JP6217988B2 - 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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- JP6217988B2 JP6217988B2 JP2015175791A JP2015175791A JP6217988B2 JP 6217988 B2 JP6217988 B2 JP 6217988B2 JP 2015175791 A JP2015175791 A JP 2015175791A JP 2015175791 A JP2015175791 A JP 2015175791A JP 6217988 B2 JP6217988 B2 JP 6217988B2
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 105
- 239000000203 mixture Substances 0.000 title claims description 77
- 239000004988 Nematic liquid crystal Substances 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 210000004027 cell Anatomy 0.000 description 21
- 230000000704 physical effect Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 7
- 101100274575 Caenorhabditis elegans clh-3 gene Proteins 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- -1 2,3-difluorophenylene skeleton Chemical group 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 3
- 101100496114 Caenorhabditis elegans clc-2 gene Proteins 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical class CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007547 defect 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- 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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- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
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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
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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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- C09K19/42—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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- 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
- 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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- 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
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
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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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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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
- C09K19/08—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)
- C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene
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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
- G02F1/137—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
- 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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- Chemical & Material Sciences (AREA)
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Description
第二成分として、一般式(II)
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−H)で表される化合物中、一般式(II−A)、一般式(II−B)、一般式(II−C)、一般式(II−E)、一般式(II−F)、一般式(II−G)が更に好ましい。
本願発明の液晶組成物は、一般式(I)で表される化合物、一般式(II)で表される化合物、及び一般式(III−A)から一般式(III−J)で表される化合物群から選ばれる化合物を同時に含有することが好ましく、一般式(I)、一般式(II)及び一般式(III−A)を同時に含有することが更に好ましい。
更には、化合物中のR41及びR42はお互い独立して、式(R−1)又は(R−2)であることが好ましく、X1からX12はそれぞれ独立してフッ素原子、水素原子又はメチル基であることが好ましく、S1及びS2はお互い独立して炭素原子数1〜4のアルキレン基、アルコキシレン基又は単結合であることが好ましく、S1及びS2はそれぞれ単結合であることがより好ましい。
上述の重合性化合物を含有した液晶組成物は、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。
本発明の液晶組成物を用いた液晶表示素子は高速応答と表示不良の抑制を両立させた有用なものであり、特に、アクティブマトリックス駆動用液晶表示素子に有用であり、VAモード、PSVAモード、PSAモード、IPSモード又はECBモード用に適用できる。
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)
(実施例1)
以下に、調製した液晶組成物とその物性値を示す。
(比較例1)
以下に、調製した液晶組成物とその物性値を示す。
(比較例2)
比較例1では式(I)で表される化合物を使用しない液晶組成物の例を示したが、一般式(II)で表される化合物を使用しない液晶組成物を調製した。
更に、実施例1、比較例1および比較例2を低温保存試験したところ、−30℃及び−20℃で実施例1はネマチック状態を2週間維持したのに対し、比較例1および比較例2は1週間しかネマチック状態を維持せず、2週目には析出が確認された。このことから、実施例1は広い温度範囲でネマチック状態を維持し、使用するにあたり非常に実用的な液晶組成物であることが確認された。
(実施例2)
以下に、調製した液晶組成物とその物性値を示す。
(実施例3)
以下に、調製した液晶組成物とその物性値を示す。
(実施例4)
以下に、調製した液晶組成物とその物性値を示す。
(実施例5)
実施例1に示すネマチック液晶組成物 99.7%に対して、式(IV−a)
この重合性液晶組成物は−30℃及び−20℃でネマチック状態を2週間維持した。このことから、広い温度範囲でネマチック状態を維持し、使用するにあたり非常に実用的な液晶組成物であることが確認された。
(実施例6)
実施例2に示すネマチック液晶組成物 99.7%に対して、式(IV−b)
この重合性液晶組成物は−30℃及び−20℃でネマチック状態を2週間維持した。このことから、広い温度範囲でネマチック状態を維持し、使用するにあたり非常に実用的な液晶組成物であることが確認された。
(実施例7)
実施例2に示すネマチック液晶組成物 99.7%に対して、式(IV−c)
この重合性液晶組成物は−30℃及び−20℃でネマチック状態を2週間維持した。このことから、広い温度範囲でネマチック状態を維持し、使用するにあたり非常に実用的な液晶組成物であることが確認された。
(実施例8)
実施例2に示すネマチック液晶組成物 99.7%に対して、式(IV−d)
この重合性液晶組成物は−30℃及び−20℃でネマチック状態を2週間維持した。このことから、広い温度範囲でネマチック状態を維持し、使用するにあたり非常に実用的な液晶組成物であることが確認された。
Claims (5)
- 第一成分として、一般式(I)
第二成分として、一般式(II−E)
第三成分として、一般式(III−A)から一般式(III−J)
以下の3つの化合物を含有し、
- 第一成分として、一般式(I)
第二成分として、一般式(II−A)
第三成分として、更に、一般式(III−A)から一般式(III−J)
- 請求項1〜2のいずれか1項に記載の液晶組成物を用いた液晶表示素子。
- 請求項1〜2のいずれか1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1〜2のいずれか1項に記載の液晶組成物を用いたVAモード、PSAモード、PSVAモード、IPSモード又はECBモード用液晶表示素子。
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KR20160003898A (ko) | 2016-01-11 |
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