WO2005087780A1 - 含カルコゲン縮環多環式有機材料及びその製造方法 - Google Patents
含カルコゲン縮環多環式有機材料及びその製造方法 Download PDFInfo
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- WO2005087780A1 WO2005087780A1 PCT/JP2005/004006 JP2005004006W WO2005087780A1 WO 2005087780 A1 WO2005087780 A1 WO 2005087780A1 JP 2005004006 W JP2005004006 W JP 2005004006W WO 2005087780 A1 WO2005087780 A1 WO 2005087780A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains three hetero rings
- C07D517/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains four or more hetero rings
-
- 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
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- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Definitions
- the present invention relates to a chalcogen-fused polycyclic organic material having high efficiency charge transport properties applicable to organic thin film transistors and organic electroluminescence (hereinafter, abbreviated as EL), and a method for producing the same. It is about.
- heteroacenes into which a hetero atom has been introduced and condensed polycyclic aromatic compounds having a similar dichalcogenide bond can also be expected as promising materials.
- Non-Patent Document 3 (Non-Patent Document 3)
- Non-Patent Document 4 K. Kobayashi, Phosphorus, Sulfur, and Silicon and the Related Elements, 1989, 43, ppl87.
- Non-Patent Document 5 (Non-Patent Document 5)
- Non-Patent Document 6 (Non-Patent Document 6)
- Non-Patent Document 7 (Non-Patent Document 7)
- Non-Patent Document 8 (Non-Patent Document 8)
- Non-Patent Document 9 (Non-Patent Document 9)
- the present invention has been made in view of the above-mentioned problems, and the present inventors have now conceptually developed a new synthetic method, and have developed a series of chalcogen-containing fused rings which are an important group of compounds.
- the purpose of the present invention is to provide a group of the above compounds and a method for producing the same by successfully developing an efficient general synthesis method for polycyclic organic materials.
- the chalcogen-containing fused polycyclic organic material according to the present invention has the following formula (1)
- E 1 represents S or Se
- Ar represents benzene, substituted benzene, naphthalene, substituted naphthalene, anthracene, substituted anthracene, thiophene, substituted thiophene, furan, substituted furan, pyrrole, substituted pyrrole, selenophene, A group fused via one double bond of substituted selenophene, pyridine, substituted pyridine, thiazole, substituted thiazole, benzothiophene, substituted benzothiophene, benzofuran, substituted benzofuran, indole or substituted doldol.
- the method for producing a chalcogen-containing fused polycyclic organic material according to the present invention has the following formula (5) for solving the above problem.
- Diacetylenes (wherein X represents I, Br or C1) are subjected to intramolecular tricyclization. This is characterized in that the above-mentioned chalcogen-containing fused polycyclic organic material is obtained.
- Another chalcogen-containing fused polycyclic organic material according to the present invention has the following formula (9)
- E 1 represents S or Se
- Ar represents benzene, substituted benzene, naphthalene, substituted naphthalene, anthracene, substituted anthracene, thiphenylphen, substituted thiphenylphen, furan, substituted fran, pyrrole, substituted Ring fusion through one double bond of pyrrole, selenophene, substituted selenophene, pyridine, substituted pyridin, thiazole, substituted thiazole, benzothiophene, substituted benzothiophene, benzofuran, substituted benzofuran, indole or substituted doldol
- the chalcogen-containing fused polycyclic organic material according to the present invention has the structure represented by the formula (1) or the formula (9), and is therefore expected to exhibit excellent charge transport properties.
- the present invention is advantageous in that it is suitable for use in organic electronic devices such as organic thin film transistors (TFT) and organic electroluminescent (EL) devices.
- the method for producing a chalcogen-containing fused polycyclic organic material according to the present invention provides a chalcogen-containing fused ring that is assumed to exhibit excellent charge transport properties by an intramolecular tricyclization reaction. Because polycyclic organic materials can be obtained, the production of chalcogen-containing fused polycyclic organic materials suitable for the field of organic electronics such as organic thin film transistors (TFT) and organic electroluminescent (EL) devices can be simplified and generalized. And!
- the first embodiment of the present invention is described as follows. Hereinafter, a method for synthesizing the compound represented by Formula (1) will be described. First, as shown in the following reaction formula (8) To, after Jimetarui spoon by Harogenme barrel exchange reaction using an organometallic base diacetylene compound represented by the formula (7) as a starting material, by reaction with chalcogen alone E 1, compounds of formula (1) ( Chalcogen-containing fused polycyclic organic materials) can be synthesized by an intramolecular tricyclization reaction.
- an organic lithium reagent such as n-BuLi, s-BuLi, and t-BuLi and an organic magnesium reagent such as an alkyl Grignard reagent can be used.
- an organic lithium reagent such as n-BuLi, s-BuLi, and t-BuLi and an organic magnesium reagent such as an alkyl Grignard reagent.
- the best yield is obtained when performing metal immersion in THF using t-BuLi.
- Rukogen single E 1 other high chalcogen alone reactive, such as S, chalcogen alone
- the end can be used.
- chalcogen alone E 1 above to di-acetylenes of 1 molar amount, 2 mol Ryo ⁇ optimum 10 molar amount, it is desirable to preferably use 4 mol to 6 mol amount.
- diacetylenes having at least two halogenated cyclic conjugate groups are preferable.
- the 2-position of the above-mentioned cyclic dani-drug group is desirable.
- the cyclic compound group is not particularly limited, but includes a phenyl group corresponding to benzene and a group derived from thiophene, and may further have a substituent.
- the reaction mixture was concentrated under reduced pressure. A 10% aqueous solution of sodium hydroxide was added to the obtained mixture, and dichloromethane was further extracted by shaking and extraction. Subsequently, the organic layer and the aqueous layer of dichloromethane were separated, and an aqueous solution of potassium ferricyanide was added to the separated aqueous layer, and a red solid precipitated in the aqueous layer was extracted with dichloromethane.
- Compound 7 C H S Se Si; purple plates (recrystallized from black form-ethanol).
- the heteroacene compound (condensed chalcogen-containing polycyclic organic material) according to the second embodiment of the present invention is described below.
- a method for synthesizing the compound represented by the formula (9) will be described.
- a compound represented by the above formula (1) is used as a starting material, and as shown in the following reaction formula (13), a dechalcogenization reaction described in each of Non-patent Documents 5 and 9 is performed to obtain a compound of the formula (9 ) Can be synthesized as a heterocene compound.
- a compound represented by the formula (1) is converted to a copper powder, a platinum complex (Pt (COD)
- the chalcogen-containing fused polycyclic organic material of the present invention is a novel compound that can be used as a charge transport material.
- the chalcogen-containing fused polycyclic organic material according to the present invention has the following formula (1)
- E 1 represents S or Se
- Ar represents benzene, substituted benzene, naphthalene, substituted naphthalene, anthracene, substituted anthracene, thiophene, substituted thiophene, furan, substituted furan, pyrrole, substituted pyrrole, selenophene, A group fused via one double bond of substituted selenophene, pyridine, substituted pyridine, thiazole, substituted thiazole, benzothiophene, substituted benzothiophene, benzofuran, substituted benzofuran, indole or substituted doldol.
- the above chalcogen-containing fused polycyclic organic material has the following formula (2) [0055] [Formula 13]
- R 2 , R 3 , and R 4 are each independently an aryl group (aryH, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a monovalent heterocyclic group, a monovalent substituted heterocyclic group, Elementary ring group, monovalent substituted oligoheterocyclic group, hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, alkyl group , Substituted alkenyl, alkyl, substituted alkyl, aryl (ally), amino, substituted amino, azo, carboxyl, acyl, alkoxycarbol, formyl, nitro Group, cyano group, silyl group, substituted silyl group, stanyl group, substituted stanyl group, boryl group, substituted boryl group,
- the chalcogen-containing fused polycyclic organic material is represented by the following formula (3)
- RR 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R. independently represent an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a monovalent heterocyclic group, Monovalent substituted heterocyclic group, monovalent oligoheterocyclic group, monovalent substituted oligoheterocyclic group, hydrogen atom, alkyl group, alkoxy Si, alkylthio, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, aryl, substituted alkyl, alkyl, substituted alkynyl, aryl, Amino group, substituted amino group, azo group, carboxyl group, acyl group, alkoxycarbol group, formyl group, nitro group, cyano group, silyl group, substituted silyl group, stanyl group, substitute
- the chalcogen-containing fused polycyclic organic material is represented by the following formula (4)
- RR 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 independently represent an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a monovalent heterocyclic group, Monovalent substituted heterocyclic group, monovalent oligoheterocyclic group, monovalent substituted oligoheterocyclic group, hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylalkyl group, arylalkyl group Arylalkoxy, arylalkylthio, alkyl, substituted alkenyl, alkyl, substituted alkynyl, aryl, amino, substituted amino, azo, carboxyl, acyl, Alkoxycarbonyl, formyl, nitro, cyano, silyl, substituted silyl, stanyl, substituted
- the above-mentioned chalcogen-containing fused polycyclic organic material is obtained by performing an intramolecular tricyclization reaction on diacetylenes (wherein X represents I, Br or C1).
- Another chalcogen-containing fused polycyclic organic material according to the present invention has the following formula (9)
- E 1 represents S or Se
- Ar represents benzene, substituted benzene, naphthalene, substituted naphthalene, anthracene, substituted anthracene, thiphenylphen, substituted thiphenylphen, furan, substituted phenyl.
- R 3 and R 4 independently represent an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a monovalent heterocyclic group, a monovalent substituted heterocyclic group, a monovalent oligoheterocyclic group, Substituted oligoheterocyclic group, hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, arylalkyl group, substituted alkyl group , An alkyl group, a substituted alkyl group, an aryl group, an amino group, a substituted amino group, an azo group, a carboxyl group, an acyl group, an alkoxycarbol group, a formyl group, a nitro group, a cyano group, and a silyl group ,
- R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a monovalent heterocyclic group, a monovalent substituted complex Ring group, monovalent oligoheterocyclic group, monovalent substituted oligoheterocyclic group, hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkoxy group Reelalkylthio, alkyl, substituted alkenyl, alkyl, substituted alkynyl, aryl, amino, substituted amino, azo, carboxy, carboxyl, acyl, alkoxycarbyl , Formyl, nitro, cyano, silyl, substituted silyl, stany
- RR 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 independently represent an aryl group, a substituted aryl group, an oligoaryl group, a substituted oligoaryl group, a monovalent heterocyclic group, 1 Divalent substituted heterocyclic group, 1 Trivalent oligoheterocyclic group, monovalent substituted oligoheterocyclic group, hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthio group, Alkenyl group, substituted alkenyl group, alkyl group, substituted alkynyl group, aryl group, amino group, substituted amino group, azo group, carboxyl group, acyl group, alkoxycarbyl group, formyl group, Nitro, cyano, silyl, substituted sily
- the chalcogen-containing fused polycyclic organic material according to the present invention can exhibit excellent charge transport properties, and thus can be used as an electronic device such as an organic thin film transistor or an organic EL device such as a display device that can be made thin and lightweight. It can be applied to applications.
- the method for producing a condensed chalcogen-containing polycyclic organic material according to the present invention can easily and surely obtain various condensed chalcogen-containing condensed polycyclic organic materials capable of exhibiting excellent charge transport properties. Can be.
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2005800063071A CN1997650B (zh) | 2004-03-10 | 2005-03-08 | 含硫属元素稠合多环型有机材料及其制备方法 |
JP2006510944A JP4673843B2 (ja) | 2004-03-10 | 2005-03-08 | 含カルコゲン縮環多環式有機材料及びその製造方法 |
EP05720278.0A EP1724272B1 (en) | 2004-03-10 | 2005-03-08 | Chalcogen-containing fused-ring polycyclic organic material and process for producing the same |
US10/592,056 US8044218B2 (en) | 2004-03-10 | 2005-03-08 | Chalcogen-containing fused polycyclic organic material and method for producing same |
CA2558727A CA2558727C (en) | 2004-03-10 | 2005-03-08 | Chalcogen-containing fused polycyclic organic material and method for prroducing same |
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JP2004068039 | 2004-03-10 | ||
JP2004-068039 | 2004-03-10 |
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WO2005087780A1 true WO2005087780A1 (ja) | 2005-09-22 |
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PCT/JP2005/004006 WO2005087780A1 (ja) | 2004-03-10 | 2005-03-08 | 含カルコゲン縮環多環式有機材料及びその製造方法 |
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US (1) | US8044218B2 (ja) |
EP (1) | EP1724272B1 (ja) |
JP (1) | JP4673843B2 (ja) |
KR (1) | KR100835427B1 (ja) |
CN (1) | CN1997650B (ja) |
CA (1) | CA2558727C (ja) |
TW (1) | TWI393724B (ja) |
WO (1) | WO2005087780A1 (ja) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009101982A1 (ja) * | 2008-02-13 | 2009-08-20 | Osaka University | 縮合環化合物及びその製造方法、重合体、これらを含む有機薄膜、並びに、これを備える有機薄膜素子及び有機薄膜トランジスタ |
JP2010045281A (ja) * | 2008-08-18 | 2010-02-25 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2011004869A1 (ja) | 2009-07-10 | 2011-01-13 | 住友化学株式会社 | 置換ベンゾカルコゲノアセン化合物、該化合物を含有する薄膜及び該薄膜を含有する有機半導体デバイス |
WO2012008483A1 (ja) * | 2010-07-13 | 2012-01-19 | 住友化学株式会社 | 有機半導体組成物、有機薄膜及びこれを備える有機薄膜トランジスタ |
WO2012046818A1 (ja) * | 2010-10-07 | 2012-04-12 | 住友化学株式会社 | 含カルコゲン縮合多環式化合物の製造方法 |
WO2012096360A1 (ja) * | 2011-01-11 | 2012-07-19 | 住友化学株式会社 | 置換ベンゾカルコゲノアセン化合物 |
US10135006B2 (en) | 2016-01-04 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101314998B1 (ko) * | 2006-12-13 | 2013-10-04 | 삼성전자주식회사 | 헤테로아센 화합물, 이를 포함하는 유기 박막 및 당해 박막을 포함하는 전자 소자 |
WO2009123695A1 (en) * | 2008-03-31 | 2009-10-08 | Corning Incorporated | Fused thiophenes and methods for making and using same |
US8350256B2 (en) * | 2010-07-19 | 2013-01-08 | Industrial Technology Research Institute | Organic semiconductor compounds |
GB201021277D0 (en) * | 2010-12-15 | 2011-01-26 | Cambridge Display Tech Ltd | Semiconductor blend |
JP5958988B2 (ja) * | 2012-03-16 | 2016-08-02 | Jnc株式会社 | 有機半導体薄膜、有機半導体素子および有機電界効果トランジスタ |
CN103483364A (zh) * | 2013-09-03 | 2014-01-01 | 太仓碧奇新材料研发有限公司 | 一种双苯并噻吩硼烷发光材料及其制备方法 |
DE102013110693B4 (de) * | 2013-09-27 | 2024-04-25 | Heliatek Gmbh | Photoaktives, organisches Material für optoelektronische Bauelemente |
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JP2001261794A (ja) | 2000-03-13 | 2001-09-26 | Japan Science & Technology Corp | ポリチオフェンラダー化合物とその製造法 |
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- 2005-03-08 CA CA2558727A patent/CA2558727C/en not_active Expired - Fee Related
- 2005-03-08 CN CN2005800063071A patent/CN1997650B/zh not_active Expired - Fee Related
- 2005-03-08 JP JP2006510944A patent/JP4673843B2/ja not_active Expired - Fee Related
- 2005-03-08 EP EP05720278.0A patent/EP1724272B1/en not_active Expired - Fee Related
- 2005-03-08 KR KR1020067021054A patent/KR100835427B1/ko active IP Right Grant
- 2005-03-08 US US10/592,056 patent/US8044218B2/en not_active Expired - Fee Related
- 2005-03-08 TW TW094107040A patent/TWI393724B/zh not_active IP Right Cessation
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JP2001261794A (ja) | 2000-03-13 | 2001-09-26 | Japan Science & Technology Corp | ポリチオフェンラダー化合物とその製造法 |
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Cited By (12)
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US8344095B2 (en) | 2008-02-13 | 2013-01-01 | Osaka University | Fused ring compound, method for producing the same, polymer, organic thin film containing the compound and/or polymer, and organic thin film device and organic thin film transistor each comprising the organic thin film |
JP2010045281A (ja) * | 2008-08-18 | 2010-02-25 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2011004869A1 (ja) | 2009-07-10 | 2011-01-13 | 住友化学株式会社 | 置換ベンゾカルコゲノアセン化合物、該化合物を含有する薄膜及び該薄膜を含有する有機半導体デバイス |
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US9178165B2 (en) | 2010-07-13 | 2015-11-03 | Sumitomo Chemical Company, Limited | Organic semiconductor composition, organic thin film, and organic thin film transistor having same |
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JP2012097065A (ja) * | 2010-10-07 | 2012-05-24 | Sumitomo Chemical Co Ltd | 含カルコゲン縮合多環式化合物の製造方法 |
WO2012096360A1 (ja) * | 2011-01-11 | 2012-07-19 | 住友化学株式会社 | 置換ベンゾカルコゲノアセン化合物 |
US10135006B2 (en) | 2016-01-04 | 2018-11-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
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CN1997650B (zh) | 2013-08-14 |
EP1724272A1 (en) | 2006-11-22 |
CA2558727C (en) | 2010-01-26 |
US8044218B2 (en) | 2011-10-25 |
CA2558727A1 (en) | 2005-09-22 |
KR100835427B1 (ko) | 2008-06-09 |
CN1997650A (zh) | 2007-07-11 |
US20070117973A1 (en) | 2007-05-24 |
JP4673843B2 (ja) | 2011-04-20 |
EP1724272A4 (en) | 2009-11-25 |
EP1724272B1 (en) | 2013-08-21 |
JPWO2005087780A1 (ja) | 2008-01-24 |
KR20060117379A (ko) | 2006-11-16 |
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