JP5565542B1 - ネマチック液晶組成物及びこれを用いた液晶表示素子 - Google Patents
ネマチック液晶組成物及びこれを用いた液晶表示素子 Download PDFInfo
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- JP5565542B1 JP5565542B1 JP2014510323A JP2014510323A JP5565542B1 JP 5565542 B1 JP5565542 B1 JP 5565542B1 JP 2014510323 A JP2014510323 A JP 2014510323A JP 2014510323 A JP2014510323 A JP 2014510323A JP 5565542 B1 JP5565542 B1 JP 5565542B1
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- liquid crystal
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- crystal composition
- carbon atoms
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 159
- 239000000203 mixture Substances 0.000 title claims abstract description 110
- 239000004988 Nematic liquid crystal Substances 0.000 title claims abstract description 15
- 239000011159 matrix material Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 230000007547 defect Effects 0.000 abstract description 4
- 239000012769 display material Substances 0.000 abstract description 2
- 230000001629 suppression Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 22
- 230000000704 physical effect Effects 0.000 description 17
- 239000000758 substrate Substances 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 10
- 206010047571 Visual impairment Diseases 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 230000005684 electric field Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 101100208473 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lcm-2 gene Proteins 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- -1 benzoin ethers Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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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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- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
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- C09K2019/0444—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
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- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/124—Ph-Ph-Ph-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K2019/3075—Cy-COO-Ph
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- 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
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- C09K2019/548—Macromolecular compounds stabilizing the alignment; Polymer stabilized alignment
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- 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
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
Abstract
Description
第一成分として、一般式(I−1)から一般式(I−3)
第二成分として、一般式(II−a)から一般式(II−e)
一般式(I−1)から一般式(I−3)で表される化合物中、液晶組成物に対する溶解性を重視した場合は一般式(I−1)で表される化合物が好ましく、液晶組成物の熱や光に対する安定性を重視した場合は一般式(I−3)で表される化合物が好ましい。
本願発明の液晶組成物において、一般式(I−1)から一般式(I−3)で表される化合物を1種又は2種を含有するが好ましく、1種から5種含有することが更に好ましく、その含有量は0.001から1質量%であることが好ましく、0.001から0.1質量%が更に好ましく、0.001から0.05質量%が特に好ましい。
本願発明の液晶組成物は、更に、第三成分として、第三成分として、一般式(III)
一般式(III)で表される化合物群は1種〜8種含有することが好ましく、1種〜5種含有することが特に好ましく、その含有量は3から50質量%であるが、5から40質量%であることが好ましい。
(式中、X51及びX52はそれぞれ独立して、水素原子又はメチル基を表し、
Sp1及びSp2はそれぞれ独立して、単結合、炭素原子数1〜8のアルキレン基又は−O−(CH2)s−
(式中、sは2から7の整数を表し、酸素原子は芳香環に結合するものとする。)を表し、
Z51は−OCH2−、−CH2O−、−COO−、−OCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CY1=CY2−(式中、Y1及びY2はそれぞれ独立して、フッ素原子又は水素原子を表す。)、−C≡C−又は単結合を表し、
M51は1,4−フェニレン基、トランスー1,4−シクロヘキシレン基又は単結合を表し、式中の全ての1,4−フェニレン基は、任意の水素原子がフッ素原子により置換されていても良い。)で表される二官能モノマーが好ましい。
これらの骨格を含む重合性化合物は重合後の配向規制力がPSA型液晶表示素子に最適であり、良好な配向状態が得られることから、表示ムラが抑制されるか、又は、全く発生しない。
本発明の液晶組成物にモノマーを添加する場合において、重合開始剤が存在しない場合でも重合は進行するが、重合を促進するために重合開始剤を含有していてもよい。重合開始剤としては、ベンゾインエーテル類、ベンゾフェノン類、アセトフェノン類、ベンジルケタール類、アシルフォスフィンオキサイド類等が挙げられる。
Δn :25℃における屈折率異方性
Δε :25℃における誘電率異方性
η :20℃における粘度(mPa・s)
γ1 :25℃における回転粘性(mPa・s)
VHR:周波数60Hz,印加電圧1Vの条件下で60℃における電圧保持率(%)
焼き付き:
液晶表示素子の焼き付き評価は、表示エリア内に所定の固定パターンを1000時間表示させた後に、全画面均一な表示を行ったときの固定パターンの残像のレベルを目視にて以下の4段階評価で行った。
○残像ごく僅かに有るも許容できるレベル
△残像有り許容できないレベル
×残像有りかなり劣悪
滴下痕 :
液晶表示装置の滴下痕の評価は、全面黒表示した場合における白く浮かび上がる滴下痕を目視にて以下の4段階評価で行った。
○残像ごく僅かに有るも許容できるレベル
△残像有り許容できないレベル
×残像有りかなり劣悪
尚、実施例において化合物の記載について以下の略号を用いる。
(環構造)
以下に示す液晶組成物LC−1を調製した。
実施例1に記載の式(I−1−1)で表される化合物を添加していない液晶組成物LC−1の初期のVHRは99.5%であったのに対し、150℃で1時間の高温放置後のVHRは、87.2%と初期に対して大きく低下した。
また、液晶組成物LC−1を用いてVA液晶表示素子を作製し、前述の方法により焼き付き及び滴下痕の測定したところ、以下に示すように実施例1と比べて劣る結果を示した。
一般式(II)で表される化合物を含有しない、以下に示される液晶組成物LC−2を調製した。
また、液晶組成物LCM−Aを用いてIPS液晶表示素子を作製し、前述の方法により焼き付き及び滴下痕の測定したところ、以下に示すように実施例1に比べて劣る結果を示した。
次に示す液晶組成物LC−2〜LC−4を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−2〜LCM−4の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−2〜LCM−4を用いて作製したIPS液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
次に示す液晶組成物LC−5〜LC−7を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−5〜LCM−7の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−5〜LCM−7を用いて作製したIPS液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
次に示す液晶組成物LC−8〜LC−10を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−8〜LCM−10の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−8〜LCM−10を用いて作製したIPS液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
次に示す液晶組成物LC−11〜LC−13を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−11〜LCM−13の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−11〜LCM−13を用いて作製したIPS液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
次に示す液晶組成物LC−14〜LC−16を調製し、その物性値を測定した。この結果を次の表に示す。
液晶組成物LCM−14〜LCM−16の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−14〜LCM−16を用いて作製したIPS液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
上記の液晶組成物LC−14からLC−16の各々99.97%に対して、式(I−2−1)
液晶組成物LCM−17〜LCM−19の初期のVHR及び150℃で1時間の高温放置後のVHRはほとんど変化がなかった。また、液晶組成物LCM−17〜LCM−19を用いて作製したVA液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように優れた結果を示した。
実施例1に示すネマチック液晶組成物LCM−1 99.7%に対して、式(IV−b)
Claims (8)
- 第一成分として、一般式(I−1)から一般式(I−3)
第二成分として、一般式(II−a)から一般式(II−e)
第三成分として、一般式(III)
で表される化合物を一種又は二種以上含有し、
25℃における誘電率異方性(Δε)が+3.5以上であることを特徴とするネマチック液晶組成物。 - 一般式(I−1)から一般式(I−3)で表される化合物からなる群から選ばれる化合物の含有量が0.001質量%から1質量%であり、一般式(II)で表される化合物の含有量が10質量%から70質量%である請求項1から3のいずれか一項に記載のネマチック液晶組成物。
- 一般式(V)
Sp1及びSp2はそれぞれ独立して、単結合、炭素原子数1〜8のアルキレン基又は−O−(CH2)s−
(式中、sは2から7の整数を表し、酸素原子は芳香環に結合するものとする。)を表し、
Z51は−OCH2−、−CH2O−、−COO−、−OCO−、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CH=CH−COO−、−CH=CH−OCO−、−COO−CH=CH−、−OCO−CH=CH−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−、−COO−CH2−、−OCO−CH2−、−CH2−COO−、−CH2−OCO−、−CY1=CY2−(式中、Y1及びY2はそれぞれ独立して、フッ素原子又は水素原子を表す。)、−C≡C−又は単結合を表し、
M51は1,4−フェニレン基、トランス−1,4−シクロヘキシレン基又は単結合を表し、式中の全ての1,4−フェニレン基は、任意の水素原子がフッ素原子により置換されていても良い。)で表される重合性化合物を含有する請求項1から4のいずれか一項に記載のネマチック液晶組成物。 - 請求項1から5のいずれか一項に記載の液晶組成物を用いたアクティブマトリックス駆動用液晶表示素子。
- 請求項1から5のいずれか一項に記載の液晶組成物を用いたIPSモード、FFSモード又はVA−IPSモード用液晶表示素子。
- 請求項5に記載の重合性化合物を含有するネマチック液晶組成物を用い、電圧印加下あるいは電圧無印加下で該液晶組成物中に含有する重合性化合物を重合させて作製した高分子安定化モード液晶表示素子。
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JPH09124529A (ja) * | 1995-10-20 | 1997-05-13 | Merck Patent Gmbh | 2,6−ジ−tert−ブチルフェノール化合物 |
DE10117224A1 (de) * | 2000-04-19 | 2002-02-21 | Merck Patent Gmbh | Verfahren zur Stabilisierung von Halogenaromaten |
JP2006502205A (ja) * | 2002-10-07 | 2006-01-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | キラルなフェノール誘導体、それらを含む液晶媒体 |
JP2011516628A (ja) * | 2008-03-10 | 2011-05-26 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体 |
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JPH09124529A (ja) * | 1995-10-20 | 1997-05-13 | Merck Patent Gmbh | 2,6−ジ−tert−ブチルフェノール化合物 |
DE10117224A1 (de) * | 2000-04-19 | 2002-02-21 | Merck Patent Gmbh | Verfahren zur Stabilisierung von Halogenaromaten |
JP2006502205A (ja) * | 2002-10-07 | 2006-01-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | キラルなフェノール誘導体、それらを含む液晶媒体 |
JP2011516628A (ja) * | 2008-03-10 | 2011-05-26 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 液晶媒体 |
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