IP Library Granted Patent US 11,453,650
Granted Patent B2
US 11,453,650 · App. 16/609,199 · Granted Sep 27, 2022

Heterocyclic compound and organic light emitting device comprising the same

Inventors: Junghoon Yang (Daejeon, KR); Dong Hoon Lee (Daejeon, KR); Jung Oh Huh (Daejeon, KR); Boon Jae Jang (Daejeon, KR); Dong Uk Heo (Daejeon, KR); Mi Yeon Han (Daejeon, KR); Min Woo Jung (Daejeon, KR)
Assignee: LG CHEM, LTD.
C07D251/24C07D213/16C07D239/26C07D239/74C07D401/14C07D487/04H01L51/0067H01L51/0072
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Quick Facts
Patent No.
US 11,453,650
App. No.
16/609,199
Granted
Sep 27, 2022
Kind
B2
Abstract

Provided is a heterocyclic compound of Chemical Formula 1: where L 1 is a single bond or a substituted or unsubstituted C 6-60 arylene; L 2 is a single bond, a substituted or unsubstituted C 6-60 arylene, or a substituted or unsubstituted C 5-60 heteroarylene, and Ar 1 is one of the following Chemical Formulas 2, 3, 4, or 5: and an organic light emitting device including the same.

Claims (40)

1. A binaphthalene compound of Chemical Formula 1:

wherein, in Chemical Formula 1:

L 1 is a single bond, or a substituted or unsubstituted C 6-60 arylene;

L 2 is a single bond or a substituted or unsubstituted C 6-60 arylene; and

Ar 1 is one of the following Chemical Formula 2, 3, 4, or 5,

wherein, in Chemical Formulas 2 to 5:

X 1 , X 2 , and X 3 are each independently N or CR 4 , where there is at least one N;

X 4 and X 5 are each independently N or CR 5 , where there is at least one N;

R 1 , R 2 , and R 3 are each independently a substituted or unsubstituted C 1-40 alkyl, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 5-60 heteroaryl, or R 1 , R 2 , and R 3 are each independently one in which a hydrogen atom of the alkyl, the aryl, or the heteroaryl is substituted with deuterium or CN; and

R 4 and R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1-40 alkyl, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 5-60 heteroaryl.

2. The compound according to claim 1 , wherein the compound of Chemical Formula 1 is one of the following Chemical Formula 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, or 1-7:

wherein, in Chemical Formulas 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, and 1-7:

L 1 is a single bond, or a substituted or unsubstituted C 6-60 arylene;

L 2 is a single bond, a substituted or unsubstituted C 6-60 arylene, or a substituted or unsubstituted C 5-60 heteroarylene; and

R 1 , R 2 , and R 3 are each independently a substituted or unsubstituted C 1-40 alkyl, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 5-60 heteroaryl, or R 1 , R 2 , and R 3 are each independently one in which a hydrogen atom of the alkyl, the aryl, or the heteroaryl is substituted with deuterium or CN.

3. A binaphthalene compound of Chemical Formula 1:

wherein, in Chemical Formula 1:

L 1 and L 2 are a bond, phenylene, or biphenylene; and

Ar 1 is one of the following Chemical Formula 2, 3, 4, or 5,

wherein, in Chemical Formulas 2 to 5:

X 1 , X 2 , and X 3 are each independently N or CR 4 , where there is at least one N;

X 4 and X 5 are each independently N or CR 5 , where there is at least one N;

R 1 , R 2 , and R 3 are each independently a substituted or unsubstituted C 1-40 alkyl, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 5-60 heteroaryl, or R 1 , R 2 , and R 3 are each independently one in which a hydrogen atom of the alkyl, the aryl, or the heteroaryl is substituted with deuterium or CN; and

R 4 and R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1-40 alkyl, a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 5-60 heteroaryl.

4. The compound according to claim 1 , wherein X 1 , X 2 , X 3 , X 4 , and X 5 are N.

5. A binaphthalene compound of Chemical Formula 1:

wherein, in Chemical Formula 1:

L 1 and L 2 are a bond, phenylene, or biphenylene; and

Ar 1 is one of the following Chemical Formula 2, 3, 4, or 5,

wherein, in Chemical Formulas 2 to 5:

X 1 , X 2 , and X 3 are each independently N or CR 4 , where there is at least one N;

X 4 and X 5 are each independently N or CR 5 , where there is at least one N; and

R 1 , R 2 , R 3 , R 4 , and R 5 are hydrogen, phenyl, or pyridinyl.

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

7. An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more one layers of the organic material layers comprise the compound according to claim 1 .

8. An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more one layers of the organic material layers comprise the compound according to claim 2 .

9. An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more one layers of the organic material layers comprise the compound according to claim 3 .

10. An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more one layers of the organic material layers comprise the compound according to claim 4 .

11. An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more one layers of the organic material layers comprise the compound according to claim 5 .

12. An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more one layers of the organic material layers comprise the compound according to claim 6 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 20, 2019
From: YANG, JUNGHOON; LEE, DONG HOON; JANG, BOON JAE; HEO, DONG UK; HAN, MI YEON; JUNG, MIN WOO; HUH, JUNG OH
To: LG CHEM, LTD.
Reel/Frame 051071/0597 →
Priority Claims (2)
KR 10-2017-0067648 · May 31, 2017 · national
KR 10-2018-0062154 · May 30, 2018 · national
Continuity (1)
Related Publication 20200181096A1 · Jun 11, 2020