TWI553040B - Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components - Google Patents

Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components Download PDF

Info

Publication number: TWI553040B
Authority: TW; Taiwan
Prior art keywords: liquid crystal; group; carbon atoms; crystal alignment; alignment agent
Prior art date: 2011-05-27

Application number

TW101118909A

Other languages

English (en)

Chinese (zh)

Other versions

TW201313786A (zh

Inventor

Kenji Sakamoto

Rie Gunji

Jun Hashimoto

Yuuki Takayama

Daisuke Sakuma

Shogo Himori

Koji Hiraga

Kenichi Motoyama

Original Assignee

Nissan Chemical Ind Ltd

Priority date (The priority date 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 date listed.)

2011-05-27

Filing date

2012-05-25

Publication date

2016-10-11

2012-05-25 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2013-04-01 Publication of TW201313786A publication Critical patent/TW201313786A/zh

2016-10-11 Application granted granted Critical

2016-10-11 Publication of TWI553040B publication Critical patent/TWI553040B/zh

Links

239000004973 liquid crystal related substance Substances 0.000 title claims description 243
239000003795 chemical substances by application Substances 0.000 title claims description 102
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title 1
229910052710 silicon Inorganic materials 0.000 title 1
239000010703 silicon Substances 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims description 115
125000000217 alkyl group Chemical group 0.000 claims description 61
239000000758 substrate Substances 0.000 claims description 43
-1 acryl group Chemical group 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 28
210000002858 crystal cell Anatomy 0.000 claims description 26
229910052731 fluorine Inorganic materials 0.000 claims description 26
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 19
239000011737 fluorine Substances 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000000962 organic group Chemical group 0.000 claims description 13
238000006068 polycondensation reaction Methods 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 10
150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
238000001035 drying Methods 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
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 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000005641 methacryl group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
229920002098 polyfluorene Polymers 0.000 claims description 4
125000005504 styryl group Chemical group 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
239000000243 solution Substances 0.000 description 90
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 51
238000000034 method Methods 0.000 description 49
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125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups

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Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nonlinear Science (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Mathematical Physics (AREA)
Crystallography & Structural Chemistry (AREA)
Spectroscopy & Molecular Physics (AREA)
Liquid Crystal (AREA)
Silicon Polymers (AREA)
Macromonomer-Based Addition Polymer (AREA)

TW101118909A 2011-05-27 2012-05-25 Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components TWI553040B (zh)

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JP2011251377		2011-11-17

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JP (1)	JP6079626B2 (ja)
KR (1)	KR101883521B1 (ja)
CN (1)	CN103718091B (ja)
TW (1)	TWI553040B (ja)
WO (1)	WO2012165354A1 (ja)

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JP5678901B2 (ja) *	2012-01-25	2015-03-04	信越化学工業株式会社	硬化性樹脂組成物並びにその硬化成形品及び硬化皮膜を有する物品
JPWO2014021174A1 (ja) *	2012-07-31	2016-07-21	日産化学工業株式会社	液晶配向剤、液晶配向膜、液晶表示素子及び液晶表示素子の製造方法
KR102115015B1 (ko) *	2012-08-30	2020-05-25	닛산 가가쿠 가부시키가이샤	액정 배향 처리제 및 그것을 사용한 액정 표시 소자
KR102196273B1 (ko) *	2013-04-16	2020-12-29	닛산 가가쿠 가부시키가이샤	액정 표시 소자, 액정 배향막 및 액정 배향 처리제
CN105452262A (zh)	2013-06-06	2016-03-30	日产化学工业株式会社	烷氧基硅烷化合物、液晶取向剂、液晶取向膜和液晶表示元件
TWI490253B (zh) *	2013-07-12	2015-07-01	Daxin Materials Corp	液晶配向劑、液晶配向膜以及液晶顯示元件
CN105556381B (zh) *	2013-07-19	2019-03-15	日产化学工业株式会社	液晶表示元件、液晶取向处理剂和液晶取向膜
JP6465302B2 (ja) *	2013-08-14	2019-02-06	日産化学株式会社	液晶表示素子の製造方法
CN105899615B (zh) *	2013-10-10	2020-12-01	日产化学工业株式会社	组合物、液晶取向处理剂、液晶取向膜和液晶表示元件
CN107533258B (zh) *	2015-03-02	2020-11-06	日产化学工业株式会社	液晶表示元件
CN105087021B (zh) *	2015-06-18	2017-11-17	深圳市华星光电技术有限公司	一种液晶垂直取向剂、液晶显示元件以及液晶显示元件的制备方法
KR102723606B1 (ko) *	2016-02-26	2024-10-29	닛산 가가쿠 가부시키가이샤	액정 표시 소자
CN110109293A (zh) *	2019-04-04	2019-08-09	深圳市华星光电技术有限公司	液晶无机配向薄膜的制造方法

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- 2012-05-25 CN CN201280036983.3A patent/CN103718091B/zh active Active
- 2012-05-25 TW TW101118909A patent/TWI553040B/zh active
- 2012-05-25 KR KR1020137034392A patent/KR101883521B1/ko active Active

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Also Published As

Publication number	Publication date
CN103718091A (zh)	2014-04-09
CN103718091B (zh)	2016-08-31
KR101883521B1 (ko)	2018-07-30
WO2012165354A1 (ja)	2012-12-06
JPWO2012165354A1 (ja)	2015-02-23
TW201313786A (zh)	2013-04-01
JP6079626B2 (ja)	2017-02-15
KR20140035959A (ko)	2014-03-24

Publication	Publication Date	Title
TWI553040B (zh)	2016-10-11	Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components
TWI483969B (zh)	2015-05-11	Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components
TWI475073B (zh)	2015-03-01	Silicone liquid crystal aligning agent and liquid crystal alignment film
TWI452066B (zh)	2014-09-11	Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components
TWI620753B (zh)	2018-04-11	Alkoxysilane compound, liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element
TWI570159B (zh)	2017-02-11	Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components
TWI515234B (zh)	2016-01-01	Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element
JP6459513B2 (ja)	2019-01-30	液晶配向剤、液晶配向膜及び液晶表示素子
TWI490253B (zh)	2015-07-01	液晶配向劑、液晶配向膜以及液晶顯示元件
TWI534511B (zh)	2016-05-21	Liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display device, and liquid crystal display device manufacturing method
TWI572676B (zh)	2017-03-01	Silicon liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display components