002491591490000482
Adding M6(0.1mol), pinacol diboron diboride (0.15mol), potassium acetate (0.2mol), palladium [1,1' -bis (diphenylphosphino) ferrocene ] dichloride (0.001mol) and 300mL of dioxane into a reaction bottle, heating to 110 ℃ for reaction for 12 h, monitoring by TLC to complete reaction, cooling, adding water, extracting by dichloromethane, and concentrating an organic phase to obtain P72-A.
Adding P72-A (50mmol), 11-bromo-8H-benzo [4,5] thiophene [2,3-c ] carbazole (50mmol), potassium carbonate (10mmol), tetrakis (triphenyl) phosphine palladium (0.1mmol), 50mL of water and 150mL of dioxane into a reaction bottle, heating to 110 ℃ for reaction for 11H, monitoring the reaction by TLC, cooling, adding water and dichloromethane, separating an organic phase, concentrating, and purifying by column chromatography to obtain a compound P72-B.
Adding P72-B (30mmol), 2-chloro-4, 6-diphenylpyrimidine (50mmol), cesium carbonate (60mmol) and 150mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 8h, monitoring the reaction by TLC, cooling, adding water, filtering, and purifying a filter cake by column chromatography to obtain the compound P72.
Synthesis example 9:
synthesis of Compound P9
The difference from Synthesis example 4 was that 10-bromo-7H-benzocarbazole was replaced with an equivalent amount of 11-bromo-benzofuran [2,3-c ] carbazole and 2-chloro-3-phenylquinoxaline was replaced with an equivalent amount of 2-chloro-4-phenyl-quinazoline to obtain Compound P9. The present invention exemplarily provides specific synthetic methods for the above compounds, and compounds for which specific synthetic methods are not given in the following examples are also prepared by similar methods, and can be obtained only by replacing raw materials, which are not described herein again, or can be prepared by other methods in the prior art by those skilled in the art.
To verify the certainty of the molecular structure of the compound of formula I used in the examples of the present invention, we confirmed it by elemental analysis (seimer fly FLASH 2000CHNS/O organic element analyzer) and mass spectrometry information (ZAB-HS type mass spectrometer manufactured by Micromass corporation, uk), with the results shown in table 1.
Table 1:
Figure BDA0002491591490000491
Figure BDA0002491591490000501
device example 1
The organic electroluminescent device is provided, and the preparation method comprises the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the ITO anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum thermal evaporation on the anode layer film in sequence to obtain a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer, a 60nm compound HT-4 as a hole transport layer, a 5nm compound HT-48 as an electron blocking layer, a 40nm compound P1: RPD-8 (100:3, w/w) as a light emitting layer, a 5nm ET-23 as a hole blocking layer, a 25nm compound ET-46: ET-57(50/50, w/w) mixture as an electron transport layer, 1nm LiF as an electron injection layer, and 150nm metal aluminum as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Device examples 2 to 9, device comparative examples 1 to 3 differ from device example 1 only in that the compound P1 of the present invention as a host material of a light-emitting layer was replaced with the compound of the present invention and the compound of the prior art shown in table 2.
The light-emitting layer main body materials adopted in the device comparative examples 1 to 3 are respectively compounds C1, C2 and C3 in the prior art with the following structural formulas:
Figure BDA0002491591490000502
and (3) performance testing:
the organic electroluminescent devices prepared in examples and comparative examples were measured for driving voltage and current efficiency and lifetime of the devices at the same luminance using a PR 750 type photoradiometer of Photo Research, a ST-86LA type luminance meter (photoelectric instrument factory of university of beijing), and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 3000cd/m2The voltage at that time is the driving voltage, and the current density at that time is measured(ii) a The ratio of the brightness to the current density is the current efficiency; the current efficiency of comparative example 1 was taken as 1.00, and the remainder was a ratio to the current efficiency of comparative example 1.
The results of the performance tests are shown in table 2.
Table 2:
Figure BDA0002491591490000511
as can be seen from table 2, in the case that the material schemes and the preparation processes of other functional layers in the organic electroluminescent device structure are completely the same, compared with the comparative example, the organic electroluminescent devices provided in embodiments 1 to 9 of the device of the present invention have higher current efficiency and lower driving voltage. The experimental results show that the novel organic material is used for the organic electroluminescent device, so that the device has lower driving voltage and higher current efficiency.
The experimental data show that the novel organic material is used as a luminescent layer material of an organic electroluminescent device, is an organic luminescent functional material with good performance, and has wide application prospect.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (20)

1. A compound of the general formula has a structure shown in formula I;
Figure FDA0002491591480000011
in the formula I, X is1～X22Each independently selected from C, CR1Or N, said R1Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of C, B, C, B, C, B6, B3624, B1Independently with the attached aromatic ring to form a ring or not;
in the formula I, Ar is1One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
in the formula I, L is1And L2Each independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
2. The compound according to claim 1, which has a structure represented by any one of the following formulae (i-1) to (i-4):
Figure FDA0002491591480000012
Figure FDA0002491591480000021
in formulae (I-1) to (I-4), Ar1、L1、L2、X1～X22Are as defined in formula I;
preferably, the compound of the present invention has a structure represented by the formula (I-1) or the formula (I-2);
still preferably, the compound of the present invention has the structure represented by the formula (I-2).
3. The compound of claim 1, having the structure of formula (i-a) or formula (i-b):
Figure FDA0002491591480000022
in the formulae (I-a) and (I-b), Ar1、L1、L2、X1～X22Are as defined in formula I.
4. A compound according to any one of claims 1 to 3, said X15-X18Are each independently selected from CR1Said R is1Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of C, B, C, B, C, B, C, B, C, B, C, B1Independently fused with the connected benzene ring to form a ring or not fused to form a ring, and is connected to form a ring through-O-, -S-, -CR8R9-, C ═ C or single bond, and R8And R9Independently selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted COne of C3-C30 heteroaryl;
preferably, X is15-X18Are each independently selected from CR1Said R is1Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of C, B, C, B, C, B6, B3624, B1Independently not fused with the connected benzene ring to form a ring;
or preferably, said X15-X18Are each independently selected from CR1Said R is1Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, wherein R is selected from the group consisting of C, B, C, B, C, B, C, B, C, B, C, B1Independently fused with the attached benzene ring to form a ring, linked to form a ring via-O-, -S-, -CR8R9-, C ═ C or single bond, and R8And R9Independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
5. The compound according to claim 1, which has a structure represented by any one of the following formulae (i-a-1), (i-a-2), and (i-a-3):
Figure FDA0002491591480000031
in the formulae (I-A-1), (I-A-2) and (I-A-3), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and each is independently selected from one of hydrogen, a substituted or unsubstituted C1 to C10 chain alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C10 silyl group, a substituted or unsubstituted C6 to C30 arylamino group, a substituted or unsubstituted C3 to C30 heteroarylamino group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group;
preferably, the compound has a structure represented by any one of the following formulae (I-A-1-1), (I-A-1-2), (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4):
Figure FDA0002491591480000041
formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), wherein Ar is defined in formula (I-A-3-4)1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and is each independently selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, andone of substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
alternatively, it is preferable that the compound has a structure represented by any one of the following formulae (I-A-1-a), (I-A-1-b), (I-A-2-a), (I-A-2-b), (I-A-3-a), (I-A-3-b):
Figure FDA0002491591480000051
in the formula (I-A-1-a), the formula (I-A-1-b), the formula (I-A-2-a), the formula (I-A-2-b), the formula (I-A-3-a), the formula (I-A-3-b), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1' represents a single substituent to the maximum permissible substituent, and each is independently one selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
6. The compound according to claim 1, which has a structure represented by any one of the following formulae (I-B-1), (I-B-2), (I-B-3), (I-B-4), (I-B-5), and (I-B-6):
Figure FDA0002491591480000061
formula (I-B-1) and formula(I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5) and formula (I-B-6), wherein Ar is as defined above1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said Y is selected from S or O, said R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
preferably, the compound has the following formula (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), A structure represented by any one of formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4):
Figure FDA0002491591480000071
Figure FDA0002491591480000081
Figure FDA0002491591480000091
formula (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2),Formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3) and formula (I-B-6-4), wherein Ar is as defined in the description1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said Y is selected from S or O, said R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
alternatively, it is preferable that the compound has a structure represented by any one of the following formulae (I-B-1-a), (I-B-1-B), (I-B-2-a), (I-B-2-B), (I-B-3-a), (I-B-3-B), (I-B-4-a), (I-B-4-B), (I-B-5-a), (I-B-5-B), (I-B-6-a), and (I-B-6-B):
Figure FDA0002491591480000101
Figure FDA0002491591480000111
in the formula (I-B-1-a), the formula (I-B-1-B), the formula (I-B-2-a), the formula (I-B-2-B), the formula (I-B-3-a), the formula (I-B-3-B), the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B), Ar is represented by the general formula1、L1、L2、X1～X14、X19～X22Are all as defined inThe definitions in formula I are the same, Y is selected from S or O, and R is2And R3Each independently represents a single substituent to the maximum permissible substituent, and each independently is one selected from hydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, halogen, a cyano group, a nitro group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C10 silyl group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.
7. The compound according to claim 1, which has a structure represented by any one of the following formulae (I-C-1), (I-C-2), (I-C-3), (I-C-4), (I-C-5), (I-C-6), (I-C-7), (I-C-8), (I-C-9), (I-C-10), (I-C-11), and (I-C-12):
Figure FDA0002491591480000112
Figure FDA0002491591480000121
Figure FDA0002491591480000131
formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), wherein Ar is Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R4、R5、R6And R7Each independently represents a single substituent to the maximum permissibleAnd substituents each independently selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
8. The compound of claim 1, having the structure shown in formulas (i-D) below:
Figure FDA0002491591480000132
in the formula (I-D), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1One selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
preferably, the compound has a structure represented by any one of the following formulae (I-D-1), (I-D-2), (I-D-3), and (I-D-4):
Figure FDA0002491591480000141
in the formula (I-D-1), the formula (I-D-2), the formula (I-D-3) and the formula (I-D-4), Ar is1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1One selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
alternatively, preferably, the compound has a structure represented by any one of the following formulae (I-D-a) and (I-D-b):
Figure FDA0002491591480000142
in the formulae (I-D-a) and (I-D-b), Ar1、L1、L2、X1～X14、X19～X22Are as defined in formula I, said R1One selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
9. The compound according to any one of claims 1 to 8, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), Formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
said X1～X14Are each independently C or CR1Preferably, said R1Are all hydrogen;
said X19～X22Are each independently C or CR1Preferably, said R1Are all hydrogen.
10. The compound according to any one of claims 1 to 8, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), Formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
ar is1Selected from substituted or unsubstituted C3-C30 electron-deficient heteroaryl;
preferably, Ar is1Selected from nitrogen-containing substituted or unsubstituted C3-C30 electron-deficient heteroaryl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
11. The compound according to any one of claims 1 to 8, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), Formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
ar is1Has one of the following structures (3-1) to (3-4):
Figure FDA0002491591480000161
in the formula (3-1), the Z1、Z2、Z3、Z4And Z5Each independently selected from CR10Or an N atom, and Z1、Z2、Z3、Z4And Z5At least one of which is an N atom,
in the formula (3-2), the Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13Each independently selected from CR10Or an N atom, and Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least one of which is an N atom,
in the formula (3-3), the Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23Each independently selected from CR10Or an N atom, and Z14、Z15、Z16、Z17、Z18、Z19、Z20、Z21、Z22And Z23At least one of which is an N atom,
in the formula (3-4), Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33Each independently selected from CR10Or an N atom, and Z24、Z25、Z26、Z27、Z28、Z29、Z30、Z31、Z32And Z33At least one of which is an N atom,
the R is10One selected from the group consisting of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C10 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
wherein represents an access bond to a group;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
12. The compound of claim 11, said Ar1Has the structure shown in (3-1) or (3-2);
preferably, in the formula (3-1), Z1、Z2、Z3、Z4And Z5At least two of which are N atoms;
preferably, in the formula (3-2), Z6、Z7、Z8、Z9、Z10、Z11、Z12And Z13At least two of which are N atoms.
13. The compound according to any one of claims 1 to 8, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), Formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
ar is1One selected from the following substituted or unsubstituted groups: pyridyl, quinolyl, quinazolinyl, triazinyl, pyrimidinyl or quinoxalinyl;
preferably, Ar is1One selected from the following substituted or unsubstituted groups: quinazolinyl, quinoxalinyl, triazinyl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
14. The compound according to any one of claims 1 to 8, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), Formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B):
ar is1One selected from substituted or unsubstituted A1-A14 groups:
Figure FDA0002491591480000181
wherein, represents the access bond of the group,
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
15. The compound according to any one of claims 1 to 8, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), Formula (I-B-5-4), formula (I-B-6-1), formula (I-B-6-2), formula (I-B-6-3), formula (I-B-6-4), (I-B-1-a), formula (I-B-1-B), formula (I-B-2-a), formula (I-B-2-B), formula (I-B-3-a), formula (I-B-3-B), formula (I-B-4-a), formula (I-B-4-B), formula (I-B-5-a), formula (I-B-5-B), formula (I-B-6-a) and formula (I-B-6-B), said Ar1One selected from the group consisting of B1-B19:
Figure FDA0002491591480000191
wherein denotes the access bond of the group.
16. The compound according to any one of claims 1 to 15, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), In the formula (I-B-5-4), the formula (I-B-6-1), the formula (I-B-6-2), the formula (I-B-6-3), the formula (I-B-6-4), (I-B-1-a), the formula (I-B-1-B), the formula (I-B-2-a), the formula (I-B-2-B), the formula (I-B-3-a), the formula (I-B-3-B), the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B), said L1Selected from single bond or substituted or unsubstituted groupOne of them is: phenylene, naphthylene, biphenylene;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
17. The compound according to any one of claims 1 to 15, wherein the compound of the above formula I, formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-a), formula (I-B), formula (I-A-1), formula (I-A-2), formula (I-A-3), formula (I-B-1), formula (I-B-2), formula (I-B-3), formula (I-B-4), formula (I-B-5), formula (I-B-6), formula (I-C-1), formula (I-C-2), formula (I-C-3), formula (I-C-4), formula (I-C-5), Formula (I-C-6), formula (I-C-7), formula (I-C-8), formula (I-C-9), formula (I-C-10), formula (I-C-11), formula (I-C-12), formula (I-D), (I-D-1), formula (I-D-2), formula (I-D-3), formula (I-D-4), (I-D-a), formula (I-D-b), formula (I-A-1-1), formula (I-A-1-2), formula (I-A-1-3), formula (I-A-1-4), formula (I-A-2-1), Formula (I-A-2-2), formula (I-A-2-3), formula (I-A-2-4), formula (I-A-3-1), formula (I-A-3-2), formula (I-A-3-3), formula (I-A-3-4), (I-A-1-a), formula (I-A-1-B), formula (I-A-2-a), formula (I-A-2-B), formula (I-A-3-a), formula (I-A-3-B), (I-B-1-1), formula (I-B-1-2), formula (I-B-1-3), Formula (I-B-1-4), formula (I-B-2-1), formula (I-B-2-2), formula (I-B-2-3), formula (I-B-2-4), formula (I-B-3-1), formula (I-B-3-2), formula (I-B-3-3), formula (I-B-3-4), formula (I-B-4-1), formula (I-B-4-2), formula (I-B-4-3), formula (I-B-4-4), formula (I-B-5-1), formula (I-B-5-2), formula (I-B-5-3), In the formula (I-B-5-4), the formula (I-B-6-1), the formula (I-B-6-2), the formula (I-B-6-3), the formula (I-B-6-4), (I-B-1-a), the formula (I-B-1-B), the formula (I-B-2-a), the formula (I-B-2-B), the formula (I-B-3-a), the formula (I-B-3-B), the formula (I-B-4-a), the formula (I-B-4-B), the formula (I-B-5-a), the formula (I-B-5-B), the formula (I-B-6-a) and the formula (I-B-6-B),
said L2Selected from single bond or substituted or unsubstitutedOne of the following groups: phenylene, naphthylene, biphenylene;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 silyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
18. The compound of claim 1, having the structure shown below:
Figure FDA0002491591480000211
Figure FDA0002491591480000221
Figure FDA0002491591480000231
Figure FDA0002491591480000241
Figure FDA0002491591480000251
Figure FDA0002491591480000261
Figure FDA0002491591480000271
Figure FDA0002491591480000281
Figure FDA0002491591480000291
Figure FDA0002491591480000301
Figure FDA0002491591480000311
19. use of a compound according to any one of claims 1 to 18 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
preferably, the compound is applied as a light emitting layer material in an organic electroluminescent device, and more preferably as a light emitting layer host material.
20. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 17;
preferably, the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is arranged between the hole transport region and the electron transport region; wherein the light-emitting layer contains the compound according to any one of claims 1 to 18.
CN202010406714.8A 2020-05-14 2020-05-14 Organic compound and application thereof in organic light-emitting field Pending CN113666913A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190061649A (en) * 2017-11-28 2019-06-05 롬엔드하스전자재료코리아유한회사 Organic electroluminescent compound and organic electroluminescent device comprising the same
CN112209802A (en) * 2019-07-09 2021-01-12 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN112939946A (en) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 Compound and application thereof
CN113004189A (en) * 2019-12-18 2021-06-22 北京鼎材科技有限公司 Compound and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190061649A (en) * 2017-11-28 2019-06-05 롬엔드하스전자재료코리아유한회사 Organic electroluminescent compound and organic electroluminescent device comprising the same
CN112209802A (en) * 2019-07-09 2021-01-12 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN112939946A (en) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 Compound and application thereof
CN113004189A (en) * 2019-12-18 2021-06-22 北京鼎材科技有限公司 Compound and application thereof

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