Compound for organic light-emitting device, cross-linked material thereof, and organic light-emitting device including cross-linked material

Patent metadata

Field	Value
Publication number	US-10056552-B2
Application number	US-201615176646-A
Country	US
Kind code	B2
Filing date	Jun 8, 2016
Priority date	Dec 8, 2015
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

A compound for an organic light-emitting device represented by Formula 1:

wherein, in Formula 1,
A 1 is selected from an aromatic group and an aromatic group having extended π-conjugation,
R 1 is selected from hydrogen and a C 1 -C 60 alkyl group,
L 1 and L 2 are each independently selected from —O—, —S—, a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group; and
a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group, each substituted with at least one selected from a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group,
n1 and n2 are each independently selected from 0, 1, 2, 3, 4, and 5,
R 2 and R 3 are each independently selected from hydrogen and a first cross-linking group, provided that at least one of R 2 and R 3 is the first cross-linking group, and
X is selected from —F, —Cl, —Br, and —I.

First claim

What is claimed is:

1. A compound for an organic light-emitting device represented by Formula 1:

wherein, in Formula 1,
A 1 is selected from an aromatic group and an aromatic group having extended π-conjugation,
R 1 is selected from hydrogen and a C 1 -C 60 alkyl group,
L 1 and L 2 are each independently selected from —O—, —S—, a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group; and
a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group, each substituted with at least one selected from a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group,
n1 and n2 are each independently selected from 0, 1, 2, 3, 4, and 5,
R 2 and R 3 are each independently selected from hydrogen and a first cross-linking group, provided that at least one of R 2 and R 3 is the first cross-linking group, and
X is selected from —F, —Cl, —Br, and —I.

2. The compound of claim 1 , wherein the first cross-linking group comprises at least one carbon-carbon double bond.

3. The compound of claim 1 , wherein the first cross-linking group comprises a substructure represented by one of Formulae 3-1 and 3-2:

wherein, in Formulae 3-1 and 3-2,
A 31 is selected from a C 5 -C 10 carbocyclic group and a C 1 -C 10 heterocyclic group; and
a C 5 -C 10 carbocyclic group and a C 1 -C 10 heterocyclic group, each substituted with at least one selected from —F, —Cl, —Br, —I, —C(═O)—, a cyano group, a nitro group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group,
R 31 to R 33 are each independently selected from hydrogen, —F, —Cl, —Br, —I, —C(═O)—, a cyano group, a nitro group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group, and
* indicates a binding site to an adjacent atom.

4. The compound of claim 1 , wherein
the first cross-linking group is selected from a vinyl group, a maleimide group, a styrene group, and an acrylate group; and
a vinyl group, a maleimide group, a styrene group, and an acrylate group, each substituted with at least one selected from —F, —Cl, —Br, —I, —C(═O)—, a cyano group, a nitro group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group.

5. The compound of claim 1 , wherein the first cross-linking group is selected from groups represented by one of Formulae 3-11 to 3-14:

wherein, in Formulae 3-11 to 3-14,
R 31 to R 34 are each independently selected from hydrogen, —F, —Cl, —Br, —I, —C(═O)—, a cyano group, a nitro group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group, and
* indicates a binding site to an adjacent atom.

6. The compound of claim 1 , wherein A 1 is selected from a phenyl group and a naphthyl group.

7. The compound of claim 1 , wherein R 1 is hydrogen.

8. The compound of claim 1 , wherein L 1 and L 2 are each independently selected from —O— and a C 1 -C 20 alkylene group.

9. The compound of claim 1 , wherein R 2 and R 3 are each independently selected from hydrogen and groups represented by Formulae 3-11 to 3-14, provided that at least one of R 2 and R 3 is selected from groups represented by Formulae 3-11 to 3-14:

wherein, in Formulae 3-11 to 3-14,
R 31 to R 34 are each independently selected from hydrogen, —F, —Cl, —Br, —I, —C(═O)—, a cyano group, a nitro group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group, and
b34 is selected from 1, 2, 3, and 4, and
* indicates a binding site to an adjacent atom.

10. The compound of claim 1 , wherein R 2 and R 3 are each the first cross-linking group.

11. The compound of claim 1 , wherein X is —Br.

12. The compound of claim 1 , wherein the compound for an organic light-emitting device is represented by Compound DA1:

13. A cross-linked material of a compound for an organic light-emitting device represented by Formula 1 and a polymer:

wherein, in Formula 1,
A 1 is selected from an aromatic group and an aromatic group having extended π-conjugation,
R 1 is selected from hydrogen and a C 1 -C 60 alkyl group,
L 1 and L 2 are each independently selected from —O—, —S—, a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group,
n 1 and n 2 are each independently selected from 0, 1, 2, 3, 4, and 5,
R 2 and R 3 are each independently selected from hydrogen and a first cross-linking group, provided that at least one of R 2 and R 3 is the first cross-linking group, and
X is selected from —F, —Cl, —Br, and —I.

14. The cross-linked material of claim 13 , wherein the cross-linked material comprises a constituent unit represented by one of Formulae 2-1 to 2-3:

wherein, in Formulae 2-1 to 2-3,
A 1 is selected from an aromatic group and an aromatic group having extended π-conjugation,
R 1 is selected from hydrogen and a C 1 -C 60 alkyl group,
L 1 and L 2 are each independently selected from —O—, —S—, a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group,
n 1 and n 2 are each independently selected from 0, 1, 2, 3, 4, and 5,
R 2 and R 3 are each independently selected from hydrogen and a first cross-linking group, provided that at least one of R 2 and R 3 is the first cross-linking group,
X is selected from —F, —Cl, —Br, and —I, and
* indicates a binding site to an adjacent atom.

15. The cross-linked material of claim 13 , wherein the polymer comprises a repeating unit (1) represented by Formula 4:

wherein, in Formula 4,
L 41 is selected from —O—, —S—, a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group; and
a C 1 -C 20 alkylene group, a C 1 -C 20 oxyalkylene group, and a C 1 -C 20 thioalkylene group, each substituted with at least one selected from a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group,
n 41 is selected from 0, 1, 2, 3, 4, and 5,
R 41 is selected from hydrogen, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group,
R 42 is a second cross-linking group, and
* and *′ each indicate a binding site to an adjacent atom.

16. The cross-linked material of claim 13 , wherein the polymer comprises a repeating unit (1) selected from repeating units represented by Formulae 4-11 and 4-12:

wherein, in Formulae 4-11 and 4-12,
* and *′ each indicate a binding site to an adjacent atom.

17. The cross-linked material of claim 13 , wherein the pol

Assignees

• Samsung Electronics Co Ltd
• Univ Michigan Regents

Inventors

• Noh Changho
• Kwon Min Sang
• Kim Jinsang
• Yu Youngchang

Classifications

• C08F212/18

  Chlorine · CPC title

• C07C47/575

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C08F12/18

  Chlorine · CPC title

• C08F222/328

  Alpha-cyano-acrylic acid with more than one oxygen in the ester moiety · CPC title

• C07D207/452

  with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom · CPC title