JP2009196977A5 - - Google Patents
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- Publication number
- JP2009196977A5 JP2009196977A5 JP2009004675A JP2009004675A JP2009196977A5 JP 2009196977 A5 JP2009196977 A5 JP 2009196977A5 JP 2009004675 A JP2009004675 A JP 2009004675A JP 2009004675 A JP2009004675 A JP 2009004675A JP 2009196977 A5 JP2009196977 A5 JP 2009196977A5
- Authority
- JP
- Japan
- Prior art keywords
- represented
- producing
- triarylpyrazine
- formula
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002994 raw material Substances 0.000 claims 16
- 238000004519 manufacturing process Methods 0.000 claims 12
- 239000003795 chemical substances by application Substances 0.000 claims 9
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- 238000006356 dehydrogenation reaction Methods 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009004675A JP5271721B2 (ja) | 2008-01-23 | 2009-01-13 | トリアリールピラジン誘導体の製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008012468 | 2008-01-23 | ||
| JP2008012468 | 2008-01-23 | ||
| JP2009004675A JP5271721B2 (ja) | 2008-01-23 | 2009-01-13 | トリアリールピラジン誘導体の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009196977A JP2009196977A (ja) | 2009-09-03 |
| JP2009196977A5 true JP2009196977A5 (enExample) | 2011-12-22 |
| JP5271721B2 JP5271721B2 (ja) | 2013-08-21 |
Family
ID=40875576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009004675A Expired - Fee Related JP5271721B2 (ja) | 2008-01-23 | 2009-01-13 | トリアリールピラジン誘導体の製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US7993494B2 (enExample) |
| JP (1) | JP5271721B2 (enExample) |
| KR (1) | KR101604237B1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8101755B2 (en) * | 2008-10-23 | 2012-01-24 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex including pyrazine derivative |
| JP5829828B2 (ja) | 2010-04-06 | 2015-12-09 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子及び発光装置 |
| US8664383B2 (en) | 2010-10-15 | 2014-03-04 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, and light-emitting element and display device using the organometallic complex |
| TWI529238B (zh) | 2011-04-15 | 2016-04-11 | 半導體能源研究所股份有限公司 | 有機發光元件、有機金屬錯合物發光裝置、電子用具及照明裝置 |
| JP2013147490A (ja) | 2011-12-23 | 2013-08-01 | Semiconductor Energy Lab Co Ltd | イリジウム錯体、発光素子、発光装置、電子機器、及び照明装置 |
| JP6166557B2 (ja) | 2012-04-20 | 2017-07-19 | 株式会社半導体エネルギー研究所 | 燐光性有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置 |
| JP6117618B2 (ja) | 2012-06-01 | 2017-04-19 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、及び照明装置 |
| US9196844B2 (en) | 2012-06-01 | 2015-11-24 | Semiconductor Energy Laboratory Co., Ltd. | Method of synthesizing pyrazine derivative, and light-emitting element, light-emitting device, electronic device, and lighting device |
| US9231217B2 (en) * | 2013-11-28 | 2016-01-05 | Semiconductor Energy Laboratory Co., Ltd. | Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device |
| JP6697299B2 (ja) | 2015-04-01 | 2020-05-20 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、および照明装置 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4303689A (en) * | 1965-04-30 | 1981-12-01 | Firmenich Sa | Flavoring with pyrazine derivatives |
| JPS5229750B2 (enExample) * | 1973-02-08 | 1977-08-03 | ||
| JPS5337675A (en) * | 1976-09-20 | 1978-04-06 | Tokai Electro Chemical Co | Production of pyrazines |
| JPH0674256B2 (ja) * | 1986-12-24 | 1994-09-21 | 広栄化学工業株式会社 | ピラジン類の製造方法 |
| JP4154139B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
| JP4460743B2 (ja) | 2000-09-29 | 2010-05-12 | 富士フイルム株式会社 | イリジウム錯体またはその互変異性体の製造方法 |
| KR100533556B1 (ko) * | 2000-11-30 | 2005-12-06 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
| DE10238903A1 (de) * | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
| DE10249926A1 (de) * | 2002-10-26 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
| US8084145B2 (en) * | 2004-04-02 | 2011-12-27 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light emitting element using the complex, light emitting device using the element, and electric apparatus using the device |
| WO2005115061A1 (en) | 2004-05-20 | 2005-12-01 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element and light emitting device |
| CN101163711B (zh) | 2005-03-17 | 2013-05-29 | 株式会社半导体能源研究所 | 有机金属络合物、以及使用所述有机金属络合物的发光元件、发光装置和发光电子-装置 |
| WO2007066556A1 (en) * | 2005-12-05 | 2007-06-14 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex and light-emitting element, light-emitting device and electronic device using the same |
| JP2007182429A (ja) * | 2005-12-05 | 2007-07-19 | Semiconductor Energy Lab Co Ltd | 有機金属錯体および前記錯体を用いた発光素子、発光装置、並びに電子機器 |
| JP5227510B2 (ja) * | 2005-12-28 | 2013-07-03 | 株式会社半導体エネルギー研究所 | ピラジン誘導体、及び前記ピラジン誘導体を用いた発光素子、表示装置、電子機器 |
| JP5244329B2 (ja) | 2006-03-21 | 2013-07-24 | 株式会社半導体エネルギー研究所 | 有機金属錯体及び発光材料 |
| TWI481616B (zh) * | 2006-03-21 | 2015-04-21 | Semiconductor Energy Lab | 有機金屬錯合物及使用該有機金屬錯合物之發光元件，發光裝置和電子裝置 |
-
2009
- 2009-01-13 JP JP2009004675A patent/JP5271721B2/ja not_active Expired - Fee Related
- 2009-01-15 US US12/354,403 patent/US7993494B2/en not_active Expired - Fee Related
- 2009-01-23 KR KR1020090006365A patent/KR101604237B1/ko not_active Expired - Fee Related
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