DD206785A5 - Fluessigkristallines dielektrikum - Google Patents

Fluessigkristallines dielektrikum Download PDF

Info

Publication number: DD206785A5
Authority: DD; German Democratic Republic
Prior art keywords: dihydroxy; naphthoquinone; bis; formula; alkoxy
Prior art date: 1982-01-28

Application number

DD83247475A

Other languages

German (de)

English (en)

Inventor

Guenther Haas

Georg Weber

Original Assignee

Merck Patent Gmbh

Priority date (The priority date 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 date listed.)

1982-01-28

Filing date

1983-01-26

Publication date

1984-02-08

1983-01-26 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1984-02-08 Publication of DD206785A5 publication Critical patent/DD206785A5/de

Links

239000007788 liquid Substances 0.000 title abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
125000000956 methoxy group Chemical class [H]C([H])([H])O* 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
239000000975 dye Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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 claims 1
239000004973 liquid crystal related substance Substances 0.000 claims 1
-1 ETHOXY Chemical class 0.000 abstract description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
AIESRBVWAFETPR-UHFFFAOYSA-N cyclohexa-1,2,4,5-tetraene Chemical class C1=C=CC=C=C1 AIESRBVWAFETPR-UHFFFAOYSA-N 0.000 abstract 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 48
229930192627 Naphthoquinone Natural products 0.000 description 22
150000002791 naphthoquinones Chemical class 0.000 description 22
150000001875 compounds Chemical class 0.000 description 16
RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000003989 dielectric material Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 8
239000000126 substance Substances 0.000 description 7
239000000470 constituent Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
QZLWMAFSJFJSAL-UHFFFAOYSA-N 2-(4-heptylphenyl)sulfanyl-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCCCCC)=CC=C1SC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O QZLWMAFSJFJSAL-UHFFFAOYSA-N 0.000 description 2
YYAVXASAKUOZJJ-UHFFFAOYSA-N 4-(4-butylcyclohexyl)benzonitrile Chemical compound C1CC(CCCC)CCC1C1=CC=C(C#N)C=C1 YYAVXASAKUOZJJ-UHFFFAOYSA-N 0.000 description 2
FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 2
WNOPRQOMOUTZIA-UHFFFAOYSA-N 4-(4-pentylphenyl)-1-phenylcyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CCC(C=2C=CC=CC=2)(C#N)C=C1 WNOPRQOMOUTZIA-UHFFFAOYSA-N 0.000 description 2
XXUSEPRYHRDKFV-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-UHFFFAOYSA-N 0.000 description 2
239000005210 4-(trans-4-Butylcyclohexyl)benzonitrile Substances 0.000 description 2
239000005254 4-(trans-4-Propylcyclohexyl)benzonitrile Substances 0.000 description 2
KXEOSLJLHAARJQ-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-propylphenyl)sulfanylnaphthalene-1,4-dione Chemical compound C1=CC(CCC)=CC=C1SC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O KXEOSLJLHAARJQ-UHFFFAOYSA-N 0.000 description 2
QGSLPPDLVXHHEL-UHFFFAOYSA-N 5,8-dihydroxy-2-phenylsulfanylnaphthalene-1,4-dione Chemical compound C=1C(=O)C=2C(O)=CC=C(O)C=2C(=O)C=1SC1=CC=CC=C1 QGSLPPDLVXHHEL-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
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 2
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000001044 red dye Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
QQFSIGWYINAJOB-UHFFFAOYSA-N 1,4-dicyclohexylbenzene Chemical class C1CCCCC1C1=CC=C(C2CCCCC2)C=C1 QQFSIGWYINAJOB-UHFFFAOYSA-N 0.000 description 1
RAYZALBEMJMGEA-UHFFFAOYSA-N 1-cyclohexylnaphthalene Chemical class C1CCCCC1C1=CC=CC2=CC=CC=C12 RAYZALBEMJMGEA-UHFFFAOYSA-N 0.000 description 1
YGFBBXYYCLHOOW-UHFFFAOYSA-N 2,3-diaminonaphthalene-1,4-dione Chemical class C1=CC=C2C(=O)C(N)=C(N)C(=O)C2=C1 YGFBBXYYCLHOOW-UHFFFAOYSA-N 0.000 description 1
SRBLYLWFYOHPRT-UHFFFAOYSA-N 2,6-bis[(4-heptylphenyl)sulfanyl]-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCCCCC)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(CCCCCCC)=CC=3)=CC(O)=C2C1=O SRBLYLWFYOHPRT-UHFFFAOYSA-N 0.000 description 1
HZTGJICBSHSHNY-UHFFFAOYSA-N 2,6-bis[(4-hexylphenyl)sulfanyl]-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCCCC)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(CCCCCC)=CC=3)=CC(O)=C2C1=O HZTGJICBSHSHNY-UHFFFAOYSA-N 0.000 description 1
UGSHPWQDYXUZGC-UHFFFAOYSA-N 2,6-dianilino-5,8-dihydroxynaphthalene-1,4-dione Chemical compound OC=1C=2C(=O)C=C(NC=3C=CC=CC=3)C(=O)C=2C(O)=CC=1NC1=CC=CC=C1 UGSHPWQDYXUZGC-UHFFFAOYSA-N 0.000 description 1
PFJYKSQEQHENEB-UHFFFAOYSA-N 2-(4-butylanilino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O PFJYKSQEQHENEB-UHFFFAOYSA-N 0.000 description 1
ZOYIOGJHCCHECA-UHFFFAOYSA-N 2-(4-butylphenyl)sulfanyl-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCC)=CC=C1SC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O ZOYIOGJHCCHECA-UHFFFAOYSA-N 0.000 description 1
YSANFYIWQDNUTI-UHFFFAOYSA-N 2-(4-ethoxyanilino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(OCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O YSANFYIWQDNUTI-UHFFFAOYSA-N 0.000 description 1
WQCNFQAHHKUNTB-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(OCC)=CC=C1C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O WQCNFQAHHKUNTB-UHFFFAOYSA-N 0.000 description 1
ODXIKLWQHICCRI-UHFFFAOYSA-N 2-(4-ethylanilino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O ODXIKLWQHICCRI-UHFFFAOYSA-N 0.000 description 1
OPTLYVZYPOKDMM-UHFFFAOYSA-N 2-(4-ethylphenyl)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CC)=CC=C1C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O OPTLYVZYPOKDMM-UHFFFAOYSA-N 0.000 description 1
VTPXIFGIOJRHFG-UHFFFAOYSA-N 2-(4-ethylphenyl)sulfanyl-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CC)=CC=C1SC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O VTPXIFGIOJRHFG-UHFFFAOYSA-N 0.000 description 1
JIXQJWDJLXRQSC-UHFFFAOYSA-N 2-(4-heptylanilino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCCCCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O JIXQJWDJLXRQSC-UHFFFAOYSA-N 0.000 description 1
AKNQPVCAIOSCEW-UHFFFAOYSA-N 2-(4-hexylanilino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCCCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O AKNQPVCAIOSCEW-UHFFFAOYSA-N 0.000 description 1
PPKNTJRWGITQQU-UHFFFAOYSA-N 2-(4-hexylphenyl)sulfanyl-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(CCCCCC)=CC=C1SC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O PPKNTJRWGITQQU-UHFFFAOYSA-N 0.000 description 1
SMHSPYVJAUGNOI-UHFFFAOYSA-N 2-cyclohexyl-1,4-dioxane Chemical class C1CCCCC1C1OCCOC1 SMHSPYVJAUGNOI-UHFFFAOYSA-N 0.000 description 1
YJDDXMSIMBMMGY-UHFFFAOYSA-N 2-cyclohexylpyrimidine Chemical class C1CCCCC1C1=NC=CC=N1 YJDDXMSIMBMMGY-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
SXGNMFOYISNDTI-UHFFFAOYSA-N 4,8-diamino-2,6-diphenylnaphthalene-1,5-dione Chemical compound C=1C(N)=C2C(=O)C(C=3C=CC=CC=3)=CC(N)=C2C(=O)C=1C1=CC=CC=C1 SXGNMFOYISNDTI-UHFFFAOYSA-N 0.000 description 1
MHXFYTISBVJROM-UHFFFAOYSA-N 4,8-diaminonaphthalene-1,5-dione Chemical class O=C1C=CC(N)=C2C(=O)C=CC(N)=C21 MHXFYTISBVJROM-UHFFFAOYSA-N 0.000 description 1
NSGMZTNTQKRAFA-UHFFFAOYSA-N 4-(4-heptylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCCCC)CCC1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UHFFFAOYSA-N 0.000 description 1
QKEBUASRTJNJJS-UHFFFAOYSA-N 4-[4-(4-pentylcyclohexyl)phenyl]benzonitrile Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-UHFFFAOYSA-N 0.000 description 1
BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
RPKLKZOWIFNNJN-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis(4-methylanilino)naphthalene-1,4-dione Chemical compound C1=CC(C)=CC=C1NC1=CC(=O)C2=C(O)C(NC=3C=CC(C)=CC=3)=CC(O)=C2C1=O RPKLKZOWIFNNJN-UHFFFAOYSA-N 0.000 description 1
OBYQPYAPRWBVNI-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis(4-methylphenyl)naphthalene-1,4-dione Chemical compound C1=CC(C)=CC=C1C1=CC(=O)C2=C(O)C(C=3C=CC(C)=CC=3)=CC(O)=C2C1=O OBYQPYAPRWBVNI-UHFFFAOYSA-N 0.000 description 1
DXUBLXLUEKBMDC-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis(phenylsulfanyl)naphthalene-1,4-dione Chemical compound OC=1C=2C(=O)C=C(SC=3C=CC=CC=3)C(=O)C=2C(O)=CC=1SC1=CC=CC=C1 DXUBLXLUEKBMDC-UHFFFAOYSA-N 0.000 description 1
IVCAKPPJHCGGCU-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis[(4-methoxyphenyl)sulfanyl]naphthalene-1,4-dione Chemical compound C1=CC(OC)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(OC)=CC=3)=CC(O)=C2C1=O IVCAKPPJHCGGCU-UHFFFAOYSA-N 0.000 description 1
LDZKDJZFGQJNPL-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis[(4-methylphenyl)sulfanyl]naphthalene-1,4-dione Chemical compound C1=CC(C)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(C)=CC=3)=CC(O)=C2C1=O LDZKDJZFGQJNPL-UHFFFAOYSA-N 0.000 description 1
PSXKKSGELMXPSL-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis[(4-pentylphenyl)sulfanyl]naphthalene-1,4-dione Chemical compound C1=CC(CCCCC)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(CCCCC)=CC=3)=CC(O)=C2C1=O PSXKKSGELMXPSL-UHFFFAOYSA-N 0.000 description 1
SODDTNKIVDNTES-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis[(4-propoxyphenyl)sulfanyl]naphthalene-1,4-dione Chemical compound C1=CC(OCCC)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(OCCC)=CC=3)=CC(O)=C2C1=O SODDTNKIVDNTES-UHFFFAOYSA-N 0.000 description 1
IBUMBUYCKKJURL-UHFFFAOYSA-N 5,8-dihydroxy-2,6-bis[(4-propylphenyl)sulfanyl]naphthalene-1,4-dione Chemical compound C1=CC(CCC)=CC=C1SC1=CC(=O)C2=C(O)C(SC=3C=CC(CCC)=CC=3)=CC(O)=C2C1=O IBUMBUYCKKJURL-UHFFFAOYSA-N 0.000 description 1
GOFDYGHZIAZKTO-UHFFFAOYSA-N 5,8-dihydroxy-2,6-dioctylnaphthalene-1,4-dione Chemical compound CCCCCCCCC1=CC(O)=C2C(=O)C(CCCCCCCC)=CC(=O)C2=C1O GOFDYGHZIAZKTO-UHFFFAOYSA-N 0.000 description 1
WBJANJUFFHAAKV-UHFFFAOYSA-N 5,8-dihydroxy-2,6-diphenylnaphthalene-1,4-dione Chemical compound O=C1C=2C(O)=CC(C=3C=CC=CC=3)=C(O)C=2C(=O)C=C1C1=CC=CC=C1 WBJANJUFFHAAKV-UHFFFAOYSA-N 0.000 description 1
ILTACPXSCBVUJS-UHFFFAOYSA-N 5,8-dihydroxy-2,6-dipropoxynaphthalene-1,4-dione Chemical compound CCCOC1=CC(O)=C2C(=O)C(OCCC)=CC(=O)C2=C1O ILTACPXSCBVUJS-UHFFFAOYSA-N 0.000 description 1
AJWZKTSSURWHBQ-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-methoxyanilino)naphthalene-1,4-dione Chemical compound C1=CC(OC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O AJWZKTSSURWHBQ-UHFFFAOYSA-N 0.000 description 1
QEOPKJFDBSVRAW-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-methoxyphenyl)naphthalene-1,4-dione Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=CC(O)=C2C1=O QEOPKJFDBSVRAW-UHFFFAOYSA-N 0.000 description 1
VVPNUXZJCDMGRU-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-methylanilino)naphthalene-1,4-dione Chemical compound C1=CC(C)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O VVPNUXZJCDMGRU-UHFFFAOYSA-N 0.000 description 1
IGOMGHKVEWACBI-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-octylanilino)naphthalene-1,4-dione Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O IGOMGHKVEWACBI-UHFFFAOYSA-N 0.000 description 1
QATYTPVDSBXDIX-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-octylphenyl)sulfanylnaphthalene-1,4-dione Chemical compound C1=CC(CCCCCCCC)=CC=C1SC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O QATYTPVDSBXDIX-UHFFFAOYSA-N 0.000 description 1
QBKMQUSXBBWDBT-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-pentylanilino)naphthalene-1,4-dione Chemical compound C1=CC(CCCCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O QBKMQUSXBBWDBT-UHFFFAOYSA-N 0.000 description 1
VBRODSQIKATPCZ-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-propylanilino)naphthalene-1,4-dione Chemical compound C1=CC(CCC)=CC=C1NC1=CC(=O)C2=C(O)C=CC(O)=C2C1=O VBRODSQIKATPCZ-UHFFFAOYSA-N 0.000 description 1
YMSJWBQASSRVNQ-UHFFFAOYSA-N 5,8-dihydroxy-2-phenylnaphthalene-1,4-dione Chemical compound C=1C(=O)C=2C(O)=CC=C(O)C=2C(=O)C=1C1=CC=CC=C1 YMSJWBQASSRVNQ-UHFFFAOYSA-N 0.000 description 1
DQRBQYWUILSPIG-UHFFFAOYSA-N 8-amino-5-hydroxy-4-iminonaphthalen-1-one Chemical compound C1(=N)C2=C(O)C=CC(N)=C2C(=O)C=C1 DQRBQYWUILSPIG-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
YXUSGDUDUHFXCQ-UHFFFAOYSA-N C(CCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O Chemical compound C(CCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O YXUSGDUDUHFXCQ-UHFFFAOYSA-N 0.000 description 1
HTKKLCAWGOAEEV-UHFFFAOYSA-N C(CCCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O Chemical compound C(CCCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O HTKKLCAWGOAEEV-UHFFFAOYSA-N 0.000 description 1
KQMAJQOFAMCILQ-UHFFFAOYSA-N C(CCCCCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O Chemical compound C(CCCCCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O KQMAJQOFAMCILQ-UHFFFAOYSA-N 0.000 description 1
AVWNULROWLFZLZ-UHFFFAOYSA-N C(CCCCCCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O Chemical compound C(CCCCCCC)C1=CC=C(C=C1)C=1C(C2=C(C=CC(=C2C(C1)=O)O)O)=O AVWNULROWLFZLZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
229910052691 Erbium Inorganic materials 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
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
150000001482 benzyl phenyl ethers Chemical class 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
150000004074 biphenyls Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
BVQUETZBXIMAFZ-UHFFFAOYSA-N chembl1328567 Chemical compound C1=CC=C2C(=O)C(O)=C(O)C(=O)C2=C1 BVQUETZBXIMAFZ-UHFFFAOYSA-N 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
DQZKGSRJOUYVPL-UHFFFAOYSA-N cyclohexyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1CCCCC1 DQZKGSRJOUYVPL-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
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
238000011065 in-situ storage Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000008424 iodobenzenes Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
UKYHUQYCBBUNIA-UHFFFAOYSA-N naphthalene-1,5-dione Chemical compound O=C1C=CC=C2C(=O)C=CC=C21 UKYHUQYCBBUNIA-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
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 1
125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
230000005693 optoelectronics Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
150000001629 stilbenes Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000001911 terphenyls Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
150000001608 tolans Chemical class 0.000 description 1
230000017105 transposition Effects 0.000 description 1

Classifications

- 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
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/36—Steroidal liquid crystal compounds
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B13/00—Oxyketone dyes
- C09B13/02—Oxyketone dyes of the naphthalene series, e.g. naphthazarin
- 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Liquid Crystal Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal (AREA)
Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

DD83247475A 1982-01-28 1983-01-26 Fluessigkristallines dielektrikum DD206785A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823202761 DE3202761A1 (de)	1982-01-28	1982-01-28	Fluessigkristallines dielektrikum, neue farbstoffe, verfahren zu ihrer herstellung und elektrooptisches anzeigeelement

Publications (1)

Publication Number	Publication Date
DD206785A5 true DD206785A5 (de)	1984-02-08

Family

ID=6154149

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83247475A DD206785A5 (de)	1982-01-28	1983-01-26	Fluessigkristallines dielektrikum

Country Status (10)

Country	Link
US (1)	US4499004A (fr)
EP (1)	EP0085335B1 (fr)
JP (1)	JPS58129055A (fr)
KR (1)	KR840003276A (fr)
AT (1)	ATE18915T1 (fr)
CA (1)	CA1198121A (fr)
DD (1)	DD206785A5 (fr)
DE (2)	DE3202761A1 (fr)
HK (1)	HK97086A (fr)
SG (1)	SG64386G (fr)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3126108A1 (de) *	1981-07-02	1983-01-20	Merck Patent Gmbh, 6100 Darmstadt	"fluessigkristallines dielektrikum, neue dichroitische naphthochinonfarbstoffe und elektrooptisches anzeigeelement"
KR100380146B1 (ko) *	1998-02-13	2003-08-21	주식회사 엘지생명과학	나프토퀴논구조를갖는사이클린-의존키나아제저해제화합물
GB0817175D0 (en) *	2008-09-19	2008-10-29	Liquavista Bv	Improvements in relation to electrowetting elements
CN104837959B (zh)	2012-12-13	2017-09-19	默克专利股份有限公司	液晶介质
US10114264B2 (en)	2013-03-05	2018-10-30	Merck Patent Gmbh	Device for regulating the passage of energy
CN105190419A (zh)	2013-05-08	2015-12-23	默克专利股份有限公司	用于调节光学能量通过的具有两个液晶切换层的装置
WO2014187529A1 (fr)	2013-05-24	2014-11-27	Merck Patent Gmbh	Dispositif de régulation du passage d'énergie contenant un composé de colorant dichroïque
WO2015090506A1 (fr)	2013-12-19	2015-06-25	Merck Patent Gmbh	Dispositif permettant de réguler un passage de lumière
DE102015005800A1 (de)	2015-05-06	2016-11-10	Merck Patent Gmbh	Thiadiazolochinoxalinderivate
WO2017008880A1 (fr)	2015-07-10	2017-01-19	Merck Patent Gmbh	Dithioalkylpyrrolopyrroles et leur utilisation en tant que colorants
EP3475389B1 (fr)	2016-06-28	2020-02-26	Merck Patent GmbH	Milieu cristallin liquide
JP6972103B2 (ja)	2016-07-19	2021-11-24	メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツングMerck Patent GmbH	液晶媒体
US11667845B2 (en)	2018-06-11	2023-06-06	Merck Patent Gmbh	Liquid crystalline medium
CN112313311B (zh)	2018-06-20	2024-08-06	默克专利股份有限公司	液晶介质
KR102910078B1 (ko)	2018-09-25	2026-01-12	메르크 파텐트 게엠베하	아조 염료
WO2020104563A1 (fr)	2018-11-23	2020-05-28	Merck Patent Gmbh	Composition de coloration dichroïque
US11952528B2 (en)	2018-12-19	2024-04-09	Merck Patent Gmbh	Switching layers for use in a switching element
US12134725B2 (en)	2019-06-17	2024-11-05	Merck Patent Gmbh	Liquid crystal-based light valve
EP3839620B1 (fr)	2019-12-16	2025-02-26	Merck Patent GmbH	Dispositif de régulation de transmission de lumière
KR20230116055A (ko)	2020-12-11	2023-08-03	메르크 파텐트 게엠베하	광 투과 조절 장치
WO2023094404A1 (fr)	2021-11-24	2023-06-01	Merck Patent Gmbh	Milieu de cristaux liquides et dispositif d'affichage à cristaux liquides
JP2026522286A (ja)	2023-06-05	2026-07-07	メルクパテントゲゼルシャフトミットベシュレンクテルハフツング	液晶媒体
WO2025061649A1 (fr)	2023-09-20	2025-03-27	Merck Patent Gmbh	Milieu à cristaux liquides
KR20250113342A (ko)	2024-01-18	2025-07-25	메르크 파텐트 게엠베하	액정 매질
WO2025190813A1 (fr)	2024-03-11	2025-09-18	Merck Patent Gmbh	Milieu à cristaux liquides
WO2026052594A1 (fr)	2024-09-05	2026-03-12	Merck Patent Gmbh	Valve optique à base de cristaux liquides
WO2026099217A1 (fr)	2024-11-05	2026-05-15	Merck Patent Gmbh	Milieu à cristaux liquides

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2311032A (en) *		1943-02-16		B-amino-s-hydroxy-z-sulphoethyl
DE167641C (fr) *
US619114A (en) *		1899-02-07		Oscar bally
US631613A (en) *	1897-12-27	1899-08-22	Basf Ag	Black dye and process of making same.
US669894A (en) *	1899-04-11	1901-03-12	Basf Ag	Blue dye of naphthalene series and process of making same.
US647370A (en) *	1899-11-14	1900-04-10	Basf Ag	Green dye.
US668445A (en) *	1900-01-24	1901-02-19	Hoechst Ag	Blue wool-dye and process of making same.
US1991885A (en) *	1928-08-01	1935-02-19	Celanese Corp	Dyestuffs of the naphthoquinone series
US2301382A (en) *	1940-01-06	1942-11-10	Eastman Kodak Co	1,4-naphthoquinone compounds
CH386981A (de) *	1961-11-15	1965-04-30	Geigy Ag J R	Verfahren zum Färben von hydrophoben Textilfasern mit Naphthochinoniminfarbstoffen
US3479374A (en) *	1966-09-29	1969-11-18	Eastman Kodak Co	Preparation of quinones
DE2658568C2 (de) *	1975-12-25	1983-12-22	Sharp K.K., Osaka	Flüssigkristall-Darstellungseinrichtung mit einem pleochroitischen Farbstoff-Gastmaterial und einem nematischen Flüssigkristall-Wirtmaterial
US4288147A (en) *	1978-12-20	1981-09-08	Timex Corporation	Electro-optical composition of the guest-host type
CH638828A5 (de) *	1978-12-21	1983-10-14	Bbc Brown Boveri & Cie	Fluessigkristallmischung.
US4360447A (en) *	1979-03-16	1982-11-23	Mitsui Toatsu Chemicals, Inc.	Composition for liquid crystal color display elements
US4304683A (en) *	1979-03-16	1981-12-08	Mitsui Toatsu Chemicals, Inc.	Composition for liquid crystal color display element
CH641828A5 (fr) *	1979-08-17	1984-03-15	Ebauches Sa	Composition a base de cristal liquide pour dispositif electro-optique.
EP0025809A1 (fr) *	1979-09-21	1981-04-01	BBC Aktiengesellschaft Brown, Boveri & Cie.	Mélange de cristaux liquides
CH642393A5 (fr) *	1979-10-02	1984-04-13	Ebauches Sa	Composition a base de cristal liquide pour dispositif electro-optique.
JPS56100885A (en) *	1980-01-17	1981-08-13	Mitsui Toatsu Chem Inc	Composition for liquid crystal color display
DE3007198A1 (de) *	1980-02-26	1981-09-03	Siemens AG, 1000 Berlin und 8000 München	Pleochroitischer anthrachinon-farbstoff, verfahren zu seiner herstellung und verwendung des farbstoffs
DE3014933A1 (de) *	1980-04-18	1981-10-29	Bayer Ag, 5090 Leverkusen	Fluessigkristalline materialien enthaltend anthrachinonfarbstoffe
DE3040102A1 (de) *	1980-10-24	1982-06-03	Merck Patent Gmbh, 6100 Darmstadt	Dichroitische anthrachinonfarbstoffe, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement
DE3126108A1 (de) *	1981-07-02	1983-01-20	Merck Patent Gmbh, 6100 Darmstadt	"fluessigkristallines dielektrikum, neue dichroitische naphthochinonfarbstoffe und elektrooptisches anzeigeelement"

1982
- 1982-01-28 DE DE19823202761 patent/DE3202761A1/de not_active Withdrawn
1983
- 1983-01-17 EP EP83100346A patent/EP0085335B1/fr not_active Expired
- 1983-01-17 AT AT83100346T patent/ATE18915T1/de not_active IP Right Cessation
- 1983-01-17 DE DE8383100346T patent/DE3362737D1/de not_active Expired
- 1983-01-26 DD DD83247475A patent/DD206785A5/de unknown
- 1983-01-26 KR KR1019830000294A patent/KR840003276A/ko not_active Withdrawn
- 1983-01-26 CA CA000420535A patent/CA1198121A/fr not_active Expired
- 1983-01-28 US US06/462,153 patent/US4499004A/en not_active Expired - Fee Related
- 1983-01-28 JP JP58011616A patent/JPS58129055A/ja active Pending
1986
- 1986-07-24 SG SG64386A patent/SG64386G/en unknown
- 1986-12-11 HK HK970/86A patent/HK97086A/xx unknown

Also Published As

Publication number	Publication date
EP0085335A2 (fr)	1983-08-10
JPS58129055A (ja)	1983-08-01
EP0085335A3 (en)	1983-11-30
KR840003276A (ko)	1984-08-20
DE3202761A1 (de)	1983-08-04
US4499004A (en)	1985-02-12
ATE18915T1 (de)	1986-04-15
SG64386G (en)	1987-09-18
CA1198121A (fr)	1985-12-17
EP0085335B1 (fr)	1986-04-02
DE3362737D1 (en)	1986-05-07
HK97086A (en)	1986-12-19

Publication	Publication Date	Title
EP0085335B1 (fr)	1986-04-02	Diélectrique à cristaux liquides, nouveaux colorants, procédé pour leur préparation et élément d'affichage électro-optique
DE3040632C2 (fr)	1989-02-02
DE3211601C2 (fr)	1990-04-19
EP0069257B1 (fr)	1984-09-26	Diélectrique à base de cristaux liquides et dispositif d'affichage électrooptique
EP0107759B1 (fr)	1992-12-16	Dérivés du cyclohexane et leur application comme components de cristaux liquides
DE3401320C2 (fr)	1992-06-11
DE3225290C2 (fr)	1993-09-16
CH647252A5 (de)	1985-01-15	Dichroitische anthrachinonfarbstoffe und deren verwendung in fluessigkristallinen dielektrika fuer elektrooptisches anzeigeelement.
EP0256097B1 (fr)	1990-08-01	Composés vinyliques et phase liquide cristalline
EP0308438B1 (fr)	1993-09-29	Phase liquide cristalline contenant des tolanes
DE2701591B2 (de)	1979-05-03	Hexahydroterphenylderivate und deren Verwendung in fliissigkristallinen Dielektrika
DD204101A5 (de)	1983-11-16	Fluessigkristalline halogenverbindungen enthaltende dielektrika
EP0199004A1 (fr)	1986-10-29	Dérivés de la pyrimidine
DD209205A5 (de)	1984-04-25	Fluessigkristallines dielektrikum fuer elektrooptische anzeigeelemente
DD204100A5 (de)	1983-11-16	Dichroitische anthrachinonfarbstoffe enthaltende fluessigkeitskristalline dielektika
EP0088907B1 (fr)	1985-10-16	Dérivés biphényliques halogénés
EP0019060B1 (fr)	1982-04-21	Dicétones, procédé pour leur préparation et leur utilisation comme composés de diélectriques à cristaux liquides
DE3101290C2 (fr)	1988-02-04
EP0110205B1 (fr)	1987-12-09	Mélanges "cristaux liquides" colorés contenant des phényléthanes
EP0118061B1 (fr)	1988-09-14	Systèmes à cristaux liquides du type "hôte-récepteur"
DE3434335A1 (de)	1986-03-27	Fluessigkristalline phase
DE3711306A1 (de)	1988-10-20	Tolanderivate und verwendung von carbonitrilen in fluessigkristallinen phasen fuer anzeigeelemente basierend auf dem ecb-effekt
DE3717397A1 (de)	1988-12-01	Cyclohexenderivate
DE3831336A1 (de)	1990-03-29	Tolane
DE3617431A1 (de)	1987-11-26	Cyclohexanderivate