LIQUID CRYSTAL DISPLAY DEVICE AND METHOD FOR MANUFACTURING SAME

1 . A liquid crystal display device comprising:

a first substrate;

a second substrate;

a photoalignment film provided on at least one of the first and second substrates;

a polymer layer provided on the photoalignment film; and

a liquid crystal layer provided between the first and second substrates,

the polymer layer containing a polymer having a monomer unit derived from two or more kinds of polymerizable monomers,

the two or more kinds of polymerizable monomers including at least a polymerizable monomer represented by Formula (I):

wherein A 1 and A 2 may be the same as or different from each other and each represent a benzene ring, biphenyl ring, or C1-C12 linear or branched alkyl or alkenyl group,

one of A 1 and A 2 represents a benzene or biphenyl ring,

at least one of A 1 and A 2 include a -Sp 1 -P 1 group,

a hydrogen atom on A 1 and A 2 may be replaced by a -Sp 1 -P 1 group, halogen atom, —CN group, —NO 2 group, —NCO group, —NCS group, —OCN group, —SCN group, —SF 5 group, or C1-C12 linear or branched alkyl, alkenyl, or aralkyl group,

two hydrogen atoms bonded to two adjacent carbons in A 1 and A 2 may be replaced by a C1-C12 linear or branched alkylene or alkenylene group to form a ring structure,

a hydrogen atom on the alkyl, alkenyl, alkylene, alkenylene, or aralkyl group in A 1 and A 2 may be replaced by a -Sp 1 -P 1 group,

a —CH 2 — group on the alkyl, alkenyl, alkylene, alkenylene, or aralkyl group in A 1 and A 2 may be substituted with a —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group, provided that oxygen, sulfur, and nitrogen atoms are not adjacent to one another,

P 1 represents a polymerizable group,

Sp 1 represents a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group or a direct bond,

m represents 1 or 2,

a dotted line between A 1 and Y and a dotted line between A 2 and Y represent an optional bond between A 1 and A 2 via Y, and

Y represents a —CH 2 —, —CH 2 CH 2 —, —CH═CH—, —O—, —S—, —NH—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —OCH 2 —, —CH 2 O—, —SCH 2 —, or —CH 2 S— group or a direct bond; and

a polymerizable monomer represented by Formula (II):

P 3 —S 3 -A 3 -(Z 3 -A 4 ) n -S 4 —P 4   (II)

wherein

P 3 and P 4 may be the same as or different from each other, and each represent an acryloyloxy, methacryloyloxy, acryloylamino, methacryloylamino, vinyl, or vinyloxy group,

A 3 and A 4 may be the same as or different from each other, and each represent a 1,4-phenylene, 4,4′-biphenyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, phenanthrene-3,6-diyl, phenanthrene-3,8-diyl, or phenanthrene-1,8-diyl group,

Z 3 may be the same as or different from each other, and each represent a —COO—, —OCO—, —O—, —CO—, —NHCO—, —CONH—, or —S— group or a direct bond between A 3 and A 4 or between A 4 and A 4 ,

n represents 0, 1, 2, or 3,

S 3 and S 4 may be the same as or different from each other, and each represent a —(CH 2 ) m — group (m representing a natural number satisfying 1≦m≦6), a —(CH 2 —CH 2 —O) m — group (m representing a natural number satisfying 1≦m≦6), or a direct bond between P 3 and A 3 , between A 3 and P 4 , or between A 4 and P 4 , and

a hydrogen atom on A 3 and A 4 may be replaced by a halogen or methyl group.

2 . The liquid crystal display device according to claim 1 ,

wherein the polymerizable monomer represented by Formula (I) is a polymerizable monomer represented by any one of Formulae (I-1) to (I-6) mentioned below;

wherein

R 1 and R 2 may be the same as or different from each other, and each represent a -Sp 1 -P 1 group, hydrogen atom, halogen atom, —CN group, —NO 2 group, —NCO group, —NCS group, —OCN group, —SCN group, —SF 5 group, C1-C12 linear or branched alkyl or aralkyl group, phenyl group, or biphenyl group,

at least one of R 1 and R 2 have a -Sp 1 -P 1 group,

P 1 represents an acryloyloxy, methacryloyloxy, vinyl, vinyloxy, acryloylamino, methacryloylamino group,

Sp 1 represents a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group or a direct bond,

when R 1 and R 2 each represent a phenyl, biphenyl, or C1-C12 linear or branched alkyl or aralkyl group, a hydrogen atom on R 1 and R 2 may be replaced by a fluorine atom, chlorine atom, or -Sp 1 -P 1 group, and

a —CH 2 — group on R 1 and R 2 may be substituted with a —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group, provided that oxygen, sulfur, and nitrogen atoms are not adjacent to one another.

3 . The liquid crystal display according to claim 1 ,

wherein the polymerizable monomer represented by Formula (I) is a polymerizable monomer represented by any of Formulae (I-7) to (I-8) mentioned below;

wherein

R 1 and R 2 may be the same as or different from each other, and each represent a -Sp 1 -P 1 group, hydrogen atom, halogen atom, —CN group, —NO 2 group, —NCO group, —NCS group, —OCN group, —SCN group, —SF 5 group, C1-C12 linear or branched alkyl or aralkyl group, phenyl group, or biphenyl group,

at least one of R 1 and R 2 have a -Sp 1 -P 1 group,

P 1 represents an acryloyloxy, methacryloyloxy, vinyl, vinyloxy, acryloylamino, or methacryloylamino group,

Sp 1 represents a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond,

when R 1 and R 2 each represent a phenyl, biphenyl, or a C1-C12 linear or branched alkyl or aralkyl group, a hydrogen atom on R 1 and R 2 may be replaced by a fluorine atom, chlorine atom, or -Sp 1 -P 1 group, and

a —CH 2 — group on R 1 and R 2 may be substituted with a —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group, provided that oxygen, sulfur, and nitrogen atoms are not adjacent to one another.

4 . The liquid crystal display device according to claim 2 ,

wherein P 1 represents a methacryloyloxy group.

5 . The liquid crystal display device according to claim 2 ,

wherein A 3 represents a phenanthrene-2,7-diiyl, phenanthrene-3,6-diyl, phenanthrene-3,8-diyl, or phenanthrene-1,8-diyl group,

P 3 and P 4 both represent a methacryloxy group, and

n represents 0.

6 . The liquid crystal display device according to claim 3 ,

wherein A 3 represents a phenanthrene-2,7-diyl, phenanthrene-3,6-diyl, phenanthrene-3,8-diyl, or phenanthrene-1,8-diyl group,

P 3 and P 4 both represent a methacryloxy group, and

n represents 0.

7 . The liquid crystal display device according to claim 2 ,

wherein A 3 and A 4 both represent a 1,4-phenylene group,

P 3 and P 4 both represent a methacryloxy group, and

n represents 1.

8 . The liquid crystal display device according to claim 3 ,

wherein A 3 and A 4 both represent a 1,4-phenylene group,

P 3 and P 4 both represent a methacryloxy group, and

n represents 1.

9 . The liquid crystal display device according to claim 1 ,

wherein the photoalignment film contains at least one of a compound having at least one photoreactive functional group selected from the group consisting of cinnamate, chalcone, coumarin, azobenzene, tolan, and stilbene groups, and derivatives thereof.

10 . The liquid crystal display device according to claim 1 , further comprising a back light unit.

11 . The liquid crystal display device according to claim 1 ,

wherein one of the first and second substrates includes a color filter and a switching element.

12 . A method of producing a liquid crystal display device, comprising the steps of:

providing a first substrate and a second substrate;

forming a photoalignment film on at least one of the first and second substrates;

forming a liquid crystal layer containing two or more kinds of polymerizable monomers between the first and second substrates after the formation of the photoalignment film; and

forming a polymer layer on the photoalignment film by polymerizing the two or more kinds of polymerizable monomers,

wherein the two or more kinds of polymerizable monomers include at least a polymerizable monomer represented by Formula (I);

wherein A 1 and A 2 are the same as or different from each other, and each represent a benzene ring, biphenyl ring, or C1-C12 linear or branched alkyl or alkenyl group,

one of A 1 and A 2 represents a benzene or biphenyl ring,

at least one of A 1 and A 2 has a -Sp 1 -P 1 group,

a hydrogen atom on A 1 and A 2 each may be replaced by a -Sp 1 -P 1 group, halogen atom, —CN group, —NO 2 group, —NCO group, —NCS group, —OCN group, —SCN group, —SF 5 group, or C1-C12 linear or branched alkyl, alkenyl, or aralkyl group,

two hydrogen atoms bonded to two adjacent carbons in A 1 and A 2 may be replaced by a C1-C12 linear or branched alkylene or alkenylene group to form a ring structure,

a hydrogen atom on the alkyl, alkenyl, alkylene, alkenylene, or aralkyl group in A 1 and A 2 may be substituted with a -Sp 1 -P 1 group,

a —CH 2 — group on the alkyl, alkenyl, alkylene, alkenylene, or aralkyl group in A 1 and A 2 may be substituted with a —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group, provided that oxygen, sulfur, and nitrogen atoms are not adjacent to one another,

P 1 represents a polymerizable group,

Sp 1 represents a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond,

m represents 1 or 2,

a dotted line between A 1 and Y and a dotted line between A 2 and Y represent an optional bond between A 1 and A 2 via Y, and

Y represents a —CH 2 —, —CH 2 CH 2 —, —CH═CH—, —O—, —S—, —NH—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —OCH 2 —, —CH 2 O—, —SCH 2 —, or —CH 2 S— group, or a direct bond, and

a polymerizable monomer represented by Formula (II);

P 3 —S 3 -A 3 -(Z 3 -A 4 ) n -S 4 —P 4   (II)

wherein

P 3 and P 4 may be the same as or different from each other, and each represent an acryloyloxy, methacryloyloxy, acryloylamino, methacryloylamino, vinyl, or vinyloxy group,

A 3 and A 4 may be the same as or different from each other, and each represent a 1,4-phenylene, 4,4′-biphenyl, naphthalene-2,6-diyl, phenanthrene-2,7-diyl, phenanthrene-3,6-diyl, phenanthrene-3,8-diyl, or phenanthrene-1,8-diyl group,

Z 3 may be the same as or different from each other, and each represent a —COO—, —OCO—, —O—, —CO—, —NHCO—, —CONH—, or —S— group or a direct bond between A 3 and A 4 or between A 4 and A 4 ,

n represents 0, 1, 2, or 3,

S 3 and S 4 may be the same as or different from each other, and each represent a —(CH 2 ) m — group (m representing a natural number satisfying 1≦m≦6), a —(CH 2 —CH 2 —O) m — group (m representing a natural number satisfying 1≦m≦6), or a direct bond between P 3 and A 3 , between A 3 and P 4 , or between A 4 and P 4 , and

a hydrogen atom on A 3 and 4 may be replaced by a halogen or methyl group.

13 . The method according to claim 12 ,

wherein the polymerizable monomer represented by Formula (I) is a polymerizable monomer represented by any one of Formulae (I-1) to (I-6);

wherein

R 1 and R 2 may be the same as or different from each other, and each represent a -Sp 1 -P 1 group, hydrogen atom, halogen atom, —CN group, —NO 2 group, —NCO group, —NCS group, —OCN group, —SCN group, —SF 5 group, C1-C12 linear or branched alkyl or aralkyl group, phenyl group, or biphenyl group,

at least one of R 1 and R 2 has a -Sp 1 -P 1 group,

P 1 represents an acryloyloxy, methacryloyloxy, vinyl, vinyloxy, acryloylamino, or methacryloylamino group,

Sp 1 represents a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond,

when R 1 and R 2 each are a phenyl, biphenyl, or C1-C12 linear or branched alkyl or aralkyl group, a hydrogen atom on R 1 and R 2 may be replaced by a fluorine atom, chlorine atom, or -Sp 1 -P 1 group,

a —CH 2 — group on R 1 and R 2 may be substituted with a —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group, provided that oxygen, sulfur, and nitrogen atoms are not adjacent to one another.

14 . The method according to claim 12 ,

wherein the polymerizable monomer represented by Formula (I) is a polymerizable monomer represented by any one of Formulae (I-7) to (I-8) mentioned below;

wherein

R 1 and R 2 may be the same as or different from each other, and each represent a -Sp 1 -P 1 group, hydrogen atom, halogen atom, —CN group, —NO 2 group, —NCO group, —NCS group, —OCN group, —SCN group, —SF 5 group, C1-C12 linear or branched alkyl or aralkyl group, phenyl group, or biphenyl group,

at least one of R 1 and R 2 has a -Sp 1 -P 1 group,

P 1 represents an acryloyloxy, methacryloyloxy, vinyl, vinyloxy, acryloylamino, or methacryloylamino group,

Sp 1 represents a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond,

when R 1 and R 2 each represent a phenyl, biphenyl, or C1-C12 linear or branched alkyl or aralkyl group, a hydrogen atom on R 1 and R 2 may be replaced by a fluorine or chlorine atom, or a -Sp 1 -P 1 group,

a —CH 2 — group on R 1 and R 2 may be substituted with a —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group, provided that oxygen, sulfur, and nitrogen atoms are not adjacent to one another.

15 . The method according to claim 12 ,

wherein the step of forming a polymer layer includes polymerization of the two or more kinds of polymerizable monomers by irradiation of the liquid crystal layer with light of 330 nm or more.

16 . The method according to claim 12 ,

wherein the step of forming a polymer layer includes polymerization of the two or more kinds of polymerizable monomers by irradiation of the liquid crystal layer with light of 360 nm or more.

17 . The method according to claim 12 ,

wherein the step of forming a polymer layer includes polymerization of the two or more kinds of polymerizable monomers with application of a voltage of the threshold value or greater to the liquid crystal layer.

18 . The method according to claim 12 ,

wherein the step of forming a polymer layer includes polymerization of the two or more kinds of polymerizable monomers with application of a voltage lower than the threshold value to the liquid crystal layer or without application of a voltage to the liquid crystal layer.

19 . The method according to claim 12 , further comprising the step of performing alignment treatment on the photoalignment film by irradiating the photoalignment film with light before the step of forming a liquid crystal layer.