JPS6147193B2 - - Google Patents
Info
- Publication number
- JPS6147193B2 JPS6147193B2 JP6399679A JP6399679A JPS6147193B2 JP S6147193 B2 JPS6147193 B2 JP S6147193B2 JP 6399679 A JP6399679 A JP 6399679A JP 6399679 A JP6399679 A JP 6399679A JP S6147193 B2 JPS6147193 B2 JP S6147193B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- liquid crystal
- formula
- display device
- cyano
- 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 29
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000001000 anthraquinone dye Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 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 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000742 Cotton Polymers 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000001047 purple dye Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- -1 silane compound Chemical class 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- IEWDGUMBUFXBCC-UHFFFAOYSA-N 1,4-diamino-2-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Br)C=C2N IEWDGUMBUFXBCC-UHFFFAOYSA-N 0.000 description 1
- APTMNWLNGQKLPE-UHFFFAOYSA-N 2-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=CC=C1C#N APTMNWLNGQKLPE-UHFFFAOYSA-N 0.000 description 1
- BPUAQNKWCBCCAA-UHFFFAOYSA-N 2-bromo-1,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(Br)C=C2O BPUAQNKWCBCCAA-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
- 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 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
- 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 1
- 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 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003518 caustics Substances 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
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6399679A JPS55157676A (en) | 1979-05-25 | 1979-05-25 | Composition for liquid crystal color display element |
| US06/129,315 US4360447A (en) | 1979-03-16 | 1980-03-11 | Composition for liquid crystal color display elements |
| DE19803009974 DE3009974A1 (de) | 1979-03-16 | 1980-03-14 | Zusammensetzung fuer fluessigkristall- farbanzeige-elemente |
| CH203180A CH643290A5 (de) | 1979-03-16 | 1980-03-14 | Gemisch fuer farbig anzeigende, nematische fluessigkristall-anzeigeelemente. |
| GB8008667A GB2051114B (en) | 1979-03-16 | 1980-03-14 | Composition for liquid crystal colour display elements |
| FR8005873A FR2451393A1 (fr) | 1979-03-16 | 1980-03-17 | Composition destinee a des elements d'affichage en couleur a cristaux liquides |
| US06/405,267 US4473486A (en) | 1979-03-16 | 1982-08-04 | Composition for liquid crystal color display elements |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6399679A JPS55157676A (en) | 1979-05-25 | 1979-05-25 | Composition for liquid crystal color display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55157676A JPS55157676A (en) | 1980-12-08 |
| JPS6147193B2 true JPS6147193B2 (fr) | 1986-10-17 |
Family
ID=13245379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6399679A Granted JPS55157676A (en) | 1979-03-16 | 1979-05-25 | Composition for liquid crystal color display element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55157676A (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5738876A (en) * | 1980-08-21 | 1982-03-03 | Mitsubishi Chem Ind Ltd | Liquid crystal composition |
| DE3014933A1 (de) * | 1980-04-18 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | Fluessigkristalline materialien enthaltend anthrachinonfarbstoffe |
| JPS57117581A (en) * | 1981-01-12 | 1982-07-22 | Sumitomo Chem Co Ltd | Liquid crystal display element |
-
1979
- 1979-05-25 JP JP6399679A patent/JPS55157676A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55157676A (en) | 1980-12-08 |
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