CN108218867A - A kind of compound, organic electroluminescence device and display device - Google Patents
A kind of compound, organic electroluminescence device and display device Download PDFInfo
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Abstract
The present invention relates to a kind of display field more particularly to compound, organic electroluminescence device and display devices.The compound is shown in formula I：
Description
Technical field
The present invention relates to a kind of display field more particularly to compound, organic electroluminescence device and display devices.
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 adjusted, is at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, raw
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 in organic semiconductor, the transmission of carrier is normal
It is described with jump theory.In order to which organic electroluminescence device is made to 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 device 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.Certainly in organic electroluminescence device, most important a variety of colors
Luminescent material will also achieve the purpose that match with adjacent functional material.Therefore, the organic electroluminescence of efficient long lifespan
Part is typically device architecture and various organic materials optimize arranging in pairs or groups as a result, this just designs and develops various structures for chemists
Functionalization material provide great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode being arranged in order from top to bottom, electron injecting layer, electronics
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 electronics adjacent thereto pass
The material of defeated layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.It is and of the prior art
The material of main part and electron transport material of organic luminous layer make organic electroluminescence device have higher driving voltage and relatively low
Luminous efficiency.
Invention content
The present invention provides a kind of 1H- imidazos [4,5-f] [1,10] ferrosin class compound, having comprising the compound
Organic electroluminescence devices and the display device with the organic electroluminescence device, solve organic electroluminescent in the prior art
The problem of high driving voltage of device and low luminous efficiency.
According to an aspect of the present invention, a kind of compound is provided, the compound is shown in formula I：
Wherein, X group is selected from carbazyl, acridan base, dihydrophenazine base, phenoxazine groups, phenothiazinyl, benzopyrrole
And carbazyl, benzofuran and carbazyl, benzothiophene and carbazyl, indeno carbazyl or triphenylamine base, the X group is takes
It is generation or unsubstituted；A groups are selected from the aryl that carbon atom number is 6-30, the alkyl that carbon atom is 1-20 or carbon atom number
For the cycloalkyl of 3-20, the A groups are substitution or unsubstituted.
According to embodiment of the present invention, in A groups, the aryl is selected from：Phenyl, xenyl, terphenyl, naphthalene
Base, binaphthyl, anthryl, dianthranide base, diphenyl anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, ring penta
And phenanthryl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl or benzo anthryl.
According to embodiment of the present invention, X group is substitution, and substituent group is selected from the alkane that carbon atom number is 1-20
Base, the cycloalkyl that carbon atom number is 3-20, phenyl, xenyl, terphenyl, naphthalene, binaphthyl, anthryl, dianthranide base, diphenyl
Anthryl, benzo dihydro anthryl, phenanthryl, dihydrophenanthrenyl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentano are luxuriant and rich with fragrance
One or more of base, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl and benzo anthryl.
According to embodiment of the present invention, A groups are substitution, and substituent group is selected from the alkane that carbon atom number is 1-20
Cycloalkyl, phenyl, xenyl, naphthalene, fluorenyl and the anthryl that alkoxy that base, carbon atom number are 1-20, carbon atom number are 3-20
One or more of.
According to embodiment of the present invention, the compound is selected from：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided
Including compound according to the present invention.
According to embodiment of the present invention, the phosphorescence host material of the organic luminous layer of the organic electroluminescence device
The material of material and/or electron transfer layer is according to the compound of the present invention.
According to embodiment of the present invention, the phosphorescent light body material is red phosphorescent material of main part or green phosphorescent
Material of main part.
According to another aspect of the present invention, a kind of display device is provided, the display device includes according to the present invention
Organic electroluminescence device.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used as to the material of main part and/or electricity of the organic luminous layer of organic electroluminescence device
The material of sub- transport layer improves the luminous efficiency of organic electroluminescence device, reduces the driving of organic electroluminescence device
Voltage.
Specific embodiment
Specific embodiment is only the description of the invention, without forming the limitation to the content of present invention, below in conjunction with
Specific embodiment is further described and describes to the present invention.
According to an aspect of the present invention, a kind of compound is provided, the compound is shown in formula I：
Wherein, X group is selected from carbazyl, acridan base, dihydrophenazine base, phenoxazine groups, phenothiazinyl, benzopyrrole
And carbazyl, benzofuran and carbazyl, benzothiophene and carbazyl, indeno carbazyl or triphenylamine base, the X group is takes
It is generation or unsubstituted；A groups are selected from the aryl that carbon atom number is 6-30, the alkyl that carbon atom is 1-20 or carbon atom number
For the cycloalkyl of 3-20, the A groups are substitution or unsubstituted.
Compound provided by the invention is used as to the material of main part and/or electricity of the organic luminous layer of organic electroluminescence device
The material of sub- transport layer improves the luminous efficiency of organic electroluminescence device, reduces the driving of organic electroluminescence device
Voltage.
According to embodiment of the present invention, in A groups, the aryl is selected from：Phenyl, xenyl, terphenyl, naphthalene
Base, binaphthyl, anthryl, dianthranide base, diphenyl anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, ring penta
And phenanthryl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl or benzo anthryl.
According to embodiment of the present invention, X group is substitution, and substituent group is selected from the alkane that carbon atom number is 1-20
Base, the cycloalkyl that carbon atom number is 3-20, phenyl, xenyl, terphenyl, naphthalene, binaphthyl, anthryl, dianthranide base, diphenyl
Anthryl, benzo dihydro anthryl, phenanthryl, dihydrophenanthrenyl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentano are luxuriant and rich with fragrance
One or more of base, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl and benzo anthryl.
According to embodiment of the present invention, A groups are substitution, and substituent group is selected from the alkane that carbon atom number is 1-20
Cycloalkyl, phenyl, xenyl, naphthalene, fluorenyl and the anthryl that alkoxy that base, carbon atom number are 1-20, carbon atom number are 3-20
One or more of.
X group can be unsubstituted, for example, X group can be triphenylamine base, carbazyl, acridan base, dihydro fen
Piperazine base, phenoxazine groups, phenothiazinyl, benzopyrrole and carbazyl, benzofuran and carbazyl, benzothiophene and carbazyl or indenes
And carbazyl.
X can may be substituted, and substitution mode can be monosubstituted, two substitutions or polysubstituted.
When the mode of substitution is two substitution, two substituent groups can be each independently selected from the alkane that carbon atom number is 1-20
Base, the cycloalkyl that carbon atom number is 3-20, phenyl, xenyl, terphenyl, naphthalene, binaphthyl, anthryl, dianthranide base, diphenyl
Anthryl, benzo dihydro anthryl, phenanthryl, dihydrophenanthrenyl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentano are luxuriant and rich with fragrance
Base, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
When the mode of substitution is polysubstituted, multiple substituent groups can be each independently selected from the alkane that carbon atom number is 1-20
Base, the cycloalkyl that carbon atom number is 3-20, phenyl, xenyl, terphenyl, naphthalene, binaphthyl, anthryl, dianthranide base, diphenyl
Anthryl, benzo dihydro anthryl, phenanthryl, dihydrophenanthrenyl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentano are luxuriant and rich with fragrance
Base, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
I.e.：When the mode of substitution is two substitution, two substituent groups may be the same or different.A for example, substituent group
For methyl, another substituent group is ethyl；One substituent group is propyl, and another substituent group is phenyl；Two substituent groups are butyl；
Two substituent groups are naphthalene etc..Similarly, when the mode of substitution is polysubstituted, between multiple substituent groups can it is identical,
Entirely different or part is identical.For example, the first substituent group is fluorenyl, the second substituent group is phenyl, third substituent group is anthryl；
First substituent group is phenyl, the second substituent group is fluoranthene base, third substituent group is indeno fluorenyl；First substituent group is ethyl, the
Disubstituted is ethyl, third substituent group is phenyl；Three substituent groups are methyl；Three substituent groups are phenyl etc..
Similarly, A groups can be unsubstituted carbon atom number be 6-30 aryl, unsubstituted carbon atom be 1-20's
Alkyl or unsubstituted carbon atom number are the cycloalkyl of 3-20, for example, A groups can be methyl, ethyl, propyl, isopropyl,
Butyl, isobutyl group, amyl, isopentyl, neopentyl, hexyl, cyclopropyl, cyclopenta, cyclohexyl, phenyl, xenyl, terphenyl
Base, naphthalene, binaphthyl, anthryl, dianthranide base, diphenyl anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indenofluorene
Base, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
A groups can also be substitution carbon atom number be 6-30 aryl, substitution carbon atom be 1-20 alkyl or
Substituted carbon atom number is the cycloalkyl of 3-20, and substitution mode can be monosubstituted, two substitutions or polysubstituted.
When the mode of substitution is two substitution, two substituent groups can be each independently selected from the alkane that carbon atom number is 1-20
Cycloalkyl that alkoxy that base, carbon atom number are 1-20, carbon atom number are 3-20, phenyl, xenyl, naphthalene, fluorenyl, anthryl.
When the mode of substitution is polysubstituted, multiple substituent groups can be each independently selected from the alkane that carbon atom number is 1-20
Cycloalkyl that alkoxy that base, carbon atom number are 1-20, carbon atom number are 3-20, phenyl, xenyl, naphthalene, fluorenyl, anthryl.
I.e.：When the mode of substitution is two substitution, two substituent groups may be the same or different.A for example, substituent group
For methyl, another substituent group is cyclopropyl；One substituent group is propyl, and another substituent group is phenyl；Two substituent groups are fourth
Base；Two substituent groups are naphthalene etc..It similarly, can complete phase between multiple substituent groups when the mode of substitution is polysubstituted
It is identical with, entirely different or part.For example, the first substituent group is fluorenyl, the second substituent group is phenyl, third substituent group is anthracene
Base；First substituent group is phenyl, the second substituent group is naphthalene, third substituent group is xenyl；First substituent group is ethyl, second
Substituent group is ethyl, third substituent group is phenyl；Three substituent groups are methyl；Three substituent groups are phenyl etc..
It should be noted that in the technical scheme, functional group (refers to triphenylamine base, carbazyl, acridan base, dihydro
Phenazinyl, phenoxazine groups, phenothiazinyl, benzopyrrole and carbazyl, benzofuran and carbazyl, benzothiophene and carbazyl or
Indeno carbazyl) on substituent group can be connected with any position with any position of the functional group, the substituent group in functional group
It can also be connected with any position with 1H- imidazos [4,5-f] [1,10] ferrosin base；In addition, functional group (refer to triphenylamine base,
Carbazyl, acridan base, dihydrophenazine base, phenoxazine groups, phenothiazinyl, benzopyrrole and carbazyl, benzofuran and click
Oxazolyl, benzothiophene and carbazyl or indeno carbazyl) it can also be luxuriant and rich with fragrance with any position and 1H- imidazos [4,5-f] [1,10]
Hello quinoline base is connected；As long as the compound obtained according to these connection modes can be prepared.
According to embodiment of the present invention, the compound is selected from：Compound P-1 to compound P-30.
In order to which the compound of the present invention is explained in more detail, synthetic method pair that will enumerate above-mentioned particular compound below
The present invention is further described.
The synthesis of compound P-1
In 1000 milliliters of there-necked flasks, 500 milliliters of acetic acid are added in, under nitrogen protection, add in 21 grams (0.1mol) adjacent luxuriant and rich with fragrance hello
Quinoline -5,6- diketone, 14.95 grams of (0.05mol) 9- phenyl carbazole -3,6- dialdehyde, 13.9 grams of (0.15mol) aniline, 15.4 grams
(0.2mol) ammonium acetate, is to slowly warm up to back flow reaction 8 hours, and cooling is poured into 3000 milliliters of water, is filtered.Obtained solid is done
After dry, silica gel column chromatography separation, dichloromethane：Ethyl acetate：Petroleum ether=2：3：5 elutions, obtain product 62.8 shown in formula P-1
Gram, HP-LC 99.3%, yield 75.6%.
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e of product：831 (100%).
Nuclear-magnetism detection is carried out to product shown in obtained formula P-1, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 8.80 (m, 4H), δ 8.13 (m, 6H), δ 7.88 (m, 1H), δ 7.71 (d,
1H), δ 7.66~7.56 (m, 6H), δ 7.53~7.44 (m, 7H), δ 7.43~7.36 (m, 8H).
The synthesis of compound P-2
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9- biphenyl
Base carbazole -3,6- dialdehyde obtains corresponding compound P-2.
Compound P-2 is obtained, carries out Mass Spectrometer Method, product m/e：907.
The synthesis of compound P-3
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9- (2-
Naphthalene) carbazole -3,6- dialdehyde, obtain corresponding compound P-3.
Compound P-3 is obtained, carries out Mass Spectrometer Method, product m/e：881.
The synthesis of compound P-4
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9- ethyls
Carbazole -3,6- dialdehyde obtains corresponding compound P-4.
Compound P-4 is obtained, carries out Mass Spectrometer Method, product m/e：783.
The synthesis of compound P-5
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9- benzyls
Carbazole -3,6- dialdehyde obtains corresponding compound P-5.
Compound P-5 is obtained, carries out Mass Spectrometer Method, product m/e：845.
The synthesis of compound P-6
The synthesis of synthetic method reference compound P-1, only changes aniline therein into 4- methylanilines, obtains corresponding
Compound P-6.
Compound P-6 is obtained, carries out Mass Spectrometer Method, product m/e：859.
The synthesis of compound P-7
The synthesis of synthetic method reference compound P-1, only changes aniline therein into benzidine, to corresponding compound
P-7。
Compound P-7 is obtained, carries out Mass Spectrometer Method, product m/e：983.
The synthesis of compound P-8
The synthesis of synthetic method reference compound P-1, only changes aniline therein into naphthalidine, obtains corresponding chemical combination
Object P-8.
Compound P-8 is obtained, carries out Mass Spectrometer Method, product m/e：931.
The synthesis of compound P-9
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 5,11-
Diphenyl -5,11- indoline simultaneously [3,2-b] carbazole -2,8- dicarbaldehyde, obtains corresponding compound P-9.
Compound P-9 is obtained, carries out Mass Spectrometer Method, product m/e：996.
The synthesis of compound P-10
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 5,11-
Two (4- aminomethyl phenyls) -5,11- indoline simultaneously [3,2-b] carbazole -2,8- dicarbaldehyde, obtains corresponding compound P-10.
Compound P-10 is obtained, carries out Mass Spectrometer Method, product m/e：1024.
The synthesis of compound P-11
The synthesis of synthetic method reference compound P-9, only changes aniline therein into benzidine, obtains corresponding chemical combination
Object P-11.
Compound P-11 is obtained, carries out Mass Spectrometer Method, product m/e：1148.
The synthesis of compound P-12
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9,9- bis-
Methyl-1 0- phenyl -9,10- acridan -2,7- dicarbaldehydes, obtain corresponding compound P-12.
Compound P-12 is obtained, carries out Mass Spectrometer Method, product m/e：873.
The synthesis of compound P-13
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9,9- bis-
Phenyl -10- phenyl -9,10- acridan -2,7- dicarbaldehydes, obtain corresponding compound P-13.
Compound P-13 is obtained, carries out Mass Spectrometer Method, product m/e：997.
The synthesis of compound P-14
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into two (4-
Fonnylphenyl) aniline, obtain corresponding compound P-14.
Compound P-14 is obtained, carries out Mass Spectrometer Method, product m/e：833.
The synthesis of compound P-15
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into two (4-
Fonnylphenyl) 4- methylanilines, obtain corresponding compound P-15.
Compound P-15 is obtained, carries out Mass Spectrometer Method, product m/e：847.
The synthesis of compound P-16
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 11,11-
Dimethyl -5- phenyl -5,11- indoline simultaneously [1,2-b] carbazole -2,9- dicarbaldehyde, obtains corresponding compound P-16.
Compound P-16 is obtained, carries out Mass Spectrometer Method, product m/e：947.
The synthesis of compound P-17
The synthesis of synthetic method reference compound P-1, only changes aniline therein into n-butylamine, obtains corresponding chemical combination
Object P-17.
Compound P-17 is obtained, carries out Mass Spectrometer Method, product m/e：791.
The synthesis of compound P-18
The synthesis of synthetic method reference compound P-1, only changes aniline therein into cyclohexylamine, obtains corresponding chemical combination
Object P-18.
Compound P-18 is obtained, carries out Mass Spectrometer Method, product m/e：843.
The synthesis of compound P-19
The synthesis of synthetic method reference compound P-1, only changes aniline therein into 4- isopropyl anilines, obtains corresponding
Compound P-19.
Compound P-19 is obtained, carries out Mass Spectrometer Method, product m/e：915.
The synthesis of compound P-20
The synthesis of synthetic method reference compound P-1, only changes aniline therein into 4- aminoanisoles, obtains corresponding
Compound P-20.
Compound P-20 is obtained, carries out Mass Spectrometer Method, product m/e：891.
The synthesis of compound P-21
The synthesis of synthetic method reference compound P-1 only changes aniline therein into 9,9- dimethyl fluorene -2- amine, obtains
To corresponding compound P-21.
Compound P-21 is obtained, carries out Mass Spectrometer Method, product m/e：1063.
The synthesis of compound P-22
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 10- benzene
Base -10H- Fen oxazine -3,7- dicarbaldehydes, obtain corresponding compound P-22.
Compound P-22 is obtained, carries out Mass Spectrometer Method, product m/e：847.
The synthesis of compound P-23
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 10- benzene
Base -10H- phenothiazine -3,7- dicarbaldehydes, obtain corresponding compound P-23.
Compound P-23 is obtained, carries out Mass Spectrometer Method, product m/e:863.
The synthesis of compound P-24
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 5,10-
Diphenyl -5,10- dihydrophenazine -2,8- dicarbaldehyde obtains corresponding compound P-24.
Compound P-24 is obtained, carries out Mass Spectrometer Method, product m/e:922.
The synthesis of compound P-25
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 4,4'-
(azophenlyene -5,10- diyl) two benzaldehydes, obtain corresponding compound P-25.
Compound P-25 is obtained, carries out Mass Spectrometer Method, product m/e:922.
The synthesis of compound P-26
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 11- benzene
Base -11H- benzofurans simultaneously [3,2-b] carbazole -2,8- dicarbaldehyde, obtains corresponding compound P-26.
Compound P-26 is obtained, carries out Mass Spectrometer Method, product m/e:921.
The synthesis of compound P-27
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 11- benzene
Base -11H- benzothiophenes simultaneously [3,2-b] carbazole -2,8- dicarbaldehyde, obtains corresponding compound P-27.
Compound P-27 is obtained, carries out Mass Spectrometer Method, product m/e:937.
The synthesis of compound P-28
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 4,4'-
(9- phenyl -9H- carbazoles -3,6- diyl) dicarbaldehyde, obtains corresponding compound P-28.
Compound P-28 is obtained, carries out Mass Spectrometer Method, product m/e:983.
The synthesis of compound P-29
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 4,4'-
(9- ethyl -9H- carbazoles -3,6- diyl) dicarbaldehyde, obtains corresponding compound P-29.
Compound P-29 is obtained, carries out Mass Spectrometer Method, product m/e:935.
The synthesis of compound P-30
The synthesis of synthetic method reference compound P-1 only changes 9- phenyl carbazoles -3,6- dialdehyde therein into 9- (4-
Fonnylphenyl) -9H- carbazole -3- formaldehyde, obtain corresponding compound P-30.
Compound P-30 is obtained, carries out Mass Spectrometer Method, product m/e:831.
According to embodiment of the present invention, the phosphorescence host material of the organic luminous layer of the organic electroluminescence device
The material of material and/or electron transfer layer is according to the compound of the present invention.
According to embodiment of the present invention, the phosphorescent light body material is red phosphorescent material of main part or green phosphorescent
Material of main part.
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 or hole-injecting material, can vacuum evaporation formed it is pin-free thin
Film.Common 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.Common 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 by taking dyestuff as an example, needs
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.Common electron transport layer materials include 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
It is derived from arbitrary two kinds of collocation of these three materials.
According to another aspect of the present invention, a kind of display device is provided, which has including according to the present invention
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
Embodiment 1-19 selects the compound of the present invention to compare as the electron transport material in organic electroluminescence device
Embodiment 1 selects Alq3 as the electron transport material in organic electroluminescence device.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process 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
Water with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface, to improve the property on surface, is improved and is noted with hole
Enter the binding ability of 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；
Vacuum evaporation NPB is as hole transmission layer on hole injection layer, and evaporation rate 0.1nm/s, film thickness, which is deposited, is
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；
Vacuum evaporation the compounds of this invention and Alq3 are distinguished on organic luminous layer as organic electroluminescence device
Electron transfer layer；Its evaporation rate is 0.1nm/s, and vapor deposition total film thickness is 20nm；
The Al of LiF, 150nm of vacuum evaporation 0.5nm are as electron injecting layer and cathode on the electron transport layer.
Organic electroluminescence device performance is shown in Table 1.
Performance table of 1 compound according to the present invention of table as electron transport material
As can be seen that under identical brightness conditions, compound using the present invention is as organic electroluminescence device
Electron transport layer materials improve the luminous efficiency of organic electroluminescence device and reduce the drive of organic electroluminescence device
Dynamic voltage.
Embodiment 20-31 selects the compound of the present invention as the main body in red phosphorescent OLED organic electroluminescence devices
Material, comparing embodiment 2 select CBP as the material of main part in red phosphorescent OLED organic electroluminescence devices.
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
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
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；
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 LiF, 150nm of vacuum evaporation 0.5nm are as electron injecting layer and cathode on the electron transport layer.
Organic electroluminescence device performance is shown in Table 2.
Performance table of 2 compound according to the present invention of table as red phosphorescent material of main part
By upper table it can be seen that, red phosphorescent main body material of the compound using the present invention as organic electroluminescence device
Material, improves the luminous efficiency of organic electroluminescence device and reduces the driving voltage of organic electroluminescence device.
Embodiment 32-40 selects the compound of the present invention as the main body in green phosphorescent OLED organic electroluminescence devices
Material, comparing embodiment 3 select CBP as the material of main part in green phosphorescent OLED organic electroluminescence devices.
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 in commercial detergent is ultrasonically treated, is rinsed in deionized water,
In acetone：Ultrasonic oil removing in alcohol mixed solvent, is baked under clean environment and removes moisture content completely, clear with ultraviolet light and ozone
It washes, and with low energy cation beam bombarded surface；
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；
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.
Performance table of 3 compound according to the present invention of table as green phosphorescent material of main part
By upper table it can be seen that, green phosphorescent main body material of the compound using the present invention as organic electroluminescence device
Material, improves the luminous efficiency of organic electroluminescence device and 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 (9)
1. a kind of compound, which is characterized in that the compound is shown in formula I：
Wherein, X group is selected from carbazyl, acridan base, dihydrophenazine base, phenoxazine groups, phenothiazinyl, benzopyrrole and click
Oxazolyl, benzofuran and carbazyl, benzothiophene and carbazyl, indeno carbazyl or triphenylamine base, the X group are substitution
It is or unsubstituted；It is 3- that A groups, which are selected from the aryl that carbon atom number is 6-30, the alkyl that carbon atom is 1-20 or carbon atom number,
20 cycloalkyl, the A groups are substitution or unsubstituted.
2. compound according to claim 1, which is characterized in that in A groups, the aryl is selected from：Phenyl, xenyl,
Terphenyl, naphthalene, binaphthyl, anthryl, dianthranide base, diphenyl anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indenes
And fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl or benzo anthryl.
3. compound according to claim 1, which is characterized in that X group is substitution, and substituent group is selected from carbon atom number
The alkyl of 1-20, the cycloalkyl that carbon atom number is 3-20, phenyl, xenyl, terphenyl, naphthalene, binaphthyl, anthryl, dianthranide
Base, diphenyl anthryl, benzo dihydro anthryl, phenanthryl, dihydrophenanthrenyl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl,
In cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl and benzo anthryl it is a kind of with
On.
4. compound according to claim 1, which is characterized in that A groups are substitution, and substituent group is selected from carbon atom number
Cycloalkyl that alkoxy that the alkyl of 1-20, carbon atom number are 1-20, carbon atom number are 3-20, phenyl, xenyl, naphthalene, fluorenes
One or more of base and anthryl.
5. compound according to claim 1, which is characterized in that the compound is selected from：
6. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device includes claim 1-5
The compound.
7. organic electroluminescence device according to claim 6, which is characterized in that the organic electroluminescence device has
The phosphorescent light body material of machine luminescent layer and/or the material of electron transfer layer are any compounds of claim 1-5.
8. organic electroluminescence device according to claim 7, which is characterized in that the phosphorescent light body material is red phosphorus
Light material of main part or green phosphorescent material of main part.
9. a kind of display device, which is characterized in that including any organic electroluminescence devices of claim 6-8.
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