JP2019535029A - 液晶配向剤組成物、これを利用した液晶配向膜の製造方法、およびこれを利用した液晶配向膜 - Google Patents
液晶配向剤組成物、これを利用した液晶配向膜の製造方法、およびこれを利用した液晶配向膜 Download PDFInfo
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- JP2019535029A JP2019535029A JP2019510812A JP2019510812A JP2019535029A JP 2019535029 A JP2019535029 A JP 2019535029A JP 2019510812 A JP2019510812 A JP 2019510812A JP 2019510812 A JP2019510812 A JP 2019510812A JP 2019535029 A JP2019535029 A JP 2019535029A
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- BMVLSWZVAKKWBS-UHFFFAOYSA-N NC1=CC=C(C=C1)C1=CC=C(C=N1)N.NC1=CC=C(C=C1)C1=CC=C(C=N1)N Chemical compound NC1=CC=C(C=C1)C1=CC=C(C=N1)N.NC1=CC=C(C=C1)C1=CC=C(C=N1)N BMVLSWZVAKKWBS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- JGNPSJMNGPUQIW-UHFFFAOYSA-N [C].CC=C Chemical compound [C].CC=C JGNPSJMNGPUQIW-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BDJAEZRIGNCQBZ-UHFFFAOYSA-N methylcyclobutane Chemical compound CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 239000012970 tertiary amine catalyst Substances 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Abstract
Description
[化学式1]
R1およびR2のうちの少なくとも一つは炭素数1から10のアルキル基であり、残りは水素であり、
X1およびX2は、それぞれ独立して、下記化学式3で表される4価の有機基であり、
[化学式3]
R3からR8は、それぞれ独立して、水素または炭素数1から6のアルキル基であり、
L1は単結合、−O−、−CO−、−COO−、−S−、−SO−、−SO2−、−CR9R10−、−(CH2)Z−、−O(CH2)ZO−、−COO(CH2)ZOCO−、−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択されたいずれか一つであり、
前記R9およびR10は、それぞれ独立して、水素、炭素数1から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から10の整数であり、
Y1およびY2は、それぞれ独立して、下記化学式4で表される2価の有機基であり、
[化学式4]
Q1からQ4のうちの少なくとも一つは窒素であり、残りは炭素であり、
R3は水素または炭素数1から6のアルキル基であり、
[化学式5]
Aは−O−、−CO−、−S−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)b−、−O(CH2)bO−、−COO−(CH2)b−OCO−、ウレタン系作用基、およびウレア系作用基を含む有機基であり、
bは1から10の整数であり、
R11は炭素数1から20のアルキレン基または炭素数6から20のアリーレン基であり、
mは1から5の整数であり、
Dは下記化学式6で表される作用基であり、
[化学式6]
Tは−O−または−NH−であり、
R12は水素、ハロゲン、炭素数1から6のアルキル基、炭素数6から20のアリール基またはエーテル基であり、
R13は水素または炭素数1から6のアルキル基である。
[化学式12]
[化学式13]
[化学式6]
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
Claims (18)
- 下記の化学式1で表される繰り返し単位、または下記の化学式2で表される繰り返し単位を含む重合体;および
下記の化学式5で表されポリカルボジイミド化合物を含む、
液晶配向剤組成物:
[化学式1]
R1およびR2のうちの少なくとも一つは炭素数1から10のアルキル基であり、残りは水素であり、
X1およびX2は、それぞれ独立して、下記の化学式3で表される4価の有機基であり、
[化学式3]
R3からR8は、それぞれ独立して、水素または炭素数1から6のアルキル基であり、
L1は単結合、−O−、−CO−、−COO−、−S−、−SO−、−SO2−、−CR9R10−、−(CH2)Z−、−O(CH2)ZO−、−COO(CH2)ZOCO−、−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択されたいずれか一つであり、
前記R9およびR10は、それぞれ独立して、水素、炭素数1から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から10の整数であり、
Y1およびY2は、それぞれ独立して、下記の化学式4で表される2価の有機基であり、
[化学式4]
Q1からQ4のうちの少なくとも一つは窒素であり、残りは炭素であり、
R3は水素または炭素数1から6のアルキル基であり、
[化学式5]
Aは−O−、−CO−、−S−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)b−、−O(CH2)bO−、−COO−(CH2)b−OCO−、ウレタン系作用基、およびウレア系作用基を含む有機基であり、
bは1から10の整数であり、
R11は炭素数1から20のアルキレン基または炭素数6から20のアリーレン基であり、
mは1から5の整数であり、
Dは下記の化学式6で表される作用基であり、
[化学式6]
Tは−O−または−NH−であり、
R12は水素、ハロゲン、炭素数1から6のアルキル基、炭素数6から20のアリール基またはエーテル基であり、
R13は水素または炭素数1から6のアルキル基である。 - 前記化学式6で表される作用基で、
Tは−O−であり、R12は下記の化学式6−1のエーテル基であり、
R13は水素である、
請求項1に記載の液晶配向剤組成物:
[化学式6−1]
R14は水素または炭素数1から6のアルキル基であり、
R15は炭素数1から6のアルキレン基であり、
pは1以上の整数である。 - 前記化学式6で表される作用基で、
Tは−NH−であり、
R12は水素、ハロゲン、炭素数1から6のアルキル基、炭素数6から20のアリール基であり、
R13は水素である、
請求項1に記載の液晶配向剤組成物。 - 前記化学式5で表されポリカルボジイミド化合物は、
前記液晶配向剤組成物の全体重量を基準に0.5重量%から15重量%で含有される、
請求項1から3のいずれか1項に記載の液晶配向剤組成物。 - 前記重合体は下記の化学式7または化学式8で表される繰り返し単位をさらに含む、
請求項1から4のいずれか1項に記載の液晶配向剤組成物:
[化学式7]
Xは請求項1で定義したX1またはX2であり、
Yは請求項1で定義したY1またはY2であり、
R30は水素または炭素数1から10のアルキル基であり、
Dは請求項1で定義したとおりである。 - 前記化学式7または化学式8で表される繰り返し単位は、
前記化学式1または化学式2で表される繰り返し単位モル数を基準に0.1モル%から20モル%で含有される、
請求項5に記載の液晶配向剤組成物。 - 前記化学式4のQ1からQ4で、
Q2およびQ4のうちの一つが窒素であり、残りは炭素であり、
Q1、およびQ3は炭素である、
請求項1から6のいずれか1項に記載の液晶配向剤組成物。 - 前記化学式4のQ1からQ4で、
Q2は、窒素であり、
Q1、Q3およびQ4は炭素である、
請求項1から6のいずれか1項に記載の液晶配向剤組成物。 - 前記化学式4で、R3は水素である、
請求項1から8のいずれか1項に記載の液晶配向剤組成物。 - 前記化学式4は、下記の化学式4−1から化学式4−3で表される作用基を含む、
請求項1から9のいずれか1項に記載の液晶配向剤組成物:
[化学式4−1]
- 前記化学式5で、Aで表される作用基は、下記の化学式21で表される作用基、または下記の化学式22で表される作用基である、
請求項1から10のいずれか1項に記載の液晶配向剤組成物:
[化学式21]
R'は2価の有機作用基であり、
G1は、Tは−O−であり、
R12は下記の化学式6−1のエーテル基であり、
R13は水素である化学式6の作用基であり、
[化学式6]
R14は水素または炭素数1から6のアルキル基であり、
R15は炭素数1から6のアルキレン基であり、
pは1から5の整数であり、
[化学式22]
R"は3価の有機作用基であり、
G2は、Tは−O−であり、
R12は下記の化学式6−1のエーテル基であり、
R13は水素である化学式6の作用基であり、
[化学式6]
R14は水素または炭素数1から6のアルキル基であり、
R15は炭素数1から6のアルキレン基であり、
pは1から5の整数であり、
G3は、Tは−NH−であり、
R12は水素、ハロゲン、炭素数1から6のアルキル基、炭素数6から20のアリール基であり、
R13は水素である
化学式6の作用基である。 - 請求項1から11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;
前記塗膜を乾燥する段階の直後の塗膜に光を照射するかまたはラビング処理して配向処理する段階;および
前記配向処理され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12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℃から150℃で行われる、
請求項12または13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、光照射は、150nmから450nm波長の偏光された紫外線を照射する、
請求項12から14のいずれか1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、熱処理温度は、150℃から300℃である、
請求項12から15のいずれか1項に記載の液晶配向膜の製造方法。 - 請求項1から11のいずれか1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17に記載の液晶配向膜を含む
液晶表示素子。
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