Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-12-20
2002-04-30
Wu, Shean C. (Department: 1756)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S391000, C564S431000, C570S128000, C570S129000, C570S131000
Reexamination Certificate
active
06380432
ABSTRACT:
BACKGROUND OF INVENTION
The present invention relates to materials for aligning liquid crystals, and liquid crystal optical elements.
Current liquid crystal display (LCD) elements include a product that utilize a twisted nematic mode, i.e., having a structure wherein the aligning direction of nematic liquid crystal molecules is twisted by 90° between a pair of upper and lower electrode substrates, a product utilizing a supertwisted nematic mode, utilizing a birefringent effect, i.e. having a structure wherein the aligning direction of nematic liquid crystal molecules is twisted by 180° to 300°, an in-plane-switching mode wherein both electrodes controlling the liquid crystal alignment are present on one substrate and the direction of the liquid crystal orientation in the plane of the substrate changes upon application of an electric field, and a product utilizing a ferroelectric liquid crystal substance or an antiferroelectric liquid crystal substance. Common to each of these products is a liquid crystal layer disposed between a pair of substrates coated with a polymeric alignment layer. The polymeric alignment layer controls the direction of alignment of the liquid crystal medium in the absence of an electric field. Usually the direction of alignment of the liquid crystal medium is established in a mechanical buffing process wherein the polymer layer is buffed with a cloth or other fiberous material. The liquid crystal medium contacting the buffed surface typically aligns parallel to the mechanical buffing direction. Alternatively, an alignment layer comprising anisotropically absorbing molecules can be exposed to polarized light to align a liquid crystal medium as disclosed in U.S. Pat. Nos. 5,032,009 and 4,974,941 “Process of Aligning and Realigning Liquid Crystal Media”.
The process for aligning liquid crystal media with polarized light can be a noncontact method of alignment that has the potential to reduce dust and static charge buildup on alignment layers. Other advantages of the optical alignment process include high resolution control of alignment direction and high quality of alignment.
Requirements of optical alignment layers for liquid crystal displays include low energy threshold for alignment, transparency to visible light (no color), good dielectric properties and voltage holding ratios, long-term thermal and optical stability, and in many applications a controlled uniform pre-tilt angle.
Most liquid crystal devices, including displays, have a finite pre-tilt angle, controlled, for instance, by the mechanical buffing of selected polymeric alignment layers. The liquid crystal molecules in contact with such a layer aligns parallel to the buffing direction, but is not exactly parallel to the substrate. The liquid crystal molecules are slightly tilted from the substrate, for instance by about 2-15 degrees. For optimum performance in most display applications a finite and uniform pre-tilt angle of the liquid crystal is desirable.
Polymers used in forming optical alignment layers also must have a reasonably broad processing window. Polymers used as alignment layers in commercial liquid crystal displays are generally polyimide-based systems because of their good thermal and electrical properties. Thus, within the polyimide family, polymers also must have functionality that is stable to thermal and/or chemical imidization. In addition, polymers must have good wetting characteristics and printability onto substrates to give uniform layers.
Several approaches have been explored to meet the performance requirements of optical alignment layers for production of liquid crystal displays. In particular, U.S. Pat. No. 5,731,405 describes polyimide optical alignment layers having C
4
to C
20
fluorinated or partially fluorinated alkyl chains as side-groups. These materials probably alter the surface properties of the optical alignment layers. International application WO 99/15576 describes photoreactive polyimide polymers that have 3-arylacrylic ester (cinnamates) side-groups. When irradiated with polarized light, these materials undergo photo-crosslinking to produce optical alignment layers with a defined angle of tilt. In this case, establishing pre-tilt in the optical alignment layer requires the use of a specific chromophore, for instance, a cinnamate ester.
In further developing pre-tilt inducing materials and processes for optical alignment layers a new class of reactive materials have been discovered that allow control of pre-tilt in optical alignment layers with chromophores other than cinnamate esters and the like.
SUMMARY OF INVENTION
The present invention provides reactive side-chain polymers within the class of polyimides, polyamic acids and esters thereof, characterized in that they comprise monovalent side chains of the general formula I:
—L
1
—D—L
2
—C
f
wherein the monovalent link is to a polymer main chain and wherein:
—L
1
and L
2
each, independently, is a covalent bond or a linking group selected from the group of —O—, —S—, —NR
1
—, —O—CO—, —CO—O—, —NR
1
—CO—, —CO—NR
1
—, —NR
1
—CO—O—, —O—CO—NR
1
—, —NR
1
—CO—NR
1
—, and straight-chain or branched-chain alkylenes represented by —(CH
2
)
n
—, —L
3
—(CH
2
)
n
—, —(CH
2
)
n
—L
3
, —L
3
—(CH
2
)
n
—L
4
—, each optional mono- or poly-substituted by fluorine or chlorine and optionally chain interrupted by —O— or —NR
1
, wherein L
3
and L
4
are selected from the group of —O—, —S—, —NR
1
—, —O—CO—, —CO—O—, —NR
1
—CO—, —CO—NR
1
—, —NR
1
—CO—O—, —O—CO—NR
1
—, —NR
1
—CO—NR
1
—, R
1
is a hydrogen or lower alkyl group and n is 1 to 20;
D is a divalent group containing 1 to 4 carbon-carbon double bonds, selected from the group of C
3
-C
24
aliphatic, C
3
-C
24
alicyclic, C
8
-C
24
arylalkyl groups, all optionally substituted with 1 to 4 heteroatoms selected from the group of oxygen, nitrogen or sulfur and optionally mono- or poly-substituted by fluorine, chlorine or cyano, wherein the carbon-carbon double bond(s) are isolated from any other Π-system within the side-chain;
C
f
represents a monovalent C
4
to C
20
fluorocarbon radical.
The invention further embodies optical alignment layers prepared from the side-chain polymers and liquid crystal display elements incorporating the optical alignment layers.
REFERENCES:
patent: 4974941 (1990-12-01), Gibbons et al.
patent: 5032009 (1991-07-01), Gibbons et al.
patent: 5186985 (1993-02-01), Estes et al.
patent: 5270438 (1993-12-01), Yusa et al.
patent: 5731405 (1998-03-01), Gibbons et al.
patent: 5925423 (1999-07-01), Han et al.
patent: 6194039 (2001-02-01), Gibbons et al.
patent: 6242061 (2001-06-01), Gibbons et al.
patent: 9915576 (1999-04-01), None
Gibbons Wayne M.
Rose Patricia A.
Shannon Paul J.
Zheng Hanxing
Elsicon Inc.
Shannon Paul J.
Wu Shean C.
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