Liquid crystal display and optical compensatory sheet and process for preparation of the same

• US 5,635,105 A
• Filed: 05/12/1995
• Issued: 06/03/1997
• Est. Priority Date: 05/13/1994
• Status: Expired due to Term

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Nishikawa, Hideyuki, Kawata, Ken, Kamada, Koh, Okazaki, Masaki, Negoro, Masayuki, Maeta, Hideki
• Primary Examiner(s): KELLY, CYNTHIA HARRIS
• Application Number:
  US08/440,250
• Time in Patent Office: 753 Days
• Field of Search: 252/299.01, 252/299.62, 526/328, 526/319, 359/73
• US Class Current: 252/299.01
• CPC Class Codes: G02F 1/133632 with refractive index ellipsoid inclined relative to the LC-layer surface
• CPC Class Codes: G02F 1/1396 the liquid crystal being selectively controlled between a twisted state and a non-twisted state, e.g. TN-LC cell G02F1/141 takes precedence
• CPC Class Codes: G02F 1/1397 the twist being substantially higher than 90°, e.g. STN-, SBE-, OMI-LC cells

Abstract

Disclosed are a liquid crystal display provided with an optical compensatory sheet comprising an optically anisotropic layer which has negative birefringence and comprises a polymer having a discotic structure in its molecule, and an optical compensatory sheet which comprises a transparent support, an orientation layer provided thereon and the optically anisotropic layer provided on the orientation layer. Further, a process for preparation of the optical compensatory sheet and a liquid crystal composition which is useful as material for preparing the optical compensatory sheet are also disclosed.

Claims

1. An optical compensatory sheet which comprises a transparent support, an orientation layer provided thereon and an optically anisotropic layer provided on the orientation layer, wherein the optically anisotropic layer has negative birefringence and comprises a polymer having a discotic structure in its molecule.

2. The optical compensatory sheet as defined in claim 1, wherein the polymer is a homopolymer of a polymerizable discotic compound having liquid crystalline property.

3. The optical compensatory sheet as defined in claim 1, wherein the polymer is a copolymer of a polymerizable discotic compound having liquid crystalline property and at least one polymerizable compound selected from the group consisting of compounds having the formula (9):

space="preserve" listing-type="equation">(E.sub.n6 D6(L6-P6).sub.k6 (

     9)

wherein D6 represents a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, a trithiatruxene ring, a trioxatruxene ring, a hexaethyne substituted benzene ring, a colonene ring, a dibenzopyrene ring, an inositol ring, a phthalocyanine ring or a macrocycle ring of phenylacetylene, E represents an alkyl group, an alkoxy group, an oligo-oxyethylene group in which plural oxyethylenes are combined, an acyl group, an acyloxy group, a benzoyloxy group or a benzoyl group, P6 represents an isocyanato group, a thiocyanato group, an amino group, an alkylamino group, an arylamino group, a mercapto group, a formyl group, an acyl group, a hydroxy group, a carboxyl group, a sulfo group, a phosphoryl group, a halocarbonyl group, a halosulfonyl group, a halophosphoryl group, an acryloyl group, a vinyloxy group, an epoxy group, a methacryloyl group, an acetylene group, an allenyl group or a propargyl group, L6 represents one divalent connective group selected from the group consisting of an alkylene group, an alkyleneoxy group, a phenylene group, and an alkylene group having carbonyl at one end, n6 represents an integer of 0 to 7 and k6 represents an integer of 1 to 8, under the condition of n6+k6≦

8.

4. The optical compensatory sheet as defined in claim 2 or 3, wherein the polymerizable discotic compound having liquid crystalline property is at least one compound having liquid crystalline property selected from the group consisting of compounds having the formula (8):

space="preserve" listing-type="equation">(B).sub.n5 D5(L5-P5).sub.k5 (

     8)

wherein D5 represents a triphenylene ring, a truxene ring, a trithiatruxene ring, a trioxatruxene ring, a hexaethyne substituted benzene ring, a colonene ring, a dibenzopyrene ring, an inositol ring, a phthalocyanine ring or a macrocycle ring of phenylacetylene, B represents an alkyl group, an alkoxy group, an oligo-oxyethylene group in which plural oxyethylenes are combined, an acyl group, an acyloxy group, a benzoyloxy group or a benzoyl group, P6 represents an isocyanato group, P5 represents an isocyanato group, a thiocyanato group, an amino group, an alkylamino group, an arylamino group, a mercapto group, a formyl group, an acyl group, a hydroxy group, a carboxyl group, a sulfo group, a phosphoryl group, a halocarbonyl group, a halosulfonyl group, a halophosphoryl group, an acryloyl group, a vinyloxy group, an epoxy group, a methacryloyl group, an acetylene group, an allenyl group or a propargyl group, L5 represents a divalent connective group selected from the group consisting of an alkylene group, an alkyleneoxy group, a phenylene group, and an alkylene group having carbonyl at one end, n5 represents an integer of 0 to 7 and k5 represents an integer of 1 to 8, under the condition of n5+k5≦

8.

5. The optical compensatory sheet as defined in claim 2 or 3, wherein the polymerizable discotic compound having liquid crystalline property has the formula (1), (2) or (3):

##STR63## wherein R¹⁰ is the following group;

##STR64## in which each of R¹¹ and R¹² represents independently a hydrogen atom or a methyl group, and R¹³ represents an alkoxy group of 1 to 12 carbon atoms or the following group;

##STR65## in which m1 represents 0 or 1, R¹⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j1 represents an integer of 0 to 4, R¹⁸ represents an alkylene group of 1 to 12 carbon atoms, g1 represents an integer of 0 to 4, h1 represents 0 or 1, and each of R¹⁴, R¹⁵ and R¹⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

##STR66## wherein R²⁰ is the following group;

##STR67## in which each of R²¹ and R²² represents independently a hydrogen atom or a methyl group, and R²³ represents an alkoxy group of 1 to 12 carbon atoms or the following group;

##STR68## in which m2 represents 0 or 1, R²⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j2 represents an integer of 0 to 4, R²⁸ represents an alkylene group of 1 to 12 carbon atoms, g2 represents an integer of 0 to 4, and each of R²⁴, R²⁵ and R²⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

##STR69## wherein R³⁰ is the following group;

##STR70## in which each of R³¹ and R³² represents independently a hydrogen atom or a methyl group, and R³³ represents an alkoxy group of 1 to 12 carbon atoms or the following group;

##STR71## in which m3 represents 0 or 1, R³⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j3 represents an integer of 0 to 4, R³⁸ represents an alkylene group of 1 to 12 carbon atoms, g3 represents an integer of 0 to 4, and each of R³⁴, R³⁵ and R³⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms.

6. The optical compensatory sheet as defined in claim 3, wherein the polymerizable compound of the formula (9) has the formula (4), (5) or (6):

space="preserve" listing-type="equation">(X).sub.n1 D1[O--(L1).sub.s1 --P1].sub.k1 (

     4)

wherein D1 represents a benzene ring or naphthalene ring, X represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k1 represents 1, 2 or 3 under the condition of n1+k1=6 when D1 represents a benzene ring and k1 represents 1, 2 or 3 under the condition of n1+k1=6 when D1 represents a naphthalene ring, s1 represents 0 or 1, L1 is the following group;

##STR72## in which each of R⁴¹ and R⁴² represents independently a hydrogen atom or a methyl group,

and P1 represents the following group;

##STR73## in which R⁴⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j4 represents an integer of 0 to 4, R⁴⁸ represents an alkylene group of 1 to 12 carbon atoms, g4 represents an integer of 0 to 4, and each of R⁴⁴, R⁴⁵ and R⁴⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

space="preserve" listing-type="equation">(Y).sub.n2 D2[O--(L2).sub.s2 --P2].sub.k2 (

     5)

wherein D2 represents a benzene ring or naphthalene ring, Y represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k2 represents 1, 2 or 3 under the condition of n2+k2=6 when D2 represents a benzene ring and k2 represents 1, 2 or 3 under the condition of n2+k2=6 when D2 represents a naphthalene ring, s2 represents 0 or 1, L2 is the following group;

##STR74## in which each of R⁵¹ and R⁵² represents independently a hydrogen atom or methyl group,

and P2 represents the following group;

##STR75## in which R⁵⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j5 represents an integer of 0 to 4, R⁵⁸ represents an alkylene group of 1 to 12 carbon atoms, g5 represents an integer of 0 to 4, h5 represents 0 or 1, and each of R⁵⁴, R⁵⁵ and R⁵⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

space="preserve" listing-type="equation">(Z).sub.n3 D3[O--(L3).sub.s3 --P3].sub.k3 (

     6)

wherein D3 represents a benzene ring or naphthalene ring, Z represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k3 represents 1, 2 or 3 under the condition of n3+k3=6 when D3 represents a benzene ring and k2 represents 1, 2 or 3 under the condition of n3+k3=6 when D3 represents a naphthalene ring, s3 represents 0 or 1, L3 is the following group;

##STR76## in which each of R⁶¹ and R⁶² represents independently a hydrogen atom or methyl group,

and P3 represents the following group;

##STR77## in which R⁶⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j6 represents an integer of 0 to 4, R⁶⁸ represents an alkylene group of 1 to 12 carbon atoms, g6 represents an integer of 0 to 4, and each of R⁶⁴, R⁶⁵ and R⁶⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms.

7. The optical compensatory sheet as defined in claim 1, wherein the discotic structure is triphenylene ring, a, truxene ring, a trithiatruxene ring, a trioxatruxene ring, a hexaethyne substituted benzene ring, a colonene ring, a dibenzopyrene ring, an inositol ring, a phthalocyanine ring or a macrocycle ring of phenylacetylene.

8. A liquid crystal display comprising a liquid crystal cell which comprises a pair of substrates each of which is provided with a transparent electrode and twist-oriented or super twist-oriented nematic liquid crystal sealed therebetween, a polarizing sheet arranged on each side of the cell, and an optical compensatory sheet of claim 1 provided between at least one side of the liquid crystal cell and the polarizing sheet.

9. A process for preparation of an optical compensatory sheet having negative birefringence, which comprises the steps of:

coating a solution which contains a polymerizable discotic compound having liquid crystalline property, on an orientation layer provided on a transparent support to form a coated layer,

heating the coated layer to form a discotic nematic phase,

radiating light on the coated layer to cure, and

cooling the cured layer.

10. A liquid crystalline composition which comprising a polymerizable discotic compound having liquid crystalline property and a polymerizable compound having the formula (4), (5) or (6):

space="preserve" listing-type="equation">(X).sub.n1 D1[O--(L1).sub.s1 --P1].sub.k1 (

     4)

wherein D1 represents a benzene ring or naphthalene ring, X represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k1 represents 1, 2 or 3 under the condition of n1+k1=6 when D1 represents a benzene ring and k1 represents 1, 2 or 3 under the condition of n1+k1=8 when D1 represents a naphthalene ring, s1 represents 0 or 1, L1 is the following group;

##STR78## in which each of R⁵¹ and R⁵² represents independently a hydrogen atom or a methyl group,

and P1 represents the following group;

##STR79## in which R⁴⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j4 represents an integer of 0 to 4, R⁴⁸ represents an alkylene group of 1 to 12 carbon atoms, g4 represents an integer of 0 to 4, and each of R⁴⁴, R⁴⁵ and R⁴⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

space="preserve" listing-type="equation">(Y).sub.n2 D2[O--(L2).sub.s2 --P2].sub.k2 (

     5)

wherein D2 represents a benzene ring or naphthalene ring, Y represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k2 represents 1, 2 or 3 under the condition of n2+k2=6 when D2 represents a benzene ring and k2 represents 1, 2 or 3 under the condition of n2+k2=8 when D2 represents a naphthalene ring, s2 represents 0 or 1, L2 is the following group;

##STR80## in which each of R⁵¹ and R⁵² represents independently a hydrogen atom or methyl group,

and P2 represents the following group;

##STR81## in which R⁵⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j5 represents an integer of 0 to 4, R⁵⁸ represents an alkylene group of 1 to 12 carbon atoms, g5 represents an integer of 0 to 4, h5 represents 0 or 1, and each of R⁵⁴, R⁵⁵ and R⁵⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

space="preserve" listing-type="equation">(Z).sub.n3 D3[O--(L3).sub.s3 --P3].sub.k3 (

     6)

wherein D3 represents a benzene ring or naphthalene ring, Z represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k3 represents 1, 2 or 3 under the condition of n3+k3=6 when D3 represents a benzene ring and k2 represents 1, 2 or 3 under the condition of n3+k3=8 when D3 represents a naphthalene ring, s3 represents 0 or 1, L3 is the following group;

##STR82## in which each of R⁶¹ and R⁶² represents independently a hydrogen atom or methyl group,

and P3 represents the following group;

##STR83## in which R⁶⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j6 represents an integer of 0 to 4, R⁶⁸ represents an alkylene group of 1 to 12 carbon atoms, g6 represents an integer of 0 to 4, and each of R⁶⁴, R⁶⁵ and R⁶⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms.

11. The liquid crystalline composition as defined in claim 10, wherein the polymerizable discotic compound has the formula (1), (2) or (3):

##STR84## wherein R¹⁰ is the following group;

##STR85## in which each of R¹¹ and R¹² represents independently a hydrogen atom or a methyl group, and R¹³ represents an alkoxy group of 1 to 12 carbon atoms or the following group;

##STR86## in which m1 represents 0 or 1, R¹⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j1 represents an integer of 0 to 4, R¹⁸ represents an alkylene group of 1 to 12 carbon atoms, g1 represents an integer of 0 to 4, h1 represents 0 or 1, and each of R¹⁴, R¹⁵ and R¹⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

##STR87## wherein R²⁰ is the following group;

##STR88## in which each of R²¹ and R²² represents independently a hydrogen atom or a methyl group, and R²³ represents an alkoxy group of 1 to 12 carbon atoms or the following group;

##STR89## in which m2 represents 0 or 1, R²⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j2 represents an integer of 0 to 4, R²⁸ represents an alkylene group of 1 to 12 carbon atoms, g2 represents an integer of 0 to 4, and each of R²⁴, R²⁵ and R²⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms;

##STR90## wherein R³⁰ is the following group;

##STR91## in which each of R³¹ and R³² represents independently a hydrogen atom or a methyl group, and R³³ represents an alkoxy group of 1 to 12 carbon atoms or the following group;

##STR92## in which m3 represents 0 or 1, R³⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j3 represents an integer of 0 to 4, R³⁸ represents an alkylene group of 1 to 12 carbon atoms, g3 represents an integer of 0 to 4, and each of R³⁴, R³⁵ and R³⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms.

12. A compound having the formula (7):

space="preserve" listing-type="equation">(Q).sub.n4 D4(O--L4--P4).sub.k4 (

     7)

wherein D4 represents a benzene ring or naphthalene ring, Q represents a hydrogen atom, an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, k4 represents 1, 2 or 3 under the condition of n4+k4=6 when D4 represents a benzene ring and k4 represents 1, 2 or 3 under the condition of n4+k4=8 when D4 represents a naphthalene ring, L4 is the following group;

##STR93## in which each of R⁷¹ and R⁷² represents independently a hydrogen atom or a methyl group,

and P4 represents the following group;

##STR94## which R⁷⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j7 represents an integer of 0 to 4, R⁷⁸ represents an alkylene group of 1 to 12 carbon atoms, g7 represents an integer of 0 to 4, and each of R⁷⁴, R⁷⁵ and R⁷⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms.

13. A compound having the formula (10):

##STR95## wherein P10 represents the following group;

##STR96## which R⁸⁷ represents an alkyleneoxy group of 1 to 6 carbon atoms, j8 represents an integer of 0 to 4, R⁸⁸ represents an alkylene group of 1 to 12 carbon atoms, g8 represents an integer of 0 to 4, and each of R⁸⁴, R⁸⁵ and R⁸⁶ represents independently a hydrogen atom or an alkyl group of 1 to 12 carbon atoms.