CN104037361B - A kind of organic electroluminescence device - Google Patents
A kind of organic electroluminescence device Download PDFInfo
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- CN104037361B CN104037361B CN201410293402.5A CN201410293402A CN104037361B CN 104037361 B CN104037361 B CN 104037361B CN 201410293402 A CN201410293402 A CN 201410293402A CN 104037361 B CN104037361 B CN 104037361B
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- H—ELECTRICITY
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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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H—ELECTRICITY
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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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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Abstract
The invention provides a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterised in that in organic layer, at least one of which includes the compound of following structural formula (I).
Description
Technical field
The present invention relates to technical field of organic electroluminescence, more particularly to a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) is deposit, by spin coating or vacuum evaporation, the device that one layer of organic material is prepared between two metal electrodes, one classical three layers organic electroluminescence device comprises hole transmission layer, luminescent layer and electron transfer layer. The hole produced by anode is followed the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer through hole transmission layer and is formed exciton, then luminous. Organic electroluminescence device can regulate, as desired by the material changing luminescent layer, the light launching various needs.
Organic electroluminescence device is as a kind of novel Display Technique, have self-luminous, wide viewing angle, low energy consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, can make flexible and the particular advantages such as transparent display floater and environmental friendliness, can be applied in flat faced display and a new generation's illumination, it is also possible to as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially applied to some extent, and for example as the screen such as camera and mobile phone, but current OLED is low due to efficiency, the factors such as service life is short restrict its wider application, particularly large screen display. And restrict the performance that one of them key factor is exactly the electroluminescent organic material in organic electroluminescence device. Additionally, due to OLED when applying voltage-operated, Joule heat can be produced so that organic material is susceptible to crystallization, have impact on the life-span of device and efficiency, therefore, it is also desirable to the electroluminescent organic material of exploitation stability and high efficiency.
In organic electroluminescence device, the introducing of hole mobile material and injection material, it is possible to be effectively reduced positive charge and be transferred to the ability of luminescent layer from positive pole, improves the efficiency of device and thermally-stabilised. Traditional hole-injecting material, such as copperphthalocyanine (CuPc), degraded is slow, preparation power consumption height, is unfavorable for environmental conservation, and its can absorbing light, affect the efficiency of device. The hole mobile material that NPB etc. are original, heat stability is poor, also largely affects device lifetime. It is then desired to the organic electroluminescence transmission material of exploitation efficient stable.
Summary of the invention
Present invention firstly provides a kind of hole transport compound based on fluorenes, it is the compound being structured with formula (I):
Wherein, Ar1、Ar2、Ar3、Ar4And Ar5Separately selected from hydrogen, halogen, C1-C12 alkyl, C1-C8 alkoxyl, the replacing or unsubstituted aryl, the replacement of C3-C60 or unsubstituted heteroaryl of C6-C60;
L is selected from sky, singly-bound, C1-C12 alkyl, the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl.
Wherein preferred mode is:
Ar1Selected from C1-C8 alkyl, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
Ar2With Ar3 separately selected from phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
L is selected from sky, singly-bound, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
Ar4And Ar5Separately selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-are Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, triaromatic amine base, carbazyl;
Wherein said phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, triaromatic amine base, carbazyl can be replaced by the alkyl of C1-C4 further;
It is preferred that mode be:
Ar1Selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl, xenyl, tolyl;
Ar2And Ar3Separately selected from phenyl, naphthyl, xenyl;
L is selected from sky, singly-bound, phenyl, naphthyl;
Ar4And Ar5Separately selected from C1-C4 alkyl, substituted or unsubstituted following aryl and heteroaryl:
It is further preferred that a kind of hole transport compound based on fluorenes of the present invention, for the compound of following structural 1-50:
The hole transport compound based on fluorenes of the present invention can pass through Friedel-Crafts reaction, Suzuki coupling and Buchwald-Hartwig reaction and prepare.
The hole transport compound based on fluorenes of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer and electron transfer layer, has at least one layer containing, for example the hole transport compound based on fluorenes described in structural formula (I) in wherein said organic layer:
Wherein Ar1-Ar5, L defined as described above;
Or organic layer is luminescent layer and hole transmission layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer;
Wherein the layer based on the hole transport compound place of fluorenes as described in structural formula (I) is hole transmission layer or hole injection layer;
Wherein the hole transport compound based on fluorenes as described in structural formula (I) is above-claimed cpd 1-50.
The hole transport compound based on fluorenes as described in structural formula I can be used alone, it is also possible to uses with the mixing of other compounds; The hole transport compound based on fluorenes as described in structural formula I can be used alone a kind of compound therein, it is also possible to use two or more the compound in structural formula I simultaneously.
The organic electroluminescence device of the present invention, it is preferred that mode be, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, contains the compound of structural formula (I) in its hole-transporting layer; It is further preferred that the compound that compound is structural formula 1-50 in hole transmission layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, it is preferable that 50-500nm.
The organic electroluminescence device of the present invention is when the compound using the present invention to have structural formula I, other compound-materials of collocation can be used, such as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer etc., and obtain blue light, green glow, gold-tinted, HONGGUANG or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole transport performance, it is possible to effectively hole is transferred to luminescent layer from anode. Except above-mentioned there is structural formula (I) described compound except, other little molecule and macromolecular organic compounds can also be included, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the assorted triphen of six cyano group six (hexanitrilehexaazatriphenylene), 2,3,5,6-tetra-fluoro-7,7', 8,8'-tetra-cyanogen dimethyl-parabenzoquinone (F4-TCNQ), Polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, it is possible to regulate the scope of visible ray as required. can containing, for example lower compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, Benzo[b compounds, compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex, metal Phosphorescent complex is (such as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can be used alone, can also use by multiple mixture.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires have good electronic transmission performance, it is possible to effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility. Following compound can be selected, but be not limited to this, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, luxuriant and rich with fragrance quinoline compounds, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, it is mainly selected from alkali metal or alkali-metal compound, or it is selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but it is not limited to this, the organic complex of alkali metal, alkaline-earth metal, rare earth metal, the oxide of alkali gold brush or halogenide, the oxide of alkaline-earth metal or halogenide, the oxide of rare earth metal or halogenide, alkali metal or alkaline-earth metal;It is preferably lithium, lithium fluoride, lithium oxide, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, calcium fluoride, calcium oxide, magnesium, Afluon (Asta), magnesium carbonate, magnesium oxide, these compounds can be used alone can also mixture use, it is also possible to other electroluminescent organic materials with the use of.
Each layer of organic layer in the organic electroluminescence device of the present invention, it is possible to prepared by vacuum vapour deposition, molecular beam vapour deposition method, the modes such as the dip coating of solvent, spin-coating method, stick coating method or inkjet printing that are dissolved in. Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the hole transport compound based on fluorenes described in the present invention such as structural formula (I), has better heat stability, high-luminous-efficiency, high luminance purity. Electroluminescent efficiency is good and excitation is excellent and the advantage of life-span length to adopt this to have based on the organic electroluminescence device that the hole transport compound of fluorenes makes.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 2.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 22.
Fig. 3 is the hydrogen nuclear magnetic spectrogram of compound 28.
Fig. 4 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 5 is that embodiment 4 is at 20mA/cm2Electric current density under emission spectrum.
Detailed description of the invention
In order to describe the present invention in more detail, especially exemplified by example below, but it is not limited to this.
Embodiment 1
The synthesis of compound 2
The synthesis of compound 2-1
In reaction bulb, add Fluorenone (9g, 50mmol) and water (30ml), it is heated to 80 DEG C, in reaction bulb, is slowly added to bromine (8.8g, 55mmol), react 4 hours, add 100ml water and 100ml10% aqueous solution of sodium bisulfite. Filtering, the solid dehydrated alcohol recrystallization obtained obtains 11g product, and productivity is 85%.
The synthesis of compound 2-2
In reaction bulb, add compound 2-1 (2.58g, 10mmol) with 15ml oxolane, at 0 DEG C, dropping is dissolved in the phenyl-magnesium-bromide Grignard reagent (12mmol) of oxolane, adds and is slowly increased to room temperature reaction 12 hours, add dilute hydrochloric acid and regulate PH=7, it is extracted with ethyl acetate, dries with anhydrous magnesium sulfate, remove solvent, thick product silica gel column chromatography obtains white solid 2.3g solid, productivity 89%.1HNMR(400MHz,CDCl3) δ 7.67-7.69 (d, J=7.6Hz, 2H), 7.33-7.41 (m, 6H), 7.24-7.29 (m, 5H), 2.51 (s, 1H).
The synthesis of compound 2-3
In reaction bulb, add compound 2-2 (1.1g, 3.3mmol), triphenylamine (1.5g, 6.1mmol) and 15ml dichloromethane, stir the boron trifluoride ether solution dripping 5 under room temperature. Reacting 2 hours, the sudden no reaction of dropping ethanol, remove solvent, thick product silica gel column chromatography obtains white solid 1g white solid, productivity 56%.
1HNMR(400MHz,CDCl3) δ 7.71-7.73 (d, J=7.6Hz, 1H), 7.61-7.63 (d, J=8Hz, 1H) 7.47-7.53 (m, 2H), 7.20-7.40 (m, 12H), 6.90-7.08 (m, 10H).
The synthesis of compound 2
In reaction bulb, add compound 2-3 (200mg, 0.35mmol); N-phenyl-1-naphthylamine (150mg; 0.68mmol), potassium tert-butoxide (112mg, 1mmol); palladium (10mg); the toluene of 2-(dicyclohexyl phosphorus)-biphenyl (30mg) and 10ml adds under nitrogen protection to 80 DEG C of reactions 4 hours, cooling, removes solvent; thick product silica gel column chromatography obtains white solid 180mg solid, productivity 73%.
1HNMR (400MHz, DMSO) δ 7.95-7.97 (d, J=8Hz, 1H), 7.87-7.89 (d, J=8Hz, 1H), 7.73-7.77 (m, 3H), 7.15-7.55 (m, 16H), 6.75-7.07 (m, 17H). nuclear magnetic spectrogram is shown in Fig. 1
ESI, m/z:[M+H]+: 703.3.
Embodiment 2
The synthesis of compound 22
In reaction bulb; add compound 2-3 (0.5g; 0.89mmol); 4-boric acid triphenylamine (0.3g, 1mmol), oxolane (10ml); tetrakis triphenylphosphine palladium (50mg); wet chemical (2mol/l, 5mL), under nitrogen protection, heating reflux reaction is overnight. Stopped reaction, with dichloromethane extraction three times, merges organic facies, then is washed to neutrality; Separate organic facies, add anhydrous magnesium sulfate and dry, sucking filtration, it is spin-dried for; Silica gel column chromatography obtains white solid 340mg, productivity 52%.
1HNMR(400MHz,CDCl3) δ 7.76-7.80 (m, 2H), 7.56-7.60 (m, 2H), 7.35-7.45 (m, 4H), 7.19-7.29 (m, 14H), 6.89-7.13 (m, 18H) .ESI, m/z:[M+H]+: 729.4. nuclear magnetic spectrogram is shown in Fig. 2
Embodiment 3
The synthesis of compound 28
In reaction bulb; add compound 2-3 (0.2g; 0.35mmol); 4-(1-naphtyl phenyl amine base) phenylboric acid (0.15g, 0.44mmol), oxolane (10ml); tetrakis triphenylphosphine palladium (10mg); wet chemical (2mol/l, 5mL), under nitrogen protection, heating reflux reaction is overnight. Stopped reaction, with dichloromethane extraction three times, merges organic facies, then is washed to neutrality; Separate organic facies, add anhydrous magnesium sulfate and dry, sucking filtration, it is spin-dried for; Silica gel column chromatography obtains white solid 170mg, productivity 63%.1HNMR(400MHz,CDCl3) δ 7.88-7.95 (m, 2H), 7.74-7.90 (m, 3H), 7.34-7.57 (m, 11H), 7.19-7.28 (m, 11H), 6.88-7.09 (m, 15H) .ESI, m/z:[M+H]+: 779.4. nuclear magnetic spectrogram is shown in Fig. 3
Embodiment 4
The preparation of organic electroluminescence device
The compound using embodiment 1 prepares OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then by oxygen plasma treatment 30 seconds.
Then, it is deposited with compound 2, forms the thick hole transmission layer 130 of 60nm.
Then, hole transmission layer is deposited with the thick compound Alq of 30nm3As luminescent layer 140.
Then, luminescent layer is deposited with the thick compound Alq of 20nm3As electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device PhotoResearchPR650 spectrogrph records at 1.8mA/cm2Electric current density under efficiency be that 0.15cd/A, Fig. 5 represent that the organic electroluminescence device of the present embodiment is at 20mA/cm2Electric current density under emission spectrum, for green spectral.
Embodiment 5
The preparation of organic electroluminescence device
The compound using embodiment 2 prepares OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then by oxygen plasma treatment 30 seconds.
Then, it is deposited with compound 22, forms the thick hole transmission layer 130 of 60nm.
Then, hole transmission layer is deposited with the thick compound Alq of 30nm3As luminescent layer 140.
Then, luminescent layer is deposited with the thick compound Alq of 20nm3As electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.Prepared device PhotoResearchPR650 spectrogrph records at 1.8mA/cm2Electric current density under efficiency be 0.18cd/A
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then by oxygen plasma treatment 30 seconds.
Then, it is deposited with NPB, forms the thick hole transmission layer 130 of 60nm.
Then, hole transmission layer is deposited with the thick Alq of 30nm3As luminescent layer 140.
Then, luminescent layer is deposited with the thick Alq of 20nm3As electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device PhotoResearchPR650 spectrogrph records at 1.8mA/cm2Electric current density under efficiency be 0.044cd/A, launch green glow.
At identical conditions, the efficiency of organic electroluminescence device prepared by the organic electroluminescent compounds of the application present invention is higher than comparative example 1. As it has been described above, the compound of the present invention has high stability, organic electroluminescence device prepared by the present invention has high efficiency and optical purity.
Structural formula described in device
。
Claims (6)
1. an organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer comprises more than one layer in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterized in that described organic layer at least includes hole transmission layer, described hole transmission layer include the compound of following structural formula (I):
Wherein, Ar1Selected from phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
Ar2And Ar3Separately selected from phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
L is selected from singly-bound, phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl that replaced by C1-C4 alkyl;
Ar4And Ar5Separately selected from phenyl, the phenyl replaced by C1-C4 alkyl, naphthyl, the naphthyl replaced by C1-C4 alkyl,Replaced by C1-C4 alkylAnthryl, phenanthryl.
2. organic electroluminescence device according to claim 1, it is characterised in that wherein
Ar1Selected from phenyl, naphthyl, xenyl, tolyl;
Ar2And Ar3Separately selected from phenyl, naphthyl, xenyl;
L is selected from singly-bound, phenyl, naphthyl;
Ar4And Ar5Separately selected from substituted or unsubstituted following aryl:
3. a kind of organic electroluminescence device according to claim 1, it is characterised in that the compound that compound is following structural of structural formula (I):
4. organic electroluminescence device according to claim 1, it is characterised in that the compound as described in structural formula (I) is used alone or and other compounds mixing use.
5. organic electroluminescence device according to claim 1, it is characterised in that the compound as described in structural formula (I) is used alone a kind of compound therein or uses two or more the compound in structural formula (I) simultaneously.
6. organic electroluminescence device according to claim 1, it is characterised in that the compound in hole transmission layer be structural formula 1-4,8-15,18-20,22-34,36-37,39-42,44-48,50 compound.
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| CN105017265B (en) * | 2015-07-07 | 2017-10-17 | 上海道亦化工科技有限公司 | A kind of organic electroluminescent compounds and its device containing heterocycle |
| CN110391342B (en) * | 2018-04-17 | 2021-11-02 | 上海和辉光电股份有限公司 | Organic electroluminescent device |
| CN108752221A (en) * | 2018-06-22 | 2018-11-06 | 上海道亦化工科技有限公司 | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
| CN109535093A (en) * | 2018-12-24 | 2019-03-29 | 上海道亦化工科技有限公司 | A kind of trisubstituted benzene based compound and organic electroluminescence device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101952251A (en) * | 2007-12-20 | 2011-01-19 | 佐治亚科技研究公司 | Carbazole-based hole transport and /or electron blocking materials and /or host polymer materials |
| CN102683614A (en) * | 2011-03-08 | 2012-09-19 | 株式会社东芝 | Organic light-emitting diode, display and illuminating device |
| US8421346B2 (en) * | 2011-01-28 | 2013-04-16 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, light-emitting element, light-emitting device, lighting device, electronic device, and fluorene derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101952251A (en) * | 2007-12-20 | 2011-01-19 | 佐治亚科技研究公司 | Carbazole-based hole transport and /or electron blocking materials and /or host polymer materials |
| US8421346B2 (en) * | 2011-01-28 | 2013-04-16 | Semiconductor Energy Laboratory Co., Ltd. | Composite material, light-emitting element, light-emitting device, lighting device, electronic device, and fluorene derivative |
| CN102683614A (en) * | 2011-03-08 | 2012-09-19 | 株式会社东芝 | Organic light-emitting diode, display and illuminating device |
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