Coating composition and organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11737300-B2
Application number	US-201716335044-A
Country	US
Kind code	B2
Filing date	Nov 24, 2017
Priority date	Nov 25, 2016
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

The present disclosure relates to a coating composition and an organic light emitting device.

First claim

The invention claimed is:

1. A coating composition comprising an ionic compound including an anion group represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
R1 to R20 are the same as or different from each other, and each independently hydrogen; deuterium; F, a cyano group, a nitro group; —C(O)R 100 ; —OR 101 ; —SR 102 ; —SO 3 R 103 ; —COOR 104 ; —OC(O)R 105 ; —C(O)NR 106 R 107 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; and
R 100 to R 107 are the same as or different from each other, and each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group,
wherein at least one of R1 to R20 is F, a cyano group, or a substituted or unsubstituted fluoroalkyl group; and at least one of R1 to R20 is a curing group selected from any one of the following structural formulae:

wherein,
L is a direct bond; O; S; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group;
k is an integer of 1 or 2, and when k is 2, the Ls are the same as or different from each other; and
R21 is a substituted or unsubstituted alkyl group,
wherein the number of F in the anion group is from 8 to 20, and
provided that the anion group is not

2. The coating composition of claim 1 , wherein the number of the curing group in the anion group represented by Chemical Formula 1 is 1, 2 or 4.

3. The coating composition of claim 1 , wherein parts by weight of the F in the anion group is from 10 parts by weight to 45 parts by weight or less with respect to 100 parts by weight of the anion group.

4. The coating composition of claim 1 , wherein the number of the F, the cyano group, or the substituted or unsubstituted fluoroalkyl group in the anion group represented by Chemical Formula 1 is from 8 to 20.

5. The coating composition of claim 1 , wherein at least one benzene ring among the R1 to R5-bonding benzene ring, the R6 to R10-bonding benzene ring, the R11 to R15-bonding benzene ring, and the R16 to R20-bonding benzene ring in Chemical Formula 1 is selected from among the following structural formulae:

6. The coating composition of claim 1 , wherein at least one benzene ring among the R1 to R5-bonding benzene ring, the R6 to R10-bonding benzene ring, the R11 to R15-bonding benzene ring, and the R16 to R20-bonding benzene ring in Chemical Formula 1 is selected from among the following structural formulae:

7. A coating composition comprising an ionic compound including an anion group represented by any one selected from among the following structural formulae:

in the structural formulae, n is an integer of 1 to 3, m is an integer of 1 to 3, and m+n=4;
q is an integer of 0 to 3, r is an integer of 1 to 4, and q+r=4;
Z is deuterium; a halogen group; a nitro group; a cyano group; an amino group; —C(O)R 100 ; —OR 101 ; —SR 102 ; —SO 3 R 103 ; —COOR 104 ; —OC(O)R 105 ; —C(O)NR 106 R 107 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
1 is an integer of 1 to 4, and when 1 is 2 or greater, Zs are the same as or different from each other; and
R 100 to R 107 are the same as or different from each other, and each independently hydrogen;
deuterium; or a substituted or unsubstituted alkyl group,
provided that the anion group is not

8. The coating composition of claim 1 , wherein the ionic compound includes a cation group, and the cation group is selected from among monovalent cation groups, onium compounds or the following structural formulae:

in the structural formulae, X 1 to X 75 are the same as or different from each other, and each independently hydrogen; a cyano group; a nitro group; a halogen group; —COOR 104 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; or a substituted or unsubstituted aryl group, or a curing group;
R 104 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group;
p is an integer of 0 to 10; and
a is 1 or 2, b is 0 or 1, and a+b=2.

9. The coating composition of claim 8 , wherein the cation group is represented by any one of the following Chemical Formula 10 to Chemical Formula 15:

X 47 to X 50 , X 100 to X 129 and X 133 to X 142 are the same as or different from each other, and each independently hydrogen; a cyano group; a nitro group; a halogen group; —COOR 104 ; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted fluoroalkyl group; a substituted or unsubstituted aryl group; or a curing group; and
R 104 is a substituted or unsubstituted alkyl group.

10. The coating composition of claim 8 , wherein the cation group is any one selected from among the following structural formulae:

11. A coating composition comprising an ionic compound selected from among the following structural formulae:

Assignees

• Lg Chemical Ltd

Inventors

• Lee Ho Gyu
• Bae Jaesoon
• Seo Seog Jae
• Lee Jaechol
• Shin Jiyeon
• Baek Leehyeon

Classifications

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/155 Primary

  comprising dopants · CPC title

• C07F5/02 Primary

  Boron compounds · CPC title

• C08K5/56

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title

• C08K5/55

  Boron-containing compounds {(C08K5/0091 takes precedence)} · CPC title