JP6120122B2 - 負の誘電異方性液晶素子 - Google Patents
負の誘電異方性液晶素子 Download PDFInfo
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- JP6120122B2 JP6120122B2 JP2016556349A JP2016556349A JP6120122B2 JP 6120122 B2 JP6120122 B2 JP 6120122B2 JP 2016556349 A JP2016556349 A JP 2016556349A JP 2016556349 A JP2016556349 A JP 2016556349A JP 6120122 B2 JP6120122 B2 JP 6120122B2
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- liquid crystal
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- -1 tetrahydropyran-2,5-diyl group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 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 claims description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 239000000178 monomer Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 6
- 0 *C(CC1)CCC1c(cc(CCC(*)O1)c1c1F)c1F Chemical compound *C(CC1)CCC1c(cc(CCC(*)O1)c1c1F)c1F 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical class C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
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- Liquid Crystal (AREA)
Description
しかし、VAディスプレイの電気光学特性の十分な最適化は今までに入手可能な液晶媒体を用いてもまだ不可能である。広い動作温度範囲、低温での高速応答性、中間調応答速度、高コントラスト、広い視野角、低い閾値電圧と高い抵抗値を有し、重合可能な液晶性化合物を重合させた後も残存モノマーが少なく高い電圧保持率を示す、ディスプレイに対する要求が引き続き存在する。
三又は四の環構造を有し、Δεが負であって、その絶対値が1以上の液晶化合物、
二、三又は四の環構造を有しΔεの絶対値が1以下である液晶化合物、
及び重合性化合物の重合物を含有し、
これに使用する液晶組成物中の三又は四の環構造を有し、Δεが負であって、その絶対値が1以上の液晶化合物、二、三又は四の環構造を有しΔεの絶対値が1以下である液晶化合物及び重合前の重合性化合物の合計の含有量が液晶組成物及び重合前の重合性化合物の合計の含有量の95%以上であり、
該三又は四の環構造を有し、Δεが負であって、絶対値が1以上の液晶化合物として一般式(1)
一般式(3)の好ましい例は
一般式(4)の好ましい例は
一般式(6)はまた、(6)−1、(6)−2で表わされる重合性化合物であることもできる。
該1,4-フェニレン基、1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基、2,6-ナフチレン基、フェナントレン-2,7-ジイル基、9,10-ジヒドロフェナントレン-2,7-ジイル基、1,2,3,4,4a,9,10a-オクタヒドロフェナントレン2,7-ジイル基及びフルオレン2,7-ジイル基は置換基として1個以上のF、Cl、CF3、OCF3、シアノ基、炭素原子数1〜8のアルキル基、アルコキシ基、アルカノイル基、アルカノイルオキシ基、炭素原子数2〜8のアルケニル基、アルケニルオキシ基、アルケノイル基又はアルケノイルオキシ基を有していても良く、Y1及びY2はそれぞれ独立して−COO−、−OCO−、−CH2 CH2−、−OCH2−、−CH2O−、−CH=CH−、−C≡C−、−CH=CHCOO−、−OCOCH=CH−、−CH2CH2COO−、−CH2CH2OCO−、−COOCH2CH2−、−OCOCH2CH2−、−CONH−、−NHCO−又は単結合を表し、n5は0、1又は2を表す。)で表されるかまたは、一般式(6)−13で表される
また、一般式(6)におけるSp1及びSp2はそれぞれ独立してアルキレン基を表し、該アルキレン基は1つ以上のハロゲン原子又はCNにより置換されていても良く、この基中に存在する1つ又は2つ以上のCH2基はO原子が直接隣接しないように−O−、−S−、−NH−、−N(CH3)−、−CO−、−COO−、−OCO−、−OCOO−、−SCO−、−COS−又は−C≡C−により置き換えられていてもよい。
一般式(6)の好ましい例は、
一般式(6)におけるSp1、Sp2、Q1、Q2のうち少なくとも1つが単結合であるかまたは、n3+n4が3〜6である重合性化合物。
T−N:固体相又はスメクチック相-ネマチック相転移温度(℃)を液晶相下限温度とする。
Δn:25℃における屈折率異方性
η:20℃における粘性
V0:20℃におけるしきい値電圧
γ1:20℃における回転粘性係数
以上の物性値はモノマー添加前の液晶混合物の値。
VHR(重合処理後、加熱150℃,1hr):重合処理後、150℃のオーブンに1時間放置した後、自然冷却後の25℃における電圧保持率(%)
VHR(重合処理後、サンテスト,30min):重合処理後、サンテストに30分放置した後の25℃における電圧保持率(%)
ID(重合処理後):重合処理後の25℃におけるイオン密度
ID(重合処理後、加熱150℃,1hr):重合処理後、150℃のオーブンに1時間放置した後、自然冷却後の25℃におけるイオン密度
ID(重合処理後、サンテスト,30min):重合処理後、サンテストに30分放置した後の25℃におけるイオン密度
(なお、電圧保持率の測定条件は、印加電圧5V、フレーム時間16.5msec、パルス幅62μsecである。イオン密度の測定条件は印加電圧20V、0.05Hz三角波、R Sense5×106Ω、ゲイン100である。サンテストは株式会社東洋精機SUNTEST CPS+を使用。いずれも液晶組成物を注入したVAモードセル(セル厚3.5μm、配向膜RN−1517)に紫外線を600秒間照射(3.0J/cm2)し、重合処理を行ったものを使用した。)
−2− −CH2CH2−
−1O− −CH2O−
−O1− −OCH2−
−On− −OCnH2n+1
ndm− CnH2n+1−CH=CH−(CH2)m−1−
母体20−113は下記の化合物を混合したものを使用した。
Claims (16)
- 透明電極と配向膜が形成された一対の基板間に液晶組成物を配置し、該液晶組成物が、
一般式(1)で表される化合物、
二、三又は四の環構造を有しΔεの絶対値が1以下である液晶化合物、
及び重合性化合物の重合物を含有し、
これに使用する液晶組成物中の一般式(1)で表される化合物、二、三又は四の環構造を有しΔεの絶対値が1以下である液晶化合物及び重合前の重合性化合物の合計の含有量が液晶組成物及び重合前の重合性化合物の合計の含有量の95%以上であり、
さらに一般式(2)〜(4)で表される化合物を1種または2種以上含有するが、
一般式(2)として一般式(2)−1〜(2)−10で表される化合物を1種または2種以上含有する液晶素子。
- 一般式(5)におけるR1及び又はR2がアルケニル又はアルケニルオキシ基である化合物を1種または2種以上含有する液晶組成物を使用した請求項2〜4のいずれか1項に記載の液晶素子。
- 請求項1に記載の重合性化合物が一般式(6)
で表される重合性化合物であることを特徴とする請求項1〜5いずれか1項に記載の液晶素子。 - 重合性化合物一般式(6)におけるMGが
該1,4-フェニレン基、1,2,3,4-テトラヒドロナフタレン-2,6-ジイル基、2,6-ナフチレン基、フェナントレン-2,7-ジイル基、9,10-ジヒドロフェナントレン-2,7-ジイル基、1,2,3,4,4a,9,10a-オクタヒドロフェナントレン2,7-ジイル基及びフルオレン2,7-ジイル基は置換基として1個以上のF、Cl、CF3、OCF3、シアノ基、炭素原子数1〜8のアルキル基、アルコキシ基、アルカノイル基、アルカノイルオキシ基、炭素原子数2〜8のアルケニル基、アルケニルオキシ基、アルケノイル基又はアルケノイルオキシ基を有していても良く、Y1及びY2はそれぞれ独立して−COO−、−OCO−、−CH2 CH2−、−OCH2−、−CH2O−、−CH=CH−、−C≡C−、−CH=CHCOO−、−OCOCH=CH−、−CH2CH2COO−、−CH2CH2OCO−、−COOCH2CH2−、−OCOCH2CH2−、−CONH−、−NHCO−又は単結合を表し、n5は0、1又は2を表す。)
で表される重合性化合物であることを特徴とする請求項6に記載の液晶素子。 - 重合性化合物一般式(6)におけるSp1、Sp2、Q1及びQ2のうち少なくとも1つが単結合である重合性化合物を1種または2種以上含有する液晶組成物を使用した請求項6〜9いずれか1項に記載の液晶素子。
- 請求項1〜10のいずれか1項に記載の液晶組成物が開始剤を実質的に含まない液晶組成物を使用した請求項1記載の液晶素子。
- 重合性化合物を0.1〜2.0重量%含有する液晶組成物を使用した請求項1〜11いずれか1項に記載の液晶素子。
- 請求項1〜11のいずれか1項に記載の液晶素子を用いたことを特徴とする液晶表示装置。
- 透明電極にアクティブ素子が設けられたことを特徴とする請求項13に記載の液晶表示装置。
- VAモードの駆動表示を特徴とする請求項13又は14に記載の液晶表示装置。
- 請求項1〜12のいずれか1項に記載の液晶組成物。
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