CN108456142A - Phenyl indene compounds, organic electroluminescence device and display device - Google Patents

Phenyl indene compounds, organic electroluminescence device and display device Download PDF

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CN108456142A
CN108456142A CN201810129182.0A CN201810129182A CN108456142A CN 108456142 A CN108456142 A CN 108456142A CN 201810129182 A CN201810129182 A CN 201810129182A CN 108456142 A CN108456142 A CN 108456142A
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organic electroluminescence
electroluminescence device
compound
phenyl
fluorenyl
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不公告发明人
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Wang Meini
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Wang Meini
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Abstract

The present invention relates to display technology fields, more particularly to a kind of phenyl indene compounds, organic electroluminescence device and display device.Shown in compound according to the present invention such as formula (I)：

Description

Phenyl indene compounds, organic electroluminescence device and display device
Technical field
The present invention relates to display technology fields, more particularly to a kind of phenyl indene compounds, 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 device layers, such as the functional material having can promote electronics from cathode Injection, some functional materials can promote that hole is promoted to inject from anode, and some materials can promote the transmission of charge, some materials Material can then play the role of stopping electronics or hole transport, most important a variety of colors certainly in organic electroluminescence device Luminescent material also to achieve the purpose that match with adjacent functional material, therefore, the organic electroluminescent of excellent in efficiency long lifespan Device is 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 knots The functionalization material of structure 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 and hole injection layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And The material of hole transmission layer or hole injection layer in the prior art makes organic electroluminescence device have higher driving voltage With lower luminous efficiency.
Invention content
The present invention provides a kind of phenyl indene compounds, the organic electroluminescence device comprising the compound and with this The display device of organic electroluminescence device, to solve the high driving voltage of organic electroluminescence device in the prior art and low The problem of luminous efficiency.
According to an aspect of the present invention, a kind of phenyl indene compounds are provided, shown in the compound such as formula (I)：
Ar1,Ar2,Ar3,Ar4,Ar5,Ar6It is 6~30 to be made of carbon and hydrogen to be separately selected from total carbon atom number Aryl radical.
Another aspect of the present invention, in formula (I) described compound, Ar1,Ar2,Ar3,Ar4,Ar5,Ar6Selected from B-1：
Wherein, Ar7、Ar8、Ar9Separately it is selected from the aromatic hydrocarbon being made of carbon and hydrogen that total carbon atom number is 6~30 Base, m are selected from 0 or 1；Wherein * indicates the position that B-1 is connected with N atoms in compound shown in formula (I)；Ar8、Ar9It can connect Cyclization.
Wherein Ar8、Ar9Cyclization can be connected, is illustrated below：
Work as Ar8、Ar9When selected from phenyl, and without connecting cyclization, compound shown in B-2 is as follows：
Work as Ar8、Ar9When connection cyclization, compound shown in B-2 is as follows：
Further, the aryl radical being made of carbon and hydrogen that total carbon atom number of the present invention is 6~30 is selected from：Benzene Base, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentano are luxuriant and rich with fragrance Base, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
Optionally, phenyl indene compounds according to the present invention are selected from：
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided Including phenyl indene compounds according to the present invention.
Further, the material of the hole transmission layer of the organic electroluminescence device or hole injection layer is according to this hair Bright phenyl indene compounds.
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.
The present invention also provides a kind of electronic equipment, contain display device of the present invention.
Further, electronic equipment be selected from mobile phone, computer, tablet computer, wrist-watch, VR displays, digital camera, bracelet, Counter, electronic watch.
The present invention also provides compounds shown in formula M-04：
In addition the application the present invention also provides compound shown in M-04 in synthesizing compound shown in formula (I) of the present invention.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used in the hole transmission layer of organic electroluminescence device or the material of hole injection layer 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
Reaction equation is as follows：
(1) synthesis of intermediate M-02：
In 1000 milliliters of there-necked flasks, 300 milliliters of dichloromethane, chemical combination shown in 25.2 grams of (0.1mol) formula M-01 is added Object, 20 milliliters of dichloromethane solutions of control temperature 0~10 DEG C of dropwise addition, 17.6 grams of (0.11mol) bromines, is added dropwise, slowly rises Temperature to 30 DEG C react 2 hours, cooling, reaction solution is poured into 800 milliliters of water, liquid separation, organic layer is concentrated to dryness, absolute ethyl alcohol weight Crystallization, obtains 20.8 grams of product shown in formula M-02, yield 62.84%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-02, has obtained the m/e of product：330/332.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-02, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 7.31 (s, 1H), δ 7.28 (m, 1H), δ 7.26~7.20 (m, 4H), δ 6.73 (s, 1H), δ 5.42 (s, 1H), δ 2.18 (d, 1H), δ 1.99 (d, 1H), δ 1.70 (s, 3H), δ 0.92 (s, 6H).
(2) synthesis of intermediate M-03：
In 500 milliliters of there-necked flasks, compound shown in 16.55 grams of (0.05mol) formula M-02,200 milliliters of dichloromethanes are added Alkane, 4.74 grams of (0.06mol) pyridines, is cooled to 0 DEG C, and 20 milliliters of 16.92 grams of (0.06mol) trifluoromethanesulfanhydride anhydrides are slowly added dropwise Dichloromethane solution, finish be to slowly warm up to 25 DEG C react 4 hours.100 milliliters of moisture liquid are slowly added to, organic layer is concentrated under reduced pressure To doing, absolute ethyl alcohol recrystallization obtains 12.6 grams of product shown in formula M-03, yield 54.43%.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-03, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 7.65 (s, 1H), δ 7.40 (s, 1H), δ 7.33~7.20 (m, 5H), δ 2.21 (d, 1H), δ 2.01 (d, 1H), δ 1.72 (s, 3H), δ 0.92 (s, 6H).
(3) synthesis of intermediate M-04：
In 100 milliliters of there-necked flasks, compound shown in 4.63 grams of (0.01mol) formula M-03,30 milliliters of 1,2-, bis- chloroethenes are added Alkane, under stirring, 25~30 DEG C of mixtures that 1.5 gram of 60% nitric acid and 2.0 gram of 98% concentrated sulfuric acid is added dropwise of control temperature are finished, are protected Temperature reaction 2 hours adds moisture liquid, organic layer washing, sodium hydroxide solution washing to wash, and 60 DEG C of water-baths are concentrated into close dry, ethyl alcohol Recrystallization, obtains 1.9 grams of compound shown in formula M-04, yield 37.4%.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-04, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 8.16 (m, 2H), δ 7.60 (s, 1H), δ 7.50 (m, 2H), δ 7.44 (s, 1H), δ 2.18 (d, 1H), δ 2.02 (d, 1H), δ 1.72 (s, 3H), δ 0.91 (s, 6H).
(4) synthesis of intermediate M-05：
In 250 milliliters of there-necked flask, under nitrogen protection, be added 100 milliliters of dry toluene, 5.08 grams Compound shown in (0.01mol) formula M-04,3.72 grams of (0.022mol) diphenylamines, 2.3 grams of (0.024mol) sodium tert-butoxides, 0.28 Gram (0.0005mol) bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-tert-butylphosphine toluene solution, add Heat is down to room temperature after 24 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 9：1) it is eluted as eluant, eluent, obtains formula 1.8 grams of product shown in M-05, yield 29.27%.
To obtained compound M-05, Mass Spectrometer Method, product m/e are carried out：615.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-05, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 8.17 (m, 2H), δ 7.55 (m, 2H), δ 7.26 (m, 8H), δ 7.08 (m, 8H), δ 7.00 (m, 4H), δ 6.75 (s, 2H), δ 2.25 (d, 1H), δ 2.08 (d, 1H), δ 1.72 (s, 3H), δ 0.91 (s, 6H).
(5) synthesis of intermediate M-06：
In 500 milliliters of autoclaves, 200 milliliters of ethyl alcohol of addition, compound shown in 6.15 grams of (0.01mol) formula M-05,0.4 gram 5% Pd/C controls temperature 60 C, and pressure 0.2MPa carries out hydro-reduction reaction, and reaction finishes, and cools down, nitrogen displacement, reaction It after liquid filtering, is concentrated to dryness, ethyl alcohol and toluene Mixed Solvent recrystallization, obtaining 5.06 grams of product, yield shown in formula M-06 is 86.5%.
To obtained compound M-06, Mass Spectrometer Method, product m/e are carried out：585.
(6) synthesis of compound P-1：
In 500 milliliters of there-necked flask, under nitrogen protection, be added 200 milliliters of dry toluene, 5.85 grams Compound shown in (0.01mol) formula M-06,7.78 grams of (0.024mol) 4- bromines triphenylamines, 2.3 grams of (0.024mol) sodium tert-butoxides, 0.28 gram (0.0005mol) bis- (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-tert-butylphosphine toluene it is molten Liquid is down to room temperature after being heated to back flow reaction 24 hours, dilute hydrochloric acid, liquid separation is added, and neutrality is washed with water in organic layer, and use is anhydrous After magnesium sulfate drying, with silica gel post separation, petroleum ether is used：Ethyl acetate (volume ratio 9：1) it is eluted, is obtained as eluant, eluent To 6.23 grams of product shown in formula P-1, yield 58.2%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：1071.
Nuclear-magnetism detection is carried out to product shown in obtained formula P-1, the parsing data of obtained nuclear-magnetism figure are as follows：
1HNMR (500MHz, CDCl3)：δ 7.30~7.19 (m, 20H), δ 7.14 (s, 8H), δ 7.08 (m, 16H), δ 7.02 (m, 8H), δ 6.77 (s, 2H), δ 2.18 (d, 1H), δ 1.73 (s, 3H), δ 1.68 (d, 1H), δ 0.91 (s, 6H).
The synthesis of compound P-2
The synthetic method of reference compound P-1 only changes diphenylamines therein into N- (1- naphthalenes) aniline.To what is obtained Compound P-2 carries out Mass Spectrometer Method, product m/e：1172.
The synthesis of compound P-3
The synthetic method of reference compound P-1 only changes diphenylamines therein into N- phenyl -9,9- dimethyl fluorenes -2- Amine.To obtained compound P-3, Mass Spectrometer Method, product m/e are carried out：1305.
The synthesis of compound P-4
The synthetic method of reference compound P-1 only changes diphenylamines therein into N- (4- (9,9- dimethyl fluorene -2- Base) phenyl) aniline.To obtained compound P-4, Mass Spectrometer Method, product m/e are carried out：1457.
The synthesis of compound P-5
The synthetic method of reference compound P-1 only changes diphenylamines therein into N- phenyl -9,9- diphenylfluorenes -2- Amine.To obtained compound P-5, Mass Spectrometer Method, product m/e are carried out：1553.
The synthesis of compound P-6
The synthetic method of reference compound P-1 only changes diphenylamines therein bis- (9,9- dimethyl fluorene -2- bases) into Amine.To obtained compound P-6, Mass Spectrometer Method, product m/e are carried out：1537.
The synthesis of compound P-7
The synthetic method of reference compound P-1 only changes 4- bromines triphenylamine therein into the bromo- N of 4'-, N- diphenyl- [1,1'- biphenyl] -4- amine.To obtained compound P-7, Mass Spectrometer Method, product m/e are carried out：1224.
The synthesis of compound P-8
The synthetic method of reference compound P-1 only changes diphenylamines therein into N- (1- naphthalenes) aniline, will be therein 4- bromine triphenylamines change bromo- 9,9- dimethyl-N, N- diphenyl-fluorenes -2- amine of 7- into.To obtained compound P-8, mass spectrum inspection is carried out It surveys, product m/e：1405.
The synthesis of compound P-9
The synthetic method of reference compound P-8 only changes 4- bromines triphenylamine therein into 9- (bromo- 9, the 9- dimethyl-of 7- Fluorenes -2- bases)-carbazole.To obtained compound P-9, Mass Spectrometer Method, product m/e are carried out：1401.
The synthesis of compound P-10
The synthetic method of reference compound P-8 only changes 4- bromines triphenylamine therein into 9- (bromo- 9, the 9- diphenyl-of 7- Fluorenes -2- bases)-carbazole.To obtained compound P-10, Mass Spectrometer Method, product m/e are carried out：1649.
The synthesis of compound P-11
The synthetic method of reference compound P-1 only changes diphenylamines therein into N- ([1,1'- biphenyl] -3- bases) -9, 9- dimethyl-fluorenes -2- amine changes 4- bromines triphenylamine therein into N4- (4- bromophenyls)-N4, N4', N4'- triphenyls-[1,1'- Biphenyl] -4,4'- diamines.To obtained compound P-11, Mass Spectrometer Method, product m/e are carried out：1943.
The synthesis of compound P-12
The synthetic method of reference compound P-11, only by N4- therein (4- bromophenyls)-N4, N4', N4'- triphenyls- [1,1'- biphenyl] -4,4'- diamines changes N2- (4- bromophenyls) -9,9- dimethyl-N2, N7, N7- triphenyl-fluorenes -2,7- two into Amine.To obtained compound P-12, Mass Spectrometer Method, product m/e are carried out：2023.
The synthesis of compound P-13
(1) synthesis of intermediate M-02：
In 1000 milliliters of there-necked flasks, 300 milliliters of dichloromethane, chemical combination shown in 25.2 grams of (0.1mol) formula M-01 is added Object, 20 milliliters of dichloromethane solutions of control temperature 0~10 DEG C of dropwise addition, 17.6 grams of (0.11mol) bromines, is added dropwise, slowly rises Temperature to 30 DEG C react 2 hours, cooling, reaction solution is poured into 800 milliliters of water, liquid separation, organic layer is concentrated to dryness, absolute ethyl alcohol weight Crystallization, obtains 20.8 grams of product shown in formula M-02, yield 62.84%.
Mass Spectrometer Method has been carried out to product shown in obtained formula M-02, has obtained the m/e of product：330/332.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-02, obtained nuclear-magnetism parsing data are as follows：
1HNMR (500MHz, CDCl3)：δ 7.31 (s, 1H), δ 7.28 (m, 1H), δ 7.26~7.20 (m, 4H), δ 6.73 (s, 1H), δ 5.42 (s, 1H), δ 2.18 (d, 1H), δ 1.99 (d, 1H), δ 1.70 (s, 3H), δ 0.92 (s, 6H).
(2) synthesis of intermediate M-03：
In 500 milliliters of there-necked flasks, compound shown in 16.55 grams of (0.05mol) formula M-02,200 milliliters of dichloromethanes are added Alkane, 4.74 grams of (0.06mol) pyridines, is cooled to 0 DEG C, and 20 milliliters of 16.92 grams of (0.06mol) trifluoromethanesulfanhydride anhydrides are slowly added dropwise Dichloromethane solution, finish be to slowly warm up to 25 DEG C react 4 hours.100 milliliters of moisture liquid are slowly added to, organic layer is concentrated under reduced pressure To doing, absolute ethyl alcohol recrystallization obtains 12.6 grams of product shown in formula M-03, yield 54.43%.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-03, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 7.65 (s, 1H), δ 7.40 (s, 1H), δ 7.33~7.20 (m, 5H), δ 2.21 (d, 1H), δ 2.01 (d, 1H), δ 1.72 (s, 3H), δ 0.92 (s, 6H).
(3) synthesis of intermediate M-08
In 1000 milliliters of there-necked flasks, 500 milliliters of dichloromethane, 100 milliliters of glacial acetic acid, 23.15 grams (0.05mol) are added Compound shown in formula M-03,4.7 grams of (0.06mol) pyridines, 0.2 gram of (0.0036mol) iron powder are added dropwise 9.6 grams in 20~25 DEG C 10 milliliters of dichloromethane solutions of (0.06mol) bromine finish 20~25 DEG C of holding and react 6 hours.Washing, sodium hydrogensulfite are molten Liquid washs, pillar layer separation, ethyl acetate：Petroleum ether=1：15 (volume ratios) elute, and obtain 13.5 grams of product shown in formula M-08, Yield 49.8%.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-08, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 7.74 (m, 2H), δ 7.53 (s, 1H), δ 7.43 (s, 1H), δ 7.13 (m, 2H), δ 2.15 (d, 1H), δ 2.02 (d, 1H), δ 1.72 (s, 3H), δ 0.92 (s, 6H).
(4) synthesis of compound P-13：
In 500 milliliters of there-necked flask, under nitrogen protection, be added 220 milliliters of dry toluene, 5.42 grams Compound shown in (0.01mol) formula M-08,5.58 grams of (0.033mol) diphenylamines, 3.8 grams of (0.04mol) sodium tert-butoxides, 0.42 Gram (0.00075mol) bis- (dibenzalacetone) palladiums, 3.03 grams of (0.0015mol) 10% tri-tert-butylphosphine toluene solution, It is down to room temperature after being heated to back flow reaction 24 hours, dilute hydrochloric acid is added, liquid separation, neutrality is washed with water in organic layer, with anhydrous sulphur After sour magnesium drying, with silica gel post separation, petroleum ether is used：Ethyl acetate (volume ratio 7：3) it is eluted, is obtained as eluant, eluent 3.8 grams of product shown in formula P-13, yield 51.6%.
To obtained compound P-13, Mass Spectrometer Method, product m/e are carried out：737.
Nuclear-magnetism detection is carried out to obtained compound P-13, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 7.26 (m, 12H), δ 7.19 (m, 4H), δ 7.02 (m, 12H), δ 6.99 (m, 6H), δ 6.77 (s, 2H) δ 2.32 (d, 1H), δ 2.11 (d, 1H), δ 1.72 (s, 3H), δ 0.93 (s, 6H).
The synthesis of compound P-14
The synthetic method of reference compound P-13 only changes diphenylamines therein into N1, N1, N4- triphenylbenzene-Isosorbide-5-Nitrae- Diamines.To obtained compound P-14, Mass Spectrometer Method, product m/e are carried out：1239.
The synthesis of compound P-15
The synthetic method of reference compound P-13 only changes diphenylamines therein into N1- ([1,1'- biphenyl] -4- bases) - N4, N4- diphenyl benzene -1,4- diamines.Mass Spectrometer Method, product m/e are carried out to obtained compound P-15：1468.
The synthesis of compound P-16
The synthetic method of reference compound P-13, only by diphenylamines therein change into N4- (4'- (hexichol amido)-[1, 1'- biphenyl] -4- bases)-N4', N4'- diphenyl-[1,1'- biphenyl] -4,4'- diamines.To obtained compound P-16, matter is carried out Spectrum detection, product m/e：2197.
The synthesis of compound P-17
The synthetic method of reference compound P-13 only changes diphenylamines therein into N4- (9,9- dimethyl fluorene -2-) - [1,1'- joins N4'- (4'- ((9,9- dimethyl fluorene -2- bases) (phenyl) amido)-[1,1'- biphenyl] -4- bases)-N4- phenyl - Benzene] -4,4'- diamines.To obtained compound P-17, Mass Spectrometer Method, product m/e are carried out：2894.
The synthesis of compound P-18
The synthetic method of reference compound P-13 only changes diphenylamines therein into N- ([1,1'- biphenyl] -4- bases) - 9,9- dimethyl fluorene -2- amine.To obtained compound P-18, Mass Spectrometer Method, product m/e are carried out：1315.
The synthesis of compound P-19
The synthetic method of reference compound P-13 only changes diphenylamines therein into N- ([1,1'- biphenyl] -3- bases) - 9,9- dimethyl fluorene -2- amine.To obtained compound P-19, Mass Spectrometer Method, product m/e are carried out：1315.
The synthesis of compound P-20
The synthetic method of reference compound P-13 only changes diphenylamines therein into N- ([1,1'- biphenyl] -4- bases) - Two fluorenes -2- amine of 9,9'- spiral shells.To obtained compound P-20, Mass Spectrometer Method, product m/e are carried out：1681.
The synthesis of compound P-21
The synthetic method of reference compound P-13 only changes diphenylamines therein into N- phenyl phenanthrene -9- amine.To what is obtained Compound P-21 carries out Mass Spectrometer Method, product m/e：1037.
The synthesis of compound P-22
The synthetic method of reference compound P-13 only changes diphenylamines therein into N- phenyl triphenylene -2- amine.To The compound P-22 arrived carries out Mass Spectrometer Method, product m/e：1188.
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device The material of hole transmission layer or hole injection layer is according to the compound of the present invention.
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 concrete structure of material therefor is seen below in embodiment：
Embodiment 1
Hole mobile material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison Electroluminescence device, hole mobile material select NPB, H-1, H-2, H-3, H-5 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 TAZ makees electron injection as electron transport layer materials, LiF/Al 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 1：
Table 1
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as hole transmission layer by upper table The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 2
Hole mobile material in using the compound of the present invention as organic electroluminescence device, as a comparison organic Electroluminescent device, hole-injecting material select HIL02, H-1, H-4, H-5.
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, NPB makees empty Cave transport layer, EM1 make the material of main part of organic luminous layer, TAZ as electron transport layer materials, LiF/Al make 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 Hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness are 100nm.
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.
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 2：
Table 2
Organic electroluminescence it can be seen that, can be improved using the compound of the present invention as hole injection 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 (10)

1. a kind of phenyl indene compounds, as shown in formula (I)：
Wherein, Ar1,Ar2,Ar3,Ar4,Ar5,Ar6It is 6~30 to be made of carbon and hydrogen to be separately selected from total carbon atom number Aryl radical.
2. a kind of phenyl indene compounds according to claim 1, which is characterized in that wherein, Ar1,Ar2,Ar3,Ar4, Ar5,Ar6Separately it is selected from B-1：
Wherein, Ar7、Ar8、Ar9Separately it is selected from the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30, m Selected from 0 or 1；
Wherein * indicates the position that B-1 is connected with N atoms in compound shown in formula (I)；
Ar8、Ar9Cyclization can be connected.
3. a kind of phenyl indene compounds according to claim 1, total carbon atom number is 6~30 to be made of carbon and hydrogen Aryl radical is selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indenes And fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
4. a kind of phenyl indene compounds according to claim 2, wherein total carbon atom number are 6~30 by carbon and hydrogen group At aryl radical be selected from：
Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, ring Penta and phenanthryl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
Phenyl indene compounds below 5.：
6. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes claim 1-5 any The phenyl indene compounds.
7. organic electroluminescence device according to claim 6, which is characterized in that the hole of the organic electroluminescence device The material of transport layer or hole injection layer is any phenyl indene compounds of claim 1-5.
8. a kind of display device, which is characterized in that include the organic electroluminescence device as described in claim 6~7 is any.
9. a kind of electronic equipment, including display device described in claim 8, the electronic equipment is selected from mobile phone, computer, tablet electricity Brain, wrist-watch, VR displays, digital camera, bracelet, counter, electronic watch.
10. compound shown in formula M-04：
CN201810129182.0A 2018-02-08 2018-02-08 Phenyl indene compounds, organic electroluminescence device and display device Withdrawn CN108456142A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7489977B2 (en) 2018-11-09 2024-05-24 ドッティコン エーエス ホールディング アクチェン ゲゼルシャフト Di-, tri- and tetraphenylindane derivatives and their use in organic electronics - Patents.com

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7489977B2 (en) 2018-11-09 2024-05-24 ドッティコン エーエス ホールディング アクチェン ゲゼルシャフト Di-, tri- and tetraphenylindane derivatives and their use in organic electronics - Patents.com

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