JPWO2020171128A1 - 液晶配向剤及びそれを用いた液晶表示素子 - Google Patents
液晶配向剤及びそれを用いた液晶表示素子 Download PDFInfo
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- JPWO2020171128A1 JPWO2020171128A1 JP2021502095A JP2021502095A JPWO2020171128A1 JP WO2020171128 A1 JPWO2020171128 A1 JP WO2020171128A1 JP 2021502095 A JP2021502095 A JP 2021502095A JP 2021502095 A JP2021502095 A JP 2021502095A JP WO2020171128 A1 JPWO2020171128 A1 JP WO2020171128A1
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- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- DBNQIOANXZVWIP-UHFFFAOYSA-N n,n-dimethyl-1,1-bis[(2-methylpropan-2-yl)oxy]methanamine Chemical compound CC(C)(C)OC(N(C)C)OC(C)(C)C DBNQIOANXZVWIP-UHFFFAOYSA-N 0.000 description 1
- NSLGQFIDCADTAS-UHFFFAOYSA-N n,n-dimethyl-1,1-dipropoxymethanamine Chemical compound CCCOC(N(C)C)OCCC NSLGQFIDCADTAS-UHFFFAOYSA-N 0.000 description 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- JCMFJIHDWDKYIL-UHFFFAOYSA-N propyl 3-methoxypropanoate Chemical compound CCCOC(=O)CCOC JCMFJIHDWDKYIL-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000012976 tarts Nutrition 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-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
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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Abstract
Description
近年、スマートフォンやタブレット型端末向けの高精細液晶表示素子において、高い表示品位が求められている中、液晶配向膜にも、液晶配向性の他に、種々の特性が高いレベルで要求されている。
1.下記の(A)成分、(B)成分、及び有機溶剤を含有することを特徴とする液晶配向剤。
本発明の液晶配向剤に含まれる(A)成分は、ポリイミド前駆体及び該ポリイミド前駆体のイミド化重合体からなる群から選ばれる少なくとも1種類の重合体であり、その構造は特に限定されない。
本発明の液晶配向剤に含有されるポリイミド前駆体は、テトラカルボン酸誘導体と、ジアミンとの反応から得られ、ポリイミドは、ポリイミド前駆体をイミド化することにより得られる。以下に、用いられる材料の具体例及び製造方法を詳述する。
ポリイミド前駆体の製造に用いられるジアミンは、下記式(3)で表される。
本発明の液晶配向剤に含有される(B)成分は、ヒドロキシアルキルアミド基を有する基及び下記式(1)の構造を有する化合物である。
好ましくは、水素原子もしくはメチル基である。*は他の原子との結合を表す。
本発明に用いられるポリイミド前駆体であるポリアミック酸は、以下に示す方法で製造できる。具体的には、テトラカルボン酸二無水物とジアミンとを有機溶媒の存在下、−20℃〜150℃、好ましくは0℃〜50℃で、30分〜24時間、好ましくは1〜12時間反応させることによって合成できる。
本発明に用いられるポリイミド前駆体の一つであるポリアミック酸エステルは、以下に示す(1)、(2)又は(3)の方法で製造できる。
ポリアミック酸エステルは、テトラカルボン酸二無水物とジアミンから得られるポリアミック酸をエステル化することによって合成できる。具体的には、ポリアミック酸とエステル化剤を有機溶剤の存在下で−20℃〜150℃、好ましくは0℃〜50℃において、30分〜24時間、好ましくは1〜4時間反応させることによって合成できる。
ポリアミック酸エステルは、テトラカルボン酸ジエステルジクロリドとジアミンから製造できる。具体的には、テトラカルボン酸ジエステルジクロリドとジアミンとを塩基と有機溶剤の存在下で−20℃〜150℃、好ましくは0℃〜50℃において、30分〜24時間、好ましくは1〜4時間反応させることによって合成することができる。
ポリアミック酸エステルは、テトラカルボン酸ジエステルとジアミンを重縮合することにより製造できる。具体的には、テトラカルボン酸ジエステルとジアミンを縮合剤、塩基、及び有機溶剤の存在下で0℃〜150℃、好ましくは0℃〜100℃において、30分〜24時間、好ましくは3〜15時間反応させることによって製造できる。
本発明に用いられるポリイミドは、前記ポリアミック酸又はポリアミック酸エステルをイミド化することにより製造できる。本発明で用いられるポリイミドイミド化率は100%に限らない。電気特性の観点から20〜99%が好ましい。ポリアミック酸エステルからポリイミドを製造する場合、前記ポリアミック酸エステル溶液、又はポリアミック酸エステル樹脂粉末を有機溶媒に溶解させて得られるポリアミック酸溶液に塩基性触媒を添加する化学的イミド化が簡便である。化学的イミド化は、比較的低温でイミド化反応が進行し、イミド化の課程で重合体の分子量低下が起こりにくいので好ましい。
本発明に用いられる液晶配向剤は、前記した(A)成分であるポリイミド前駆体及び該ポリイミド前駆体のイミド化重合体からなる群から選ばれる少なくとも1種の重合体(以下、特定構造の重合体とする)、及び(B)成分であるヒドロキシアルキルアミド基を有する化合物が、溶媒中に溶解された溶液の形態を有する。
<液晶配向膜の製造方法>
本発明の液晶配向膜は、上記液晶配向剤を基板に塗布し、乾燥し、焼成して得られる膜である。本発明の液晶配向剤を塗布する基板としては、透明性の高い基板であれば特に限定されず、ガラス基板、窒化珪素基板、アクリル基板、ポリカーボネート基板等のプラスチック基板等を用いることができる。さらに、液晶駆動のためのITO電極等が形成された基板を用いることが、プロセスの簡素化の点から好ましい。また、反射型の液晶表示素子では、片側の基板のみにならばシリコンウエハー等の不透明な物でも使用でき、この場合の電極は、アルミニウム等の光を反射する材料も使用できる。
本発明の液晶表示素子は、前記液晶配向膜の製造方法によって得られた液晶配向膜を具備することを特徴とする。
NMP:N−メチル−2−ピロリドン
GBL:γ―ブチルラクトン
BCS:ブチルセロソルブ
THF:テトラヒドロフラン
DMF:N,N−ジメチルホルムアミド
装置:フーリエ変換型超伝導核磁気共鳴装置(FT−NMR)「AVANCE 3」(BRUKER製)500MHz。
溶媒:重水素化クロロホルム(CDCl3)又は重水素化N,N−ジメチルスルホキシド([D6]−DMSO)。
標準物質:テトラメチルシラン(TMS)。
ポリイミド及びポリアミック酸溶液の粘度は、E型粘度計(東機産業社製、VE−22H)を用い、サンプル量1.1mL、コーンロータTE−1(1°34’、R24)、温度25℃で測定した。
ポリイミド粉末20mgをNMRサンプル管(草野科学社製 NMRサンプリングチューブスタンダード φ5)に入れ、重水素化ジメチルスルホキシド(DMSO−d6、0.05%TMS(テトラメチルシラン)混合品)0.53mlを添加し、超音波をかけて完全に溶解させた。この溶液を日本電子データム社製NMR測定器(JNW−ECA500)にて500MHzのプロトンNMRを測定した。イミド化率は、イミド化前後で変化しない構造に由来するプロトンを基準プロトンとして決め、このプロトンのピーク積算値と、9.5から10.0ppm付近に現れるアミド酸のNH基に由来するプロトンピーク積算値とを用い以下の式によって求めた。
FFSモード液晶表示素子の構成を備えた液晶セルを作製した。
始めに、電極付きの基板を準備した。基板は、30mm×50mmの長方形で、厚みが0.7mmのガラス板である。基板上には第1層目として対向電極を構成する、ベタ状のパターンを備えたITO電極が形成されている。第1層目の対向電極の上には第2層目として、CVD法により成膜されたSiN(窒化珪素)膜が形成されている。第2層目のSiN膜の膜厚は500nmであり、層間絶縁膜として機能する。第2層目のSiN膜の上には、第3層目としてITO膜をパターニングして形成された櫛歯状の画素電極が配置され、第1画素及び第2画素の2つの画素を形成している。各画素のサイズは、縦10mmで横約5mmである。このとき、第1層目の対向電極と第3層目の画素電極とは、第2層目のSiN膜の作用により電気的に絶縁されている。
2L四つ口フラスコに[AD−3−1](30.0g、61mmol)、ビス[2−(トリメチルシリルオキシ)エチル]アミン(45.8g、184mmol)、(2,3−ジヒドロ−2−チオキソ−3−ベンゾオキサゾリル)ホスホン酸ジフェニル(47.0g、122mmol)、トリエチルアミン(45.8g、184mmol)、NMP(450g)を仕込み、室温で撹拌した。反応終了後、反応液を0.5mol/L−塩酸水溶液(2500g)に注ぎ、析出物を濾別した。得られた粗物にメタノール(300g)を加え、室温でリパルプ洗浄することで、[AD−3](白色固体)を30.3g得た。目的物の1H−NMRの結果を以下に示す。この結果から、得られた固体が、目的の[AD−3]であることを確認した。
1H NMR (500 MHz, [D6]-DMSO):δ7.32-7.38 (m,8H), 4.92-4.95 (t,2H), 4.69-4.72 (t,2H), 3.82 (s,4H), 3.55-3.59 (m,6H), 3.47-3.52 (m,8H), 3.36-3.39 (m,4H), 1.40 (s,6H)
1H NMR (500 MHz, [D6]-DMSO):δ7.56-7.58 (d,4H), 7.48-7.50 (d,4H), 4.84-4.87 (t,4H), 3.61-3.65 (m,6H), 3.55-3.56 (d,4H), 3.48-3.50 (d,4H), 3.35 (s,4H), 1.42 (s,6H)
撹拌装置付きおよび窒素導入管付きの200ml四つ口フラスコにDA−1(1.08g、10mmol)、DA−2(3.66g,15mmol)、DA−3(4.81g、15mmol)、DA−4(3.41g、10mmol)を加えた後、NMP132gを加え、窒素を送りながら撹拌し溶解させた。このジアミン溶液を撹拌しながらDAH−1(10.54g,47mmol)を加え,NMPを40.3g加えた後、さらに40℃条件下にて12時間攪拌することで樹脂固形分濃度12質量%のポリアミド酸溶液(PAA−1)を得た。このポリアミック酸溶液の25℃における粘度は380mPa・sであった。
撹拌装置付き及び窒素導入管付きの100mLの四つ口フラスコに、DA−5を3.99g(20mmol)、 DA−6を1.49g(5mmol)量り取り、次いで、NMPを78g加えて、窒素を送りながら撹拌し溶解させた。このジアミン溶液を撹拌しながらDAH−2を6.77g(23mmol)添加し、更に固形分濃度が12質量%になるようにNMPを加え、70℃で20時間撹拌してポリアミック酸溶液(PAA−2)(粘度:420mPa・s)を得た。
撹拌子を入れた50mLの三角フラスコに、製造例1で得られたポリイミド溶液(SPI−1)を5.63g量り取った。NMPを3.34g、GBLを2.03g、BCSを3.00g、AD−1の10%NMP溶液を1.01g加え、マグネチックスターラーで終夜撹拌し液晶配向剤(AL−1)を得た。
撹拌子を入れた50mLの三角フラスコに、製造例1で得られたポリイミド溶液(SPI−1)を5.63g量り取った。NMPを3.34g、GBLを2.03g、BCSを3.00g、AD−2の10%NMP溶液を1.01g加え、マグネチックスターラーで終夜撹拌し液晶配向剤(AL−2)を得た。
撹拌子を入れた50mLの三角フラスコに、製造例1で得られたポリイミド溶液(SPI−1)を5.63g量り取った。NMPを3.34g、GBLを2.03g、BCSを3.00g、AD−3の10%NMP溶液を1.01g加え、マグネチックスターラーで終夜撹拌し液晶配向剤(AL−3)を得た。
撹拌子を入れた50mLの三角フラスコに、製造例1で得られたポリイミド溶液(SPI−1)を5.63g量り取った。NMPを3.34g、GBLを2.03g、BCSを3.00g、AD−4の10%NMP溶液を1.01g加え、マグネチックスターラーで終夜撹拌し液晶配向剤(AL−4)を得た。
撹拌子を入れた50mLの三角フラスコに、製造例1で得られたポリイミド溶液(SPI−1)を1.13g量り取り、製造例2で得られたポリアミック酸溶液(PAA−2)を4.50g添加した。さらにNMPを0.86g、GBLを4.50g、BCSを3.00g、AD−3の10%NMP溶液を1.01g加え、マグネチックスターラーで終夜撹拌し液晶配向剤(AL−5)を得た。
上記の液晶セルを用い、60℃の恒温環境下、周波数30Hzで±5Vの交流電圧を120時間印加した。その後、液晶セルの画素電極と対向電極との間をショートさせた状態にし、そのまま室温に一日放置した。
上記で得られた液晶セルの角度Δが0.15°以上を「×」とし、0.15°未満を「〇」と評価した。
得られた液晶配向剤(AL−1、AL−2、AL−3、AL−4、AL−5)について、上記したようにして長期交流駆動による残像評価を行った。すなわち、液晶配向剤(AL−1、AL−2、AL−3、AL−4、AL−5)を使用し、それぞれ上記したようにしてFFSモード液晶表示素子の構成を備えた液晶セルを作製し、このFFS駆動液晶セルについて、長期交流駆動による残像評価を実施した。その結果を下記表1にまとめる。
液晶配向剤を、全面にITO電極が付いたガラス基板のITO面にスピンコートにて塗布した。80℃のホットプレート上で2分間乾燥させた後、IR式オーブンを用いて230℃、30分焼成を行い、厚み100nmの塗膜を形成させた。この塗膜面に偏光紫外線を300mJ/cm2となるように照射して配向処理を施した。再度IR式オーブンを用いて230℃、30分焼成を行って、液晶配向膜付き基板を得た。この液晶配向膜を、レーヨン布でラビング(ローラー直径:120mm、ローラー回転数:1000rpm、移動速度:20mm/sec、押し込み長:0.6mm)した。本基板を顕微鏡にて観察を行い、膜面にラビングによるスジが見られなかったものを「〇」、スジがみられたものを「×」として評価した。
得られた液晶配向剤(AL−1、AL−2、AL−3、AL−4、AL−5)について、上記の膜強度評価を行った。その結果を下記表2にまとめる。
Claims (11)
- (B)成分が、ヒドロキシアルキルアミド基を2つ以上有する化合物である、請求項1に記載の液晶配向剤。
- (B)成分が、(A)成分に対して0.1〜20質量%含有される、請求項1又は2に記載の液晶配向剤。
- X2中の、カルボニル基に直接結合する原子は、芳香環を形成する炭素原子である、請求項4又は5に記載の液晶配向剤。
- 請求項1〜8のいずれかに記載の液晶配向剤から得られる液晶配向膜。
- 請求項9に記載の液晶配向膜を具備する液晶表示素子。
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