IP Library Granted Patent US 11,261,297
Granted Patent B2
US 11,261,297 · App. 16/283,207 · Granted Mar 1, 2022

Polymer, film including the polymer, and display device including the film

Inventors: Fedosya Kalinina (Hwaseong-si, KR); Dmitry Androsov (Suwon-si, KR); Hyunseok Choi (Seoul, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG DISPLAY CO., LTD.
C08G73/1067C08G73/0672C08G73/1014C08G73/1017C08G73/1039C08G73/1042C08G73/16C08G85/004C08L79/08C09D179/08G02B5/305C08L2201/10C08L2203/14
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Quick Facts
Patent No.
US 11,261,297
App. No.
16/283,207
Granted
Mar 1, 2022
Kind
B2
Abstract

A polymer is disclosed, represented by Chemical Formula 1 or Chemical Formula 2: wherein, in Chemical Formula 1 and Chemical Formula 2, Ar 1 , Ar 2 , R 3 , s, x, and y are defined in the detailed description.

Claims (55)

1. A polymer represented by Chemical Formula 1 or Chemical Formula 2:

wherein, in Chemical Formula 1 and Chemical Formula 2,

Ar 1 of Chemical Formula 1 or Chemical Formula 2 comprises a combination of a group represented by Chemical Formula 3 and a group represented by Chemical Formula 4 and optionally, a substituted or unsubstituted C6 to C30 aromatic organic group:

wherein, in Chemical Formula 3,

R 10 is a single bond, —O—, —S—, —C(═O)—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, —(CH 2 ) p —C(C n H 2n+1 ) 2 —(CH 2 ) q —, —(CH 2 ) p —C(C n F 2n+1 ) 2 —(CH 2 ) q — (wherein 1≤n≤10, 1≤p≤10, and 1≤q≤10), or a combination thereof,

R 12 and R 13 are independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, a —OR 201 group (wherein R 201 is a C1 to C10 aliphatic organic group), or a —SiR 210 R 211 R 212 (wherein R 210 , R 211 , and R 212 are independently hydrogen or a C1 to C10 aliphatic organic group) group, and

n7 and n8 are independently one of integers of 0 to 3;

wherein, in Chemical Formula 4,

R 1 and R 2 are independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 acyl group, a hydroxy group, a halogen, a nitro group, —NR′R″ (wherein R′ and R″ are independently hydrogen, a C1 to C30 alkyl group, or a C6 to C30 aryl group), —SiR′R″R′″ (wherein R′, R″, and R′″ are independently hydrogen, a C1 to C30 alkyl group, or a C6 to C30 aryl group), or a combination thereof,

L 1 is O,

A 1 is a phenyl or phenylene group,

R a is hydrogen, a C1 to C30 alkyl group, a C6 to C30 aryl group, a C7 to C30 arylalkyl group, —F, —Cl, —NR′R″, —CONR′R″ (wherein R′ and R″ are independently hydrogen, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C7 to C30 arylalkyl group), or a group represented by Chemical Formula 5:

* L 2 - A 2 q L 3 - A 3 ) r ]  Chemical Formula 5

wherein, in Chemical Formula 5,

L 2 and L 3 are independently O, CO, COO, C≡C, or CONR b (wherein R b is hydrogen or a C1 to C30 alkyl group),

A 2 and A 3 are independently a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C30 arylalkylene or arylalkyl group,

q and r are independently an integer ranging from 0 to 3,

k is an integer of 1,

m is an integer ranging from 0 to 2,

n is an integer ranging from 1 to 3, and

o and p are independently an integer ranging from 0 to 3;

Ar 2 is a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the substituted or unsubstituted C6 to C30 aromatic organic group is present as a substituted or unsubstituted single aromatic ring; a fused ring comprising two or more substituted or unsubstituted aromatic rings; or a ring system comprising two or more of the substituted or unsubstituted single aromatic ring and/or the fused ring that are linked by a single bond, or a fluorenylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C6 to C15 arylene group, —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p — (wherein, 1≤p≤10), —(CF 2 ) q — (wherein, 1≤q≤10), —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —C(═O)NH—, or a combination thereof;

R 3 is hydrogen, a halogen, a vinyl group, an ethynyl group, an isopropyl group, a sec-butyl group, a tert-butyl group, a C3 to C20 cycloalkyl group, a C6 to C20 aryl group, or a combination thereof;

s is an integer ranging from 1 to 30, and

x and y are independently an integer greater than or equal to 1.

2. The polymer of claim 1 , wherein R 10 of Chemical Formula 3 is a single bond, —O—, —S—, —C(═O)—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, —(CH 2 ) p —C(C n H 2n+1 ) 2 —(CH 2 ) q —, —(CH 2 ) p —C(C n F 2n+1 ) 2 —(CH 2 ) q — (wherein 1≤n≤10, 1≤p≤3, and 1≤q≤3), or a combination thereof.

3. The polymer of claim 1 , wherein R 10 of Chemical Formula 3 is a single bond, —O—, —S—, —C(═O)—, —S(═O) 2 —, —C(CF 3 ) 2 —, or a combination thereof.

4. The polymer of claim 1 , wherein

L 2 and L 3 of Chemical Formula 5 are independently COO, C≡C, or CONR b (wherein R b is hydrogen or a C1 to C20 alkyl group),

A 2 and A 3 are independently a substituted or unsubstituted C6 to C20 aromatic ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C20 arylalkylene or arylalkyl group, and

q and r are independently an integer ranging from 0 to 2, provided that 1≤q+r≤2.

5. The polymer of claim 1 , wherein Ar 2 of Chemical Formula 1 or Chemical Formula 2 is a ring system that comprises two substituted or unsubstituted C6 to C30 aromatic rings linked by a single bond, or a fluorenylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C6 to C15 arylene group, —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p — (wherein, 1≤p≤10), —(CF 2 ) q — (wherein, 1≤q≤10), —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —C(═O)NH—, or a combination thereof.

6. The polymer of claim 1 , wherein Ar 2 of Chemical Formula 1 or Chemical Formula 2 is a ring system that comprises two substituted or unsubstituted C6 to C30 aromatic rings linked by a single bond.

7. The polymer of claim 1 , wherein R 3 of Chemical Formula 1 or Chemical Formula 2 is a hydrogen, a halogen, a vinyl group, an ethynyl group, an isopropyl group, a sec-butyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a phenyl group, or a combination thereof.

8. The polymer of claim 1 , wherein the group represented by Chemical Formula 3 and the group represented by Chemical Formula 4 in the combination are present in a mole ratio of about 1:99 to about 99:1.

9. The polymer of claim 1 ,

wherein in Chemical Formula 3, R 10 comprises a single bond, —C(CF 3 ) 2 —, or a combination thereof.

10. The polymer of claim 1 , which is a reaction product of reactants comprising a tetracarboxylic dianhydride represented by Chemical Formula 7, a tetracarboxylic dianhydride represented by Chemical Formula 8, a diamine represented by Chemical Formula 9, and a monoamine represented by Chemical Formula 10, and optionally a tetracarboxylic dianhydride having a substituted or unsubstituted C6 to C30 aromatic ring group:

wherein, in Chemical Formula 7,

R 10 , R 12 , R 13 , n7 and n8 are independently the same as defined in Chemical Formula 3;

wherein, in Chemical Formula 8,

R 1 , R 2 , R a , A 1 , L 1 , k, m, n, o, and p are independently the same as defined in Chemical Formula 4;

NH 2 —Ar 2 —NH 2   Chemical Formula 9

wherein, in Chemical Formula 9,

Ar 2 is the same as defined in claim 1 ;

NH 2 —(CH 2 ) s —R 3   Chemical Formula 10

wherein, in Chemical Formula 10,

R 3 and s are the same as defined in claim 1 .

11. The polymer of claim 10 , wherein a mole ratio between a total of the tetracarboxylic dianhydride represented by Chemical Formula 7, and the tetracarboxylic dianhydride represented by Chemical Formula 8, and optionally the tetracarboxylic dianhydride having a substituted or unsubstituted C6 to C30 aromatic ring group, and the diamine represented by Chemical Formula 9 in the reactants is about 1:0.8 to 0.95.

12. The polymer of claim 10 , wherein a mole ratio between a total of the tetracarboxylic dianhydride represented by Chemical Formula 7, and the tetracarboxylic dianhydride represented by Chemical Formula 8, and optionally the tetracarboxylic dianhydride having a substituted or unsubstituted C6 to C30 aromatic ring group, and the monoamine represented by Chemical Formula 10 in the reactants about 1:0.1 to 0.4.

13. A film comprising the polymer according to claim 1 .

14. The film according to claim 13 , wherein the film has a glass transition temperature of from about 160° C. to about 200° C.

15. The film according to claim 13 , wherein the film has a birefringence of greater than 0.05, measured at a wavelength of 450 nm by using a prism coupler.

16. An optical film comprising the film according to claim 13 , and a polarizer.

17. A display device comprising the film according to claim 13 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2020
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG DISPLAY CO., LTD.
Reel/Frame 051420/0824 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2019
From: KALININA, FEDOSYA; ANDROSOV, DMITRY; CHOI, HYUNSEOK
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 051241/0134 →
Priority Claims (1)
KR 10-2018-0021278 · Feb 22, 2018 · national
Continuity (1)
Related Publication 20190256659A1 · Aug 22, 2019