IP Library › Granted Patent US 10,230,056
Granted Patent B2
US 10,230,056 · App. 15/556,192 · Granted Mar 12, 2019

Heterocyclic compound and organic light emitting element comprising same

Inventors: Yongbum Cha (Daejeon, KR); Seongmi Cho (Daejeon, KR); Jin Joo Kim (Daejeon, KR)
Assignee: LG Chem, Ltd.
H01L51/0072C07D491/048C09K11/02C09K11/06H01L51/006H01L51/0052H01L51/0061H01L51/0067H01L51/0071H01L51/0073H01L51/0074H01L51/0077H01L51/0085H01L51/50C09K2211/1011C09K2211/1018H01L51/0054H01L51/5012H01L51/5016H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096
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Quick Facts
Patent No.
US 10,230,056
App. No.
15/556,192
Granted
Mar 12, 2019
Kind
B2
Abstract

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

Claims (59)

1. A compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,

Ar 1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted multicyclic aryl group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted heterocyclic group;

L 1 and L 2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;

p and q are the same as or different from each other, and each independently an integer of 0 to 5;

when p and q are 2 or greater, structures in the parentheses are the same as or different from each other; and

Ar 2 and R 1 to R 8 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aralkyl group; a substituted or unsubstituted aralkenyl group; a substituted or unsubstituted alkylaryl group; a substituted or unsubstituted aralkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups bond to each other to form a substituted or unsubstituted ring.

2. The compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 2 or Chemical Formula 3:

wherein, in Chemical Formula 2 and Chemical Formula 3,

definitions of p, q, L 1 , L 2 , Ar 1 , Ar 2 and R 1 to R 8 are the same as in Chemical Formula 1.

3. The compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following Chemical Formula 4 to Chemical Formula 9:

wherein, in Chemical Formula 4 to Chemical Formula 9,

definitions of q, L 2 , Ar 1 , Ar 2 and R 1 to R 8 are the same as in Chemical Formula 1;

m1 to m3 are each independently an integer of 0 to 4;

when m1 to m3 are 2 or greater, structures in the parentheses are the same as or different from each other; and

R 101 to R 103 are the same as or different from each other, and each independently have the same definitions as R 1 to R 8 in Chemical Formula 1.

4. The compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 10 or Chemical Formula 11:

wherein, in Chemical Formula 10 and Chemical Formula 11,

definitions of p, q, L 1 , L 2 , Ar 1 , Ar 2 and R 1 to R 8 are the same as in Chemical Formula 1; and

R 11 to R 14 are the same as or different from each other, and each independently have the same definitions as R 1 to R 8 .

5. The compound of claim 1 , wherein L 1 and L 2 are the same as or different from each other, and each independently one or more types selected from the group consisting of a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted quaterphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted pyrenylene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyridinylene group; a substituted or unsubstituted pyrimidinylene group; a substituted or unsubstituted triazinylene group; a substituted or unsubstituted quinolinylene group; a substituted or unsubstituted quinazolinylene group; a substituted or unsubstituted carbazolylene group; a substituted or unsubstituted dibenzofuranylene group; and a substituted or unsubstituted divalent dibenzothiophene group.

6. The compound of claim 1 , wherein L 1 and L 2 are the same as or different from each other, and each independently a direct bond or any one selected from among the following compounds:

wherein, the structures are unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amine group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylheteroarylamine group; an arylphosphine group; and a heterocyclic group.

7. The compound of claim 1 , wherein Ar 1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted multicyclic aryl group having 6 to 40 carbon atoms; an arylamine group having 6 to 40 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms; and

Ar 2 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

8. The compound of claim 1 , wherein -(L 1 )p-Ar 1 is any one selected from among the following structures:

9. The compound of claim 1 , wherein the compound of Chemical Formula 1 is any one selected from among the following structures:

10. An organic light emitting device comprising:

a first electrode;

a second electrode; and

one or more organic material layers disposed between the first electrode and the second electrode,

wherein one or more layers of the organic material layers include the compound of claim 1 .

11. The organic light emitting device of claim 10 , wherein the organic material layer includes one or more layers of an electron transfer layer; an electron injection layer; and a layer carrying out electron transfer and electron injection at the same time, and one or more layers of the layers include the compound.

12. The organic light emitting device of claim 10 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer.

13. The organic light emitting device of claim 10 , wherein the organic material layer includes one or more layers of a hole injection layer; a hole transfer layer; and a layer carrying out hole injection and hole transfer at the same time, and one or more layers of the layers include the compound.

14. The organic light emitting device of claim 10 , wherein the organic material layer includes one or more layers of a hole transfer layer; an electron blocking layer; and a hole transfer and electron blocking layer, and one or more layers of the layers include the compound.

15. The organic light emitting device of claim 10 , wherein the organic material layer includes the compound as a host, and includes other organic compounds, metals or metal compounds as a dopant.

16. The organic light emitting device of claim 10 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1-A:

wherein, in Chemical Formula 1-A,

r is an integer of 1 or greater, and when r is 2 or greater, structures in the parentheses are the same as or different from each other;

Ar 11 is a substituted or unsubstituted monovalent or higher benzofluorene group; a substituted or unsubstituted monovalent or higher fluoranthene group; a substituted or unsubstituted monovalent or higher pyrene group; or a substituted or unsubstituted monovalent or higher chrysene group;

L 11 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; and

R 21 and R 22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted arylalkyl group; or a substituted or unsubstituted heteroaryl group, or bond to each other to form a substituted or unsubstituted ring.

17. The organic light emitting device of claim 16 , wherein r is 2, Ar 11 is a divalent pyrene group, L 11 is a direct bond, R 21 and R 22 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkylgermanium group.

18. The organic light emitting device of claim 10 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1-B:

wherein, in Chemical Formula 1-B,

Ar 21 and Ar 22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;

L 21 and L 22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;

u and v are each independently an integer of 1 or 2, and when u and v are 2, substituents in the parentheses are the same as or different from each other;

R 23 and R 24 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and

t and s are each an integer of 0 to 4, and when t and s are 2 or greater, substituents in the parentheses are the same as or different from each other.

19. The organic light emitting device of claim 18 , wherein Ar 21 is a 2-naphthyl group, Ar 22 is a 1-naphthyl group, L 21 is a phenylene group, L 22 is a direct bond, u and v are each 1, and R 23 and R 24 are each hydrogen.

20. The organic light emitting device of claim 16 , wherein the light emitting layer includes a compound represented by the following Chemical Formula 1-B:

wherein, in Chemical Formula 1-B,

Ar 21 and Ar 22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;

L 21 and L 22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;

u and v are each independently an integer of 1 or 2, and when u and v are 2, substituents in the parentheses are the same as or different from each other;

R 23 and R 24 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and

t and s are each an integer of 0 to 4, and when t and s are 2 or greater, substituents in the parentheses are the same as or different from each other.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2017
From: CHA, YONGBUM; CHO, SEONGMI; KIM, JIN JOO
To: LG CHEM, LTD.
Reel/Frame 043523/0751 →
Priority Claims (1)
KR 10-2015-0121167 · Aug 27, 2015 · national
Continuity (1)
Related Publication 20180047914A1 · Feb 15, 2018
Cited By (1)
US 12,201,020