IP Library Granted Patent US 9,722,182
Granted Patent B2
US 9,722,182 · App. 13/939,342 · Granted Aug 1, 2017

Heterocyclic compound and organic light-emitting device including the same

Inventors: Sun-Young Lee (Yongin, KR); Yoon-Hyun Kwak (Yongin, KR); Bum-Woo Park (Yongin, KR); Jong-Won Choi (Yongin, KR); Wha-Il Choi (Yongin, KR); So-Yeon Kim (Yongin, KR); Ji-Youn Lee (Yongin, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0052C07D209/80C07D403/14C07D405/04C07D491/048C09K11/06H01L51/0059H01L51/0061H01L51/0065H01L51/0071H01L51/0072H01L51/0073H01L51/0074H01L51/006H01L51/0055H01L51/0081H01L51/0085H01L51/0087H01L51/0088H01L51/5016H01L51/5056
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Quick Facts
Patent No.
US 9,722,182
App. No.
13/939,342
Granted
Aug 1, 2017
Kind
B2
Abstract

A heterocyclic compound represented by Formula 1 below, and an organic light-emitting device including the heterocyclic compound:

Claims (67)

1. A heterocyclic compound represented by Formula 1 below:

wherein, in Formula 1,

R 1 to R 10 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, an amino group substituted with one or two C6-C60 aryl groups, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group;

R 8 and R 9 are linked to each other to form a benzene ring, a naphthalene ring, or a dibenzofuran ring, or R 6 and R 7 are linked to each other to form a benzene ring, a naphthalene ring, or a dibenzofuran ring; and

X is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C4-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group.

2. The heterocyclic compound as claimed in claim 1 , wherein the heterocyclic compound is represented by Formula 2 below:

wherein, in Formula 2,

R 1 to R 7 , R 10 , and R 50 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, an amino group substituted with one or two C6-C60 aryl groups, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group;

n is an integer from 1 to 4;

when n>1, a plurality of (R 50 ) n moieties are optionally linked to each other to form a ring; and

X is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C4-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group.

3. The heterocyclic compound as claimed in claim 1 , wherein R 7 in Formula 2 is a group represented by one of Formulae 2a to 2d below:

wherein, in Formulae 2a to 2d,

Q 1 is a linker represented by —C(R 30 )(R 31 )—, —O—, —S—, or —N(R 32 )—;

Z 1 , R 30 , R 31 , and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, an amino group substituted with one or two C6-C20 aryl groups, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer from 1 to 7; and

* indicates a binding site of R 7 in Formula 2.

4. The heterocyclic compound as claimed in claim 2 , wherein X in Formula 2 is a group represented by one of Formulae 3a to 3c below:

wherein, in Formulae 3a to 3c,

Z 1 and Z 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;

Y 1 to Y 3 are each independently C or N;

p is an integer from 1 to 5; and

* indicates a binding site of X in Formula 2.

5. The heterocyclic compound as claimed in claim 1 , wherein the heterocyclic compound is represented by Formula 3 below:

wherein, in Formula 3,

R 1 to R 5 , R 8 to R 10 , and R 60 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, an amino group substituted with one or two C6-C60 aryl groups, a substituted or unsubstituted C3-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group;

m is an integer from 1 to 4;

when m>1, a plurality of (R 60 ) m moieties are optionally linked together to form a ring; and

X is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C4-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group.

6. The heterocyclic compound as claimed in claim 5 , wherein R 8 in Formula 3 is a group represented by one of Formulae 2a to 2d below:

wherein, in Formulae 2a to 2d,

Q 1 is a linker represented by —C(R 30 )(R 31 )—, —O—, —S—, or —N(R 32 )—;

Z 1 , R 30 , R 31 , and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, an amino group substituted with one or two C6-C20 aryl groups, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer from 1 to 7; and

* indicates a binding site of R 8 in Formula 3.

7. The heterocyclic compound as claimed in claim 5 , wherein X in Formula 3 is a group represented by one of Formulae 3a to 3c:

wherein, in Formulae 3a to 3c,

Z 1 and Z 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxyl group, or a carboxy group;

Y 1 to Y 3 are each independently C or N;

p is an integer from 1 to 5; and

* indicates a binding site of X in Formula 3.

8. The heterocyclic compound as claimed in claim 1 , wherein the compound of Formula 1 is one of the compounds below:

9. An organic light-emitting device, comprising:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode, wherein the organic layer includes the heterocyclic compound as claimed in claim 1 .

10. The organic light-emitting device as claimed in claim 9 , wherein the organic layer includes an emission layer, and the heterocyclic compound is included as a host or a dopant for a fluorescent or phosphorescent device.

11. The organic light-emitting device as claimed in claim 9 , wherein the organic layer is a hole injection layer, a hole transport layer, or a functional layer having both hole injection and hole transport capabilities.

12. The organic light-emitting device as claimed in claim 9 , wherein the organic light-emitting device includes:

an emission layer,

an electron injection layer, an electron transport layer, or a functional layer having both electron injection and transport capabilities, and

a hole injection layer, a hole transport layer, or a functional layer having both hole injection and transport capabilities,

wherein the emission layer includes the heterocyclic compound; and

wherein the emission layer further includes an anthracene-based compound, an arylamine-based compound, or a styryl-based compound.

13. The organic light-emitting device as claimed in claim 9 , wherein the organic light-emitting device includes:

an emission layer,

an electron injection layer, an electron transport layer, or a functional layer having both electron injection and transport capabilities, and

a hole injection layer, a hole transport layer, or a functional layer having both hole injection and transport capabilities;

at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capabilities includes the heterocyclic compound; and

the emission layer includes at least one of a red, green, blue, or white emission layer, one of which includes a phosphorescent compound.

14. The organic light-emitting device as claimed in claim 13 , wherein the at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capabilities further includes a charge-generating material.

15. The organic light-emitting device as claimed in claim 14 , wherein the charge-generating material is a p-dopant.

16. The organic light-emitting device as claimed in claim 15 , wherein the p-dopant is a quinine derivative, a metal oxide, or a cyano group-containing compound.

17. The organic light-emitting device as claimed in claim 9 , wherein the organic layer includes an electron transport layer, and the electron transport layer includes a metal complex.

18. The organic light-emitting device as claimed in claim 17 , wherein the metal complex is a Li complex.

19. The organic light-emitting device as claimed in claim 9 , wherein the organic layer is formed from the heterocyclic compound using a wet process.

20. A flat panel display device comprising the organic light-emitting device as claimed in claim 9 , wherein the first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin-film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2013
From: LEE, SUN-YOUNG; KWAK, YOON-HYUN; PARK, BUM-WOO; CHOI, JONG-WON; CHOI, WHA-IL; KIM, SO-YEON; LEE, JI-YOUN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 030775/0980 →
Priority Claims (1)
KR 10-2012-0121523 · Oct 30, 2012 · national
Continuity (1)
Related Publication 20140117326A1 · May 1, 2014