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US5200238A
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Liquid crystal display devices and method of manufacture
Assignee: Henkel Loctite Ireland Ltd
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Filing: 1991-09-25
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Granted: 1993-04-06
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Expires: 2011-09-25
Abstract
Abstract A method of forming liquid crystal alignment layers of high tilt angle, said method comprising preparing a polymeric film of a monomer of the formula IV: ##STR1## wherein X and Y are strong electron withdrawing groups, optionally substituted with or containing Si or Ti, and A is --H or --CH═CH 2 or, provided that X and Y are both --CN, A may be --R 2 or --CH═CHR 2 wherein R 2 is hydrocarbyl, aryl or alkaryl; exposing said polymeric film to ultraviolet radiation for sufficient period of time to photochemically modify the polymer and, thereafter, subjecting the modified polymer to a heat treatment in the range of 100°-400° C. for at least 5 seconds.
Inventors
- 👤 Ciaran B. McArdle
- 👤 John G. Woods
- 👤 Anthony F. Jacobine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 23:48
CPC Classifications
G; G02; G02F; G02F1/00; G02F1/01; G02F1/13; G02F1/133; G02F1/1333; G02F1/1337; G02F1/133711; C; C09; C09K; C09K2323/00; C09K2323/02; C09K2323/023; G02F1/133746; G02F1/137; G02F1/139; G02F1/1396; G02F1/1397; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
129 words
A method of forming a liquid crystal alignment layer having a tilt angle of at least about 5 degrees, said method comprising (i) coating a liquid crystal electrode with a polymer of a monomer of the formula IV: ##STR11## wherein A is --H or --CH═CH 2 or, provided that X and Y are both --CN, A may be --R 2 or --CH═CHR wherein R 2 is hydrocarbyl, aryl or alkaryl, and X and Y are strong electron withdrawing groups; (ii) exposing the polymer to UV irradiation of sufficient intensity and for a time period of from about 0.1 seconds to about 5 minutes to photochemically modify the polymer; and (iii) heating the modified polymer for at least about 5 seconds at from about 100° C. to about 400° C.
Claim 2
Independent Claim
129 words
A method of forming a liquid crystal alignment layer having a tilt angle of at least about 5 degrees, said method comprising (i) coating a liquid crystal electrode with a polymer of a monomer of the formula IV: ##STR11## wherein A is --H or --CH═CH 2 or, provided that X and Y are both --CN, A may be --R 2 or --CH═CHR wherein R 2 is hydrocarbyl, aryl or alkaryl, and X and Y are strong electron withdrawing groups; (ii) exposing the polymer to UV irradiation of sufficient intensity and for a time period of from about 0.1 seconds to about 5 minutes to photochemically modify the polymer; and (iii) heating the modified polymer for at least about 5 seconds at from about 100° C. to about 400° C.
Claim 3
Dependent Claim
23 words
The method of claim 1 wherein the polymer coating is applied to the electrode as a polymer in solution by conventional spin-coating techniques.
Claim 4
Dependent Claim
20 words
The method of claim 1 wherein the polymer coating is applied to the electrode through vapor deposition of the monomer.
Claim 5
Dependent Claim
93 words
The method of claim 1 wherein X and Y are independently selected from --CN, --COR 3 , --COOR 4 , --SO 2 R 4 and --SO 3 R 4 wherein R 3 is H, a hydrocarbyl group, an Si or Ti containing hydrocarbyl group or a hydrocarbyl group substituted with an Si or Ti containing group and R 4 is a hydrocarbyl group, a substituted hydrocarbyl group, an Si or Ti containing hydrocarbyl or substituted hydrocarbyl group or a hydrocarbyl group or substituted hydrocarbyl group substituted with an Si or Ti containing group.
Claim 6
Dependent Claim
16 words
The method of claim 4 wherein R 3 is a C 1 -C 12 hydrocarbyl group.
Claim 7
Dependent Claim
81 words
The method of claim 4 wherein R 4 is an unsubstituted, halo substituted or alkoxy substituted straight chain or branched chain C 1 -C 12 alkyl group, a straight chain or branched chain C 2 -C 12 alkenyl group, a straight chain or branched chain C 2 -C 12 alkynyl group, a cycloalkyl group, an aralkyl group or an aryl group or any of the foregoing containing an Si or Ti atom or substituted with an Si or Ti containing group.
Claim 8
Dependent Claim
90 words
The method of claim 1 wherein X is --CN and Y is COOR 4 and R 4 is an unsubstituted, halo substituted or alkoxy substituted straight chain or branched chain C 1 -C 12 alkyl group, a straight chain or branched chain C 2 -C 12 alkenyl group, a straight chain or branched chain C 2 -C 12 alkynyl group, a cycloalkyl group, an aralkyl group or an aryl group or any of the foregoing containing an Si or Ti atom or substituted with an Si or Ti containing group.
Claim 9
Dependent Claim
45 words
The method of claim 1 wherein A is --H, X is --CN and Y is --COOR 5 wherein R 5 is a C 1 -C 5 alkyl or C 2 -C 5 alkenyl group, or a group having at least one chiral center carbon atom.
Claim 10
Dependent Claim
172 words
The method of claim 4 wherein R 3 or R 4 comprises: ##STR12## wherein R 2a , R 3a and R 4a , which may be the same or different, are selected from H (provided that not more than one of R 2a , R 3a and R 4a is H), C 1 -C 10 alkyl, aryl, C 1 -C 10 alkoxy and siloxy groups of the formula: ##STR13## wherein R 5a , R 6a and R 7a , which may be the same or different, are selected from H, CH 3 or phenyl, provided that not more than one of R 5a , R 6a and R 7a is H; and wherein R 2a may also be a group selected from siloxane oligomers or polymers of the structure: ##STR14## wherein R 5a , R 6a and R 7a are defined as above and m is 2 or 3, preferably 2; provided that the monomer with such substituent(s) has significant vapor pressure or can be heated to generate vapor pressure without decomposition.
Claim 11
Dependent Claim
181 words
The method of claim 4 wherein R 3 or R 4 is substituted with at least one group of the formula: ##STR15## wherein R 2a , R 3a and R 4a , which may be the same or different, are selected from H (provided that not more than one of R 2a , R 3a and R 4a is H), C 1 -C 10 alkyl, aryl, C 1 -C 10 alkoxy and siloxy groups of the formula: ##STR16## wherein R 5a , R 6a and R 7a , which may be the same or different, are selected from H, CH 3 or phenyl, provided that not more than one of R 5a , R 6a and R 7a is H; and wherein R 2a may also be a group selected from siloxane oligomers or polymers of the structure: ##STR17## wherein R 5a , R 6a and R 7a are defined as above and m is 2 or 3, preferably 2; provided that the monomer with such substituent(s) has significant vapor pressure or can be heated to generate vapor pressure without decomposition.
Claim 12
Dependent Claim
176 words
The method of claim 1 wherein X is CN and Y is: ##STR18## wherein n is 1-5 and R 2a , R 3a and R 4a , which may be the same or different, are selected from H (provided that not more than one of R 2a , R 3a and R 4a is H), C 1 -C 10 alkyl, aryl, C 1 -C 10 alkoxy and siloxy groups of the formula: ##STR19## wherein R 5a , R 6a and R 7a , which may be the same or different, are selected from H, CH 3 or phenyl, provided that not more than one of R 5a , R 6a and R 7a is H; and wherein R 2a may also be a group selected from siloxane oligomers or polymers of the structure: ##STR20## wherein R 5a , R 6a and R 7a are defined as above and m is 2 or 3, preferably 2; provided that the monomer with such substituent(s) has significant vapor pressure or can be heated to generate vapor pressure without decomposition.
Claim 13
Dependent Claim
26 words
The method of claim 11 wherein R 2a , R 3a and R 4a are C 1 -C 10 alkyl and n is at least 3.
Claim 14
Dependent Claim
18 words
The method of claim 1 wherein the intensity of the UV lamp is about 100 mW/cm 2 .
Claim 15
Dependent Claim
22 words
The method of claim 1 wherein the heat treatment is at a temperature of from about 200° C. to about 350° C.
Claim 16
Dependent Claim
22 words
The method of claim 1 wherein the heat treatment is at a temperature of from about 250° C. to about 350° C.
Claim 17
Dependent Claim
18 words
A liquid crystal display alignment layer on an electrode prepared in accordance with the method of claim 1.
Claim 18
Dependent Claim
20 words
The method of claim 1 further comprising the step of rubbing the polymer surface in order to orient the polymer.
Claim 19
Dependent Claim
22 words
A liquid crystal display device having at least one liquid crystal alignment layer prepared in accordance with the method of claim 17.
Claim 20
Dependent Claim
54 words
The liquid crystal display device of claim 18 wherein the monomer is of the formula: ##STR21## wherein R 8 is a C 1 -C 12 alkyl group, a C 1 -C 12 alkenyl group or either of the foregoing containing an Si or Ti atom or substituted with an Si or Ti containing group.
Claim 21
Dependent Claim
26 words
The method of claim 1 wherein the so formed liquid crystal alignment layer is subsequently rubbed in order to impart orientation characteristics to the alignment layer.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-04-05 | 1996-10-05 | 1997-04-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-04-05 | 2000-10-05 | 2001-04-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-04-05 | 2004-10-05 | 2005-04-06 | $7700.00 | Window Closed / Lapsed |