CN108658941A - Contain unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and display device - Google Patents
Contain unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and display device Download PDFInfo
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- 0 Cc(cccc1-c(cc2)cc(nc3-c(cc4)ccc4N(c4c5cccc4)c4ccccc4C5(c(cc4)ccc4-c4c(CCC=C5)c5c(-c5ccccc5)c5c4cccc5)[n]4c5ccccc5c5c4cccc5)c2[n]3-c2ccccc2)c1-c(cccc1)*1Nc(cc1)cc(C(C2C=C3)C=C3[n]3c4ccccc4c4c3cccc4)c1N2C1(c(cc2)ccc2-c2ccccc2)c2ccccc2N(C(C=C2)=CCC2c2nc(cccc3)c3[n]2-c2ccccc2)c2ccccc12 Chemical compound Cc(cccc1-c(cc2)cc(nc3-c(cc4)ccc4N(c4c5cccc4)c4ccccc4C5(c(cc4)ccc4-c4c(CCC=C5)c5c(-c5ccccc5)c5c4cccc5)[n]4c5ccccc5c5c4cccc5)c2[n]3-c2ccccc2)c1-c(cccc1)*1Nc(cc1)cc(C(C2C=C3)C=C3[n]3c4ccccc4c4c3cccc4)c1N2C1(c(cc2)ccc2-c2ccccc2)c2ccccc2N(C(C=C2)=CCC2c2nc(cccc3)c3[n]2-c2ccccc2)c2ccccc12 0.000 description 3
- LODQPJWSIVYROX-UHFFFAOYSA-N C(C1)C=CC=C1c1ccc(C2(c3ccccc3N(c(cc3)ccc3-c3nc4ccccc4[n]3-c3ccccc3)c3c2cccc3)[n]2c3cc(-c4ccccc4C4(c5ccccc5)c5ccccc5)c4cc3c3c2cccc3)cc1 Chemical compound C(C1)C=CC=C1c1ccc(C2(c3ccccc3N(c(cc3)ccc3-c3nc4ccccc4[n]3-c3ccccc3)c3c2cccc3)[n]2c3cc(-c4ccccc4C4(c5ccccc5)c5ccccc5)c4cc3c3c2cccc3)cc1 LODQPJWSIVYROX-UHFFFAOYSA-N 0.000 description 1
- MWJZZBMWNVYLJT-UHFFFAOYSA-N C(C1c2c3)=CC=CC1N(C1(c(cc4)ccc4-c4ccccc4)c4ccccc4N(c(cc4)ccc4-c4nc5ccccc5[n]4-c4ccccc4)c4c1cccc4)c2cc(c1ccccc11)c3[n]1-c1ccccc1 Chemical compound C(C1c2c3)=CC=CC1N(C1(c(cc4)ccc4-c4ccccc4)c4ccccc4N(c(cc4)ccc4-c4nc5ccccc5[n]4-c4ccccc4)c4c1cccc4)c2cc(c1ccccc11)c3[n]1-c1ccccc1 MWJZZBMWNVYLJT-UHFFFAOYSA-N 0.000 description 1
- RJWYZGYGLBNDGS-UHFFFAOYSA-N C(CC1)CCC1c1ccc(C2(c3ccccc3N(c(cc3)ccc3-c3nc4ccccc4[n]3-c3ccccc3)c3c2cccc3)[n]2c3ccccc3c3c2cccc3)cc1 Chemical compound C(CC1)CCC1c1ccc(C2(c3ccccc3N(c(cc3)ccc3-c3nc4ccccc4[n]3-c3ccccc3)c3c2cccc3)[n]2c3ccccc3c3c2cccc3)cc1 RJWYZGYGLBNDGS-UHFFFAOYSA-N 0.000 description 1
- KFHLKTZPRXJCTL-UHFFFAOYSA-N C1C=CC=CC1[n]1c(C(C=C2)=CCC2N(c2c3cccc2)c2ccccc2C3(c(cc2)ccc2-c2ccccc2)[n](c(ccc(-c2ccccc2)c2)c2c2c3)c2ccc3-c2ccccc2)nc2c1cccc2 Chemical compound C1C=CC=CC1[n]1c(C(C=C2)=CCC2N(c2c3cccc2)c2ccccc2C3(c(cc2)ccc2-c2ccccc2)[n](c(ccc(-c2ccccc2)c2)c2c2c3)c2ccc3-c2ccccc2)nc2c1cccc2 KFHLKTZPRXJCTL-UHFFFAOYSA-N 0.000 description 1
- LUBCGPOLBGIPNF-UHFFFAOYSA-N CCN(c1ccccc1C1=CC23)C1=CC2c(cccc1)c1N3C1(c(cc2)ccc2-c2ccccc2)C(C=CCC2)=C2N(c(cc2)ccc2-c2nc3ccccc3[n]2-c2ccccc2)c2ccccc12 Chemical compound CCN(c1ccccc1C1=CC23)C1=CC2c(cccc1)c1N3C1(c(cc2)ccc2-c2ccccc2)C(C=CCC2)=C2N(c(cc2)ccc2-c2nc3ccccc3[n]2-c2ccccc2)c2ccccc12 LUBCGPOLBGIPNF-UHFFFAOYSA-N 0.000 description 1
- LKGYYXNPFJRTRX-UHFFFAOYSA-N Cc1cccc(C2(c3ccccc3)C(C=CCC3)=C3N(C3(c(cc4)ccc4C4=CCCC=C4)c(cccc4)c4N(C4C=CC(c5nc(cccc6)c6[n]5C5=CCCC=C5)=CC4)c4c3cccc4)c3c2cccc3)c1 Chemical compound Cc1cccc(C2(c3ccccc3)C(C=CCC3)=C3N(C3(c(cc4)ccc4C4=CCCC=C4)c(cccc4)c4N(C4C=CC(c5nc(cccc6)c6[n]5C5=CCCC=C5)=CC4)c4c3cccc4)c3c2cccc3)c1 LKGYYXNPFJRTRX-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Abstract
The present invention relates to display technology fields, containing unsaturated nitrogenous heterocyclic acridine compound, organic electroluminescence device and display device more particularly to one kind.Shown in compound according to the present invention such as formula (I):
Description
Technical field
The present invention relates to display technology fields, containing unsaturated nitrogenous heterocyclic acridine chemical combination more particularly to one kind
Object, organic electroluminescence device and display device.
Background technology
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as novel
Plate display is compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), has thin, light, wide viewing angle, master
It is dynamic shine, luminescent color is continuously adjustable, at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, gives birth to
Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair
Luminescent material, electroluminescent organic material have the following advantages:Organic material processing performance is good, can pass through vapor deposition or the side of spin coating
Method forms a film on any substrate;The diversity of organic molecular structure allow to by Molecular Design and the method for modification come
It adjusts the thermal stability of organic material, mechanical performance, shine and electric conductivity so that material is significantly improved space.
What the generation of organic electroluminescent was leaned on is the carrier (electrons and holes) transmitted in organic semiconducting materials
Recombination.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued, the transmission of carrier normal in organic semiconductor
It is described with jump theory.In order to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material
Charge injects and the difficulty of transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer
Number, and different organic layers is made to play the part of different functional layers, such as the functional material having can promote electronics from cathode
Injection, some functional materials can promote hole to be injected from anode, and some materials can promote the transmission of charge, and some materials are then
It can play the role of stopping electronics or hole transport, the hair of most important a variety of colors certainly in organic electroluminescence device
Luminescent material will also achieve the purpose that match with adjacent functional material, therefore, the organic electroluminescence device of excellent in efficiency long lifespan
Typically device architecture and various organic materials optimize arranging in pairs or groups as a result, this, which is just chemists, designs and develops various structures
Functionalization material provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode, electron injecting layer, electronics being arranged in order from top to bottom
Transport layer (Electron transport Layer, abbreviation ETL), organic luminous layer (Emitting Layer, abbreviation EML),
Hole transmission layer, hole injection layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly in organic light emission
The formation probability of exciton is improved in layer as possible, therefore the organic luminous layer of organic electroluminescence device and hole adjacent thereto pass
The material of defeated layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And it is in the prior art
Hole transmission layer or organic luminous layer make organic electroluminescence device have higher driving voltage and lower luminous efficiency.
Invention content
The present invention provides a kind of containing unsaturated nitrogenous heterocyclic acridine compound, includes the Organic Electricity of the compound
Electroluminescence device and display device with the organic electroluminescence device, to solve organic electroluminescence in the prior art
The problem of high driving voltage of part and low luminous efficiency.
According to an aspect of the present invention, it provides a kind of containing unsaturated nitrogenous heterocyclic acridine compound, the chemical combination
Shown in object such as formula (I):
Wherein Ar1Selected from carbon atoms 6~60, the aromatic radical being made of carbon and hydrogen, Ar2Selected from carbon atoms 3~60
The undersaturated oxygen heterocycle of undersaturated nitrogen heterocyclic ring, carbon atom 12~40, Ar1, Ar2It can be by the fat of carbon atoms 1-30
Fat race alkyl, the aliphatic alkoxy of carbon atoms 1-30, carbon atom 6-20 the aromatic radical being made of carbon and hydrogen replaced, and
And Ar2It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen2N atoms directly and on acridine ring connect
It connects, can also be Ar2It is connected, is illustrated with the N atoms on acridine ring with the aromatic radical that hydrogen forms by carbon by carbon atom 6-20
It is described as follows:
Work as Ar2Selected from pyridyl group, when the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from phenyl, Ar2Direct and a word used for translation
When N atoms in phenazine ring connect, shown in obtained compound such as formula (II):
Work as Ar2Selected from pyridyl group, when the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from phenyl, Ar2Pass through carbon original
Sub- 6-20's is connected with the aromatic radical that hydrogen forms with the N atoms on acridine ring by carbon, obtained compound such as formula (III) institute
Show:
A is selected from:
Wherein X, Y, Z, Ar independent aliphatic alkyl, Ar1, carbazyl selected from carbon atoms 1-30;Wherein * indicates A-
The position that structure shown in 1~A-11 is connected with acridine female ring.
Further, Ar1It is selected from:Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene
Base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl;
The aliphatic alkyl of carbon atom 1-30 is selected from:Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl,
Cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl;The aliphatic alkoxy of carbon atoms 1-30 is selected from:Methoxyl group, second
Oxygroup, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, ring fourth oxygen
Base, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies;The aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from:Phenyl, connection
Phenyl, naphthalene, anthryl, phenanthryl, triphenylene.
Ar2It is selected from:Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, dibenzofuran group,
Benzo benzo furyl, dinaphtho furyl;And Ar2Can by methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl,
Octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, propoxyl group, fourth oxygen
Base, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, hexamethylene
Oxygroup, two cyclohexyloxies, phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene substitution.
In addition, the present invention's contains unsaturated nitrogenous heterocyclic acridine compound, Ar1, Ar2It can be by carbon atoms 1-
30 aliphatic alkyl, the aliphatic alkoxy of carbon atoms 1-30 are replaced, wherein the substitution, can be monosubstituted, double
Replace or polysubstituted.
Optionally, according to the present invention to be selected from containing unsaturated nitrogenous heterocyclic acridine compound:
It should be noted that in concrete structure listed above, the connection type of adjacent group is unique, such as in P-
In 21, the phenyl ring contraposition connected on 9 carbon atoms of acridine ring is replaced by another phenyl ring, in fact, 9 carbon atoms of acridine ring
The meta position of the phenyl ring of upper connection by another phenyl ring replace and 9 carbon atoms of acridine ring on the ortho position of phenyl ring that connects it is another
Outer phenyl ring substitution is formed by compound, shown in following (a), (b):
It can achieve the effect that the present invention, belong to the content of the invention to be disclosed and be protected.Such the position of substitution
Change, there is no the agent structures for changing the compounds of this invention, without influence on the application technology effect of the compounds of this invention.
Therefore, in the logical formula (I) of the present invention
In, A, Ar1, Ar2The change of connection type, belongs between representative inside configuration difference or identical group
Within the scope of disclosure of the invention and protection.
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided
Including according to the present invention contain unsaturated nitrogenous heterocyclic acridine compound.
Optionally, the material of main part of the organic luminous layer of the organic electroluminescence device, the material of hole transmission layer, electricity
The material of sub- transport layer is according to the present invention containing unsaturated nitrogenous heterocyclic acridine compound.
Optionally, organic electroluminescence device according to the present invention, the organic luminous layer are blue light-emitting layer, green hair
Photosphere, Yellow luminous layer or red light emitting layer.
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having
Organic electroluminescence devices.
Beneficial effects of the present invention are as follows:
By compound provided by the invention for the hole transmission layer of organic electroluminescence device or the master of organic luminous layer
Body material improves the luminous efficiency of organic electroluminescence device, reduces the driving voltage of organic electroluminescence device.
Specific implementation mode
Specific implementation mode is only the description of the invention, without constituting the limitation to the content of present invention, below in conjunction with
Invention is further explained and description for specific embodiment.
In order to which the compound of the present invention is explained in more detail, the synthetic method pair of above-mentioned particular compound will be enumerated below
The present invention is further described.
The synthesis of compound P-1
(1) synthesis of intermediate M-1:
In 1000 milliliters of there-necked flasks, under nitrogen protection, 500 milliliters of toluene, 19.5 grams of (0.1mol) acridines -9 are added
(10H) -one, 15.8 grams of (0.1mol) 2- bromopyridines, 11.52 grams of (0.12mol) sodium tert-butoxides, 0.575 gram of (0.001mol) Pd
(dba)2(bis- (dibenzalacetone) palladiums), 10% toluene solution of 2.02 grams of (0.001mol) tri-tert-butylphosphines is heated to
Back flow reaction 4 hours, cooling add moisture liquid, organic layer washing, anhydrous magnesium sulfate drying, silica gel column chromatography separation, petroleum ether:
Ethyl acetate=1:2 (volume ratios) elution separation, obtains 22.3 grams of compound shown in formula M-1, yield 81.98%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-1, has obtained the m/e of product:272.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-1, obtained nuclear-magnetism parsing data are as follows:
1HNMR (500MHz, CDCl3):δ 8.05 (m, 1H), δ 7.65 (m, 2H), δ 7.55 (m, 1H), δ 7.48 (m, 2H), δ
7.26 (m, 2H), δ 7.21 (m, 1H), δ 7.08 (m, 2H), δ 6.70 (m, 1H).
(2) synthesis of intermediate M-2:
In 1000 milliliters of there-necked flasks, 400 milliliters of tetrahydrofurans, 15.7 grams of (0.1mol) bromobenzenes, drop is added in nitrogen protection
The hexane solution of the butyl lithium of 59.4 milliliters of (0.095mol) 1.6M is slowly added dropwise to -78 DEG C in temperature, finishes in -78 DEG C of heat preservations
30 minutes, -78 to -70 DEG C are controlled, 200 milliliters of tetrahydrochysene furans of compound shown in 21.76 grams of (0.08mol) formula M-1 are slowly added to
It mutters solution, finishes, be slowly increased to room temperature, 100 milliliter 36% of hydrochloric acid is then added, 5 milliliter 95% of sulfuric acid is stirred at room temperature 8
Hour, it is adjusted to neutrality with sodium hydroxide solution, adds water and dichloromethane liquid separation, organic layer washing, anhydrous magnesium sulfate is dried, dense
Be reduced to it is solvent-free after, silica gel column chromatography separation, petroleum ether:Ethyl acetate=5:2 (volume ratios) elution separation, obtains formula M-2 institutes
Show 11.2 grams of compound, yield 30.35%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-2, has obtained the m/e of product:368.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-2, obtained nuclear-magnetism parsing data are as follows:
1HNMR (500MHz, CDCl3):δ 8.04 (m, 1H), δ 7.55 (m, 1H), δ 7.37~7.18 (m, 12H), δ 7.00
(m, 2H), δ 7.71 (m, 1H).
(3) synthesis of compound P-1
In 250 milliliters of there-necked flask, under nitrogen protection, be added 100 milliliters of dry toluene, 3.69 grams
Compound shown in (0.01mol) formula M-2,2 grams of (0.012mol) carbazoles, 1.25 grams of (0.013mol) sodium tert-butoxides, 0.11 gram
(0.0002mol) bis- (dibenzalacetone) palladiums, 0.39 gram of (0.0002mol) 10% tri-tert-butylphosphine toluene solution, add
Heat is down to room temperature after 12 hours to back flow reaction, and dilute hydrochloric acid, liquid separation is added, and organic layer is washed with water neutrality, uses anhydrous slufuric acid
After magnesium drying, with silica gel post separation, petroleum ether is used:Ethyl acetate (volume ratio 5:1) it is eluted as eluant, eluent, obtains formula
3.18 grams of product shown in P-1, yield 63.65%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out:499.
Nuclear-magnetism detection is carried out to obtained compound P-1, the parsing data of obtained nuclear magnetic spectrogram are as follows:
1HNMR (500MHz, CDCl3):δ 8.55 (m, 1H), δ 8.34 (m, 1H), δ 8.04 (m, 1H), δ 7.78 (m, 1H), δ
7.60~7.50 (m, 2H), δ 7.41 (m, 1H), δ 7.35~7.08 (m, 15H), δ 6.95 (m, 2H), δ 6.77 (m, 1H).
The synthesis of other parts compound of the present invention
The synthetic method of synthetic method reference P-1, only as needed in the synthesis of M-1, by 2- bromopyridines therein
It changes corresponding bromo-derivative 1 into, in the synthesis of M-2, changes bromobenzene therein into bromo-derivative 2, in the synthesis of compound P-1,
It changes carbazole therein into corresponding nitrogen-containing hetero cyclics, Mass Spectrometer Method has been carried out to obtained compound, had been synthesized
The raw material and product Mass Spectrometer Method result of Cheng Suoyong see the table below:
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device
The material of main part of organic luminous layer, the material of hole transmission layer or electron transport layer materials are according to the compound of the present invention.
Organic electroluminescence device according to the present invention, the organic luminous layer are blue light-emitting layer, green light emitting layer, Huang
Color luminescent layer or red light emitting layer.
The typical structure of organic electroluminescence device is:Substrate/anode/hole injection layer/hole transmission layer (HTL)/has
Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light
Layer can also be multi-luminescent layer.
Wherein, substrate can use the substrate in conventional organic electroluminescence device, such as:Glass or plastics.Anode can be with
Using transparent high conductivity material, such as:Indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO).
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable that there is height
Thermal stability (high Tg), have a smaller potential barrier with anode, can vacuum evaporation form pin-hole free films.Commonly HIM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
The hole mobile material (Hole Transport Material, abbreviation HTM) of hole transmission layer, it is desirable that there is height
Thermal stability (high Tg), higher cavity transmission ability, can vacuum evaporation formed pin-hole free films.Commonly HTM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, such as is contaminated
Material, material of main part need to have following characteristics:Reversible electrochemical redox current potential, with adjacent hole transmission layer and electronics
The HOMO energy levels and lumo energy that transport layer matches, the good and hole to match and electron transport ability are good high
Thermal stability and film forming, and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer, also with phase
Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer is needed by taking dyestuff as an example
Have following characteristics:With high fluorescence or phosphorescence quantum efficiency;The absorption spectrum of dyestuff and the emission spectrum of main body have
Overlapping, i.e. main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff;The emission peak of red, green, blue to the greatest extent may be used
Can be narrow, with the excitation purity obtained;Stability is good, can be deposited etc..
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM
There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy levels and LUMO (Lowest Unoccupied
Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with
Hole blocking ability;Higher electron transport ability, the film forming and thermal stability having had.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.Electron transfer layer uses Alq3 (8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4-
(1 '-naphthalene) -5- benzene -1,2,4- triazoles) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazoles) benzene) or be derived from this three
Arbitrary two kinds of the collocation of kind material.
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having
Organic electroluminescence devices
It can be seen that the optional factor of compound according to the present invention, organic electroluminescence device and display device is more,
Claim according to the present invention can be combined into different embodiments.The embodiment of the present invention is only as to the specific of the present invention
Description, is not intended as limitation of the present invention.Make below in conjunction with the organic electroluminescence device containing the compound of the present invention
For embodiment, the present invention is described further.
The different materials concrete structure used in the present invention is seen below:
Embodiment 1
Material of main part in using the compound of the present invention as red phosphorescent OLED organic electroluminescence devices, as a comparison
Organic electroluminescence device, feux rouges material of main part select CBP.
Organic electroluminescence device structure is:ITO/NPB (20nm)/feux rouges material of main part (30nm):Ir(piq)3
[5%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows:The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone:Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm;
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm;Wherein " Ir (piq) 3 [5%] " refers to the doping ratio of red dye
The weight part ratio of example, i.e. feux rouges material of main part and Ir (piq) 3 are 100:5;
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate film thickness;
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 1:
Table 1
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive
Dynamic voltage.
Embodiment 2
Material of main part in using the compound of the present invention as green phosphorescent OLED organic electroluminescence devices, as a comparison
Organic electroluminescence device, green light material of main part selects CBP respectively.
Organic electroluminescence device structure is:ITO/NPB (20nm)/green light material of main part (30nm):Ir(ppy)3
[7%]/TPBI (10nm)/Alq3 (15nm)/LiF (0.5nm)/Al (150nm).
Organic electroluminescence device preparation process is as follows:The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone:Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm;
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm;Wherein " Ir (ppy) 3 [7%] " refers to the doping ratio of green light dyestuff
The weight part ratio of example, i.e. green light material of main part and Ir (ppy) 3 are 100:7;
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate film thickness;
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 2:
Table 2
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and lower drive
Dynamic voltage.
Embodiment 3
Material of main part in using the compound of the present invention as blue phosphorescent OLED organic electroluminescence devices, as a comparison
Organic electroluminescence device, Blue-light emitting host material selects CBP respectively.
Organic electroluminescence device structure is:ITO/NPB (20nm)/Blue-light emitting host material (30nm):FIrpic [4%]/
TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone:Ultrasonic oil removing, is toasted under clean environment in alcohol mixed solvent
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean to the complete moisture content that removes;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer NPB on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm;
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm;Wherein " FIrpic [4%] " refers to the doping ratio of blue light dyestuff
Example, the i.e. weight part ratio of Blue-light emitting host material and FIrpic are 100:4;
Vacuum evaporation electron transfer layer TPBI and Alq3, evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate film thickness;
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Organic electroluminescence device performance is shown in Table 3:
Table 3
By upper table, it can be seen that, chemical combination of the present invention can be as the phosphorescent light body material of blue organic electroluminescent device.
Embodiment 4
Hole transmission layer in using the compound of the present invention as organic electroluminescence device, organic electroluminescence as a comparison
Luminescent device, hole mobile material select NPB respectively.
Organic electroluminescence device structure is:ITO/HIL02(100nm)/HTL(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, HIL02 makees
Hole injection layer, EM1 make the material of main part of organic luminous layer, and LiF/Al makees electron injecting layer/cathode material.
Organic electroluminescence device preparation process in the present embodiment is as follows:
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in water, to improve the property on surface, improves and is passed with hole
The binding ability of defeated layer;
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode
HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness;
The vacuum evaporation hole transmission layer on hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 40nm;
Organic luminous layers of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 30nm;
Electron transfer layers of the vacuum evaporation TAZ as organic electroluminescence device on organic luminous layer;Speed is deposited in it
Rate is 0.1nm/s, and vapor deposition total film thickness is 20nm;
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL);
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 4:
Table 4
Embodiment 5
Electron transfer layer in using the compound of the present invention as organic electroluminescence device, organic electroluminescence as a comparison
Luminescent device, electron transport material select TAZ.
Organic electroluminescence device structure is:ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device in the present embodiment selects glass substrate, ITO to make anode material in making, HIL02 makees
Hole injection layer, NPB make hole transmission layer, and EM1 makees the material of main part of organic luminous layer, and LiF/Al makees electron injecting layer/cathode
Material.
Organic electroluminescence device preparation process in the present embodiment is as follows:
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Low energy cation beam bombarded surface is used in combination with ultraviolet light and ozone clean in water, to improve the property on surface, improves and is passed with hole
The binding ability of defeated layer;
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, the vacuum evaporation on anode
HIL02 is 100nm as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness;
The vacuum evaporation NPB on hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 40nm;
Organic luminous layers of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 30nm;
The vacuum evaporation electron transport material on organic luminous layer, the electron-transport as organic electroluminescence device
Layer;Its evaporation rate is 0.1nm/s, and vapor deposition total film thickness is 20nm;
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL);
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 5:
Table 5
Electron transport material | It is required that brightness cd/m2 | Driving voltage V | Current efficiency cd/A |
TAZ | 1000 | 6.59 | 1.58 |
Compound P-6 | 1000 | 6.41 | 1.67 |
Compound P-11 | 1000 | 5.64 | 1.76 |
Compound P-13 | 1000 | 6.49 | 1.7 |
Compound P-15 | 1000 | 6.61 | 1.76 |
Compound P-21 | 1000 | 6.79 | 1.84 |
Compound P-24 | 1000 | 6.54 | 1.89 |
Compound P-26 | 1000 | 6.68 | 1.6 |
Compound P-30 | 1000 | 6.16 | 1.92 |
Compound P-32 | 1000 | 6.18 | 1.83 |
Compound P-56 | 1000 | 5.87 | 1.89 |
Compound P-57 | 1000 | 5.56 | 1.94 |
Compound P-58 | 1000 | 5.94 | 1.92 |
Compound P-59 | 1000 | 5.77 | 1.82 |
Compound P-60 | 1000 | 5.59 | 1.85 |
Compound P-61 | 1000 | 6.85 | 1.79 |
Compound P-62 | 1000 | 6.03 | 1.85 |
Compound P-63 | 1000 | 6.58 | 1.66 |
Compound P-64 | 1000 | 6.63 | 1.63 |
Compound P-65 | 1000 | 5.9 | 1.66 |
Compound P-66 | 1000 | 6.36 | 1.88 |
Compound P-67 | 1000 | 6.64 | 1.83 |
Compound P-68 | 1000 | 6.05 | 1.72 |
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as electron transfer layer by upper table
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
God and range.In this way, if these modifications and changes of the present invention belongs to the range of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to include these modifications and variations.
Claims (8)
1. one kind is containing unsaturated nitrogenous heterocyclic acridine compound, as shown in formula (I):
Wherein Ar1Selected from carbon atoms 6~60, the aromatic radical being made of carbon and hydrogen;
Ar2The undersaturated oxygen heterocycle of undersaturated nitrogen heterocyclic ring, carbon atom 12~40 selected from carbon atoms 3~60;
The Ar1, Ar2It can be former by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30, carbon
The aromatic radical of sub- 6-20 being made of carbon and hydrogen is replaced;
And Ar2It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen2Directly and the N on acridine ring is former
Son connection, can also be Ar2It is connected with the N atoms on acridine ring with the aromatic radical that hydrogen forms by carbon by carbon atom 6-20;
A is selected from:
Wherein X, Y, Z, Ar independent aliphatic alkyl, Ar1, carbazyl selected from carbon atoms 1-30;
Wherein * indicates the position that structure is connected with acridine female ring shown in A-1~A-11.
2. it is according to claim 1 containing unsaturated nitrogenous heterocyclic acridine compound,
Wherein Ar1It is selected from:Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl,
Cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl;
The aliphatic alkyl of carbon atoms 1-30 is selected from:Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl
Base, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl;
The aliphatic alkoxy of carbon atoms 1-30 is selected from:Methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy,
Heptan oxygroup, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies;
The aromatic radical of carbon atom 6-20 being made of carbon and hydrogen is selected from:Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene;
Ar2It is selected from:Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, dibenzofuran group, benzo
Benzofuranyl, dinaphtho furyl;
The Ar2It can be by methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, ring fourth
It is base, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, pungent
Oxygroup, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies, phenyl, biphenyl
Base, naphthalene, anthryl, phenanthryl, triphenylene substitution.
3. according to claim 1 contain unsaturated nitrogenous heterocyclic acridine compound, Ar1, Ar2It can be by carbon containing original
The aliphatic alkyl of sub- 1-30, the aliphatic alkoxy of carbon atoms 1-30 are replaced, wherein the substitution, can singly take
Generation, it is disubstituted or polysubstituted.
4. it is according to claim 1 containing unsaturated nitrogenous heterocyclic acridine compound, selected from lower structure:
5. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device contains claim 1-4
Described contains unsaturated nitrogenous heterocyclic acridine compound.
6. organic electroluminescence device according to claim 5, which is characterized in that the organic electroluminescence device has
The material of main part of machine luminescent layer, the material of hole transmission layer, electron transfer layer material to be that claim 1-4 is any described containing
There is unsaturated nitrogenous heterocyclic acridine compound.
7. organic electroluminescence device according to claim 6, which is characterized in that the organic luminous layer is blue-light-emitting
Layer, green light emitting layer, Yellow luminous layer or red light emitting layer.
8. a kind of display device, which is characterized in that include the organic electroluminescence device as described in claim 5~7 is any.
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Cited By (4)
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CN109206416A (en) * | 2018-09-17 | 2019-01-15 | 宁波卢米蓝新材料有限公司 | A kind of acridan derivative and its preparation method and application |
CN109232419A (en) * | 2018-09-17 | 2019-01-18 | 宁波卢米蓝新材料有限公司 | A kind of acridan derivative and its preparation method and application |
CN109456296A (en) * | 2018-10-29 | 2019-03-12 | 吉林奥来德光电材料股份有限公司 | A kind of luminous organic material, preparation method and application |
CN115490624A (en) * | 2021-06-18 | 2022-12-20 | 北京绿人科技有限责任公司 | Organic compound containing azetidine and organic electroluminescent device |
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CN103503188A (en) * | 2011-05-05 | 2014-01-08 | 默克专利有限公司 | Compounds for electronic devices |
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CN109206416A (en) * | 2018-09-17 | 2019-01-15 | 宁波卢米蓝新材料有限公司 | A kind of acridan derivative and its preparation method and application |
CN109232419A (en) * | 2018-09-17 | 2019-01-18 | 宁波卢米蓝新材料有限公司 | A kind of acridan derivative and its preparation method and application |
WO2020056860A1 (en) * | 2018-09-17 | 2020-03-26 | 宁波卢米蓝新材料有限公司 | 9,10-dihydroacridine derivative, preparation method and application thereof |
WO2020056859A1 (en) * | 2018-09-17 | 2020-03-26 | 宁波卢米蓝新材料有限公司 | 9,10-dihydroacridine derivative, preparation method therefor and use thereof |
US11158814B2 (en) | 2018-09-17 | 2021-10-26 | Ningbo Lumilan Advanced Materials Co., Ltd | 9,10-dihydro-acridine derivative, and preparation method and use thereof |
US11393982B2 (en) | 2018-09-17 | 2022-07-19 | Ningbo Lumilan Advanced Materials Co., Ltd. | 9,10-dihydro-acridine derivative, and preparation method and use thereof |
CN109456296A (en) * | 2018-10-29 | 2019-03-12 | 吉林奥来德光电材料股份有限公司 | A kind of luminous organic material, preparation method and application |
CN115490624A (en) * | 2021-06-18 | 2022-12-20 | 北京绿人科技有限责任公司 | Organic compound containing azetidine and organic electroluminescent device |
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