CN100427467C - Compound and organic LED and display containing the compound - Google Patents
Compound and organic LED and display containing the compound Download PDFInfo
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- CN100427467C CN100427467C CNB2005100526639A CN200510052663A CN100427467C CN 100427467 C CN100427467 C CN 100427467C CN B2005100526639 A CNB2005100526639 A CN B2005100526639A CN 200510052663 A CN200510052663 A CN 200510052663A CN 100427467 C CN100427467 C CN 100427467C
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Abstract
The present invention provides a compound which has the chemical formula (I) structure, wherein X1 and X2 are respectively and independently aryl groups whose carbon number is from 10 to 25, heterochromatic aryl groups, toluylene groups and silicyl aryl groups or aryl silyl groups; n represents an integral number whose range is from 0 to 2; L represents an aryl group or a heterochromatic aryl group; A1, A2 and A3 are respectively and independently aryl groups or heterochromatic aryl group. The present invention also provides an organic light emitting diode and a display, which respectively comprise the compound of the present invention.
Description
Technical field
The present invention relates to a kind of compound, particularly relate to a kind of compound that is used for Organic Light Emitting Diode.
Background technology
Organic electroluminescence device (organic electroluminescent devices (organic electroluminescence device) or polymer electroluminescent devices (polymer electroluminescent device)) was from 1987, Kodak just causes the attention of industry after developing first high-level efficiency organic electroluminescence device.Because organic electroluminescence device has high brightness, frivolous, luminous, low consumpting power, do not need backlight, limit at no visual angle, processing procedure is simple and easy and good characteristic such as high reaction rate, be regarded as the rising star of flat-panel screens.
Electroluminescent principle is: the organic semiconductor thin film device, under the extra electric field effect, electronics and hole are injected by negative electrode and anode respectively, and in this device, transmit, when electronics, hole after luminescent layer meets, electronics and hole form exciton (exciton) in conjunction with (recombination) again, and exciton is given light emitting molecule with transmission ofenergy under electric field action, and light emitting molecule just discharges the form of energy with light.General simple device architecture is: at anode (ITO, indium tin oxide (tin indium oxide)) goes up evaporation hole transmission layer (hole transport layer), follow evaporation luminescent layer (light emittinglayer), evaporation hole blocking layer (hole blocking layer) and electron transfer layer (electrontransport layer) again, at last on electron transfer layer electrode evaporation as negative electrode.The device that some multilayered structures are also arranged is that suitable organic materials evaporation is used as hole injection layer (hole injection layer) between anode and hole mobile material, or evaporation is used as electron injecting layer (electron injection layer) between negative electrode and electron transport material, use the injection efficiency that improves current carrier, and then reach the reduction driving voltage and increase current carrier again in conjunction with probability.
Because synthetic technology constantly brings forth new ideas, academia, industrial community have been developed the luminescent material of various organic synthesis compounds as organic electroluminescence device, at this, promptly based on the luminous organic material of carbazole (carbazole) structure as the discussion emphasis.At present, the application of luminous organic material in device with carbazole structure is as follows, for example can be used as hole mobile material, its pertinent literature comprises U.S. Patent application 6660410B2 number, No. the 2004071500th, Japanese Patent Laid Open Publication and world patent application 03/080761A1 number etc.; Also can be used as phosphorescent light-emitting materials, its pertinent literature comprises Japanese patent application 08-003547 number and 09-310066 number etc.; Or can be used as fluorescence luminescent material, its pertinent literature comprises U.S. Patent application 6649772B2 number and Japanese patent application 07-150138 number etc.
Yet, the all not mentioned luminous organic material with carbazole structure of above-mentioned prior art can be applicable to the blue-fluorescence device, and existing carbazole structure its 3, substituting group on 6 positions and the nitrogen-atoms all belongs to and contains nitrogen-atoms or the more simple aromatic base of structure, with regard to these two portions, synthetic novel blue-fluorescence luminescent material still has sizable development space.
Summary of the invention
In view of this, the invention provides a kind of compound, have the structure of following chemical formula (I):
X wherein
1And X
2Be respectively 10～25 aryl (aryl), heteroaryl (heteroaryl), diphenylethyllene (stilbenyl), silyl aryl (silylaryl) or aryl silyl (arylsilyl) independently for carbon number; N is 0～2 integer; L is aryl or heteroaryl; And A
1, A
2With A
3Be aryl or heteroaryl independently respectively.
The present invention provides a kind of Organic Light Emitting Diode in addition, comprises negative electrode and anode, and luminescent layer, and this luminescent layer is arranged between this negative electrode and this anode and comprises above-claimed cpd.
The present invention provides a kind of indicating meter in addition, comprises above-mentioned Organic Light Emitting Diode, and the driving circuit that is coupled to Organic Light Emitting Diode, to drive this Organic Light Emitting Diode.
Description of drawings
The 1st figure is the diagrammatic cross-section of organic LED structure according to an embodiment of the invention.
The 2nd figure is the vertical view of display device structure according to an embodiment of the invention.
The 3rd figure is the graph of a relation of the voltage-luminosity of Organic Light Emitting Diode according to an embodiment of the invention.
Embodiment
The invention provides a kind of compound, have the structure of chemical formula (I):
In chemical formula (I), X
1And X
2Can be identical or different substituting group, respectively independently for the carbon number carbon number be 10～25 aryl, heteroaryl, diphenylethyllene, silyl aryl or aryl silyl, comprise
R wherein
1And R
2Can be identical or different substituting group, be alkyl, aryl or heteroaryl independently respectively, and Ar refers to aryl.L can be aryl or heteroaryl in addition, comprises
Wherein each R can be identical or different substituting group, comprises alkyl, aryl or heteroaryl.N in the chemical formula (I) can be
0～2。And A
1, A
2With A
3Can be identical or different substituting group, is aryl or heteroaryl respectively independently.
Below list the particular instance of The compounds of this invention:
Chemical formula (I) can be synthetic by following manner, at first, synthesizing earlier according to general organic synthesis technology for example is 3,6-two bromo-9-phenyl carbazoles (3,6-dibromo-9-phenyl carbazole), 3,6-two bromo-9-(9,9-diethyl-9H-fluorenes-2-yl) carbazole (3,6-dibromo-9-(9,9-Diethyl-9H-fluoren-2-yl)-carbazole) or 3 ', 6 '-two bromo-9-phenyl-9H-[2,9 '] two carbazoles (3 ', 6 '-Dibromo-9-phenyl-9H-[2,9 '] bicarbazole) and carbazole derivative and for example be 1-pyrenyl boric acid (1-pyrenyl boronicacid), 9, the boric acid derivatives of 9-phenylbenzene-9H-fluorenyl-2-boric acid (9,9-diphenyl-9H-fluorenyl-2-boronic acid) or 4-triphenyl silyl-phenylo boric acid (4-triphenylsilyl-phenyl boronic acid).Then, under alkaline condition, (for example add salt of wormwood (K
2CO
3)) mix carbazole derivative, boric acid derivatives, catalyzer and solvent and place reaction flask, wherein the catalyzer of Tian Jiaing can be four-(triphenyl) phosphine palladium (Tetrakis (triphenylphosphine) palladium (0), Pd (PPh
3)
4), solvent can be ethanol or dimethyl ether (dimethyl ether, DME).After treating that boiling reaction is spent the night, drain solvent.Then with solvent for example ethyl acetate (ethyl acetate) or ether (diethyl ether) aqueous layer extracted, afterwards, with the washed with de-ionized water organic layer and for example being sal epsom (MgSO
4) siccative remove moisture, the mixture that organic layer obtains after concentrating is again with the chromatographic column purification, can obtain the compound (chemical formula (I)) that the present invention is formed by carbazole derivative and boric acid derivatives condensation reaction.
The present invention obtains compound based on carbazole structure in the mode of chemosynthesis, it is 3 of carbazole structure, introduce the aromatic nucleus that resonance effect (conjugation effect) is preferable and structure is complicated on 6 positions and the nitrogen-atoms respectively, make the spectrum of giving out light of compound drop in the blue light region really, thus, this fluorescent chemicals quite is suitable as the main body (host) or hotchpotch (dopant) material of blue-fluorescence device luminescent layer, and has splendid thermostability and film-forming properties.
The present invention also provides a kind of Organic Light Emitting Diode, comprises negative electrode and anode, and luminescent layer, and this luminescent layer is arranged between negative electrode and the anode and comprises above-claimed cpd.
At least one must be transparency electrode in above-mentioned negative electrode and the anode, another can be metal, metal alloy or transparent metal oxide, the material of promptly representing two electrodes can be identical or different, wherein metal can be aluminium, calcium, silver, nickel, chromium, titanium or magnesium, metal alloy can be the magnesium silver alloys, and transparent metal oxide can be tin indium oxide (ITO), azo (AZO), zinc oxide (ZnO), indium nitride (InN) or stannic oxide (SnO
2).
Above-mentioned luminescent layer can add other blue-fluorescence luminescent material, for example CBP, TCTA, CzTT, TPBI, TAZ, BAlq, mCP, UGH1, UGH2 or UGH3.Above-mentioned Organic Light Emitting Diode is except that electrode and luminous layer structure, also can comprise electron transfer layer or the electron injecting layer that is arranged between negative electrode and the luminescent layer or be arranged at anode and luminescent layer between hole transmission layer or hole injection layer, wherein the material of electron transfer layer for example is t-Bu-PBD, Alq3, BeBq, TAZ, Almq3, BAlq or TPBI, the material of electron injecting layer for example is lithium fluoride or Lithium Oxide 98min, the material of hole transmission layer for example is HTM2, TPD, NPB, PPD, TBPB, spiro (spiral shell)-TAD, spiro (spiral shell)-NPB, TPTE2, TPTE1, NTPA or DNPD, and the material of hole injection layer for example is BPhen, BCP, BAlq, CF-X, TAZ or CF-Y.Following structural is represented in the abbreviation of above-mentioned each compound:
The making of Organic Light Emitting Diode of the present invention then, is described with reference to figure 1.At first, provide anode 12, afterwards, evaporation hole injection layer 14, hole transmission layer 16, luminescent layer 18, electron transfer layer 20, electron injecting layer 22 and negative electrode 24 after encapsulating, are promptly finished the making of Organic Light Emitting Diode 10 successively.
The present invention also provides a kind of indicating meter, comprises above-mentioned Organic Light Emitting Diode, and the driving circuit that is coupled to Organic Light Emitting Diode, and with the driving Organic Light Emitting Diode, and driving circuit can comprise thin film transistor.
Detailed formation with reference to figure 2 explanations indicating meter 100 of the present invention.At least include OLED 120 and driving circuit 140 on the display device structure 100, wherein driving circuit 140 is coupled to Organic Light Emitting Diode 120 to drive Organic Light Emitting Diode 120.
Below by several embodiment so that further specify the features and advantages of the present invention.
Embodiment
Embodiment 1
9-phenyl-3, and 6-two pyrenes-1-base-9H-carbazole (9-Phenyl-3,6-di-pyren-1-yl-9H-carbazole)
Synthesizing of (compound 6)
Synthesis step:
Synthesizing of (1) 3,6-two bromo-9-phenyl carbazoles (3,6-dibromo-9-phenyl carbazole) (compound 3)
At first, mix 8 grams, 1,7.6 milliliter of the compound of 47.9 mmoles, the bromobenzene (bromobenzene) of 71.9 mmoles, the palladium (Pd (OAc) of the tert.-butoxy sodium (t-BuONa) of 6.8 grams, 71.9 mmoles and 268 milligrams, 1.2 mmoles
2) and add in the reaction flask contain 80 milliliters of toluene (toluene) and stir, afterwards, add 970 milligrams, the tertiary butyl phosphine (t-Bu of 4.8 mmoles
3P), react under toluene (toluene) the ebullient state to the next day and all react completely to confirm all compounds 1 with TLC sheet following response.Afterwards, utilize the mode of concentrating under reduced pressure that toluene is all drained.Then, add 30 milliliters ethyl acetate extraction water layer three times, subsequently, add 60 milliliters washed with de-ionized water organic layer and with sal epsom (MgSO
4) remove moisture, organic layer obtains the chocolate mixture behind concentrating under reduced pressure, utilize fresh chromatographic column (normal hexane: ethyl acetate=95: 5) purify, can obtain 10.4 grams, productive rate and be 90% compound 2 again.
Under condition of ice bath, N-bromo-succinimide (N-Bromosuccinimide with 16.1 grams, 90.6 mmoles, NBS) add and to contain 10 and digest in the reaction flask of compound 2 (41.2 mmole) and 20 milliliters of tetrahydrofuran (THF)s (THF), at room temperature react to the next day.Afterwards, the Sulfothiorine (Na that adds 40 milliliters
2S
2O
4) saturated aqueous solution and utilize the concentrating under reduced pressure method that tetrahydrofuran (THF) (THF) is drained, then,, can obtain 6.5 to restrain, productive rate is 70% high-purity compound 3 with deionized water and normal hexane washing and precipitating solid.
(2) 1-pyrenyl boric acid (1-pyenylboronic acid) (compound 5) is synthetic
Under-76 ℃ condition, with (8.9 milliliters of the n-Butyl Lithiums (n-BuLi) of 2.5M, 22.3 mmole) adding contains compound 4 (5 grams, 20.3 mmole) and in the round-bottomed flask of tetrahydrofuran (THF) (THF) stirred 30 minutes, afterwards, with 4.6 milliliters, 40.6 the trimethyl borate of mmole (trimethyl borate) (d=0.927) slowly is added dropwise in the round-bottomed flask, wait to rise again to room temperature afterreaction 3 hours, then, add 20 milliliters deionized water and 1 milliliter 2M hydrochloric acid, continue to stir 30 minutes, afterwards, with the washed with de-ionized water organic layer and utilize sal epsom (MgSO
4) remove moisture, organic layer can obtain tawny solid compound 5 behind concentrating under reduced pressure, and this solid cleans through normal hexane that can to obtain 3.0 grams, productive rate be 60% high-purity compound 5.
(3) 9-phenyl-3, (9-Phenyl-3,6-di-pyren-1-yl-9H-carbazole) (compound 6) is synthetic for 6-two pyrenes-1-base-9H-carbazole
Embodiment 2
3,6-two-(9,9-diethyl-9H-fluorenes-2-yl)-9-(4-triphenyl silyl-phenyl)-9H-azoles
(3, and 6-bis-(9,9-diethyl-9H-fluoren-2-yl)-9-(4-triphenylsilyl-phenyl)-9H-carbazole)
Synthesizing of (compound 12)
Synthesis step:
Synthesizing of (1) 3,6-two bromo-9-(4-triphenyl silyl-phenyl) carbazole (3,6-dibromo-9-(4-triphenylsilyl-phenyl) carbazole) (compound 11)
At first, the tert.-butoxy sodium (t-BuONa) and 268 milligrams, the palladium (Pd (OAc) of 1.2 mmoles that mix 1-triphenyl silyl-4-bromobenzene (1-triphenylsiyl-4-bromobenzene), 6.8 grams, 71.9 mmoles of compound 3,29 grams, 71.9 mmoles of 8 grams, 47.9 mmoles
2) add to contain in 80 milliliters of reaction of toluene bottles and stir, afterwards, add 970 milligrams, the tertiary butyl phosphine (t-Bu of 4.8 mmoles
3P), react under the toluene ebullient state to the next day and all react completely to confirm all compounds 3 with TLC sheet following response.Afterwards, utilize the mode of concentrating under reduced pressure that toluene is all drained.Then, add 30 milliliters ethyl acetate extraction water layer three times, subsequently, add 60 milliliters washed with de-ionized water organic layer and with sal epsom (MgSO
4) remove moisture, organic layer obtains the chocolate mixture behind concentrating under reduced pressure, utilize fresh chromatographic column (normal hexane: ethyl acetate=95: 5) purify, can obtain 21.6 grams, productive rate and be 90% compound 10 again.
Under condition of ice bath, the N-bromo-succinimide (NBS) of 16.1 grams, 90.6 mmoles added contains 10 and digest in the reaction flask of compound 10 (24.2 mmole) and 20 milliliters of tetrahydrofuran (THF)s (THF), at room temperature react to the next day.Afterwards, the Sulfothiorine (Na that adds 40 milliliters
2S
2O
4) saturated aqueous solution and utilize the concentrating under reduced pressure method that tetrahydrofuran (THF) (THF) is drained, then,, can obtain 11.1 grams, productive rate and be 70% high-purity compound 11 with deionized water and normal hexane washing and precipitating solid.
Synthesizing of (2) 9,9-diethyl-9H-fluorenes-2-boric acid (9,9-diethyl-9H-fluorene-2-boronic acid) (compound 9)
Under the condition of 0 degree Celsius, the tert.-butoxy potassium (t-BuOK) of 5.6 grams, 50 mmoles added in the round-bottomed flask of the 2-bromo-9H-fluorenes (2-bromo-9H-fluorene) contain 5 grams, 20 mmoles and tetrahydrofuran (THF) (THF) and stirred 30 minutes, afterwards, the bromination ethane (bromoethane) that adds 6.5 grams, 60 mmoles reacted 2 hours, after question response stops, add the ethyl acetate extraction water layer, subsequently, add the washed with de-ionized water organic layer and with sal epsom (MgSO
4) remove moisture, organic layer can obtain the compound 8 (4.2 grams, productive rate 70%) of tawny liquid behind concentrating under reduced pressure.
Under-76 ℃ condition, the n-Butyl Lithium (n-BuLi) (6.3 milliliters, 15.8 mmoles) of 2.5M added contain compound 8 (4 grams, 13.2 mmoles) and tetrahydrochysene and mutter and stirred 30 minutes in the round-bottomed flask of (THF), afterwards, slowly be added dropwise to 4.4 milliliters, the trimethyl borate (d=0.927) of 39.6 mmoles in the round-bottomed flask, wait to rise again to room temperature afterreaction 3 hours, then, add 20 milliliters deionized water and 1 milliliter 2M hydrochloric acid, continue to stir 30 minutes, afterwards, with the washed with de-ionized water organic layer and utilize sal epsom (MgSO
4) remove moisture, organic layer can obtain tawny solid compound 9 behind concentrating under reduced pressure, and this solid cleans through normal hexane that can to obtain 2.2 grams, productive rate be 73% high-purity compound 9 again.
(3) 3,6-two-(9,9-diethyl-9H-fluorenes-2-yl)-9-(4-triphenyl silyl-phenyl)-9H-carbazole (3, and 6-bis-(9,9-diethyl-9H-fluoren-2-yl)-9-(4-triphenylsilyl-phenyl)-9H-carbazole) (compound 12) synthetic
Mix compound 11,2 grams of 5.6 grams, 8.5 mmoles, compound 9,1 grams of 15 mmoles, four-(triphenyl) phosphine palladium (Pd (PPh of 0.9 mmole
3)
4) and 3.2 the gram, 23.5 mmoles salt of wormwood (K
2CO
3) and add in the reaction flask contain 80 milliliters of ethanol and 40 milliliters of dimethyl ethers (DME) and stir, react under the ebullient state to the next day and all react completely to confirm all compounds 11 with TLC sheet following response.Then, utilize the mode of concentrating under reduced pressure that solvent is all drained.Afterwards, add 30 milliliters ethyl acetate extraction water layer three times, subsequently, add 60 milliliters washed with de-ionized water organic layer and with sal epsom (MgSO
4) remove moisture, organic layer obtains the chocolate mixture behind concentrating under reduced pressure, utilize fresh chromatographic column (normal hexane: ethyl acetate=95: 5) purify, can obtain 5.6 grams, productive rate and be 70% compound 12 again.
The making of Organic Light Emitting Diode
Making with reference to figure 1 explanation Organic Light Emitting Diode of the present invention (device A).At first, tin indium oxide (Indium-tin-oxide is provided, ITO) anode 12 and handle it with ultraviolet and ozone, the person of connecing, evaporation 2T-NATA is as hole injection layer 14 on ito anode 12, afterwards, evaporation NPB (4 on hole injection layer 14,4 '-bis[N-(naphthyl)-N-phenyl-amino] biphenyl (4,4 '-two [N-(naphthyl)-N-phenyl-amino] phenyl)), then, on hole transmission layer 16, be total to evaporation 9-phenyl-3 as hole transmission layer 16,6-two pyrenes-1-base-9H-carbazole (9-Phenyl-3,6-di-pyren-1-yl-9H-carbazole) with DSA as luminescent layer (light emitting layer) 18, afterwards, evaporating Al q3 is as electron transfer layer 20 on luminescent layer 18, afterwards, evaporation lithium fluoride (LiF) is as electron injecting layer 22 on electron transfer layer 20, and last, plated aluminum on electron injecting layer 22 (Al) metal is as negative electrode 24, after encapsulating, promptly finish the making of Organic Light Emitting Diode 10.
Next, with reference to figure 3 explanation Organic Light Emitting Diodes of the present invention (device A) and the difference of existing Organic Light Emitting Diode (device B) on luminosity, wherein the structure of device B is similar to device A substantially, difference is that the luminescent layer of device B is the composition of existing ADN and hotchpotch, the luminescent layer of device A then is to mix fluorescent chemicals of the present invention (9-phenyl-3,6-two pyrenes-1-base-9H-carbazole (9-Phenyl-3,6-di-pyren-1-yl-9H-carbazole)).
By finding out among the figure, when operating voltage was 6 volts, the luminosity of device A was 1391cd/cm
2, and device B only is 456cd/cm
2, differed 3 times more than, it serves to show that Organic Light Emitting Diode that the present invention makes compares with existing device and have high luminous efficiency really, be a kind of Organic Light Emitting Diode of high brightness.
Though the present invention discloses as above with preferred embodiment, so it is not in order to limit the present invention.Any those skilled in the art is not deviating from the spirit and scope of the invention, can change and retouching.Therefore protection scope of the present invention should be as the criterion with appending claims.
Claims (14)
1. a compound has the structure of chemical formula (I)
X wherein
1And X
2Be independently selected from following one respectively:
R wherein
1And R
2Be alkyl independently respectively;
N is 0～2 integer, and L is for being selected from following one:
And A
1, A
2With A
3Be aryl independently respectively.
2. compound as claimed in claim 1, wherein X
1And X
2Be identical substituting group.
3. compound as claimed in claim 1 or 2, wherein R
1And R
2Be identical substituting group.
4. compound as claimed in claim 1, wherein A
1, A
2With A
3Be identical substituting group.
5. compound as claimed in claim 1, wherein chemical formula (I) comprises
6. compound as claimed in claim 1, wherein chemical formula (I) comprises
7. Organic Light Emitting Diode comprises:
Negative electrode and anode; And
Luminescent layer, this luminescent layer is arranged between negative electrode and the anode, and comprises the described compound of claim 1.
8. Organic Light Emitting Diode as claimed in claim 7 also comprises the electron transfer layer that is arranged between negative electrode and the luminescent layer.
9. Organic Light Emitting Diode as claimed in claim 7 also comprises the electron injecting layer that is arranged between negative electrode and the luminescent layer.
10. Organic Light Emitting Diode as claimed in claim 7 also comprises the hole transmission layer that is arranged between anode and the luminescent layer.
11. Organic Light Emitting Diode as claimed in claim 7 also comprises the hole injection layer that is arranged between anode and the luminescent layer.
12. Organic Light Emitting Diode as claimed in claim 7, wherein this compound fluorescence of look that turns blue.
13. an indicating meter comprises:
Organic Light Emitting Diode as claimed in claim 7; And
Be coupled to the driving circuit of Organic Light Emitting Diode, to drive this Organic Light Emitting Diode.
14. indicating meter as claimed in claim 13, wherein driving circuit comprises thin film transistor.
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|---|---|---|---|
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| KR101528945B1 (en) * | 2007-07-27 | 2015-06-15 | 도레이 카부시키가이샤 | Light-emitting device material and light-emitting device |
| KR102357467B1 (en) * | 2014-07-22 | 2022-02-04 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescence Device |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1407053A (en) * | 2001-08-13 | 2003-04-02 | 三星Sdi株式会社 | Blue light emitting compound and electroluminescert device with it as color display substance |
| WO2003080761A1 (en) * | 2002-03-25 | 2003-10-02 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
| US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| JP2004002351A (en) * | 2002-03-27 | 2004-01-08 | Tdk Corp | Organic el device |
| CN1488707A (en) * | 2003-08-13 | 2004-04-14 | 复旦大学 | Blue organic electroluminescent material and preparing method thereof |
| CN1490312A (en) * | 2003-09-05 | 2004-04-21 | �廪��ѧ | Carbazole derivative and its application in electroluminescent device |
-
2005
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| CN1407053A (en) * | 2001-08-13 | 2003-04-02 | 三星Sdi株式会社 | Blue light emitting compound and electroluminescert device with it as color display substance |
| WO2003080761A1 (en) * | 2002-03-25 | 2003-10-02 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
| JP2004002351A (en) * | 2002-03-27 | 2004-01-08 | Tdk Corp | Organic el device |
| CN1488707A (en) * | 2003-08-13 | 2004-04-14 | 复旦大学 | Blue organic electroluminescent material and preparing method thereof |
| CN1490312A (en) * | 2003-09-05 | 2004-04-21 | �廪��ѧ | Carbazole derivative and its application in electroluminescent device |
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