CN108530305A - A kind of new organic materials and its application in display device - Google Patents

A kind of new organic materials and its application in display device Download PDF

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CN108530305A
CN108530305A CN201810231419.6A CN201810231419A CN108530305A CN 108530305 A CN108530305 A CN 108530305A CN 201810231419 A CN201810231419 A CN 201810231419A CN 108530305 A CN108530305 A CN 108530305A
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layer
organic materials
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曹占广
班全志
程丹丹
杭德余
李继响
段陆萌
纪秦思
王敬丽
马天凯
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Beijing Yanshan Gicom Photoelectric Technology Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
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    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14Carrier transporting layers
    • H10K50/15Hole transporting layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

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  • Organic Chemistry (AREA)
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  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention relates to organic electroluminescent (OLED) display field, more particularly to a kind of new organic materials and its application in display device, the organic material general structure is as follows.Novel OLED material provided by the invention is centered on fused ring compound, using (1 naphthylamines is end group) containing fluorine atom, by in the active position of polycyclc aromatic compound, the substituent group (1 naphthylamines of N phenyl) with hole transport performance is introduced, a kind of novel OLED material with hole transport performance is obtained.Such material has high hole mobility, preferable thin film stability and suitable molecular entergy level, can be used in field of organic electroluminescence, be used as hole mobile material, be had broad application prospects.

Description

A kind of new organic materials and its application in display device
Technical field
The invention belongs to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical fields, and in particular to a kind of new organic materials, and its having Application in organic electroluminescence devices.
Background technology
Application of organic electroluminescent (OLED) material in the fields such as presentation of information material, organic optoelectronic material has Great researching value and fine application prospect.With the development of multimedia information technology, to flat-panel display device performance It is required that higher and higher.Current main display technology has plasma display apparatus, field emission display and organic electroluminescent Display device (OLED).Wherein, OLED has itself luminous, low-voltage direct-current driving, all solidstate, the wide, various colors in visual angle etc. Series of advantages, compared with liquid crystal display device, OLED does not need backlight, and visual angle is wider, low in energy consumption, and response speed is liquid 1000 times of crystal display device, therefore, OLED have broader practice foreground.
For the organic hole transport material reported at present since molecular weight is generally smaller, the glass transition temperature of material is relatively low, During materials'use, charging and discharging, material are easy crystallization repeatedly, and the homogeneity of film is destroyed, to influence materials'use Service life.Therefore, the organic hole transport material for developing stability and high efficiency improves device light emitting efficiency, prolongs to reduce driving voltage Long device lifetime has critically important actual application value.
Invention content
The purpose of the present invention is to provide can carry out low voltage drive, long lifespan and the OLED element of high efficiency, And the compound of such OLED element can be provided.
Specifically, present invention firstly provides a kind of novel organic material, there is the structure as shown in general formula I:
In general formula I, Ar is selected from:
Wherein, m is selected from 1 to 4 integer;
Indicate substitution position.
Preferably, in general formula I:
Ar is selected from:
M is 1 or 2.
As further preferred technical solution, the organic material is selected from one kind of following compound:
Above-mentioned organic material provided by the present invention on specific phenyl ring due to containing fluorine atom, so as to increase point Distance between son prevents the association between compound, reduces the probability of molecule piled up.It is less likely to occur to crystallize when vapor deposition Change, OLED yield rates can be effectively improved by being applied in OLED device, reduced driving voltage, improved luminous efficiency, increase the longevity Life.
Invention also provides the preparation methods of above-mentioned organic material, specifically, preparation side provided by the present invention The method reaction mechanism mechanism of reaction is as follows:
Include the following steps:
(a) using compound I-1 as starting material, withCoupling reaction occurs, obtains compound I-2;
(b) with dibromo condensed-nuclei aromatics coupling reaction occurs for compound I-2, obtains compound I.
Wherein, Ar and m refers specifically to generation ibid restriction about organic material.
Known common approach can be used to realize in above-mentioned step those skilled in the art, such as selects suitable catalysis Agent, solvent determine suitable reaction temperature, time etc., and the present invention is not particularly limited this.
Preferably, above-mentioned preparation method includes the following steps:
(a) using compound I-1 as starting material, using toluene as solvent, with three (hexichol benzylacetone) two palladiums and three tertiary fourths Base phosphine is catalyst, and sodium tert-butoxide is alkali, nitrogen protection, 100-110 DEG C of temperature control, compound I-1 withCoupling reaction occurs, Obtain compound I-2;
(b) using dimethylbenzene as solvent, using three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine as catalyst, sodium tert-butoxide For alkali, nitrogen protection, 110-120 DEG C of temperature control, compound I-2 and dibromo condensed-nuclei aromatics generation coupling reaction, compound I is obtained;
Wherein, Ar and m refers specifically to generation ibid restriction about organic material.
Above-mentioned dibromo condensed-nuclei aromatics, sodium tert-butoxide and three (hexichol benzylacetone) two palladiums etc. can pass through open business way Method known per se synthesizes to obtain in diameter or document.
Invention further provides application of the above-mentioned organic material in organic electroluminescence device.
Preferably, organic material of the present invention is used as hole transmission layer in organic electroluminescence device.
The present invention also provides a kind of organic electroluminescence device, organic function layer includes above-mentioned general formula compound, Such compound is used as the hole mobile material in organic function layer.
Preferably, above-mentioned organic electroluminescence device is from the bottom to top successively by transparent substrate, anode layer, the hole transport Layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode layer composition.
Further preferably:
The material for constituting the transparent substrate is glass substrate or flexible substrate;
Substrate can use the substrate in conventional organic luminescence device, such as:Glass or plastics.
The material for constituting the anode layer is inorganic material;Wherein, the inorganic material be specially tin indium oxide (ITO), At least one of zinc oxide, zinc tin oxide, gold, silver or copper, preferably tin indium oxide (ITO);
Glass substrate, ITO is preferably selected to make anode material in the element manufacturing of the present invention.
The material for constituting the hole transmission layer is Formulas I compound represented;
The material for constituting the organic luminous layer is made of material of main part;
Wherein, the material of main part is any one in following compound:
Constitute any one of the material of the electron transfer layer in following compound:
The material for constituting the electron injecting layer is selected from LiF, Li2O, MgO, Al2O3In one kind, preferably LiF.
Constitute the one kind of the material of the cathode in lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, gold and silver, preferably aluminium.
Specifically,
The thickness of the hole transmission layer is 5-15nm, preferably 8nm;
The thickness of the organic luminous layer is 10-100nm, preferably 30nm;
The thickness of the electron transfer layer is 10-30nm, preferably 40nm;
The thickness of the electron injecting layer is 5-30nm, preferably 10nm;
The thickness of the cathode is 50-110nm, preferably 60nm.
Novel OLED material provided by the invention centered on fused ring compound, with containing fluorine atom (naphthalidine be end Base), by the active position of polycyclc aromatic compound, introducing the substituent group (N- phenyl -1- naphthalenes with hole transport performance Amine), obtain a kind of novel OLED material with hole transport performance.Such material has high hole mobility, preferably Thin film stability and suitable molecular entergy level, field of organic electroluminescence can be used in, made as hole mobile material With.
Specific implementation mode
Tri-tert-butylphosphine used in the present invention, sodium tert-butoxide, three (hexichol benzylacetone) two palladiums, dibromo polycyclic aromatic hydrocarbon etc. Industrial chemicals can conveniently be bought in chemical products market at home.
Compound synthesis in the present invention all can refer to the progress of 1 method of embodiment.It is described below in the present invention and partly leads Want the synthetic method of compound.
Embodiment 1
The synthesis of (compound 1)
Synthetic route is as follows:
Compound 1
1) synthesis of compound 1-2
1000 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 46.1g (0.48mol), benzene are sequentially added after argon gas displacement Amine 27.9g (purity 99%, 0.3mol), the bromo- 2- fluoronaphthalenes of 45g1- (purity 99%, 0.2mol) and toluene 400ml.Argon gas again 3ml tri-tert-butylphosphines and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after displacement.After adding, agitating and heating heating is opened To 100 DEG C, 100-110 DEG C of temperature control reacts 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C, filtrate is rotated, uses dichloro After methane dissolving, being washed twice with 4mol/L hydrochloric acid solutions, liquid separation is dried with anhydrous sodium sulfate, is filtered, and filtrate is rotated, Obtain 43g yellow products, purity 99%, yield 91%.
2) synthesis of compound 1
500 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 18.1g (0.188mol), 9 are sequentially added after argon gas displacement, 10- dibromoanthracenes 26.4g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.Again 1.6ml tri- is sequentially added after argon gas displacement Tertiary butyl phosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start be added dropwise by The solution of the fluoro- naphthalidines of 48.1gN- phenyl -2- (purity 99%, 0.203mol) and 100ml dimethylbenzene composition, temperature control 110-120 ℃.50 DEG C are cooled to, the hydrolysis of 100m deionized waters is added, stirs 10 minutes, filtering, filter cake is boiled several times with DMF, obtained repeatedly 38g yellow products, purity 99%, yield 75%.
Product MS (m/e):648.24;Elemental analysis (C46H30F2N2):Theoretical value C:85.16%, H:4.66%, F: 5.86%, N:4.32%;Measured value C:85.15%, H:4.66%, F:5.86%, N:4.33%.
Embodiment 2
The synthesis of (compound 2)
Synthetic route is as follows:
Compound 2
1) synthesis of compound 2-1
1000 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 46.1g (0.48mol), benzene are sequentially added after argon gas displacement Amine 27.9g (purity 99%, 0.3mol), the bromo- 2- fluoronaphthalenes of 45g1- (purity 99%, 0.2mol) and toluene 400ml.Argon gas again 3ml tri-tert-butylphosphines and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after displacement.After adding, agitating and heating heating is opened To 100 DEG C, 100-110 DEG C of temperature control reacts 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C, filtrate is rotated, uses dichloro After methane dissolving, being washed twice with 4mol/L hydrochloric acid solutions, liquid separation is dried with anhydrous sodium sulfate, is filtered, and filtrate is rotated, Obtain 42.7g yellow products, purity 99%, yield 90%.
2) synthesis of compound 2
500 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 18.1g (0.188mol), 9 are sequentially added after argon gas displacement, Bis- bromo- 2- methyl anthracene 27.5g (purity 99%, 0.0785mol) of 10- and dimethylbenzene 100ml.It is sequentially added after argon gas displacement again 1.6ml tri-tert-butylphosphines and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise The solution being made of the fluoro- naphthalidines of 48.1gN- phenyl -2- (purity 99%, 0.203mol) and 100ml dimethylbenzene, temperature control 110- 120℃.50 DEG C are cooled to, the hydrolysis of 100m deionized waters is added, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF, Obtain 36.3g yellow products, purity 99%, yield 70%.
Product MS (m/e):661.76;Elemental analysis (C47H32F2N2):Theoretical value C:85.17%, H:4.87%, F: 5.73%, N:4.23%;Measured value C:85.16%, H:4.88%, F:5.72%, N:4.24%.
Embodiment 3
The synthesis of (compound 3)
Synthetic route is as follows:
Compound 3
1) synthesis of compound 3-1
1000 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 46.1g (0.48mol), benzene are sequentially added after argon gas displacement Amine 27.9g (purity 99%, 0.3mol), the bromo- 2- fluoronaphthalenes of 45g1- (purity 99%, 0.2mol) and toluene 400ml.Argon gas again 3ml tri-tert-butylphosphines and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after displacement.After adding, agitating and heating heating is opened To 100 DEG C, 100-110 DEG C of temperature control reacts 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C, filtrate is rotated, uses dichloro After methane dissolving, being washed twice with 4mol/L hydrochloric acid solutions, liquid separation is dried with anhydrous sodium sulfate, is filtered, and filtrate is rotated, Obtain 45g yellow products, purity 99%, yield 95%.
2) synthesis of compound 3
500 milliliters of there-necked flasks match magnetic agitation, sodium tert-butoxide 18.1g (0.188mol), 6 are sequentially added after argon gas displacement, 12- dibromos bend 24g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.Again tri- uncles of 1.6ml are sequentially added after argon gas displacement Butyl phosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise by 48.1gN- The solution of the fluoro- naphthalidines of phenyl -2- (purity 99%, 0.203mol) and 100ml dimethylbenzene composition, 110-120 DEG C of temperature control.Cooling To 50 DEG C, the hydrolysis of 100m deionized waters is added, stirs 10 minutes, filtering, filter cake is boiled several times repeatedly with DMF, obtains 44g yellow Product, purity 99%, yield 80%.
Product MS (m/e):698.25;Elemental analysis (C50H32F2N2):Theoretical value C:85.94%, H:4.62%, F: 5.44%, N:4.0%;Measured value C:85.93%, H:4.61%, F:5.45%, N:4.01%.
According to embodiment 1, the technical solution of embodiment 2 and embodiment 3, it is only necessary to which the corresponding raw material of simple replacement does not change Become any substantive operations, following compound can be synthesized.
Embodiment 4 prepares device OLED-1~OLED-4
The method for preparing device OLED-1~OLED-4 is present embodiments provided, is included the following steps:
1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water It washes, it is 30 minutes ultrasonic in acetone/ethanol in the mixed solvent, it is baked to is completely dried under a clean environment, use ultraviolet rays cleaning Machine irradiates 10 minutes, and low energy cation beam bombarded surface is used in combination.
2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa, It is hole transmission layer that one layer of embodiment 1 is deposited on above-mentioned anode tunic and prepares the compound 1 of gained ownership Formulas I, and evaporation rate is 0.2nm/s, vapor deposition film thickness are 8nm;
3) continue to be deposited ADN on the hole transport layer as material of main part, as the organic luminous layer of device, evaporation rate Film thickness for 0.2nm/s, vapor deposition gained organic luminous layer is 30nm;
4) continue that electron transfer layers of the one layer of compound BCP as device is deposited on organic luminous layer, evaporation rate is 0.2nm/s, vapor deposition film thickness are 40nm;
5) continue that electron injecting layers of the one layer of LiF as device is deposited on electron transfer layer, evaporation rate is 0.2nm/s, vapor deposition film thickness are 10nm;
6) continue that cathodes of the one layer of Al as device, evaporation rate 0.2nm/s, vapor deposition is deposited on electron injecting layer Film thickness is 60nm;OLED device provided by the invention is obtained, OLED-1 is denoted as;
According to upper identical step, by the compound 1 in step 2) replace with embodiment 2 prepare gained compound 2, obtain To OLED-2 provided by the invention;
According to upper identical step, by the compound 1 in step 2) replace with embodiment 3 prepare gained compound 3, obtain To OLED-3 provided by the invention;
According to upper identical step, the compound 1 in step 2) is replaced with into NPB, obtains comparative device OLED-4;
The performance test results of obtained device OLED-1 to OLED-4 are as shown in table 1.
The performance test results of table 1, OLED-1 to OLED-4
From the foregoing, it will be observed that the device OLED-1 being prepared into using organic material shown in Formulas I provided by the invention is to OLED-4's Bright voltage is lower, brightness under the same conditions, the apparent device OLED-4 than NPB as hole mobile material of current efficiency It is much higher, and the service life of device be obviously prolonged very much.
Although the present invention is described in conjunction with the embodiments, the invention is not limited in above-described embodiments, should manage Solution, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise The scope of the present invention.

Claims (10)

1. a kind of new organic materials, it is characterised in that:Its structure is as shown in general formula I:
Wherein, Ar is selected from:
Wherein, m is selected from 1 to 4 integer;
Indicate substitution position.
2. new organic materials according to claim 1, it is characterised in that:In general formula I:Ar is selected from:
And/or m is 1 or 2.
3. new organic materials according to claim 1 or 2, it is characterised in that:The new organic materials are selected from as follows One kind of compound:
4. the preparation method of claim 1-3 any one of them new organic materials, it is characterised in that:The reaction mechanism mechanism of reaction is as follows:
Specifically comprise the following steps:
(a) using compound I-1 as starting material, withCoupling reaction occurs, obtains compound I-2;
(b) with dibromo condensed-nuclei aromatics coupling reaction occurs for compound I-2, obtains compound I;
Wherein, the reference of Ar and m is the same as described in claim any one of 1-3.
5. the preparation method of new organic materials according to claim 4, it is characterised in that:Include the following steps:
(a) using compound 1-1 as starting material, using toluene as solvent, with three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine For catalyst, sodium tert-butoxide is alkali, nitrogen protection, 100-110 DEG C of temperature control, compound 1-1 withCoupling reaction occurs, obtains Compound I-2;
(b) using dimethylbenzene as solvent, using three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine as catalyst, sodium tert-butoxide is Alkali, nitrogen protection, 110-120 DEG C of temperature control, compound 1-2 occur coupling reaction with dibromo condensed-nuclei aromatics, obtain compound I.
6. application of the claim 1-3 any one of them new organic materials in organic electroluminescence device.
7. application according to claim 6, it is characterised in that:The new organic materials are in the organic electroluminescence It is used as hole transmission layer in part.
8. a kind of organic electroluminescence device, it is characterised in that:Including by any one of the claim 1-3 new organic materials Manufactured hole transmission layer.
9. organic electroluminescence device according to claim 8, it is characterised in that:The organic electroluminescence device is under It is supreme successively by transparent substrate, anode layer, the hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and the moon Pole layer composition;
It is preferred that:
The material of the transparent substrate is glass substrate or plastics;
And/or;The material of the anode layer is constituted in tin indium oxide, zinc oxide, zinc tin oxide, gold, silver or copper at least It is a kind of;
And/or;The material of main part for constituting the organic luminous layer is any one in following compound:
And/or constitute any one of the material of the electron transfer layer in following compound:
And/or;The material for constituting the electron injecting layer is selected from LiF, Li2O, MgO or Al2O3In one kind;
And/or;Constitute the one kind of the material of the cathode in lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, gold and silver.
10. organic electroluminescence device according to claim 9, it is characterised in that:The thickness of the hole transmission layer is 5-15nm;The thickness of the organic luminous layer is 10-100nm;The thickness of the electron transfer layer is 10-30nm;The electronics The thickness of implanted layer is 5-30nm;The thickness of the cathode is 50-110nm.
CN201810231419.6A 2018-03-20 2018-03-20 A kind of new organic materials and its application in display device Pending CN108530305A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109574911A (en) * 2018-11-27 2019-04-05 北京燕化集联光电技术有限公司 A kind of luminous organic material and preparation method thereof and its application in the devices
CN109721526A (en) * 2018-11-27 2019-05-07 北京燕化集联光电技术有限公司 A kind of organic compound and preparation method thereof and its application in the devices

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102782084A (en) * 2010-03-06 2012-11-14 默克专利有限公司 Organic electroluminescent device
WO2017061779A1 (en) * 2015-10-06 2017-04-13 주식회사 엘지화학 Amine compound and organic light-emitting device comprising same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102782084A (en) * 2010-03-06 2012-11-14 默克专利有限公司 Organic electroluminescent device
WO2017061779A1 (en) * 2015-10-06 2017-04-13 주식회사 엘지화학 Amine compound and organic light-emitting device comprising same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109574911A (en) * 2018-11-27 2019-04-05 北京燕化集联光电技术有限公司 A kind of luminous organic material and preparation method thereof and its application in the devices
CN109721526A (en) * 2018-11-27 2019-05-07 北京燕化集联光电技术有限公司 A kind of organic compound and preparation method thereof and its application in the devices

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Application publication date: 20180914