JPS6241991B2 - - Google Patents
Info
- Publication number
- JPS6241991B2 JPS6241991B2 JP60227708A JP22770885A JPS6241991B2 JP S6241991 B2 JPS6241991 B2 JP S6241991B2 JP 60227708 A JP60227708 A JP 60227708A JP 22770885 A JP22770885 A JP 22770885A JP S6241991 B2 JPS6241991 B2 JP S6241991B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- diamino
- dye
- group
- anthraquinone
- 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
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 18
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001000 anthraquinone dye Substances 0.000 claims 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 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 29
- -1 1,4-diamino-N- ethyl-2-anthraquinonylcarboxamide Chemical compound 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 230000005684 electric field Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 2
- RDISTOCQRJJICR-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCC)=CC=C1C1=CC=C(C#N)C=C1 RDISTOCQRJJICR-UHFFFAOYSA-N 0.000 description 2
- VBQMNDWDPXFYNL-UHFFFAOYSA-N 4-[4-(3-methylbutyl)phenyl]benzonitrile Chemical group C1=CC(CCC(C)C)=CC=C1C1=CC=C(C#N)C=C1 VBQMNDWDPXFYNL-UHFFFAOYSA-N 0.000 description 2
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 2
- MVZLXPLGDIUUID-UHFFFAOYSA-N C(CC)OC(=O)C1=C(C=2C(C3=CC=CC=C3C(C2C(=C1)N)=O)=O)N Chemical compound C(CC)OC(=O)C1=C(C=2C(C3=CC=CC=C3C(C2C(=C1)N)=O)=O)N MVZLXPLGDIUUID-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- WQGHUOVEPPWOSM-UHFFFAOYSA-N 1,4-diamino-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(Cl)=O)C=C2N WQGHUOVEPPWOSM-UHFFFAOYSA-N 0.000 description 1
- VCZXXRSDLZIADZ-UHFFFAOYSA-N 1,4-diamino-n-butyl-9,10-dioxoanthracene-2-carboxamide Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)NCCCC)=CC(N)=C3C(=O)C2=C1 VCZXXRSDLZIADZ-UHFFFAOYSA-N 0.000 description 1
- YPMXOBIOGYKURX-UHFFFAOYSA-N 1,4-diamino-n-methyl-9,10-dioxoanthracene-2-carboxamide Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)NC)=CC(N)=C3C(=O)C2=C1 YPMXOBIOGYKURX-UHFFFAOYSA-N 0.000 description 1
- AGBBHFFHHCLFCW-UHFFFAOYSA-N 1-amino-4-nitro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC(C(Cl)=O)=C2N AGBBHFFHHCLFCW-UHFFFAOYSA-N 0.000 description 1
- JPBFKTCKZLMJED-UHFFFAOYSA-N 4-(4-heptoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 JPBFKTCKZLMJED-UHFFFAOYSA-N 0.000 description 1
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 1
- AMRDCKRNXLLBCG-UHFFFAOYSA-N 4-(4-pentyl-2-phenylphenyl)benzonitrile Chemical group C=1C=CC=CC=1C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 AMRDCKRNXLLBCG-UHFFFAOYSA-N 0.000 description 1
- RZCQJZFWJZHMPK-UHFFFAOYSA-N 4-(4-propoxyphenyl)benzonitrile Chemical group C1=CC(OCCC)=CC=C1C1=CC=C(C#N)C=C1 RZCQJZFWJZHMPK-UHFFFAOYSA-N 0.000 description 1
- GAGWWLHWKFKPIC-UHFFFAOYSA-N 4-phenylbenzene-1,3-dicarbonitrile Chemical group N#CC1=CC(C#N)=CC=C1C1=CC=CC=C1 GAGWWLHWKFKPIC-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- YEPFOQQNFGBXPS-UHFFFAOYSA-N butyl 1,4-diamino-9,10-dioxoanthracene-2-carboxylate Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)OCCCC)=CC(N)=C3C(=O)C2=C1 YEPFOQQNFGBXPS-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WCLNGBQPTVENHV-MKQVXYPISA-N cholesteryl nonanoate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCCC)C1 WCLNGBQPTVENHV-MKQVXYPISA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- OBLIXNGHYJVMEH-UHFFFAOYSA-N cyclohexyl 1,4-diamino-9,10-dioxoanthracene-2-carboxylate Chemical compound NC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=1C(=O)OC1CCCCC1 OBLIXNGHYJVMEH-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AJUHDTQHGUNGBL-UHFFFAOYSA-N ethyl 1,4-diamino-9,10-dioxoanthracene-2-carboxylate Chemical compound C(C)OC(=O)C1=C(C=2C(C3=CC=CC=C3C(C2C(=C1)N)=O)=O)N AJUHDTQHGUNGBL-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- BAVVZBIXCSLNQU-UHFFFAOYSA-N methyl 1,4-diamino-9,10-dioxoanthracene-2-carboxylate Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)OC)=CC(N)=C3C(=O)C2=C1 BAVVZBIXCSLNQU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KQBPPKIWYDVYHG-UHFFFAOYSA-N propan-2-yl 1,4-diamino-9,10-dioxoanthracene-2-carboxylate Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)OC(C)C)=CC(N)=C3C(=O)C2=C1 KQBPPKIWYDVYHG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22770885A JPS61148291A (ja) | 1985-10-15 | 1985-10-15 | 液晶カラ−表示用組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22770885A JPS61148291A (ja) | 1985-10-15 | 1985-10-15 | 液晶カラ−表示用組成物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3005779A Division JPS55123673A (en) | 1979-03-16 | 1979-03-16 | Liquid crystal color display device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61148291A JPS61148291A (ja) | 1986-07-05 |
| JPS6241991B2 true JPS6241991B2 (fr) | 1987-09-05 |
Family
ID=16865106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22770885A Granted JPS61148291A (ja) | 1985-10-15 | 1985-10-15 | 液晶カラ−表示用組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61148291A (fr) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55123673A (en) * | 1979-03-16 | 1980-09-24 | Mitsui Toatsu Chem Inc | Liquid crystal color display device |
-
1985
- 1985-10-15 JP JP22770885A patent/JPS61148291A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55123673A (en) * | 1979-03-16 | 1980-09-24 | Mitsui Toatsu Chem Inc | Liquid crystal color display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61148291A (ja) | 1986-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6115915B2 (fr) | ||
| EP0060895B1 (fr) | Composition pour l'affichage couleur de cristaux liquides | |
| KR850000050B1 (ko) | 다색성 염료를 함유하는 액정조성물 | |
| US4304683A (en) | Composition for liquid crystal color display element | |
| GB2037803A (en) | Liquid crystal mixture | |
| EP0048583B1 (fr) | Compositions des cristaux liquides, contenant des colorants pléochroiques, anthraquinoniques, dispositifs d'affichage contenant des cristaux liquides basés sur ces compositions, et les colorants | |
| EP0049036B1 (fr) | Compositions organiques appropriées à un dispositif, contenant des cristaux liquides, basé sur l'effet reçu-receveur dit guest-host | |
| JPS6045678B2 (ja) | アントラキノン系化合物を含む液晶カラ−表示用組成物 | |
| JPH0517274B2 (fr) | ||
| JPS59133282A (ja) | 液晶表示装置用等方性染料 | |
| JPS6241991B2 (fr) | ||
| EP0120717B1 (fr) | Colorants anthraquinoniques et compositions de cristaux liquides contenant ces colorants | |
| JPS6149352B2 (fr) | ||
| JPS6146032B2 (fr) | ||
| JPS6046152B2 (ja) | 液晶カラ−表示用組成物 | |
| JP2567075B2 (ja) | 液晶表示用二色性色素 | |
| JP2567057B2 (ja) | 液晶表示用二色性色素 | |
| JP2567054B2 (ja) | 液晶表示用二色性色素 | |
| JPS641000B2 (fr) | ||
| KR870001882B1 (ko) | 안트라퀴논 염료의 제조방법 및 이 염료로 이루어진 액정조성물 | |
| JPS6147193B2 (fr) | ||
| JPH0539430A (ja) | 液晶添加用二色性色素 | |
| JPH042626B2 (fr) | ||
| JPH049187B2 (fr) | ||
| JPS6146031B2 (fr) |