Crosslinkable compound, composition containing same for formation of solid electrolyte, method for preparation of solid electrolyte by using same, and electronic element including same solid electrolyte

Patent metadata

Field	Value
Publication number	US-2024061335-A1
Application number	US-202218278921-A
Country	US
Kind code	A1
Filing date	Feb 3, 2022
Priority date	Feb 26, 2021
Publication date	Feb 22, 2024
Grant date	—

Abstract

The present disclosure relates to a crosslinkable compound, a composition containing the same for formation of a solid electrolyte, a method of preparing a solid electrolyte by using the composition, a solid electrolyte, and an electronic element including the solid electrolyte.

First claim

1 . A crosslinkable compound represented by Formula 1:

wherein, in Formula 1,
L 1 and L 2 are each independently a single bond, —C═O—, —C, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, or a substituted or unsubstituted C 2 -C 30 alkynylene group,
m1 and m2 are each independently 0, 1, 2, or 3,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
Ar 1 and Ar 2 are each independently substituted with at least one crosslinkable group,
n1 is an integer from 2 to 300,000,
R 1 to R 4 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 alkylthio group, —Si(Q 1 )(Q 2 )(Q 3 ), a substituted or unsubstituted C 5 -C 60 carbocyclic group, or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
at least one of the substituted C 1 -C 30 alkylene group, the substituted C 2 -C 30 alkenylene group, the substituted C 2 -C 30 alkynylene group, the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 30 alkyl group, the substituted C 2 -C 30 alkenyl group, the substituted C 2 -C 30 alkynyl group, the substituted C 1 -C 30 alkoxy group, and the substituted C 1 -C 30 alkylthio group is substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 3 o alkoxy group, a C 1 -C 30 alkylthio group, or —Si(Q 1 )(Q 2 )(Q 3 ), and
Q 11 to Q 13 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 3 o alkoxy group, or a C 1 -C 30 alkylthio group.

2 . The crosslinkable compound of claim 1 , wherein the crosslinkable group contains an azide group (—N 3 ), a sulfur-containing group, or an unsaturated double bond-containing group.

3 . The crosslinkable compound of claim 1 , wherein the crosslinkable compound is represented by Formula 2:

wherein, in Formula 2,
L 1 , L 2 , m1, m2, n1, and R 1 to R 4 are as defined in claim 1 ,
R 11 to R 15 and R 21 to R 25 are each independently a crosslinkable group, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 alkylthio group, —Si(Q 1 )(Q 2 )(Q 3 ), a substituted or unsubstituted C 5 -C 6 o carbocyclic group, or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
at least one of R 11 to R 15 is a crosslinkable group, and
at least one of R 21 to R 25 is a crosslinkable group.

4 . The crosslinkable compound of claim 3 , wherein
one of R 11 to R 15 is an azide group, and the others are each —F or —Cl, and one of R 21 to R 25 is an azide group, and the others are each —F or —Cl.

5 . The crosslinkable compound of claim 1 , wherein the crosslinkable compound is selected from Compounds 1 to 5:

6 . A composition for forming a solid electrolyte, comprising:
an ionic elastomer; an ionic liquid; and a photo-crosslinking agent, wherein the photo-crosslinking agent contains the crosslinkable compound of claim 1 .

7 . The composition of claim 6 , wherein the ionic elastomer is a thermoplastic polyurethane (TPU) polymer.

8 . The composition of claim 7 , wherein the TPU polymer contains a repeating unit represented by Formula 10:

wherein, in Formula 10,
n11 is an integer from 1 to 5,000, and
R 101 to R 122 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 alkylthio group, —Si(Q 1 )(Q 2 )(Q 3 ), a substituted or unsubstituted C 5 -C 60 carbocyclic group, or a substituted or unsubstituted C 1 -C 60 heterocyclic group.

9 . The composition of claim 6 , wherein the ionic liquid is a nitrogen-containing ionic liquid, a phosphorus (P)-containing ionic liquid, or any combination thereof.

10 . The composition of claim 6 , wherein
the ionic liquid contains a cation and an anion, the cation is an ammonium ion, an imidazolium ion, a piperidinium ion, a pyrrolidinium ion, a phosphonium ion, or any combination thereof, and the anion is a halogen ion, an acetate ion, a nitrate ion (NO 3 − ), a tetrafluoroborate ion (BF 4 − ), a hexafluorophosphate ion (PF 6 − ), a trifluoromethane sulfonate ion (Tf − ), a bis((trifluoromethyl)sulfonyl)imide ion (TFSI − ), or any combination thereof

11 . The composition of claim 6 , wherein a weight ratio of the photo-crosslinking agent to the ionic elastomer is 1:0.01 to 1:0.1.

12 . A method of preparing a solid electrolyte, the method comprising exposing the composition of claim 6 to ultraviolet (UV) rays.

13 . The method of claim 12 , further comprising forming a pattern by developing the UV-exposed composition for forming a solid electrolyte.

14 . A solid electrolyte prepared by using the composition of claim 6 .

15 . The solid electrolyte of claim 14 , wherein the solid electrolyte is stretchable.

16 . An electronic element comprising the solid electrolyte of claim 15 .

17 . The electronic element of claim 16 , wherein the electronic element is any one of an organic solar cell (OSC), an organic thin-film transistor (OTFT), an organic light-emitting diode (OLED), an organic photodiode sensor (OPD), a perovskite solar cell, a perovskite light-emitting diode, and a thermoelectric device.

Assignees

• Ulsan Nat Inst Science & Tech Unist
• Iucf Hyu

Inventors

• Kim Bong Soo
• Cho Wanho
• Kim Do Hwan
• Kweon Hyukmin
• Lee Chaeyoung
• Park Sangjun

Classifications

• G03F7/039 Primary

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• C08K5/28 Primary

  Azides · CPC title

• C08L75/04

  Polyurethanes · CPC title

• G03F7/2037

  Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation · CPC title

• Y02P70/50

  Manufacturing or production processes characterised by the final manufactured product · CPC title