CN104892432A - Organic electroluminescent anthracene compound and organic electroluminescent device - Google Patents
Organic electroluminescent anthracene compound and organic electroluminescent device Download PDFInfo
- Publication number
- CN104892432A CN104892432A CN201510290295.5A CN201510290295A CN104892432A CN 104892432 A CN104892432 A CN 104892432A CN 201510290295 A CN201510290295 A CN 201510290295A CN 104892432 A CN104892432 A CN 104892432A
- Authority
- CN
- China
- Prior art keywords
- layer
- organic
- compound
- structural formula
- replacement
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- LONBOJIXBFUBKQ-UHFFFAOYSA-N CC(C)(c1c2)c3cc(Br)ccc3-c1ccc2Br Chemical compound CC(C)(c1c2)c3cc(Br)ccc3-c1ccc2Br LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 1
- PMWWDTLAMTVFSS-UHFFFAOYSA-N CC1(C)c2cc(N(c3ccccc3)c(cc3C4(C)C)ccc3-c(cc3)c4cc3C(C3C=CC=CC33)=C(C=CC=C4)C4=C3c3cc(cccc4)c4cc3)ccc2-c2ccccc12 Chemical compound CC1(C)c2cc(N(c3ccccc3)c(cc3C4(C)C)ccc3-c(cc3)c4cc3C(C3C=CC=CC33)=C(C=CC=C4)C4=C3c3cc(cccc4)c4cc3)ccc2-c2ccccc12 PMWWDTLAMTVFSS-UHFFFAOYSA-N 0.000 description 1
- QAAMFICOARGHHM-UHFFFAOYSA-N CCc1ccccc1-c(c(CC)c1)ccc1N(c1ccccc1)c(cc1C(C)(C)c2c3)ccc1-c2ccc3Br Chemical compound CCc1ccccc1-c(c(CC)c1)ccc1N(c1ccccc1)c(cc1C(C)(C)c2c3)ccc1-c2ccc3Br QAAMFICOARGHHM-UHFFFAOYSA-N 0.000 description 1
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N Nc1ccc(cc2)c3c1ccc1c3c2ccc1 Chemical compound Nc1ccc(cc2)c3c1ccc1c3c2ccc1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 1
- YGVDBZMVEURVOW-UHFFFAOYSA-N OB(c1c(cccc2)c2c(-c2cc(cccc3)c3cc2)c2ccccc12)O Chemical compound OB(c1c(cccc2)c2c(-c2cc(cccc3)c3cc2)c2ccccc12)O YGVDBZMVEURVOW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an organic electroluminescent anthracene compound as shown in the structural formula I. The compound is relatively good in thermal stability, high in luminous efficiency and high in luminous purity, can be used for manufacturing organic electroluminescent devices, and is applied to the fields of organic solar cells, organic thin film transistors or organic photoreceptors. The invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer contains one or more than one selected from a luminous layer, a hole injection layer, a hole transmission layer, a hole blocking layer, an electron injection layer and an electron transmission layer, and at least one layer in the organic layer contains the compound as shown in the structural formula I.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, be specifically related to a kind of anthracene class organic electroluminescent compounds and organic electroluminescence device thereof.
Background technology
Organic electroluminescence device (OLEDs) is deposit by spin coating or vacuum evaporation the device that one deck organic materials is prepared between two metal electrodes, and classical three layers of organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole produced by anode is followed through hole transmission layer the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton, then luminous.Organic electroluminescence device can regulate by the material changing luminescent layer the light launching various needs as required.
Organic electroluminescence device is as a kind of novel technique of display, there is luminous, wide viewing angle, less energy-consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, flexible and the particular advantages such as transparent display panel and environmental friendliness can be made, can be applied in flat-panel monitor and a new generation's illumination, also can 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, such as the screen such as camera and mobile phone, but current OLED due to efficiency low, the factors such as work-ing life is short restrict it and apply widely, particularly large screen display, therefore needs the efficiency improving device.And restrict the performance that one of them important factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can joule heating be produced, make organic materials easily crystallization occur, have impact on life-span and the efficiency of device, therefore, also need the electroluminescent organic material developing stability and high efficiency.
In the middle of three primary colors (red, blue, green), ruddiness and green light material have achieved very large development recently, also meet the market requirement of panel.For stable and efficient blue light material still seldom, due to the high energy gap of blue light, make the requirement for material higher, again due to stability and the optical purity Problems existing of blue phosphor materials, the blue fluorescent material therefore developing efficient stable is particularly important.
Summary of the invention
First the present invention provides a kind of anthracene derivative, and it is the compound with following structural formula I:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8separately be selected from hydrogen, deuterium, halogen, cyano group, nitro, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 or unsubstituted alkynyl;
R
9and R
10separately be selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted phenyl;
Ar
1for naphthyl; Ar
2be selected from the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl;
A is selected from O, S or CR
11r
12;
R
11and R
12separately be selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted phenyl;
Wherein preferred mode is:
R
1~ R
12separately be selected from hydrogen, methyl, ethyl, propyl group, sec.-propyl, isobutyl-, normal-butyl, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, cyclohexyl, octyl group.
Ar
2be selected from the substituted or unsubstituted following aryl of alkyl or the heteroaryl of C1-C8:
Further preferably, anthracenes luminescent compounds of the present invention is the compound of following structural 1-32:
Anthracene compounds of the present invention can be prepared by Suzuki linked reaction and Buchwald-Hartwig reaction.
Anthracene compounds 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, electron injecting layer, electron transfer layer, has one deck at least containing, for example the anthracene compounds described in structural formula I in wherein said organic layer:
Wherein R
1-R
10, Ar
1-Ar
2and the definition of A as previously mentioned.
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, blocking layer, luminescent layer, electron transfer layer and electron injecting 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 at the anthracene compounds place wherein as described in structural formula I is luminescent layer;
Preferably, the anthracene compounds wherein described in structural formula I is the compound of structural formula 1-32;
When anthracene compounds as described in structural formula I is prepared for luminescent device, can be used alone, also can use with other compound; Anthracene compounds as described in structural formula I can be used alone a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, preferred mode is that this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode further, the compound wherein containing one or more structural formula I in luminescent layer; Further preferably, the compound containing one or more structural formula 1-32 in luminescent layer.
The compound of structural formula I of the present invention can as the single luminescent layer of non-impurity-doped or doping luminescent layer, and wherein Compounds of structural formula I is as material of main part, and its concentration is the 20-99.9% of whole luminescent layer weight, and preferred 80-99%, is more preferably 90-99%; During as guest materials, its concentration is the 0.1-50% of whole luminescent layer, is preferably 0.5%-10%.
The total thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
Organic electroluminescence device of the present invention is when using the present invention to have the compound of structural formula I, can to arrange in pairs or groups use other materials, as medium on hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer or blocking layer, and obtain blue light, green glow, gold-tinted, ruddiness 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, can effectively hole be transferred to luminescent layer from anode.Other small molecules and macromolecular organic compound can be comprised, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group six mix triphen (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 organic electroluminescence device of the present invention, has the good characteristics of luminescence, can regulate the scope of visible ray as required.Have except Compounds of structural formula I except of the present invention, can also containing, for example lower compound, but be not limited thereto, naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, benzimidazoles compound, furfuran compound, organic metal chelate complex in the wrong.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, effectively during electronics is from cathode transport to luminescent layer, can have very large electronic mobility.Following compound can be selected, but be not limited thereto, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocyclic compound, quinolines, phenanthroline compounds, metallo-chelate (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, mainly be selected from basic metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but be not limited thereto, the oxide compound of basic metal, alkaline-earth metal, rare earth metal, alkali-metal oxide compound or halogenide, alkaline-earth metal or halogenide, the oxide compound of rare earth metal or the organic complex of halogenide, basic metal or alkaline-earth metal; Be preferably lithium, lithium fluoride, Lithium Oxide 98min, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, Calcium Fluoride (Fluorspan), calcium oxide, magnesium, magnesium fluoride, magnesiumcarbonate, magnesium oxide, these compounds can be used alone also can mixture use, also can with other electroluminescent organic materials with the use of.
Every one deck of organic layer in organic electroluminescence device of the present invention, can be prepared by modes such as vacuum vapour deposition, molecular beam vapour deposition method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or spray ink Printings.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the anthracene compounds of the present invention as described in structural formula I, has better thermostability, high-luminous-efficiency, high luminance purity.The organic electroluminescence device adopting this anthracene compounds to make has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
Accompanying drawing explanation
Fig. 1 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.
Embodiment
In order to more describe the present invention in detail, especially exemplified by following example, but be not limited thereto.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate 1-1
In there-necked flask; add N-phenyl-9; 9-dimethyl-2-fluorenamine (5.6g; 20mmol); bromo-9, the 9-dimethyl fluorene (7g of 2,7-bis-; 20mmol), potassium tert.-butoxide (3.3g; 30mmol), palladium (0.1g), tri-butyl phosphine a tetrafluoro borate (0.3g), 100mL toluene, reflux 12 hours, adds water under nitrogen protection; layering; organic over anhydrous dried over sodium sulfate, concentrated, thick product uses column chromatography and obtains 7.6g; productive rate is 68.5%, MS (m/z): 555.1.
The synthesis of compound 1
In there-necked flask; add intermediate 1-1 (1g, 18mmol), 10-(2-naphthyl) anthracene-9-boric acid (0.63g, 18mmol), tetra-triphenylphosphine palladium (50mg), the wet chemical of 10mL 2M, 15mL tetrahydrofuran (THF); reflux 10 hours under nitrogen protection; cooling, with dichloromethane extraction, dry; concentrated; thick product uses column chromatography and obtains 1.1g, and productive rate is 79%, MS+H (m/z): 780.4.
Embodiment 2
The synthesis of compound 10
The synthesis of intermediate 10-1
In there-necked flask; add 4-bromo-cumene (10g; 50mmol), 3-amido diphenylene-oxide (9.2g; 50mmol), potassium tert.-butoxide (11.2g; 100mmol), palladium (0.1g), tri-butyl phosphine a tetrafluoro borate (0.3g), 100mL toluene; reflux 12 hours under nitrogen protection; add water; layering; organic over anhydrous dried over sodium sulfate, concentrated, thick product uses column chromatography and obtains 12.5g; productive rate is 83%, MS (m/z): 301.4.
The synthesis of intermediate 10-2
In there-necked flask; add intermediate 10-1 (3.0g; 10mmol), 2; 7-bis-bromo-9; 9-dimethyl fluorene (3.5g; 10mmol), potassium tert.-butoxide (2.2g; 20mmol), palladium (0.1g), tri-butyl phosphine a tetrafluoro borate (0.3g), 50mL toluene, reflux 12 hours, adds water under nitrogen protection; layering; organic over anhydrous dried over sodium sulfate, concentrated, thick product uses column chromatography and obtains 2.3g; productive rate is 40%, MS (m/z): 571.2.
The synthesis of compound 10
In there-necked flask; add intermediate 10-2 (1g, 17.5mmol), 10-(2-naphthyl) anthracene-9-boric acid (0.61g, 17.5mmol), tetra-triphenylphosphine palladium (50mg), the wet chemical of 10mL 2M, 15mL tetrahydrofuran (THF); reflux 10 hours under nitrogen protection; cooling, with dichloromethane extraction, dry; concentrated; thick product uses column chromatography and obtains 0.9g, and productive rate is 65%, MS+H (m/z): 796.7.
Embodiment 3
The synthesis of compound 17
In there-necked flask; add intermediate 1-1 (1g, 18mmol), 10-(1-naphthyl) anthracene-9-boric acid (0.63g, 18mmol), tetra-triphenylphosphine palladium (50mg), the wet chemical of 10mL 2M, 15mL tetrahydrofuran (THF); reflux 10 hours under nitrogen protection; cooling, with dichloromethane extraction, dry; concentrated; thick product uses column chromatography and obtains 1.1g, and productive rate is 79%, MS+H (m/z): 780.4.
Embodiment 4
The synthesis of compound 26
In there-necked flask; add intermediate 10-2 (1g, 17.5mmol), 10-(1-naphthyl) anthracene-9-boric acid (0.61g, 17.5mmol), tetra-triphenylphosphine palladium (50mg), the wet chemical of 10mL 2M, 15mL tetrahydrofuran (THF); reflux 10 hours under nitrogen protection; cooling, with dichloromethane extraction, dry; concentrated; thick product uses column chromatography and obtains 0.84g, and productive rate is 60%, MS+H (m/z): 796.4.
Embodiment 5
The preparation of organic electroluminescence device
The compound of embodiment of the present invention 1-4 is used to prepare 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 use oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the hole transmission layer 130 that 60nm is thick.
Then, evaporation the compounds of this invention on hole transmission layer, forms the luminescent layer 140 that 30nm is thick.
Then, the Alq that evaporation 30nm is thick on luminescent layer
3as electron transfer layer 150.
Finally, evaporation 1nm LiF is that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device (structural representation is shown in Fig. 1) records at 20mA/cm with Photo Research PR650 spectrograph
2the device performance of lower embodiment 7-12 is as shown in table 1.
Comparative example 1
Except luminescent layer MADN replaces except the compounds of this invention, other the same with embodiment 1.
Prepared device (structural representation is shown in Fig. 1) with Photo Research PR650 spectrograph record at 20mA/cm
2lower device performance is as shown in table 1.
Table 1
| Luminescent material | Voltage (V) | Current efficiency (cd/A) | Color |
| 1 | 4.9 | 2.6 | Blue |
| 10 | 4.8 | 2.7 | Blue |
| 17 | 5.2 | 2.2 | Blue |
| 26 | 5.0 | 2.4 | Blue |
| MADN | 6.3 | 1.4 | Blue |
As can be seen from the above table, the device performance of compound of the present invention is better than embodiment.
The structural formula of compound described in device is as follows:
。
Claims (10)
1. an anthracene class organic electroluminescent compounds, is characterized in that it is the compound with following structural formula I:
Wherein, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8separately be selected from hydrogen, deuterium, halogen, cyano group, nitro, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl, the replacement of C2-C8 or unsubstituted thiazolinyl, the replacement of C2-C8 or unsubstituted alkynyl;
R
9and R
10separately be selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted phenyl;
Ar
1for naphthyl; Ar
2be selected from the replacement of C6-C30 or unsubstituted aryl, the replacement of C3-C30 or unsubstituted heteroaryl;
A is selected from O, S or CR
11r
12;
R
11and R
12separately be selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted phenyl.
2. anthracene class organic electroluminescent compounds according to claim 1, is characterized in that wherein
R
1~ R
12separately be selected from hydrogen, methyl, ethyl, propyl group, sec.-propyl, isobutyl-, normal-butyl, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, cyclohexyl, octyl group.
Ar
2be selected from the substituted or unsubstituted following aryl of alkyl or the heteroaryl of C1-C8:
3. anthracene class organic electroluminescent compounds according to claim 1, is characterized in that it is the compound of following structural 1-32:
4. described in any one of claim 1-3, anthracene class organic electroluminescent compounds is preparing the application in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith.
5. an organic electroluminescence device, it 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, electron injecting layer, electron transfer layer, it is characterized in that in organic layer, at least one deck includes anthracene compounds as claimed in claim 1.
6. organic electroluminescence device according to claim 5, is characterized in that the layer at the anthracene compounds place as described in structural formula I is luminescent layer.
7. organic electroluminescence device according to claim 5, is characterized in that the anthracene compounds as described in structural formula I is used alone, or and other compound use.
8. organic electroluminescence device according to claim 5, the anthracene compounds that it is characterized in that as described in structural formula I is used alone a kind of compound wherein, or uses two or more the compound in structural formula I simultaneously.
9. organic electroluminescence device according to claim 5, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, it is characterized in that the compound containing one or more structural formula I in luminescent layer.
10. organic electroluminescence device according to claim 5, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer and negative electrode, it is characterized in that the structural formula containing one or more in luminescent layer is the compound of 1-32.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510290295.5A CN104892432B (en) | 2015-05-29 | 2015-05-29 | A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510290295.5A CN104892432B (en) | 2015-05-29 | 2015-05-29 | A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104892432A true CN104892432A (en) | 2015-09-09 |
| CN104892432B CN104892432B (en) | 2017-07-21 |
Family
ID=54025455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510290295.5A Active CN104892432B (en) | 2015-05-29 | 2015-05-29 | A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104892432B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113968835A (en) * | 2020-07-22 | 2022-01-25 | 上海和辉光电股份有限公司 | Substituted anthracene compound and organic electroluminescent device comprising same |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20020062922A (en) * | 2000-08-10 | 2002-07-31 | 미쯔이카가쿠 가부시기가이샤 | Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element |
| JP2003229273A (en) * | 2002-02-01 | 2003-08-15 | Mitsui Chemicals Inc | Organic electric-field light emitting element |
| CN101550085A (en) * | 2008-03-20 | 2009-10-07 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN102245733A (en) * | 2008-12-05 | 2011-11-16 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103242174A (en) * | 2012-02-07 | 2013-08-14 | 三星显示有限公司 | Amine-based compound and organic light-emitting diode including the same |
-
2015
- 2015-05-29 CN CN201510290295.5A patent/CN104892432B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20020062922A (en) * | 2000-08-10 | 2002-07-31 | 미쯔이카가쿠 가부시기가이샤 | Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element |
| JP2003229273A (en) * | 2002-02-01 | 2003-08-15 | Mitsui Chemicals Inc | Organic electric-field light emitting element |
| CN101550085A (en) * | 2008-03-20 | 2009-10-07 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN102245733A (en) * | 2008-12-05 | 2011-11-16 | 葛来西雅帝史派有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103242174A (en) * | 2012-02-07 | 2013-08-14 | 三星显示有限公司 | Amine-based compound and organic light-emitting diode including the same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113968835A (en) * | 2020-07-22 | 2022-01-25 | 上海和辉光电股份有限公司 | Substituted anthracene compound and organic electroluminescent device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104892432B (en) | 2017-07-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105153130B (en) | Triazine derivative electron transport compound and its organic electroluminescence device | |
| CN106831313A (en) | A kind of compound and its organic electroluminescence device with triaryl naphthalene | |
| CN105481811A (en) | Compound with screw structure and organic electroluminescent device thereof | |
| CN105175313A (en) | Hole injection compound and organic electroluminescent device | |
| CN109053698A (en) | A kind of aromatic amine compound and luminescent device containing dibenzofurans | |
| CN109265450A (en) | A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo | |
| CN105461685A (en) | Compound containing quinoxaline perssad and organic electroluminescence device of compound | |
| CN109336772A (en) | A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device | |
| CN105294663A (en) | Pyridine-containing compound and organic light-emitting device | |
| CN105061439B (en) | A kind of organic electroluminescent compounds and its organic electroluminescence device | |
| CN105175314A (en) | Hole transporting compound and organic electroluminescent device thereof | |
| CN109535175A (en) | A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring | |
| CN106831798B (en) | Compound and its organic electroluminescence device containing five-membered ring structure | |
| CN105753849A (en) | Compound containing quinoxaline and pyridine groups and organic electroluminescent device thereof | |
| CN105001229B (en) | A kind of organic electroluminescent compounds and its device with spiro structure | |
| CN109320495A (en) | A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure | |
| CN106749289B (en) | A kind of organic electroluminescent compounds and its luminescent device with spiro structure | |
| CN105503801A (en) | Aromatic amine luminous compound and organic electroluminescence device manufactured through same | |
| CN106554358B (en) | A kind of organic electroluminescent compounds and its luminescent device with spiro structure | |
| CN105461707A (en) | Phosphorescent host compound and OELD (Organic Electroluminescent Device) thereof | |
| CN105218541A (en) | A kind of phosphorescence host compound and organic electroluminescence device thereof | |
| CN105669466A (en) | Compound based on fluoranthene and organic electroluminescence device | |
| CN106543157B (en) | A kind of electroluminescent organic material and its organic electroluminescence device | |
| CN109232495A (en) | A kind of the triaromatic amine compound and luminescent device of thiophene containing indeno and furans | |
| CN108976196A (en) | A kind of aromatic amine compound of the spiro structure containing five-membered ring and application thereof and luminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant |