CN109320495A - A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure - Google Patents

A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure Download PDF

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CN109320495A
CN109320495A CN201811437583.9A CN201811437583A CN109320495A CN 109320495 A CN109320495 A CN 109320495A CN 201811437583 A CN201811437583 A CN 201811437583A CN 109320495 A CN109320495 A CN 109320495A
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layer
double
amine compounds
organic
spiro structure
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黄锦海
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Shanghai Taoe Chemical Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The present invention provides a kind of double triaromatic amine compounds containing spiro structure, have the following structure formula:The compound has preferable thermal stability, high-luminous-efficiency, high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, exciton barrier-layer, electron transfer layer, the at least one layer compound containing such as structural formula I in organic layer has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long using the organic electroluminescence device that the compound makes.

Description

A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of double triaromatic amine compounds containing spiro structure And its application, further relate to a kind of organic electroluminescence device.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, so that Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency Luminescent material.
In organic electroluminescence device, the introducing of hole mobile material and injection material can be effectively reduced positive electricity Lotus is transferred to the ability of luminescent layer from anode, improves the efficiency and thermostabilization of device.Traditional hole-injecting material, such as copper Phthalocyanine (CuPc), degradation is slow, and preparation energy consumption is high, is unfavorable for environmental protection, and it can absorb light, influence device Efficiency.NPB etc. original hole mobile material, thermal stability is poor, also largely influences device lifetime.Thus, it needs Develop the electroluminescent organic material of efficient stable.
Summary of the invention
The present invention provides a kind of double triaromatic amine compounds containing spiro structure, are the chemical combination for having the following structure Formulas I Object:
Wherein, R1-R8Independently selected from hydrogen, deuterium, halogen, cyano, the alkyl of C1-C12, substitution or unsubstituted C6- The heteroaryl of the aryl of C30, substitution or unsubstituted C3-C30；
X1、X2Independently selected from O, S, N；
L1、L2Aryl independently selected from singly-bound, the alkyl of C1-C12, substitution or unsubstituted C6-C30, replace or The heteroaryl of unsubstituted C3-C30；
Ar1-Ar4Independently selected from hydrogen, the aryl of substitution or unsubstituted C6-C30, substitution or unsubstituted C3- The heteroaryl of C30, Ar1With Ar2、Ar1With Ar2It is not cyclic, or be formed by connecting ring by singly-bound or following group: singly-bound, substitution Or methylene, oxygen atom, the sulphur atom of unsubstituted C1-C12.
Preferably, Ar1-Ar4Independently selected from phenyl, diphenyl phenyl, naphthalene, naphthylphenyl, xenyl, terphenyl, Three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, fluorenyl, carbazyl, dibenzothiophene and two Benzofuranyl.It is further preferred that Ar1-Ar4Independently selected from by above-mentioned group by the alkyl of C1-C12 replace gained group.
Preferably, double triaromatic amine compounds containing spiro structure are the compound of following structural 1-46:
Double triaromatic amine compounds containing spiro structure of the invention can be reacted by Buchwald-Hartwig and Wu Er Graceful anti-, suzkui should be prepared.
Double triaromatic amine compounds containing spiro structure of the invention can be applied to organic electroluminescence device, solar-electricity Pond, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, exciton barrier-layer, electron transfer layer Layer, at least one layer of double triaromatic amine compounds containing spiro structure containing as described in structural formula I in the organic layer.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, the layer where double triaromatic amine compounds containing spiro structure is hole transmission layer.
Double triaromatic amine compounds containing spiro structure as described in structural formula I are used alone, or mix with other compounds It uses；Double triaromatic amine compounds containing spiro structure as described in structural formula I can be used alone one such compound, It can be simultaneously using two or more the compound in structural formula I；A kind of containing selected from structural formula 1-46 is used alone Double triaromatic amine compounds of spiro structure, or double three fragrance containing spiro structure using two or more selected from structural formula 1-46 simultaneously Amine compounds.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 46-460nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance can effectively be transferred to hole on luminescent layer from anode.In addition to can be used with the compound of the present invention It outside, can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano six (hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs The range of visible light.Except it is of the invention there is Compounds of structural formula I in addition to, following compound can also be contained, but not limited to this, Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.It can choose following compound, but It is not limited to this: oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination Object, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex can choose following compound, but not limited to this: alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made It is prepared with vapour deposition method or sputtering method.
Device experimental shows double triaromatic amine compounds containing spiro structure of the present invention as described in structural formula I, has preferable Thermal stability, high-luminous-efficiency, high luminance purity.Organic electroluminescence device using compound production has electroluminescent The advantage that efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention；
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 146 be hair Photosphere, 160 be electron transfer layer, and 170 be electron injecting layer, and 180 be cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
Intermediate A, the synthetic route of B, C
The synthesis of intermediate A
In three-necked flask, thienyl boric acid (10g, 78mmol), adjacent bromo-iodobenzene (24g, 86mmol), potassium carbonate are sequentially added (27g, 0.2mol), tetrahydrofuran (200mL), water (100mL), tetra-triphenylphosphine palladium (0.5g), under nitrogen protection, are heated back Stream 10 hours, it is cooling, it is extracted with dichloromethane, is concentrated, crude product obtains 14g, yield 75% through column chromatographic purifying.
The synthesis of intermediate B
In three-necked flask, intermediate A (10g, 42mmol), dry tetrahydrofuran (100mL) are sequentially added, is protected in nitrogen It is cooled to subzero 70 DEG C under shield, is slowly added to the n-BuLi (16.8mL) of 2.5M, drips reaction 1 hour, is then added Tetrahydrofuran solution of the 60mL dissolved with 2- bromine Fluorenone (10.8g, 42mmol).It adds, is slowly increased to room temperature, react 2 hours, be added Methylene chloride extraction, concentration, are added acetic acid (100mL) and concentrated hydrochloric acid (3mL), are heated to reflux 5 hours, cooling, remove solvent, slightly Product dichloromethane solvent, washing, the dry concentration of organic layer, crude product obtain 9.1g, yield 59% through column chromatographic purifying.
The synthesis of intermediate C
It in three-necked flask, is added intermediate B (8g, 24.4mmol), n,N-Dimethylformamide (50mL) is slowly added to Bromo-succinimide (3.6g, 20mmol) reacts at room temperature 12 hours, and water is added, is extracted with dichloromethane, dry, concentration, slightly Product obtains 7.9g, yield 83% through column chromatographic purifying.
The synthetic route of intermediate D, E, F
The synthesis of intermediate D
Synthetic method replaces thienyl boric acid, yield 57% as with intermediate A, with furan boronic acid.
Intermediate E synthetic method
Synthetic method replaces intermediate A, yield 49% as with intermediate B, with intermediate D.
The synthesis of intermediate F
Synthetic method replaces intermediate B, yield 82% as with intermediate C, with intermediate E.
Embodiment 2
The synthetic route of compound 2
The synthetic method of compound 2
In flask, intermediate C (2g, 4.1mmol), two (4- tert-butyl-benzene) amine (2.9g, 9.2mmol), tertiary fourth is added Sodium alkoxide (2g, 20mmol), palladium acetate (50mg), X-phos (100mg), ortho-xylene (30mL), are heated back under nitrogen protection Stream 24 hours, it is cooling, solvent is removed, crude product obtains 2.5g, yield 68% with column chromatographic purifying.
The synthetic method of other embodiments is all intermediate C and intermediate F as raw material such as compound 2, then with Other amine reactions, table 1 specific as follows:
Table 1
Embodiment 11-19
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share Department) successively pass through: deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, the PEDOT:PSS (Polyglycolic acid fibre-is poly- (styrene sulfonate)) of spin coating 45nm thickness is on ITO It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the compounds of this invention of 40nm thickness is deposited on hole injection layer as hole mobile material 140.
Then, the luminescent layer 146 of 30nm thickness is deposited on electronic barrier layer, wherein luminescent material based on CBP, and with The Ir (ppy) that weight ratio is 8%3Guest materials is adulterated as phosphorescence.
Then, the TMPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, vapor deposition 1nm LiF is electron injecting layer 170 and 80nm Al as device cathodes 180.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR646 spectrometer measure 100mA/cm2Current density under external quantum efficiency be such as table 2.
Comparative example 1
In addition to use NPB replace the compounds of this invention as hole mobile material other than, comparative example prepares the method and reality of device It is the same to apply a 10-19.
Table 2
The structural formula of compound described in device is as follows:
From Table 2, it can be seen that double triaromatic amine compounds of the invention containing spiro structure are used for organic electroluminescence Part can reduce operating voltage, improve device efficiency, be the hole mobile material with excellent performance.As described above, of the invention Compound there is high stability, the organic electroluminescence device of preparation has high efficiency and optical purity.
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical solution, all should be within the scope of protection determined by the claims.

Claims (10)

1. a kind of double triaromatic amine compounds containing spiro structure, which is characterized in that be the compound for having the following structure Formulas I:
Wherein, R1-R8Independently selected from hydrogen, deuterium, halogen, cyano, the alkyl of C1-C12, substitution or unsubstituted C6-C30 The heteroaryl of aryl, substitution or unsubstituted C3-C30；
X is selected from O, S, N；
L1、L2Aryl independently selected from singly-bound, the alkyl of C1-C12, substitution or unsubstituted C6-C30 replaces or does not take The heteroaryl of the C3-C30 in generation；
Ar1-Ar4Independently selected from hydrogen, the aryl of substitution or unsubstituted C6-C30, substitution or unsubstituted C3-C30 Heteroaryl, Ar1With Ar2、Ar1With Ar2It is not cyclic, be either formed by connecting ring by singly-bound or following group: singly-bound, substitution or Methylene, oxygen atom, the sulphur atom of unsubstituted C1-C12.
2. double triaromatic amine compounds containing spiro structure as described in claim 1, which is characterized in that Ar1-Ar4Independently selected from Phenyl, diphenyl phenyl, terphenyl, naphthalene, phenyl napthyl, naphthylphenyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, Base, fluoranthene base, acenaphthenyl, acenaphthylene base, fluorenyl, dibenzothiophene and dibenzofuran group.
3. double triaromatic amine compounds containing spiro structure as claimed in claim 2, which is characterized in that Ar1-Ar4Independently selected from Group described in claim 2 replaces gained group by the alkyl of C1-C12.
4. double triaromatic amine compounds containing spiro structure as described in claim 1, which is characterized in that be following structural 1-46 Compound:
5. the application of double triaromatic amine compounds in organic electroluminescence device described in claim 1 containing spiro structure.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole Implanted layer, hole transmission layer, hole blocking layer, exciton barrier-layer, at least one layer in electron transfer layer, which is characterized in that institute It states at least one layer of containing double triaromatic amine compounds containing spiro structure as described in claim 1 in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 containing spiro structure Layer where double triaromatic amine compounds is hole transmission layer.
8. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 containing spiro structure Double triaromatic amine compounds are used alone, or are used in mixed way with other compounds.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from such as claim Double triaromatic amine compounds containing spiro structure of structural formula 1-46 described in 4, or wanted simultaneously using two or more selected from such as right Double triaromatic amine compounds containing spiro structure of structural formula 1-46 described in asking 4.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that the overall thickness of the organic layer is 1- 1000nm。
CN201811437583.9A 2018-11-28 2018-11-28 A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure Pending CN109320495A (en)

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CN110240594A (en) * 2019-06-28 2019-09-17 上海天马有机发光显示技术有限公司 Compound, OLED device and electronic equipment
CN110467626A (en) * 2019-09-12 2019-11-19 北京燕化集联光电技术有限公司 A kind of New-type spiro structural compounds and its application in OLED device
CN112390789A (en) * 2019-08-16 2021-02-23 南京高光半导体材料有限公司 Electron transport material and organic electroluminescent device using same

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110240594A (en) * 2019-06-28 2019-09-17 上海天马有机发光显示技术有限公司 Compound, OLED device and electronic equipment
CN110240594B (en) * 2019-06-28 2021-12-21 武汉天马微电子有限公司 Compound, OLED device and electronic equipment
CN112390789A (en) * 2019-08-16 2021-02-23 南京高光半导体材料有限公司 Electron transport material and organic electroluminescent device using same
CN112390789B (en) * 2019-08-16 2022-05-13 南京高光半导体材料有限公司 Electron transport material and organic electroluminescent device using same
CN110467626A (en) * 2019-09-12 2019-11-19 北京燕化集联光电技术有限公司 A kind of New-type spiro structural compounds and its application in OLED device
CN110467626B (en) * 2019-09-12 2021-06-15 北京燕化集联光电技术有限公司 Novel spiro-structure compound and application thereof in OLED (organic light emitting diode) device

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Application publication date: 20190212