IP Library › Granted Patent US 10,100,151
Granted Patent B2
US 10,100,151 · App. 14/550,716 · Granted Oct 16, 2018

Composition for preparing polyimide, polyimide, and article including same

Inventors: Jungha Chae (Yongin-si, KR); Byung Hee Sohn (Yongin-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C08G73/1067C08G73/1039C08G73/1042C08J5/18C09D179/08G02F1/133305C08J2379/08
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Quick Facts
Patent No.
US 10,100,151
App. No.
14/550,716
Granted
Oct 16, 2018
Kind
B2
Abstract

A composition for preparing a polyimide including a tetracarboxylic dianhydride mixture including a tetracarboxylic dianhydride represented by Chemical Formula 1A, Chemical Formula 1B, or a combination thereof, a tetracarboxylic dianhydride represented by Chemical Formula 2, and a diamine represented by Chemical Formula 3: NH 2 —R 1 —NH 2   Chemical Formula 3 wherein in Chemical Formulae 1A, 1B, 2 and 3, definitions of groups and substituents are described in the specification.

Claims (45)

1. An film prepared from a composition, the composition comprising:

a tetracarboxylic dianhydride represented by Chemical Formula 1A, Chemical Formula 1B, or a combination thereof,

a tetracarboxylic dianhydride represented by Chemical Formula 2, and

a diamine represented by the following chemical formula:

wherein in Chemical Formulae 1A, 1B, and 2,

R 10 is a single bond, a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R 12 and R 13 are the same or different and are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, a group of formula —OR 205 , wherein R 205 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 209 R 210 R 211 , wherein R 209 , R 210 , and R 211 are the same or different and are independently a hydrogen or a C1 to C10 aliphatic organic group,

L 1 and L 2 are the same or different and are independently a single bond or a C1-C5 alkylene group, and

n7 and n8 are the same or different and are independently an integer ranging from 0 to 3;

wherein the tetracarboxylic dianhydride represented by Chemical Formula 2 is included in an amount of greater than or equal to 40 mole % and less than or equal to 52 mole %, based on the total mole numbers of the tetracarboxylic dianhydride mixture wherein the thickness of the film is about 10 micrometers, and the out-of-plane retardation of the film is less than or equal to 92 nanometers.

2. The film according to claim 1 , wherein R 10 is a substituted or unsubstituted C1 to C15 alkylene group, a substituted or unsubstituted C1 to C15 fluoroalkylene group, a substituted or unsubstituted C1 to C15 heteroalkylene group, a substituted or unsubstituted C3 to C15 cycloalkylene group, a substituted or unsubstituted C3 to C15 heterocycloalkylene group, a substituted or unsubstituted C6 to C15 arylene group, or a substituted or unsubstituted C2 to C15 heteroarylene group.

3. The film according to claim 1 , wherein Chemical Formula 1A is represented by Chemical Formula 4 or Chemical Formula 5, and Chemical Formula 2 is represented by Chemical Formula 6 or Chemical Formula 7:

wherein in Chemical Formulae 4 to 7,

R 12 and R 13 are the same or different and are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group a group of formula —OR 200 , wherein R 200 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 201 R 202 R 203 , wherein R 201 , R 202 , and R 203 are the same or different and are independently a hydrogen or a C1 to C10 aliphatic organic group, and

n7 and n8 are the same or different and are independently an integer ranging from 0 to 3.

4. The film according to claim 1 , wherein Chemical Formula 1A is represented by Chemical Formula 18:

wherein in Chemical Formula 18,

R 10 is a single bond, a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R 12 and R 13 are the same or different and are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, a group of formula —OR 205 , wherein R 205 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 209 R 210 R 211 wherein R 209 , R 210 , and R 211 are the same or different and are independently a hydrogen or a C1 to C10 aliphatic organic group, and

n7 and n8 are the same or different and are independently an integer ranging from 0 to 2.

5. The film according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1A is one or more selected from 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 3,3,′4,4′-diphenylsulfone tetracarboxylic dianhydride, 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, and 4,4′-oxydiphthalic anhydride.

6. The film according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 2 is one or more selected from 2,3,3′,4′-biphenyl tetracarboxylic dianhydride, 2,3,3′,4′-diphenylsulfone tetracarboxylic dianhydride, and 3,4′-oxydiphthalic anhydride.

7. The film according to claim 1 , wherein the tetracarboxylic dianhydride represented by Chemical Formula 1A is 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, and the tetracarboxylic dianhydride represented by Chemical Formula 2 is 2,3,3′,4′-biphenyl tetracarboxylic dianhydride.

8. The film according to claim 1 , wherein the thickness of the film is about 10 micrometers, and the yellowness index of the film is less than about 4%.

9. A display device comprising the film according to claim 1 .

10. The display device according to claim 9 , wherein the display device is a liquid crystal display device.

11. An film comprising a polyimide represented by Chemical Formula 8, or a polyamic acid precursor of the polyimide:

wherein in Chemical Formula 8,

 is represented by Chemical Formula 9A or Chemical Formula 9B,

 is represented by Chemical Formula 10:

wherein in Chemical Formulae 9A, 9B, and 10,

R 10 is a single bond, a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R 12 and R 13 are the same or different and are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, a group of formula —OR 205 , wherein R 205 is a C1 to C10 aliphatic organic group, or a silyl group of formula—SiR 209 R 210 R 211 , wherein R 209 , R 210 , and R 211 are the same or different and are independently a hydrogen or a C1 to C10 aliphatic organic group,

L 1 and L 2 are the same or different and are independently a single bond or a C1-C5 lkylene group, and

n7 and n8 are the same or different and are independently an integer ranging from 0 to 3;

 is represented by the following chemical formulae:

x and y are mole fractions of each structure unit provided that x is 0.40≤x≤0.52, and y is y=1−x wherein the thickness of the film is about 10 micrometers, and the out-of-plane retardation of the film is less than or equal to 92 nanometers.

12. The film according to claim 11 , wherein Chemical Formula 9A is represented by Chemical Formula 11 or Chemical Formula 12, and Chemical Formula 10 is represented by Chemical Formula 13 or Chemical Formula 14:

wherein in Chemical Formulae 11 to 14,

R 12 and R 13 are the same or different and are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, a group of formula —OR 205 , wherein R 205 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 209 R 210 R 211 , wherein R 209 , R 210 , and R 211 are the same or different and are independently a hydrogen or a C1 to C10 aliphatic organic group, and

n7 and n8 are the same or different and are independently an integer ranging from 0 to 3.

13. The film according to claim 11 , wherein

is represented by Chemical Formula 15:

and

is represented by Chemical Formula 16:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2018
From: CHAE, JUNGHA; SOHN, BYUNG HEE
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 046143/0613 →
Priority Claims (2)
KR 10-2013-0144125 · Nov 25, 2013 · national
KR 10-2014-0162857 · Nov 20, 2014 · national
Continuity (1)
Related Publication 20150147554A1 · May 28, 2015
Cited By (1)
US 12,658,126