Compound and organic light emitting device comprising the same

Patent metadata

Field	Value
Publication number	US-12060372-B2
Application number	US-201917267560-A
Country	US
Kind code	B2
Filing date	Aug 26, 2019
Priority date	Aug 29, 2018
Publication date	Aug 13, 2024
Grant date	Aug 13, 2024

Abstract

Provided is a compound of Chemical Formula 1:

wherein:
Y is a direct bond, O or S; A 1 and A 2 are each independently a benzene ring, a naphthalene ring, or

 with the proviso that at least one of them is a naphthalene ring or

each X is independently CR 1 R 2 , SiR 3 R 4 , NR 5 , O, S, or SO 2 ;
R 1 to R 5 are each independently hydrogen, deuterium, or a substituted or unsubstituted: C 1-60 alkyl, C 3-60 cycloalkyl, or C 6-60 aryl;
L 1 and L 2 are each independently a direct bond, or a substituted or unsubstituted C 6-60 arylene or C 2-60 heteroarylene;
B 1 and B 2 are each independently *—NR 6 R 7 ; and
R′ 1 and R′ 2 are each independently hydrogen, deuterium, halogen, cyano, or a substituted or unsubstituted: C 1-60 alky, C 1-60 alkoxy, C 1-60 haloalkyl, C 1-60 haloalkoxy, tri(C 1-60 alkyl)silyl, or C 6-60 aryl; and
and an organic light emitting diode comprising: a first electrode; a second electrode opposite to the first electrode; and at least one organic material layer between the first electrode and the second electrode, wherein the organic material layer contains the compound of Chemical Formula 1.

First claim

The invention claimed is:

1. A compound of Chemical Formula 1:

wherein, in Chemical Formula 1:
Y is a direct bond, O or S;
A 1 and A 2 are each independently a benzene ring, a naphthalene ring, or

 with the proviso that at least one of A 1 and A 2 is a naphthalene ring or

each X is independently CR 1 R 2 , SiR 3 R 4 , NR 5 , O, S, or SO 2 ;
R 1 to R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1-60 alkyl, a substituted or unsubstituted C 3-60 cycloalkyl, or a substituted or unsubstituted C 6-60 aryl;
L 1 and L 2 are each independently a direct bond, a substituted or unsubstituted C 6-60 arylene, or a substituted or unsubstituted C 2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of N, O and S;
B 1 and B 2 are each independently *—NR 6 R 7 where *— means a bond linked to another substituent group;
R 6 and R 7 are each independently a substituted or unsubstituted C 1-60 alkyl, a substituted or unsubstituted C 1-60 alkoxy, a substituted or unsubstituted C 1-60 haloalkyl, a substituted or unsubstituted C 1-60 haloalkoxy, a tri(C 1-60 alkyl)silyl, a substituted or unsubstituted C 6-60 aryl, a tri(C 6-60 aryl)silyl, a substituted or unsubstituted C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S, or are bonded to adjacent groups to form a substituted or unsubstituted condensed ring;
R′ 1 and R′ 2 are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1-60 alkyl, a substituted or unsubstituted C 1-60 alkoxy, a substituted or unsubstituted C 1-60 haloalkyl, a substituted or unsubstituted C 1-60 haloalkoxy, a tri(C 1-60 alkyl)silyl, or a substituted or unsubstituted C 6-60 aryl; and
m and n are each independently an integer of 0 to 3.

2. The compound according to claim 1 , wherein:
the compound of Chemical Formula 1 is any one of the compounds of the following Chemical Formulas 1-1 to 1-3:

wherein:
A 1 , A 2 , B 1 , B 2 , L 1 , L 2 , R′ 1 , R′ 2 , m and n are as defined for Chemical Formula 1 in claim 1 .

3. The compound according to claim 1 , wherein:
A 1 is a benzene ring, and A 2 is a naphthalene ring; or
A 1 is a naphthalene ring, and A 2 is a benzene ring; or
A 1 is a benzene ring, and A 2 is

 or
A 1 is

 and A 2 is a benzene ring; or
A 1 is a naphthalene ring, and A 2 is

 or
A 1 is

 and A 2 is a naphthalene ring; or
A 1 is a naphthalene ring, and A 2 is a naphthalene ring; or
A 1 is

 and A 2 is

where X is as defined in claim 1 .

4. The compound according to claim 1 , wherein:
the compound of Chemical Formula 1 is any one compound selected from the group consisting of the following compounds:

wherein:
X 1 and X 2 are each independently CR 1 R 2 , SiR 3 R 4 , NR 5 , O, S, or SO 2 ; and
Y, R 1 , R 2 , R 3 , R 4 , R 5 , B 1 , B 2 , R′ 1 , R′ 2 m and n are as defined in claim 1 .

5. The compound according to claim 1 , wherein:
each X is independently CR 1 R 2 , O, or S,
where R 1 and R 2 are each independently methyl or ethyl.

6. The compound according to claim 1 , wherein:
L 1 and L 2 are each independently a direct bond or phenylene.

7. The compound according to claim 1 , wherein:
R 6 and R 7 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, cyclohexenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, benzonaphthofuranyl, benzonaphthothiophenyl, or benzodimethylfluorenyl, or are bonded to adjacent substituents to form a substituted or unsubstituted condensed ring, and
they are each unsubstituted or independently substituted with deuterium, *—CD 3 , C 1-4 alkyl, *—(C 1-4 alkyl)phenyl, C 3-10 cycloalkyl, phenyl, halogen, cyano, or *—SiR 11 R 12 R 13 , where R 11 , R 12 and R 13 are each independently methyl, ethyl, tertbutyl or phenyl, and *— means a bond linked to another substituent group.

8. The compound according to claim 1 , wherein:
B 1 and B 2 are each independently any one selected from the group consisting of the following:

Assignees

• Lg Chemical Ltd

Inventors

• Yoon Jung Min
• Kim Kongkyeom
• Koo Ki Dong
• Kim Young Seok
• Oh Joongsuk
• Lee Min Woo

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title