Acrylic pressure-sensitive adhesive comprising optically anisotropic compound, polarizing plate and liquid crystal display including the same

Patent metadata

Field	Value
Publication number	US-9045671-B2
Application number	US-86510909-A
Country	US
Kind code	B2
Filing date	Feb 2, 2009
Priority date	Feb 1, 2008
Publication date	Jun 2, 2015
Grant date	Jun 2, 2015

Abstract

Disclosed are (A) an acrylic pressure-sensitive adhesive; and (B) an acrylic pressure-sensitive adhesive comprising an optically anisotropic compound having at least one substituent which contains an alkyl group, alkenyl group or alkynyl group at a meta-position of a mesogen. A polarizing plate and a liquid crystal display using the same are also disclosed. The optically anisotropic compound ensures excellent compatibility with the adhesive and high birefringence. Thus, main properties such as adhesion, reliability and durability in the conditions of high temperatures or high temperatures and high humidity are not worsened. Moreover light leakage is prevented by efficiently controlling the birefringence caused by shrinkage stress of the polarizing plate.

First claim

The invention claimed is:

1. An acrylic pressure-sensitive adhesive composition, comprising:
(A) 100 parts by weight of acrylic copolymer; and
(B) 5 to 30 parts by weight of an optically anisotropic compound comprising one or more substituents containing one of an alkyl group, an alkenyl group, and an alkynyl group in a meta position of mesogen expressed by Formula 2:

Z is C—W or N;
Q 1 through Q 15 , and W are, independently of one another, hydrogen, halogen, cyano, —R 5 , —OR 5 , —NR 5 R 5 or —C(═O)R 5 , respectively; and
l, m, and n are, independently of one another, an integer of 0 to 3, and l+m+n is an integer of 1 or over; and
Y, G 1 , G 2 , X 1 , and X 2 are, independently of one another, a single bond, —O—, —S—, —SO—, —SO 2 —, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene, or —U-T-V—, respectively,
wherein -T- indicates carbonyl (—C(═O)—), U and V indicate a single bond, —O—, —NR 5 —, —S—, —(CH 2 ) p —, —O(CH 2 ) p —, —(CH 2 ) p O—, respectively, and p indicates an integer of 1 to 5;
E indicates hydrogen, halogen, cyano, —NCO, —NCS, —R 5 , or —OR 5 ; and
R 3 , R 4 , and R 5 , indicate, independently of one another, hydrogen, C 1 -C 20 alkyl unsubstituted or substituted with one or more halogens, C 2 -C 20 alkenyl unsubstituted or substituted with one or more halogens, C 2 -C 20 alkynyl unsubstituted or substituted with one or more halogens, or —(R 6 O) q R 7 , in which R 6 indicates C 1 -C 6 alkylene, R 7 indicates C 1 -C 4 alkyl, and q indicates an integer of 1 to 5, where both of R 3 and R 4 are not hydrogen at the same time;
with the proviso that at least two of l, m and n is more than 0 and at least one of G 1 and G 2 is —O—, —NR 5 —, —S—, —SO—, —SO 2 —, C 1 -C 6 alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene, or —U-T-V—, respectively.

2. The acrylic pressure-sensitive adhesive composition of claim 1 , wherein the acrylic copolymer (A) is an aromatic group-containing acrylic copolymer.

3. The acrylic pressure-sensitive adhesive composition of claim 2 , wherein the aromatic group-containing acrylic copolymer comprises:
i) a (meth)acrylic acid ester monomer having an alkyl group of 1 to 14 carbon atoms;
ii) a crosslinking functional group-containing monomer; and
iii) an aromatic group-containing acrylic monomer that can be copolymerized with the (meth)acrylic acid ester monomer.

4. The acrylic pressure-sensitive adhesive composition of claim 3 , wherein the aromatic group-containing acrylic monomer iii) is a compound expressed by Formula 1:

where R 1 indicates hydrogen or a methyl group,
R 2 indicates an alkylene group of 1 to 12 carbon atoms,
n indicates an integer of 0 to 3,
X indicates oxygen, sulfur, or an alkylene group of 1 to 4 carbon atoms, and
Ar indicates an aromatic group unsubstituted or substituted with halogen or alkyl of 1 to 12 carbon atoms.

5. The acrylic pressure-sensitive adhesive composition of claim 4 , wherein the compound expressed by Formula 1 is one or more selected from the group consisting of phenoxy ethyl (meth)acrylate, benzyl (meth)acrylate, 2-phenylthio-1-ethyl (meth)acrylate, 6-(4,6-dibromo-2-isoprophyl phenoxy)-1-hexyl (meth)acrylate, 6-(4,6-dibromo-2-sec-butyl phenoxy)-1-hexyl (meth)acrylate, 2,6-dibromo-4-nonylphenyl (meth)acrylate, 2,6-dibromo-4-dodecyl phenyl (meth)acrylate, 2-(1-naphtyloxy)-1-ethyl (meth)acrylate, 2-(2-naphtyloxy)-1-ethyl (meth)acrylate, 6-(1-naphtyloxy)-1-hexyl (meth)acrylate, 6-(2-naphtyloxy)-1-hexyl (meth)acrylate, 8-(1-naphtyloxy)-1-octyl (meth)acrylate, and 8-(2-naphtyloxy)-1-octyl (meth)acrylate.

6. The acrylic pressure-sensitive adhesive composition of claim 1 , wherein in the compound expressed by Formula 2, Y, G 1 , and G 2 are, independently of one another, a single bond, —O—, NR 5 , —S—, —SO—, —SO 2 —, —(CH 2 ) p —, —CH═CH—, —C≡C—, —C(═O)O—, —OC(═O)—, —C(═O)—, C(═O)NR 5 , NR 5 C(═O), —C(═O)S—, —SC(═O)—, —C(═O)O(CH 2 ) p —, —OC(═O)(CH 2 ) p —, —(CH 2 ) p OC(═O)—, or —(CH 2 ) p C(═O)O—, respectively, and p indicates an integer of 1 to 5.

7. The acrylic pressure-sensitive adhesive composition of claim 1 , wherein in the compound expressed by Formula 2, G 1 and G 2 are, independently of each another, a single bond, —CH═CH—, or respectively.

8. The acrylic pressure-sensitive adhesive composition of claim 1 , wherein in the compound expressed by Formula 2, X 1 and X 2 are, independently of each other, a single bond, —O—, NR 5 , —S—, —SO—, —SO 2 —, —(CH 2 ) p —, C(═O)NR 5 , NR 5 C(═O), NR 5 C(═O) NR 5 , —C(═O)O—, —OC(═O)—, or —OC(═O)O—, respectively, and p indicates an integer of 1 or 2.

9. The acrylic pressure-sensitive adhesive composition of claim 1 , wherein in the compound expressed by Formula 2, R 3 and R 4 are C 3 -C 12 alkyl unsubstituted or substituted with one or more halogens, C 3 -C 12 alkenyl unsubstituted or substituted with one or more halogens, or linear or branch C 3 -C 12 alkynyl unsubstituted or substituted with one or more halogens, respectively.

10. The acrylic pressure-sensitive adhesive composition of claim 1 , wherein in the compound expressed by Formula 2, R 3 , R 4 , and R 5 are, independently of one another, —(CH 2 CH 2 O) q CH 3 , —(CH 2 CHCH 3 O) q CH 3 , or —(CHCH 3 CH 2 O) q CH 3 , respectively, and q indicates an integer of 1 to 5.

11. The acrylic pressure-sensitive adhesive composition of claim 1 , further comprising (C) a low molecular weight material having a weight average molecular weight of 1,000 to 30,000 or a plasticizer.

12. The acrylic pressure-sensitive adhesive composition of claim 11 , wherein the plasticizer (C) is one or more selected from the group consisting of a phthalic acid-based plasticizer, a fatty acid ester-based plasticizer, a phosphoric ester-based plasticizer, an epoxy-based plasticizer, a trimellitate-based plasticizer, a pyromellitate-based plasticizer, a benzoic acid-based plasticizer, a polyester-based plasticizer, and a sulfonic acid ester-based plasticizer.

13. The acrylic pressure-sensitive adhesive composition of claim 1 , further comprising a multifunctional crosslinking agent.

14. The acrylic pressure-sensitive adhesive composition of claim 13 , wherein the multifunctional crosslinking agent is one or more kinds selected from the group consisting of an isocyanate compound, an epoxy compound, an aziridine compound, and a metal chelate compound.

15. The acrylic pressure-sensitive adhesive composition of claim 13 , wherein the content of the multifunctional crosslinking agent is 0.01 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer (A).

16. A polarizer comprising:
a polarization film; and
a pressure-sensitive adhesive layer formed on one side or both sides of the polarization film and containing the pressure-sensitive adhesive composition according to claim 1 .

17. A liquid crystal display (LCD) device comprising a liquid crystal panel in which the polarizer according to claim 16 is attached onto one side or both sides of a liquid crystal cell.

Assignees

• Han In Cheon
• Jang Ki Seok
• Park Min Soo
• Ko Min Jin
• Chol Bum Gyu
• Cho Ik Hwan
• Lee Ki Youl
• Lg Chemical Ltd

Inventors

• Han In Cheon
• Jang Ki Seok
• Park Min Soo
• Ko Min Jin
• Chol Bum Gyu
• Cho Ik Hwan
• Lee Ki Youl

Classifications

• C09J133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C08F2220/1825

  Chemistry & Metallurgy · mapped topic

• C08F2220/281

  Chemistry & Metallurgy · mapped topic

• C08F220/12

  of monohydric alcohols or phenols · CPC title