IP Library Granted Patent US 11,161,980
Granted Patent B2
US 11,161,980 · App. 16/510,369 · Granted Nov 2, 2021

Composition comprising polymer and inorganic particles, polyimide-inorganic particles composite, article including the composite, and optical device including the article

Inventors: Won Joon Cho (Suwon-si, KR); Young Jae Kang (Suwon-si, KR); Hyun Seok Choi (Anyan -si, KR); Eun Sung Lee (Hwaseong-si, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG DISPLAY CO., LTD.
C08L79/08C08K3/22C08K5/52C08K2003/2241C08K2201/011C08L77/06C08L2203/16
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Quick Facts
Patent No.
US 11,161,980
App. No.
16/510,369
Granted
Nov 2, 2021
Kind
B2
Abstract

A composition including a polymer including at least one of an amic acid structural unit and an imide structural unit, inorganic particles, and a compound represented by Chemical Formula 1, a polymer-inorganic particle composite prepared from the composition, an article, and an optical device including the article: In Chemical Formula 1, R 1 is a linear or branched, substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and n is an integer of 1 or more.

Claims (43)

1. A composition comprising

a polymer comprising an amic acid structural unit, an imide structural unit, or a combination thereof,

inorganic particles, and

a compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

R 1 is a linear or branched, substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and

n is an integer of 1 or more.

2. The composition of claim 1 , wherein R 1 of Chemical Formula 1 is a linear or branched C1 to C20 alkyl group.

3. The composition of claim 1 , wherein n of Chemical Formula 1 is an integer greater than or equal to 5 and less than or equal to 20.

4. The composition of claim 1 , wherein the inorganic particle is an oxide, a hydroxide, a carboxylate, or a nitride of Ti, Si, Al, Zr, Zn, Sn, B, Ce, Sr, Ca, Ba, In, or W, a graphene oxide, or a combination thereof.

5. The composition of claim 1 , wherein the inorganic particle is silica, alumina, titania, strontium titanate, zirconia, zinc oxide, indium tin oxide, strontium carbonate, zirconium tungsten oxide, antimony-doped tin oxide, graphene oxide, or a combination thereof.

6. The composition of claim 1 , wherein the inorganic particles are titania nanorods.

7. The composition of claim 6 , wherein the inorganic particles have an average particle diameter of a longest particle diameter of less than or equal to 50 nanometers.

8. The composition of claim 1 , wherein the inorganic particles are present in the composition in an amount of less than or equal to 50 parts by weight based on 100 parts by weight of the polymer.

9. The composition of claim 1 , wherein the compound represented by Chemical Formula 1 is present in the composition in an amount of less than 300 parts by weight based on 100 parts by weight of the inorganic particle.

10. The composition of claim 1 , wherein the composition further comprises a solvent.

11. The composition of claim 1 , wherein the amic acid structural unit is represented by Chemical Formula 2, and the imide structural unit is represented by Chemical Formula 3:

wherein, in Chemical Formula 2 and Chemical Formula 3,

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, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R 11 is a substituted or unsubstituted C4 to C20 aliphatic cyclic group, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the substituted or unsubstituted aromatic organic group is a single ring; a fused ring comprising two or more aromatic rings; or a ring system comprising two or more substituted or unsubstituted single or fused aromatic rings linked by a single bond, 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 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 integers of 0 to 3.

12. The composition of claim 11 , wherein in Chemical Formula 2 or Chemical Formula 3,

R 10 is a single bond, or a substituted or unsubstituted C1 to C30 aliphatic organic group,

R 11 is a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the substituted or unsubstituted C6 to C30 aromatic organic group is a ring system comprising two or more single or fused aromatic rings linked by a single bond, 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 12 and R 13 are independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aromatic organic group, and

n7 and n8 are independently 0 or 1.

13. The composition of claim 11 , wherein in Chemical Formula 2 or Chemical Formula 3,

R 10 is a single bond, or a C1 to C10 alkylene group substituted with a haloalkyl group,

R 11 is two substituted phenylene groups linked by a single bond, a fluorenylene group, a substituted or unsubstituted phenylene 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 12 and R 13 are independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, and

n7 and n8 are independently 0 or 1.

14. The composition of claim 11 , wherein Chemical Formula 2 is represented by Chemical Formula 2-1, Chemical Formula 2-2, or a combination thereof, and Chemical Formula 3 is represented by Chemical Formula 3-1, Chemical Formula 3-2, or a combination thereof:

15. The composition of claim 11 , wherein the polymer further comprises an amide structural unit represented by Chemical Formula 4:

wherein, in Chemical Formula 4,

R 5 is a substituted or unsubstituted C6 to C30 aromatic organic group,

R 6 is a single bond, 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 7 and R 8 are independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, C6 to C20 aromatic organic group, —OR 200 (wherein R 200 is a C1 to C10 aliphatic organic group), or a silyl group (—SiR 201 R 202 R 203 , wherein R 201 , R 202 , and R 203 are independently hydrogen, a C1 to C10 aliphatic organic group), and

n9 and n10 are independently integers of 0 to 4.

16. A polyimide-inorganic particle composite manufactured from the composition of claim 1 .

17. An article comprising the polyimide-inorganic particle composite of claim 16 .

18. The article of claim 17 , wherein the article is a film.

19. An optical device comprising the article of claim 17 .

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: CHO, WON JOON; KANG, YOUNG JAE; CHOI, HYUN SEOK; LEE, EUN SUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 051241/0140 →
Priority Claims (1)
KR 10-2018-0081628 · Jul 13, 2018 · national
Continuity (1)
Related Publication 20200017683A1 · Jan 16, 2020