Liquid crystal display and photopolymerizable sealant therefor

• US 4,297,401 A
• Filed: 12/26/1978
• Issued: 10/27/1981
• Est. Priority Date: 12/26/1978
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Chern, Mao-Jin, Lowrey, Robert D.
• Primary Examiner(s): MCCAMISH, MARION E
• Application Number:
  US05/973,149
• Time in Patent Office: 1,036 Days
• Field of Search: 428/1, 350/160 LC, 156/272, 156/330, 23/230 LC, 204/159.13, 204/159.11, 526/193, 526/194, 526/198
• US Class Current: 428/1.53
• CPC Class Codes: C08G 59/68 characterised by the catalysts used
• CPC Class Codes: C08G 65/105 Onium compounds
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C09J 163/00 Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
• CPC Class Codes: C09J 171/02 Polyalkylene oxides
• CPC Class Codes: C09K 2323/055 Epoxy
• CPC Class Codes: G02F 1/1339 Gaskets; Spacers; Sealing of cells

Abstract

A method of making a liquid crystal display cell wherein the planar glass plates of the cell are bonded together with a photopolymerizable epoxy-containing material to form a hermetically sealed cell and wherein the photocured seal is chemically resistant to the contents of the liquid crystals cell. Adhesion of the photopolymerizable epoxy material to the glass plates of the liquid crystal cell is improved by addition of glycidoxypropyl triethoxy silane or its precondensate.

Claims

1. An improved liquid crystal display cell comprising a pair of half-cells having portions thereof bonded together by organic seal means wherein the improvement comprises an organic seal means comprising a photopolymerized sealant comprising a polymerized mixture of:

(a) cationically polymerizable epoxide with a functionality of at least 1, and;

(b) an organic aromatic onium catalyst comprising an aromatic adduct of

(1) a diaromatic, triaromatic, or tetraaromatic organoatomic cation of a Group Va, VIa, or VIIa atom and

(2) an anion;

said onium catalyst being represented by the formula;

##STR5## wherein R² is an aromatic group at least as electron withdrawing as benzene,

R¹ is an alkyl or alkenyl group,

A is a Group Va, VIa, or VIIa atom,

X is an anion,

n is a positive whole integer of at least 2 up to the valence of A plus one,

a is 0 or a positive whole integer up to the valence of A minus one, and

n plus a is equal to the valence of A plus one and wherein at let two of said R² groups are bonded to A;

said photopolymerized sealant being chemically resistant to liquid crystal materials.

2. An improved liquid crystal display cell in accordance with claim 1, wherein said sealant comprises an adhesive-aiding amount of glycidoxpropyl triethoxy silane or its precondensate.

3. An improved liquid crystal display cell in accordance with claim 2, wherein said cationically polymerizable epoxide is selected from the group consisting of:

(a) a mixture of Bisphenol A diglycidyl ether epoxy, triglycidyl ether epoxies of trihydroxymethyl propane, and 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexene carboxylate, and;

(b) 3,4 epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate, and;

(c) Bisphenol A diglycidyl ether;

wherein said organic aromatic onium catalyst is triphenyl sulfonium hexafluorophosphate, and said adhesion-aiding amount of glycidoxypropyl triethoxy silane or its precondensate is 4-30% by weight of said photopolymerizable sealant.

4. An improved liquid crystal display cell in accordance with claim 1, wherein said seal means defines a plurality of cavities within said liquid crystal display cell.

5. An improved liquid crystal display cell in accordance with claim 1, wherein said display cell includes liquid crystal material disposed in said cell.

6. An improved multi-cavity liquid crystal display according to claim 1, 4 or 5 wherein:

(a) said cationically polymerizable epoxide is a mixture of 55 parts by weight Bisphenol A diglycidyl ether epoxy, 25 parts triglycidyl ether epoxies of trihydroxymethyl propane, and 20 parts 3,4-epoxy-cyclohexylmethyl-3,4-epoxycyclohexene carboxylate;

(b) said organic aromatic onium catalyst is triphenyl sulfonium hexafluorophosphate;

(c) said adhesion-aiding amount of glycidoxypropyl triethoxy silane or its precondensate is 4-30% by weight of said photopolymerizable sealant.

7. A process for bonding a radiation-transparent substrate to a second substrate comprising:

A. disposing a layer of an adhesive, sealant composition between said substrates and in contact therewith;

said sealant composition comprising;

(a) a cationically polymerizable epoxide with a functionality of at least 1, and

(b) an organic aromatic onium catalyst comprising an aromatic adduct of

(1) a diaromatic, triaromatic, or tetraaromatic organoatomic cation of a Group Va, VIa, or VIIa atom and

(2) an anion;

said onium catalyst being represented by the formula;

##STR6## wherein R² is an aromatic group at least as electron withdrawing as benzene,

R¹ is an alkyl or alkenyl group,

A is a Group Va, VIa, or VIIa atom,

X is an anion,

n is a positive whole integer of at least 2 up to the valence of A plus one,

a is 0 or a positive whole integer up to the valence of A minus one, and n plus a is equal to the valence of A plus one and wherein at least two of said R² groups are bonded to A, and

(c) an adhesion-aiding amount of glydicoxypropyl triethoxy silane or its precondensate; and

said sealant composition being chemically resistant to liquid crystal materials; and

B. exposing said layer to polymerizing radiation through said radiation-transparent substrate in an amount and for a time sufficient to polymerize said layer.

8. A process for bonding a radiation-transparent substrate to a second substrate according to claim 7 wherein, said radiation-transparent substrate and said second substrate are both portions of a liquid crystal display cell.

9. A method of bonding together corresponding half-cells of a liquid crystal display cell comprising:

(a) providing a pair of corresponding display half-cells

(b) applying a layer of photopolymerizable sealant to at least one of said half-cells in a pattern which, in cooperation with the corresponding half-cell, defines at least one cavity which can be filled with a liquid crystal material, said photopolymerizable composition being chemically resistant to liquid crystal materials, and said composition comprising;

(1) a mixture of 55 parts by weight Bisphenol A diglycidyl ether epoxy, 25 parts triglycidyl ether epoxies or trihydroxymethyl propane and 20 parts 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexene carboxylate;

(2) the organic aromatic onium catalyst triphenyl sulfonium hexafluorophosphate, and

(3) 4-30% by weight glycidoxypropyl triethoxy silane or its precondensate; and

(c) exposing said photopolymerizable composition to polymerizing radiation.

10. A method according to claim 9 wherein said pattern defines a plurality of cavities.

11. A method according to claim 9 or 10 wherein said cavity is subsequently filled with a liquid crystal material and the cavity is plugged.