JP5709761B2 - 重合性化合物を含有する液晶組成物及び該液晶組成物を用いた液晶表示素子 - Google Patents
重合性化合物を含有する液晶組成物及び該液晶組成物を用いた液晶表示素子 Download PDFInfo
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- JP5709761B2 JP5709761B2 JP2011541855A JP2011541855A JP5709761B2 JP 5709761 B2 JP5709761 B2 JP 5709761B2 JP 2011541855 A JP2011541855 A JP 2011541855A JP 2011541855 A JP2011541855 A JP 2011541855A JP 5709761 B2 JP5709761 B2 JP 5709761B2
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- 229910052794 bromium Inorganic materials 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
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000010891 electric arc Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical class ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- 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
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- 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
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- C09K2019/0448—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 end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- 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
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- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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- G02F1/13712—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 the liquid crystal having negative dielectric anisotropy
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- 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
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- G02F2202/00—Materials and properties
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- G02F2202/022—Materials and properties organic material polymeric
Description
M1、M2及びM3は、それぞれ独立に、水素原子又はメチル基を表し、
Z1及びZ2は、それぞれ独立に、直接結合、−L1−、−L1O−、−L1O−CO−、−L1CO−O−又は−L1O−CO−O−であり、Z6は、直接結合、−L2−、−OL2−、−O−COL2−、−CO−OL2−又は−O−CO−OL2−であり、Z1、Z2及びZ6の少なくともいずれか一つは直接結合ではなく、L1及びL2は、それぞれ独立に、分岐を有してもよい炭素原子数1〜10のアルキレン基を表し、該アルキレン基は酸素原子で1〜3回中断されてもよく、該中断は酸素原子が隣り合わず、
Z3、Z4及びZ 5 は、エステル結合を表し、
p、q及びrは、それぞれ独立に0又は1であり、かつ1≦p+q+r≦3である。)
本発明の効果をより確実に奏させる上で、環C1〜環C4は、環C1がベンゼン−1,2,4−トリイル基であり、環C2、C3及びC4は、それぞれ独立に、上記置換基で置換されていてもよい1,4−フェニレン基又はナフタレン−2,6−ジイル基であることが好ましい。
また、上記一般式(I)において、p+q+rが1又は2の重合性化合物;M1、M2及びM3が全てメチル基である重合性化合物を用いると、信頼性が特に優れるため、より好ましい。
Y1、Y2及びY3は、それぞれ独立に、直接結合、−CH2−CH2−、−CF2−CF2−、−CH=CH−、−CF=CF−、−CH2−O−、−O−CH2−、−CF2−O−、−O−CF2−、−CH2−S−、−S−CH2−、−CF2−S−、−S−CF2−、−O−CF2−C2H4−、−C2H4−CF2−O−、−CO−O−、−O−CO−、−CH2−CH2−CO−O−、−O−CO−CH2−CH2−又は−C≡C−を表し、
R3及びR4は、それぞれ独立に、炭素原子数1〜6のアルキル基又は炭素原子数2〜6のアルケニル基を表し、
j、k及びmは、それぞれ独立に0又は1であり、かつj+k+m≧1であり、nは0又は1である。)
X1及びX2は、それぞれ独立に、直接結合、−CH2−CH2−、−CF2−CF2−、−CH=CH−、−CF=CF−、−CH2−O−、−O−CH2−、−CF2−O−、−O−CF2−又は−C≡C−を表し、
R1及びR2は、それぞれ独立に、炭素原子数1〜6のアルキル基又は炭素原子数2〜6のアルケニル基を表し、
g及びhは、それぞれ独立に、0又は1である。)
下記実施例1−1〜1−6及び比較例1−1では、参考例で得られたネマチック液晶組成物、及び合成例で得られた本発明に係る重合性化合物又は比較用重合性化合物を用いて液晶組成物を作製し、該液晶組成物の各種特性を比較評価した。尚、比較例1−2では、重合性化合物を用いず、参考例で得られたネマチック液晶組成物そのものの特性を評価した。
下記実施例2−1〜2−5及び比較例2−1〜2−3では、本発明に係る重合性化合物又は比較重合性化合物の反応性を比較評価した。
下記実施例3−1〜3−2及び比較例3−1では、本発明に係る重合性化合物又は比較用重合性化合物を、本発明に係るネマチック液晶組成物に配合して液晶組成物を作製し、該液晶組成物を用いて電気光学表示素子を作製し、得られた電気光学表示素子の配向安定性(VTシフト)を比較評価した。
液晶化合物No.1〜No.10を下記の配合比(合計100質量部)に従って混合して、液晶組成物No.1を作成した。なお、液晶化合物No.1〜No.4は上記一般式(IV)に該当する化合物であり、液晶化合物No.5〜No.10は上記一般式(II)に該当する化合物である。
下記反応式1に従い、以下の手順により、重合性化合物No.1を合成した。
液晶組成物No.1の100質量部に対し、表3に示す重合性化合物をそれぞれ0.5質量部加え、重合性化合物を含有する液晶組成物を得た。得られた重合性化合物を含有する液晶組成物の溶解性、配向性及び電圧保持率(VHR)について、それぞれ以下の方法で評価・測定した。
重合性化合物を含まない液晶組成物として液晶組成物No.1の配向性及び電圧保持率をそれぞれ以下の方法で評価・測定した。
得られた液晶組成物について、重合性化合物溶解後の析出物の有無を評価した。1日後に析出物の無いものを○、1日後に析出物が確認できたものを△、溶解後すぐに析出物が確認できたものを×として評価した。
得られた液晶組成物を液晶評価用テストセル(セル厚5μm、電極面積8mm×8mm、配向膜JALS2096)に注入後、注入口を封止剤にて封止した。その後、高圧水銀ランプ(1000mJ/cm2)で光を照射し、サンプルを得た。得られたサンプルについて、偏光顕微観察(クロスニコル下にて電圧OFF時の配向状態)を目視で行い、配向性を確認し、配向が良好だったものを○、配向が乱れていたものを×として評価した。
上記配向性の評価において得られたサンプルに対して、以下の装置及び条件によりVHRの測定を行った。
・装置:東陽テクニカ社製VHR−A1
・条件:パルス電圧幅60μs、フレーム周期16.7ms、波高±5V、測定温度25℃
<光照射前のサンプル>
実施例1−1で得られた重合性化合物を含有する液晶組成物をアセトニトリルに溶解し、サンプルとした。
<光照射後のサンプル>
実施例1−1で配向性評価に用いた、高圧水銀ランプ(1000mJ/cm2)で光を照射した液晶評価用テストセルを解体し、重合性液晶組成物をアセトニトリルに抽出し、サンプルとした。
得られたサンプルを液体クロマトグラフィーにて分析し、光照射前に比較した場合の光照射後における重合性化合物の残存率を評価した。その結果を〔表4〕に示す。
実施例2−1で用いた液晶組成物を下記[表4]に示す重合性化合物を含有する液晶組成物に替えた以外は実施例2−1と同様の手法で、重合性化合物の残存率を評価した。その結果を〔表4〕に示す。
液晶組成物No.1の100質量部に対し、〔表5〕に示す重合性化合物をそれぞれ0.2質量部加え、加温して溶解を確認して液晶組成物とした。室温まで冷却した該液晶組成物を液晶評価用テストセル(セル厚5μm、電極面積8mm×8mm、配向膜JALS−2096(JSR社製)、アンチパラレルラビング)に注入し、電圧印加しない状態で高圧水銀ランプ(照度40mW/cm2、光量20J/cm2)にてエネルギー線照射した。テストセルをエージングした後、電圧−透過率特性(VT特性)を測定して、その測定値を初期値とした。テストセルに4時間及び10時間連続印加した後、VT特性を測定して初期値との差(VT変化量)を調べた。VT変化量は、測定したVT特性の透過率が10%、50%、90%の電圧(V10、V50、V90)における変化量を平均して求めた。結果を〔表5〕に示す。
Claims (7)
- 誘電率異方性(Δε)が負であるネマチック液晶組成物100質量部に対し、下記一般式(I)で表される重合性化合物0.01〜3質量部を含有させてなる液晶組成物。
M1、M2及びM3は、それぞれ独立に、水素原子又はメチル基を表し、
Z1及びZ2は、それぞれ独立に、直接結合、−L1−、−L1O−、−L1O−CO−、−L1CO−O−又は−L1O−CO−O−であり、Z6は、直接結合、−L2−、−OL2−、−O−COL2−、−CO−OL2−又は−O−CO−OL2−であり、Z1、Z2及びZ6の少なくともいずれか一つは直接結合ではなく、L1及びL2は、それぞれ独立に、分岐を有してもよい炭素原子数1〜10のアルキレン基を表し、該アルキレン基は酸素原子で1〜3回中断されてもよく、該中断は酸素原子が隣り合わず、
Z3、Z4及びZ 5 は、エステル結合を表し、
p、q及びrは、それぞれ独立に0又は1であり、かつ1≦p+q+r≦3である。) - 上記一般式(I)中の環C1がベンゼン−1,2,4−トリイル基であり、環C2、C3及びC4は、それぞれ独立に、上記置換基で置換されていてもよい1,4−フェニレン基又はナフタレン−2,6−ジイル基である請求項1に記載の液晶組成物。
- 上記一般式(I)において、Z1及びZ2がZ6と違う基及び/又はL1とL2が違う基である請求項1又は2記載の液晶組成物。
- 誘電率異方性(Δε)が負である上記ネマチック液晶組成物が、下記一般式(II)で表される液晶化合物を含有するものである請求項1〜3のいずれか一項に記載の液晶組成物。
Y1、Y2及びY3は、それぞれ独立に、直接結合、−CH2−CH2−、−CF2−CF2−、−CH=CH−、−CF=CF−、−CH2−O−、−O−CH2−、−CF2−O−、−O−CF2−、−CH2−S−、−S−CH2−、−CF2−S−、−S−CF2−、−O−CF2−C2H4−、−C2H4−CF2−O−、−CO−O−、−O−CO−、−CH2−CH2−CO−O−、−O−CO−CH2−CH2−又は−C≡C−を表し、
R3及びR4は、それぞれ独立に、炭素原子数1〜6のアルキル基又は炭素原子数2〜6のアルケニル基を表し、
j、k及びmは、それぞれ独立に0又は1であり、かつj+k+m≧1であり、nは0又は1である。) - 誘電率異方性(Δε)が負である上記ネマチック液晶組成物が、さらに下記一般式(IV)で表される液晶化合物を含有するものである請求項1〜5のいずれか一項に記載の液晶組成物。
X1及びX2は、それぞれ独立に、直接結合、−CH2−CH2−、−CF2−CF2−、−CH=CH−、−CF=CF−、−CH2−O−、−O−CH2−、−CF2−O−、−O−CF2−又は−C≡C−を表し、
R1及びR2は、それぞれ独立に、炭素原子数1〜6のアルキル基又は炭素原子数2〜6のアルケニル基を表し、
g及びhは、それぞれ独立に、0又は1である。) - 請求項1〜6のいずれか一項に記載の液晶組成物を、少なくとも一方の基板上に、液晶分子に電圧を印加するための電極を備えた一対の基板で挟持した後、該液晶組成物にエネルギー線を照射して、該液晶組成物が含有する上記一般式(I)で表される重合性化合物を重合させてなる電気光学表示素子。
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