JP2004155755A5 - - Google Patents
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- Publication number
- JP2004155755A5 JP2004155755A5 JP2003101050A JP2003101050A JP2004155755A5 JP 2004155755 A5 JP2004155755 A5 JP 2004155755A5 JP 2003101050 A JP2003101050 A JP 2003101050A JP 2003101050 A JP2003101050 A JP 2003101050A JP 2004155755 A5 JP2004155755 A5 JP 2004155755A5
- Authority
- JP
- Japan
- Prior art keywords
- independently
- indene
- halogen
- dihydroindacene
- another
- 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
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- URFPRAHGGBYNPW-UHFFFAOYSA-N 1-bromo-4-ethylbenzene Chemical compound CCC1=CC=C(Br)C=C1 URFPRAHGGBYNPW-UHFFFAOYSA-N 0.000 description 2
- 0 CC1COC(*)OC1 Chemical compound CC1COC(*)OC1 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 1,4-cyclohexadienyl Chemical group 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KMGDYKOGDOVDCW-UHFFFAOYSA-N CC1CC=C(C)CC1 Chemical compound CC1CC=C(C)CC1 KMGDYKOGDOVDCW-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-UHFFFAOYSA-N 0.000 description 1
- INNBUVYAAZWGRE-UHFFFAOYSA-N CCCC(CC1)CCC1C(C(c1c2F)(F)F)=Cc1ccc2F Chemical compound CCCC(CC1)CCC1C(C(c1c2F)(F)F)=Cc1ccc2F INNBUVYAAZWGRE-UHFFFAOYSA-N 0.000 description 1
- MJLPJAABRVSMTO-UHFFFAOYSA-N CCCC(CC1)CCC1C(C1(F)F)=Cc(cc2B(O)O)c1c(F)c2F Chemical compound CCCC(CC1)CCC1C(C1(F)F)=Cc(cc2B(O)O)c1c(F)c2F MJLPJAABRVSMTO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- SHNJHLWLAGUBOV-UHFFFAOYSA-N sodium;oxido(oxo)borane;octahydrate Chemical compound O.O.O.O.O.O.O.O.[Na+].[O-]B=O SHNJHLWLAGUBOV-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10214938A DE10214938A1 (de) | 2002-04-04 | 2002-04-04 | Fluorierte Indene und 1,7-Dihydroindacene mit negativem delta epsilon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004155755A JP2004155755A (ja) | 2004-06-03 |
| JP2004155755A5 true JP2004155755A5 (cg-RX-API-DMAC7.html) | 2006-05-25 |
| JP4587644B2 JP4587644B2 (ja) | 2010-11-24 |
Family
ID=27816147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003101050A Expired - Fee Related JP4587644B2 (ja) | 2002-04-04 | 2003-04-04 | 負のΔεを有するフッ素化インデンおよびフッ素化１，７−ジヒドロインダセン |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7182885B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1350780A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4587644B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100937290B1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE10214938A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0116991D0 (en) * | 2001-07-12 | 2001-09-05 | Qinetiq Ltd | Novel compounds |
| DE10135499A1 (de) * | 2001-07-20 | 2003-01-30 | Merck Patent Gmbh | Indanverbindungen mit negativem Delta-epsilon |
| DE10341154B4 (de) * | 2003-09-06 | 2012-05-16 | Nematel Gmbh & Co. Kg | Tricyclische Fluorverbindungen, flüssigkristallines Medium sowie dessen Verwendung |
| EP1673418B1 (de) * | 2003-10-17 | 2015-08-12 | Merck Patent GmbH | Flüssigkristallines medium enthaltend fluorierte indanverbindung |
| EP1741000B1 (de) | 2004-04-26 | 2012-12-26 | Merck Patent GmbH | As-indacenderivate mit negativer dielektrischer anisotropie |
| KR100662192B1 (ko) | 2005-01-11 | 2006-12-27 | 주식회사 엘지화학 | 신규 인단 화합물을 포함하는 액정 조성물 및 이를 이용한액정 디스플레이 장치 |
| JP2006317656A (ja) * | 2005-05-12 | 2006-11-24 | Dainippon Printing Co Ltd | 異方性光学素子 |
| EP1904470B1 (de) * | 2005-07-20 | 2009-08-26 | Merck Patent GmbH | S-indacen- und indeno[5,6-d][1,3]dioxol-derivate und deren verwendung als komponente flüssigkristalliner mischungen |
| CN102659533B (zh) * | 2012-04-10 | 2015-05-13 | 江苏和成显示科技股份有限公司 | 作为液晶介质的组分的茚衍生物及其制备方法和应用 |
| CN103351275B (zh) * | 2013-07-01 | 2015-06-10 | 江苏和成显示科技股份有限公司 | 包含多氟代茚满的液晶化合物及其组合物和应用 |
| CN103361074B (zh) * | 2013-07-01 | 2015-08-26 | 江苏和成新材料有限公司 | 包含多氟代不饱和茚环的液晶化合物及其组合物和应用 |
| CN106675575B (zh) * | 2015-11-06 | 2018-12-18 | 江苏和成显示科技有限公司 | 一种介电负性液晶化合物及其制备方法与应用 |
| CN108690640B (zh) * | 2018-07-17 | 2022-02-25 | 烟台显华化工科技有限公司 | 一种含茚环的化合物及液晶介质 |
| CN115925663A (zh) * | 2022-12-05 | 2023-04-07 | Tcl华星光电技术有限公司 | 有机化合物、液晶组合物以及液晶显示面板 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3828795A (en) * | 1973-06-21 | 1974-08-13 | Reynolds Tobacco Co R | Tobacco product |
| JPS57193338A (en) * | 1981-05-25 | 1982-11-27 | Sekisui Jushi Co Ltd | Manufacture of synthetic resin shipping band by vacuum extrusion method |
| DE4002609A1 (de) * | 1989-09-07 | 1991-03-21 | Merck Patent Gmbh | Difluorbenzonitrile und fluessigkristallines medium |
| EP0582195B1 (de) * | 1992-08-03 | 2000-12-20 | TARGOR GmbH | Verfahren zur Herstellung eines Olefinpolymers unter Verwendung spezieller Metallocene |
| JP3417969B2 (ja) * | 1993-02-09 | 2003-06-16 | 旭硝子株式会社 | 含フッ素インデン環誘導体化合物およびそれを含有する液晶組成物 |
| JP3430548B2 (ja) * | 1993-03-10 | 2003-07-28 | 旭硝子株式会社 | 含フッ素インダン環誘導体化合物およびそれを含有する液晶組成物 |
| US5789634A (en) * | 1997-02-05 | 1998-08-04 | Boulder Scientific Company | Coupling reactions of 2-substituted, 7-haloindenes with aryl substituents to produce metallocene catalyst intermediates |
| JP4048570B2 (ja) * | 1997-02-25 | 2008-02-20 | チッソ株式会社 | 誘電率異方性値が負の液晶性化合物、この液晶性化合物を含有する液晶組成物、及びこの液晶組成物を用いた液晶表示素子 |
| CN1762957B (zh) * | 1997-03-07 | 2010-05-12 | 巴塞尔聚烯烃股份有限公司 | 2,3-二氢-1-茚酮类化合物以及其制备方法 |
| DE19720289A1 (de) * | 1997-05-15 | 1998-11-19 | Hoechst Ag | Fluorierte 9H-Fluoren-Derivate und ihre Verwendung in flüssigkristallinen Mischungen |
| EP1027403B1 (en) * | 1997-10-10 | 2003-05-28 | Aventis Research & Technologies GmbH & Co. KG | 5-arylindane derivatives and ferroelectric liquid crystal mixture containing same |
| JP4655319B2 (ja) * | 1999-12-14 | 2011-03-23 | Ｄｉｃ株式会社 | 液晶媒体及び該液晶媒体を含有する液晶表示素子 |
| AU2002213922A1 (en) * | 2000-12-06 | 2002-06-18 | Merck Patent G.M.B.H | Liquid crystalline medium |
| DE10115955B4 (de) * | 2001-03-30 | 2017-10-19 | Merck Patent Gmbh | Fluorierte Fluoren-Derivate |
| DE10135499A1 (de) * | 2001-07-20 | 2003-01-30 | Merck Patent Gmbh | Indanverbindungen mit negativem Delta-epsilon |
-
2002
- 2002-04-04 DE DE10214938A patent/DE10214938A1/de not_active Withdrawn
-
2003
- 2003-03-07 EP EP03004926A patent/EP1350780A1/de not_active Withdrawn
- 2003-04-03 KR KR1020030020979A patent/KR100937290B1/ko not_active Expired - Fee Related
- 2003-04-04 US US10/406,569 patent/US7182885B2/en not_active Expired - Fee Related
- 2003-04-04 JP JP2003101050A patent/JP4587644B2/ja not_active Expired - Fee Related
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