JPWO2014136315A1 - 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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- JPWO2014136315A1 JPWO2014136315A1 JP2014506389A JP2014506389A JPWO2014136315A1 JP WO2014136315 A1 JPWO2014136315 A1 JP WO2014136315A1 JP 2014506389 A JP2014506389 A JP 2014506389A JP 2014506389 A JP2014506389 A JP 2014506389A JP WO2014136315 A1 JPWO2014136315 A1 JP WO2014136315A1
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- 239000004988 Nematic liquid crystal Substances 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 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 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000004020 conductor Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
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- 101100208473 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lcm-2 gene Proteins 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 4
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
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- 239000002245 particle Substances 0.000 description 3
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- 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 2
- HVTJQICZTQZLSK-UHFFFAOYSA-N CC(C(Oc(cc1)ccc1-c(cc1)ccc1OC(C(C)=C)=O)=O)=C Chemical compound CC(C(Oc(cc1)ccc1-c(cc1)ccc1OC(C(C)=C)=O)=O)=C HVTJQICZTQZLSK-UHFFFAOYSA-N 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- -1 substituted Chemical class 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 0 CC(C)(*)C(CC1)CCC1C(C)(C)c(cc1)c(*)c(*2)c1-c1c2c(*)c(*)cc1 Chemical compound CC(C)(*)C(CC1)CCC1C(C)(C)c(cc1)c(*)c(*2)c1-c1c2c(*)c(*)cc1 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004593 Epoxy 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
- 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
- 235000010290 biphenyl Nutrition 0.000 description 1
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- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 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
- 239000012769 display material Substances 0.000 description 1
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- 238000004070 electrodeposition Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000011737 fluorine Substances 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
- 230000001105 regulatory effect Effects 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
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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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/06—Non-steroidal liquid crystal compounds
- 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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- 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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- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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- 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
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Abstract
Description
第一成分として、一般式(I)
第二成分として、一般式(II)
本願発明の液晶組成物において、一般式(I)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。
第二成分として使用する一般式(II)
一般式(II−a)から一般式(II−f)で表される化合物中、一般式(II−a)、一般式(II−c)及び一般式(II−d)が更に好ましい。
一般式(III)で表される化合物において、R31〜R32はお互い独立しては炭素原子数1から10のアルキル基、アルコキシ基、又は炭素原子数2から10のアルケニル基を表す。M31はトランス−1,4−シクロへキシレン基を表す。L31は単結合、−CH2CH2−又は、−CH2O−を表す。n31は0又は1を表す。
本願発明の液晶組成物は、また更に、一般式(IV−a)から一般式(IV−d)
(式中、R41〜R48はお互い独立しては炭素原子数1から10のアルキル基、アルコキシ基又は炭素原子数2から10のアルケニル基を表す。)
本願発明では一般式(IV−a)から一般式(IV−d)で表される化合物群から選ばれる化合物を含有することができるが、1種〜10種含有することが好ましく、1種〜8種含有することが特に好ましく、その含有量は5から80質量%であることが好ましく、10から70質量%であることが更に好ましく、20から60質量%であることが特に好ましい。
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 :20℃における屈折率異方性
Δε :20℃における誘電率異方性
η :20℃における粘度(mPa・s)
γ1 :20℃における回転粘性(mPa・s)
VHR:周波数60Hz,印加電圧5Vの条件下で50℃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1200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。
(側鎖)
-n -CnH2n+1 炭素原子数nの直鎖状アルキル基
n- CnH2n+1- 炭素原子数nの直鎖状アルキル基
-On -OCnH2n+1 炭素原子数nの直鎖状アルコキシ基
-V -CH=CH2
V- CH2=CH-
-V1 -CH=CH-CH3
-2V1 -CH2-CH2-CH=CH-CH3
V2- CH2=CH-CH2-CH2-
(環構造)
以下に示される液晶組成物LC−1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。
(比較例1)
実施例1に記載の式(I−c−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98.5%であったのに対し、150℃で1時間の高温放置後のVHRは、86.7%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−Aを調製し、物性値を測定した。
また、液晶組成物LCM−2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に比べて劣る結果を示した。
(実施例2から実施例4)
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−3〜LCM−5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−3〜LCM−5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。
次に示す液晶組成物LC−5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−6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−6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に記載の液晶組成物LC−1及び実施例5に記載のLC−5の各々99.97%に対して、式(I−a−1)
液晶組成物LCM−7及びLCM−8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−7及びLCM−8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に記載の液晶組成物LC−1 99.97%に対して、式(I−b−1)
液晶組成物LCM−9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−9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に記載の液晶組成物LCM−1 99.7%に対して、
比較例1で使用した液晶組成物LC−1及び比較例2で使用したLCM−2の各々99.7%に対して、
本液晶表示素子の焼き付き及び滴下痕の測定したところ、以下に示すように実施例9に比べて劣る結果を示した。
実施例2〜4に記載の液晶組成物LCM−3〜5の各々99.7%に対して、
(実施例14から実施例4)
次に示す液晶組成物LC−6〜LC−29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。
Claims (8)
- 第一成分として、一般式(I)
第二成分として、一般式(II)
- 一般式(I)において、R1が炭素原子数1から10の直鎖アルキル基又は分岐炭アルキル基を表し、M1はトランス−1,4−シクロへキシレン基又は1,4−フェニレン基を表す請求項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(I)で表さ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5質量%から30質量%である請求項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。
- 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5のいずれか一項に記載のネマチック液晶組成物。 - 透明導電性材料からなる共通電極を具備した第一の基板と、透明導電性材料からなる画素電極と各画素に具備した画素電極を制御する薄膜トランジスターを具備した第二の基板と、前記第一の基板と第二の基板間に挟持された液晶組成物を有し、該液晶組成物中の液晶分子の電圧無印加時の配向が前記基板に対して略垂直である液晶表示素子であって、該液晶組成物として請求項1から6のいずれか一項に記載のネマチック液晶組成物を用いた液晶表示素子。
- 請求項6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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KR102117336B1 (ko) | 2020-06-01 |
JP2019014893A (ja) | 2019-01-31 |
KR20190107732A (ko) | 2019-09-20 |
KR20150143859A (ko) | 2015-12-23 |
US10316251B2 (en) | 2019-06-11 |
KR20140127364A (ko) | 2014-11-03 |
JP2014196474A (ja) | 2014-10-16 |
US20160009995A1 (en) | 2016-01-14 |
JP6394945B2 (ja) | 2018-09-26 |
JP6519973B2 (ja) | 2019-05-29 |
JP2014208842A (ja) | 2014-11-06 |
US20170349829A1 (en) | 2017-12-07 |
KR102017601B1 (ko) | 2019-09-09 |
JP5585745B1 (ja) | 2014-09-10 |
CN104284962B (zh) | 2016-02-24 |
JP6760340B2 (ja) | 2020-09-23 |
WO2014136315A1 (ja) | 2014-09-12 |
TWI488949B (zh) | 2015-06-21 |
CN104284962A (zh) | 2015-01-14 |
TW201437337A (zh) | 2014-10-01 |
US9745513B2 (en) | 2017-08-29 |
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