Fluorene derivatives and their polymers

Details Fluorene derivatives and their polymers Fluorene derivatives and their polymers

2002-12-12

2004-11-30

Wu, Shean C. (Department: 1756)

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

C252S299670, C252S299660, C428S001100, C585S021000, C570S125000, C570S187000

Reexamination Certificate

active

06824709

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a fluorene derivative having both of a polymerizing property and liquid crystallinity, a composition thereof and a polymer thereof. They can be used for a retardation film, a polarizer, a liquid crystal aligning film, a anti-reflection film and a viewing angle compensation film which are structural elements for a liquid crystal display device.
BACKGROUND OF THE INVENTION
Document 1: Japanese Patent Application Laid-Open No. 3111/1996
Document 2: Japanese Patent Application Laid-Open No. 17910/1995
Document 3: Japanese Patent Application Laid-Open No. 316032/1997
It is described in the document 1 that when a liquid crystal compound showing a polymerizing property is photopolymerized in the state that it is aligned, a state uniformly aligned is fixed and a polymer showing an optical anisotropy is obtained. Examples in which acrylate compounds were used as a liquid crystal compound showing a polymerizing property are described in the document 2 and the document 3. A high reactivity of the acrylate compounds and a transparency of the polymers are considered in these documents. Preferred examples of a polymerizable liquid crystalline acrylate compound are compounds (a) to (c) which are constituted by a cyclohexane ring and a benzene ring:
However, an optically anisotropic film prepared using a polymer of a publicly known acrylate compound did not have satisfactory characteristics in heat resistance and mechanical properties such as surface hardness.
SUMMARY OF THE INVENTION
A subject of the present invention is to solve the problems in prior art, and a novel liquid crystalline compound is provided for this purpose. That is, a first object of the present invention is to provide a polymerizable liquid crystalline compound which satisfies a large part of properties such as a broad temperature range of a liquid crystal phase, a high clearing point, a large optical anisotropy, a low viscosity, a high compatibility with the other liquid crystalline compounds, an excellent aligning property, a high photopolymerizing property and a high solubility in an organic solvent. A second object of the present invention is to provide a polymer which is prepared from this compound and which satisfies a large part of properties such as a heat resistance, a surface hardness, a large optical anisotropy, a low water permeability (a high hygroscopic dimensional stability), a high gas barrier property, an optimum heat contraction (an optimum thermal expansion coefficient), a small haze value, a high transparency, a suitable refractive index, a high solvent resistance, a high weatherability, a high glass transition point, a large light transmittance (a low light loss), a high wettability and an optimum thermoelasticity.
The present invention is constituted by the following items.
[1] A fluorene derivative represented by Formula (1):
wherein A
1
, A
2
and A
3
are independently a group represented by Formula (2), 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, pyridine-2,5-diyl, pyridazine-3,6-diyl, pyrimidine-2,5-diyl, dioxane-2,5-diyl, 1,4-cyclohexylene in which optional hydrogens are replaced by fluorines, or 1,4-phenylene in which optional hydrogens are replaced by fluorine and/or chlorine, and at least one of A
1
, A
2
and A
3
is the group represented by Formula (2); m, n and p are independently 0 or 1, and the total thereof is 1 to 3; R
1
is —CN, —CF
3
, —CF
2
H, —CFH
2
, —OCF
3
, —OCF
2
H, —N═C═O, —N═C═S, —F, —Cl or alkyl having 1 to 20 carbon atoms, and in this alkyl, one hydrogen may be replaced by (meth)acryloyloxy or vinyloxy and optional —CH
2
— may be replaced by —O—, —S—, —CF
2
—, —CH═CH—, —COO—, —OCO— or —CO—; R
2
is hydrogen or methyl; Z
1
, Z
2
and Z
3
are independently a single bond, —O—, —COO—, —OCO—, —CF
2
O—, —OCF
2
—, —CH
2
O—, —OCH
2
—, —CH
2
CH
2
—, —(CH
2
)
4
—, —CH═CH—, —CF═CF— or —C≡C—; q is an integer of 0 to 10; and r is 0 or 1:
wherein two X
1
's are independently hydrogen, fluorine or alkyl having 1 to 8 carbon atoms.
[2] The fluorene derivative as described in the item [1], wherein both of two X
1
's in Formula (2) are hydrogens.
[3] The fluorene derivative as described in the item [1], wherein both of two X
1
's in Formula (2) are fluorines.
[4] The fluorene derivative as described in the item [1], wherein R
2
in Formula (1) is hydrogen.
[5] The fluorene derivative as described in the item [1], wherein R
2
in Formula (1) is methyl.
[6] The fluorene derivative as described in the item [1], wherein in Formula (1), R
1
is alkyl or alkoxy, and R
2
is hydrogen.
[7] The fluorene derivative as described in the item [1], wherein in Formula (1), R
1
is alkyl or alkoxy, and R
2
is methyl.
[8] The fluorene derivative as described in the item [1], wherein in Formula (1), R
1
is alkyl or alkoxy; R
2
is hydrogen; and both of two X
1
's in Formula (2) are hydrogens.
[9] The fluorene derivative as described in the item [1], wherein in Formula (1), R
1
is alkyl or alkoxy; R
2
is methyl; and both of two X
1
's in Formula (2) are fluorines.
[10] The fluorene derivative as described in the item [1], wherein in Formula (2), at least one X
1
is methyl.
[11] The fluorene derivative as described in the item [1], wherein in A
1
, A
2
and A
3
in Formula (1), one of them is the group represented by Formula (2), and the other groups are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexylene in which optional hydrogens are replaced by fluorines, or 1,4-phenylene in which optional hydrogens are replaced by fluorine and/or chlorine.
[12] The fluorene derivative as described in the item [1], wherein R
1
is a group having (meth)acryloyloxy or vinyloxy.
[13] The fluorene derivative as described in the item [1], wherein in A
1
, A
2
and A
3
in Formula (1), one of them is the group represented by Formula (2), and the other groups are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexylene in which optional hydrogens are replaced by fluorines, or 1,4-phenylene in which optional hydrogens are replaced by fluorine and/or chlorine; and R
1
is a group having (meth)acryloyloxy or vinyloxy.
[14] The fluorene derivative as described in the item [1], wherein in Formula (1), A
2
is the group represented by Formula (2); A
1
and A
3
are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-cyclohexylene in which optional hydrogens are replaced by fluorines, or 1,4-phenylene in which optional hydrogens are replaced by fluorine and/or chlorine; R
1
is a group represented by Formula (LT); Z
3
is —O—; and q is an integer of 2 to 10:
wherein R
3
is hydrogen or methyl; r1 is 0 or 1; and q1 is an integer of 2 to 10.
[15] The fluorene derivative as described in the item [1], wherein in Formula (1), A
2
is the group represented by Formula (2); A
1
and A
3
are independently 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which optional hydrogens are replaced by fluorines; R
1
is a group represented by Formula (LT-1); R
2
is hydrogen; Z
1
and Z
2
are independently a single bond, —CH
2
CH
2
—, —COO— or —OCO—; Z
3
is —O—; r is 1; and q is an integer of 2 to 10:
wherein q1 is an integer of 2 to 10.
[16] The fluorene derivative as described in the item [1], wherein in Formula (1), A
2
is the group represented by Formula (2); A
1
and A
3
are independently 1,4-cyclohexylene, 1,4-phenylene or 1,4-phenylene in which optional hydrogens are replaced by fluorines; R
1
is a group represented by Formula (LT-2); R
2
is hydrogen; Z
1
and Z
2
are independently a single bond, —CH
2
CH
2
—, —COO— or —OCO—; Z
3
is —O—; r is 0; and q is an integer of 2 to 10:
wherein q1 is an integer of 2 to 10.
[17] The fluorene derivative as described

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