JP6855676B2 - 液晶配向剤組成物、それを用いた液晶配向膜の製造方法、それを用いた液晶配向膜および液晶表示素子 - Google Patents
液晶配向剤組成物、それを用いた液晶配向膜の製造方法、それを用いた液晶配向膜および液晶表示素子 Download PDFInfo
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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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
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Description
本出願は、2017年11月3日付韓国特許出願第10−2017−0146284号および2018年10月30日付韓国特許出願第10−2018−0131273号に基づいた優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は本明細書の一部として含まれている。
[化学式1]
本明細書で特に制限しない限り、次の用語は下記のように定義することができる。
前記重合体は、ポリイミドまたはその前駆体を含む。前記ポリイミドの前駆体は、ポリアミック酸またはポリアミック酸エステルを含み得る。
[化学式2]
X1〜X6は、それぞれ独立して下記化学式8で表される4価の有機基であり、
[化学式8]
Y1〜Y3は、それぞれ独立して下記化学式9で表される2価の有機基であり、
[化学式9]
Y4〜Y6は、それぞれ独立して下記化学式10で表される2価の有機基であり、
[化学式10]
[化学式8−1]
[化学式10−1]
L3は、単結合、−O−、−SO2−、または−CR30R31−であり、ここで、R30およびR31は、それぞれ独立して水素、または炭素数1〜10のアルキルである。
上述した液晶配向剤用重合体以外に、本発明の一実施形態の液晶配向剤組成物は、ポリオキサゾリン架橋剤を含ませることによって、これより製造される液晶配向膜の機械的強度を向上させると同時に高い信頼性および優れた電気的特性を実現することができる。
[化学式1−1]
[化学式1−2]
また、本発明者らは、前記液晶配向剤用重合体以外に、分子内に2個以上、または2個〜6個のエポキシ基を有する化合物を液晶配向剤組成物に含ませることで、これより製造される液晶配向膜は高い電圧保持率を示すことができるだけでなく熱ストレスによる配向安定性および配向膜の機械的強度も改善されることを確認した。理論的に制限されるものではないが、光照射による異方性生成後の熱処理過程でエポキシ基を有する化合物とポリイミド前駆体または部分イミド化した高分子のカルボン酸基と熱架橋反応が起き、これによって電圧保持率を上昇させる。また、特に分子内に2個以上のエポキシ基を有する化合物を用いるため、このような特性がさらに向上するだけでなくポリイミド前駆体または部分イミド化した高分子鎖間の架橋反応を起こして配向安定性および配向膜の機械的強度も向上させることができる。
[化学式11]
また、本発明は、液晶配向剤組成物を基板に塗布して塗膜を形成する段階(段階1);前記塗膜を乾燥する段階(段階2);前記乾燥段階直後の塗膜に光を照射するかラビング処理して配向処理する段階(段階3);および前記配向処理した塗膜を熱処理して硬化する段階(段階4)を含む液晶配向膜の製造方法を提供する。
また、本発明は、上述した液晶配向膜の製造方法により製造された液晶配向膜を提供する。具体的に、前記液晶配向膜は、前記一実施形態の液晶配向剤組成物の配向硬化物を含み得る。前記配向硬化物とは、前記一実施形態の液晶配向剤組成物の配向工程および硬化工程を経て得られる物質を意味する。
[数1]
膜強度(%)=ラビング処理後の液晶配向膜のヘイズ(%)−ラビング処理前の液晶配向膜のヘイズ(%)。
また、本発明は、上述した液晶配向膜を含む液晶表示素子を提供する。
製造例2−1)液晶配向剤用重合体P−1の製造
(段階1)
前記製造例1−2で製造したDA−2 5.0g(13.3mmol)を無水N−メチルピロリドン(anhydrous N−methyl pyrrolidone:NMP)71.27gに完全に溶かした。そして、ice bath下で1,3−ジメチル−シクロブタン−1,2,3,4−テトラカルボン酸二無水物(DMCBDA)2.92g(13.03mmol)を前記溶液に添加して16時間常温で攪拌した。
前記段階1で得られた溶液を過量の蒸溜水に投入して沈殿物を生成させた。次いで、生成された沈殿物を濾過して蒸溜水で2回洗浄して再びメタノールで3回洗浄した。このように得られた固体生成物を40℃の減圧オーブンで24時間乾燥して液晶配向剤用重合体P−1 6.9gを収得した。
前記製造例1−1で製造したDA−1 5.0g,p−フェニレンジアミン(p−phenylenediamine,PDA)1.07gをNMP103.8gに完全に溶かした。そして、ice bath下でシクロブタン−1,2,3,4−テトラカルボン酸二無水物(CBDA)2.12gと4,4'−オキシジフタル酸二無水物(OPDA)3.35gを前記溶液に添加して16時間常温で攪拌した。次いで、前記製造例2−1の段階2と同様の方法により重合体P−2を製造した。
前記製造例1−2で製造したDA−2 6.0g、4,4'−オキシジアニリン(4,4'−oxydianiline,ODA)1.37gをNMP110.5gに完全に溶かした。そして、ice bath下でDMCBDA 3.47gとピロメリット酸二無水物(pyromellitic dianhydride,PMDA)1.44gを前記溶液に添加して16時間常温で攪拌した。次いで、前記製造例2−1の段階2と同様の方法により重合体P−3を製造した。
4,4'−メチレンジアニリン(4,4'−methylenedianiline)5.00gと4,4'−オキシジアニリン(4,4'−oxydianiline)5.05gをNMP221.4gに完全に溶かした。そして、ice bath下で4,4'−ビフタル酸無水物(4,4'−biphthalic anhydride)14.55gを前記溶液に添加して16時間常温で攪拌した。次いで、前記製造例2−1の段階2と同様の方法により重合体Q−1を製造した。
実施例1
前記製造例2−1で製造したP−1 5重量部、前記製造例2−4で製造したQ−1 5重量部、N,N,N',N'−テトラグリシジル−4,4'−ジアミノジフェニルメタン(N,N,N',N'−tetraglycidyl−4,4'−diaminodiphenylmethane,TGMDA)0.5重量部および下記化学式Aの高分子[PEOX、重量平均分子量:約50000g/mol]1重量部をNMPとn−ブトキシエタノールの重量比が8:2である混合溶媒に完全に溶解させた。次いで、ポリ(テトラフルオレンエチレン)材質の気孔サイズが0.2μmであるフィルタで加圧濾過して液晶配向剤組成物を製造した。
前記製造例2−1で製造したP−1の代わりに前記製造例2−2で製造したP−2を用いたことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
前記製造例2−1で製造したP−1の代わりに前記製造例2−3で製造したP−3を用いたことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
前記化学式Aの高分子の代わりに化学式Bの高分子[数平均分子量:約10000g/mol]を用いたことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
[化学式B]
前記化学式Aの高分子の代わりに化学式Cの高分子[数平均分子量:約10000g/mol]を用いたことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
[化学式C]
比較例1
前記化学式Aの高分子を用いないことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
N,N,N',N'−テトラグリシジル−4,4'−ジアミノジフェニルメタンを用いないことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
前記製造例2−1で製造したP−1の代わりに前記製造例2−4で製造したQ−1を用いたことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
前記化学式Aの高分子の代わりに化学式Dの構造を有するポリ(スチレン−co−2−イソプロペニル−オキサゾリン)(株式会社日本触媒製品:エポクロスRPS−1005)を用いたことを除いては、前記実施例1と同様の方法により液晶配向剤組成物を製造した。
[化学式D]
1)液晶配向セルの製造
前記実施例および比較例で製造した液晶配向剤組成物を用いて液晶配向セルを製造した。
前記製造した液晶配向セルの電気的特性である電圧保持率(voltage holding ratio,VHR)をTOYO corporationの6254C装備を用いて測定した。電圧保持率(VHR)は1Hz、60℃温度で測定した(VHR60℃1Hz n−LC条件)。前記液晶配向セルの電圧保持率(VHR)に対する測定結果は、下記表1に示した。
前記製造した液晶配向セルの上板および下板に偏光板を互いに垂直になるように付着した。そして、偏光板が付着された液晶配向セルを明るさ7,000cd/m2のバックライトの上に置いて肉眼で光漏れを観察した。このとき、液晶配向膜の配向特性に優れ、液晶をよく配列させると、互いに垂直に付着された上、下の偏光板によって光が通過せず不良なしに暗く観察される。
前記実施例および比較例で製造された液晶配向剤組成物から得られた配向膜に対し、前記配向膜表面をsindo engineering社のrubbing machineを用いて850rpmで回転させながらラビング処理した後ヘイズメーター(hazemeter)を用いてヘイズ値を測定し、下記数学式1のようにラビング処理前のヘイズ値との差を計算して膜強度を評価した。前記ヘイズ変化値が1未満であれば膜強度に優れるものである。
[数1]
膜強度(%)=ラビング処理後の液晶配向膜のヘイズ(%)−ラビング処理前の液晶配向膜のヘイズ(%)。
1)液晶配向セルの製造
前記塗膜を約230℃のオーブンで30分間焼成(硬化)する前に、塗膜を130℃のホットプレート上に500秒間置いて低温熱処理する段階をさらに含むことを除いては、前記実験例1と同様に液晶セルを製造した。
Claims (15)
- ポリイミドまたはその前駆体を含む重合体;
下記化学式1で表される繰り返し単位を含むポリオキサゾリン架橋剤、および
分子内に2個以上のエポキシ基を有する化合物
を含み、
前記ポリオキサゾリン架橋剤は、
一末端に炭素数1〜20のアルキル基、ヒドロキシ基、チオール基、アルキニル基、アミン基、アジド基、およびシリル基からなる群より選ばれた1種以上が結合し、
前記一末端の逆の他の末端に炭素数1〜20のアルキル基、ヘテロ元素が置換された炭素数1〜20のアルキル基、炭素数2〜20のアルキニル基、炭素数6〜20のアリール基、および炭素数6〜30のアリールアルキル基からなる群より選ばれた1種以上が結合し、
前記重合体は、
i)下記化学式2で表される繰り返し単位、下記化学式3で表される繰り返し単位および下記化学式4で表される繰り返し単位からなる群より選ばれた1種以上の繰り返し単位を含む第1液晶配向剤用重合体;および
ii)下記化学式5で表される繰り返し単位、下記化学式6で表される繰り返し単位および下記化学式7で表される繰り返し単位からなる群より選ばれた1種以上の繰り返し単位を含む第2液晶配向剤用重合体;
を含む、
液晶配向剤組成物:
[化学式1]
R1は、炭素数1〜20のアルキル基、またはヘテロ元素が置換された炭素数1〜20のアルキル基であり、
aは、2〜10000の整数であり、
[化学式2]
R 3 およびR 4 のうち少なくとも一つは、炭素数1〜10のアルキル基であり、残りは水素であり、
R 5 およびR 6 のうち少なくとも一つは、炭素数1〜10のアルキル基であり、残りは水素であり、
X 1 〜X 6 は、それぞれ独立して下記化学式8で表される4価の有機基であり、
[化学式8]
R 9 〜R 14 は、それぞれ独立して水素または炭素数1〜6のアルキル基であり、
L 1 は、単結合、−O−、−CO−、−COO−、−S−、−SO−、−SO 2 −、−CR 15 R 16 −、−(CH 2 ) Z −、−O(CH 2 ) Z O−、−COO(CH 2 ) Z OCO−、−CONH−、フェニレンまたはこれらの組み合わせからなる群より選ばれたいずれか一つであり、
R 15 およびR 16 は、それぞれ独立して水素、炭素数1〜10のアルキル基またはフルオロアルキル基であり、
zは、1〜10の整数であり、
Y 1 〜Y 3 は、それぞれ独立して下記化学式9で表される2価の有機基であり、
[化学式9]
Tは、前記化学式8で表される4価の有機基であり、
D 1 およびD 2 は、それぞれ独立して炭素数1〜20のアルキレン基、炭素数1〜10のヘテロアルキレン基、炭素数3〜20のシクロアルキレン基、炭素数6〜20のアリーレン基または炭素数2〜20のヘテロアリーレン基であり、
Y 4 〜Y 6 は、それぞれ独立して下記化学式10で表される2価の有機基であり、
[化学式10]
R 17 およびR 18 は、それぞれ独立して水素、ハロゲン、シアノ、ニトリル、炭素数1〜10のアルキル、炭素数1〜10のアルケニル、炭素数1〜10のアルコキシ、炭素数1〜10のフルオロアルキル、または炭素数1〜10のフルオロアルコキシであり、
pおよびqは、それぞれ独立して0〜4の整数であり、
L 2 は、単結合、−O−、−CO−、−S−、−SO 2 −、−C(CH 3 ) 2 −、−C(CF 3 ) 2 −、−CONH−、−COO−、−(CH 2 ) y −、−O(CH 2 ) y O−、−O(CH 2 ) y −、−NH−、−NH(CH 2 ) y −NH−、−NH(CH 2 ) y O−、−OCH 2 −C(CH 3 ) 2 −CH 2 O−、−COO−(CH 2 ) y −OCO−、または−OCO−(CH 2 ) y −COO−であり、
yは、1〜10の整数であり、
kおよびmは、それぞれ独立して0〜3の整数であり、
nは、0〜3の整数である。 - 前記ポリオキサゾリン架橋剤は、下記化学式1−1で表される単独重合体を含む、
請求項1に記載の液晶配向剤組成物:
[化学式1−1]
R1は、炭素数1〜20のアルキル基、またはヘテロ元素が置換された炭素数1〜20のアルキル基であり、
R2は、炭素数1〜20のアルキル基、ヘテロ元素が置換された炭素数1〜20のアルキル基、炭素数2〜20のアルキニル基、炭素数6〜20のアリール基、または炭素数6〜30のアリールアルキル基であり、
Xは、炭素数1〜20のアルキル基、ヒドロキシ基、チオール基、アルキニル基、アミン基、アジド基、またはシリル基であり、
aは、2〜10000の整数である。 - 前記ポリオキサゾリン架橋剤は、前記化学式1で表されることができる互いに異なる2種以上の繰り返し単位を含む共重合体を含む、
請求項1に記載の液晶配向剤組成物。 - 前記ポリオキサゾリン架橋剤は、重量平均分子量(GPC測定)が5000g/mol〜1000000g/molである、
請求項1から3のいずれか一項に記載の液晶配向剤組成物。 - 前記ポリオキサゾリン架橋剤は、
前記液晶配向剤組成物の全体重量を基準に0.1重量%〜20重量%で含まれる、
請求項1から4のいずれか一項に記載の液晶配向剤組成物。 - 第1液晶配向剤用重合体と第2液晶配向剤用重合体の重量比は、1:9〜9:1である、
請求項1から5のいずれか1項に記載の液晶配向剤組成物。 - 前記分子内に2個以上のエポキシ基を有する化合物は、前記第1液晶配向剤用重合体および第2液晶配向剤用重合体の重量合計100重量部に対して0.1重量部〜30重量部で含まれる、
請求項1から7のいずれか1項に記載の液晶配向剤組成物。 - 請求項1から8のいずれか一項に記載の液晶配向剤組成物を基板に塗布して塗膜を形成する段階;
前記塗膜を乾燥する段階;
前記乾燥する段階の直後の塗膜に光を照射するかラビング処理して配向処理する段階;および
前記配向処理した塗膜を熱処理して硬化する段階
を含む、
液晶配向膜の製造方法。 - 前記液晶配向剤組成物は、有機溶媒に溶解または分散させたものである、
請求項9に記載の液晶配向膜の製造方法。 - 前記塗膜を乾燥する段階は、50℃〜150℃で行われる、
請求項9または10に記載の液晶配向膜の製造方法。 - 前記配向処理する段階での光照射は、150nm〜450nm波長の偏光した紫外線を照射する、
請求項9から11のいずれか一項に記載の液晶配向膜の製造方法。 - 前記塗膜を硬化する段階での熱処理温度は、150℃〜300℃である、
請求項9から12のいずれか一項に記載の液晶配向膜の製造方法。 - 請求項1から8のいずれか一項に記載の液晶配向剤組成物の配向硬化物を含む、
液晶配向膜。 - 請求項14に記載の液晶配向膜を含む、
液晶表示素子。
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