JP2017088801A5 - - Google Patents
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- JP2017088801A5 JP2017088801A5 JP2015223728A JP2015223728A JP2017088801A5 JP 2017088801 A5 JP2017088801 A5 JP 2017088801A5 JP 2015223728 A JP2015223728 A JP 2015223728A JP 2015223728 A JP2015223728 A JP 2015223728A JP 2017088801 A5 JP2017088801 A5 JP 2017088801A5
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- 125000004432 carbon atoms Chemical group C* 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
- 125000002947 alkylene group Chemical group 0.000 claims description 63
- 150000004985 diamines Chemical class 0.000 claims description 62
- 239000004973 liquid crystal related substance Substances 0.000 claims description 44
- -1 -OH Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000002994 raw material Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 17
- 229920005575 poly(amic acid) Polymers 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000005469 ethylenyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 15
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 12
- 125000005466 alkylenyl group Chemical group 0.000 claims description 9
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 4
- 229920000994 AN-VI Polymers 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatoms Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 230000003287 optical Effects 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000002345 steroid group Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 3
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 0 C*(*(C(C1(CC(*C(CCC2)CC2(C(**[U]=C)=O)N)CCC1)N)=O)=C)=C Chemical compound C*(*(C(C1(CC(*C(CCC2)CC2(C(**[U]=C)=O)N)CCC1)N)=O)=C)=C 0.000 description 15
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Description
[5] テトラカルボン酸二無水物が、下記式(AN−I)〜式(AN−VII)で表されるテトラカルボン酸二無水物の群から選ばれる少なくとも1つであり;
式(1)で表されるジアミンと共に用いられるその他のジアミンが、下記式(DI−1)〜式(DI−16)、式(DIH−1)〜式(DIH−3)、および式(DI−31)〜式(DI−35)からなる群から選ばれる少なくとも1つである、[1]〜[4]のいずれか1項に記載の、ポリアミック酸またはその誘導体。
式(AN−II)において、Gは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(AN−II)〜式(AN−IV)において、Yは独立して下記の3価の基の群から選ばれる1つであり、
式(AN−III)〜式(AN−V)において、環A10は炭素数3〜10の単環式炭化水素の基または炭素数6〜30の縮合多環式炭化水素の基であり、この基の少なくとも1つの水素はメチル、エチルまたはフェニルで置き換えられていてもよく、環に掛かっている結合手は環を構成する任意の炭素に連結しており、2本の結合手が同一の炭素に連結してもよく;
式(AN−VI)において、X10は炭素数2〜6のアルキレンであり、Meはメチルを表し、Phはフェニルを表し、
式(AN−VII)において、G10は独立して−O−、−COO−または−OCO−であり;そして、rは独立して0または1であり;
式(DI−3)および式(DI−5)〜式(DI−7)において、G21は独立して単結合、−NH−、−NCH3−、−O−、−S−、−S−S−、−SO2−、−CO−、−COO−、−CONH−、−CONCH3−、−C(CH3)2−、−C(CF3)2−、−(CH2)m’−、−O−(CH2)m’−O−、−N(CH3)−(CH2)k−N(CH3)−、−(O−C2H4)m’−O−、−O−CH2−C(CF3)2−CH2−O−、−O−CO−(CH2)m’−CO−O−、−CO−O−(CH2)m’−O−CO−、−(CH2)m’−NH−(CH2)m’−、−CO−(CH2)k−NH−(CH2)k−、−(NH−(CH2)m’) k−NH−、−CO−C3H6−(NH−C3H6)n−CO−、または−S−(CH2)m’−S−であり、m’は独立して1〜12の整数であり、kは1〜5の整数であり、nは1または2であり;
式(DI−4)において、sは独立して0〜2の整数であり;
式(DI−6)および式(DI−7)において、G22は独立して単結合、−O−、−S−、−CO−、−C(CH3)2−、−C(CF3)2−、−NH−、または炭素数1〜10のアルキレンであり;
式(DI−2)〜式(DI−7)において、シクロヘキサン環およびベンゼン環の少なくとも1つの水素は、−F、−Cl、炭素数1〜3のアルキル、−OCH3、−OH、−CF3、−CO2H、−CONH2、−NHC6H5、フェニル、またはベンジルで置き換えられてもよく、加えて式(DI−4)においてベンゼン環の少なくとも1つの水素は、下記式(DI−4−a)〜式(DI−4−e)で表される基の群から選ばれる1つで置き換えられていてもよく;
環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し、シクロヘキサン環またはベンゼン環への−NH2の結合位置は、G21またはG22の結合位置を除く任意の位置であり;
式(DI−8)〜式(DI−11)において、環に結合する−NH2の結合位置は、任意の位置であり;
式(DI−13)において、R23は独立して炭素数1〜5のアルキル、炭素数1〜5のアルコキシまたは−Clであり、pは独立して0〜3の整数であり、qは0〜4の整数であり;
式(DI−14)において、環Bは単環式複素芳香族であり、R24は水素、−F、−Cl、炭素数1〜6のアルキル、炭素数1〜6のアルコキシ、炭素数2〜6のアルケニル、炭素数2〜6のアルキニルであり、qは独立して0〜4の整数であり;
式(DI−15)において、環Cはヘテロ原子を含む単環であり;
式(DI−16)において、G24は単結合、炭素数2〜6のアルキレンまたは1,4−フェニレンであり、rは0または1であり;
式(DI−13)〜式(DI−16)において、環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
式(DIH−2)において、環Dはシクロヘキサン環、ベンゼン環またはナフタレン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく;
式(DIH−3)において、環Eはそれぞれ独立してシクロヘキサン環、またはベンゼン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく、Yは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(DIH−2)および式(DIH−3)において、環に結合する−CONHNH2の結合位置は、任意の位置であり;
R26は水素、−F、−OH、炭素数1〜30のアルキル、炭素数1〜30のフッ素置換アルキル、炭素数1〜30のアルコキシ、−CN、−OCH2F、−OCHF2、または−OCF3であり、この炭素数1〜30のアルキルの少なくとも1つの−CH2−は下記式(DI−31−b)で表される2価の基で置き換えられていてもよく、
式(DI−33)におけるベンゼン環の1つの水素は、炭素数1〜20のアルキルまたはフェニルで置き換えられてもよく、そして、
式(DI−32)および式(DI−33)において、環を構成するいずれかの炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
R31は水素または炭素数1〜20のアルキルであり、このアルキルの少なくとも1つの−CH2−は、−O−、−CH=CH−または−C≡C−で置き換えられてもよく、R32は炭素数6〜22のアルキルであり、R33は水素または炭素数1〜22のアルキルであり、環B25は1,4−フェニレンまたは1,4−シクロヘキシレンであり、rは0または1であり、そして、ベンゼン環に結合する−NH2はその環における結合位置が任意であることを示す。
[5] The tetracarboxylic dianhydride is at least one selected from the group of tetracarboxylic dianhydrides represented by the following formulas (AN-I) to (AN-VII);
Other diamines used together with the diamine represented by the formula (1) include the following formula (DI-1) to formula (DI-16), formula (DIH-1) to formula (DIH-3), and formula (DI The polyamic acid or derivative thereof according to any one of [1] to [4], which is at least one selected from the group consisting of -31) to formula (DI-35).
In Formula (AN-II), G is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C. (CF 3 ) 2 —;
In formula (AN-II) to formula (AN-IV), Y is independently one selected from the group of trivalent groups below,
In Formula (AN-III) to Formula (AN-V), Ring A 10 is a monocyclic hydrocarbon group having 3 to 10 carbon atoms or a condensed polycyclic hydrocarbon group having 6 to 30 carbon atoms, At least one hydrogen of this group may be replaced by methyl, ethyl or phenyl, and the bond on the ring is connected to any carbon constituting the ring, and the two bonds are the same. May be linked to carbon;
In the formula (AN-VI), X 10 is alkylene having 2 to 6 carbon atoms, Me represents methyl, Ph represents phenyl,
In formula (AN-VII), G 10 is independently —O—, —COO— or —OCO—; and r is independently 0 or 1;
In Formula (DI-3) and Formula (DI-5) to Formula (DI-7), G 21 is independently a single bond, —NH—, —NCH 3 —, —O—, —S—, —S. -S -, - SO 2 -, - CO -, - COO -, - CONH -, - CONCH 3 -, - C (CH 3) 2 -, - C (CF 3) 2 -, - (CH 2) m '-, - O- (CH 2 ) m' -O -, - N (CH 3) - (CH 2) k -N (CH 3) -, - (O-C 2 H 4) m '-O- , —O—CH 2 —C (CF 3 ) 2 —CH 2 —O—, —O—CO— (CH 2 ) m ′ —CO—O—, —CO—O— (CH 2 ) m ′ —O -CO -, - (CH 2) m '-NH- (CH 2) m' -, - CO- (CH 2) k -NH- (CH 2) k -, - (NH- (CH 2) m ' ) k -NH -, - CO- C 3 6 - (NH-C 3 H 6) n -CO-, or -S- (CH 2) m 'is -S-, m' is an integer from 1 to 12 independently, k is 1 to 5 And n is 1 or 2;
In formula (DI-4), s is independently an integer of 0 to 2;
In the formula (DI-6) and the formula (DI-7), G 22 is independently a single bond, —O—, —S—, —CO—, —C (CH 3 ) 2 —, —C (CF 3 2 ), -NH-, or alkylene having 1 to 10 carbons;
In formula (DI-2) ~ formula (DI-7), at least one hydrogen of cyclohexane ring and benzene ring, -F, -Cl, alkyl of 1 to 3 carbon atoms, -OCH 3, -OH, -CF 3 , —CO 2 H, —CONH 2 , —NHC 6 H 5 , phenyl, or benzyl, in addition, in formula (DI-4), at least one hydrogen of the benzene ring is represented by the following formula (DI -4-a) to one selected from the group of groups represented by formula (DI-4-e) may be substituted;
A group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary, and the bonding position of —NH 2 to the cyclohexane ring or the benzene ring is G 21 or G 22. Any position except the binding position of
In Formula (DI-8) to Formula (DI-11), the bonding position of —NH 2 bonded to the ring is an arbitrary position;
In the formula (DI-13), R 23 is independently alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons or —Cl, p is independently an integer of 0 to 3, and q is An integer from 0 to 4;
In the formula (DI-14), ring B is a monocyclic heteroaromatic, R 24 is hydrogen, —F, —Cl, alkyl having 1 to 6 carbons, alkoxy having 1 to 6 carbons, or carbon 2 6 alkenyl, alkynyl 2 to 6 carbon atoms, q is an integer of 0 to 4 independently;
In formula (DI-15), ring C is a monocycle containing a heteroatom;
In the formula (DI-16), G 24 is a single bond, alkylene having 2 to 6 carbons or 1,4-phenylene, and r is 0 or 1;
In formula (DI-13) to formula (DI-16), a group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
In formula (DIH-2), ring D is a cyclohexane ring, a benzene ring or a naphthalene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl;
In the formula (DIH-3), each ring E is independently a cyclohexane ring or a benzene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl, and Y is a single bond, An alkylene having 1 to 20 carbon atoms, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C (CF 3 ) 2 —;
In the formula (DIH-2) and the formula (DIH-3), the bonding position of -CONHNH 2 bonded to the ring is an arbitrary position;
R 26 is hydrogen, —F, —OH, alkyl having 1 to 30 carbons, fluorine-substituted alkyl having 1 to 30 carbons, alkoxy having 1 to 30 carbons, —CN, —OCH 2 F, —OCHF 2 , or is -OCF 3, at least one -CH 2 alkyl of 1 to 30 carbon atoms - may be replaced by a divalent group represented by the following formula (DI-31-b),
One hydrogen of the benzene ring in formula (DI-33) may be replaced by alkyl or phenyl having 1 to 20 carbon atoms, and
In formula (DI-32) and formula (DI-33), a group in which the bonding position is not fixed to any carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
R 31 is hydrogen or alkyl having 1 to 20 carbon atoms, and at least one —CH 2 — of the alkyl may be replaced by —O—, —CH═CH—, or —C≡C—. 32 is alkyl having 6 to 22 carbon atoms, R 33 is hydrogen or alkyl having 1 to 22 carbon atoms, ring B 25 is 1,4-phenylene or 1,4-cyclohexylene, and r is 0 or 1 and —NH 2 bonded to the benzene ring indicates that the bonding position in the ring is arbitrary.
[7] 反応に供されるテトラカルボン酸二無水物およびジアミンの少なくとも1つに光反応性構造を有する化合物を含む原料モノマーを反応させて得られる、[1]〜[6]のいずれか1項に記載のポリアミック酸またはその誘導体。 [ 7 ] Any one of [1] to [ 6 ] obtained by reacting a raw material monomer containing a compound having a photoreactive structure with at least one of tetracarboxylic dianhydride and diamine subjected to the reaction. Or a derivative thereof.
[8] 光反応性構造が下記式(P−1)〜式(P−7)で表される構造からなる群から選ばれる少なくとも1つである、[7]項に記載のポリアミック酸またはその誘導体。
[9] 光反応性構造を有する化合物が下記式(II−1)、式(II−2)、式(III−1)、式(III−2)、式(IV−1)、式(IV−2)、式(V−1)〜式(V−3)、および式(VI−1)、式(VI−2)からなる群から選ばれる少なくとも1つである、[7]項に記載のポリアミック酸またはその誘導体。
[10] 光反応性構造を有する化合物が下記式(PDI−7)で表されるジアミンである、[7]項に記載のポリアミック酸またはその誘導体。
[11] [1]〜[10]のいずれか1項に記載のポリアミック酸またはその誘導体を含有する液晶配向剤。 [ 11 ] A liquid crystal aligning agent containing the polyamic acid according to any one of [1] to [ 10 ] or a derivative thereof.
[12] ポリアミック酸またはその誘導体である重合体[A]および重合体[B]を含んでなる光配向用液晶配向剤であって;
前記重合体の原料モノマーの少なくとも1つが光反応性構造を有し、かつ、前記重合体の原料モノマーが下記式(1)で表される化合物の少なくとも1つを含む、光配向用液晶配向剤。
X1およびX2は、それぞれ独立して炭素数1〜8のアルキレンおよび/またはフェニレンを有する2価の有機基である。
[ 12 ] A liquid crystal aligning agent for photo-alignment comprising a polymer [A] and a polymer [B] which are polyamic acids or derivatives thereof;
A liquid crystal aligning agent for photo-alignment, wherein at least one of the raw material monomers of the polymer has a photoreactive structure, and the raw material monomer of the polymer contains at least one compound represented by the following formula (1) .
X 1 and X 2 are each independently a divalent organic group having 1 to 8 carbon atoms alkylene and / or phenylene.
[13] テトラカルボン酸二無水物およびジアミンからなる群から選ばれる少なくとも1つの光反応性構造を有する化合物を含む原料モノマーを反応させて得られる重合体[A]の少なくとも1つと、
テトラカルボン酸二無水物およびジアミンのいずれもが光反応性構造を有さず、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[B]の少なくとも1つを含む、[12]項に記載の光配向用液晶配向剤。
[ 13 ] at least one polymer [A] obtained by reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine;
Neither tetracarboxylic dianhydride nor diamine has a photoreactive structure, and a polymer obtained by reacting a raw material monomer containing at least one compound represented by formula (1) with diamine The liquid crystal aligning agent for photo-alignment according to item [ 12 ], comprising at least one of [B].
[14] テトラカルボン酸二無水物およびジアミンからなる群から選ばれる少なくとも1つの光反応性構造を有する化合物を含み、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[A]の少なくとも1つと、
テトラカルボン酸二無水物およびジアミンのいずれもが光反応性構造を有さない原料モノマーを反応させて得られる重合体[B]の少なくとも1つを含む、[12]項に記載の光配向用液晶配向剤。
[ 14 ] A raw material containing at least one compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and wherein the diamine contains at least one compound represented by formula (1) At least one of polymers [A] obtained by reacting monomers;
For photo-alignment according to item [ 12 ], including at least one polymer [B] obtained by reacting a raw material monomer in which both of tetracarboxylic dianhydride and diamine have no photoreactive structure Liquid crystal aligning agent.
[15] テトラカルボン酸二無水物およびジアミンからなる群から選ばれる少なくとも1つの光反応性構造を有する化合物を含み、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[A]の少なくとも1つと、
テトラカルボン酸二無水物およびジアミンのいずれもが光反応性構造を有さず、かつジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[B]を含む、[12]項に記載の光配向用液晶配向剤。
[ 15 ] A raw material containing at least one compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and wherein the diamine contains at least one compound represented by formula (1) At least one of polymers [A] obtained by reacting monomers;
Neither tetracarboxylic dianhydride nor diamine has a photoreactive structure, and a polymer obtained by reacting a raw material monomer containing at least one compound represented by formula (1) with diamine [ The liquid crystal aligning agent for photo-alignment according to item [12], including B].
[16] テトラカルボン酸二無水物およびジアミンからなる群から選ばれる少なくとも1つの光反応性構造を有する化合物を含み、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[A]の少なくとも1つと、
テトラカルボン酸二無水物およびジアミンからなる群から選ばれる少なくとも1つの光反応性構造を有する化合物を含み、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[B]の少なくとも1つを含む、[12]項に記載の光配向用液晶配向剤。
[ 16 ] A raw material containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and wherein the diamine contains at least one compound represented by formula (1) At least one of polymers [A] obtained by reacting monomers;
Reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and diamine containing at least one compound represented by formula (1) The liquid crystal aligning agent for photo-alignment as described in the item [ 12 ], comprising at least one of the polymer [B] obtained by the process.
[17] 式(1)で表されるジアミンが、式(1’)で表されるジアミンである、[12]〜[16]のいずれか1項に記載の光配向用液晶配向剤。
A1およびA2は、それぞれ独立して単結合または炭素数1〜6のアルキレンであり;そして、
環に結合する−NH2の結合位置は、任意の位置である。
[ 17 ] The liquid crystal aligning agent for photo-alignment according to any one of [ 12 ] to [ 16 ], wherein the diamine represented by the formula (1) is a diamine represented by the formula (1 ′).
A 1 and A 2 are each independently a single bond or alkylene having 1 to 6 carbons; and
The bonding position of —NH 2 bonded to the ring is an arbitrary position.
[18] 式(1)で表されるジアミンにおいて、Rが水素または−OHである、[12]〜[17]のいずれか1項に記載の光配向用液晶配向剤。 [ 18 ] The liquid crystal aligning agent for photo-alignment according to any one of [ 12 ] to [ 17 ], wherein in the diamine represented by the formula (1), R is hydrogen or -OH.
[19] 式(1)で表されるジアミンが、下記式(1−15)または式(1−29)で表される化合物である、[12]〜[18]のいずれか1項に記載の光配向用液晶配向剤。
[20] 光反応性構造を有する化合物が下記式(P−1)〜式(P−7)で表される構造の少なくとも1つを有する、[12]〜[19]のいずれか1項に記載の光配向用液晶配向剤。
[21] 光反応性構造を有する化合物が下記式(II−1)、式(II−2)、式(III−1)、式(III−2)、式(IV−1)、式(IV−2)、式(V−1)〜式(V−3)、および式(VI−1)、式(VI−2)からなる群から選ばれる少なくとも1つである、[12]〜[19]のいずれか1項に記載の光配向用液晶配向剤。
[22] 光反応性構造を有する化合物が下記式(PDI−7)で表されるジアミンである、[12]〜[19]のいずれか1項に記載の光反応用液晶配向剤。
[23] 光反応性構造を有さないテトラカルボン酸二無水物が、下記式(AN−I)〜式(AN−VII)で表されるテトラカルボン酸二無水物の群から選ばれる少なくとも1つであり;
光反応性構造を有さないジアミンが、下記式(DI−1)〜式(DI−16)、式(DIH−1)〜式(DIH−3)、および式(DI−31)〜式(DI−35)からなる群から選ばれる少なくとも1つである、[12]〜[22]のいずれか1項に記載の光配向用液晶配向剤。
式(AN−II)において、Gは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(AN−II)〜式(AN−IV)において、Yは独立して下記の3価の基の群から選ばれる1つであり、
式(AN−III)〜式(AN−V)において、環A10は炭素数3〜10の単環式炭化水素の基または炭素数6〜30の縮合多環式炭化水素の基であり、この基の少なくとも1つの水素はメチル、エチルまたはフェニルで置き換えられていてもよく、環に掛かっている結合手は環を構成する任意の炭素に連結しており、2本の結合手が同一の炭素に連結してもよく;
式(AN−VI)において、X10は炭素数2〜6のアルキレンであり、Meはメチルを表し、Phはフェニルを表し、
式(AN−VII)において、G10は独立して−O−、−COO−または−OCO−であり、rは独立して0または1であり;
式(DI−3)および式(DI−5)〜式(DI−7)において、G21は独立して単結合、−NH−、−NCH3−、−O−、−S−、−S−S−、−SO2−、−CO−、−COO−、−CONH−、−CONCH3−、−C(CH3)2−、−C(CF3)2−、−(CH2)m’−、−O−(CH2)m’−O−、−N(CH3)−(CH2)k−N(CH3)−、−(O−C2H4)m’−O−、−O−CH2−C(CF3)2−CH2−O−、−O−CO−(CH2)m’−CO−O−、−CO−O−(CH2)m’−O−CO−、−(CH2)m’−NH−(CH2)m’−、−CO−(CH2)k−NH−(CH2)k−、−(NH−(CH2)m’) k−NH−、−CO−C3H6−(NH−C3H6)n−CO−、または−S−(CH2)m’−S−であり、m’は独立して1〜12の整数であり、kは1〜5の整数であり、nは1または2であり;
式(DI−4)において、sは独立して0〜2の整数であり;
式(DI−6)および式(DI−7)において、G22は独立して単結合、−O−、−S−、−CO−、−C(CH3)2−、−C(CF3)2−、−NH−、または炭素数1〜10のアルキレンであり;
式(DI−2)〜式(DI−7)において、シクロヘキサン環およびベンゼン環の少なくとも1つの水素は、−F、−Cl、炭素数1〜3のアルキル、−OCH3、−OH、−CF3、−CO2H、−CONH2、−NHC6H5、フェニル、またはベンジルで置き換えられてもよく、加えて式(DI−4)においてベンゼン環の少なくとも1つの水素は、下記式(DI−4−a)〜式(DI−4−e)で表される基の群から選ばれる1つで置き換えられていてもよく;
環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し、シクロヘキサン環またはベンゼン環への−NH2の結合位置は、G21またはG22の結合位置を除く任意の位置であり;
式(DI−8)〜式(DI−11)において、環に結合する−NH2の結合位置は、任意の位置であり;
式(DI−13)において、R23は独立して炭素数1〜5のアルキル、炭素数1〜5のアルコキシまたは−Clであり、pは独立して0〜3の整数であり、qは0〜4の整数であり;
式(DI−14)において、環Bは単環式複素芳香族であり、R24は水素、−F、−Cl、炭素数1〜6のアルキル、炭素数1〜6のアルコキシ、炭素数2〜6のアルケニル、炭素数2〜6のアルキニルであり、qは独立して0〜4の整数であり;
式(DI−15)において、環Cはヘテロ原子を含む単環であり;
式(DI−16)において、G24は単結合、炭素数2〜6のアルキレンまたは1,4−フェニレンであり、rは0または1であり;
式(DI−13)〜式(DI−16)において、環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
式(DIH−2)において、環Dはシクロヘキサン環、ベンゼン環またはナフタレン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく;
式(DIH−3)において、環Eはそれぞれ独立してシクロヘキサン環、またはベンゼン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく、Yは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(DIH−2)および式(DIH−3)において、環に結合する−CONHNH2の結合位置は、任意の位置であり;
R26は水素、−F、−OH、炭素数1〜30のアルキル、炭素数1〜30のフッ素置換アルキル、炭素数1〜30のアルコキシ、−CN、−OCH2F、−OCHF2、または−OCF3であり、この炭素数1〜30のアルキルの少なくとも1つの−CH2−は下記式(DI−31−b)で表される2価の基で置き換えられていてもよく、
式(DI−33)におけるベンゼン環の1つの水素は、炭素数1〜20のアルキルまたはフェニルで置き換えられてもよく、そして、
式(DI−32)および式(DI−33)において、環を構成するいずれかの炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
R31は水素または炭素数1〜20のアルキルであり、このアルキルの少なくとも1つの−CH2−は、−O−、−CH=CH−または−C≡C−で置き換えられてもよく、R32は炭素数6〜22のアルキルであり、R33は水素または炭素数1〜22のアルキルであり、環B25は1,4−フェニレンまたは1,4−シクロヘキシレンであり、rは0または1であり、そして、ベンゼン環に結合する−NH2はその環における結合位置が任意であることを示す。
[ 23 ] The tetracarboxylic dianhydride having no photoreactive structure is at least one selected from the group of tetracarboxylic dianhydrides represented by the following formulas (AN-I) to (AN-VII). One;
Diamines having no photoreactive structure are represented by the following formulas (DI-1) to (DI-16), formulas (DIH-1) to (DIH-3), and formulas (DI-31) to ( The liquid crystal aligning agent for photo-alignment according to any one of [ 12 ] to [ 22 ], which is at least one selected from the group consisting of DI-35).
In Formula (AN-II), G is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C. (CF 3 ) 2 —;
In formula (AN-II) to formula (AN-IV), Y is independently one selected from the group of trivalent groups below,
In Formula (AN-III) to Formula (AN-V), Ring A 10 is a monocyclic hydrocarbon group having 3 to 10 carbon atoms or a condensed polycyclic hydrocarbon group having 6 to 30 carbon atoms, At least one hydrogen of this group may be replaced by methyl, ethyl or phenyl, and the bond on the ring is connected to any carbon constituting the ring, and the two bonds are the same. May be linked to carbon;
In the formula (AN-VI), X 10 is alkylene having 2 to 6 carbon atoms, Me represents methyl, Ph represents phenyl,
In formula (AN-VII), G 10 is independently —O—, —COO— or —OCO—, and r is independently 0 or 1;
In Formula (DI-3) and Formula (DI-5) to Formula (DI-7), G 21 is independently a single bond, —NH—, —NCH 3 —, —O—, —S—, —S. -S -, - SO 2 -, - CO -, - COO -, - CONH -, - CONCH 3 -, - C (CH 3) 2 -, - C (CF 3) 2 -, - (CH 2) m '-, - O- (CH 2 ) m' -O -, - N (CH 3) - (CH 2) k -N (CH 3) -, - (O-C 2 H 4) m '-O- , —O—CH 2 —C (CF 3 ) 2 —CH 2 —O—, —O—CO— (CH 2 ) m ′ —CO—O—, —CO—O— (CH 2 ) m ′ —O -CO -, - (CH 2) m '-NH- (CH 2) m' -, - CO- (CH 2) k -NH- (CH 2) k -, - (NH- (CH 2) m ' ) k -NH -, - CO- C 3 6 - (NH-C 3 H 6) n -CO-, or -S- (CH 2) m 'is -S-, m' is an integer from 1 to 12 independently, k is 1 to 5 And n is 1 or 2;
In formula (DI-4), s is independently an integer of 0 to 2;
In the formula (DI-6) and the formula (DI-7), G 22 is independently a single bond, —O—, —S—, —CO—, —C (CH 3 ) 2 —, —C (CF 3 2 ), -NH-, or alkylene having 1 to 10 carbons;
In formula (DI-2) ~ formula (DI-7), at least one hydrogen of cyclohexane ring and benzene ring, -F, -Cl, alkyl of 1 to 3 carbon atoms, -OCH 3, -OH, -CF 3 , —CO 2 H, —CONH 2 , —NHC 6 H 5 , phenyl, or benzyl, in addition, in formula (DI-4), at least one hydrogen of the benzene ring is represented by the following formula (DI -4-a) to one selected from the group of groups represented by formula (DI-4-e) may be substituted;
A group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary, and the bonding position of —NH 2 to the cyclohexane ring or the benzene ring is G 21 or G 22. Any position except the binding position of
In Formula (DI-8) to Formula (DI-11), the bonding position of —NH 2 bonded to the ring is an arbitrary position;
In the formula (DI-13), R 23 is independently alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons or —Cl, p is independently an integer of 0 to 3, and q is An integer from 0 to 4;
In the formula (DI-14), ring B is a monocyclic heteroaromatic, R 24 is hydrogen, —F, —Cl, alkyl having 1 to 6 carbons, alkoxy having 1 to 6 carbons, or carbon 2 6 alkenyl, alkynyl 2 to 6 carbon atoms, q is an integer of 0 to 4 independently;
In formula (DI-15), ring C is a monocycle containing a heteroatom;
In the formula (DI-16), G 24 is a single bond, alkylene having 2 to 6 carbons or 1,4-phenylene, and r is 0 or 1;
In formula (DI-13) to formula (DI-16), a group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
In formula (DIH-2), ring D is a cyclohexane ring, a benzene ring or a naphthalene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl;
In the formula (DIH-3), each ring E is independently a cyclohexane ring or a benzene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl, and Y is a single bond, An alkylene having 1 to 20 carbon atoms, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C (CF 3 ) 2 —;
In the formula (DIH-2) and the formula (DIH-3), the bonding position of -CONHNH 2 bonded to the ring is an arbitrary position;
R 26 is hydrogen, —F, —OH, alkyl having 1 to 30 carbons, fluorine-substituted alkyl having 1 to 30 carbons, alkoxy having 1 to 30 carbons, —CN, —OCH 2 F, —OCHF 2 , or is -OCF 3, at least one -CH 2 alkyl of 1 to 30 carbon atoms - may be replaced by a divalent group represented by the following formula (DI-31-b),
One hydrogen of the benzene ring in formula (DI-33) may be replaced by alkyl or phenyl having 1 to 20 carbon atoms, and
In formula (DI-32) and formula (DI-33), a group in which the bonding position is not fixed to any carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
R 31 is hydrogen or alkyl having 1 to 20 carbon atoms, and at least one —CH 2 — of the alkyl may be replaced by —O—, —CH═CH—, or —C≡C—. 32 is alkyl having 6 to 22 carbon atoms, R 33 is hydrogen or alkyl having 1 to 22 carbon atoms, ring B 25 is 1,4-phenylene or 1,4-cyclohexylene, and r is 0 or 1 and —NH 2 bonded to the benzene ring indicates that the bonding position in the ring is arbitrary.
[24] 光反応性構造を有さないテトラカルボン酸二無水物が、下記式(AN−1−1)、式(AN−1−2)、式(AN−1−13)、式(PA−1)、式(AN−3−1)、式(AN−3−2)、式(AN−4−5)、式(AN−4−17)、式(AN−4−21)、式(AN−4−29)、式(AN−4−30)、式(AN−5−1)、式(AN−7−2)、式(AN−10−1)、式(AN−11−3)、式(AN−16−1)、式(AN−16−3)、および式(AN−16−4)から選ばれる少なくとも1つであり;
光反応性構造を有さないジアミンが、下記式(DI−1−3)、式(DI−2−1)、式(DI−4−1)、式(DI−4−2)、式(DI−4−10)、式(DI−4−15)、式(DI−5−1)、式(DI−5−5)、式(DI−5−9)、式(DI−5−12)、式(DI−5−13)、式(DI−5−17)、式(DI−5−28)、式(DI−5−30)、式(DI−6−7)、式(DI−7−3)、式(DI−11−2)、式(DI−13−1)、式(DI−16−1)、式(DIH−2−1)、および式(DI−31−56)からなる群から選ばれる少なくとも1つである、[23]項に記載の光配向用液晶配向剤。
式(DI−5−30)において、kは1〜5の整数であり;そして、
式(DI−7−3)において、nはそれぞれ独立して1または2である。
[ 24 ] A tetracarboxylic dianhydride having no photoreactive structure is represented by the following formula (AN-1-1), formula (AN-1-2), formula (AN-1-13), formula (PA -1), formula (AN-3-1), formula (AN-3-2), formula (AN-4-5), formula (AN-4-17), formula (AN-4-21), formula (AN-4-29), Formula (AN-4-30), Formula (AN-5-1), Formula (AN-7-2), Formula (AN-10-1), Formula (AN-11- 3) at least one selected from formula (AN-16-1), formula (AN-16-3), and formula (AN-16-4);
A diamine having no photoreactive structure is represented by the following formula (DI-1-3), formula (DI-2-1), formula (DI-4-1), formula (DI-4-2), formula (DI DI-4-10), Formula (DI-4-15), Formula (DI-5-1), Formula (DI-5-5), Formula (DI-5-9), Formula (DI-5-12) ), Formula (DI-5-13), formula (DI-5-17), formula (DI-5-28), formula (DI-5-30), formula (DI-6-7), formula (DI -7-3), formula (DI-11-2), formula (DI-13-1), formula (DI-16-1), formula (DIH-2-1), and formula (DI-31-56) The liquid crystal aligning agent for photo-alignment according to item [ 23 ], which is at least one selected from the group consisting of:
In formula (DI-5-30), k is an integer from 1 to 5;
In formula (DI-7-3), each n is independently 1 or 2.
[25] オキサジン化合物、オキサゾリン化合物、エポキシ化合物、およびシランカップリング剤からなる化合物の群から選ばれる少なくとも1つをさらに含有する、[11]〜[24]のいずれか1項に記載の液晶配向剤。 [ 25 ] The liquid crystal alignment according to any one of [ 11 ] to [ 24 ], further containing at least one selected from the group consisting of an oxazine compound, an oxazoline compound, an epoxy compound, and a silane coupling agent. Agent.
[26] [11]〜[25]のいずれか1項に記載の液晶配向剤によって形成された液晶配向膜。 [ 26 ] A liquid crystal alignment film formed by the liquid crystal aligning agent according to any one of [ 11 ] to [ 25 ].
[27] [11]〜[25]のいずれか1項に記載の液晶配向剤によって形成された横電界用液晶配向膜。 [ 27 ] A liquid crystal alignment film for a horizontal electric field formed by the liquid crystal aligning agent according to any one of [ 11 ] to [ 25 ].
[28] [26]項または[27]項に記載の液晶配向膜を有する液晶表示素子。 [ 28 ] A liquid crystal display device having the liquid crystal alignment film according to the item [ 26 ] or [ 27 ].
[29] 式(1’)で表されるジアミン。
A1およびA2は、それぞれ独立して単結合または炭素数1〜6のアルキレンであり;そして、
環に結合する−NH2の結合位置は、任意の位置である。
[ 29 ] A diamine represented by the formula (1 ′).
A 1 and A 2 are each independently a single bond or alkylene having 1 to 6 carbons; and
The bonding position of —NH 2 bonded to the ring is an arbitrary position.
[30] 下記式(1−15)または式(1−29)で表される、[29]項に記載のジアミン。
Claims (30)
X1およびX2は、それぞれ独立して炭素数1〜8のアルキレンおよび/またはフェニレンを有する2価の有機基である。 A polyamic acid or a derivative thereof obtained by reacting a diamine containing at least one diamine represented by the formula (1) with tetracarboxylic dianhydride.
X 1 and X 2 are each independently a divalent organic group having 1 to 8 carbon atoms alkylene and / or phenylene.
A1およびA2は、それぞれ独立して単結合または炭素数1〜6のアルキレンであり;そして、
環に結合する−NH2の結合位置は、任意の位置である。 The polyamic acid or its derivative according to claim 1, wherein the diamine represented by the formula (1) is a diamine represented by the formula (1 ').
A 1 and A 2 are each independently a single bond or alkylene having 1 to 6 carbons; and
The bonding position of —NH 2 bonded to the ring is an arbitrary position.
式(1)で表されるジアミンと共に用いられるその他のジアミンが、下記式(DI−1)〜式(DI−16)、式(DIH−1)〜式(DIH−3)、および式(DI−31)〜式(DI−35)からなる群から選ばれる少なくとも1つである、請求項1〜4のいずれか1項に記載の、ポリアミック酸またはその誘導体。
式(AN−II)において、Gは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(AN−II)〜式(AN−IV)において、Yは独立して下記の3価の基の群から選ばれる1つであり、
式(AN−III)〜式(AN−V)において、環A10は炭素数3〜10の単環式炭化水素の基または炭素数6〜30の縮合多環式炭化水素の基であり、この基の少なくとも1つの水素はメチル、エチルまたはフェニルで置き換えられていてもよく、環に掛かっている結合手は環を構成する任意の炭素に連結しており、2本の結合手が同一の炭素に連結してもよく;
式(AN−VI)において、X10は炭素数2〜6のアルキレンであり、Meはメチルを表し、Phはフェニルを表し、
式(AN−VII)において、G10は独立して−O−、−COO−または−OCO−であり;そして、rは独立して0または1であり;
式(DI−3)および式(DI−5)〜式(DI−7)において、G21は独立して単結合、−NH−、−NCH3−、−O−、−S−、−S−S−、−SO2−、−CO−、−COO−、−CONH−、−CONCH3−、−C(CH3)2−、−C(CF3)2−、−(CH2)m’−、−O−(CH2)m’−O−、−N(CH3)−(CH2)k−N(CH3)−、−(O−C2H4)m’−O−、−O−CH2−C(CF3)2−CH2−O−、−O−CO−(CH2)m’−CO−O−、−CO−O−(CH2)m’−O−CO−、−(CH2)m’−NH−(CH2)m’−、−CO−(CH2)k−NH−(CH2)k−、−(NH−(CH2)m’) k−NH−、−CO−C3H6−(NH−C3H6)n−CO−、または−S−(CH2)m’−S−であり、m’は独立して1〜12の整数であり、kは1〜5の整数であり、nは1または2であり;
式(DI−4)において、sは独立して0〜2の整数であり;
式(DI−6)および式(DI−7)において、G22は独立して単結合、−O−、−S−、−CO−、−C(CH3)2−、−C(CF3)2−、−NH−、または炭素数1〜10のアルキレンであり;
式(DI−2)〜式(DI−7)において、シクロヘキサン環およびベンゼン環の少なくとも1つの水素は、−F、−Cl、炭素数1〜3のアルキル、−OCH3、−OH、−CF3、−CO2H、−CONH2、−NHC6H5、フェニル、またはベンジルで置き換えられてもよく、加えて式(DI−4)においてベンゼン環の少なくとも1つの水素は、下記式(DI−4−a)〜式(DI−4−e)で表される基の群から選ばれる1つで置き換えられていてもよく;
環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し、シクロヘキサン環またはベンゼン環への−NH2の結合位置は、G21またはG22の結合位置を除く任意の位置であり;
式(DI−8)〜式(DI−11)において、環に結合する−NH2の結合位置は、任意の位置であり;
式(DI−13)において、R23は独立して炭素数1〜5のアルキル、炭素数1〜5のアルコキシまたは−Clであり、pは独立して0〜3の整数であり、qは0〜4の整数であり;
式(DI−14)において、環Bは単環式複素芳香族であり、R24は水素、−F、−Cl、炭素数1〜6のアルキル、炭素数1〜6のアルコキシ、炭素数2〜6のアルケニル、炭素数2〜6のアルキニルであり、qは独立して0〜4の整数であり;
式(DI−15)において、環Cはヘテロ原子を含む単環であり;
式(DI−16)において、G24は単結合、炭素数2〜6のアルキレンまたは1,4−フェニレンであり、rは0または1であり;
式(DI−13)〜式(DI−16)において、環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
式(DIH−2)において、環Dはシクロヘキサン環、ベンゼン環またはナフタレン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく;
式(DIH−3)において、環Eはそれぞれ独立してシクロヘキサン環、またはベンゼン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく、Yは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(DIH−2)および式(DIH−3)において、環に結合する−CONHNH2の結合位置は、任意の位置であり;
R26は水素、−F、−OH、炭素数1〜30のアルキル、炭素数1〜30のフッ素置換アルキル、炭素数1〜30のアルコキシ、−CN、−OCH2F、−OCHF2、または−OCF3であり、この炭素数1〜30のアルキルの少なくとも1つの−CH2−は下記式(DI−31−b)で表される2価の基で置き換えられていてもよく、
式(DI−33)におけるベンゼン環の1つの水素は、炭素数1〜20のアルキルまたはフェニルで置き換えられてもよく、そして、
式(DI−32)および式(DI−33)において、環を構成するいずれかの炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
R31は水素または炭素数1〜20のアルキルであり、このアルキルの少なくとも1つの−CH2−は、−O−、−CH=CH−または−C≡C−で置き換えられてもよく、R32は炭素数6〜22のアルキルであり、R33は水素または炭素数1〜22のアルキルであり、環B25は1,4−フェニレンまたは1,4−シクロヘキシレンであり、rは0または1であり、そして、ベンゼン環に結合する−NH2はその環における結合位置が任意であることを示す。 The tetracarboxylic dianhydride is at least one selected from the group of tetracarboxylic dianhydrides represented by the following formulas (AN-I) to (AN-VII);
Other diamines used together with the diamine represented by the formula (1) include the following formula (DI-1) to formula (DI-16), formula (DIH-1) to formula (DIH-3), and formula (DI The polyamic acid or derivative thereof according to any one of claims 1 to 4, which is at least one selected from the group consisting of -31) to formula (DI-35).
In Formula (AN-II), G is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C. (CF 3 ) 2 —;
In formula (AN-II) to formula (AN-IV), Y is independently one selected from the group of trivalent groups below,
In Formula (AN-III) to Formula (AN-V), Ring A 10 is a monocyclic hydrocarbon group having 3 to 10 carbon atoms or a condensed polycyclic hydrocarbon group having 6 to 30 carbon atoms, At least one hydrogen of this group may be replaced by methyl, ethyl or phenyl, and the bond on the ring is connected to any carbon constituting the ring, and the two bonds are the same. May be linked to carbon;
In the formula (AN-VI), X 10 is alkylene having 2 to 6 carbon atoms, Me represents methyl, Ph represents phenyl,
In formula (AN-VII), G 10 is independently —O—, —COO— or —OCO—; and r is independently 0 or 1;
In Formula (DI-3) and Formula (DI-5) to Formula (DI-7), G 21 is independently a single bond, —NH—, —NCH 3 —, —O—, —S—, —S. -S -, - SO 2 -, - CO -, - COO -, - CONH -, - CONCH 3 -, - C (CH 3) 2 -, - C (CF 3) 2 -, - (CH 2) m '-, - O- (CH 2 ) m' -O -, - N (CH 3) - (CH 2) k -N (CH 3) -, - (O-C 2 H 4) m '-O- , —O—CH 2 —C (CF 3 ) 2 —CH 2 —O—, —O—CO— (CH 2 ) m ′ —CO—O—, —CO—O— (CH 2 ) m ′ —O -CO -, - (CH 2) m '-NH- (CH 2) m' -, - CO- (CH 2) k -NH- (CH 2) k -, - (NH- (CH 2) m ' ) k -NH -, - CO- C 3 6 - (NH-C 3 H 6) n -CO-, or -S- (CH 2) m 'is -S-, m' is an integer from 1 to 12 independently, k is 1 to 5 And n is 1 or 2;
In formula (DI-4), s is independently an integer of 0 to 2;
In the formula (DI-6) and the formula (DI-7), G 22 is independently a single bond, —O—, —S—, —CO—, —C (CH 3 ) 2 —, —C (CF 3 2 ), -NH-, or alkylene having 1 to 10 carbons;
In formula (DI-2) ~ formula (DI-7), at least one hydrogen of cyclohexane ring and benzene ring, -F, -Cl, alkyl of 1 to 3 carbon atoms, -OCH 3, -OH, -CF 3 , —CO 2 H, —CONH 2 , —NHC 6 H 5 , phenyl, or benzyl, in addition, in formula (DI-4), at least one hydrogen of the benzene ring is represented by the following formula (DI -4-a) to one selected from the group of groups represented by formula (DI-4-e) may be substituted;
A group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary, and the bonding position of —NH 2 to the cyclohexane ring or the benzene ring is G 21 or G 22. Any position except the binding position of
In Formula (DI-8) to Formula (DI-11), the bonding position of —NH 2 bonded to the ring is an arbitrary position;
In the formula (DI-13), R 23 is independently alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons or —Cl, p is independently an integer of 0 to 3, and q is An integer from 0 to 4;
In the formula (DI-14), ring B is a monocyclic heteroaromatic, R 24 is hydrogen, —F, —Cl, alkyl having 1 to 6 carbons, alkoxy having 1 to 6 carbons, or carbon 2 6 alkenyl, alkynyl 2 to 6 carbon atoms, q is an integer of 0 to 4 independently;
In formula (DI-15), ring C is a monocycle containing a heteroatom;
In the formula (DI-16), G 24 is a single bond, alkylene having 2 to 6 carbons or 1,4-phenylene, and r is 0 or 1;
In formula (DI-13) to formula (DI-16), a group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
In formula (DIH-2), ring D is a cyclohexane ring, a benzene ring or a naphthalene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl;
In the formula (DIH-3), each ring E is independently a cyclohexane ring or a benzene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl, and Y is a single bond, An alkylene having 1 to 20 carbon atoms, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C (CF 3 ) 2 —;
In the formula (DIH-2) and the formula (DIH-3), the bonding position of -CONHNH 2 bonded to the ring is an arbitrary position;
R 26 is hydrogen, —F, —OH, alkyl having 1 to 30 carbons, fluorine-substituted alkyl having 1 to 30 carbons, alkoxy having 1 to 30 carbons, —CN, —OCH 2 F, —OCHF 2 , or is -OCF 3, at least one -CH 2 alkyl of 1 to 30 carbon atoms - may be replaced by a divalent group represented by the following formula (DI-31-b),
One hydrogen of the benzene ring in formula (DI-33) may be replaced by alkyl or phenyl having 1 to 20 carbon atoms, and
In formula (DI-32) and formula (DI-33), a group in which the bonding position is not fixed to any carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
R 31 is hydrogen or alkyl having 1 to 20 carbon atoms, and at least one —CH 2 — of the alkyl may be replaced by —O—, —CH═CH—, or —C≡C—. 32 is alkyl having 6 to 22 carbon atoms, R 33 is hydrogen or alkyl having 1 to 22 carbon atoms, ring B 25 is 1,4-phenylene or 1,4-cyclohexylene, and r is 0 or 1 and —NH 2 bonded to the benzene ring indicates that the bonding position in the ring is arbitrary.
式(1)で表されるジアミンと共に用いられるその他のジアミンが、下記式(DI−1−3)、式(DI−2−1)、式(DI−4−1)、式(DI−4−2)、式(DI−4−10)、式(DI−4−15)、式(DI−5−1)、式(DI−5−5)、式(DI−5−9)、式(DI−5−12)、式(DI−5−13)、式(DI−5−17)、式(DI−5−28)、式(DI−5−30)、式(DI−6−7)、式(DI−7−3)、式(DI−11−2)、式(DI−13−1)、式(DI−16−1)、式(DIH−2−1)、および式(DI−31−56)からなる群から選ばれる少なくとも1つである、請求項5に記載のポリアミック酸またはその誘導体。
式(DI−5−30)において、kは1〜5の整数であり;そして、
式(DI−7−3)において、nは1または2である。 Tetracarboxylic dianhydride has the following formula (AN-1-1), formula (AN-1-2), formula (AN-1-13), formula (PA-1), formula (AN-3-1) ), Formula (AN-3-2), formula (AN-4-5), formula (AN-4-17), formula (AN-4-21), formula (AN-4-29), formula (AN -4-30), formula (AN-5-1), formula (AN-7-2), formula (AN-10-1), formula (AN-11-3), formula (AN-16-1) At least one selected from formula (AN-16-3) and formula (AN-16-4);
Other diamines used together with the diamine represented by the formula (1) include the following formula (DI-1-3), formula (DI-2-1), formula (DI-4-1), formula (DI-4) -2), formula (DI-4-10), formula (DI-4-15), formula (DI-5-1), formula (DI-5-5), formula (DI-5-9), formula (DI-5-12), Formula (DI-5-13), Formula (DI-5-17), Formula (DI-5-28), Formula (DI-5-30), Formula (DI-6-6) 7), Formula (DI-7-3), Formula (DI-11-2), Formula (DI-13-1), Formula (DI-16-1), Formula (DIH-2-1), and Formula The polyamic acid or derivative thereof according to claim 5, which is at least one selected from the group consisting of (DI-31-56).
In formula (DI-5-30), k is an integer from 1 to 5;
In the formula (DI-7-3), n is 1 or 2.
前記重合体の原料モノマーの少なくとも1つが光反応性構造を有し、かつ、前記重合体の原料モノマーが下記式(1)で表される化合物の少なくとも1つを含む、光配向用液晶配向剤。
X1およびX2は、それぞれ独立して炭素数1〜8のアルキレンおよび/またはフェニレンを有する2価の有機基である。 A liquid crystal aligning agent for photoalignment comprising a polymer [A] and a polymer [B] which are polyamic acids or derivatives thereof;
A liquid crystal aligning agent for photo-alignment, wherein at least one of the raw material monomers of the polymer has a photoreactive structure, and the raw material monomer of the polymer contains at least one compound represented by the following formula (1) .
X 1 and X 2 are each independently a divalent organic group having 1 to 8 carbon atoms alkylene and / or phenylene.
テトラカルボン酸二無水物およびジアミンのいずれもが光反応性構造を有さず、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[B]の少なくとも1つを含む、請求項12に記載の光配向用液晶配向剤。 At least one polymer [A] obtained by reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine;
Neither tetracarboxylic dianhydride nor diamine has a photoreactive structure, and a polymer obtained by reacting a raw material monomer containing at least one compound represented by formula (1) with diamine The liquid crystal aligning agent for photo-alignment of Claim 12 containing at least 1 of [B].
テトラカルボン酸二無水物およびジアミンのいずれもが光反応性構造を有さない原料モノマーを反応させて得られる重合体[B]の少なくとも1つを含む、請求項12に記載の光配向用液晶配向剤。 Reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and diamine containing at least one compound represented by formula (1) At least one of the polymers [A] obtained by
The liquid crystal for photo-alignment according to claim 12 , comprising at least one polymer [B] obtained by reacting a raw material monomer in which both tetracarboxylic dianhydride and diamine have no photoreactive structure. Alignment agent.
テトラカルボン酸二無水物およびジアミンのいずれもが光反応性構造を有さず、かつジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[B]を含む、請求項12に記載の光配向用液晶配向剤。 Reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and diamine containing at least one compound represented by formula (1) At least one of the polymers [A] obtained by
Neither tetracarboxylic dianhydride nor diamine has a photoreactive structure, and a polymer obtained by reacting a raw material monomer containing at least one compound represented by formula (1) with diamine [ The liquid crystal aligning agent for photo-alignment of Claim 12 containing B].
テトラカルボン酸二無水物およびジアミンからなる群から選ばれる少なくとも1つの光反応性構造を有する化合物を含み、かつ、ジアミンが式(1)で表される化合物の少なくとも1つを含む原料モノマーを反応させて得られる重合体[B]の少なくとも1つを含む、請求項12に記載の光配向用液晶配向剤。 Reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and diamine containing at least one compound represented by formula (1) At least one of the polymers [A] obtained by
Reacting a raw material monomer containing a compound having at least one photoreactive structure selected from the group consisting of tetracarboxylic dianhydride and diamine, and diamine containing at least one compound represented by formula (1) The liquid crystal aligning agent for photo-alignment of Claim 12 containing at least 1 of the polymer [B] obtained by making it carry out.
A1およびA2は、それぞれ独立して単結合または炭素数1〜6のアルキレンであり;そして、
環に結合する−NH2の結合位置は、任意の位置である。 Diamine represented by the formula (1) is a diamine of the formula (1 '), a liquid crystal aligning agent for optical alignment as claimed in any one of claims 12 to 16.
A 1 and A 2 are each independently a single bond or alkylene having 1 to 6 carbons; and
The bonding position of —NH 2 bonded to the ring is an arbitrary position.
光反応性構造を有さないジアミンが、下記式(DI−1)〜式(DI−16)、式(DIH−1)〜式(DIH−3)、および式(DI−31)〜式(DI−35)からなる群から選ばれる少なくとも1つである、請求項12〜22のいずれか1項に記載の光配向用液晶配向剤。
式(AN−II)において、Gは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(AN−II)〜式(AN−IV)において、Yは独立して下記の3価の基の群から選ばれる1つであり、
式(AN−III)〜式(AN−V)において、環A10は炭素数3〜10の単環式炭化水素の基または炭素数6〜30の縮合多環式炭化水素の基であり、この基の少なくとも1つの水素はメチル、エチルまたはフェニルで置き換えられていてもよく、環に掛かっている結合手は環を構成する任意の炭素に連結しており、2本の結合手が同一の炭素に連結してもよく;
式(AN−VI)において、X10は炭素数2〜6のアルキレンであり、Meはメチルを表し、Phはフェニルを表し、
式(AN−VII)において、G10は独立して−O−、−COO−または−OCO−であり、rは独立して0または1であり;
式(DI−3)および式(DI−5)〜式(DI−7)において、G21は独立して単結合、−NH−、−NCH3−、−O−、−S−、−S−S−、−SO2−、−CO−、−COO−、−CONH−、−CONCH3−、−C(CH3)2−、−C(CF3)2−、−(CH2)m’−、−O−(CH2)m’−O−、−N(CH3)−(CH2)k−N(CH3)−、−(O−C2H4)m’−O−、−O−CH2−C(CF3)2−CH2−O−、−O−CO−(CH2)m’−CO−O−、−CO−O−(CH2)m’−O−CO−、−(CH2)m’−NH−(CH2)m’−、−CO−(CH2)k−NH−(CH2)k−、−(NH−(CH2)m’) k−NH−、−CO−C3H6−(NH−C3H6)n−CO−、または−S−(CH2)m’−S−であり、m’は独立して1〜12の整数であり、kは1〜5の整数であり、nは1または2であり;
式(DI−4)において、sは独立して0〜2の整数であり;
式(DI−6)および式(DI−7)において、G22は独立して単結合、−O−、−S−、−CO−、−C(CH3)2−、−C(CF3)2−、−NH−、または炭素数1〜10のアルキレンであり;
式(DI−2)〜式(DI−7)において、シクロヘキサン環およびベンゼン環の少なくとも1つの水素は、−F、−Cl、炭素数1〜3のアルキル、−OCH3、−OH、−CF3、−CO2H、−CONH2、−NHC6H5、フェニル、またはベンジルで置き換えられてもよく、加えて式(DI−4)においてベンゼン環の少なくとも1つの水素は、下記式(DI−4−a)〜式(DI−4−e)で表される基の群から選ばれる1つで置き換えられていてもよく;
環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し、シクロヘキサン環またはベンゼン環への−NH2の結合位置は、G21またはG22の結合位置を除く任意の位置であり;
式(DI−8)〜式(DI−11)において、環に結合する−NH2の結合位置は、任意の位置であり;
式(DI−13)において、R23は独立して炭素数1〜5のアルキル、炭素数1〜5のアルコキシまたは−Clであり、pは独立して0〜3の整数であり、qは0〜4の整数であり;
式(DI−14)において、環Bは単環式複素芳香族であり、R24は水素、−F、−Cl、炭素数1〜6のアルキル、炭素数1〜6のアルコキシ、炭素数2〜6のアルケニル、炭素数2〜6のアルキニルであり、qは独立して0〜4の整数であり;
式(DI−15)において、環Cはヘテロ原子を含む単環であり;
式(DI−16)において、G24は単結合、炭素数2〜6のアルキレンまたは1,4−フェニレンであり、rは0または1であり;
式(DI−13)〜式(DI−16)において、環を構成する炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
式(DIH−2)において、環Dはシクロヘキサン環、ベンゼン環またはナフタレン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく;
式(DIH−3)において、環Eはそれぞれ独立してシクロヘキサン環、またはベンゼン環であり、この環の少なくとも1つの水素はメチル、エチル、またはフェニルで置き換えられてもよく、Yは単結合、炭素数1〜20のアルキレン、−CO−、−O−、−S−、−SO2−、−C(CH3)2−、または−C(CF3)2−であり;
式(DIH−2)および式(DIH−3)において、環に結合する−CONHNH2の結合位置は、任意の位置であり;
R26は水素、−F、−OH、炭素数1〜30のアルキル、炭素数1〜30のフッ素置換アルキル、炭素数1〜30のアルコキシ、−CN、−OCH2F、−OCHF2、または−OCF3であり、この炭素数1〜30のアルキルの少なくとも1つの−CH2−は下記式(DI−31−b)で表される2価の基で置き換えられていてもよく、
式(DI−33)におけるベンゼン環の1つの水素は、炭素数1〜20のアルキルまたはフェニルで置き換えられてもよく、そして、
式(DI−32)および式(DI−33)において、環を構成するいずれかの炭素原子に結合位置が固定されていない基は、その環における結合位置が任意であることを示し;
R31は水素または炭素数1〜20のアルキルであり、このアルキルの少なくとも1つの−CH2−は、−O−、−CH=CH−または−C≡C−で置き換えられてもよく、R32は炭素数6〜22のアルキルであり、R33は水素または炭素数1〜22のアルキルであり、環B25は1,4−フェニレンまたは1,4−シクロヘキシレンであり、rは0または1であり、そして、ベンゼン環に結合する−NH2はその環における結合位置が任意であることを示す。 The tetracarboxylic dianhydride having no photoreactive structure is at least one selected from the group of tetracarboxylic dianhydrides represented by the following formulas (AN-I) to (AN-VII): ;
Diamines having no photoreactive structure are represented by the following formulas (DI-1) to (DI-16), formulas (DIH-1) to (DIH-3), and formulas (DI-31) to ( The liquid crystal aligning agent for photo-alignment according to any one of claims 12 to 22 , which is at least one selected from the group consisting of DI-35).
In Formula (AN-II), G is a single bond, alkylene having 1 to 20 carbons, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C. (CF 3 ) 2 —;
In formula (AN-II) to formula (AN-IV), Y is independently one selected from the group of trivalent groups below,
In Formula (AN-III) to Formula (AN-V), Ring A 10 is a monocyclic hydrocarbon group having 3 to 10 carbon atoms or a condensed polycyclic hydrocarbon group having 6 to 30 carbon atoms, At least one hydrogen of this group may be replaced by methyl, ethyl or phenyl, and the bond on the ring is connected to any carbon constituting the ring, and the two bonds are the same. May be linked to carbon;
In the formula (AN-VI), X 10 is alkylene having 2 to 6 carbon atoms, Me represents methyl, Ph represents phenyl,
In formula (AN-VII), G 10 is independently —O—, —COO— or —OCO—, and r is independently 0 or 1;
In Formula (DI-3) and Formula (DI-5) to Formula (DI-7), G 21 is independently a single bond, —NH—, —NCH 3 —, —O—, —S—, —S. -S -, - SO 2 -, - CO -, - COO -, - CONH -, - CONCH 3 -, - C (CH 3) 2 -, - C (CF 3) 2 -, - (CH 2) m '-, - O- (CH 2 ) m' -O -, - N (CH 3) - (CH 2) k -N (CH 3) -, - (O-C 2 H 4) m '-O- , —O—CH 2 —C (CF 3 ) 2 —CH 2 —O—, —O—CO— (CH 2 ) m ′ —CO—O—, —CO—O— (CH 2 ) m ′ —O -CO -, - (CH 2) m '-NH- (CH 2) m' -, - CO- (CH 2) k -NH- (CH 2) k -, - (NH- (CH 2) m ' ) k -NH -, - CO- C 3 6 - (NH-C 3 H 6) n -CO-, or -S- (CH 2) m 'is -S-, m' is an integer from 1 to 12 independently, k is 1 to 5 And n is 1 or 2;
In formula (DI-4), s is independently an integer of 0 to 2;
In the formula (DI-6) and the formula (DI-7), G 22 is independently a single bond, —O—, —S—, —CO—, —C (CH 3 ) 2 —, —C (CF 3 2 ), -NH-, or alkylene having 1 to 10 carbons;
In formula (DI-2) ~ formula (DI-7), at least one hydrogen of cyclohexane ring and benzene ring, -F, -Cl, alkyl of 1 to 3 carbon atoms, -OCH 3, -OH, -CF 3 , —CO 2 H, —CONH 2 , —NHC 6 H 5 , phenyl, or benzyl, in addition, in formula (DI-4), at least one hydrogen of the benzene ring is represented by the following formula (DI -4-a) to one selected from the group of groups represented by formula (DI-4-e) may be substituted;
A group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary, and the bonding position of —NH 2 to the cyclohexane ring or the benzene ring is G 21 or G 22. Any position except the binding position of
In Formula (DI-8) to Formula (DI-11), the bonding position of —NH 2 bonded to the ring is an arbitrary position;
In the formula (DI-13), R 23 is independently alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons or —Cl, p is independently an integer of 0 to 3, and q is An integer from 0 to 4;
In the formula (DI-14), ring B is a monocyclic heteroaromatic, R 24 is hydrogen, —F, —Cl, alkyl having 1 to 6 carbons, alkoxy having 1 to 6 carbons, or carbon 2 6 alkenyl, alkynyl 2 to 6 carbon atoms, q is an integer of 0 to 4 independently;
In formula (DI-15), ring C is a monocycle containing a heteroatom;
In the formula (DI-16), G 24 is a single bond, alkylene having 2 to 6 carbons or 1,4-phenylene, and r is 0 or 1;
In formula (DI-13) to formula (DI-16), a group in which the bonding position is not fixed to the carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
In formula (DIH-2), ring D is a cyclohexane ring, a benzene ring or a naphthalene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl;
In the formula (DIH-3), each ring E is independently a cyclohexane ring or a benzene ring, and at least one hydrogen of the ring may be replaced with methyl, ethyl, or phenyl, and Y is a single bond, An alkylene having 1 to 20 carbon atoms, —CO—, —O—, —S—, —SO 2 —, —C (CH 3 ) 2 —, or —C (CF 3 ) 2 —;
In the formula (DIH-2) and the formula (DIH-3), the bonding position of -CONHNH 2 bonded to the ring is an arbitrary position;
R 26 is hydrogen, —F, —OH, alkyl having 1 to 30 carbons, fluorine-substituted alkyl having 1 to 30 carbons, alkoxy having 1 to 30 carbons, —CN, —OCH 2 F, —OCHF 2 , or is -OCF 3, at least one -CH 2 alkyl of 1 to 30 carbon atoms - may be replaced by a divalent group represented by the following formula (DI-31-b),
One hydrogen of the benzene ring in formula (DI-33) may be replaced by alkyl or phenyl having 1 to 20 carbon atoms, and
In formula (DI-32) and formula (DI-33), a group in which the bonding position is not fixed to any carbon atom constituting the ring indicates that the bonding position in the ring is arbitrary;
R 31 is hydrogen or alkyl having 1 to 20 carbon atoms, and at least one —CH 2 — of the alkyl may be replaced by —O—, —CH═CH—, or —C≡C—. 32 is alkyl having 6 to 22 carbon atoms, R 33 is hydrogen or alkyl having 1 to 22 carbon atoms, ring B 25 is 1,4-phenylene or 1,4-cyclohexylene, and r is 0 or 1 and —NH 2 bonded to the benzene ring indicates that the bonding position in the ring is arbitrary.
光反応性構造を有さないジアミンが、下記式(DI−1−3)、式(DI−2−1)、式(DI−4−1)、式(DI−4−2)、式(DI−4−10)、式(DI−4−15)、式(DI−5−1)、式(DI−5−5)、式(DI−5−9)、式(DI−5−12)、式(DI−5−13)、式(DI−5−17)、式(DI−5−28)、式(DI−5−30)、式(DI−6−7)、式(DI−7−3)、式(DI−11−2)、式(DI−13−1)、式(DI−16−1)、式(DIH−2−1)、および式(DI−31−56)からなる群から選ばれる少なくとも1つである、請求項23に記載の光配向用液晶配向剤。
式(DI−5−30)において、kは1〜5の整数であり;そして、
式(DI−7−3)において、nはそれぞれ独立して1または2である。 A tetracarboxylic dianhydride having no photoreactive structure is represented by the following formula (AN-1-1), formula (AN-1-2), formula (AN-1-13), formula (PA-1). , Formula (AN-3-1), Formula (AN-3-2), Formula (AN-4-5), Formula (AN-4-17), Formula (AN-4-21), Formula (AN- 4-29), Formula (AN-4-30), Formula (AN-5-1), Formula (AN-7-2), Formula (AN-10-1), Formula (AN-11-3), At least one selected from Formula (AN-16-1), Formula (AN-16-3), and Formula (AN-16-4);
A diamine having no photoreactive structure is represented by the following formula (DI-1-3), formula (DI-2-1), formula (DI-4-1), formula (DI-4-2), formula (DI DI-4-10), Formula (DI-4-15), Formula (DI-5-1), Formula (DI-5-5), Formula (DI-5-9), Formula (DI-5-12) ), Formula (DI-5-13), formula (DI-5-17), formula (DI-5-28), formula (DI-5-30), formula (DI-6-7), formula (DI -7-3), formula (DI-11-2), formula (DI-13-1), formula (DI-16-1), formula (DIH-2-1), and formula (DI-31-56) The liquid crystal aligning agent for photo-alignment according to claim 23 , which is at least one selected from the group consisting of:
In formula (DI-5-30), k is an integer from 1 to 5;
In formula (DI-7-3), each n is independently 1 or 2.
A1およびA2は、それぞれ独立して単結合または炭素数1〜6のアルキレンであり;そして、
環に結合する−NH2の結合位置は、任意の位置である。 Diamine represented by Formula (1 ').
A 1 and A 2 are each independently a single bond or alkylene having 1 to 6 carbons; and
The bonding position of —NH 2 bonded to the ring is an arbitrary position.
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