CN115028538A - Compound containing multiple arylamine structures and organic electroluminescent device containing compound - Google Patents

Compound containing multiple arylamine structures and organic electroluminescent device containing compound Download PDF

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CN115028538A
CN115028538A CN202110234244.6A CN202110234244A CN115028538A CN 115028538 A CN115028538 A CN 115028538A CN 202110234244 A CN202110234244 A CN 202110234244A CN 115028538 A CN115028538 A CN 115028538A
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尚书夏
王芳
张兆超
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses a compound containing a polyarylamine structure and an organic electroluminescent device containing the compound, belonging to the technical field of semiconductors. The compound containing the polyarylamine structure is structurally shown in a general formula (1), aromatic rings are used as bridges in the middle of the compound, the arylamines are dispersedly connected on the aromatic rings in a specific mode, the connection density of each arylamine is higher, so that the compound disclosed by the invention has excellent hole migration capability, and the branched chain contains groups such as spirofluorene, carbazole or benzo five-membered ring types, so that the rigidity of molecules is integrally improved, the structure type has higher glass transition temperature, excellent film phase stability and excellent high-temperature weather resistance, and the compound has stronger hole injection transmission capability and appropriate energy level when being applied to an organic electroluminescent device, and holes can be effectively transmitted and injected into a light-emitting layer, so that the high-efficiency light emission of the organic electroluminescent device under low driving voltage can be realized.

Description

Compound containing multiple arylamine structures and organic electroluminescent device containing compound
Technical Field
The invention relates to the technical field of semiconductors, in particular to a compound containing a polyarylamine structure and an organic electroluminescent device containing the compound.
Background
Carriers (holes and electrons) in an organic electroluminescent device (OLED) are injected into the device from two electrodes of the device respectively under the driving of an electric field, and meet recombination to emit light in an organic light emitting layer. High performance organic electroluminescent devices require various organic functional materials to have good photoelectric properties. For example, as a charge transport material, it is required to have good carrier mobility. The hole injection layer material and the hole transport layer material used in the existing organic electroluminescent device have relatively weak injection and transport characteristics, and the hole injection and transport rate is not matched with the electron injection and transport rate, so that the composite region has large deviation, and the stability of the device is not facilitated. In addition, reasonable energy level matching between the hole injection layer material and the hole transport layer material is an important factor for improving the efficiency and the service life of the device, and therefore, how to adjust the balance between holes and electrons and adjust the recombination region is an important subject in the field.
Blue organic electroluminescent devices are always soft ribs in the development of full-color OLEDs, and the efficiency, the service life and other properties of blue light devices are difficult to be comprehensively improved at present, so that how to improve the properties of the blue light devices is still a crucial problem and challenge in the field. Most of blue host materials currently used in the market are electron-biased hosts, and therefore, in order to adjust the carrier balance of the light-emitting layer, a hole-transporting material is required to have excellent hole-transporting performance. The better the hole injection and transmission, the more the composite region will shift to the side far away from the electron blocking layer, so as to far away from the interface to emit light, thus improving the performance of the device and prolonging the service life. Therefore, the hole transport region material is required to have high hole injection property, high hole mobility, high electron blocking property, and high electron weatherability.
Since the hole transport material has a large film thickness, the heat resistance and amorphousness of the material have a crucial influence on the lifetime of the device. Materials with poor heat resistance are easy to decompose in the evaporation process, pollute the evaporation cavity and damage the service life of devices; the material with poor film phase stability can be crystallized in the use process of the device, so that the service life of the device is shortened. Therefore, the hole transport material is required to have high film phase stability and decomposition temperature during use. However, the development of materials for stable and effective organic material layers for organic electroluminescent devices has not been sufficiently realized. Therefore, there is a continuous need to develop a new material to better meet the performance requirements of the organic electroluminescent device.
Disclosure of Invention
In order to solve the problems in the prior art, the applicant provides a compound containing a polyarylamine structure, aromatic rings are used as bridging in the compound, arylamines are dispersedly connected on the aromatic rings in a characteristic mode, and the compound has excellent hole transport capability and stability. When the hole transport material of the organic electroluminescent device is formed by using the polyarylate, the device can simultaneously obtain the effects of reducing the starting voltage and prolonging the service life.
The technical scheme of the invention is as follows:
a compound containing a polyaromatic amine structure, the compound structure is shown as a general formula (1):
Figure BDA0002960043390000011
in the general formula (1), A represents a structure shown in a general formula (2), a general formula (3), a general formula (4) or a general formula (5);
c represents a structure represented by a general formula (2), a general formula (3), a general formula (4) or a general formula (5), and A and C do not represent a structure represented by the general formula (2) at the same time;
b represents a structure shown in a general formula (3), a general formula (4) or a general formula (5);
and A, B, C has at most one group selected from the group consisting of structures represented by formula (4) or formula (5);
Figure BDA0002960043390000021
in the general formula (2), the general formula (3), the general formula (4) and the general formula (5), L, L 6 Each independently represents phenylene, naphthylene or biphenylene;
said L 1 、L 2 、L 3 、L 4 、L 5 Each independently represents a single bond, phenylene, naphthylene or biphenylene;
the R is 1 、R 2 、R 3 、R 4 Independently represent substituted or substituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the substituents for the substituent groups are optionally selected from deuterium, tritium, C 1-10 Alkyl of (C) 6 -C 30 One or more of aryl, C2-C30 heteroaryl containing one or more heteroatoms;
the heteroatom is an oxygen, sulfur or nitrogen atom.
In a preferred embodiment, the R group 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl; and R is present in the general formula (1) 1 、R 2 、R 3 Or R 4 At least one of them is represented by a substituted or unsubstituted spirofluorenyl group.
Preferably, A, C in the general formula (1) represents a structure represented by a general formula (2) or a general formula (3), and A and C do not simultaneously represent a structure represented by the general formula (2);
b represents a structure shown as a general formula (3);
l represents phenylene, naphthylene or biphenylene;
said L is 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene, naphthylene or biphenylene;
R 1 、R 2 、R 3 、R 4 each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthylene and piperonyl.
Preferably, A in the general formula (1) is represented by a structure shown in a general formula (4) or a general formula (5);
b represents a structure shown in a general formula (3);
c represents a structure shown in a general formula (2) or a general formula (3);
the L, L 5 、L 6 Each independently represents phenylene, naphthylene or biphenylene;
said L 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene, naphthylene or biphenylene;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthenyl and piperonyl.
Preferably, A in the general formula (1) is represented by a structure shown in a general formula (2) or a general formula (3);
b represents a structure shown as a general formula (3);
c represents a structure shown in a general formula (4) or a general formula (5);
the L, L 5 、L 6 Each independently represents phenylene, naphthylene or biphenylene;
said L 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene, naphthylene or biphenylene;
the R is 1 、R 2 、R 3 、R 4 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzeneOne of a furanyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted acenaphthenyl group, a substituted unsubstituted piperonyl group, a substituted unsubstituted indenyl group, and a substituted unsubstituted carbazolyl group;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthylene and piperonyl.
Preferably, the structure of the compound is shown as a general formula (6) or a general formula (7):
Figure BDA0002960043390000031
l represents phenylene, naphthylene or biphenylene;
said L 1 、L 2 、L 3 、L 4 、L 7 、L 8 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthenyl and piperonyl.
Preferably, the structure of the compound is shown as any one of general formula (8) to general formula (11):
Figure BDA0002960043390000032
l is phenylene, naphthylene or biphenylene;
said L 5 Represents a single bond or phenyl;
said L 6 Represented by phenylene or naphthylene;
said L 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthylene and piperonyl.
Preferably, the structure of the compound is shown as any one of general formula (12) or general formula (13):
Figure BDA0002960043390000041
l is phenylene, naphthylene or biphenylene;
said L 5 Represents a single bond or phenyl;
said L is 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene or phenyleneA naphthyl group;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthenyl and piperonyl.
Preferably, the structure of the compound is shown as any one of general formula (14) to general formula (16):
Figure BDA0002960043390000042
l represents phenylene or naphthylene;
said L 1 、L 2 、L 3 、L 4 、L 7 、L 8 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tert-butyl, adamantyl, phenyl, naphthyl and biphenyl.
Preferably, the structure of the compound is shown as a general formula (17) or a general formula (18):
Figure BDA0002960043390000051
l represents phenylene or naphthylene;
said L 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
Preferably, the specific structure of the compound is any one of the following structures:
Figure BDA0002960043390000052
Figure BDA0002960043390000061
Figure BDA0002960043390000071
Figure BDA0002960043390000081
Figure BDA0002960043390000091
Figure BDA0002960043390000101
Figure BDA0002960043390000111
Figure BDA0002960043390000121
Figure BDA0002960043390000131
Figure BDA0002960043390000141
Figure BDA0002960043390000151
an organic electroluminescent device comprising an anode, a hole transport region, a light-emitting region, an electron transport region and a cathode in this order, wherein the hole transport region comprises the polyarylamine structural compound;
preferably, the hole transport region comprises a hole injection layer, a first hole transport layer and an electron blocking layer, and more preferably, the first hole transport layer and the hole injection layer comprise the polyarylamine structural compound; more preferably, the first hole transport layer is composed of the aromatic amine structural compound, and the hole injection layer is composed of the polyarylamine structural compound and other doping materials conventionally used for the hole injection layer.
Preferably, the electron transport region comprises a nitrogen heterocyclic compound represented by the following general formula (19):
Figure BDA0002960043390000152
in the general formula (19), Ar 1 、Ar 2 、Ar 3 Independently of one another, represent substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C containing one or more hetero atoms 2 -C 30 One of heterocyclic groups;
L 1 selected from single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 2 -C 30 One of a heterocyclylene group;
X 1 、X 2 、X 3 independently of one another, N or CH, X 1 、X 2 、X 3 Represents N;
the substituents for the substituent groups are optionally selected from deuterium, tritium, C 1-10 Alkyl of (C) 6 -C 30 One or more of aryl, C2-C30 heteroaryl containing one or more heteroatoms; the heteroatom is selected from N, O or S.
Preferably, the electron transport region comprises an electron transport layer and an electron injection layer, wherein the electron transport layer comprises the nitrogen heterocyclic compound; the electron injection layer is made of an N-type metal material.
The beneficial technical effects of the invention are as follows:
although the compound and the comparative structure are wholly in a polyaromatic amine type with an aromatic ring as a bridge in the middle, the branched chain in the compound and the comparative structure mostly contain spirofluorene, carbazole and other groups, so that the rigidity of molecules is integrally improved, the structural type has higher glass transition temperature and excellent stability, and the device is prevented from being aged due to heat generated in the lighting process.
The compound has high mobility, so that the compound has excellent hole transport performance, and can obviously reduce the voltage of the device when being applied to an OLED device.
The compound provided by the invention has a proper HOMO energy level, can form a stable CT complex with a P doping material under a low doping proportion, further improves the hole injection efficiency, and reduces the risk of Cross-talk (red, green and blue pixels are subjected to color crosstalk due to different starting voltages of the red, green and blue pixels, wherein the starting voltage of the blue pixel is highest, and when the blue pixel is lighted, the risk of lighting an adjacent pixel point is caused).
In addition, the polyaromatic amine compound of the invention is combined with nitrogen heterocyclic electron transport materials, so that electrons and holes are in an optimal balance state, and the polyaromatic amine compound has higher efficiency and excellent service life, especially high-temperature service life of devices.
The organic electroluminescent device is made by combining materials with excellent hole and electron injection/transmission performance, film stability and weather resistance, the composite efficiency of electrons and holes is improved, the exciton utilization rate is improved, and the obtained device has low driving voltage and long service life.
Drawings
FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to the present invention.
In the figure: 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. The following description of at least one exemplary embodiment is merely illustrative in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
In the present invention, unless otherwise specified, all operations are carried out under ambient temperature and pressure conditions.
In the present invention, unless otherwise specified, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule. In addition, the "difference in HOMO energy level" and the "difference in LUMO energy level" referred to in the present specification mean a difference in absolute value of each energy value. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
In the present invention, when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like reference numerals refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, and other structures, terms such as "upper", "lower", "top", and "bottom" used to indicate orientations only indicate orientations in a certain specific state, and do not mean that the related structures can exist only in the orientations; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of the electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side away from the substrate is the "top" side.
In this specification, the term "substituted" means that one or more hydrogen atoms on the designated atom or group are replaced with the designated group, provided that the designated atom's normal valency is not exceeded in the present context.
In this specification, the term "C 6 -C 30 Aryl "or" C 6 -C 30 Arylene "refers to a fully unsaturated monocyclic, polycyclic, or fused polycyclic (i.e., rings that share a pair of adjacent carbon atoms) system having 6 to 30 ring carbon atoms.
In this specification, the term "C 2 -C 30 Heterocyclyl "refers to a saturated, partially saturated, or fully unsaturated cyclic group having 2 to 30 ring carbon atoms and containing at least one heteroatom selected from N, O and S, including but not limited to heteroaryl, heterocycloalkyl, fused rings, or combinations thereof. When the heterocyclyl is a fused ring, each or all of the rings of the heterocyclyl may contain at least one heteroatom.
In the present specification, the substituted or unsubstituted fluorenyl group means a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, and a substituted or unsubstituted spirofluorenyl group.
More precisely, substituted or unsubstituted C 6 -C 30 Aryl and/or substituted or unsubstituted C 2 -C 30 The heterocyclic group means a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted m-terphenylyl group, a substituted or unsubstituted terphenylyl group
Figure BDA0002960043390000171
Radical, substituted or unsubstituted biphenylene, substituted or unsubstitutedSubstituted or unsubstituted indenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolyl, Substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof or fused rings of combinations of the foregoing groups, but not limited thereto.
In the present specification, substituted or unsubstituted C 6 -C 30 Arylene or substituted or unsubstituted C 2 -C 30 Heterocyclylene means, respectively, a substituted or unsubstituted C as defined above and having two linking groups 6 -C 30 Aryl or substituted or unsubstituted C 5 -C 30 A heterocyclic group such as a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted tetracylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted paratriphenylene group, a substituted or unsubstituted metatriphenylene group, a substituted or unsubstituted phenylene group
Figure BDA0002960043390000172
A group, a substituted or unsubstituted triphenylene ene, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxazolylene group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, A substituted or unsubstituted quinolylene group, a substituted or unsubstituted isoquinolylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted naphthyrylene group, a substituted or unsubstituted benzoxazylene group, a substituted or unsubstituted benzothiazylene group, a substituted or unsubstituted acridine group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenoxazylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolyl group, a combination thereof or a fused ring of a combination of the foregoing groups, but is not limited thereto.
In this specification, the hole characteristics refer to characteristics that are capable of supplying electrons when an electric field is applied and holes formed in the anode are easily injected into and transported in the light emitting layer due to the conductive characteristics according to the Highest Occupied Molecular Orbital (HOMO) level.
In the present specification, the electron characteristics refer to characteristics that can accept electrons when an electric field is applied and electrons formed in the cathode are easily injected into and transported in the light emitting layer due to the conductive characteristics according to the Lowest Unoccupied Molecular Orbital (LUMO) level.
Organic electroluminescent device
The invention provides an organic electroluminescent device using a compound containing a polyarylamine structure of general formula (1).
In one exemplary embodiment of the present invention, an organic electroluminescent device may include an anode, a hole transport region, a light emitting region, an electron transport region, and a cathode.
The organic electroluminescent device of the present invention may be a bottom emission organic electroluminescent device, a top emission organic electroluminescent device, and a stacked organic electroluminescent device, which is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use differs depending on the nature of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
Anode
Preferably, the anode may be formed on the substrate. In the present invention, the anode and the cathode are opposed to each other. The anode may be made of a conductor having a high work function to aid hole injection, and may be, for example, a metal such as nickel, platinum, copper, zinc, silver, or an alloy thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and metal oxides, such as ZnO with Al or ITO with Ag; conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene), and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used, and is generally 50-500nm, preferably 70-300nm, and more preferably 100-200nm, and ITO and Ag, which are combinations of metals and metal oxides, are preferably used in the present invention.
Cathode electrode
The cathode may be made of a conductor having a low work function to aid electron injection, and may be, for example, a metal or alloy thereof, such as magnesium, calcium, titanium, or alloys thereof,Sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; materials of multilayer structure, e.g. LiF/Al, Li 2 O/Al and BaF 2 But not limited thereto,/Ca. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20 nm.
Light emitting area
In the present invention, the light emitting region may be disposed between the anode and the cathode, and may include at least one host material and at least one guest material. As the host material and the guest material of the light emitting region of the organic electroluminescent device of the present invention, light emitting layer materials for organic electroluminescent devices known in the art can be used. The host material may be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4' -bis (9-Carbazolyl) Biphenyl (CBP). As the host material, a compound containing an anthracene group can be used. The guest material may be, for example, quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
In a preferred embodiment of the present invention, one or two host material compounds are contained in the light-emitting region.
In a preferred embodiment of the present invention, two host material compounds are contained in the light emitting region, and the two host material compounds may form an exciplex.
In a preferred embodiment of the invention, the host material of the light-emitting region used is selected from one or more of the following compounds BH-1-BH-11:
Figure BDA0002960043390000181
Figure BDA0002960043390000191
in the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve the fluorescent or phosphorescent characteristics of the organic electroluminescent device. Specific examples of the phosphorescent guest material include metal complexes of iridium, platinum, and the like, and for the fluorescent guest material, those generally used in the art may be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds BD-1 to BD-10:
Figure BDA0002960043390000192
in the light emitting region of the present invention, the ratio of the host material to the guest material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the light emitting region may be 10 to 50nm, preferably 15 to 30nm, but the thickness is not limited to this range.
Hole transport region
In the organic electroluminescent device of the present invention, a hole transport region is provided between the anode and the light emitting region, and includes a hole injection layer, a hole transport layer, and an electron blocking layer.
Hole injection layer
The hole injection material used in the hole injection layer (also referred to as an anode interface buffer layer) is a material that can sufficiently accept holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of a host organic material and a P-type dopant material. In order to smoothly inject holes from the anode into the organic film layer, the HOMO level of the host organic material must have a certain characteristic with the P-type dopant material, so that the generation of a charge transfer state between the host material and the dopant material is expected, and ohmic contact between the hole injection layer and the anode is realized, thereby realizing efficient injection of holes from the electrode to the hole injection layer. This feature is summarized as: the difference between the HOMO energy level of the host material and the LUMO energy level of the P-type doping material is less than or equal to 0.4 eV. Therefore, for hole-type host materials with different HOMO levels, different P-type doping materials need to be selected to match with the hole-type host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved.
Preferably, specific examples of the host organic material include: metalloporphyrin, oligothiophene, organic materials of arylamine, hexanitrile hexaazatriphenylene, organic materials of quinacridone, organic materials of perylene, anthraquinone, polyaniline and polythiophene conductive polymers; but is not limited thereto. Preferably, the host organic material is an arylamine-based organic material.
Preferably, the P-type doping material is a compound having charge conductivity selected from the group consisting of: quinone derivatives or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In a preferred embodiment of the present invention, the P-type doping material used is selected from any one of the following compounds HI1 to HI 8:
Figure BDA0002960043390000201
in one embodiment of the invention, the ratio of host organic material to P-type dopant material used is 99:1 to 95:5, preferably 99:1 to 97:3, by mass.
In a preferred embodiment of the invention, the hole injection layer is a mixed film layer of an arylamine compound and a P-type doping material, and the arylamine compound is a compound containing a polyarylamine structure in a general formula (1).
The thickness of the hole injection layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Hole transport layer
In the organic electroluminescent device of the present invention, the hole transport layer may be disposed on the hole injection layer. The hole transport material is suitably a material having a high hole mobility, which can accept holes from the anode or the hole injection layer and transport the holes into the light-emitting layer. Specific examples thereof include: aromatic amine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like, but are not limited thereto. In a preferred embodiment, the hole transport layer comprises the same compound containing a polyarylamine structure of the general formula (1) as the hole injection layer.
The thickness of the hole transport layer of the present invention may be 80-200nm, preferably 100-150nm, but the thickness is not limited to this range.
Electron blocking layer
In the organic electroluminescent device of the present invention, the electron blocking layer may be disposed between the hole transport layer and the light emitting layer, and particularly, contacts the light emitting layer. The electron blocking layer is provided to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transport layer can be precisely controlled. In one embodiment of the present invention, the electron blocking layer material is selected from carbazole-based aromatic amine derivatives. The thickness of the electron blocking layer may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
The invention does not deny the substrate collocation principle of the traditional hole materials, but further superposes the physical parameters screened by the traditional materials, namely, the influence effects of HOMO energy level, carrier mobility, film phase stability, heat resistance stability of the materials and the like on the hole injection efficiency of the organic electroluminescent device are acknowledged. On the basis, the material screening conditions are further increased, and the material selection accuracy for preparing the high-performance organic electroluminescent device is improved by selecting more excellent organic electroluminescent materials for matching the device.
Electron transport region
In the organic electroluminescent device of the present invention, the electron transport region is disposed between the light emitting region and the cathode, and includes an electron transport layer and an electron injection layer, but is not limited thereto.
Electron injection layer
The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
Electron transport layer
The electron transport layer may be disposed over the light emitting film layer or, if present, the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, an electron transport layer material for organic electroluminescent devices known in the art, for example, in Alq, can be used 3 Metal complexes of hydroxyquinoline derivatives typified by BALq and LiQ, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS No: 1459162-51-6), and 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] d]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG201), oxadiazole derivatives, and the like.
In a preferred organic electroluminescent device of the present invention, the electron transport region comprises a nitrogen heterocyclic compound represented by the following general formula (19):
Figure BDA0002960043390000211
in the general formula (19), Ar 1 、Ar 2 、Ar 3 Independently of one another, as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of heterocyclic groups;
L 1 selected from single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of heterocyclylene radicalsSeed;
each of said heteroatoms is independently selected from N, O or S;
X 1 、X 2 、X 3 independently of one another, N or CH, X 1 、X 2 、X 3 Represents N.
In a preferred embodiment of the present invention, the electron transport layer comprises any one of the compounds selected from the group consisting of:
Figure BDA0002960043390000212
Figure BDA0002960043390000221
in a more preferred embodiment of the present invention, the electron transport layer comprises any one of the compounds selected from the group consisting of: (E2) (E5), (E12), (E16) or (E23).
In a preferred embodiment of the present invention, the electron transport layer comprises, in addition to the compound of formula (19), other compounds conventionally used in electron transport layers, such as, for example, Alq3, LiQ, preferably LiQ. In a more preferred embodiment of the present invention, the electron transport layer is composed of one of the compounds of formula (19) and one of the other compounds conventionally used for electron transport layers, preferably LiQ.
The hole injection and transport rates of the hole transport region containing the compounds of the present invention can be well matched to the electron injection and transport rates. Preferably, the hole injection and transport rate of the hole transport region containing the compound of the present invention can be better matched with the electron injection and transport rate of the electron transport region containing the nitrogen heterocycle derivative of the general formula (19).
Thus, in a particular embodiment of the invention, the use of an electron-transport region comprising or consisting of one or more nitrogen-heterocycle derivatives of general formula (19) in combination with a hole-transport region comprising a compound of the invention achieves a relatively better technical result.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
Cover layer
In order to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be added on the cathode of the device. According to the principle of optical absorption and refraction, the CPL cover layer material should have a higher refractive index as well as a better refractive index, and the absorption coefficient should be smaller as well. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL capping layer is typically 5-300nm, preferably 20-100nm and more preferably 40-80nm thick.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.
Hereinafter, an organic electroluminescent device according to an embodiment of the present invention is described.
In the drawings, the thickness of layers, films, substrates, regions, etc. are exaggerated for clarity. Like reference numerals refer to like elements throughout the specification. It will be understood that when an element such as a layer, film, region or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
Fig. 1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Referring to fig. 1, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
The present invention also relates to a method of preparing an organic electroluminescent device comprising sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, LITI, or the like may be used, but are not limited thereto. In the present invention, it is preferable that the respective layers are formed by a vacuum evaporation method. The individual process conditions in the vacuum evaporation process can be routinely selected by the person skilled in the art according to the actual requirements.
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, may be used as a single layer by forming a film in admixture with another material, or may be used as a laminated structure of layers formed alone, layers formed in admixture with each other, or a laminated structure of layers formed alone and layers formed in admixture with each other.
The invention also relates to a full-color display device, in particular a flat panel display device, having three pixels of red, green and blue, comprising the organic electroluminescent device of the invention. The display device may further include at least one thin film transistor. The thin film transistor may include a gate electrode, source and drain electrodes, a gate insulating layer, and an active layer, wherein one of the source and drain electrodes may be electrically connected to an anode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, but is not limited thereto.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some instances, features, characteristics and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics and/or elements described in connection with other embodiments, unless specifically indicated otherwise, as will be apparent to one of ordinary skill in the art upon submission of the present application. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
Unless otherwise indicated, various materials used in the following examples and comparative examples are commercially available or may be obtained by methods known to those skilled in the art.
Example 1: synthesis of compound 7:
step (1)
Figure BDA0002960043390000231
Step (2)
Figure BDA0002960043390000232
Step (3)
Figure BDA0002960043390000233
A250 ml three-necked flask was charged with 0.012mol of the raw material A, 0.01mol of the intermediate B, 0.03mol of potassium tert-butoxide, 1X 10 in a nitrogen-purged atmosphere -4 mol tris (dibenzylideneacetone) dipalladium Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, sample point plate, indicating reaction completion. Naturally cooling, filtering, rotatably evaporating the filtrate, and passing through a silica gel column (silica gel 100-200 meshes, eluent: chloroform: n-hexane: 1:2 (volume ratio)) to obtain an intermediate M. Elemental analysis Structure (molecular formula C) 18 H 13 BrClN): the analysis found value is: c, 60.25; h, 3.67; br, 22.27; cl, 9.86; and N, 3.95. LC-MS ([ M + H)] + ): found 357.95.
In a 500ml three-necked flask, 0.012mol of intermediate M, 0.01mol of raw material C, 0.02mol of sodium carbonate, 150ml of toluene and 30ml of water are added under nitrogen protection, stirred and mixed, and then 1X 10 -4 mol tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 Heating to 105 deg.CAfter 24 hours of flow reaction, the sample was taken from the plate, and the point on the TLC plate where no raw material C was present was completely reacted. Naturally cooling to room temperature, filtering, carrying out reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), and passing through a neutral silica gel column (silica gel 100 meshes and 200 meshes, eluent: chloroform: n-hexane: 1:2 (volume ratio)) to obtain an intermediate P. Elemental analysis Structure (molecular formula C) 36 H 27 ClN 2 ): the analysis found value is: c, 82.67; h, 5.23; cl, 6.76; and N, 5.34. LC-MS ([ M + H)] + ): found 523.06.
A250 ml three-necked flask was charged with 0.012mol of the raw material D, 0.01mol of the intermediate P, 0.03mol of potassium tert-butoxide, 1X 10 in a nitrogen-purged atmosphere -4 mol tris (dibenzylideneacetone) dipalladium Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the plaque taken, indicating completion of the reaction. The mixture is naturally cooled, filtered, and the filtrate is evaporated in a rotary manner and passes through a silica gel column (silica gel 100-200 meshes, and the eluent: chloroform: n-hexane is 1:2 (volume ratio)), so that the compound 7 is obtained. Elemental analysis Structure (molecular formula C) 67 H 47 N 3 ): the analysis found value is: c, 90.03; h, 5.28; and N, 4.69. LC-MS ([ M + H)] + ): found 894.06.
The following numbered compounds were prepared in the same manner as in example 1, and the synthetic raw materials are shown in table 1 below. The synthesis method of the compound of the invention can refer to the prior art CN 110577511A.
For structural analysis of the compounds prepared in the examples, the molecular weights measured by LC-MS are shown in table 1.
TABLE 1
Figure BDA0002960043390000241
Figure BDA0002960043390000251
Example 2: synthesis of Compound 3
Step (1)
Figure BDA0002960043390000261
Step (2)
Figure BDA0002960043390000262
A250 ml three-necked flask was charged with 0.012mol of raw material E, 0.022mol of raw material B, 0.03mol of potassium tert-butoxide, and 1X 10 under a nitrogen atmosphere -4 mol tris (dibenzylideneacetone) dipalladium Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, sample point plate, indicating reaction completion. Naturally cooling, filtering, rotatably evaporating the filtrate, and passing through a silica gel column (silica gel 100-200 meshes, eluent: chloroform: n-hexane: 1:2 (volume ratio)) to obtain an intermediate G. Elemental analysis Structure (molecular formula C) 30 H 23 ClN 2 ): the actual values of elemental analysis are: c, 80.63; h, 5.18; cl, 7.90; and N, 6.29. LC-MS ([ M + H)] + ): found 447.04.
A250 ml three-necked flask was charged with 0.012mol of raw material F, 0.01mol of intermediate G, 0.03mol of potassium tert-butoxide, 1X 10 under an atmosphere of nitrogen gas -4 mol tris (dibenzylideneacetone) dipalladium Pd 2 (dba) 3 ，1×10 -4 mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the plaque taken, indicating completion of the reaction. The mixture is naturally cooled, filtered, and the filtrate is evaporated in a rotary manner and passes through a silica gel column (silica gel 100-200 meshes, and the eluent: chloroform: n-hexane is 1:2 (volume ratio)), so that the compound 3 is obtained. Elemental analysis Structure (molecular formula C) 67 H 47 N 3 ): the elemental analysis found was: c, 90.01; h, 5.27; and N, 4.72. LC-MS ([ M + H)] + ): found 894.23.
Example 3: synthesis of Compound 21
Synthesis of Compound 21 step (1) was the same as step (1) of example 2 above, and step (2) was as follows:
step (2)
Figure BDA0002960043390000263
Adding into 0.012mol in a 500ml three-mouth bottle under the protection of nitrogenThe intermediate G, 0.01mol of the starting material F, 0.02mol of sodium carbonate, 150ml of toluene and 30ml of water are stirred and mixed, and then 1X 10 -4 mol tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 Heating to 105 ℃, refluxing and reacting for 24 hours, taking samples on a sample plate, and taking a point without the raw material F on a thin layer chromatographic plate, wherein the reaction is complete. Naturally cooled to room temperature, filtered, and the filtrate was subjected to rotary evaporation under reduced pressure (-0.09MPa, 85 ℃ C.) to obtain a compound 21 through a neutral silica gel column (silica gel 100-200 mesh; eluent: chloroform: n-hexane: 1:2 (volume ratio)). Elemental analysis Structure (molecular formula C) 67 H 47 N 3 ): the analysis measured value is: elemental analysis found: c, 89.98; h, 5.34; and N, 4.68. LC-MS ([ M + H)] + ): found 894.48.
The following numbered compounds were prepared in the same manner as in example 3, and the synthetic raw materials were as shown in table 2 below.
For structural analysis of the compounds prepared in the examples, the molecular weights measured by LC-MS are shown in table 2:
TABLE 2
Figure BDA0002960043390000271
Detection method
Glass transition temperature Tg: measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter, Nachi company, Germany), the rate of temperature rise was 10 ℃/min.
HOMO energy level: the test was conducted in a vacuum environment by an ionization energy test system (IPS 3).
Eg energy level: the measurement was carried out by means of a two-beam ultraviolet-visible spectrophotometer (model: TU-1901) using a tangent line based on the ultraviolet spectrophotometric (UV absorption) baseline of the material single film and the rising side of the first absorption peak, and calculating the value of the intersection of the tangent line and the baseline.
Hole mobility: the material of the invention is made into a single charge device and is measured by an SCLC method.
Triplet energy level T1: the test conditions of the materials were 2 x 10 as measured by a Fluorolog-3 series fluorescence spectrometer from Horiba -5 mol/L toluene solution.
The results of the physical property tests are shown in Table 3.
TABLE 3
Figure BDA0002960043390000272
Figure BDA0002960043390000281
As can be seen from the data in table 3 above, the compound of the present invention has a suitable HOMO level, a higher hole mobility, and a wider band gap (Eg), and can realize an organic electroluminescent device having high efficiency, low voltage, and long lifetime.
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation is as follows:
Figure BDA0002960043390000282
comparative device example 1
The organic electroluminescent device was prepared as follows:
a) using transparent glass as a substrate, washing the anode layer 2(Ag (100nm)) thereon, namely sequentially performing alkali washing, pure water washing and drying, and then performing ultraviolet-ozone washing to remove organic residues on the surface of the anode layer;
b) on the anode layer 2 after the above washing, HT1 and P-type doped HI1 with a film thickness of 10nm were evaporated as a hole injection layer 3 by a vacuum evaporation apparatus, and the mass ratio of HT1 to HI1 was 97: 3;
c) evaporating a hole transport layer 4 on the hole injection layer in a vacuum evaporation mode, wherein the hole transport layer is made of a compound HT1 and has the thickness of 117 nm;
d) evaporating an electron barrier layer 5 on the hole transport layer in a vacuum evaporation manner, wherein the electron barrier layer is made of EB-1 with the thickness of 10 nm;
e) manufacturing a light-emitting layer 6 of the OLED light-emitting device on the electron blocking layer, wherein the structure of the light-emitting layer 6 comprises the steps that BH-1 used by the OLED light-emitting layer 6 is used as a main material, BD-1 is used as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light-emitting layer is 20 nm;
f) continuing to vapor-deposit HB1 as a hole blocking layer 7 on the light-emitting layer, wherein the vapor-deposition film thickness is 8 nm;
g) evaporating ET1 and LiQ on the hole blocking layer in a vacuum evaporation mode, wherein the mass ratio of ET1 to LiQ is 50:50, the thickness is 30nm, and the layer serves as an electron transport layer 8;
h) evaporating LiF on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the LiF is 1nm, and the layer is an electron injection layer 9;
i) vacuum evaporating an Mg: Ag (1:9) electrode layer with the thickness of 16nm on the electron injection layer, wherein the layer is a cathode layer 10;
j) on the cathode layer, 70nm CP-1 was vacuum-deposited as the CPL layer 11.
Comparative device examples 2 to 3 the process of comparative device example 1 was carried out, except that the organic materials in steps b)/c) were respectively replaced with the organic materials shown in table 4. Device comparative examples 4 to 6 the process of device comparative example 1 was performed, except that the organic materials in b)/c)/g) were respectively replaced with the organic materials shown in table 4. Device preparation examples 1 to 20 were conducted in the same manner as in comparative device example 1 except that the organic materials in steps b)/c) were respectively replaced with the organic materials shown in table 4. Device preparation examples 21 to 30 were conducted in the same manner as in comparative device 1 except that the organic materials in b)/c)/g) were respectively replaced with the organic materials shown in table 4.
TABLE 4
Figure BDA0002960043390000291
Figure BDA0002960043390000301
In the above table, taking example 1 as an example, "3: HI1 (3% 10 nm)" in the second table indicates that the materials used for the hole injection layer are compound (3) and P-type dopant HI1, 3% referring to the weight ratio of P-type dopant HI1 to the materials used for the hole injection layer: 10nm indicates the thickness of the layer; "3 (117 nm)" in the third table indicates that the material used is compound (3) and that the layer thickness is 117 nm. And so on in other tables.
After the OLED light-emitting device was prepared as described above, the cathode and the anode were connected by a known driving circuit, and various properties of the device were measured.
The results of measuring the properties of the devices of examples 1 to 30 and comparative examples 1 to 6 are shown in table 5.
TABLE 5
Figure BDA0002960043390000302
Figure BDA0002960043390000311
Note: voltage, Current efficiency and color coordinates were measured using an IVL (Current-Voltage-Brightness) test System (Fund scientific instruments, Suzhou) at a current density of 10mA/cm 2 (ii) a The life test system is an EAS-62C type OLED device life tester of Japan systems research company; LT95 refers to the time it takes for the device brightness to decay to 95% at a particular brightness; the test temperature for high temperature lifetime is 85 deg.c and LT80 refers to the time it takes for the device brightness to decay to 80% at a particular brightness.
In table 5, the voltage represents the driving voltage of the device, i.e., the device voltage, and the voltage @1nits represents the turn-on voltage, as can be seen from the results of comparative examples 1 to 3 and device examples 1 to 20 in table 5, when the polyarylate of the present invention is used as the hole injection and hole transport layer material, the device voltage is effectively reduced and the device lifetime is improved due to the higher carrier transport rate; as can be seen from the light-on voltage at @1nits, the compound of the invention obviously reduces the light-on voltage of the device and lowers the Cross-talk risk.
It can be seen from the results of comparative examples 4 to 6 and device examples 21 to 30 in table 5 that the polyarylates of the present invention are used in combination with a specific electron transport layer material, and the efficiency and lifetime of the device are effectively improved by the collocation manner.
The compound contains one or more arylamine groups, and the branched chain contains spirofluorene, carbazole and a benzo five-membered ring or heterocyclic ring structure, so that the integral rigidity of molecules is enhanced, the glass transition temperature of the material can be effectively improved, and the group has higher heat-resistant stability, so that the compound has excellent film phase stability and evaporation stability, the interface stability of a device under a high-temperature condition is effectively improved, and the device has excellent high-temperature service life.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and should not be taken as limiting the scope of the present invention, which is intended to cover any modifications, equivalents, improvements, etc. within the spirit and scope of the present invention.

Claims (10)

1. A compound containing a polyaromatic amine structure, which is characterized in that the structure of the compound is shown as a general formula (1):
Figure FDA0002960043380000011
in the general formula (1), A represents a structure shown in a general formula (2), a general formula (3), a general formula (4) or a general formula (5);
c represents a structure shown in a general formula (2), a general formula (3), a general formula (4) or a general formula (5), and A and C do not represent a structure shown in the general formula (2) at the same time;
b represents a structure shown in a general formula (3), a general formula (4) or a general formula (5);
and A, B, C has at most one group selected from the group consisting of structures represented by formula (4) or formula (5);
Figure FDA0002960043380000012
in the general formula (2), the general formula (3), the general formula (4) and the general formula (5), L, L 6 Each independently represents phenylene, naphthylene or biphenylene;
said L 1 、L 2 、L 3 、L 4 、L 5 Each independently represents a single bond, phenylene, naphthylene or biphenylene;
the R is 1 、R 2 、R 3 、R 4 Independently represent substituted or substituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the substituents for the substituent groups are optionally selected from deuterium, tritium, C 1-10 Alkyl of (C) 6 -C 30 One or more of aryl, C2-C30 heteroaryl containing one or more heteroatoms;
the heteroatom is an oxygen, sulfur or nitrogen atom.
2. The compound containing a polyarylamine structure according to claim 1, wherein the compound structure is represented by general formula (6) or general formula (7):
Figure FDA0002960043380000013
l represents phenylene, naphthylene or biphenylene;
said L 1 、L 2 、L 3 、L 4 、L 7 、L 8 Each independently represents a single bond, phenylene or naphthylene;
said R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted spirofluorenyl groupOne of substituted or unsubstituted phenanthryl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthylene and piperonyl.
3. The compound containing a polyarylamine structure according to claim 1, wherein the compound structure is any one of general formula (8) to general formula (11):
Figure FDA0002960043380000021
l is phenylene, naphthylene or biphenylene;
said L 5 Represents a single bond or phenyl;
said L 6 Represented by phenylene or naphthylene;
said L is 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthylene and piperonyl.
4. The compound containing a polyarylamine structure according to claim 1, wherein the compound structure is represented by any one of general formula (12) or general formula (13):
Figure FDA0002960043380000022
l is phenylene, naphthylene or biphenylene;
said L 5 Represents a single bond or phenyl;
said L 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tert-butyl, adamantyl, phenyl, naphthyl, biphenyl, carbazolyl, benzofuranyl, dibenzofuranyl, fluorenyl, phenanthryl, pyrenyl, acenaphthenyl and piperonyl.
5. The compound containing a polyarylamine structure according to claim 1, wherein the compound structure is any one of general formula (14) to general formula (16):
Figure FDA0002960043380000031
l represents phenylene or naphthylene;
said L 1 、L 2 、L 3 、L 4 、L 7 、L 8 Each independently represents a single bond, phenylene or naphthylene;
the R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted acenaphthenyl, substituted or unsubstituted piperonyl, substituted or unsubstituted indenyl, and substituted or unsubstituted carbazolyl;
the substituent used for the substituent group is one or more of deuterium, methyl, tert-butyl, adamantyl, phenyl, naphthyl and biphenyl.
6. The compound containing a polyarylamine structure according to claim 1, wherein the compound structure is represented by general formula (17) or general formula (18):
Figure FDA0002960043380000041
l represents phenylene or naphthylene;
said L 1 、L 2 、L 3 、L 4 Each independently represents a single bond, phenylene or naphthylene;
said R is 1 、R 2 、R 3 、R 4 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted acenaphthylenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted acenaphthenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted acenaphthenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or substituted phenanthrenyl group, a substituted or a substituted phenanthrenyl group, a substituted or a substituted spirofluorenyl group, or a substituted phenanthrenyl group, or a substituted or a substituted phenanthrenyl group, or a substituted or a substituted or a substituted phenanthrenyl group, or a substituted or a substituted or a substituted or a substituted,One of substituted unsubstituted indenyl group and substituted unsubstituted carbazolyl group;
the substituent used for the substituent group is one or more of deuterium, methyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
7. A compound containing a polyarylamine structure as defined in claim 1, wherein the specific structure of the compound is any one of the following structures:
Figure FDA0002960043380000042
Figure FDA0002960043380000051
Figure FDA0002960043380000061
Figure FDA0002960043380000071
Figure FDA0002960043380000081
Figure FDA0002960043380000091
Figure FDA0002960043380000101
Figure FDA0002960043380000111
Figure FDA0002960043380000121
Figure FDA0002960043380000131
Figure FDA0002960043380000141
Figure FDA0002960043380000151
8. an organic electroluminescent device comprising an anode, a hole transporting region, a light emitting region, an electron transporting region and a cathode in this order, wherein the hole transporting region comprises the multiamine structure compound as claimed in any one of claims 1 to 7;
preferably, the hole transport region comprises a hole injection layer, a first hole transport layer and an electron blocking layer, more preferably, the first hole transport layer and the hole injection layer comprise a polyarylamine structural compound of any of claims 1 to 7; more preferably, the first hole transport layer consists of the arylamine structural compound of any one of claims 1 to 7 and the hole injection layer consists of the polyarylamine structural compound of any one of claims 1 to 7 and other doping materials conventionally used for hole injection layers.
9. The organic electroluminescent device according to claim 8, wherein the electron transport region comprises a nitrogen heterocyclic compound represented by the following general formula (19):
Figure FDA0002960043380000152
in the general formula (12), Ar 1 、Ar 2 、Ar 3 Independently of one another, as substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C containing one or more hetero atoms 2 -C 30 One of heterocyclic groups;
L 1 selected from single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 2 -C 30 One of a heterocyclylene group;
X 1 、X 2 、X 3 independently of one another, N or CH, X 1 、X 2 、X 3 Represents N;
the substituents for the substituent groups are optionally selected from deuterium, tritium, C 1-10 Alkyl of (C) 6 -C 30 One or more of aryl, C2-C30 heteroaryl containing one or more heteroatoms;
the heteroatom is selected from N, O or S.
10. A display device comprising the organic electroluminescent device according to any one of claims 8 to 9.
CN202110234244.6A 2021-03-03 2021-03-03 Compound containing multiple arylamine structures and organic electroluminescent device containing compound Withdrawn CN115028538A (en)

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