IP Library › Granted Patent US 9,666,809
Granted Patent B2
US 9,666,809 · App. 14/221,024 · Granted May 30, 2017

Compound and organic light-emitting device including the same

Inventor: Jung-Sub Lee (Yongin, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0058H01L51/0061H01L51/0067H01L51/0071H01L51/0072H01L51/0081H01L51/0085H01L51/0087H01L51/0088H01L51/5016
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Quick Facts
Patent No.
US 9,666,809
App. No.
14/221,024
Granted
May 30, 2017
Kind
B2
Abstract

An organic light-emitting device including a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode is provided.

Claims (80)

1. A compound represented by Formula 1:

wherein in Formula 1,

A is a fused C 2 -C 4 5-membered heteroaryl ring;

E and X 1 are each independently CH or N (nitrogen);

R 1 to R 3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an amino group, a nitro group, a nitryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 heteroaryl group, a substituted or unsubstituted C 1 to C 40 alkoxy group, a substituted or unsubstituted C 6 to C 40 aryloxy group, a C 1 to C 40 alkylamino group, a C 6 to C 40 arylamino group, a C 6 to C 40 diarylamino group, a C 1 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group, a C 6 to C 40 heteroarylalkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C 6 to C 40 arylsilyl group, or a C 1 to C 40 heteroarylsilyl group, or optionally R 1 and R 2 together with the atoms to which they are attached is a ring; and,

Ar 1 and Ar 2 are each independently a hydrogen, a deuterium, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 heteroaryl group, a substituted or unsubstituted C 1 to C 40 alkoxy group, a substituted or unsubstituted C 6 to C 40 aryloxy group, a C 1 to C 40 alkylamino group, a C 6 to C 40 arylamino group, a C 6 to C 40 diarylamino group, a C 1 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group, a C 6 to C 40 heteroarylalkyl group, a C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C 6 to C 40 arylsilyl group, or a C 1 to C 40 heteroarylsilyl group,

provided E and X 1 are not both CH.

2. The compound of claim 1 , wherein:

A is a thiophene moiety or an imidazole moiety.

3. The compound of claim 1 , wherein:

R 1 and R 2 together with the atoms to which they are attached is a ring; and the ring is a heteroaryl ring.

4. The compound of claim 1 , wherein:

the compound represented by Formula 1 is a compound represented by Formula 2:

in Formula 2,

X is S (sulfur) or NR 100 , and

R 4 , R 5 , and R 100 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an amino group, a nitro group, a nitryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 heteroaryl group, a substituted or unsubstituted C 1 to C 40 alkoxy group, a substituted or unsubstituted C 6 to C 40 aryloxy group, a C 1 to C 40 alkylamino group, a C 6 to C 40 arylamino group, a C 6 to C 40 diarylamino group, a C 1 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group, a C 6 to C 40 heteroarylalkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C 6 to C 40 arylsilyl group, or a C 1 to C 40 heteroarylsilyl group.

5. The compound of claim 1 , wherein:

the compound represented by Formula 1 is a compound represented by Formula 3:

in Formula 3,

X and Y are each independently S (sulfur), N (nitrogen), or NR 100 , and

R 4 , and R 100 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an amino group, a nitro group, a nitryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 heteroaryl group, a substituted or unsubstituted C 1 to C 40 alkoxy group, a substituted or unsubstituted C 6 to C 40 aryloxy group, a C 1 to C 40 alkylamino group, a C 6 to C 40 arylamino group, a C 6 to C 40 diarylamino group, a C 1 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group, a C 6 to C 40 heteroarylalkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C 6 to C 40 arylsilyl group, or a C 1 to C 40 heteroarylsilyl group.

6. The compound of claim 1 , wherein

the compound represented by Formula 1 is a compound represented by Formula 4:

in Formula 4,

X and Y are each independently S (sulfur) or NR 100 , and

R 4 to R 7 , and R 100 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an amino group, a nitro group, a nitryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 heteroaryl group, a substituted or unsubstituted C 1 to C 40 alkoxy group, a substituted or unsubstituted C 6 to C 40 aryloxy group, a C 1 to C 40 alkylamino group, a C 6 to C 40 arylamino group, a C 6 to C 40 diarylamino group, a C 1 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group, a C 6 to C 40 heteroarylalkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C 6 to C 40 arylsilyl group, or a C 1 to C 40 heteroarylsilyl group.

7. The compound of claim 1 , wherein

the compound represented by Formula 1 is a compound represented by Formula 5:

in Formula 5,

X and Y are each independently S (sulfur), N (nitrogen), or NR 100 , and

R 4 , R 5 , R 8 , and R 100 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an amino group, a nitro group, a nitryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 to C 40 alkynyl group, a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 heteroaryl group, a substituted or unsubstituted C 1 to C 40 alkoxy group, a substituted or unsubstituted C 6 to C 40 aryloxy group, a C 1 to C 40 alkylamino group, a C 6 to C 40 arylamino group, a C 6 to C 40 diarylamino group, a C 1 to C 40 heteroarylamino group, a C 2 to C 40 diheteroarylamino group, a C 6 to C 40 arylalkyl group, a C 6 to C 40 heteroarylalkyl group, a substituted or unsubstituted C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 3 to C 40 alkylsilyl group, a C 6 to C 40 arylsilyl group, or a C 1 to C 40 heteroarylsilyl group.

8. The compound of claim 1 , wherein:

Ar 2 and R 3 is a hydrogen or a deuterium.

9. The compound of claim 4 , wherein:

R 4 and R 5 in Formula 2 are each independently one of Formulae 2a to 2e:

wherein in Formulae 2a to 2e,

Q 1 is S (sulfur), CR 51 R 52 , or NR 53 ,

Y 1 to Y 3 are each independently CH or N (nitrogen),

Z 1 , Z 2 , R 51 , R 52 , and R 53 are each independently a hydrogen, a deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 1 to C 20 heteroaryl group, a substituted or unsubstituted C 6 to C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer of 1 to 8; and

* indicates an attachment position.

10. The compound of claim 4 , wherein:

R 1 and R 2 in Formula 2 is a hydrogen or a deuterium.

11. The compound of claim 5 , wherein:

R 4 in Formula 3 is represented by Formula 3a:

wherein in Formula 3a,

Z 1 is a hydrogen, a deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 1 to C 20 heteroaryl group, a substituted or unsubstituted C 6 to C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer of 1 to 5; and

* indicates an attachment position.

12. The compound of claim 5 , wherein:

R 100 in Formula 3 is one of Formulae 4a to 4c:

wherein in Formulae 4a to 4c,

Q 2 is S (sulfur), CR 51 R 52 , or NR 53 ,

Z 1 , R 51 , R 52 , and R 53 are each independently a hydrogen, a deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 1 to C 20 heteroaryl group, a substituted or unsubstituted C 6 to C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer of 1 to 7; and

* indicates an attachment position.

13. The compound of claim 5 , wherein:

R 1 and R 3 in Formula 3 is a hydrogen or a deuterium.

14. The compound of claim 6 , wherein:

R 5 , R 6 , and R 7 in Formula 4 are each independently one of Formulae 5a to 5c:

wherein in Formulae 5a to 5c,

Z 1 is a hydrogen, a deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 1 to C 20 heteroaryl group, a substituted or unsubstituted C 6 to C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer of 1 to 8; and

* indicates an attachment position.

15. The compound of claim 7 , wherein

R 4 , R 5 , R 8 , and R 100 in Formula 5 are each independently one of Formulae 6a to 6c:

wherein in Formulae 6a to 6c,

Z 1 is a hydrogen, a deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C 1 to C 20 heteroaryl group, a substituted or unsubstituted C 6 to C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, or a carboxy group;

p is an integer of 1 to 7; and

* indicates an attachment position.

16. The compound of claim 1 , wherein:

the compound of Formula 1 is any one of compounds below:

17. 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 the compound of claim 1 .

18. The organic light-emitting device of claim 17 , wherein

the organic layer is an emission layer.

19. A flat display apparatus comprising the organic light-emitting device of claim 17 , 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 Mar 21, 2014
From: LEE, JUNG-SUB
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 032497/0034 →
Priority Claims (1)
KR 10-2013-0149498 · Dec 3, 2013 · national
Continuity (1)
Related Publication 20150155497A1 · Jun 4, 2015