Composition, electro-optic material, electro-optic device, and method for preparing electro-optic material

Patent metadata

Field	Value
Publication number	US-11267967-B2
Application number	US-202016907448-A
Country	US
Kind code	B2
Filing date	Jun 22, 2020
Priority date	Jun 26, 2019
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

A composition for preparing an electro-optic material including a first polyimide having a high molecular weight, and a second polyimide having a lower molecular weight and including a structural unit including a chromophore functional group in the side chain, an electro-optic material including the composition, an electro-optic device including the electro-optic material, and a method of preparing the electro-optic material.

First claim

What is claimed is:

1. A composition for preparing an electro-optic material, the composition comprising
a first polyimide having a high molecular weight, and a second polyimide having a lower molecular weight that includes a structural unit comprising a chromophore functional group in the side chain.

2. The composition of claim 1 , wherein the first polyimide has a weight average molecular weight of greater than or equal to about 100,000 grams per mole, and the second polyimide has a weight average molecular weight of less than or equal to about 50,000 grams per mole.

3. The composition of claim 1 , wherein a content of the structural unit comprising the chromophore functional group in the side chain is less than about 50 weight percent based on a total weight of the first polyimide and the second polyimide.

4. The composition of claim 1 , wherein a content of the structural unit comprising the chromophore functional group in the side chain is about 1 weight percent to about 30 weight percent based on a total weight of the first polyimide and the second polyimide.

5. The composition of claim 1 , wherein the first polyimide and the second polyimide are included in a weight ratio of about 99:1 to about 50:50.

6. The composition of claim 1 , wherein the first polyimide comprises a structural unit represented by Chemical Formula 1, and the second polyimide comprises a structural unit represented by Chemical Formula 2:

wherein, in Chemical Formula 1 and Chemical Formula 2,
D is independently a substituted or unsubstituted quadrivalent C4 to C30 alicyclic organic group, a substituted or unsubstituted quadrivalent C6 to C30 aromatic organic group, or a substituted or unsubstituted quadrivalent C4 to C30 heteroaromatic organic group, or a combination thereof,
E 1 is a substituted or unsubstituted divalent C1 to C30 aliphatic organic group, a substituted or unsubstituted divalent C4 to C30 alicyclic organic group, a substituted or unsubstituted divalent C6 to C30 aromatic organic group, a substituted or unsubstituted divalent C4 to C30 heteroaromatic organic group, or a combination thereof,
A is a substituted or unsubstituted C4 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C4 to C30 heteroaromatic organic group, or a combination thereof,
in D, E 1 , and A, the alicyclic organic group, the aromatic organic group, the heteroaromatic organic group, or the combination thereof is a single ring, a condensed ring in which at least two rings are fused, or at least two rings of the single ring or the condensed ring, each of which is linked to the other by a single bond, a fluorenylene group, —O—, —S—, —C(═O)—, —CH(OH)—, —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), —C(CF 3 )(C 6 H 5 )—, —C(═O)NH—, or a combination thereof,
X is a chromophore functional group, and
n of Chemical Formula 2 is one of integers of 1 to 4.

7. The composition of claim 6 , wherein D of Chemical Formula 1 and Chemical Formula 2 is independently selected from chemical formulae of Group 1:

wherein, in the above chemical formulae,
each moiety is substituted or unsubstituted, and each L is the same or different and is independently a single bond, fluorenylene group, —O—, —S—, —C(═O)—, —CH(OH)—, —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), —C(CF 3 )(C 6 H 5 )—, or —C(═O)NH—,
* is a linking portion with an adjacent atom,
Z 1 and Z 2 are each the same or different and are independently —N═ or —C(R 100 )═, wherein R 100 is hydrogen or a C1 to C5 alkyl group, provided that Z 1 and Z 2 are not simultaneously —C(R 100 )═, and
Z 3 is —O—, —S—, or —NR 101 —, wherein R 101 is hydrogen or a C1 to C5 alkyl group.

8. The composition of claim 6 , wherein E 1 of Chemical Formula 1 and A of Chemical Formula 2 are independently a substituted or unsubstituted C6 to C30 aromatic single ring, a C10 to C30 condensed ring in which at least two substituted or unsubstituted aromatic rings are fused, or at least two aromatic rings of the single ring or the condensed ring, each of which is linked to the other by a single bond, or —O—, —S—, —(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), C(CF 3 )(C 6 H 5 )—, —C(═O)NH—, or a combination thereof.

9. The composition of claim 6 , wherein E 1 of Chemical Formula 1 and A of Chemical Formula 2 are independently a group in which substituted or unsubstituted two phenylene groups are linked by a single bond, or —O—, —S—, —(CH 2 ) p —, —(CF 2 ) q —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, (wherein 1≤n≤10, 1≤p≤10, and 1≤q≤10), or a combination thereof and —(O—X)n linked with A of Chemical Formula 2 may include the two phenylene groups with which each —O—X is linked.

10. The composition of claim 1 , wherein the chromophore functional group is one or more of those represented by Chemical Formulae 3-1 to 3-8:

wherein, in Chemical Formulae 3-1 to 3-8,
R 1 to R 3 are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
A 1 is independently CH or N,
X 1 to X 3 are independently a C1 to C10 alkyl group that is substituted or unsubstituted with —NO 2 , —CN, or a sulfone group (—SO 2 ), —C(CN)═C(CN 2 ), R—(C═O)O— (wherein R is a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group), a halogen element, or a haloalkyl group,
n is one of integers of 1 to 11, and
* is a linking portion with the side chain of the second polyimide.

11. The composition of claim 1 , wherein the chromophore functional group is at least one of the following chemical formulae:

12. The composition of claim 1 , wherein the first polyimide comprises a structural unit represented by Chemical Formula 5, and the second polyimide comprises a structural unit represented by Chemical Formula 6:

wherein, in Chemical Formula 5 and Chemical Formula 6,
Y and L are independently, a single bond, —O—, —S—, —(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), —C(CF 3 )(C 6 H 5 )—, —C(═O)NH—, or a co

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Min Sang
• Jee Sang Soo
• Ko Yoon Seok
• Jeon Hyunjeong
• Ju Kyeong-Sik

Classifications

• G02B26/02

  for controlling the intensity of light {(G02B26/004 takes precedence)} · CPC title

• C08G73/1053

  with oxygen only in the tetracarboxylic moiety · CPC title

• G02F1/3612 Primary

  Heterocycles having N as heteroatom · CPC title

• C08G73/1075

  Partially aromatic polyimides · CPC title

• G02B26/08

  for controlling the direction of light (in light guides G02B6/35) · CPC title