JP5709389B2 - オキサジアゾール誘導体、発光素子、発光装置及び電子機器 - Google Patents
オキサジアゾール誘導体、発光素子、発光装置及び電子機器 Download PDFInfo
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- JP5709389B2 JP5709389B2 JP2010056929A JP2010056929A JP5709389B2 JP 5709389 B2 JP5709389 B2 JP 5709389B2 JP 2010056929 A JP2010056929 A JP 2010056929A JP 2010056929 A JP2010056929 A JP 2010056929A JP 5709389 B2 JP5709389 B2 JP 5709389B2
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- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
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- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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Description
本実施の形態では、本発明のオキサジアゾール誘導体の一態様について説明する。
アリーレン基に結合する置換基としては、炭素数1〜4のアルキル基が挙げられる。具体的には、メチル基、エチル基、プロピル基、又はブチル基等が挙げられる。また、アリール基またはアリーレン基が有する置換基は1つであっても複数であってもよい。
本発明のオキサジアゾール誘導体を用いた発光素子の一態様について図1を用いて以下に説明する。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について図11(A)(B)を用いて説明する。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図3を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。
本実施の形態では、本発明のオキサジアゾール誘導体を用いて作製された発光装置について説明する。
本実施の形態では、実施の形態4に示す発光装置をその一部に含む本発明の電子機器について説明する。本発明の電子機器は、実施の形態1に示したオキサジアゾール誘導体を含み、低消費電力な表示部を有する。
Claims (12)
- 一般式(1)で表されるオキサジアゾール誘導体を発光層のホスト材料として用いた発光素子。
(式中、Ar1は置換または無置換の環を形成する炭素数が6〜10のアリール基を表し、Aは置換または無置換のフェニレン基を表し、R11〜R15、R21〜R25はそれぞれ水素、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、置換または無置換の9H−カルバゾール−9−イル基を表す。また、Ar1の置換基としては炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を有していてもよく、Aの置換基としては炭素数1〜4のアルキル基を有していてもよく、R11〜R15、R21−R25における9H−カルバゾール−9−イル基の置換基としては、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を有していてもよい。また、αの炭素とβの炭素とは互いに結合してカルバゾール環を形成してもよい。) - 一般式(2)で表されるオキサジアゾール誘導体を発光層のホスト材料として用いた発光素子。
(式中、Aは置換または無置換のフェニレン基を表し、R11〜R15、R21〜R25はそれぞれ水素、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、置換または無置換の9H−カルバゾール−9−イル基を表し、R31〜R35はそれぞれ水素、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を表す。また、Aの置換基としては炭素数1〜4のアルキル基を有していてもよく、R11〜R15、R21〜R25における9H−カルバゾール−9−イル基の置換基としては、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を有していてもよい。また、αの炭素とβの炭素とは互いに結合してカルバゾール環を形成してもよい。) - 一般式(3)で表されるオキサジアゾール誘導体を発光層のホスト材料として用いた発光素子。
(式中、R11〜R15、R21〜R25はそれぞれ水素、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、置換または無置換の9H−カルバゾール−9−イル基を表し、R31〜R35はそれぞれ水素、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を表す。また、R11〜R15、R21〜R25における9H−カルバゾール−9−イル基の置換基としては、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を有してもよい。また、αの炭素とβの炭素とは互いに結合してカルバゾール環を形成してもよい。) - 一般式(4)で表されるオキサジアゾール誘導体を発光層のホスト材料として用いた発光素子。
(式中、R11〜R15、R21〜R25はそれぞれ水素、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基、置換または無置換の9H−カルバゾール−9−イル基を表す。R11〜R15、R21〜R25における9H−カルバゾール−9−イル基の置換基としては、炭素数1〜4のアルキル基、環を形成する炭素数が6〜10のアリール基を有してもよい。また、αの炭素とβの炭素とは互いに結合してカルバゾール環を形成してもよい。) - 一般式(5)で表されるオキサジアゾール誘導体を発光層のホスト材料として用いた発光素子。
(式中、R13、R23はそれぞれ水素、または無置換の9H−カルバゾール−9−イル基を表す。また、αの炭素とβの炭素とは互いに結合してカルバゾール環を形成してもよい。) - 請求項1乃至5のいずれか一項において、
前記発光層は、燐光を発光する発光物質を含む発光素子。 - 請求項1乃至6のいずれか一項に記載の発光素子と、前記発光素子を制御する手段とを備えた発光装置。
- 請求項7に記載の発光装置を表示部に備えた電子機器。
- 一般式(5)で表されるオキサジアゾール誘導体。
(式中、R13、R23はそれぞれ水素、または無置換の9H−カルバゾール−9−イル基を表す。また、αの炭素とβの炭素とは互いに結合してカルバゾール環を形成してもよい。) - 構造式(100)で表されるオキサジアゾール誘導体。
- 構造式(135)で表されるオキサジアゾール誘導体。
- 構造式(152)で表されるオキサジアゾール誘導体。
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EP3042461A1 (en) | 2013-09-02 | 2016-07-13 | Philips Lighting Holding B.V. | Transparent computer structure |
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