CN108456159A - 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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CN108456159A
CN108456159A CN201810129191.XA CN201810129191A CN108456159A CN 108456159 A CN108456159 A CN 108456159A CN 201810129191 A CN201810129191 A CN 201810129191A CN 108456159 A CN108456159 A CN 108456159A
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organic electroluminescence
electroluminescence device
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Wang Meini
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Wang Meini
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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 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 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)：
Selected from substituted or unsubstituted carbazyl, substituted or unsubstituted benzo carbazole base in described A1, A2, A3.
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.
Optionally, the material of main part of the organic luminous layer of the organic electroluminescence device or the material of hole transmission layer are Phenyl indene compounds according to the present invention.
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.
Meanwhile the present invention also provides a kind of electronic equipment, which contains electronic display screen.
Further, above-mentioned electronic equipment is selected from：Mobile phone, computer, tablet computer, wrist-watch, VR displays, digital camera, Bracelet, counter, electronic watch.
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-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-1：
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-08,5.51 grams of (0.033mol) carbazoles, 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, 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 7：3) it is eluted as eluant, eluent, obtains formula 4.1 grams of product shown in P-1, yield 56.08%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：731.
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, 3H), δ 8.19 (m, 3H), δ 7.92 (d, 2H), δ 7.52 (m, 3H), δ 7.39 (m, 5H), δ 7.28 (m, 2H), δ 7.26~7.08 (m, 12H), δ 2.55 (d, 1H), δ 2.31 (d, 1H), δ 1.71 (s, 3H), δ 0.93 (s, 6H).The synthesis of compound P-2
Synthetic method only changes carbazole therein into 3- phenyl carbazoles with reference to the synthetic method of P-1.To obtained chemical combination Object P-2 carries out Mass Spectrometer Method, product m/e：959.
The synthesis of compound P-9
Synthetic method only changes carbazole therein into 4H- benzos [def] carbazole with reference to the synthetic method of P-1.To obtaining Compound P-9, carry out Mass Spectrometer Method, product m/e：803.
The synthesis of compound P-10
Synthetic method only changes carbazole therein into 1,7- diphenyl 4H- benzos [def] with reference to the synthetic method of P-1 Carbazole.To obtained compound P-10, Mass Spectrometer Method, product m/e are carried out：1260.
The synthesis of compound P-11
Synthetic method only changes carbazole therein into 2,6- diphenyl 4H- benzos [def] with reference to the synthetic method of P-1 Carbazole.To obtained compound P-11, Mass Spectrometer Method, product m/e are carried out：1260.
The synthesis of compound P-12
Synthetic method only changes carbazole therein into 1,7- bis- (2- naphthalenes) -4H- benzos with reference to the synthetic method of P-1 [def] carbazole.To obtained compound P-12, Mass Spectrometer Method, product m/e are carried out：1560.The synthesis of compound P-3
It is as follows to synthesize equation：
In 1000 milliliters of there-necked flasks, 300 milliliters of toluene of addition, 200 milliliters of ethyl alcohol, 100 milliliters of water, 5.42 grams Compound shown in (0.01mol) formula M-08,9.5 grams of (0.033mol) 4- (N- carbazyls) phenyl boric acids, 4.14 grams of (0.03mol) carbon 1.15 grams of (0.001mol) tetra-triphenylphosphine palladiums are added under nitrogen protection for sour potassium, are to slowly warm up to 70 DEG C and react 24 hours, drop Neutrality is washed with water in temperature, liquid separation, organic layer, after being dried with anhydrous magnesium sulfate, with silica gel post separation, uses petroleum ether：Acetic acid second Ester (volume ratio 7：3) it is eluted as eluant, eluent, obtains 2.9 grams of product shown in formula P-3, yield 60.4%.
To obtained compound P-3, Mass Spectrometer Method, product m/e are carried out：959.
Nuclear-magnetism detection is carried out to product shown in obtained formula P-3, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 8.55 (m, 3H), δ 8.19 (m, 3H), δ 7.91 (m, 12H), δ 7.73 (s, 1H), δ 7.52 (m, 5H), δ 7.42 (m, 5H), δ 7.23~7.08 (m, 13H), δ 2.43 (d, 1H), δ 1.94 (d, 1H), δ 1.72 (s, 3H), δ 0.91 (s, 6H).The synthesis of compound P-4
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 3- (N- carbazoles with reference to the synthetic method of P-3 Base) phenyl boric acid.To obtained compound P-4, Mass Spectrometer Method, product m/e are carried out：959.The synthesis of compound P-5
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into N- ethyl clicks with reference to the synthetic method of P-3 Azoles -3- boric acid.To obtained compound P-5, Mass Spectrometer Method, product m/e are carried out：815.The synthesis of compound P-6
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into N- phenyl clicks with reference to the synthetic method of P-3 Azoles -3- boric acid.To obtained compound P-6, Mass Spectrometer Method, product m/e are carried out：959.The synthesis of compound P-7
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 3,5- bis- (N- with reference to the synthetic method of P-3 Carbazyl) phenyl boric acid.To obtained compound P-7, Mass Spectrometer Method, product m/e are carried out：1456.
The synthesis of compound P-8
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 3- (N- carbazoles with reference to the synthetic method of P-3 Base) -5- (N- (3- phenyl)-carbazyl)) phenyl boric acid.To obtained compound P-8, Mass Spectrometer Method, product m/e are carried out：1684.
The synthesis of compound P-13
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 7- (N- carbazoles with reference to the synthetic method of P-3 Base) -9,9- dimethyl fluorene -2- boric acid.To obtained compound P-13, Mass Spectrometer Method, product m/e are carried out：1309.
The synthesis of compound P-14
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 7- (N- carbazoles with reference to the synthetic method of P-3 Base) -9,9- diphenylfluorene -2- boric acid.To obtained compound P-14, Mass Spectrometer Method, product m/e are carried out：1681.
The synthesis of compound P-15
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 2'- (9H- clicks with reference to the synthetic method of P-3 Azoles -9- bases) two fluorenes -2- boric acid of -9,9'- spiral shells.To obtained compound P-15, Mass Spectrometer Method, product m/e are carried out：1675.
The synthesis of compound P-16
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 7- (diphenyl with reference to the synthetic method of P-3 Amido) -9,9- dimethyl fluorene -2- boric acid.To obtained compound P-16, Mass Spectrometer Method, product m/e are carried out：1315.
The synthesis of compound P-17
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 6- (4- (two with reference to the synthetic method of P-3 Phenyl amino) phenyl) -9- phenyl carbazole -3- boric acid.To obtained compound P-17, Mass Spectrometer Method, product m/e are carried out： 1690。
The synthesis of compound P-18
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 6- (4- (9- with reference to the synthetic method of P-3 Carbazyl) phenyl) -9- phenyl carbazole -3- boric acid.To obtained compound P-18, Mass Spectrometer Method, product m/e are carried out：1684.
The synthesis of compound P-19
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 6- (4- (two with reference to the synthetic method of P-3 ([1,1'- biphenyl] -4- bases) amido) phenyl) -9- phenyl-carbazole -3- boric acid.To obtained compound P-19, mass spectrum inspection is carried out It surveys, product m/e：2146.
The synthesis of compound P-20
Synthetic method with reference to P-3 synthetic method, only by 4- therein (N- carbazyls) phenyl boric acid change into 6- (4- ([1, 1'- biphenyl] -4- bases (9,9- dimethyl fluorene -2- bases) amido) phenyl) -9- phenyl carbazole -3- boric acid.To obtained compound P- 20, carry out Mass Spectrometer Method, product m/e：2266.
The synthesis of compound P-21
Synthetic method only changes 4- therein (N- carbazyls) phenyl boric acid into 6- (4- (two with reference to the synthetic method of P-3 (9,9- dimethyl fluorene -2- bases) amido) phenyl) -9- phenyl-carbazole -3- boric acid.To obtained compound P-21, mass spectrum is carried out Detection, product m/e：2386.
The synthesis of compound P-22
Synthetic method with reference to P-3 synthetic method, only by 4- therein (N- carbazyls) phenyl boric acid change into 6- (4- ([1, 1'- biphenyl] -3- bases (9,9- dimethyl fluorene -2- bases) amido) phenyl) -9- phenyl carbazole -3- boric acid.To obtained compound P- 22, carry out Mass Spectrometer Method, product m/e：2266.
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 or the material of hole transmission layer 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 selects CBP, PH-1, PH-2 respectively.
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
Feux rouges material of main part It is required that brightness cd/m2 Driving voltage V Current efficiency cd/A
CBP 1000 4.78 11.2
PH-1 1000 4.62 12.11
PH-2 1000 4.58 12.62
Compound P-1 1000 4.43 13.46
Compound P-2 1000 4.1 12.98
Compound P-4 1000 4.23 13.21
Compound P-6 1000 4.17 13.21
Compound P-7 1000 4.33 13.25
Compound P-10 1000 4.34 13.04
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, PH-1, PH-2 obtain preferable effect as the organic electroluminescence device of main body, obtain higher current efficiency With lower driving 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, PH-1, PH-2 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, PH-1, PH-2 obtain preferable effect as the organic electroluminescence device of main body, obtain higher current efficiency With lower driving 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, PH, PH-2 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
Blue-light emitting host material It is required that brightness cd/m2 Driving voltage V Current efficiency cd/A
CBP 200 6.88 11.26
PH-1 200 6.55 12.35
PH-2 200 6.43 12.06
Compound P-1 200 6.39 13.51
Compound P-2 200 6.37 12.64
Compound P-4 200 6.33 14.51
Compound P-6 200 6.43 12.9
Compound P-7 200 5.95 12.88
Compound P-10 200 6.41 13.94
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, PH-1, PH-2 obtain preferable effect as the organic electroluminescence device of main body, obtain higher current efficiency With lower driving voltage.
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, HT-1, HT-2 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
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.
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. a kind of phenyl indene compounds, which is characterized in that shown in the compound such as formula (I)：
Selected from substituted or unsubstituted carbazyl, substituted or unsubstituted benzo carbazole base in described A1, A2, A3.
2. phenyl indene compounds according to claim 1, which is characterized in that the compound is selected from：
3. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device contains claim 1-2 The phenyl indene compounds.
4. organic electroluminescence device according to claim 3, which is characterized in that the organic electroluminescence device has The material of main part of machine luminescent layer or the material of hole transmission layer are any phenyl indene compounds of claim 1-2.
5. organic electroluminescence device according to claim 4, 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.
6. a kind of display device, which is characterized in that include the organic electroluminescence device as described in claim 3~6 is any.
7. a kind of electronic equipment, including display device described in claim 6.
8. electronic equipment according to claim 7, the electronic equipment is selected from mobile phone, computer, tablet computer, wrist-watch, VR Display, digital camera, bracelet, counter, electronic watch.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007046651A1 (en) * 2005-10-21 2007-04-26 Lg Chem. Ltd. Indene derivatives and organic light emitting diode using the same
US20090098397A1 (en) * 2007-10-15 2009-04-16 Myeong-Suk Kim Indene derivative compound and organic light emitting device comprising the same
CN104629721A (en) * 2013-11-09 2015-05-20 吉林奥来德光电材料股份有限公司 Organic luminescent material with excellent performance and preparation method thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007046651A1 (en) * 2005-10-21 2007-04-26 Lg Chem. Ltd. Indene derivatives and organic light emitting diode using the same
US20090098397A1 (en) * 2007-10-15 2009-04-16 Myeong-Suk Kim Indene derivative compound and organic light emitting device comprising the same
CN104629721A (en) * 2013-11-09 2015-05-20 吉林奥来德光电材料股份有限公司 Organic luminescent material with excellent performance and preparation method thereof

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孟令芝等: "《有机波谱分析》", 31 July 2016, 武汉：武汉大学出版社 *

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