JP4536730B2 - アントラセン誘導体及びこれを発光物質として用いた有機発光素子 - Google Patents
アントラセン誘導体及びこれを発光物質として用いた有機発光素子 Download PDFInfo
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- JP4536730B2 JP4536730B2 JP2006541055A JP2006541055A JP4536730B2 JP 4536730 B2 JP4536730 B2 JP 4536730B2 JP 2006541055 A JP2006541055 A JP 2006541055A JP 2006541055 A JP2006541055 A JP 2006541055A JP 4536730 B2 JP4536730 B2 JP 4536730B2
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- 239000000463 material Substances 0.000 title claims description 13
- 150000001454 anthracenes Chemical class 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 9
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 55
- 239000010410 layer Substances 0.000 claims description 46
- 239000011368 organic material Substances 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 238000004519 manufacturing process Methods 0.000 description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
- 239000007858 starting material Substances 0.000 description 19
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000005684 electric field Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 8
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000005577 anthracene group Chemical group 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000032258 transport Effects 0.000 description 4
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 2
- VTSDGYDTWADUJQ-UHFFFAOYSA-N 2-bromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N CC(C)(CCN1c2c3C(C)(C)CC1)c2cc(C=C1c2nc4ccccc4[s]2)c3OC1=O Chemical compound CC(C)(CCN1c2c3C(C)(C)CC1)c2cc(C=C1c2nc4ccccc4[s]2)c3OC1=O MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- -1 aryl alcohol Chemical compound 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
- C07C13/58—Completely or partially hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
- H10K85/615—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
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
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- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
- Indole Compounds (AREA)
Description
本発明では、前記のような発光ゲスト物質であるドーパントをまず選択した後、選択されたドーパントとマッチングされるバンドギャップを持つ化合物を化学式1の化合物の中から選択して発光ホストとして使用することもできる。
実施例1
ITO (indium tin oxide) が1500Åの厚さに薄膜コートされたガラス基板を、洗剤を溶解させた蒸留水に入れて超音波で洗浄した。洗剤としては、Fischer Co.社の製品を使用し、蒸留水としては、Millipore Co.社製のフィルターで2回濾過された蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間行った。蒸留水洗浄が終了し、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄を行い、乾燥させた後、プラズマ洗浄機に移送させた。酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着器へ基板を移送させた。
発光層を、化学式4の化合物の代わりに、製造例6で製造した化学式9の化合物で形成した以外は、実施例1と同様にして有機発光素子を製造した。
発光層を、化学式4の化合物の代わりに、製造例7で製造した化学式10の化合物で形成した以外は、実施例1と同様にして有機発光素子を製造した。
発光層を、化学式4の化合物の代わりに、製造例8で製造した化学式12の化合物で形成した以外は、実施例1と同様にして有機発光素子を製造した。
発光層を、化学式4の化合物のみで形成する代わりに、製造例3で製造した化学式4の化合物に下記化学式15の化合物を100:2の割合でドーピングして300Åの厚さに製造した以外は、実施例1と同様にして有機発光素子を製造した。
発光層を形成する際、化学式4の化合物の代わりに、製造例6で製造した化学式9の化合物を使用した以外は、実施例5と同様にして有機発光素子を製造した。
発光層を形成する際、化学式4の化合物の代わりに、製造例7で製造した化学式10の化合物を使用した以外は、実施例5と同様にして有機発光素子を製造した。
発光層を形成する際、化学式4の化合物の代わりに、製造例8で製造した化学式12の化合物を使用した以外は、実施例5と同様にして有機発光素子を製造した。
発光層を、化学式4の化合物の代わりに、製造例9で製造した化学式14の化合物で形成した以外は、実施例1と同様にして有機発光素子を製造した。
Claims (6)
- 前記有機物層が、発光層を含み、この発光層が請求項1または2に記載の化合物を含むことを特徴とする、請求項3に記載の有機発光素子。
- 請求項1または2に記載の化合物を含む有機物層が、発光ゲスト物質をさらに含むことを特徴とする、請求項3に記載の有機発光素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20040070100 | 2004-09-02 | ||
PCT/KR2005/002896 WO2006025700A1 (en) | 2004-09-02 | 2005-09-01 | Anthracene derivatives and organic light emitting device using the same as a light emitting material |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007513886A JP2007513886A (ja) | 2007-05-31 |
JP4536730B2 true JP4536730B2 (ja) | 2010-09-01 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006541055A Active JP4536730B2 (ja) | 2004-09-02 | 2005-09-01 | アントラセン誘導体及びこれを発光物質として用いた有機発光素子 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20060046097A1 (ja) |
EP (1) | EP1786886B1 (ja) |
JP (1) | JP4536730B2 (ja) |
KR (1) | KR100749631B1 (ja) |
CN (1) | CN100519492C (ja) |
AT (1) | ATE499425T1 (ja) |
DE (1) | DE602005026533D1 (ja) |
TW (1) | TW200609332A (ja) |
WO (1) | WO2006025700A1 (ja) |
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DE102006013802A1 (de) * | 2006-03-24 | 2007-09-27 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
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DE112008001206B4 (de) | 2007-05-17 | 2019-01-31 | Lg Chem. Ltd. | Neue Anthrazen-Derivate und organische elektronische Vorrichtung, die diese verwendet |
US20080299294A1 (en) * | 2007-06-04 | 2008-12-04 | Feng Wen Yen | Anthracene compound and organic light emitting device using the same |
KR100910134B1 (ko) * | 2007-07-13 | 2009-08-03 | (주)그라쎌 | 유기 발광재료 및 이를 포함하는 유기발광소자 |
KR100935356B1 (ko) * | 2007-11-19 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 녹색 발광 화합물 및 이를 발광재료로서 채용하고 있는유기 전기 발광 소자 |
KR100940938B1 (ko) * | 2007-12-04 | 2010-02-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
EP2107062A1 (en) * | 2008-04-03 | 2009-10-07 | SOLVAY (Société Anonyme) | Naphthyl-substituted anthracene derivatives and their use in organic light-emitting diodes |
JP4662384B2 (ja) * | 2007-12-25 | 2011-03-30 | 財団法人山形県産業技術振興機構 | 有機エレクトロルミネッセンス材料およびそれを用いた素子 |
KR100974562B1 (ko) * | 2007-12-31 | 2010-08-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR100991416B1 (ko) * | 2007-12-31 | 2010-11-03 | 다우어드밴스드디스플레이머티리얼 유한회사 | 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
KR20090082778A (ko) | 2008-01-28 | 2009-07-31 | 삼성모바일디스플레이주식회사 | 유기전계발광소자 및 그 제조방법 |
KR101001384B1 (ko) * | 2008-02-29 | 2010-12-14 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
KR100901887B1 (ko) * | 2008-03-14 | 2009-06-09 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 발광소자 |
KR100989815B1 (ko) * | 2008-03-20 | 2010-10-29 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR100946411B1 (ko) * | 2008-03-28 | 2010-03-09 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR20090105495A (ko) * | 2008-04-02 | 2009-10-07 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전기 발광 소자 |
KR100910150B1 (ko) * | 2008-04-02 | 2009-08-03 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR101495547B1 (ko) * | 2008-04-17 | 2015-02-25 | 롬엔드하스전자재료코리아유한회사 | 신규한 전자 재료용 화합물 및 이를 포함하는 유기 전자소자 |
KR20090111915A (ko) * | 2008-04-23 | 2009-10-28 | (주)그라쎌 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
KR20100000772A (ko) * | 2008-06-25 | 2010-01-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 |
EP2145936A3 (en) * | 2008-07-14 | 2010-03-17 | Gracel Display Inc. | Fluorene and pyrene derivatives and organic electroluminescent device using the same |
WO2010013676A1 (ja) * | 2008-07-28 | 2010-02-04 | 出光興産株式会社 | 有機発光媒体及び有機el素子 |
KR20100041043A (ko) * | 2008-10-13 | 2010-04-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
WO2010085087A2 (ko) | 2009-01-20 | 2010-07-29 | 주식회사 엘지화학 | 신규한 시클로알켄 유도체 및 이를 이용한 유기전자소자 |
CN102633590A (zh) * | 2011-10-27 | 2012-08-15 | 吉林奥来德光电材料股份有限公司 | 一种不对称蒽衍生物及其制备方法 |
KR101975945B1 (ko) | 2016-08-17 | 2019-05-08 | 주식회사 엘지화학 | 안트라센계 화합물 및 이를 포함하는 유기 발광 소자 |
WO2019229591A1 (ja) | 2018-05-31 | 2019-12-05 | 株式会社半導体エネルギー研究所 | 有機化合物、発光素子、発光装置、電子機器、および照明装置 |
KR20200129988A (ko) * | 2019-05-10 | 2020-11-18 | 주식회사 엘지화학 | 유기 발광 소자 |
KR102444280B1 (ko) * | 2019-05-10 | 2022-09-15 | 주식회사 엘지화학 | 유기 발광 소자 |
KR20200129994A (ko) * | 2019-05-10 | 2020-11-18 | 주식회사 엘지화학 | 유기 발광 소자 |
JP2020188121A (ja) * | 2019-05-14 | 2020-11-19 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
JP2021103714A (ja) * | 2019-12-25 | 2021-07-15 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
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EP0681019B1 (en) * | 1994-04-26 | 1999-09-01 | TDK Corporation | Phenylanthracene derivative and organic EL element |
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JPH11249311A (ja) * | 1998-03-03 | 1999-09-17 | Jsr Corp | 反射防止膜形成用組成物 |
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US7053255B2 (en) * | 2000-11-08 | 2006-05-30 | Idemitsu Kosan Co., Ltd. | Substituted diphenylanthracene compounds for organic electroluminescence devices |
US6661023B2 (en) * | 2002-02-28 | 2003-12-09 | Eastman Kodak Company | Organic element for electroluminescent devices |
US20040018380A1 (en) * | 2002-07-26 | 2004-01-29 | Xerox Corporation | Display device with anthracene and triazine derivatives |
JP4025136B2 (ja) | 2002-07-31 | 2007-12-19 | 出光興産株式会社 | アントラセン誘導体、有機エレクトロルミネッセンス素子用発光材料及び有機エレクトロルミネッセンス素子 |
KR100924462B1 (ko) * | 2002-08-23 | 2009-11-03 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 및 안트라센 유도체 |
US20040126617A1 (en) * | 2002-12-31 | 2004-07-01 | Eastman Kodak Company | Efficient electroluminescent device |
US7262228B2 (en) * | 2003-11-21 | 2007-08-28 | Curators Of The University Of Missouri | Photoinitiator systems with anthracene-based electron donors for curing cationically polymerizable resins |
US7326371B2 (en) * | 2004-03-25 | 2008-02-05 | Eastman Kodak Company | Electroluminescent device with anthracene derivative host |
-
2005
- 2005-09-01 JP JP2006541055A patent/JP4536730B2/ja active Active
- 2005-09-01 EP EP05808769A patent/EP1786886B1/en active Active
- 2005-09-01 CN CNB2005800014183A patent/CN100519492C/zh active Active
- 2005-09-01 KR KR1020050081177A patent/KR100749631B1/ko active IP Right Grant
- 2005-09-01 AT AT05808769T patent/ATE499425T1/de not_active IP Right Cessation
- 2005-09-01 WO PCT/KR2005/002896 patent/WO2006025700A1/en active Application Filing
- 2005-09-01 DE DE602005026533T patent/DE602005026533D1/de active Active
- 2005-09-02 US US11/217,406 patent/US20060046097A1/en not_active Abandoned
- 2005-09-02 TW TW094130144A patent/TW200609332A/zh unknown
Also Published As
Publication number | Publication date |
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ATE499425T1 (de) | 2011-03-15 |
EP1786886A1 (en) | 2007-05-23 |
EP1786886B1 (en) | 2011-02-23 |
KR100749631B1 (ko) | 2007-08-14 |
WO2006025700A1 (en) | 2006-03-09 |
US20060046097A1 (en) | 2006-03-02 |
DE602005026533D1 (de) | 2011-04-07 |
KR20060050915A (ko) | 2006-05-19 |
CN1898355A (zh) | 2007-01-17 |
JP2007513886A (ja) | 2007-05-31 |
EP1786886A4 (en) | 2009-04-29 |
TW200609332A (en) | 2006-03-16 |
CN100519492C (zh) | 2009-07-29 |
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