JP5111135B2 - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
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- JP5111135B2 JP5111135B2 JP2008023232A JP2008023232A JP5111135B2 JP 5111135 B2 JP5111135 B2 JP 5111135B2 JP 2008023232 A JP2008023232 A JP 2008023232A JP 2008023232 A JP2008023232 A JP 2008023232A JP 5111135 B2 JP5111135 B2 JP 5111135B2
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- 150000002894 organic compounds Chemical class 0.000 claims abstract description 96
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000005581 pyrene group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- -1 naphthalenediyl groups Chemical group 0.000 claims description 18
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
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- 150000001875 compounds Chemical class 0.000 abstract description 61
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- 230000000052 comparative effect Effects 0.000 description 11
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 10
- 0 C*C=CC=Cc1c(C)c(c(OC)ccc2)c2cc1 Chemical compound C*C=CC=Cc1c(C)c(c(OC)ccc2)c2cc1 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 125000006267 biphenyl group Chemical group 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 9
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 9
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- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 9
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 9
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
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- 150000004706 metal oxides Chemical class 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
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- 239000011241 protective layer Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
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- 238000004544 sputter deposition Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 239000010453 quartz Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- 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
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- 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
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- 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
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/62—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Description
(ii)好適なキャリア注入レベルを得ることが電子及びホールのいずれにおいても容易であること
また、第二の有機化合物は、第一の有機化合物と組み合わせて用いると、以下の特徴をも有することになる。
(iii)第二の有機化合物から第一の有機化合物へ良好にエネルギー移動を行うことができること
(iv)第二の有機化合物と第一の有機化合物との相溶性が高く、第一の有機化合物が層内で良好に分散すること
1.発光層内での電子・ホールの輸送。
2.ホストの励起子生成。
3.ホスト分子間の励起エネルギー伝達。
4.ホストからゲストへの励起エネルギー移動。
ガラス基板上に、陽極として酸化錫インジウム(ITO)をスパッタ法にて膜厚120nmで成膜した。これをアセトン、イソプロピルアルコール(IPA)で順次超音波洗浄し、次いでIPAで煮沸洗浄後乾燥した。さらに、UV/オゾン洗浄した。以上の処理を施したガラス基板を透明導電性支持基板として使用した。
実施例1において、発光層のゲストとして、例示化合物No.A−2の代わりに例示化合物No.A−11を用いる以外は、実施例1と同様の方法により素子を作製した。
実施例1において、発光層のゲストとして、例示化合物No.A−2の代わりに例示化合物No.B−20を用いる以外は、実施例1と同様の方法により素子を作製した。
実施例1において、発光層のゲストとして、例示化合物No.A−2の代わりに例示化合物No.B−1を用いる以外は、実施例1と同様の方法により素子を作製した。
実施例1と同様の手法で陽極及びホール輸送層を形成した。
実施例1と同様の手法で陽極及びホール輸送層を形成した。
実施例5において、発光層のゲストとして、例示化合物No.E−4の代わりに例示化合物No.E−48を用いる以外は、実施例5と同様の方法により素子を作製した。
実施例5において、発光層のゲストとして、例示化合物No.E−4の代わりに例示化合物No.C−11を用いる以外は、実施例5と同様の方法により素子を作製した。
実施例1と同様の手法で電極及びホール輸送層を形成した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに例示化合物HB−55を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに例示化合物HB−25を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに例示化合物HC−1を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに例示化合物HA−47を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに例示化合物HD−4を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに例示化合物HD−8を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに下記に示す比較化合物1を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに下記に示す比較化合物2を用いる以外は、実施例9と同様の方法により素子を作製した。
実施例9において、発光層のホストとして、例示化合物HA−3の代わりに下記に示す比較化合物3を用いる以外は、実施例9と同様の方法により素子を作製した。
透明基板としてのガラス基板上に薄膜トランジスタ(thin film transistor、以下、TFTという。)を形成した。このTFT上にポリイミドを成膜、露光、現像、焼成して平坦化膜を形成した。この平坦化膜の形成の段階でコンタクトホールも形成した。尚、本実施例の素子は、後工程で形成する電極がこのコンタクトホールを介してTFTに接続される形式になっている。
2 陽極
3 発光層
4 陰極
5 ホール輸送層
6 電子輸送層
7 ホール注入層
8 ホール/エキシトンブロッキング層
10,20,30,40,50,60 有機発光素子
Claims (7)
- 前記第二の有機化合物がピレン骨格及びフルオレン骨格を有する有機化合物であることを特徴とする、請求項1に記載の有機発光素子。
- 前記第二の有機化合物が下記一般式(III)で示されることを特徴とする、請求項1乃至3のいずれか一項に記載の有機発光素子。
- 前記第二の有機化合物が下記一般式(IV)で示されることを特徴とする、請求項1乃至3のいずれか一項に記載の有機発光素子。
- 前記第一の有機化合物及び前記第二の有機化合物が、炭素原子と水素原子とのみからなる有機化合物であることを特徴とする、請求項1乃至6のいずれか一項に記載の有機発光素子。
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JP2008023232A JP5111135B2 (ja) | 2007-03-09 | 2008-02-01 | 有機発光素子 |
EP08721643A EP2121547B1 (en) | 2007-03-09 | 2008-03-03 | Organic light-emitting device |
AT08721643T ATE495141T1 (de) | 2007-03-09 | 2008-03-03 | Organische lichtemittierende vorrichtung |
DE602008004457T DE602008004457D1 (de) | 2007-03-09 | 2008-03-03 | Organische lichtemittierende vorrichtung |
US12/296,074 US8084147B2 (en) | 2007-03-09 | 2008-03-03 | Organic light-emitting device |
KR1020097016697A KR101101037B1 (ko) | 2007-03-09 | 2008-03-03 | 유기 발광 소자 |
PCT/JP2008/054226 WO2008111543A1 (en) | 2007-03-09 | 2008-03-03 | Organic light-emitting device |
US13/298,623 US20120056172A1 (en) | 2007-03-09 | 2011-11-17 | Organic light-emitting device |
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JP2008023232A JP5111135B2 (ja) | 2007-03-09 | 2008-02-01 | 有機発光素子 |
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EP (1) | EP2121547B1 (ja) |
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JP2008255099A (ja) * | 2007-03-12 | 2008-10-23 | Canon Inc | ナフタレン化合物及びこれを用いた有機発光素子 |
JP2008255095A (ja) * | 2007-03-09 | 2008-10-23 | Canon Inc | 縮合環芳香族化合物及びこれを用いた有機発光素子 |
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JP5111135B2 (ja) * | 2007-03-09 | 2012-12-26 | キヤノン株式会社 | 有機発光素子 |
JP5618495B2 (ja) * | 2008-05-16 | 2014-11-05 | キヤノン株式会社 | 有機発光素子 |
JP5335284B2 (ja) * | 2008-05-22 | 2013-11-06 | キヤノン株式会社 | 縮合多環化合物およびそれを有する有機発光素子 |
JP5376857B2 (ja) * | 2008-08-04 | 2013-12-25 | キヤノン株式会社 | 縮合多環化合物及びこれを用いた有機発光素子 |
JP2010123917A (ja) * | 2008-10-22 | 2010-06-03 | Canon Inc | 有機発光素子 |
US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
US20120168733A1 (en) * | 2009-12-21 | 2012-07-05 | Idemitsu Kosan Co., Ltd. | Pyrene derivative and organic electroluminescent element using the same |
EP2518787A1 (en) * | 2009-12-21 | 2012-10-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element using pyrene derivative |
JP6470495B2 (ja) * | 2013-03-07 | 2019-02-13 | キヤノン株式会社 | 電子写真感光体、該電子写真感光体を有する電子写真装置およびプロセスカートリッジ |
US9997717B2 (en) | 2014-12-12 | 2018-06-12 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
US11094886B2 (en) * | 2019-09-13 | 2021-08-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element and electronic device |
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JP3824417B2 (ja) | 1997-04-04 | 2006-09-20 | 三井化学株式会社 | 炭化水素化合物および有機電界発光素子 |
JP3662104B2 (ja) | 1997-12-10 | 2005-06-22 | 三井化学株式会社 | 有機電界発光素子 |
JP4255610B2 (ja) * | 1999-12-28 | 2009-04-15 | 出光興産株式会社 | 白色系有機エレクトロルミネッセンス素子 |
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JP4330058B2 (ja) * | 2000-09-27 | 2009-09-09 | 三井化学株式会社 | 炭化水素化合物および有機電界発光素子 |
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JP4462753B2 (ja) | 2000-12-01 | 2010-05-12 | 三井化学株式会社 | 炭化水素化合物および有機電界発光素子 |
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JP2006140235A (ja) * | 2004-11-10 | 2006-06-01 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP4429149B2 (ja) | 2004-11-26 | 2010-03-10 | キヤノン株式会社 | フルオレン化合物及び有機発光素子 |
JP4659695B2 (ja) | 2005-11-01 | 2011-03-30 | キヤノン株式会社 | フルオレン化合物及び有機発光素子 |
US20090066227A1 (en) * | 2005-12-20 | 2009-03-12 | Canon Kabushiki Kaisha | Organic light-emitting device |
JP2007227152A (ja) * | 2006-02-23 | 2007-09-06 | Idemitsu Kosan Co Ltd | 白色系有機エレクトロルミネッセンス素子 |
JP4164514B2 (ja) | 2006-04-28 | 2008-10-15 | キヤノン株式会社 | 有機化合物および有機発光素子 |
JP5111135B2 (ja) * | 2007-03-09 | 2012-12-26 | キヤノン株式会社 | 有機発光素子 |
JP5241256B2 (ja) * | 2007-03-09 | 2013-07-17 | キヤノン株式会社 | 縮合環芳香族化合物及びこれを用いた有機発光素子 |
JP4827775B2 (ja) | 2007-03-13 | 2011-11-30 | キヤノン株式会社 | 電界発光素子 |
JP2008300753A (ja) * | 2007-06-04 | 2008-12-11 | Mitsui Chemicals Inc | 有機トランジスタ |
-
2008
- 2008-02-01 JP JP2008023232A patent/JP5111135B2/ja active Active
- 2008-03-03 AT AT08721643T patent/ATE495141T1/de not_active IP Right Cessation
- 2008-03-03 KR KR1020097016697A patent/KR101101037B1/ko not_active Expired - Fee Related
- 2008-03-03 WO PCT/JP2008/054226 patent/WO2008111543A1/en active Application Filing
- 2008-03-03 US US12/296,074 patent/US8084147B2/en active Active
- 2008-03-03 EP EP08721643A patent/EP2121547B1/en active Active
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2011
- 2011-11-17 US US13/298,623 patent/US20120056172A1/en not_active Abandoned
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008255095A (ja) * | 2007-03-09 | 2008-10-23 | Canon Inc | 縮合環芳香族化合物及びこれを用いた有機発光素子 |
JP2008255099A (ja) * | 2007-03-12 | 2008-10-23 | Canon Inc | ナフタレン化合物及びこれを用いた有機発光素子 |
Also Published As
Publication number | Publication date |
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KR20090126240A (ko) | 2009-12-08 |
WO2008111543A1 (en) | 2008-09-18 |
EP2121547A4 (en) | 2009-12-23 |
JP2008258580A (ja) | 2008-10-23 |
KR101101037B1 (ko) | 2011-12-29 |
ATE495141T1 (de) | 2011-01-15 |
EP2121547A1 (en) | 2009-11-25 |
US8084147B2 (en) | 2011-12-27 |
EP2121547B1 (en) | 2011-01-12 |
US20090278446A1 (en) | 2009-11-12 |
US20120056172A1 (en) | 2012-03-08 |
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