Compound for organic light-emitting device, cross-linked material thereof, and organic light-emitting device including cross-linked material
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.
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 polymer comprises a repeating unit (2) selected from repeating units represented by Formulae 6-1 to 6-4:
wherein, in Formulae 6-1 to 6-4,
R 61 is selected from hydrogen, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group,
R 62 to R 69 are each independently selected from hydrogen, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group; and
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from —F, —Cl, —Br, —I, —C(═O)—, a cyano group, and a nitro group,
R 62 and R 63 are optionally bound to each other to form a ring, and
* and *′ each indicate a binding site to an adjacent atom.
18. The cross-linked material of claim 13 , wherein the polymer comprises a repeating unit (2) selected from repeating units represented by Formulae 6-21 to 6-34:
wherein, in Formulae 6-21 and 6-34,
* and *′ each indicate a binding site to an adjacent atom.
19. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer and at least one cross-linked material of claim 13 .
20. The organic light-emitting device of claim 19 , wherein the emission layer comprises the at least one cross-linked material.