IP Library Granted Patent US 9,028,978
Granted Patent B2
US 9,028,978 · App. 13/309,650 · Granted May 12, 2015

Compound and organic light-emitting device including the same

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Quick Facts
Patent No.
US 9,028,978
App. No.
13/309,650
Granted
May 12, 2015
Kind
B2
Abstract

A compound represented by Formula 1 below and an organic light-emitting device including an organic layer containing the compound of Formula 1: wherein R 1 to R 4 , X and Y, a and b, and m and n are defined as in the specification.

Claims (42)

1. A compound represented by Formula 1 below:

X and Y in Formula 1 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 4 -C 60 heteroarylene group, a substituted or unsubstituted C 5 -C 60 cycloalkylene group, and a substituted or unsubstituted C 5 -C 60 heterocycloalkylene group;

R 1 to R 4 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 4 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group;

adjacent R 1 and R 2 or R 3 and R 4 are optionally linked together to form a saturated or unsaturated carbon ring;

m and n are each independently an integer from 0 to 2; and

a and b are each independently an integer from 0 to 2 with a proviso that both a and b are not zero at the same time.

2. The compound of claim 1 , X and Y in Formula 1 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 4 -C 20 heteroarylene group, a substituted or unsubstituted C 5 -C 20 cycloalkylene group, and a substituted or unsubstituted C 5 -C 20 heterocycloalkylene group; and

R 1 to R 4 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted C 4 -C 40 heteroaryl group, and a substituted or unsubstituted C 6 -C 40 condensed polycyclic group.

3. The compound of claim 1 , wherein X and Y in Formula 1 are each independently selected from groups represented by Formulae 2a to 2d below:

wherein in Formulae 2a to 3d, * indicates a binding site.

4. The compound of claim 1 , R 1 to R 4 in Formula 1 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a C 1 -C 20 alkyl group, and groups represented by Formulae 3a to 3e below:

Q 1 in Formulae 3a to 3e is a linking group represented by —C(R 5 )(R 6 )—, —N(R 7 )—, —S—, or —O—;

Z 1 , R 5 , R 6 , and R 7 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 4 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group;

p is an integer from 1 to 5;

q is an integer from 1 to 7;

r is an integer from 1 to 9; and

* indicates a binding site.

5. The compound of claim 1 , wherein the compound of Formula 1 comprises one of the compounds below:

6. 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 a first layer including the compound of Formula 1 of claim 1 .

7. The organic light-emitting device of claim 6 , wherein the first layer comprises an emission layer.

8. The organic light-emitting device of claim 6 , wherein the first layer comprises an emission layer, and the compound of Formula 1 is used as a dopant.

9. The organic light-emitting device of claim 6 , the first layer comprising an emission layer comprised of the compound of Formula 1 as a dopant and a compound represented by Formula 2 as a host:

R 1 to R 14 in Formula 2 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 3 -C 60 cycloalkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 4 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group; and

R 8 and R 9 are optionally linked together to form a saturated or unsaturated carbon ring.

10. The organic light-emitting device of claim 9 , R 1 to R 14 in Formula 2 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 40 aryl group, a substituted or unsubstituted C 4 -C 40 heteroaryl group, and a substituted or unsubstituted C 6 -C 40 condensed polycyclic group.

11. The organic light-emitting device of claim 9 , R 1 to R 14 in Formula 2 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a C 1 -C 20 alkyl group, and groups represented by Formulae 4a to 4e below:

Z 1 in Formulae 4a to 4e is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 4 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, and a carboxyl group;

s is an integer from 1 to 5;

t is an integer from 1 to 7;

u is an integer from 1 to 9; and

* indicates a binding site.

12. The organic light-emitting device of claim 9 , wherein the compound of Formula 2 comprises one of the compounds below:

13. The organic light-emitting device of claim 9 , wherein the emission layer comprises a blue emission layer, the compound of Formula 1 is used as a blue dopant, and the compound of Formula 2 is used as a blue host.

14. The organic light-emitting device of claim 6 , wherein the first layer comprises an emission layer, and a red layer, a green layer, a blue layer, or a white layer of the emission layer contains a phosphorescent compound.

15. The organic light-emitting device of claim 6 , wherein the organic layer further comprises a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport capabilities, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination of at least two thereof.

16. The organic light-emitting device of claim 15 , wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having hole injection and hole transport capabilities further comprises a charge generating material.

17. The organic light-emitting device of claim 15 , wherein the electron transport layer comprises an electron transporting organic material and a metal-containing material.

18. The organic light-emitting device of claim 17 , wherein the metal-containing material comprises a lithium (Li) complex.

Assignments (2)
MERGER Recorded Sep 21, 2012
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 029241/0599 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2012
From: KIM, MYEONG-SUK; SHIN, DONG-WOO; BAE, SUNG-SOO; SHIM, JI-HYE; SHIN, DAE-YUP; CHOI, BYOUNG-KI
To: SAMSUNG MOBILE DISPLAY CO., LTD., A CORPORATION CHARTERED IN AND EXISTING UNDER THE LAWS OF THE REPUBLIC OF KOREA
Reel/Frame 027638/0269 →