JPS63301850A - アゾ化合物からなる液晶用二色性色素 - Google Patents
アゾ化合物からなる液晶用二色性色素Info
- Publication number
- JPS63301850A JPS63301850A JP63006210A JP621088A JPS63301850A JP S63301850 A JPS63301850 A JP S63301850A JP 63006210 A JP63006210 A JP 63006210A JP 621088 A JP621088 A JP 621088A JP S63301850 A JPS63301850 A JP S63301850A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- azo compound
- liquid crystal
- dye
- 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
- -1 Azo compound Chemical class 0.000 title claims abstract description 20
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 21
- 239000000049 pigment Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 150000001448 anilines Chemical class 0.000 abstract description 4
- KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 abstract description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VDQQJMHXZCMNMU-UHFFFAOYSA-N 1-phenylpyrrolidine Chemical compound C1CCCN1C1=CC=CC=C1 VDQQJMHXZCMNMU-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BWAUVGNNSIBWFM-UHFFFAOYSA-N 4-[(4-butylphenyl)diazenyl]aniline Chemical compound C1=CC(CCCC)=CC=C1N=NC1=CC=C(N)C=C1 BWAUVGNNSIBWFM-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 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
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-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
- 238000011161 development Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AJSINQAAKNYUDA-UHFFFAOYSA-M sodium;anilinomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CNC1=CC=CC=C1 AJSINQAAKNYUDA-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63006210A JPS63301850A (ja) | 1988-01-13 | 1988-01-13 | アゾ化合物からなる液晶用二色性色素 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63006210A JPS63301850A (ja) | 1988-01-13 | 1988-01-13 | アゾ化合物からなる液晶用二色性色素 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63301850A true JPS63301850A (ja) | 1988-12-08 |
| JPH0238615B2 JPH0238615B2 (enrdf_load_stackoverflow) | 1990-08-31 |
Family
ID=11632165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63006210A Granted JPS63301850A (ja) | 1988-01-13 | 1988-01-13 | アゾ化合物からなる液晶用二色性色素 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63301850A (enrdf_load_stackoverflow) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0517776A (ja) * | 1991-06-18 | 1993-01-26 | Mitsubishi Kasei Corp | 調光材料およびそれを含む調光素子 |
| JPH07224231A (ja) * | 1994-02-10 | 1995-08-22 | Mitsubishi Chem Corp | 二色性色素、該色素を含む液晶組成物および液晶素子 |
| JPH07224281A (ja) * | 1994-02-09 | 1995-08-22 | Mitsubishi Chem Corp | 液晶組成物および液晶素子 |
| US5755995A (en) * | 1996-05-09 | 1998-05-26 | Shin-Etsu Chemical Co., Ltd. | Guest host liquid crystal composition |
| JPH10183121A (ja) * | 1996-10-21 | 1998-07-14 | Mitsubishi Chem Corp | 液晶組成物および液晶表示素子 |
| JPH1180735A (ja) * | 1997-02-12 | 1999-03-26 | Mitsubishi Chem Corp | 液晶組成物および液晶表示素子 |
| JP2013534945A (ja) * | 2010-06-14 | 2013-09-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 黒色二色性染料 |
| WO2018164252A1 (ja) * | 2017-03-09 | 2018-09-13 | 富士フイルム株式会社 | 組成物、二色性物質、光吸収異方性膜、積層体および画像表示装置 |
| US10690953B2 (en) | 2015-03-16 | 2020-06-23 | Sumitomo Chemical Company, Limited | Polarizing plate and circularly polarizing plate |
| WO2020241313A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ |
| WO2020241312A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ用偏光板 |
| US11899167B2 (en) | 2019-05-28 | 2024-02-13 | Toyobo Co., Ltd. | Polyester film, laminated film, and use thereof |
| US11926720B2 (en) | 2019-05-28 | 2024-03-12 | Toyobo Co., Ltd. | Polyester film and application therefor |
| US11934226B2 (en) | 2019-02-08 | 2024-03-19 | Toyobo Co., Ltd. | Foldable display and portable terminal device |
| US11939499B2 (en) | 2019-05-28 | 2024-03-26 | Toyobo Co., Ltd. | Multilayer film and use of same |
| US11997916B2 (en) | 2019-02-08 | 2024-05-28 | Toyobo Co., Ltd. | Polyester film and use thereof |
| US12319801B2 (en) | 2019-07-12 | 2025-06-03 | Toyobo Co., Ltd. | Hard coating film for foldable display, and application of said film |
| US12351730B2 (en) | 2019-07-12 | 2025-07-08 | Toyobo Co., Ltd. | Hard coat film for foldable display and use thereof |
| US12354504B2 (en) | 2019-05-28 | 2025-07-08 | Toyobo Co., Ltd. | Transparent conductive polyester film and use of same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08204450A (ja) * | 1995-01-30 | 1996-08-09 | Nec Corp | 半導体集積回路 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5429333A (en) * | 1977-08-05 | 1979-03-05 | Basf Ag | Azo dyestuff |
| JPS5589355A (en) * | 1978-12-11 | 1980-07-05 | Bayer Ag | Manufacture of disazo dyestuff*two or three kinds of disazo dyestuff mixture and method of coloring and*or characterizing organic matter |
-
1988
- 1988-01-13 JP JP63006210A patent/JPS63301850A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5429333A (en) * | 1977-08-05 | 1979-03-05 | Basf Ag | Azo dyestuff |
| JPS5589355A (en) * | 1978-12-11 | 1980-07-05 | Bayer Ag | Manufacture of disazo dyestuff*two or three kinds of disazo dyestuff mixture and method of coloring and*or characterizing organic matter |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0517776A (ja) * | 1991-06-18 | 1993-01-26 | Mitsubishi Kasei Corp | 調光材料およびそれを含む調光素子 |
| JPH07224281A (ja) * | 1994-02-09 | 1995-08-22 | Mitsubishi Chem Corp | 液晶組成物および液晶素子 |
| JPH07224231A (ja) * | 1994-02-10 | 1995-08-22 | Mitsubishi Chem Corp | 二色性色素、該色素を含む液晶組成物および液晶素子 |
| US5755995A (en) * | 1996-05-09 | 1998-05-26 | Shin-Etsu Chemical Co., Ltd. | Guest host liquid crystal composition |
| JPH10183121A (ja) * | 1996-10-21 | 1998-07-14 | Mitsubishi Chem Corp | 液晶組成物および液晶表示素子 |
| JPH1180735A (ja) * | 1997-02-12 | 1999-03-26 | Mitsubishi Chem Corp | 液晶組成物および液晶表示素子 |
| JP2013534945A (ja) * | 2010-06-14 | 2013-09-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 黒色二色性染料 |
| US9057020B2 (en) | 2010-06-14 | 2015-06-16 | Basf Se | Black dichroic dye |
| US10690953B2 (en) | 2015-03-16 | 2020-06-23 | Sumitomo Chemical Company, Limited | Polarizing plate and circularly polarizing plate |
| WO2018164252A1 (ja) * | 2017-03-09 | 2018-09-13 | 富士フイルム株式会社 | 組成物、二色性物質、光吸収異方性膜、積層体および画像表示装置 |
| JPWO2018164252A1 (ja) * | 2017-03-09 | 2020-04-23 | 富士フイルム株式会社 | 組成物、二色性物質、光吸収異方性膜、積層体および画像表示装置 |
| CN110461951A (zh) * | 2017-03-09 | 2019-11-15 | 富士胶片株式会社 | 组合物、二色性物质、吸光各向异性膜、层叠体及图像显示装置 |
| JP2022008941A (ja) * | 2017-03-09 | 2022-01-14 | 富士フイルム株式会社 | 組成物、二色性物質、光吸収異方性膜、積層体および画像表示装置 |
| CN110461951B (zh) * | 2017-03-09 | 2022-04-08 | 富士胶片株式会社 | 组合物、二色性物质、吸光各向异性膜、层叠体及图像显示装置 |
| JP2023143933A (ja) * | 2017-03-09 | 2023-10-06 | 富士フイルム株式会社 | 組成物、二色性物質、光吸収異方性膜、積層体および画像表示装置 |
| US11997916B2 (en) | 2019-02-08 | 2024-05-28 | Toyobo Co., Ltd. | Polyester film and use thereof |
| US11934226B2 (en) | 2019-02-08 | 2024-03-19 | Toyobo Co., Ltd. | Foldable display and portable terminal device |
| US11926720B2 (en) | 2019-05-28 | 2024-03-12 | Toyobo Co., Ltd. | Polyester film and application therefor |
| US11899167B2 (en) | 2019-05-28 | 2024-02-13 | Toyobo Co., Ltd. | Polyester film, laminated film, and use thereof |
| US11939499B2 (en) | 2019-05-28 | 2024-03-26 | Toyobo Co., Ltd. | Multilayer film and use of same |
| US12354504B2 (en) | 2019-05-28 | 2025-07-08 | Toyobo Co., Ltd. | Transparent conductive polyester film and use of same |
| WO2020241312A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ用偏光板 |
| WO2020241313A1 (ja) | 2019-05-30 | 2020-12-03 | 東洋紡株式会社 | 折りたたみ型ディスプレイ |
| US12298547B2 (en) | 2019-05-30 | 2025-05-13 | Toyobo Co., Ltd. | Foldable display |
| US12319801B2 (en) | 2019-07-12 | 2025-06-03 | Toyobo Co., Ltd. | Hard coating film for foldable display, and application of said film |
| US12351730B2 (en) | 2019-07-12 | 2025-07-08 | Toyobo Co., Ltd. | Hard coat film for foldable display and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0238615B2 (enrdf_load_stackoverflow) | 1990-08-31 |
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