JP5776908B2 - 液晶配向剤、液晶配向膜及び液晶表示素子並びに液晶表示素子の製造方法 - Google Patents
液晶配向剤、液晶配向膜及び液晶表示素子並びに液晶表示素子の製造方法 Download PDFInfo
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- JP5776908B2 JP5776908B2 JP2012522706A JP2012522706A JP5776908B2 JP 5776908 B2 JP5776908 B2 JP 5776908B2 JP 2012522706 A JP2012522706 A JP 2012522706A JP 2012522706 A JP2012522706 A JP 2012522706A JP 5776908 B2 JP5776908 B2 JP 5776908B2
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- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- UCSBCWBHZLSFGC-UHFFFAOYSA-N tributoxysilane Chemical compound CCCCO[SiH](OCCCC)OCCCC UCSBCWBHZLSFGC-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- PMQIWLWDLURJOE-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F PMQIWLWDLURJOE-UHFFFAOYSA-N 0.000 description 1
- BPCXHCSZMTWUBW-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F BPCXHCSZMTWUBW-UHFFFAOYSA-N 0.000 description 1
- UUVZTKMMRCCGHN-UHFFFAOYSA-N triethoxy(2-phenylethenyl)silane Chemical compound CCO[Si](OCC)(OCC)C=CC1=CC=CC=C1 UUVZTKMMRCCGHN-UHFFFAOYSA-N 0.000 description 1
- VBSUMMHIJNZMRM-UHFFFAOYSA-N triethoxy(2-phenylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=C1 VBSUMMHIJNZMRM-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- HXOGQBSDPSMHJK-UHFFFAOYSA-N triethoxy(6-methylheptyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC(C)C HXOGQBSDPSMHJK-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZJEYUFMTCHLQQI-UHFFFAOYSA-N triethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OCC)(OCC)OCC)=CC=CC2=C1 ZJEYUFMTCHLQQI-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-UHFFFAOYSA-N trimethoxy(2-phenylethenyl)silane Chemical compound CO[Si](OC)(OC)C=CC1=CC=CC=C1 JRSJRHKJPOJTMS-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZSOVVFMGSCDMIF-UHFFFAOYSA-N trimethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OC)(OC)OC)=CC=CC2=C1 ZSOVVFMGSCDMIF-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- RKFOUDRIIBYXLR-UHFFFAOYSA-N trimethoxy-(1,1,2,3,3-pentafluoro-3-phenylpropyl)silane Chemical compound FC(C([Si](OC)(OC)OC)(F)F)C(C1=CC=CC=C1)(F)F RKFOUDRIIBYXLR-UHFFFAOYSA-N 0.000 description 1
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F24/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal (AREA)
- Furan Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
さらに、前記ポリシロキサンが、光反応性の側鎖を有することが好ましい。
そして、前記ポリシロキサンが、アルコキシシラン及びその縮合物から選択される少なくとも一種を重縮合して得られたものであることが好ましい。
前記アルコキシシランが、下記式(7)で表されるアルコキシシランを含んでいてもよい。
R11Si(OR12)3 (7)
(R11はフッ素原子で水素原子が置換されていてもよい、炭素数8〜30の炭化水素基であり、R12は炭素数1〜5のアルキル基を表す。)
また、前記アルコキシシランが、下記式(8)を含んでいてもよい。
R13Si(OR14)3 (8)
(R13はアクリル基、メタクリル基、ビニル基、エポキシ基、ビニロキシ基及びアクリロキシ基から選択される少なくとも一種で水素原子が置換されたアルキル基を表し、R14は炭素数1〜5のアルキル基を表す。)
本発明の重合性化合物は、上記式(1)で表される。上記式(1)において、Vは、単結合又は−R1O−で表されR1は直鎖もしくは分岐の炭素数1〜10のアルキレン基であり、好ましくは、−R1O−で表されR1は直鎖もしくは分岐の炭素数2〜6のアルキレン基である。また、Wは、単結合又は−OR2−で表されR2は直鎖もしくは分岐の炭素数1〜10のアルキレン基であり、好ましくは、−OR2−で表されR2は直鎖もしくは分岐の炭素数2〜6のアルキレン基である。なお、V及びWは同一の構造でも異なっていてもよいが、同一であると合成が容易である。
(式(9)中、R15は、水素原子、又はヘテロ原子、ハロゲン原子、アミノ基、グリシドキシ基、メルカプト基、イソシアネート基若しくはウレイド基で置換されていてもよい、炭素数1〜6の炭化水素基であり、R16は炭素原子数1〜5のアルキル基であり、nは0〜3の整数を表す。)
(実施例1)重合性化合物(RM1)の合成
冷却管付き300mlナスフラスコに、4、4’−ビフェノール 6.7g(35.9mmol)、2−(4−ブロモブチル)−1,3−ジオキソラン 15.0g(71.7mmol)、炭酸カリウム19.8g(143mmol)、およびアセトン150mlを加えて混合物とし、60℃で48時間攪拌しながら反応させた。反応終了後、減圧下で溶媒を留去し、黄色の湿潤固体を得た。その後、この固体と水200mlを混合し、クロロホルム80mlを加えて抽出した。抽出は3回行った。
冷却管付き300mlナスフラスコに、4,4’−ビフェニルジカルボキシアルデヒド5.0g(23.8mmol)、2−(ブロモメチル)アクリル酸7.9g(47.6mmol)、10%塩酸(aq)33ml、テトラヒドロフラン(THF)100ml、塩化スズ(II)9.5g(50mmol)を加えて混合物とし、70℃で20時間攪拌して反応させた。反応終了後、反応液を純水300mlに注ぎ、白色固体を得た。得られた固体を分離し、再結晶(ヘキサン/クロロホルム=2/1)で精製した後、白色固体3.5gを得た。この固体をNMRで測定した結果、この白色の固体が目的の下記式で表される重合性化合物(RM2)であることが確認された。収率は72%であった。
公知の下記式で表される重合性化合物をRM3とした。
冷却管付き500mlナスフラスコに、4、4’−ビフェノール 11.2g(60mmol)、2−(2−ブロモエチル)−1,3−ジオキソラン25.0g(138mmol)、炭酸カリウム35.9g(260mmol)、およびアセトン200mlを加えて混合物とし、60℃で48時間攪拌しながら反応させた。反応終了後、減圧下で溶媒を留去し、黄色の湿潤固体を得た。その後、この固体と水200mlを混合し、クロロホルム100mlを加えて抽出した。抽出は3回行った。
1H-NMR(CDCl3) δ:2.19(m, 4H), 3.89(m, 4H), 4.01(m, 4H), 4.16(m, 4H), 5.11(m, 2H), 6.95(m, 4H), 7.45(m, 4H).
1H-NMR(CDCl3) δ: 2.18(m, 4H), 2.76(m, 2H), 3.16(m, 2H), 4.18(m, 4H), 4.84(m, 2H), 5.67(m, 2H), 6.27(m, 2H), 6.95(d, 4H), 7.46(m, 4H).
下記液晶配向剤の調製で用いた略号は以下のとおりである。
BODA:ビシクロ[3,3,0]オクタン−2,4,6,8−テトラカルボン酸二無水物
CBDA:1,2,3,4−シクロブタンテトラカルボン酸二無水物
TCA:下記式で表される2,3,5−トリカルボキシシクロペンチル酢酸―1,4:2,3−二無水物
p−PDA:p−フェニレンジアミン
PCH:1,3−ジアミノ−4−[4−(4−ヘプチルシクロヘキシル)フェノキシ]ベンゼン
DBA:3,5−ジアミノ安息香酸
DA−1:下記式で表される2−(メタクリロイロキシ)エチル 3,5−ジアミノベンゾエート
NMP:N−メチル−2−ピロリドン
BCS:ブチルセロソルブ
装置:センシュー科学社製 常温ゲル浸透クロマトグラフィー(GPC)装置(SSC−7200)、
カラム:Shodex社製カラム(KD−803、KD−805)
カラム温度:50℃
溶離液:N,N’−ジメチルホルムアミド(添加剤として、臭化リチウム−水和物(LiBr・H2O)が30mmol/L、リン酸・無水結晶(o−リン酸)が30mmol/L、テトラヒドロフラン(THF)が10ml/L)
流速:1.0ml/分
検量線作成用標準サンプル:東ソー社製 TSK 標準ポリエチレンオキサイド(分子量約900,000、150,000、100,000、30,000)、および、ポリマーラボラトリー社製 ポリエチレングリコール(分子量 約12,000、4,000、1,000)。
イミド化率(%)=(1−α・x/y)×100
BODA(28.15g、112.5mmol)、m−PDA(4.86g、45mmol)、PCH(11.42g、30mmol)、DBA(11.41g、75mmol)をNMP(187.8g)中で混合し、80℃で5時間反応させたのち、CBDA(6.77g、36mmol)とNMP(62.6g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(313g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(79.1g)、およびピリジン(30.7g)を加え、100℃で3時間反応させた。この反応溶液をメタノール(4000ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(A)を得た。このポリイミドのイミド化率は70%であり、数平均分子量は18000、重量平均分子量は59000であった。
BODA(8.76g、35.0mmol)、p−PDA(3.78g、35.0mmol)、PCH(5.33g、14.0mmol)、DA−1(5.55g、21.0mmol)をNMP(90.0g)中で混合し、80℃で5時間反応させたのち、CBDA(6.59g、33.6mmol)とNMP(30.0g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(140.0g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(20.0g)、およびピリジン(25.8g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(1800ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(B)を得た。このポリイミドのイミド化率は50%であり、数平均分子量は22000、重量平均分子量は77000であった。
BODA(3.13g、12.5mmol)、p−PDA(1.08g、10mmol)、PCH(1.90g、5mmol)、DA−1(2.64g、10mmol)をNMP(33.3g)中で混合し、80℃で5時間反応させたのち、CBDA(2.35g、12mmol)とNMP(11.1g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(55.5g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(7.7g)、およびピリジン(9.9g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(710ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(C)を得た。このポリイミドのイミド化率は48%であり、数平均分子量は26000、重量平均分子量は102000であった。
BODA(3.13g、12.5mmol)、p−PDA(0.81g、7.5mmol)、PCH(1.90g、5mmol)、DA−1(3.30g、12.5mmol)をNMP(34.5g)中で混合し、80℃で5時間反応させたのち、CBDA(2.35g、12mmol)とNMP(11.5g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(57.5g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(7.7g)、およびピリジン(9.9g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(730ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(D)を得た。このポリイミドのイミド化率は50%であり、数平均分子量は23000、重量平均分子量は63000であった。
BODA(5.00g、20mmol)、p−PDA(0.87g、8mmol)、PCH(3.05g、8mmol)、DA−1(6.34g、24mmol)をNMP(57.1g)中で混合し、80℃で5時間反応させたのち、CBDA(3.77g、19.2mmol)とNMP(19.0g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(95.5g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(12.3g)、およびピリジン(15.9g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(1200ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(E)を得た。このポリイミドのイミド化率は51%であり、数平均分子量は31000、重量平均分子量は111000であった。
BODA(5.00g、20.0mmol)、p−PDA(2.16g、20.0mmol)、PCH(3.04g、8.0mmol)、DA−2(2.44g、12.0mmol)をNMP(49.2g)中で混合し、80℃で5時間反応させたのち、CBDA(3.77g、19.2mmol)とNMP(16.4g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(75.0g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(9.33g)、およびピリジン(14.6g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(950ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(F)を得た。このポリイミドのイミド化率は47%であり、数平均分子量は20100、重量平均分子量は106000であった。
BODA(5.00g、20.0mmol)、p−PDA(0.87g、8.0mmol)、PCH(3.04g、8.0mmol)、DA−2(4.88g、24.0mmol)をNMP(52.7g)中で混合し、80℃で5時間反応させたのち、CBDA(3.77g、19.2mmol)とNMP(17.56g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(75g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(8.7g)、およびピリジン(13.5g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(950ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(G)を得た。このポリイミドのイミド化率は50%であり、数平均分子量は20000、重量平均分子量は86000であった。
TCA(3.36g、15.0mmol)、p−PDA(1.30g、12.0mmol)、DA−3(3.14g、6.0mmol)、DA−1(3.17g、12.0mmol)をNMP(41.6g)中で混合し、60℃で5時間反応させたのち、CBDA(2.88g、14.7mmol)とNMP(13.9g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(68g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(6.0g)、およびピリジン(11.7g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(850ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(H)を得た。このポリイミドのイミド化率は50%であり、数平均分子量は18000、重量平均分子量は58000であった。
BODA(6.01g、24.0mmol)、p−PDA(2.60g、24.0mmol)、PCH(6.85g、18.0mmol)、DA−1(4.76g、18.0mmol)をNMP(81.5g)中で溶解し、80℃で5時間反応させたのち、CBDA(6.94g、35.4mmol)とNMP(27.2g)を加え、40℃で10時間反応させポリアミック酸溶液を得た。このポリアミック酸溶液(135g)にNMPを加え6質量%に希釈した後、イミド化触媒として無水酢酸(18.3g)、およびピリジン(23.6g)を加え、50℃で3時間反応させた。この反応溶液をメタノール(1700ml)に投入し、得られた沈殿物を濾別した。この沈殿物をメタノールで洗浄し、100℃で減圧乾燥しポリイミド粉末(I)を得た。このポリイミドのイミド化率は60%であり、数平均分子量は12000、重量平均分子量は39000であった。
重合性化合物を含む液晶を次のようにして調整した。MLC−6608(メルク社製商品名)20gに対して、実施例1で得られた重合性化合物RM1を0.0147g(3×10−5mol)添加し、80℃で3時間攪拌溶解させ、液晶1を調製した。
(実施例13)
実施例4で得られた液晶配向剤(A1)を用いて下記に示すような手順で液晶セルの作製を行った。実施例4で得られた液晶配向剤(A1)を、画素サイズが100μm×300μmでライン/スペースがそれぞれ5μmのITO電極パターンが形成されているITO電極基板のITO面にスピンコートし、80℃のホットプレートで90秒間乾燥した後、200℃の熱風循環式オーブンで30分間焼成を行い、膜厚100nmの液晶配向膜を形成した。
まず、バックライト、クロスニコルの状態にした一組の偏光版、光量検出器の順で構成される測定装置において、一組の偏光版の間に液晶セルを配置した。このときライン/スペースが形成されているITO電極のパターンがクロスニコルに対して45°の角度になるようにした。そして、上記の液晶セルに電圧±4V、周波数1kHzの矩形波を印加し、光量検出器によって観測される輝度が飽和するまでの変化をオシロスコープにて取り込み、電圧を印加していない時の輝度を0%、±4Vの電圧を印加し、飽和した輝度の値を100%として、輝度が10%から90%まで変化するのにかかる時間を応答速度とした。
液晶1のかわりに液晶2を用いた以外は実施例13と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶1のかわりに液晶3を用いた以外は実施例13と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A1)のかわりに液晶配向剤(A2)を用い、液晶1のかわりにMLC−6608を用い、また、UVを5J照射するかわりに20J照射した以外は実施例13と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(A3)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(A1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(B2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(B1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(C2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(C1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(D2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(D1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(E2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(E1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(F2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(F1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(G2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(G1)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(H2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
上記の液晶配向剤(D1)10.0gに対して実施例2で得られた重合性化合物RM2を0.06g(固形分に対して10質量%)添加し、室温で3時間攪拌溶解させ、液晶配向剤(D3)を調製した。
上記の液晶配向剤(D1)10.0gに対して比較例1の重合性化合物RM3を0.06g(固形分に対して10質量%)添加し、室温で3時間攪拌溶解させ、液晶配向剤(D4)を調製した。
液晶配向剤(D2)のかわりに液晶配向剤(D3)を用いた以外は実施例19と同様の操作を行って、UV照射前後での応答速度を比較した。結果を表3に示す。
熱循環式オーブンでの焼成を200℃30分間とするかわりに、160℃での30分間とした以外は実施例25と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(D3)のかわりに液晶配向剤(D4)を用いた以外は実施例25と同様の操作を行って、UV照射前後での応答速度を比較した。
熱循環式オーブンでの焼成を200℃30分間とするかわりに、160℃での30分間とした以外は比較例11と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(A2)のかわりに液晶配向剤(I2)を用いた以外は実施例15と同様の操作を行って、UV照射前後での応答速度を比較した。
焼成温度を200℃から140℃へ変更した以外は実施例27と同様の操作を行って、UV照射前後での応答速度を比較した。
液晶配向剤(I2)のかわりに液晶配向剤(I1)を用いた以外は実施例27と同様の操作を行って、UV照射前後での応答速度を比較した。
焼成温度を200℃から140℃へ変更した以外は比較例13と同様の操作を行って、UV照射前後での応答速度を比較した。
TEOS:テトラエトキシシラン
C18:オクタデシルトリエトキシシラン
ACPS:3−アクリロキシプロピルトリメトキシシラン
UPS:3−ウレイドプロピルトリエトキシシラン
MPMS:3−メタクリロキシプロピルトリメトキシシラン
VTES:トリエトキシビニルシラン
NMP:N−メチル−2−ピロリドン
HG:2−メチル−2,4−ペンタンジオール(別名:ヘキシレングリコール)
BCS:2−ブトキシエタノール
(比較例15)
温度計、還流管を備え付けた100mLの四つ口反応フラスコ中でBCS24.5g、TEOS32.4g、C18を1.34g混合して、アルコキシシランモノマーの溶液を調製した。この溶液に、予めBCS12.3g、水8.65g及び触媒として蓚酸0.14gを混合した溶液を、室温下で30分かけて滴下した。この溶液を30分間撹拌してから30分間還流させた後、予めUPS含有量92質量%のメタノール溶液0.46g、BCS0.34gの混合液を加えた。更に30分間還流させてから放冷してSiO2換算濃度が12質量%のポリシロキサン溶液を得た。
比較例15で得られた液晶配向剤(a)に重合性化合物RM1を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例15で得られた液晶配向剤(a)に重合性化合物RM1を20質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例15で得られた液晶配向剤(a)に重合性化合物RM2を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
温度計、還流管を備え付けた100mLの四つ口反応フラスコ中でBCS24.5g、TEOS25.7g、C18を1.33g、及びVTESを6.09g混合して、アルコキシシランモノマーの溶液を調製した。この溶液に、予めBCS12.3g、水8.64g及び触媒として蓚酸0.72gを混合した溶液を、室温下で30分かけて滴下した。この溶液を30分間撹拌してから30分間還流させた後、予めUPS含有量92質量%のメタノール溶液0.46g、BCS0.34gの混合液を加えた。更に30分間還流させてから放冷してSiO2換算濃度が12質量%のポリシロキサン溶液を得た。
比較例16で得られた液晶配向剤(b)に重合性化合物RM1を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例16で得られた液晶配向剤(b)に重合性化合物RM2を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
温度計、還流管を備え付けた100mLの四つ口反応フラスコ中でBCS23.3g、TEOS22.3g、C18を1.33g、及びACPSを11.3g混合して、アルコキシシランモノマーの溶液を調製した。この溶液に、予めBCS11.6g、水8.64g及び触媒として蓚酸0.72gを混合した溶液を、室温下で30分かけて滴下した。この溶液を30分間撹拌してから30分間還流させた後、予めUPS含有量92質量%のメタノール溶液0.46g、BCS0.34gの混合液を加えた。更に30分間還流させてから放冷してSiO2換算濃度が12質量%のポリシロキサン溶液を得た。
比較例17で得られた液晶配向剤(c)に重合性化合物RM1を5質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例17で得られた液晶配向剤(c)に重合性化合物RM1を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例17で得られた液晶配向剤(c)に重合性化合物RM3を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
温度計、還流管を備え付けた100mLの四つ口反応フラスコ中でBCS23.4g、TEOS25.7g、C18を1.33g、及びMPMSを7.95g混合して、アルコキシシランモノマーの溶液を調製した。この溶液に、予めBCS11.7g、水8.64g及び触媒として蓚酸0.58gを混合した溶液を、室温下で30分かけて滴下した。この溶液を30分間撹拌してから30分間還流させた後、予めUPS含有量92質量%のメタノール溶液0.46g、BCS0.34gの混合液を加えた。更に30分間還流させてから放冷してSiO2換算濃度が12質量%のポリシロキサン溶液を得た。
比較例19で得られた液晶配向剤(d)に重合性化合物RM1を5質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例19で得られた液晶配向剤(d)に重合性化合物RM1を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
比較例19で得られた液晶配向剤(d)に重合性化合物RM3を10質量%となるように加え、室温で5時間攪拌しワニス(液晶配向剤)を調製した。
(実施例38)
実施例29で得られたワニス(液晶配向剤)を用いて下記に示すような手順で液晶セルの作製を行った。まず、実施例29で得られたワニスを、画素サイズが100μm×300μmでライン/スペースがそれぞれ5μmのITO電極パターンが形成されているITO電極基板のITO面にスピンコートし、80℃のホットプレートで5分間乾燥した後、200℃の熱風循環式オーブンで30分間焼成を行い、膜厚100nmの液晶配向膜を形成した。
まず、バックライト、クロスニコルの状態にした一組の偏光版、光量検出器の順で構成される測定装置において、一組の偏光版の間に液晶セルを配置した。このときライン/スペースが形成されているITO電極のパターンがクロスニコルに対して45°の角度になるようにした。そして、上記の液晶セルに電圧±4V、周波数1kHzの矩形波を印加し、光量検出器によって観測される輝度が飽和するまでの変化をオシロスコープにて取り込み、電圧を印加していない時の輝度を0%、±4Vの電圧を印加し、飽和した輝度の値を100%として、輝度が10%から90%まで変化するのにかかる時間を応答速度とした。
実施例29で得られたワニスのかわりに実施例30で得られたワニスを用いた以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例31で得られたワニスを用いた以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例32で得られたワニスを用いた以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例33で得られたワニスを用いた以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例34で得られたワニスを用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例35で得られたワニスを用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例36で得られたワニスを用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに実施例37で得られたワニスを用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに比較例15で得られた液晶配向剤(a)を用いた以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに比較例16で得られた液晶配向剤(b)を用いた以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに比較例17で得られた液晶配向剤(c)を用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに比較例18で得られたワニスを用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに比較例19で得られた液晶配向剤(d)を用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
実施例29で得られたワニスのかわりに比較例20で得られたワニスを用い、また、UVを10J照射するかわりに5J照射した以外は実施例38と同様の操作を行った。
Claims (10)
- 下記式(1)で表される重合性化合物と、液晶を垂直に配向させる液晶配向膜を形成する重合体と、溶媒とを有することを特徴とする液晶配向剤。
- 前記液晶を垂直に配向させる液晶配向膜を形成する重合体が、液晶を垂直に配向させる側鎖を有するポリイミド前駆体及び該ポリイミド前駆体をイミド化させて得られるポリイミドから選択される少なくとも一種を含むことを特徴とする請求項1に記載する液晶配向剤。
- 前記液晶を垂直に配向させる液晶配向膜を形成する重合体が、液晶を垂直に配向させる側鎖を有するポリシロキサンを含むことを特徴とする請求項1に記載する液晶配向剤。
- 前記ポリシロキサンが、光反応性の側鎖を有することを特徴とする請求項3に記載する液晶配向剤。
- 前記ポリシロキサンが、アルコキシシラン及びその縮合物から選択される少なくとも一種を重縮合して得られたものであることを特徴とする請求項3または4に記載する液晶配向剤。
- 前記アルコキシシランが、下記式(7)で表されるアルコキシシランを含むことを特徴とする請求項5に記載する液晶配向剤。
R11Si(OR12)3 (7)
(R11はフッ素原子で水素原子が置換されていてもよい、炭素数8〜30の炭化水素基であり、R12は炭素数1〜5のアルキル基を表す。) - 前記アルコキシシランが、下記式(8)を含むことを特徴とする請求項5または6に記載する液晶配向剤。
R13Si(OR14)3 (8)
(R13はアクリル基、メタクリル基、ビニル基、エポキシ基、ビニロキシ基及びアクリロキシ基から選択される少なくとも一種で水素原子が置換されたアルキル基を表し、R14は炭素数1〜5のアルキル基を表す。) - 請求項1〜7のいずれか一項に記載する液晶配向剤を基板に塗布し、焼成して得られる
ことを特徴とする液晶配向膜。 - 液晶中又は液晶配向膜中に請求項1に記載する液晶配向剤を含有させ、これに電圧を印加しながら紫外線を照射して作製された液晶セルを具備することを特徴とする液晶表示素子。
- 液晶中又は液晶配向膜中に請求項1に記載する液晶配向剤を含有させ、これに電圧を印加しながら紫外線を照射して液晶セルを作製することを特徴とする液晶表示装置の製造方法。
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CN103328459B (zh) * | 2011-02-25 | 2015-09-30 | 日产化学工业株式会社 | 聚合性液晶化合物、聚合性液晶组合物及取向膜 |
CN104246591B (zh) * | 2012-02-03 | 2017-08-08 | 日产化学工业株式会社 | 液晶取向处理剂、液晶取向膜及液晶显示元件 |
JP6375774B2 (ja) * | 2013-11-15 | 2018-08-22 | Jsr株式会社 | 液晶配向膜の製造方法、液晶表示素子用基板及びその製造方法、並びに液晶表示素子 |
JPWO2015115588A1 (ja) * | 2014-01-30 | 2017-03-23 | 日産化学工業株式会社 | 液晶配向剤、液晶配向膜、及び液晶表示素子 |
CN106575060B (zh) * | 2014-06-17 | 2019-11-29 | 日产化学工业株式会社 | 液晶表示元件、液晶取向膜和液晶取向处理剂 |
KR102508578B1 (ko) * | 2014-11-04 | 2023-03-09 | 닛산 가가쿠 가부시키가이샤 | 부티로락톤 화합물 및 제조 방법 |
KR102462576B1 (ko) * | 2014-11-04 | 2022-11-02 | 닛산 가가쿠 가부시키가이샤 | 부티로락톤 화합물의 제조 방법 |
TWI560242B (en) * | 2014-11-05 | 2016-12-01 | Chi Mei Corp | Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element |
TWI560241B (en) * | 2014-11-05 | 2016-12-01 | Chi Mei Corp | Liquid crystal alignment agent, liquid crystal alignment film, and liquid crystal display element |
TW201632609A (zh) * | 2014-12-12 | 2016-09-16 | Dainippon Ink & Chemicals | 液晶顯示元件及其製造方法 |
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