Fill port seal with first and second photosensitizers

• US 4,494,825 A
• Filed: 03/03/1982
• Issued: 01/22/1985
• Est. Priority Date: 03/04/1981
• Status: Expired due to Term

• Current Assignee: Hitachi, Ltd.
• Original Assignee: Hitachi, Ltd.
• Inventors: Matsuyama, Shigeru, Sasaki, Ken, Ichihara, Kazuyoshi, Koyama, Masaharu
• Primary Examiner(s): Corbin, John K.
• Assistant Examiner(s): Lewis, David
• Application Number:
  US06/354,183
• Time in Patent Office: 1,056 Days
• Field of Search: 350/343, 350/342, 204/159.15, 204/159.16, 204/159.17, 204/159.23, 525/7.1
• US Class Current: 349/154
• CPC Class Codes: G02F 1/1341 Filling or closing of cells

Abstract

A liquid crystal display device, wherein a fill port for inserting a liquid crystal composition thereinto is sealed by using a photo-setting resin composition comprising an acrylic or methacrylic type resin as a major resin component and two or more photosensitizers different in quality, is excellent in reliability and the sealed portion of the fill port can sufficiently and uniformly be cured both in surface and inner portions by irradiation of light in a short time.

Claims

1. A liquid crystal display device comprising a pair of substrates which are placed in parallel and at least one of which is transparent, the peripheries of said substrates being sealed by a sealant to form an inner cavity with a fill port, said inner cavity being filled with a liquid crystal composition, the inner surfaces of said substrates facing each other having electrodes and orientation controlling films thereon, and said fill port being sealed by using a photo-setting resin composition comprising an acrylic or methacrylic type resin as a major resin component and two or more photosensitizers different in quality, wherein the photosensitizers different in quality are comprised of at least one first photosensitizer which can reduce the curing time of the resin composition greatly and at least one second photosensitizer which can reduce the curing time of the resin composition not so greatly as the first photosensitizer, and wherein the at least one first photosensitizer is selected from the group consisting of β

-naphthalene sulfochloride, 1-butylnaphthalene-sulfonic acid-2-chloride, 1,4-dibutylnaphthalene sulfonic acid-2-chloride, p,p-ditolyl disulfide, β

,β

-dinaphthalene disulfide, decyl chloride, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin sec-butyl ether, benzoin isobutyl ether, di-tert-butyl peroxide, 2-methylanthraquinone, 1,5-dinitroanthraquinone, and anthraquinone, and the at least one second photosensitizer is selected from the group consisting of benzene-sulfochloride, diphenyl disulfide, tetramethylthiuram disulfide, bis(2-benzthiazyl) disulfide, dibenzyl ketone, Michler'"'"'s ketone, phenyl acetone, benzophenone, 4-methoxy benzophenone, acetophenone, acetylacetone, benzoin phenyl acetate, benzoin tert-butyl ether, furoin, furoin methyl ether and tert-butyl perbenzoate.

2. A liquid crystal display device according to claim 1, wherein the photosensitizers as a whole are used in an amount of 1 to 10% by weight based on the weight of the resin component.

3. A liquid crystal display device according to claim 1, wherein the photosensitizers are a combination of a hydrogen withdrawing type and a radical generating type.

4. A sealing medium for sealing a fill port for inserting a liquid crystal composition into a liquid crystal display device which comprises an acrylic or methacrylic type resin as a major resin component and two or more photosensitizers different in quality, wherein the photosensitizers different in quality are composed of at least one first photosensitizer which can reduce the curing time of the resin component and at least one second photosensitizer which can reduce the curing time of the resin component not so greatly as the first photosensitizer, and wherein the at least one first photosensitizer is selected from the group consisting of β

-naphthalene sulfochloride, 1-butylnaphthalene-sulfonic acid-2-chloride, 1,4-dibutylnaphthalene sulfonic acid-2-chloride, p,p-ditolyl disulfide, β

,β

-dinaphthalene disulfide, decyl chloride, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin sec-butyl ether, benzoin isobutyl ether, di-tert-butyl peroxide, 2-methylanthraquinone, 1,5-dinitroanthraquinone, and anthraquinone, and the at least one second photosensitizer is selected from the group consisting of benzene-sulfochloride, diphenyl disulfide, tetramethylthiuram disulfide, bis(2-benzthiazyl) disulfide, dibenzyl ketone, Michler'"'"'s ketone, phenyl acetone, benzophenone, 4-methoxy benzophenone, acetophenone, acetylacetone, benzoin phenyl acetate, benzoin tert-butyl ether, furoin, furoin methyl ether and tert-butyl perbenzoate.

5. A sealing medium according to claim 4, wherein the weight ratio of said at least one first photosensitizer to said at least one second photosensitizer is in the range of 1/9 to 9/1.

6. A sealing medium according to claim 4, wherein the photosensitizers are a combination of 2-methylanthraquinone and benzophenone.

7. A sealing medium according to claim 4, wherein the photosensitizers are used in an amount of 1 to 10% by weight based on the weight of the resin component.

8. A sealing medium according to claim 4, wherein the photosensitizers are a combination of a hydrogen withdrawing type and a radical generating type.

9. A sealing medium according to claim 4, wherein the resin has a molecular weight of at least 10,000.

10. A liquid crystal display device comprising a pair of substrates which are placed in parallel and at least one of which is transparent, the peripheries of said substrates being sealed by a sealant to form an inner cavity with a fill port, said inner cavity being filled with a liquid crystal composition, the inner surfaces of said substrates facing each other having electrodes and orientation controlling films thereon, and said fill port being sealed by using a photo-setting resin composition comprising an acrylic or methacrylic type resin as a major resin component and two or more photosensitizers different in quality, wherein the photosensitizers different in quality are comprised of at least one first photosensitizer which can reduce the curing time of the resin composition greatly and at least one second photosensitizer which can reduce the curing time of the resin composition not so greatly as the first photosensitizer, and wherein the photosensitizers are a combination of 2-methylanthraquinone and benzophenone.