CN110964002A - Arylamine derivative and organic light-emitting device thereof - Google Patents

Arylamine derivative and organic light-emitting device thereof Download PDF

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CN110964002A
CN110964002A CN201911285995.XA CN201911285995A CN110964002A CN 110964002 A CN110964002 A CN 110964002A CN 201911285995 A CN201911285995 A CN 201911285995A CN 110964002 A CN110964002 A CN 110964002A
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赵倩
刘喜庆
韩春雪
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The invention relates to the technical field of organic photoelectric materials, and provides an arylamine derivative and an organic light-emitting device thereof. The arylamine derivative has a specific structure, so that the arylamine derivative has the advantages of higher glass transition temperature, good thermal stability and more stable compound, and the prepared organic light-emitting device has the advantage of long service life. In addition, the arylamine derivative has higher refractive index, effectively solves the problem of total emission of the interface of the ITO film and the glass substrate and the interface of the glass substrate and the air, reduces the total emission loss and waveguide loss in an OLED device, and improves the light extraction efficiency, thereby improving the luminous efficiency of an organic light-emitting device.

Description

Arylamine derivative and organic light-emitting device thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an arylamine derivative and an organic light-emitting device thereof.
Background
OLEDs are called organic light emitting diodes or organic light emitting displays, which have a number of advantages as an emerging application technology in the display field. The OLED body is light and thin, has unique foldable and bending characteristics, and can realize transparent display, so that the application range of the OLED body can be greatly expanded. The OLED is self-luminous, high in contrast and bright in color. The OLED is all solid, and has good shock resistance. The working temperature range of the OLED is wide, and is as low as-40 ℃ and as high as 80 ℃. The viewing angle of the OLED is wide, and can reach 160 degrees generally. The OLED has the advantages of numerous materials, wide selection range and strong plasticity. The OLED does not need an external backlight source, and is more energy-saving. The OLED does not use heavy metals such as mercury and lead, and the OLED lighting meets the environmental protection requirement under the global advocation of low carbon. The OLED emission is soft and can be freely designed. OLEDs are highly valued globally based on the vast potential applications they exhibit. The OLED mainly shows good application prospect in the aspects of flat panel display, solid-state lighting and LCD backlight. The organic challenges are the same as the technical difficulties of OLED, which hinder its marketable development.
At present, the development of OLED materials has reached a high-speed and mature stage, and hundreds of innovative materials are offered by domestic and foreign material companies for selection. Among them, hole transport Layer materials, electron transport Layer materials, host materials, dopant materials, fluorescent light emitting materials, and phosphorescent light emitting materials have been developed, but the development types of cover Layer materials (Capping layers) are single, and the effect is not ideal.
For the conventional OLED device, the total emission can occur at the interface of the ITO thin film and the glass substrate and at the interface of the glass substrate and the air, so that the light emitted to the front outside of the OLED device accounts for about 20% of the total amount of the light emitting layer of the organic material thin film, the rest about 80% of the light is mainly limited in the organic material thin film, the ITO thin film and the glass substrate in a waveguide mode, the light emitting efficiency of the conventional OLED device is about 20%, and the covering layer material can be used for reducing the total emission loss and the waveguide loss in the OLED device.
In general, in the future, the OLED is developed to be a white light device and a full color display device with high efficiency, long lifetime and low cost, but the industrialization process of the technology still faces many key problems, and how to design a material with better performance for adjustment is a problem that needs to be solved by those skilled in the art.
Disclosure of Invention
The invention aims to provide an arylamine derivative and an organic light-emitting device thereof. The arylamine derivative provided by the invention has good thermal stability and film forming property, the synthesis method is simple and easy to operate, and an organic light-emitting device prepared from the arylamine derivative has good luminous efficiency and service life performance.
The present invention solves the above problems by providing an aromatic amine derivative as a main constituent of a cap layer in an organic light-emitting device.
The arylamine derivative is represented by a formula I,
Figure BDA0002317993110000021
wherein R is1、R2Together with the atoms to which they are attached form a substituted or unsubstituted seven-membered ring, a substituted or unsubstituted six-membered ring;
Ar1、Ar2、Ar3independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C3-C24 heteroaryl;
wherein Ar is1、Ar2、Ar3At least one is a group of formula I-a:
Figure BDA0002317993110000022
wherein, the ring A is selected from any one of groups shown in 1a to 1 d:
Figure BDA0002317993110000023
"" is the position of attachment of the group;
Z1selected from O, S, N-R1Wherein R is1Is phenyl, Z2Is selected from N;
R0one selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, acridinyl, phenanthryl, triphenylene, phenoxazinyl, phenothiazinyl, phenoxathinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, thienyl, furyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, benzodibenzofuryl, and benzo 9, 9-dimethylfluorenyl, n is an integer of 0 to 4;
L0one kind selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein the substituent is selected from one or more of methyl, ethyl, isopropyl, tertiary butyl, phenyl;
l is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirofluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.
The invention also provides an organic electroluminescent device which comprises a cathode, an anode and one or more organic layers, wherein at least one layer of the organic layers, preferably a covering layer, contains any one or the combination of at least two of the arylamine derivatives.
Advantageous effects
The invention provides an aromatic amine derivative and an organic light-emitting device thereof, on one hand, the aromatic amine derivative is connected with electron-donating groups such as imino stilbene group and acridine group, and different substituents such as alkyl, aryl, condensed ring compound, heterocyclic compound, condensed heterocyclic compound and the like are introduced into different positions on molecules so as to reduce the symmetry of the whole molecule, the number of molecular isomers is increased, the film-forming property of the molecule is better, and the thermal stability of the film is also improved. The arylamine derivative has higher Tg (glass transition temperature) temperature, so that the arylamine derivative has good thermal stability, the compound is more stable, and the prepared organic light-emitting device has the advantage of long service life.
On the other hand, due to the existence of pi-pi stacking and the interaction between pi cations on the aromatic conjugate plane of five-membered nitrogen-containing heterocyclic groups such as benzoxazole, benzothiazole, benzimidazole and the like, the benzene ring structures of the five-membered nitrogen-containing heterocyclic groups have high plasticity in the aspect of chemical modification. Benzoxazole, benzothiazole and benzimidazole as substituents can effectively inhibit aggregation-induced fluorescence quenching caused by plane conjugation, and increase the luminous efficiency of the luminescent material, and the thermal stability and solubility of molecules.
Moreover, the arylamine derivative has higher refractive index, effectively solves the problem of total emission of the interface of the ITO film and the glass substrate and the interface of the glass substrate and the air, reduces the total emission loss and waveguide loss in an OLED device, and improves the light extraction efficiency, thereby improving the luminous efficiency of an organic light-emitting device.
The arylamine derivatives can be applied to organic light-emitting devices and can be used as covering layer materials, and the organic light-emitting devices prepared from the arylamine derivatives have the advantages of good light-emitting efficiency and long service life.
Drawings
FIG. 1 is a drawing showing Compound 1 of the present invention1H NMR chart; FIG. 2 is a drawing showing Compound 12 of the present invention1H NMR chart;
FIG. 3 is a drawing of Compound 21 of the present invention1H NMR chart; FIG. 4 shows a scheme for preparing compound 129 of the present invention1H NMR chart;
FIG. 5 is a drawing of inventive Compound 1441H NMR chart; FIG. 6 shows a scheme for preparing compound 146 according to the invention1H NMR chart;
FIG. 7 shows a scheme for preparing a compound 161 of the present invention1H NMR chart.
Detailed Description
The following will clearly and completely describe the technical solutions of 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 embodiments. 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 scope of protection of the present invention.
The alkyl refers to a hydrocarbon group formed by subtracting one hydrogen atom from alkane molecules, and can be a straight-chain alkyl group, a branched-chain alkyl group or a cyclic alkyl group. The straight chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but is not limited thereto; the branched alkyl group includes, but is not limited to, an isomeric group of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, etc.; the cycloalkyl group includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., but is not limited thereto. The above alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group.
The linear alkyl group having more than two carbon atoms such as propyl, butyl, pentyl, etc. described in the present invention includes isomers thereof, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, etc., but is not limited thereto.
The aryl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be monocyclic aryl group, polycyclic aryl group or condensed ring aryl group, and examples may include phenyl group, biphenyl group, terphenyl group, naphthyl group, binaphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, fluorenyl group, spirobifluorenyl group, chrysenyl group, fluoranthenyl group, benzofluorenyl group, naphthofluorenyl group, benzofluoranthenyl group and the like, but are not limited thereto.
The heteroaryl group of the present invention is a general term in which one hydrogen atom is removed from a nuclear carbon of an aromatic heterocyclic ring composed of carbon and a hetero atom including, but not limited to, oxygen, sulfur and nitrogen atoms, leaving a monovalent group, and may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group, and examples may include carbazolyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidinyl, triazinyl, acridinyl, phenazinyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, phenoxazinyl, phenothiazinyl, phenoxathiin, quinazolinyl, quinoxalinyl, quinolyl, isoquinolyl, purinyl, indolyl, azacarbazolyl, etc, Azafluorenyl, azaspirobifluorenyl, xanthenyl, thioxanthyl, and the like, but are not limited thereto.
The "C6 to C30" in the "substituted or unsubstituted aryl group having C6 to C30" in the present invention means the number of carbon atoms contained in the unsubstituted aryl group, and the number of carbon atoms of the substituent is not included; "C3 to C30" in "substituted or unsubstituted heteroaryl group of C3 to C30" means the number of carbon atoms contained in the unsubstituted heteroaryl group, and the number of carbon atoms of the substituent is not included; "C6 to C18" in the "substituted or unsubstituted arylene group having C6 to C18" means the number of carbon atoms contained in the unsubstituted arylene group, and the number of carbon atoms of the substituent is not included; "C3 to C18" in "substituted or unsubstituted C3 to C18 heteroarylene" means the number of carbon atoms contained in the unsubstituted heteroarylene, and the number of carbon atoms of a substituent is not included; "C1 to C15" in the "substituted or unsubstituted alkyl group having C1 to C15" means the number of carbon atoms contained in the unsubstituted alkyl group, and the number of carbon atoms of the substituent is not included. And so on.
The term "substituted or unsubstituted" as used herein means that the group is unsubstituted or mono-or polysubstituted with groups independently selected from, but not limited to, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amine, and the like, preferably with groups selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, benzophenanthrenyl, perylenyl, pyrenyl, benzyl, fluorenyl, 9-dimethylfluorenyl, dianilinyl, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, and the like, Phenoxazinyl, indolyl and the like are not limited to those groups which are mono-or polysubstituted.
The invention provides an arylamine derivative, which is represented by a formula I,
Figure BDA0002317993110000051
wherein R is1、R2To form a substituted or unsubstituted seven-membered ring, a substituted or unsubstituted six-membered ring;
Ar1、Ar2、Ar3independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C3-C24 heteroaryl;
wherein Ar is1、Ar2、Ar3At least one is a group of formula I-a:
Figure BDA0002317993110000052
wherein, the ring A is selected from any one of groups shown in 1a to 1 d:
Figure BDA0002317993110000053
"" is the position of attachment of the group;
Z1selected from O, S, N-R1Wherein R is1Is phenyl, Z2Is selected from N;
R0one selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, acridinyl, phenanthryl, triphenylene, phenoxazinyl, phenothiazinyl, phenoxathinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, thienyl, furyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, benzodibenzofuryl, and benzo 9, 9-dimethylfluorenyl, n is an integer of 0 to 4;
L0one kind selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein the substituent is selected from one or more of methyl, ethyl, isopropyl, tertiary butyl, phenyl;
l is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirofluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.
Preferably, R1、R2Taken together with the atoms to which they are attached to form a substituted or unsubstituted seven-membered ring, a substituted or unsubstituted six-membered ring means R1、R2Linked together to form a substituted or unsubstituted alkylene group.
Preferably, the formula I is selected from one of the following formulas II and III:
Figure BDA0002317993110000061
preferably, Ar is1、Ar2、Ar3Independently selected from the group consisting of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazine, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxathiyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted naphthofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, quinoxalinyl, quinonyl, quino, Substituted or unsubstituted purinyl, substituted or unsubstituted indolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl.
Preferably, L is selected from any one of the following groups:
Figure BDA0002317993110000062
wherein, X2Selected from O, S, N-R3Wherein R is3One selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl;
r is selected from one of H, methyl, ethyl, isopropyl and tert-butyl, and k is an integer from 0 to 4;
R1one selected from H, methyl, phenyl, tolyl, biphenyl and naphthyl;
p is an integer of 0 to 2.
Preferably, the group of formula I-a is selected from the group of formula V shown below:
Figure BDA0002317993110000071
wherein, ring A is selected from the group shown as 1a or 1 b:
Figure BDA0002317993110000072
"" is the position of attachment of the group;
wherein Z is1Selected from O, S, N-R1Wherein R is1Is phenyl;
R0one selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, acridinyl, phenanthryl, triphenylene, phenoxazinyl, phenothiazinyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, dibenzofuranyl, and n is an integer of 0 to 4;
L0is selected from one of phenylene, naphthylene and tolylene.
Preferably, the group of formula I-a is selected from one of the following groups V-1 to V-14:
Figure BDA0002317993110000073
preferably, in formula I, Ar1、Ar2、Ar3Wherein the groups other than formula i-a are each independently selected from one of the groups shown below:
Figure BDA0002317993110000081
wherein R is12One selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl;
R13one selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiin, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, quinolyl, isoquinolyl, indolyl, pyridyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl;
X1one selected from O, S, Se;
L1one selected from the group consisting of formulas (1) to (14):
Figure BDA0002317993110000082
m is an integer of 0 to 2;
a is an integer of 0 to 3;
c is an integer of 0 to 4;
b is an integer of 0 to 5;
d is an integer of 0 to 7;
f is an integer of 0 to 9;
l is selected from one of the following groups:
Figure BDA0002317993110000091
preferably, in formula I, Ar1、Ar2、Ar3Wherein the groups other than formula i-a are each independently selected from one of the groups shown below:
Figure BDA0002317993110000101
preferably, the arylamine derivative is selected from one of the following chemical structures:
Figure BDA0002317993110000111
Figure BDA0002317993110000121
Figure BDA0002317993110000131
Figure BDA0002317993110000151
Figure BDA0002317993110000161
the arylamine derivative disclosed by the formula I is obtained through the following synthetic route:
case 1: when L is a single bond:
Figure BDA0002317993110000171
case 2: when L is not a single bond:
Figure BDA0002317993110000172
the intermediate product and the arylamine derivative shown in the chemical formula I can be obtained through a Buchwald reaction and a Suzuki coupling reaction.
The sources of the raw materials used in the above reactions are not particularly limited, and the aromatic amine derivatives of the present invention can be obtained by using commercially available raw materials or by using preparation methods known to those skilled in the art. The present invention has no special limitation on the above reaction, and the preparation method is simple and easy to operate by adopting the conventional reaction well known by the technical personnel in the field.
The invention also provides an organic light-emitting device which comprises a cathode, an anode and one or more organic layers, wherein the organic layers comprise at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer which are arranged between the two electrodes, and/or a covering layer arranged outside the two electrodes; at least one layer of the organic layers contains any one or the combination of at least two of the aromatic amine derivatives.
Preferably, the organic layer of the present invention includes a capping layer, and the capping layer contains any one or a combination of at least two of any one of the arylamine derivatives of the present invention.
Preferably, the cover layer is located on a side of the cathode facing away from the anode.
The light emitting device of the present invention is generally formed on a substrate. The substrate may be any substrate that does not change when an electrode or an organic layer is formed, for example, a substrate made of glass, plastic, a polymer film, or silicon. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.
In the light-emitting device of the present invention, at least one of the anode and the cathode is transparent or translucent, and preferably, the cathode is transparent or translucent.
As the anode material, a conductive metal oxide film, a translucent metal thin film, or the like is generally used. Examples of the method for producing the film include a film (NESA or the like) made of a conductive inorganic compound containing indium oxide, zinc oxide, tin oxide, and a composite thereof, such as indium tin oxide (abbreviated as ITO) or indium zinc oxide (abbreviated as IZO), and a method using gold, platinum, silver, copper, or the like. As the anode, an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof, or the like can be used. The anode may have a laminate structure of 2 or more layers, and preferably, the anode of the present invention is formed of an opaque ITO-Ag-ITO substrate.
The hole injection layer is to improve the efficiency of hole injection from the anode into the hole transport layer and the light emitting layer. The hole injection material of the present invention may be a metal oxide such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, or titanium oxide, or a low molecular weight organic compound such as a phthalocyanine-based compound or a polycyano group-containing conjugated organic material, but is not limited thereto. Preferably, the hole injection layer of the present invention is selected from 4,4 '-tris [ 2-naphthylphenylamino ] triphenylamine (abbreviated as 2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylamine (abbreviated as HAT-CN), 4' -tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), 4 '-tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), copper (II) phthalocyanine (abbreviated as CuPc), N' -bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N, N '-diphenyl-biphenyl-4, 4' -diamine (abbreviated as DNTPD), etc., it may be a single structure made of a single substance, or a single-layer structure or a multi-layer structure made of different substances.
The hole transport layer of the present invention is preferably a single-layer structure composed of a single layer of a material having a good hole transport property, and may be selected from, for example, aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and other small-molecule materials, poly-p-phenylene derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, and polysilane and its derivatives, but is not limited to, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), N '-di (naphthalene-1-yl) -N, N' -di (phenyl) -2,2 '-dimethylbenzidine (α -NPD), N' -diphenyl-N, N '-di (3-methylphenyl) -1,1' -biphenyl-4, 4 '-diamine (TPD), 4' -cyclohexyldi [ N, N-di (4-methylphenyl) aniline ] (tado), and other single-layer structures, such as tado-9, 7-di (phenyl) aniline).
The electron blocking layer is a layer which transports holes and blocks electrons, and is preferably selected from N, N ' -bis (naphthalene-1-yl) -N, N ' -bis (phenyl) -2,2' -dimethylbenzidine (abbreviated as α -NPD), 4',4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (abbreviated as TPD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (abbreviated as TAPC), 2,7, 7-tetrakis (diphenylamino) -9, 9-spirobifluorene (abbreviated as Spiro-TAD), and the like, and may be a single structure composed of a single substance or a single-layer structure or a multilayer structure composed of different substances.
The light-emitting layer material includes a light-emitting layer host material AND a light-emitting layer guest material, AND preferably, the host material is selected from 4,4' -bis (9-Carbazole) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), N ' -bis- (1-naphthyl) -N, N ' -diphenyl- [1,1':4',1 ″:4 ″,1 "' -tetrabiphenyl ] -4, 4" ' -diamino (4P-NPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), AND the like, AND may be a single layer structure or a multilayer structure formed by a single layer or multiple layers.
The guest material of the light-emitting layer of the present invention may include one material or a mixture of two or more materials, and the light-emitting material is classified into a blue light-emitting material, a green light-emitting material, and a red light-emitting material. Preferably, the luminescent material of the present invention is a blue luminescent material, and the object of the blue luminescent layer is selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA for short), 2,5,8, 11-tetra-tert-butylperylene (TBPe for short), 4' -bis [4- (diphenylamino) styryl ] perylene]Biphenyl (BDAVBi for short), 4' -di [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi for short), bis (2-hydroxyphenyl pyridine) beryllium(abbreviation: Bepp)2) Bis (4, 6-difluorophenylpyridine-C2, N) picolinoyiridium (FIrpic).
The doping ratio of the host material and the guest material of the light-emitting layer is preferably varied depending on the materials used, and the doping film thickness ratio of the guest material of the light-emitting layer is usually 0.01 to 20%, preferably 0.1 to 15%, more preferably 1 to 10%.
The hole blocking layer is a layer that transports electrons and blocks holes, and is preferably selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (abbreviated as BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (abbreviated as TPBi), and tris (8-hydroxyquinoline) aluminum (III) (abbreviated as Alq)3) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), and the like, which may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure composed of different substances.
The electron transport layer is a layer having a function of transporting electrons. The electron transport material of the present invention may be selected from known oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives, and preferably, the electron transport layer is selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), and tris (8-hydroxyquinoline) aluminum (III) (Alq)3) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), and the like, which may be a single structure composed of a single substance or a single-layer structure or a multi-layer structure composed of different substances.
The electron injection layer is to improve the efficiency of electron injection from the cathode into the electron transport layer and the light emitting layer. The electron injection material of the present invention may Be Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, lithium fluoride, sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, magnesium fluoride, calcium fluoride, lithium oxide, cesium carbonate, lithium acetate, sodium acetate, potassium acetate, lithium tetrakis (8-quinolinolato) boron, lithium 8-quinolinolato, or the like, and may Be a single structure formed of a single substance or a single-layer structure or a multi-layer structure formed of different substances. Preferably, the electron injection layer according to the present invention may be selected from LiF.
As the cathode material, a metal material having a small work function is generally preferred. For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like, alloys of 2 or more of these metals, or alloys of 1 or more of these metals and 1 or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or graphite intercalation compounds, and the like can be used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The cathode may have a laminated structure of 2 or more layers. Preferably, the cathode of the invention uses Ag or Mg-Ag alloy or thin Al.
Preferably, the covering layer of the present invention is selected from any one or a combination of at least two of any one of the aromatic amine derivatives described in the present invention or from Alq3。
The film thicknesses of the hole transporting layer and the electron transporting layer may be selected as appropriate depending on the materials used, and may be selected so as to achieve appropriate values of the driving voltage and the light emission efficiency. Therefore, the film thicknesses of the hole transporting layer and the electron transporting layer are, for example, 1nm to 1um, preferably 2nm to 500nm, and more preferably 5nm to 200 nm.
The order and number of layers to be stacked and the thickness of each layer can be appropriately selected in consideration of the light emission efficiency and the lifetime of the device.
The arylamine derivative and the organic light-emitting device thereof have the following preferable structures: substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer. However, the structure of the organic light emitting device is not limited thereto. The arylamine derivatives and the organic light-emitting devices thereof can be selected and combined according to the parameter requirements of the devices and the characteristics of materials, and part of organic layers can be added or omitted.
The method for forming each layer in the organic light-emitting device is not particularly limited, and any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray, slit coating, and dip coating may be used, and in the present invention, vacuum evaporation is preferably used.
The organic light-emitting device can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lamps and the like.
The invention is explained in more detail by the following examples, without wishing to restrict the invention accordingly. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other derivatives and devices according to the invention within the full scope of the disclosure without undue inventive effort.
Preparation and characterization of the Compounds
Description of raw materials, reagents and characterization equipment:
the raw materials used in the following examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art.
The mass spectrum was analyzed by matrix-assisted laser desorption ionization (AXIMA-CFR plus) from Kratos Analytical, Inc. of Shimadzu corporation, U.K., using chloroform as a solvent;
the element analysis uses a Vario EL cube type organic element analyzer of Germany Elementar company, and the mass of a sample is 5-10 mg;
nuclear magnetic resonance (1H NMR Spectroscopy) A nuclear magnetic resonance spectrometer model Bruker-510 (Bruker, Germany), 600MHz, CDCl3Or DMSO is used as solvent and TMS is used as internal standard.
[ Synthesis example 1] Synthesis of Compound 1
Figure BDA0002317993110000211
Synthesis of intermediate 1-1
Under nitrogen protection, 3-chloroiminodibenzyl (18.83g, 0.082mol), compound 2- (4-bromophenyl) benzoxazole (24.08g, 0.083mol), cuprous iodide (7.8g, 0.041mol), ethylenediamine (2.8mL, 0.041mol) and cesium carbonate (80g, 0.246mol) were weighed and added to toluene (250mL) in the order described above with reflux stirring. Extraction with ethyl acetate the vacuum distillation, passage of dichloromethane and hexane through the column gave intermediate 1-1(28.78g, 83%). The purity of the solid is not less than 99.3 percent by HPLC detection.
Synthesis of intermediate 1-2
To a 1L reaction flask, toluene (600mL), 4- (2-benzoxazolyl) aniline (44.15g, 0.21mol), 1-bromobenzene (32.97g, 0.21mol), palladium acetate (0.61g, 0.0027mol), sodium tert-butoxide (33.7g, 0.351mol), and tri-tert-butylphosphine (10.8mL of a 1.0M solution in toluene, 0.0108mol) were added in that order under nitrogen. And reacted under reflux for 2 hours. After the reaction is stopped, the mixture is cooled to room temperature, filtered by kieselguhr, the filtrate is concentrated, recrystallized by methanol, filtered by suction and rinsed by methanol to obtain a recrystallized solid, and the intermediate 1-2(53.51g, the yield is about 89%) is obtained, and the purity of the solid is not less than 98.4% by HPLC (high performance liquid chromatography).
Synthesis of intermediates 1 to 3
Under nitrogen protection, a toluene solvent (450ml), 4-bromobenzeneboronic acid (7.23g, 36mmol), intermediate 1-2(11.45g, 40mmol), and Pd were added to a 1L reaction flask in this order2(dba)3(990mg, 1.08mmol), BINAP (1.65g, 16.5mmol) and sodium tert-butoxide (9.9g, 100.8mmol), were dissolved with stirring and reacted under reflux under nitrogen for 24 hours, after completion of the reaction, the reaction solution was washed with dichloromethane and distilled water and extracted by separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, followed by washing with cyclohexane: separating, purifying and refining ethyl acetate 10:1 by column chromatography as eluentFinally obtaining the solid intermediate 1-3(20.76g, the yield is 77%), and the solid purity is not less than 99.1% by HPLC detection.
Synthesis of Compound 1
To a 1L reaction flask were added, under nitrogen, intermediate 1-3(20.31g, 50mmol), intermediate 1-1(21.14g, 50mmol), palladium tetrakistriphenylphosphine (1.15g, 1mmol) and sodium carbonate (41.4g, 300mmol) in that order, and the weighed reactants were dissolved in a solvent of toluene (1L)/EtOH (200 mL)/distilled water (200mL) and heated at 90 ℃ for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue was filtered through silica gel and recrystallized. Compound 1(29.21g, 78% yield) was obtained, and the solid purity ≧ 98.9% by HPLC.
Mass spectrum m/z: 748.29 (calculated value: 748.28). Theoretical element content (%) C52H36N4O2: c, 83.40; h, 4.85; n, 7.48; o, 4.27 measured elemental content (%): c, 83.42; h, 4.86; n, 7.46; and O, 4.26.1H NMR (600MHz, DMSO) (delta, ppm): 8.10-8.07 (m,2H),7.99(d,2H),7.81(d,1H),7.75(td,4H), 7.72-7.68 (m,2H),7.67(dd,1H), 7.56-7.53 (m,1H),7.47(d,1H), 7.45-7.42 (m,3H), 7.40-7.37 (m,3H), 7.37-7.32 (m,3H),7.24(t,5H), 7.13-7.08 (m,2H), 6.71-6.68 (m,2H),3.32(s, 4H). The above results confirmed that the obtained product was the objective product.
Synthesis example 2 Synthesis of Compound 12
Figure BDA0002317993110000221
The 4-bromobenzeneboronic acid in synthesis example 1 was replaced with the equimolar e-12 in the same manner as in the previous step to obtain compound 12(36.33g, yield: about 84%) with a solid purity ≧ 99.0% by HPLC.
Mass spectrum m/z: 864.39 (calculated value: 864.35). Theoretical element content (%) C61H44N4O2: c, 84.70; h, 5.13; n, 6.48; o, 3.70 measured elemental content (%): c, 84.70;H，5.14；N，6.47；O，3.70。1h NMR (600MHz, DMSO) (delta, ppm): 7.96(d,1H),7.93(d,1H), 7.89-7.85 (m,2H), 7.83-7.78 (m,3H),7.75(d,1H), 7.66-7.62 (m,5H), 7.60-7.56 (m,2H),7.43(d,1H), 7.40-7.33 (m,7H),7.26(dd,1H), 7.25-7.22 (m,1H),7.20(dd, 1H),7.15(dd,1H),7.13(d,1H),7.08(dd,2H),7.03-6.98(m,2H),6.96(dd,1H),6.81(td,1H),3.07(s,4H),1.67(d, 6H). The above results confirmed that the obtained product was the objective product.
[ Synthesis example 3] Synthesis of Compound 21
Figure BDA0002317993110000222
The 4-bromobenzeneboronic acid in synthesis example 1 was replaced with the equimolar e-21 in the same manner as in the previous step to obtain compound 21(34.82g, yield about 83%) with a solid purity of 99.2% or higher by HPLC.
Mass spectrum m/z: 838.30 (calculated value: 838.29). Theoretical element content (%) C58H38N4O3: c, 83.04; h, 4.57; n, 6.68; o, 5.72 measured elemental content (%): c, 83.05; h, 4.58; n, 6.67; and O, 5.71.1H NMR (600MHz, DMSO) (delta, ppm): 8.09(d,1H),8.03(d,1H), 7.90-7.85 (m,3H), 7.84-7.80 (m,2H),7.72(d,1H),7.70(d,1H),7.64(dd,4H), 7.62-7.57 (m,3H),7.41(d,1H), 7.40-7.37 (m,6H), 7.26-7.21 (m,3H), 7.17-7.12 (m,2H), 7.10-7.06 (m,2H),7.03-6.98(m,2H),6.96(dd,1H),6.81(td,1H),3.07(s, 4H). The above results confirmed that the obtained product was the objective product.
Synthesis example 4 Synthesis of Compound 129
Figure BDA0002317993110000231
The same procedures were repeated except for changing 2- ((4-bromophenyl)) benzoxazole in synthesis example 1 to b-129 in an equimolar amount and changing 1-bromobenzene in synthesis example 1 to 2-bromonaphthalene in an equimolar amount to obtain 129(37.96g, yield about 80%) as a compound having a purity of 99.5% by HPLC.
Mass spectrum m/z: 948.42 (calculated value: 948.39). Theoretical element content (%)C68H48N6: c, 86.05; h, 5.10; n, 8.85 measured elemental content (%): c, 86.06; h, 5.10; n, 8.84.1H NMR (600MHz, DMSO) (delta, ppm): 9.98-9.94 (m,2H), 8.76-8.67 (m,2H),8.54(dd,1H), 8.41-8.38 (m,2H),8.37(dd,1H),7.81(dd,2H),7.79(d,1H),7.78-7.76(d,2H), 7.72-7.70 (m,1H), 7.70-7.66 (m,4H), 7.66-7.60 (m,6H), 7.60-7.57 (m,2H),7.53(td,2H), 7.51-7.46 (m,7H),7.44(td,2H), 7.32-7.24 (m,3H),6.81(td,1H), 6.39-6.28 (m,2H),6.04(dd,1H), 4.07(s). The above results confirmed that the obtained product was the objective product.
Synthesis example 5 Synthesis of Compound 144
Figure BDA0002317993110000232
The intermediate 1-2 in synthesis example 1 was replaced with equimolar bis (4-biphenylyl) amine, and the same procedure was followed to give compound 144(34.48g, yield about 88%) with a solid purity of 99.8% or more by HPLC.
Mass spectrum m/z: 783.35 (calculated value: 783.32). Theoretical element content (%) C57H41N3O: c, 87.33; h, 5.27; n, 5.36; o, 2.04 measured elemental content (%): c, 87.34; h, 5.28; n, 5.35; and O, 2.03.1H NMR(600MHz,CDCl3) (δ, ppm): 8.07-8.05 (m,2H),7.74(dd,2H), 7.68-7.61 (m,4H), 7.58-7.56 (m,6H), 7.54-7.50 (m,1H), 7.48-7.46 (m,4H), 7.39-7.34 (m,6H), 7.32-7.29 (m,6H), 7.25-7.20 (m,4H), 6.80-6.82 (m,2H),3.10(s, 4H). The above results confirmed that the obtained product was the objective product.
[ Synthesis example 6] Synthesis of Compound 146
Figure BDA0002317993110000241
The 3-chloroiminodibenzyl of synthesis example 1 was replaced with equimolar a-146, and the other steps were repeated in the same manner to give 146(32.81g, yield about 86%) as a solid having a purity of 99.2% or more by HPLC.
Mass spectrum m/z: 762.35 (calculated value: 762.30). Theory of the inventionElement content (%) C53H38N4O2: c, 83.44; h, 5.02; n, 7.34; o, 4.19 measured elemental content (%): c, 83.45; h, 5.01; n, 7.35; and O, 4.18.1H NMR(600MHz,CDCl3) (δ, ppm): 7.89-7.86 (m,2H), 7.82-7.78 (m,2H),7.70(d,1H),7.64(dd,4H), 7.60-7.57 (m,2H), 7.47-7.44 (m,2H), 7.41-7.39 (m,2H),7.39(s,1H),7.38(d,2H),7.37(s,1H),7.36(d,2H),7.35(d,2H),7.24(t,2H),7.16(d,1H),7.08(ddd,3H), 7.01-6.95 (m,3H),1.74(s,3H),1.72(s, 3H). The above results confirmed that the obtained product was the objective product.
[ Synthesis example 7] Synthesis of Compound 161
Figure BDA0002317993110000251
Step3 in Synthesis example 1 was removed, and the same procedure was repeated to give compound 161(27.25g, yield: 81%) having a solid purity ≧ 98.9% by HPLC.
Mass spectrum m/z: 672.25 (calculated: 672.. 20). Theoretical element content (%) C46H32N4O2: c, 82.12; h, 4.79; n, 8.33; o, 4.76 measured elemental content (%): c, 82.13; h, 4.78; n, 8.32; o, 4.77.1H NMR (600MHz, DMSO) (delta, ppm): 8.12-8.07 (m,2H), 7.99-7.95 (m,2H), 7.77-7.73 (m,2H),7.71(tt,2H), 7.50-7.45 (m,2H), 7.45-7.42 (m,2H),7.38(dd,3H), 7.37-7.36 (m,2H), 7.36-7.34 (m,2H), 7.26-7.23 (m,2H), 7.22-7.18 (m,2H), 7.18-7.14 (m,2H),7.10(dd,1H), 6.67-6.62 (m,2H),3.32(s, 4H). The above results confirmed that the obtained product was the objective product.
The arylamine compound is used as a CPL layer material in an organic light-emitting device, and the Tg temperature is measured by the American TA company, the model number: the 25 type differential scanning calorimeter tests that the test atmosphere is nitrogen, the flowrate of the nitrogen is 50 ml/min; the heating rate is 10 ℃/min; the scanning range is 50-350 ℃; the mass of the compound sample is 1-6 mg. Refractive index (n) was measured by j.a.woollam, usa, model: measuring by an M-2000 spectrum ellipsometer, wherein the measurement is in an atmospheric environment, and the scanning range of the ellipsometer is 245-1000 nm; the size of the glass substrate is 200 multiplied by 200mm, and the thickness of the material film is 20-60 nm. The arylamine compound and the prior material are respectively tested for thermal performance and refractive index, and the results are shown in the following table 1.
TABLE 1 photophysical characteristic test of light emitting device
Figure BDA0002317993110000252
Figure BDA0002317993110000261
From the above table data, the currently applied Alq is compared3TPBi and other materials and similar compounds CP-1, the arylamine compound has high refractive index, and can be applied to a covering layer of an OLED device to effectively improve the light extraction efficiency of the device, thereby improving the luminous efficiency of the organic light-emitting device.
Comparative examples 1-3 device preparation examples:
the organic light-emitting device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: and (3) putting the ITO-Ag-ITO substrate into distilled water for cleaning for 3 times, ultrasonically cleaning for 15 minutes, after the cleaning of the distilled water is finished, ultrasonically cleaning solvents such as isopropanol, acetone, methanol and the like in sequence, drying at 120 ℃, and conveying to an evaporation plating machine.
Evaporating a hole injection layer HAT-CN/50nm, a hole transport layer NPB/30nm and an evaporation main body ADN on the prepared ITO-Ag-ITO electrode in a layer-by-layer vacuum evaporation mode: doping DPAP-DPPA 5% mixed/30 nm, then evaporating an electron transport layer Alq3: liq (1:1)/30nm, an electron injection layer LiF/0.5nm, a cathode Mg-Ag (Mg: Ag doping ratio is 9:1)/20nm, and then a cover material Alq is evaporated and plated on the cathode layer3And/60 nm. And the device was sealed in a glove box, thereby preparing an organic light emitting device. After the organic light-emitting device is manufactured according to the steps, the photoelectric property of the device is measured, and the molecular structural formula of the related material is as follows:
Figure BDA0002317993110000262
[ examples 1 to 7]
Example 1: the capping layer material of the organic light-emitting device was changed to compound 1 in synthesis example 1 of the present invention.
Example 2: the capping layer material of the organic light-emitting device was changed to compound 12 in synthesis example 2 of the present invention.
Example 3: the capping layer material of the organic light-emitting device was changed to compound 21 in synthesis example 3 of the present invention.
Example 4: the material of the cap layer of the organic light-emitting device was changed to the compound 129 in synthesis example 4 of the present invention.
Example 5: the capping layer material of the organic light-emitting device was changed to the compound 144 in synthesis example 5 of the present invention. .
Example 6: the capping layer material of the organic light-emitting device was changed to the compound 146 in synthesis example 6 of the present invention.
Example 7: the capping layer material of the organic light-emitting device was changed to the compound 161 in synthesis example 7 of the present invention.
The test software, computer, K2400 digital source meter manufactured by Keithley corporation, usa, and PR788 spectral scanning luminance meter manufactured by photressearch corporation, usa were combined into a combined IVL test system to test the luminous efficiency and CIE color coordinates of the organic light emitting device. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature.
The results of the light emission characteristic test of the obtained organic light emitting device are shown in table 2. Table 2 shows the results of the test of the light emitting characteristics of the light emitting devices prepared by the compounds prepared in the examples of the present invention and the comparative materials.
Table 2 test of light emitting characteristics of light emitting device
Figure BDA0002317993110000271
The results in table 2 show that when the arylamine derivative compound provided by the invention is applied to an organic light-emitting device as a covering layer material, the light-emitting efficiency of the device can be effectively improved, and the service life of the device is prolonged.
It is obvious that the above description of the embodiments is only intended to assist the understanding of the method of the invention and its core ideas. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.

Claims (10)

1. An arylamine derivative is characterized by being represented by a formula I,
Figure FDA0002317993100000011
wherein R is1、R2Together with the atoms to which they are attached form a substituted or unsubstituted seven-membered ring, a substituted or unsubstituted six-membered ring;
Ar1、Ar2、Ar3independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C3-C24 heteroaryl;
wherein Ar is1、Ar2、Ar3At least one is a group of formula I-a:
Figure FDA0002317993100000012
wherein, the ring A is selected from any one of groups shown in 1a to 1 d:
Figure FDA0002317993100000013
"" is the position of attachment of the group;
Z1selected from O, S, N-R1Wherein R is1Is phenyl, Z2Is selected from N;
R0selected from H, methyl, ethyl, n-propyl, isopropylN-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, acridinyl, phenanthryl, triphenylene, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, thienyl, furyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, benzo 9, 9-dimethylfluorenyl, and n is an integer of 0 to 4;
L0one kind selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, wherein the substituent is selected from one or more of methyl, ethyl, isopropyl, tertiary butyl, phenyl;
l is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirofluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thienylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.
2. An aromatic amine derivative according to claim 1, wherein the formula i is selected from one of the following formulae ii and iii:
Figure FDA0002317993100000021
3. an arylamine derivative according to claim 1 wherein Ar is Ar1、Ar2、Ar3Independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthylSubstituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxathinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted naphthofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted purinyl, substituted or unsubstituted indolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thienyl, One of substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl;
the L is selected from any one of the following groups:
Figure FDA0002317993100000022
wherein, X2Selected from O, S, N-R3Wherein R is3One selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl;
r is selected from one of H, methyl, ethyl, isopropyl and tert-butyl, and k is an integer from 0 to 4;
R1one selected from H, methyl, phenyl, tolyl, biphenyl and naphthyl;
p is an integer of 0 to 2.
4. An aromatic amine derivative according to claim 1, wherein the group of formula i-a is selected from the group of formula v as shown below:
Figure FDA0002317993100000031
wherein, ring A is selected from the group shown as 1a or 1 b:
Figure FDA0002317993100000032
"" is the position of attachment of the group;
wherein Z is1Selected from O, S, N-R1Wherein R is1Is phenyl;
R0one selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, acridinyl, phenanthryl, triphenylene, phenoxazinyl, phenothiazinyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, dibenzofuranyl, and n is an integer of 0 to 4;
L0is selected from one of phenylene, naphthylene and tolylene.
5. The aromatic amine derivative of claim 1, wherein the group of formula i-a is selected from one of the following groups v-1 to v-14:
Figure FDA0002317993100000033
6. an arylamine derivative according to claim 1 wherein in formula i, Ar is1、Ar2、Ar3Wherein the groups other than formula i-a are each independently selected from one of the groups shown below:
Figure FDA0002317993100000041
wherein R is12One selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl;
R13one selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiin, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, quinolyl, isoquinolyl, indolyl, pyridyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl;
X1one selected from O, S, Se;
L1one selected from the group consisting of formulas (1) to (14):
Figure FDA0002317993100000042
m is an integer of 0 to 2;
a is an integer of 0 to 3;
c is an integer of 0 to 4;
b is an integer of 0 to 5;
d is an integer of 0 to 7;
f is an integer of 0 to 9;
l is selected from one of the following groups:
Figure FDA0002317993100000051
7. an arylamine derivative according to claim 1 wherein in formula i, Ar is1、Ar2、Ar3Wherein the groups other than formula i-a are each independently selected from one of the groups shown below:
Figure FDA0002317993100000061
8. an aromatic amine derivative according to claim 1, wherein the aromatic amine derivative is selected from one of the following chemical structures:
Figure FDA0002317993100000071
Figure FDA0002317993100000081
Figure FDA0002317993100000091
Figure FDA0002317993100000101
Figure FDA0002317993100000111
Figure FDA0002317993100000121
9. an organic light emitting device comprising a cathode, an anode and one or more organic layers, wherein the organic layers comprise at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and/or a capping layer disposed between the two electrodes; at least one of the organic layers contains any one or a combination of at least two of the arylamine derivatives described in any one of claims 1 to 8.
10. An organic light-emitting device according to claim 9, wherein the organic layer comprises a capping layer containing any one or a combination of at least two of the aromatic amine derivatives as set forth in any one of claims 1 to 8.
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