JPH0243791B2 - - Google Patents
Info
- Publication number
- JPH0243791B2 JPH0243791B2 JP57028033A JP2803382A JPH0243791B2 JP H0243791 B2 JPH0243791 B2 JP H0243791B2 JP 57028033 A JP57028033 A JP 57028033A JP 2803382 A JP2803382 A JP 2803382A JP H0243791 B2 JPH0243791 B2 JP H0243791B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- liquid crystal
- dye
- carbon atoms
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 124
- 239000000463 material Substances 0.000 claims description 114
- 239000004973 liquid crystal related substance Substances 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 32
- -1 anthraquinone compound Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 23
- 125000004149 thio group Chemical group *S* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 7
- 239000003989 dielectric material Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000001000 anthraquinone dye Substances 0.000 claims 3
- 239000000047 product Substances 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 150000003573 thiols Chemical class 0.000 description 31
- 230000000694 effects Effects 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 230000005684 electric field Effects 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000004056 anthraquinones Chemical class 0.000 description 11
- 230000008033 biological extinction Effects 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000004988 Nematic liquid crystal Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000001044 red dye Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000001043 yellow dye Substances 0.000 description 4
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 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 3
- 238000000151 deposition Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000001429 visible spectrum Methods 0.000 description 3
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 2
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 2
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000013014 purified material Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- DCKYBPULWXTYJB-UHFFFAOYSA-N 1,2,3-trichloroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C(Cl)=C2Cl DCKYBPULWXTYJB-UHFFFAOYSA-N 0.000 description 1
- CYCVXTXWERXGJY-UHFFFAOYSA-N 1,2-dichloro-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C([N+](=O)[O-])C(Cl)=C2Cl CYCVXTXWERXGJY-UHFFFAOYSA-N 0.000 description 1
- DUJPMUKIEFLXRE-UHFFFAOYSA-N 1,4,5,8-tetrachloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2Cl DUJPMUKIEFLXRE-UHFFFAOYSA-N 0.000 description 1
- PQCMPESVEIOFCU-UHFFFAOYSA-N 1,4,5,8-tetrakis[(4-tert-butylphenyl)sulfanyl]anthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC(C=1C(=O)C2=C(SC=3C=CC(=CC=3)C(C)(C)C)C=CC(SC=3C=CC(=CC=3)C(C)(C)C)=C2C(=O)C=11)=CC=C1SC1=CC=C(C(C)(C)C)C=C1 PQCMPESVEIOFCU-UHFFFAOYSA-N 0.000 description 1
- JTYJHBWDNMUPSP-UHFFFAOYSA-N 1,4,5-trichloro-8-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] JTYJHBWDNMUPSP-UHFFFAOYSA-N 0.000 description 1
- GNEBMDXPSAAQCA-UHFFFAOYSA-N 1,4,5-tris(cyclohexylsulfanyl)-8-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(SC2CCCCC2)=C2C(=O)C3=C(SC=4C=CC=CC=4)C=CC(SC4CCCCC4)=C3C(=O)C2=C1SC1CCCCC1 GNEBMDXPSAAQCA-UHFFFAOYSA-N 0.000 description 1
- WSNXSZVGSATKJS-UHFFFAOYSA-N 1,4,5-tris[(4-phenylphenyl)sulfanyl]-8-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(SC=2C=CC(=CC=2)C=2C=CC=CC=2)=C2C(=O)C3=C(SC=4C=CC(=CC=4)C=4C=CC=CC=4)C=CC(SC=4C=CC(=CC=4)C=4C=CC=CC=4)=C3C(=O)C2=C1SC1=CC=CC=C1 WSNXSZVGSATKJS-UHFFFAOYSA-N 0.000 description 1
- HGBWYYMBPQTZNS-UHFFFAOYSA-N 1,4,5-tris[(4-tert-butylphenyl)sulfanyl]-8-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC(C=1C(=O)C2=C(SC=3C=CC(=CC=3)C(C)(C)C)C=CC(SC=3C=CC(=CC=3)C(C)(C)C)=C2C(=O)C=11)=CC=C1SC1=CC=CC=C1 HGBWYYMBPQTZNS-UHFFFAOYSA-N 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
- JGDLEVAYNWLIKN-UHFFFAOYSA-N 1,5-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(SC=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 JGDLEVAYNWLIKN-UHFFFAOYSA-N 0.000 description 1
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
- YFKFSZYCSSBCMI-UHFFFAOYSA-N 1,5-dihydroxy-8-nitro-2,6-di(nonyl)-4-phenyl-10-sulfanylideneanthracen-9-one Chemical compound OC1=C(C=C(C=2C(C3=C(C(=CC(=C3C(C12)=S)C1=CC=CC=C1)CCCCCCCCC)O)=O)[N+](=O)[O-])CCCCCCCCC YFKFSZYCSSBCMI-UHFFFAOYSA-N 0.000 description 1
- LKAXNYHCEJFLEF-UHFFFAOYSA-N 1-(4-nonylphenyl)sulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(CCCCCCCCC)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC(SC=3C=CC=CC=3)=C1C2=O LKAXNYHCEJFLEF-UHFFFAOYSA-N 0.000 description 1
- ICQYRMKYGAVTCP-UHFFFAOYSA-N 1-(4-tert-butylphenyl)sulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC=CC2=C1C(=O)C1=CC=CC(SC=3C=CC=CC=3)=C1C2=O ICQYRMKYGAVTCP-UHFFFAOYSA-N 0.000 description 1
- HMKWKLSAPLPDRS-UHFFFAOYSA-N 1-butyl-4,8-bis(butylamino)-5-phenylsulfanyl-10-sulfanylideneanthracen-9-one Chemical compound C1=2C(=S)C3=C(NCCCC)C=CC(CCCC)=C3C(=O)C=2C(NCCCC)=CC=C1SC1=CC=CC=C1 HMKWKLSAPLPDRS-UHFFFAOYSA-N 0.000 description 1
- ZTQZFTFKOMOJIM-UHFFFAOYSA-N 1-chloro-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=C1SC1=CC=CC=C1 ZTQZFTFKOMOJIM-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical group CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- BEHIDVHWDQNWQN-UHFFFAOYSA-N 1-cyclohexylcyclohexane-1-carbonitrile Chemical compound C1CCCCC1C1(C#N)CCCCC1 BEHIDVHWDQNWQN-UHFFFAOYSA-N 0.000 description 1
- UYXKPGRCZQJQAC-UHFFFAOYSA-N 1-cyclopentyl-5-phenylsulfanyl-10-sulfanylideneanthracen-9-one Chemical compound C=12C(=S)C3=CC=CC(C4CCCC4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 UYXKPGRCZQJQAC-UHFFFAOYSA-N 0.000 description 1
- NQDIFFUKLIFBDC-UHFFFAOYSA-N 1-dodecylsulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C=3C(SCCCCCCCCCCCC)=CC=CC=3C(=O)C2=C1SC1=CC=CC=C1 NQDIFFUKLIFBDC-UHFFFAOYSA-N 0.000 description 1
- ADJALGQQZBTLSY-UHFFFAOYSA-N 1-naphthalen-2-ylsulfanyl-5-phenylsulfanylanthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(SC=4C=C5C=CC=CC5=CC=4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 ADJALGQQZBTLSY-UHFFFAOYSA-N 0.000 description 1
- IQWOXUVBMYLKRP-UHFFFAOYSA-N 1-phenyl-10-sulfanylideneanthracen-9-one Chemical compound C1(=CC=CC=C1)C1=CC=CC=2C(C3=CC=CC=C3C(C1=2)=O)=S IQWOXUVBMYLKRP-UHFFFAOYSA-N 0.000 description 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- WLNDDIWESXCXHM-UHFFFAOYSA-N 2-phenyl-1,4-dioxane Chemical compound C1OCCOC1C1=CC=CC=C1 WLNDDIWESXCXHM-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- JGWWBSUUFGBHCH-UHFFFAOYSA-N 2-phenylpyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC(C=2C=CC=CC=2)=N1 JGWWBSUUFGBHCH-UHFFFAOYSA-N 0.000 description 1
- UVFLEUVMFWRYAU-UHFFFAOYSA-N 4-anilino-5-(4-methylphenyl)sulfanyl-1-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC(C)=CC=C1SC1=CC=CC2=C1C(=O)C1=C(NC=3C=CC=CC=3)C=CC(SC=3C=CC=CC=3)=C1C2=O UVFLEUVMFWRYAU-UHFFFAOYSA-N 0.000 description 1
- KRVHFFQFZQSNLB-UHFFFAOYSA-N 4-phenylbenzenethiol Chemical compound C1=CC(S)=CC=C1C1=CC=CC=C1 KRVHFFQFZQSNLB-UHFFFAOYSA-N 0.000 description 1
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical group C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 244000171726 Scotch broom Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8105959 | 1981-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57172971A JPS57172971A (en) | 1982-10-25 |
| JPH0243791B2 true JPH0243791B2 (de) | 1990-10-01 |
Family
ID=10519961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2803382A Granted JPS57172971A (en) | 1981-02-25 | 1982-02-23 | Substance suitable for guest-host liquid crystal device and liquid crystal electrooptical device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57172971A (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405211A (en) * | 1980-07-29 | 1983-09-20 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal compositions with pleochroic anthraquinone dyes |
| JPS5927956A (ja) * | 1982-07-17 | 1984-02-14 | バイエル・アクチエンゲゼルシヤフト | アントラキノン染料を含む二色性物質及び新規なアントラキノン染料 |
| GB2126599B (en) * | 1982-08-18 | 1986-10-15 | Ici Plc | Pleochrioc anthraquinone dyes |
| DE3244815A1 (de) * | 1982-12-03 | 1984-06-07 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichroitisches material enthaltend anthrachinonfarbstoffe |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55116785A (en) * | 1979-02-23 | 1980-09-08 | Minnesota Mining & Mfg | Liquid crystal composition and electrooptical apparatus |
| JPS5792080A (en) * | 1980-11-28 | 1982-06-08 | Canon Inc | Liquid crystal display |
-
1982
- 1982-02-23 JP JP2803382A patent/JPS57172971A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55116785A (en) * | 1979-02-23 | 1980-09-08 | Minnesota Mining & Mfg | Liquid crystal composition and electrooptical apparatus |
| JPS5792080A (en) * | 1980-11-28 | 1982-06-08 | Canon Inc | Liquid crystal display |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57172971A (en) | 1982-10-25 |
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