JP2015507672A - 高散乱スメクチック相液晶材料及びそれを用いた表示デバイス - Google Patents
高散乱スメクチック相液晶材料及びそれを用いた表示デバイス Download PDFInfo
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- JP2015507672A JP2015507672A JP2014549290A JP2014549290A JP2015507672A JP 2015507672 A JP2015507672 A JP 2015507672A JP 2014549290 A JP2014549290 A JP 2014549290A JP 2014549290 A JP2014549290 A JP 2014549290A JP 2015507672 A JP2015507672 A JP 2015507672A
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- liquid crystal
- phase liquid
- smectic
- smectic phase
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- 239000004990 Smectic liquid crystal Substances 0.000 title claims abstract description 229
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 225
- 239000000463 material Substances 0.000 title claims abstract description 156
- 125000003342 alkenyl group Chemical group 0.000 claims description 37
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 150000004820 halides Chemical class 0.000 claims description 23
- 125000006850 spacer group Chemical group 0.000 claims description 21
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 18
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 15
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 13
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- -1 alkyne compound Chemical class 0.000 claims description 7
- 150000008040 ionic compounds Chemical class 0.000 claims description 7
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 6
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 239000002861 polymer material Substances 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims description 3
- 230000009977 dual effect Effects 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 22
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 238000002834 transmittance Methods 0.000 description 57
- 239000013078 crystal Substances 0.000 description 38
- 238000002156 mixing Methods 0.000 description 29
- 238000012360 testing method Methods 0.000 description 27
- 230000000694 effects Effects 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 210000002858 crystal cell Anatomy 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000010586 diagram Methods 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 11
- 150000001345 alkine derivatives Chemical class 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000010998 test method Methods 0.000 description 9
- 239000004020 conductor Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 230000005684 electric field Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000012769 display material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- VCYXELFOIWRYLA-UHFFFAOYSA-N 4-(4-decoxyphenyl)benzonitrile Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 VCYXELFOIWRYLA-UHFFFAOYSA-N 0.000 description 4
- KXNZYPBRSATHKV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)C KXNZYPBRSATHKV-UHFFFAOYSA-M 0.000 description 4
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
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- SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 2
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
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- 230000000007 visual effect Effects 0.000 description 2
- SAMSVCLASSGXLQ-UHFFFAOYSA-N 2-pentyl-6-(2-phenylphenyl)benzonitrile Chemical group C(CCCC)C=1C(=C(C=CC=1)C=1C(=CC=CC=1)C1=CC=CC=C1)C#N SAMSVCLASSGXLQ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 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
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
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- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- 238000013007 heat curing Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
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- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3466—Pyrimidine with at least another heterocycle in the chain
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- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
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- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
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- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/124—Ph-Ph-Ph-Ph
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
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- C09K2019/181—Ph-C≡C-Ph
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- C09K2019/183—Ph-Ph-C≡C-Ph
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- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3019—Cy-Cy-Ph-Ph
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- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/0009—Materials therefor
- G02F1/0045—Liquid crystals characterised by their physical properties
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13781—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering using smectic liquid crystals
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110451207.7 | 2011-12-29 | ||
| CN201110451207.7A CN103184053B (zh) | 2011-12-29 | 2011-12-29 | 高散射态近晶相液晶材料及其显示器件 |
| PCT/CN2011/085036 WO2013097181A1 (zh) | 2011-12-29 | 2011-12-30 | 高散射态近晶相液晶材料及其显示器件 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2017225370A Division JP2018070889A (ja) | 2011-12-29 | 2017-11-24 | 高散乱スメクチック相液晶材料及びそれを用いた表示デバイス |
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| JP2015507672A true JP2015507672A (ja) | 2015-03-12 |
| JP2015507672A5 JP2015507672A5 (enExample) | 2018-01-11 |
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| JP2017225370A Pending JP2018070889A (ja) | 2011-12-29 | 2017-11-24 | 高散乱スメクチック相液晶材料及びそれを用いた表示デバイス |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2017225370A Pending JP2018070889A (ja) | 2011-12-29 | 2017-11-24 | 高散乱スメクチック相液晶材料及びそれを用いた表示デバイス |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9175220B2 (enExample) |
| EP (1) | EP2799516B1 (enExample) |
| JP (2) | JP2015507672A (enExample) |
| CN (1) | CN103184053B (enExample) |
| WO (1) | WO2013097181A1 (enExample) |
Cited By (5)
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| WO2017126275A1 (ja) * | 2016-01-20 | 2017-07-27 | Jnc株式会社 | ２原子結合基と２，３－ジフルオロフェニレンを有する４環液晶性化合物、液晶組成物および液晶表示素子 |
| JPWO2016199528A1 (ja) * | 2015-06-08 | 2018-01-25 | Jnc株式会社 | ベンゾチオフェンを有する液晶性化合物、液晶組成物および液晶表示素子 |
| JP2019206694A (ja) * | 2018-05-16 | 2019-12-05 | 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 |
| WO2022030344A1 (ja) * | 2020-08-06 | 2022-02-10 | Dic株式会社 | 液晶組成物並びにこれを用いた液晶表示素子、センサ、液晶レンズ、光通信機器及びアンテナ |
| JP2023091998A (ja) * | 2021-12-21 | 2023-07-03 | Dic株式会社 | 化合物、液晶組成物並びにこれを用いた液晶表示素子、センサ、液晶レンズ、光通信機器及びアンテナ |
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- 2011-12-30 US US14/002,961 patent/US9175220B2/en not_active Expired - Fee Related
- 2011-12-30 EP EP11878839.7A patent/EP2799516B1/en active Active
- 2011-12-30 JP JP2014549290A patent/JP2015507672A/ja active Pending
- 2011-12-30 WO PCT/CN2011/085036 patent/WO2013097181A1/zh not_active Ceased
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2016199528A1 (ja) * | 2015-06-08 | 2018-01-25 | Jnc株式会社 | ベンゾチオフェンを有する液晶性化合物、液晶組成物および液晶表示素子 |
| WO2017126275A1 (ja) * | 2016-01-20 | 2017-07-27 | Jnc株式会社 | ２原子結合基と２，３－ジフルオロフェニレンを有する４環液晶性化合物、液晶組成物および液晶表示素子 |
| JPWO2017126275A1 (ja) * | 2016-01-20 | 2018-11-08 | Jnc株式会社 | ２原子結合基と２，３−ジフルオロフェニレンを有する４環液晶性化合物、液晶組成物および液晶表示素子 |
| JP2019206694A (ja) * | 2018-05-16 | 2019-12-05 | 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 |
| JP7553227B2 (ja) | 2018-05-16 | 2024-09-18 | 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 | 液晶媒体 |
| WO2022030344A1 (ja) * | 2020-08-06 | 2022-02-10 | Dic株式会社 | 液晶組成物並びにこれを用いた液晶表示素子、センサ、液晶レンズ、光通信機器及びアンテナ |
| JP2023091998A (ja) * | 2021-12-21 | 2023-07-03 | Dic株式会社 | 化合物、液晶組成物並びにこれを用いた液晶表示素子、センサ、液晶レンズ、光通信機器及びアンテナ |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013097181A1 (zh) | 2013-07-04 |
| CN103184053B (zh) | 2015-03-11 |
| EP2799516A4 (en) | 2015-07-29 |
| EP2799516A1 (en) | 2014-11-05 |
| JP2018070889A (ja) | 2018-05-10 |
| US20130342775A1 (en) | 2013-12-26 |
| CN103184053A (zh) | 2013-07-03 |
| EP2799516B1 (en) | 2019-02-20 |
| US9175220B2 (en) | 2015-11-03 |
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