CN114685288B - Polycyclic aromatic amine organic compound and use thereof - Google Patents

Polycyclic aromatic amine organic compound and use thereof Download PDF

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CN114685288B
CN114685288B CN202011561295.1A CN202011561295A CN114685288B CN 114685288 B CN114685288 B CN 114685288B CN 202011561295 A CN202011561295 A CN 202011561295A CN 114685288 B CN114685288 B CN 114685288B
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CN114685288A (en
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李涛
龙志飞
龙芷君
宋晶尧
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Abstract

The invention relates to a polycyclic aromatic amine organic compound, which is shown as a general formula (1), wherein Z is selected from the group consisting of nonexistence, single bond, O and S; m is selected from 0 or 1, n is selected from 0 or 1, and m+n is more than or equal to 1; ar (Ar) 1 ～Ar 8 Each occurrence is independently selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 3 to 30 ring atoms; l (L) 1 、L 2 Each occurrence is independently selected from a single bond, a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 30 ring atoms. The invention also relates to a mixture, a composition and an organic electronic device comprising the polycyclic aromatic amine organic compound.

Description

Polycyclic aromatic amine organic compound and use thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a polycyclic aromatic amine organic compound and application thereof.
Background
The organic electroluminescent display device is a self-luminous display device, which generates excitons by transfer and recombination of carriers between functional layers, and emits light by means of organic compounds or metal complexes having high quantum efficiency. The organic electroluminescent element generally has a positive electrode and a negative electrode and an organic functional layer structure therebetween. In order to improve the efficiency and lifetime of the organic electroluminescent device, the organic functional layers have a multi-layered structure, each layer containing a different organic material. Specifically, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like may be included. In such an organic electroluminescent element, when a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic functional layer, electrons are injected from a negative electrode into the organic functional layer, and when the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to a ground state. The organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast ratio and the like.
In recent years, the luminous efficiency of organic electroluminescent diodes (OLEDs) has been greatly improved, but the internal quantum efficiency thereof has been approaching the theoretical limit. The difference in mobility of holes and electrons causes that the recombination region is not completely uniformly dispersed in the light emitting layer, reducing the light emitting efficiency of the device.
Therefore, how to design new materials with better performance to achieve the best device results has been a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention aims to provide a polycyclic aromatic amine-type organic compound, a mixture containing the same, a composition, an organic electronic device and application thereof, and aims to provide a novel electron blocking layer material, which improves the luminous efficiency and the service life of the device.
In one aspect of the present invention, there is provided a polycyclic aromatic amine-based organic compound represented by the general formula (1):
wherein Z is selected from the group consisting of absent, single bond, O, or S;
m is selected from 0 or 1, n is selected from 0 or 1, and m+n is more than or equal to 1;
Ar 1 ～Ar 8 independently selected from substituted or unsubstitutedAn aromatic group having 6 to 30 ring atoms substituted or a heteroaromatic group having 5 to 30 ring atoms substituted or unsubstituted;
L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms.
In another aspect of the present invention, there is provided a mixture comprising at least one of the organic compounds, and at least one organic functional material selected from the group consisting of a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, an organic light emitting guest material, an organic host material, and inorganic quantum dots.
The invention further provides a composition comprising at least one of said organic compounds or said mixtures, and at least one organic solvent.
The invention further provides an organic electronic device comprising or being prepared from at least one of said organic compound or said mixture.
Compared with the prior art, the invention has the following beneficial effects:
according to the organic compound disclosed by the invention, a large steric hindrance group is introduced into a conjugated aromatic amine structure, so that conjugation in molecules is reduced, the conjugated aromatic amine structure has a high triplet state energy level T1 and a shallow LUMO energy level, electrons of a light-emitting layer are prevented from being transferred to a hole-transporting layer, and therefore, the light-emitting excitons are limited in the light-emitting layer, and the light-emitting efficiency of a device is improved. The organic compound can be used as an electron blocking material, and can improve the luminous efficiency and the service life of an electroluminescent device by being matched with a proper hole transport material and a luminous material. A solution for a light emitting device with high efficiency and long lifetime is provided.
Detailed Description
The technical scheme of the invention is further described in detail below with reference to specific embodiments. The present invention may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.
The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
In the present invention, "substituted" means that a hydrogen atom in a substituted group is substituted by a substituent.
In the present invention, the same substituent may be independently selected from different groups when it appears multiple times. Containing a plurality of R as shown in the general formula 1 R is then 1 May be independently selected from different groups.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood to be optionally substituted with groups acceptable in the art, including but not limited to: deuterium atom, cyano group, isocyano group, nitro group, halogen atom, C 1-10 Alkyl, C of (2) 1-10 Alkoxy, C 1-10 Alkylthio, C 6-30 Aryl, C of (2) 6-30 Aryloxy group, C 6-30 Arylthio radicals C 3-30 Heteroaryl of (C) 1-30 Silane group, C of (C) 2-10 Alkylamino, C 6-30 Or combinations of the foregoing groups, and the like.
In the present invention, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
In the present invention, "alkyl" may denote a linear, branched and/or cyclic alkyl group. Alkyl (C)The carbon number of the radicals may be from 1 to 50, from 1 to 30, from 1 to 20, from 1 to 10 or from 1 to 6. Phrases containing this term, e.g., "C 1-9 Alkyl "means an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be, independently of the other, C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9 An alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantane, and the like.
"aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removal of one hydrogen atom, which may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for a polycyclic species. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzophenanthrene, perylene, naphthacene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9, 9-diaryl fluorene, triarylamine, diaryl ether systems in particular should also be included in the definition of aryl groups.
"heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, which may be an N atom, an O atom, an S atom, or the like. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted, suitable examples include, but are not limited to: triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, naphthyridine, quinoxaline, phenanthridine, primary pyridine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole, and derivatives thereof.
"amine group" refers to a derivative of an amine having the formula-N (X) 2 Wherein each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or the like. Non-limiting types of amine groups include-NH 2 -N (alkyl) 2 -NH (alkyl), -N (cycloalkyl) 2 -NH (cycloalkyl), -N (heterocyclyl) 2 -NH (heterocyclyl), -N (aryl) 2 -NH (aryl), -N (alkyl) (heterocyclyl), -N (cycloalkyl) (heterocyclyl), -N (aryl) (heteroaryl), -N (alkyl) (heteroaryl), and the like.
In the present invention "×" attached to a single bond represents a linking or fusing site.
In the present invention, when no linking site is specified in the group, an optionally-ligatable site in the group is represented as a linking site;
in the present invention, when no condensed site is specified in the group, it means that an optionally condensed site in the group is used as a condensed site, and preferably two or more sites in the group at ortho positions are condensed sites;
in the present invention, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.gR in (C) is connected with any substitutable site of benzene ring.
In the present invention, "adjacent group" means that there is no substitutable site between two substituents.
The invention provides a polycyclic aromatic amine organic compound, which is shown in the following general formula (1):
wherein Z is selected from the group consisting of absent, single bond, O, or S;
m is selected from 0 or 1, n is selected from 0 or 1, and m+n is more than or equal to 1;
Ar 1 ～Ar 8 each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 ring atoms or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;
L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms.
In one embodiment, ar 1 ～Ar 8 Each occurrence is independently selected from a substituted or unsubstituted aromatic group having 6 to 13 ring atoms or a substituted or unsubstituted heteroaromatic group having 5 to 13 ring atoms;
in the present invention, the substitution is preferably selected from C 1-10 Or aryl or heteroaryl having 6 to 13 ring atoms.
In one embodiment, m+n=1; further, m is selected from 1 or n is selected from 1.
In some alternative embodiments, ar 1 ～Ar 8 Each independently selected from any one of the following groups:
wherein X isEach occurrence is independently selected from CR 1 Or N; preferably, X is selected from CR 1 ；
Y is selected from O, S, NR 2 Or CR (CR) 2 R 3 ；
R 1 、R 2 、R 3 Each occurrence is independently selected from H, D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a keto group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate or isothiocyanate, hydroxy, nitro, CF3, cl, br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 30 ring atoms, or an aryloxy or heteroaromatic group having 5 to 30 ring atoms, or a combination of these systems.
In one embodiment, ar 5 -Ar 8 Each independently selected from (B-1) or (B-2) or (B-3).
In some preferred embodiments, ar 7 、Ar 8 Each independently selected from any one of the following groups:
wherein, represents a linking site, and the H atom on the ring may be further substituted by R 1 And (3) substitution.
In some embodiments, Z is a single bond, O or S, ar 5 、Ar 6 Each independently selected from any one of the following groups:
wherein the H atom on the ring may further R 1 Is substituted.
In other embodiments, Z is absent, ar 5 、Ar 6 Each independently selected from any one of the following groups:
wherein the H atom on the ring may be further replaced by R 1 And (3) substitution.
In one embodiment, ar 7 -Ar 8 Are all selected from (B-1); further, formula (1) is selected from structures represented by formula (2):
in one embodiment, ar 5 Or Ar 6 Selected from (B-1). Further, formula (1) is selected from structures represented by any one of formulas (3-1) to (3-8):
in one embodiment, Z is preferably from a single bond or absent, as: compared with the introduction of the heteroatom group, the triplet state energy level of Z selected from single bond or base in the absence is higher, and when the Z is used as an electron blocking layer, the non-radiative transition of excitons of the light emitting layer can be reduced, and the light emitting efficiency of the device is improved.
In one embodiment, R in formula (2) or formulas (3-1) - (3-8) 1 Each occurrence is independently selected from H, D, or a linear alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 20 ring atomsA fragrance group or a combination of these systems.
In one embodiment, ar 1 -Ar 4 Independently selected from (B-1) or (B-2) or (B-3) or (B-5).
In some preferred embodiments, ar 1 ～Ar 4 Each occurrence is independently selected from any one of the following groups:
in a preferred embodiment, formula (1) is selected from structures represented by any one of formulas (4-1) - (4-3):
preferably, the formula (4-1) or (4-2) or (4-3) R 1 Each occurrence is independently selected from H, D, or a linear alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 13 ring atoms, or a combination of these systems.
In some alternative embodiments, L 1 、L 2 Each occurrence is independently selected from a single bond or any of the following groups:
wherein X and Y are as defined above.
Further, L 1 、L 2 Each occurrence is independently selected from a single bond, phenyl or naphthyl, any position on the phenyl and naphthyl groups being capable of being substituted by R 1 And (3) substitution. More preferably L 1 、L 2 Each occurrence is selected from single bonds.
In one embodiment of the present invention, in one embodiment,and/or +.>Selected from the following structures:
in particular, the compounds according to the invention are preferably selected from, but not limited to, the following structures, which may be optionally substituted:
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wherein: h in the above structure may be further optionally substituted.
The polycyclic aromatic amine organic compound can be used as a functional material for electronic devices, in particular OLED devices. The functional material may be classified into a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a light emitting Guest material (Guest email), and a Host material (Host email).
In one embodiment, the polycyclic aromatic amine-based organic compound according to the present invention may be used as an electron blocking layer material or a hole transporting material.
The polycyclic aromatic amine-based organic compounds according to the present invention have a glass transition temperature Tg of greater than or equal to 100 ℃, in a preferred alternative embodiment greater than or equal to 120 ℃, and in a more preferred alternative embodiment greater than or equal to 135 ℃.
Organic Compounds according to the invention, T 1 More preferably not less than 2.3eV, still more preferably not less than 2.5eV, still more preferably not less than 2.65eV.
Further, the aromatic amine-based organic compound according to the present invention is particularly suitable as an electron blocking material for green light devices.
The invention also relates to a mixture which comprises at least one organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron injection materials, electron blocking materials, hole blocking materials, organic luminescent guest materials, host materials or inorganic quantum dots. Specific functional materials are described in detail in WO2010135519A1, US20090134784A1 and WO 2011110277A1.
It is an object of the present invention to provide a material solution for an evaporated OLED.
In certain embodiments, the organic compounds according to the invention have a molecular weight of 1100g/mol or less, preferably 1000g/mol or less, very preferably 950g/mol or less, more preferably 900g/mol or less, most preferably 800g/mol or less.
It is another object of the invention to provide a material solution for printed OLEDs.
In certain embodiments, the organic compounds according to the invention have a molecular weight of ≡700g/mol, preferably ≡900g/mol, preferably ≡1000g/mol, most preferably ≡1100g/mol.
The invention also relates to a composition comprising at least one organic compound as described above or a mixture as described, and at least one organic solvent.
The organic solvent may be selected from any one of aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, or boric acid ester or phosphoric acid ester compound, or a mixture of two or more solvents. Preferably, the organic solvent is selected from aromatic or heteroaromatic based solvents.
Examples of aromatic or heteroaromatic-based solvents suitable for the present invention are, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluenes, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenyl methane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenyl methane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenyl methane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, 2-quinolinecarboxylic acid, ethyl ester, 2-methylfuran, etc.
Examples of aromatic ketone-based solvents suitable for the present invention are, but are not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropionophenone, 3-methylpropionophenone, 2-methylpropionophenone, and the like.
Examples of aromatic ether-based solvents suitable for the present invention are, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylben-ther, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-t-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.
Examples of aliphatic ketone or aliphatic ether based solvents suitable for the present invention are, but are not limited to: 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, isophorone, di-n-amyl ketone, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
Examples of borate-based or phosphate-based solvents suitable for the present invention are, but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Particular preference is given to octyl octanoate, diethyl sebacate, diallyl phthalate and isononyl isononanoate.
The solvent may be a single component organic solvent or a mixture of two or more organic solvents.
In certain preferred embodiments, a composition according to the present invention may comprise at least one organic compound or polymer or mixture as described above, at least one organic solvent and at least one co-solvent. Examples of such co-solvents include (but are not limited to): methanol, ethanol, 2-methoxyethanol, methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane, 3-phenoxytoluene, 1-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydronaphthalene, decalin, indene and/or mixtures thereof.
In some preferred embodiments, particularly suitable solvents for the present invention are solvents having Hansen (Hansen) solubility parameters within the following ranges: δd (dispersion force) is in the range of 17.0 to 23.2MPa1/2, particularly in the range of 18.5 to 21.0MPa 1/2; δp (polar force) is in the range of 0.2 to 12.5MPa1/2, particularly in the range of 2.0 to 6.0MPa 1/2; δh (hydrogen bonding force) is in the range of 0.9 to 14.2MPa1/2, particularly in the range of 2.0 to 6.0MPa 1/2.
The composition according to the invention, wherein the organic solvent is selected taking into account its boiling point parameters. In the invention, the boiling point of the organic solvent is more than or equal to 150 ℃; preferably not less than 180 ℃; more preferably not less than 200 ℃; more preferably not less than 250 ℃; and most preferably at a temperature of 275 ℃ or more or 300 ℃ or more. Boiling points in these ranges are beneficial in preventing nozzle clogging of inkjet printheads. The organic solvent may be evaporated from the solvent system to form a film comprising the functional material.
In one embodiment, the composition according to the invention is a solution. In another embodiment, the composition according to the invention is a suspension.
The compositions according to embodiments of the present invention may comprise from 0.01 to 10% by weight of the organic compound according to the present invention or mixtures thereof, preferably from 0.1 to 15% by weight, more preferably from 0.2 to 5% by weight, most preferably from 0.25 to 3% by weight.
The invention also relates to the use of said composition as a coating or printing ink for the production of organic electronic devices, particularly preferably by printing or coating.
Suitable Printing or coating techniques include, but are not limited to, ink jet Printing, spray Printing (nozle Printing), letterpress Printing, screen Printing, dip coating, spin coating, doctor blade coating, roller Printing, twist roller Printing, lithographic Printing, flexography, rotary Printing, spray coating, brush or pad Printing, slot die coating, and the like. Gravure printing, inkjet printing and inkjet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, etc., for adjusting viscosity, film forming properties, improving adhesion, etc. The printing technology and the related requirements of the solution, such as solvent, concentration, viscosity and the like.
The invention further relates to the use of a polycyclic aromatic amine organic compound, mixture or composition as described above in an organic electronic device. In the embodiment of the invention, the organic compound is preferably used for an electron blocking layer of an OLED device.
The invention further relates to an organic electronic device comprising two electrodes, one or more organic functional layers arranged between the two electrodes, the organic functional layers comprising an arylamine organic compound, a mixture or being prepared from the above-described composition. Further, the organic electronic device comprises a cathode, an anode, and one or more organic functional layers located at the cathode and the anode.
The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL) or a light emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the emitter in the light emitting layer or of the p-type semiconductor material as HIL or HTL or Electron Blocking Layer (EBL) is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2eV. Examples of anode materials include, but are not limited to: al, cu, au, ag, mg, fe, co, ni, mn, pd, pt, ITO aluminum doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present application.
The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO or conduction band level of the light-emitting body in the light-emitting layer or of the n-type semiconductor material as an Electron Injection Layer (EIL) or Electron Transport Layer (ETL) or Hole Blocking Layer (HBL) is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. In principle, all materials which can be used as cathode of an OLED are possible as cathode materials for the device according to the invention. Examples of cathode materials include, but are not limited to: al, au, ag, ca, ba, mg, liF/Al, mgAg alloy, baF2/Al, cu, fe, co, ni, mn, pd, pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
In some embodiments, the organic electroluminescent device according to the present invention includes one or more organic functional layers, wherein the organic functional layers may be selected from one or more of an electron injection layer, an electron transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, an electron blocking layer, and a light emitting layer, and further, the organic electroluminescent device includes at least a light emitting layer, a hole transport layer, and an electron blocking layer between the light emitting layer and the hole transport layer.
In one embodiment the organic functional layer comprises at least one electron blocking layer or hole transporting layer comprising an organic compound as described above.
In some embodiments, the light emitting material in the light emitting layer is selected from a singlet light emitter, a triplet light emitter or a TADF material according to the present invention.
In some further alternative embodiments, the thickness of the organic functional layer of the organic electroluminescent device according to the present invention is generally 10nm to 200nm, preferably 20nm to 150nm, more preferably 30nm to 100nm, and most preferably 40nm to 90nm.
The organic electronic device may be selected from, but not limited to, organic Light Emitting Diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEEC), organic Field Effect Transistors (OFET), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes (Organic Plasmon Emitting Diode), etc., particularly preferred are organic electroluminescent devices such as OLEDs, OLEEC, organic light emitting field effect transistors.
The invention also relates to the use of the electroluminescent device according to the invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.
The invention also relates to an electronic device comprising an organic electronic device according to the invention, including, but not limited to, a display device, a lighting device, a light source, a sensor, etc.
The invention will be described in connection with preferred embodiments, but the invention is not limited to the embodiments described below, it being understood that the appended claims outline the scope of the invention and those skilled in the art, guided by the inventive concept, will recognize that certain changes made to the embodiments of the invention will be covered by the spirit and scope of the claims.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The synthetic methods of the compounds according to the present invention are exemplified, but the present invention is not limited to the following examples.
EXAMPLE 1 Synthesis of Compound G2
Z2 (7.75 g,25 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 18.8 mL) was slowly added. After about 0.5 hours, a solution of Z1 (8.6 g,25 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain a total of 10g of Z3, and the yield was 72%.
Compound Z3 (8.37 g,15 mmol) and Z4 (4.28 g,15 mmol) were dissolved in dry toluene and sodium tert-butoxide (1.73 g,18 mmol) and tribenzylidene propylene were addedAfter replacing nitrogen three times with ketodipalladium (0.41 g,0.45 mmol), tri-tert-butylphosphine (0.45 mmol) was added, the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 8.7G of product G2 in 76% yield; MS:763[ M ] + ]。
EXAMPLE 2 Synthesis of Compound G7
Compounds Z3 (8.37 g,15 mmol) and Z5 (3.68 g,15 mmol) were dissolved in anhydrous toluene, sodium t-butoxide (1.73 g,18 mmol) and dibenzylideneacetone dipalladium (0.41 g,0.45 mmol) were added, nitrogen was replaced three times, and then tri-t-butylphosphine (0.45 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 7.37G of product G7 in 68% yield; MS:723[ M ] + ]。
EXAMPLE 3 Synthesis of Compound G6
Compounds Z3 (6.7 g,12 mmol) and Z6A (3.73 g,12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.34 g,14 mmol) and dibenzylideneacetone dipalladium (0.33 g,0.36 mmol) were added, nitrogen was replaced three times, and then tri-tert-butylphosphine (0.36 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 5.03G of product G18 in 58% yield; MS:773[ M ] + ]。
EXAMPLE 4 Synthesis of Compound G23
Z7 (5.32 g,20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 12.5 mL) was slowly added. After about 0.5 hours, a solution of Z1 (6.88 g,20 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 6.99g of Z8 in total, and the yield was 68%.
Compounds Z8 (6.17 g,12 mmol) and Z9 (3.3 g,12 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.34 g,14 mmol) and dibenzylideneacetone dipalladium (0.33 g,0.36 mmol) were added, nitrogen was replaced three times, and then tri-tert-butylphosphine (0.36 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 6.78G of product G23 in 75% yield; MS:753[ M ] + ]。
EXAMPLE 5 Synthesis of Compound G41
P-dibromobenzene (9.36 g,40 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 12.5 mL) was slowly added. After about 0.5 hours, a solution of phenanthrenone (4.16 g,20 mmoL) in anhydrous tetrahydrofuran was added dropwise to the reaction flask, the reaction was continued at this temperature for half an hour, and then the reaction was allowed to warm to room temperature and continued for 8 hours. Water was added, the mixture was separated, extracted and concentrated by a silica gel column to give 6.45g of Z10 in 62% yield.
Z10 (6.24 g,12 mmol) was placed in trifluoromethanesulfonic acid, stirred at room temperature for 1 hour, neutralized by adding aqueous sodium bicarbonate solution, extracted with dichloromethane, and concentrated through a silica gel column to give a total of 5.18g of Z10 in 86% yield.
Z12 (2.32 g,10 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 12.5 mL) was slowly added. After about 0.5 hours, a solution of Z11 (5.02 g,10 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 4.59g of Z13 in a yield of 72%.
Z13 (4.47 g,7 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 4.3 mL) was slowly added, the reaction was continued at this temperature for half an hour, then warmed to room temperature and continued for 8h. Water was added thereto, the mixture was separated, extracted and concentrated by a silica gel column to obtain 3.53g of Z13A in 90% yield.
Compound Z13A (3.36 g,6 mmol) and Z4 (1.71 g,6 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.69 g,7.2 mmol) and dibenzylideneacetone dipalladium (0.16 g,0.18 mmol) were added, nitrogen was replaced three times, and then tri-tert-butylphosphine (0.18 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 3.9G of product G41 in 85% yield; MS:765[ M ] + ]。
EXAMPLE 6 Synthesis of Compound G58
Z14 (7.9 g,25 mmol), 1-naphthalene boric acid (4.3 g,25 mmol), potassium carbonate (10.35 g,75 mmol) and tetrakis (triphenylphosphine) palladium (0.87 g,0.75 mmol) were weighed into a 250mL two-necked flask, a mixed solvent of toluene and methanol was added, nitrogen was introduced three times, and the temperature was raised to 90℃and stirred overnight. After the reaction solution is cooled to room temperature, water is added, ethyl acetate is used for extraction, sodium sulfate is used for drying, the organic solvent is removed through reduced pressure distillation, and the target product Z15 is obtained through silica gel sample mixing column chromatography separation, wherein the yield is 62 percent.
Z15 (4.74 g,15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 9.4 mL) was slowly added. After about 0.5 hours, a solution of Z1 (5.16 g,15 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 5.92g of Z16 in a yield of 70%.
Compound Z16 (5.64 g,10 mmol) and Z17 (2.19 g,10 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.15 g,12 mmol) and dibenzylideneacetone dipalladium (0.27 g,0.3 mmol) were added, nitrogen was replaced three times, and then tri-tert-butylphosphine (0.3 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 4.56G of product G58 in 61% yield; MS:747[ M ] + ]。
EXAMPLE 7 Synthesis of Compound G73
Z14 (7.9 g,25 mmol), 2-naphthalene boric acid (4.3 g,25 mmol), potassium carbonate (10.35 g,75 mmol) and tetrakis (triphenylphosphine) palladium (0.87 g,0.75 mmol) were weighed into a 250mL two-necked flask, a mixed solvent of toluene and methanol was added, nitrogen was introduced three times, and the temperature was raised to 90℃and stirred overnight. After the reaction solution is cooled to room temperature, water is added, ethyl acetate is used for extraction, sodium sulfate is used for drying, the organic solvent is removed through reduced pressure distillation, and the target product Z19 is obtained through silica gel sample mixing column chromatography separation, wherein the total yield is 4.11g, and the yield is 52%.
Z19 (3.79 g,12 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 7.5 mL) was slowly added. After about 0.5 hours, a solution of Z1 (4.13 g,12 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 3g of Z20 in 43% yield.
Compounds Z20 (2.61 g,4.5 mmol) and Z6 (1.1 g,4.5 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.52 g,5.4 mmol) and dibenzylideneacetone dipalladium (0.13 g,0.14 mmol) were added, nitrogen was replaced three times, and after addition of tri-tert-butylphosphine (0.14 mmol), the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, and the heat source was removed. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 2.36G of product G73, yield 68%; MS:773[ M ] + ]。
EXAMPLE 8 Synthesis of Compound G107
Dibenzothiophene boric acid (5.7 g,25 mmol), Z14 (7.9 g,25 mmol), potassium carbonate (10.35 g,75 mmol) and tetrakis (triphenylphosphine) palladium (0.87 g,0.75 mmol) were weighed into a 250mL two-necked flask, a mixed solvent of toluene and methanol was added, nitrogen was purged three times, and the temperature was raised to 90℃and stirred overnight. After the reaction solution is cooled to room temperature, water is added, ethyl acetate is used for extraction, sodium sulfate is used for drying, the organic solvent is removed through reduced pressure distillation, and the target product Z21 is obtained through silica gel sample mixing column chromatography separation, wherein the yield is 68 percent.
Z21 (5.58 g,15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 9.4 mL) was slowly added. After about 0.5 hours, a solution of Z1 (5.16 g,15 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 6.6g of Z22 in 71% yield.
Compound Z22 (6.2 g,10 mmol) and diphenylamine (1.86 g,11 mmol) were dissolved in anhydrous toluene Sodium tert-butoxide (1.15 g,12 mmol) and dibenzylideneacetone dipalladium (0.27 g,0.3 mmol) were added thereto, nitrogen was replaced three times, and then tri-tert-butylphosphine (0.45 mmol) was added thereto, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 6.4G of product G107 in 85% yield; MS:753[ M ] + ]。
EXAMPLE 9 Synthesis of Compound G155
Z22 (10.5 g,30 mmol), o-bromophenylboric acid (6 g,30 mmol), potassium carbonate (12.42 g,90 mmol) and tetrakis (triphenylphosphine) palladium (1.04 g,0.9 mmol) were weighed into a 250mL two-necked flask, a mixed solvent of toluene and methanol was added, nitrogen was introduced three times, and the temperature was raised to 90℃and stirred overnight. After the reaction solution is cooled to room temperature, water is added, ethyl acetate is used for extraction, sodium sulfate is used for drying, the organic solvent is removed through reduced pressure distillation, and the target product Z23 is obtained through silica gel sample mixing column chromatography separation, wherein the total yield is 5.77g, and the yield is 54%.
Z23 (5.34 g,15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 9.4 mL) was slowly added. After about 0.5 hours, a solution of Z1 (5.16 g,15 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 7.16g of Z25 in 79% yield.
Compound Z25 (6.04 g,10 mmol) and diphenylamine (1.86 g,11 mmol) were dissolved in anhydrous toluene, sodium t-butoxide (1.15 g,12 mmol) and dibenzylideneacetone dipalladium (0.37 g,0.3 mmol) were added, nitrogen was replaced three times, and then tri-t-butylphosphine (0.3 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system cooled, deionized water was added to separate the organic layer, and ethyl acetate was usedExtracting for three times, concentrating under reduced pressure, and passing through a silica gel column to obtain 5.6G of a product G155 with the yield of 76%; MS:737[ M ] + ]。
EXAMPLE 10 Synthesis of Compound G166
Z26 (6.52 g,20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 12.5 mL) was slowly added. After about 0.5 hours, a solution of Z1 (6.88 g,20 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain a total of 7.92g of Z27 in 69% yield.
Compound Z27 (6.89 g,12 mmol) and Z4 (3.42 g,12 mmol) were dissolved in anhydrous toluene, sodium t-butoxide (1.34 g,14 mmol) and dibenzylideneacetone dipalladium (0.33 g,0.36 mmol) were added, nitrogen was replaced three times, and then tri-t-butylphosphine (0.36 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 6.54G of product G166 in 70% yield; MS:779[ M ] + ]。
EXAMPLE 11 Synthesis of Compound G174
Parobromotoluene (5.95 g,35 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 21.8 mL) was slowly added. After about 0.5 hours, a solution of phenanthrenone (3.54 g,17 mmoL) in anhydrous tetrahydrofuran was added dropwise to the reaction flask, the reaction was continued at this temperature for half an hour, and then the reaction was allowed to warm to room temperature and continued for 8 hours. Water was added, the mixture was separated, extracted and concentrated on a silica gel column to give a total of 5.2g of Z28 in 78% yield.
Z28 (4.7 g,12 mmol) was placed in trifluoromethanesulfonic acid, stirred at room temperature for 1 hour, neutralized by adding aqueous sodium bicarbonate solution, extracted with dichloromethane, and concentrated through a silica gel column to give 3.28g total of Z29 in 73% yield.
Z2 (2.48 g,8 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 12.5 mL) was slowly added. After about 0.5 hours, a solution of Z29 (3 g,8 mmoL) in anhydrous tetrahydrofuran was added dropwise to the flask, the reaction was continued at this temperature for half an hour, and then it was warmed to room temperature and continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 3.06g of Z30 in a yield of 65%.
Compounds Z30 (2.94 g,5 mmol) and Z31 (1.38 g,5 mmol) were dissolved in anhydrous toluene, sodium t-butoxide (0.57 g,6 mmol) and dibenzylideneacetone dipalladium (0.14 g,0.15 mmol) were added, nitrogen was replaced three times, and then tri-t-butylphosphine (0.15 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 3.17G of product G174 in 81% yield; MS:783[ M ] + ]。
EXAMPLE 12 Synthesis of Compound G196
Z2 (6.2 g,20 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to-78℃and butyllithium (1.6M, 12.5 mL) was slowly added. After about 0.5 hours, this reaction solution was added to an anhydrous tetrahydrofuran solution of phenanthrenone (4.16 g,20 mmoL), the reaction was continued at this temperature for half an hour, and then, it was warmed to room temperature, and the reaction was continued for 8 hours. The solvent was removed under reduced pressure, hydrochloric acid and acetic acid were added, and the mixture was refluxed for about 2 hours. Cooled to room temperature, deionized water was added, and extraction was performed with ethyl acetate. After concentration, the mixture was separated by a silica gel column, and the solvent was removed to obtain 5.4g of Z32 in a yield of 64%.
The above procedure was repeated to give a total of 4g of Z33 in 52% yield.
Compound Z33 (3.8 g,6 mmol) and diphenylamine (2.37 g,14 mmol) were dissolved in anhydrous toluene, sodium t-butoxide (1.73 g,18 mmol) and dibenzylideneacetone dipalladium (0.27 g,0.3 mmol) were added, nitrogen was replaced three times, and then tri-t-butylphosphine (0.3 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 3.47G of product G196 in 71% yield; MS:814[ M ] + ]。
EXAMPLE 13 Synthesis of Compound G206
Z8 (7.71 g,15 mmol), anthranilic acid ester (3.3 g,15 mmol), potassium carbonate (6.21 g,45 mmol) and tetrakis (triphenylphosphine) palladium (0.52 g,0.45 mmol) were weighed into a 250mL two-necked flask, a mixed solvent of toluene and methanol was added, nitrogen was purged three times, and the temperature was raised to 90℃and stirred overnight. After the reaction solution is cooled to room temperature, water is added, ethyl acetate is used for extraction, sodium sulfate is used for drying, the organic solvent is removed through reduced pressure distillation, and the target product Z34 is obtained through silica gel sample mixing column chromatography separation, wherein the total yield is 5.91g, and the yield is 69%.
Compound Z34 (5.71 g,10 mmol) and bromobenzene (3.43 g,22 mmol) were dissolved in anhydrous toluene, sodium t-butoxide (2.11 g,22 mmol) and dibenzylideneacetone dipalladium (0.46 g,0.5 mmol) were added, nitrogen was replaced three times, and then tri-t-butylphosphine (0.5 mmol) was added, and the temperature was gradually raised to 80℃and the reaction was stirred for 12 hours, followed by removal of the heat source. After the system was cooled, deionized water was added, the organic layer was separated, extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to give 4.41G of product G206 in 61% yield; MS:723[ M ] + ]。
Preparation and characterization of OLED devices
The following describes in detail the preparation process of the OLED device by using the specific embodiment, and the OLED device has the following structure: ITO/HIL (5 nm)/H1 (80 nm)/G2 (20 nm)/GD 1: GH1 (30 nm)/ET 1: liQ (30 nm)/LiQ (2 nm)/Al (80 nm), the preparation steps are as follows:
a. and cleaning the conductive glass substrate, namely ultrasonically cleaning the conductive glass substrate for 15 minutes by using deionized water, acetone and isopropanol, and then performing ultraviolet ozone plasma treatment.
b. Functional layer preparation: the ITO substrate was transferred into a vacuum vapor deposition apparatus under high vacuum (1X 10 -6 Mbar) by resistive heating evaporation, HATCN evaporation to form a 5nm Hole Injection Layer (HIL), evaporation rateThen, a hole transport layer (H1) of 80nm was obtained by vapor deposition on the hole injection layer. An electron blocking layer (G2) of 20nm was vapor deposited on the hole transport layer. And (3) evaporating a light-emitting layer on the electron blocking layer, wherein GH1 is used as a main material, GD1 is used as a doping material, the mass ratio of GD1 to GH1 is 1:9, and the thickness is 30nm. On the light-emitting layer, electron transport materials ET1 and LiQ were vapor-deposited by vacuum vapor deposition in a ratio of 5:5, thickness is 30nm. Finally, a cathode Al layer is evaporated on the electron transport layer in a vacuum way, and the thickness is 80nm.
c. Encapsulation the device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.
Device example 2: the electron blocking layer of the organic electroluminescent device becomes G7.
Device example 3: the electron blocking layer of the organic electroluminescent device becomes G6.
Device example 4: the electron blocking layer of the organic electroluminescent device becomes G23.
Device example 5: the electron blocking layer of the organic electroluminescent device becomes G41.
Device example 6: the electron blocking layer of the organic electroluminescent device becomes G58.
Device example 7: the electron blocking layer of the organic electroluminescent device becomes G73.
Device example 8: the electron blocking layer of the organic electroluminescent device becomes G107.
Device example 9: the electron blocking layer of the organic electroluminescent device becomes G155.
Device example 10: the electron blocking layer of the organic electroluminescent device becomes G166.
Device example 11: the electron blocking layer of the organic electroluminescent device becomes G174.
Device example 12: the electron blocking layer of the organic electroluminescent device becomes G196.
Device example 13: the electron blocking layer of the organic electroluminescent device becomes G206.
Device comparative example 1: the electron blocking layer of the organic electroluminescent device becomes C1.
The structure of the compound involved in the device is as follows:
TABLE 1
The characteristics of each OLED device are characterized by a characterization device while recording important parameters such as lifetime and luminous efficiency. Table 1 shows a comparison of OLED device lifetime and luminous efficiency, wherein lifetime LT95 is measured at a constant current (current density of 10mA/cm 2 ) The time when the luminance falls to 95% of the initial luminance @1000 nits. Here, LT95 and luminous efficiency are both at a current density of 10mA/cm 2 The relative value calculated for comparative example 1 with respect to the device, i.e., the lifetime of comparative device example 1 was 1 and the luminous efficiency was 1.
The devices of device examples 1-13 have significantly higher luminous efficiencies and lifetimes than comparative device example 1. Therefore, the arylamine compound can be used as an electron blocking material to effectively improve the luminous efficiency and prolong the service life of the organic electroluminescent device.
The technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples illustrate only a few embodiments of the invention, which are described in detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.

Claims (10)

1. A polycyclic aromatic amine organic compound is shown in a general formula (1):
wherein Z is selected from single bond or O;
m is selected from 0 or 1, n is selected from 0 or 1, and m+n is more than or equal to 1;
Ar 1 ～Ar 8 each occurrence is independently selected from any one of the following groups:
x is selected from CR 1 ，R 1 Selected from H, a linear alkyl group having 1 carbon atom or an aryl group having 6 to 14 ring atoms;
y is selected from O, S or CR 2 R 3 ，R 2 、R 3 Each occurrence is independently selected from the group consisting of straight chain alkyl groups having 1C atom;
L 1 、L 2 each occurrence is independently selected from a single bond or phenyl.
2. The organic compound according to claim 1, wherein formula (1) is selected from structures represented by formula (2):
3. the organic compound according to claim 2, wherein formula (1) is selected from structures represented by any one of formulas (3-1) to (3-8):
4. an organic compound according to claim 3, wherein Z is selected from single bonds.
5. An organic compound according to any one of claims 1 to 4, wherein Ar 1 ～Ar 4 Each occurrence is independently selected from any one of the following groups:
6. the organic compound according to any one of claims 1 to 4, wherein formula (1) is selected from structures represented by formula (4-1):
7. a mixture comprising at least one organic compound according to any one of claims 1 to 6, and at least one organic functional material selected from the group consisting of a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, an organic light emitting guest material, a host material, and inorganic quantum dots.
8. A composition comprising at least one organic compound according to any one of claims 1 to 6 or a mixture according to claim 7, and at least one organic solvent.
9. An organic electronic device comprising at least one organic compound according to any one of claims 1 to 6 or a mixture according to claim 7 or prepared from a composition according to claim 8.
10. The organic electronic device according to claim 9, comprising a light-emitting layer, a hole-transporting layer and an electron-blocking layer comprising a compound according to any one of claims 1 to 6 or a mixture according to claim 7 or prepared from a composition according to claim 8.
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