IP Library Granted Patent US 8,384,074
Granted Patent B2
US 8,384,074 · App. 13/078,080 · Granted Feb 26, 2013

Heterocyclic compound and organic light-emitting device including the same

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Quick Facts
Patent No.
US 8,384,074
App. No.
13/078,080
Granted
Feb 26, 2013
Kind
B2
Abstract

A heterocyclic compound of formula 1 and an organic light-emitting device including an organic layer containing the heterocyclic compound. The heterocyclic compound of Formula 1 may be suitable as a material for an emission layer, an electron transport layer or an electron injection layer of an organic light-emitting device. Due to the inclusion of the heterocylic group in its molecular structure, the heterocyclic compound of Formula 1 may have a high glass transition temperature (Tg) or a high melting point, and may prevent crystallization. An organic light-emitting device manufactured using the heterocyclic compound of Formula 1, in which a chrysene group and an indole group are fused, has excellent durability when stored or operated.

Claims (44)

1. A heterocyclic compound represented by Formula 1 below:

Formula 1

wherein R 1 through R 13 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an amino group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 2 -C 50 alkenyl group, a substituted or unsubstituted C 2 -C 50 alkynyl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 1 -C 50 alkoxy group, a group represented by —(Ar 1 ) a —(Ar 11 ), and a group represented by —N[—(Ar 2 ) b —(Ar 12 )][—(Ar 3 ) c —(Ar 13 )], wherein at least two adjacent groups of R 1 through R 13 are linked to form a saturated or unsaturated ring;

Ar 1 through Ar 3 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene group, a substituted or unsubstituted C 2 -C 50 alkenylene group, a substituted or unsubstituted C 5 -C 60 arylene group, and a substituted or unsubstituted C 4 -C 60 heteroarylene group;

Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 60 aryl group, a substituted or unsubstituted C 5 -C 50 aryloxy group, a substituted or unsubstituted C 5 -C 50 arylthio group, and a substituted or unsubstituted C 4 -C 60 heteroaryl group;

a, b and c are each independently an integer from 0 to 10; and

—(Ar 1 ) a — groups in —(Ar 1 ) a —(Ar 11 ) are identical to or different from each other, —(Ar 2 ) b — groups in —N[—(Ar 2 ) b —(Ar 12 )][—(Ar 3 ) c —(Ar 13 )] are identical to or different from each other, and —(Ar 3 ) c — groups are identical to or different from each other.

2. A heterocyclic compound of claim 1 , wherein Ar 1 through Ar 3 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 20 arylene group and a substituted or unsubstituted C 4 -C 20 heteroarylene group.

3. A heterocyclic compound of claim 1 , wherein Ar 1 through Ar 3 are each independently selected from the group consisting of a phenylene group, a C 1 -C 10 alkyl phenylene group, a di(C 1 -C 10 alkyl) phenylene group, a naphthylene group, a C 1 -C 10 alkyl naphthylene group, a di(C 1 -C 10 alkyl) naphthylene group, an anthrylene group, a C 1 -C 10 alkyl anthrylene group, a di(C 1 -C 10 alkyl) anthrylene group, a fluorenylene group, a C 1 -C 10 alkyl fluorenylene group, a di(C 1 -C 10 alkyl) fluorenylene group, a C 6 -C 14 aryl fluorenylene group, a di(C 6 -C 14 aryl) fluorenylene group, a pyridylene group, a C 1 -C 10 alkyl pyridylene group, a di(C 1 -C 10 alkyl) pyridylene group, a carbazolylene group, a C 1 -C 10 alkyl carbazolylene group, and a di(C 1 -C 10 alkyl) carbazolylene group.

4. A heterocyclic compound of claim 1 , wherein Ar 1 through Ar 3 are each independently selected from the groups represented by Formulae 2A through 2G below:

wherein Z 1 , Z 2 , Z 11 and Z 12 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 14 aryl group; p is an integer from 1 to 8; * denotes a binding site with Ar 11 , Ar 12 or Ar 13 ; and *′ denotes a binding site with a ring of Formula 1, wherein at least two adjacent groups of Z 1 , Z 2 , Z 11 and Z 12 may be linked to form a saturated or unsaturated ring.

5. A heterocyclic compound of claim 1 , wherein Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 20 aryl group and a substituted or unsubstituted C 4 -C 20 heteroaryl group.

6. A heterocyclic compound of claim 1 , wherein Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a phenyl group, a C 1 -C 10 alkyl phenyl group, a di(C 1 -C 10 alkyl)phenyl group, a C 6 -C 14 aryl phenyl group, a di(C 6 -C 14 aryl)phenyl group, a naphthyl group, a C 1 -C 10 alkyl naphthyl group, a di(C 1 -C 10 alkyl)naphthyl group, a C 6 -C 14 aryl naphthyl group, a di(C 6 -C 14 aryl)naphthyl group, an anthryl group, a C 1 -C 10 alkyl anthryl group, a di(C 1 -C 10 alkyl)anthryl group, a C 6 -C 14 aryl anthryl group, a di(C 6 -C 14 aryl)anthryl group, a phenanthryl group, a C 1 -C 10 alkyl phenanthryl group, a di(C 1 -C 10 alkyl)phenanthryl group, a C 6 -C 14 aryl phenanthryl group, a di(C 6 -C 14 aryl)phenanthryl group, a fluorenyl group, a C 1 -C 10 alkyl fluorenyl group, a di(C 1 -C 10 alkyl)fluorenyl group, a C 6 -C 14 aryl fluorenyl group, a di(C 6 -C 14 aryl) fluorenyl group, a pyridyl group, a C 1 -C 10 alkyl pyridyl group, a di(C 1 -C 10 alkyl)pyridyl group, a pyrenyl group, a C 1 -C 10 alkyl pyrenyl group, a di(C 1 -C 10 alkyl)pyrenyl group, a C 6 -C 14 aryl pyrenyl group, a di(C 6 -C 14 aryl)pyrenyl group, a phenanthrolinyl group, a C 1 -C 10 alkyl phenanthrolinyl group, a di(C 1 -C 10 alkyl)phenanthiolinyl group, a C 6 -C 14 aryl phenanthrolinyl group, a di(C 6 -C 14 aryl)phenanthrolinyl group, a quinolinyl group, C 1 -C 10 alkyl quinolinyl group, a di(C 1 -C 10 alkyl)quinolinyl group, a C 6 -C 14 aryl quinolinyl group, a di(C 6 -C 14 aryl)quinolinyl group, a benzoxazolyl group, a C 1 -C 10 alkyl benzoxazolyl group, a di(C 1 -C 10 alkyl)benzoxazolyl group, a C 6 -C 14 aryl benzoxazolyl group, a di(C 6 -C 14 aryl)benzoxazolyl group, a benzothiazolyl group, a C 1 -C 10 alkyl benzothiazolyl group, a di(C 1 -C 10 alkyl)benzothiazolyl group, a C 6 -C 14 aryl benzothiazolyl group, a di(C 6 -C 14 aryl)benzothiazolyl group, a benzimidazolyl group, a C 1 -C 10 alkyl benzimidazolyl group, a di(C 1 -C 10 alkyl)benzimidazolyl group, a C 6 -C 14 aryl benzimidazolyl group, a di(C 6 -C 14 aryl)benzimidazolyl group, an imidazolpyridinyl group, a C 1 -C 10 alkyl imidazolpyridinyl group, a di(C 1 -C 10 alkyl) imidazolpyridinyl group, a C 6 -C 14 aryl imidazolpyridinyl group, a di(C 6 -C 14 aryl)imidazolpyridinyl group, an imidazolpyrimidinyl group, a C 1 -C 10 alkyl imidazolpyrimidinyl group, a di(C 1 -C 10 alkyl)imidazolpyrimidinyl group, a C 6 -C 14 aryl imidazolpyrimidinyl group, a di(C 6 -C 14 aryl)imidazolpyrimidinyl group, a carbazolyl group, a C 1 -C 10 alkyl carbazolyl group, a di(C 1 -C 10 alkyl)carbazolyl group, a C 6 -C 14 aryl carbazolyl group, and a di(C 6 -C 14 aryl)carbazolyl group.

7. A heterocyclic compound of claim 1 , wherein Ar 11 , Ar 12 , and Ar 13 are each independently selected from among the groups represented by Formulae 3A through 3O below:

wherein Z 1 , Z 2 , Z 3 , Z 11 and Z 12 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 14 aryl group; p is an integer from 1 to 8; and * denotes a binding site with Ar 11 , Ar 12 or Ar 13 , wherein at least two adjacent groups of Z 1 , Z 2 , Z 3 , Z 11 and Z 12 may be linked to form a saturated or unsaturated ring.

8. A heterocyclic compound of claim 1 , wherein a, b, and c are each independently 0, 1, 2 or 3.

9. A heterocyclic compound of claim 1 , wherein R 1 through R 13 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an amino group, a nitro group, a hydroxyl group, a substituted or unsubstituted C 1 -C 10 alkyl group, a group represented by —(Ar 1 ) a —(Ar 11 ), and a group represented by —N[—(Ar 2 ) b —(Ar 12 )][—(Ar 3 ) c —(Ar 13 )];

Ar 1 through Ar 3 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 20 arylene group and a substituted or unsubstituted C 4 - C 20 heteroarylene group;

Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a phenyl group, a C 1 -C 10 alkyl phenyl group, a di(C 1 -C 10 alkyl)phenyl group, a C 6 -C 14 aryl phenyl group, a di(C 6 -C 14 aryl)phenyl group, a naphthyl group, a C 1 -C 10 alkyl naphthyl group, a di(C 1 -C 10 alkyl)naphthyl group, a C 6 -C 14 aryl naphthyl group, a di(C 6 -C 14 aryl)naphthyl group, an anthryl group, a C 1 -C 10 alkyl anthryl group, a di(C 1 -C 10 alkyl)anthryl group, a C 6 -C 14 aryl anthryl group, a di(C 6 -C 14 aryl)anthryl group, a phenanthryl group, a C 1 -C 10 alkyl phenanthryl group, a di(C 1 -C 10 alkyl)phenanthryl group, a C 6 -C 14 aryl phenanthryl group, a di(C 6 -C 14 aryl)phenanthryl group, a fluorenyl group, a C 1 -C 10 alkyl fluorenyl group, a di(C 1 -C 10 alkyl)fluorenyl group, a C 6 -C 14 aryl fluorenyl group, a di(C 6 -C 14 aryl) fluorenyl group, a pyridyl group, a C 1 -C 10 alkyl pyridyl group, a di(C 1 -C 10 alkyl)pyridyl group, a pyrenyl group, a C 1 -C 10 alkyl pyrenyl group, a di(C 1 -C 10 alkyl)pyrenyl group, a C 6 -C 14 aryl pyrenyl group, a di(C 6 -C 14 aryl)pyrenyl group, a phenanthrolinyl group, a C 1 -C 10 alkyl phenanthrolinyl group, a di(C 1 -C 10 alkyl)phenanthrolinyl group, a C 6 -C 14 aryl phenanthrolinyl group, a di(C 6 -C 14 aryl)phenanthrolinyl group, a quinolinyl group, a C 1 -C 10 alkyl quinolinyl group, a di(C 1 -C 10 alkyl)quinolinyl group, a C 6 -C 14 aryl quinolinyl group, a di(C 6 -C 14 aryl)quinolinyl group, a benzoxazolyl group, a C 1 -C 10 alkyl benzoxazolyl group, a di(C 1 -C 10 alkyl)benzoxazolyl group, a C 6 -C 14 aryl benzoxazolyl group, a di(C 6 -C 14 aryl)benzoxazolyl group, a benzothiazolyl group, a C 1 -C 10 alkyl benzothiazolyl group, a di(C 1 -C 10 alkyl)benzothiazolyl group, a C 6 -C 14 aryl benzothiazolyl group, a di(C 6 -C 14 aryl)benzothiazolyl group, a benzimidazolyl group, a C 1 -C 10 alkyl benzimidazolyl group, a di(C 1 -C 10 alkyl)benzimidazolyl group, a C 6 -C 14 aryl benzimidazolyl group, a di(C 6 -C 14 aryl)benzimidazolyl group, an imidazolpyridinyl group, a C 1 -C 10 alkyl imidazolpyridinyl group, a di(C 1 -C 10 alkyl) imidazolpyridinyl group, a C 6 -C 14 aryl imidazolpyridinyl group, a di(C 6 -C 14 aryl)imidazolpyridinyl group, an imidazolpyrimidinyl group, a C 1 -C 10 alkyl imidazolpyrimidinyl group, a di(C 1 -C 10 alkyl)imidazolpyrimidinyl group, a C 6 -C 14 aryl imidazolpyrimidinyl group, a di(C 6 -C 14 aryl)imidazolpyrimidinyl group, a carbazolyl group, a C 1 -C 10 alkyl carbazolyl group, a di(C 1 -C 10 alkyl)carbazolyl group, a C 6 -C 14 aryl carbazolyl group, and a di(C 6 -C 14 aryl)carbazolyl group; and

a, b, and c are each independently 0, 1, 2 or 3.

10. A heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by Formula 2 below:

wherein, in Formula 2, R 1 , R 2 , R 3 and R 8 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 2 -C 50 alkenyl group, a substituted or unsubstituted C 2 -C 50 alkynyl group, a substituted or unsubstituted C 3 -C 50 cycloalkyl group, a substituted or unsubstituted C 1 -C 50 alkoxy group, a group represented by —(Ar 1 ) a —(Ar 11 ), and a group represented by —N[—(Ar 2 ) b —(Ar 12 )][—(Ar 3 ) c —(Ar 13 )], wherein at least two adjacent groups of R 1 through R 3 are linked to form a saturated or unsaturated ring;

Ar 1 through Ar 3 are each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene group, a substituted or unsubstituted C 2 -C 50 alkenylene group, a substituted or unsubstituted C 5 -C 60 arylene group, and a substituted or unsubstituted C 4 -C 60 heteroarylene group;

Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 60 aryl group, a substituted or unsubstituted C 5 -C 50 aryloxy group, a substituted or unsubstituted C 5 -C 50 arylthio group, and a substituted or unsubstituted C 4 -C 60 heteroaryl group;

a, b and c are each independently an integer from 0 to 10; and

—(Ar 1 ) a — groups in —(Ar 1 ) a —(Ar 11 ) are identical to or different from each other, —(Ar 2 ) b — groups in —N[—(Ar 2 ) b —(Ar 12 )][—(Ar 3 ) c —(Ar 13 )] are identical to or different from each other, and —(Ar 3 ) c — groups are identical to or different from each other.

11. A heterocyclic compound of claim 10 , wherein Ar 1 through Ar 3 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 20 arylene group and a substituted or unsubstituted C 4 -C 20 heteroarylene group.

12. A heterocyclic compound of claim 10 , wherein Ar 1 through Ar 3 are each independently selected from the group consisting of a phenylene group, a C 1 -C 10 alkyl phenylene group, a di(C 1 -C 10 alkyl) phenylene group, a naphthylene group, a C 1 -C 10 alkyl naphthylene group, a di(C 1 -C 10 alkyl) naphthylene group, an anthrylene group, a C 1 -C 10 alkyl anthrylene group, a di(C 1 -C 10 alkyl) anthrylene group, a fluorenylene group, a C 1 -C 10 alkyl fluorenylene group, a di(C 1 -C 10 alkyl) fluorenylene group, a C 6 -C 14 aryl fluorenylene group, a di(C 6 -C 14 aryl) fluorenylene group, a pyridylene group, a C 1 -C 10 alkyl pyridylene group, a di(C 1 -C 10 alkyl) pyridylene group, a carbazolylene group, a C 1 -C 10 alkyl carbazolylene group, and a di(C 1 -C 10 alkyl) carbazolylene group.

13. A heterocyclic compound of claim 10 , wherein Ar 1 through Ar 3 are each independently selected from the groups represented by Formulae 2A through 2G below:

wherein Z 1 , Z 2 , Z 11 and Z 12 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 14 aryl group; p is an integer from 1 to 8; * denotes a binding site with Ar 11 , Ar 12 or Ar 13 ; and *′ denotes a binding site with a ring of Formula 1, wherein at least two adjacent groups of Z 1 , Z 2 , Z 11 and Z 12 may be linked to form a saturated or unsaturated ring.

14. A heterocyclic compound of claim 10 , wherein Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 20 aryl group and a substituted or unsubstituted C 4 -C 20 heteroaryl group.

15. A heterocyclic compound of claim 10 , wherein Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a phenyl group, a C 1 -C 10 alkyl phenyl group, a di(C 1 -C 10 alkyl)phenyl group, a C 6 -C 14 aryl phenyl group, a di(C 6 -C 14 aryl)phenyl group, a naphthyl group, a C 1 -C 10 alkyl naphthyl group, a di(C 1 -C 10 alkyl)naphthyl group, a C 6 -C 14 aryl naphthyl group, a di(C 6 -C 14 aryl)naphthyl group, an anthryl group, a C 1 -C 10 alkyl anthryl group, a di(C 1 -C 10 alkyl)anthryl group, a C 6 -C 14 aryl anthryl group, a di(C 6 -C 14 aryl)anthryl group, a phenanthryl group, a C 1 -C 10 alkyl phenanthryl group, a di(C 1 -C 10 alkyl)phenanthryl group, a C 6 -C 14 aryl phenanthryl group, a di(C 6 -C 14 aryl)phenanthryl group, a fluorenyl group, a C 1 -C 10 alkyl fluorenyl group, a di(C 1 -C 10 alkyl)fluorenyl group, a C 6 -C 14 aryl fluorenyl group, a di(C 6 -C 14 aryl) fluorenyl group, a pyridyl group, a C 1 -C 10 alkyl pyridyl group, a di(C 1 -C 10 alkyl)pyridyl group, a pyrenyl group, a C 1 -C 10 alkyl pyrenyl group, a di(C 1 -C 10 alkyl)pyrenyl group, a C 6 -C 14 aryl pyrenyl group, a di(C 6 -C 14 aryl)pyrenyl group, a phenanthrolinyl group, a C 1 -C 10 alkyl phenanthrolinyl group, a di(C 1 -C 10 alkyl)phenanthrolinyl group, a C 6 -C 14 aryl phenanthrolinyl group, a di(C 6 -C 14 aryl)phenanthrolinyl group, a quinolinyl group, C 1 -C 10 alkyl quinolinyl group, a di(C 1 -C 10 alkyl)quinolinyl group, a C 6 -C 14 aryl quinolinyl group, a di(C 6 -C 14 aryl)quinolinyl group, a benzoxazolyl group, a C 1 -C 10 alkyl benzoxazolyl group, a di(C 1 -C 10 alkyl)benzoxazolyl group, a C 6 -C 14 aryl benzoxazolyl group, a di(C 6 -C 14 aryl)benzoxazolyl group, a benzothiazolyl group, a C 1 -C 10 alkyl benzothiazolyl group, a di(C 1 -C 10 alkyl)benzothiazolyl group, a C 6 -C 14 aryl benzothiazolyl group, a di(C 6 -C 14 aryl)benzothiazolyl group, a benzimidazolyl group, a C 1 -C 10 alkyl benzimidazolyl group, a di(C 1 -C 10 alkyl)benzimidazolyl group, a C 6 -C 14 aryl benzimidazolyl group, a di(C 6 -C 14 aryl)benzimidazolyl group, an imidazolpyridinyl group, a C 1 -C 10 alkyl imidazolpyridinyl group, a di(C 1 -C 10 alkyl) imidazolpyridinyl group, a C 6 -C 14 aryl imidazolpyridinyl group, a di(C 6 -C 14 aryl)imidazolpyridinyl group, an imidazolpyrimidinyl group, a C 1 -C 10 alkyl imidazolpyrimidinyl group, a di(C 1 -C 10 alkyl)imidazolpyrimidinyl group, a C 6 -C 14 aryl imidazolpyrimidinyl group, a di(C 6 -C 14 aryl)imidazolpyrimidinyl group, a carbazolyl group, a C 1 -C 10 alkyl carbazolyl group, a di(C 1 -C 10 alkyl)carbazolyl group, a C 6 -C 14 aryl carbazolyl group, and a di(C 6 -C 14 aryl)carbazolyl group.

16. A heterocyclic compound of claim 10 , wherein Ar 11 , Ar 12 , and Ar 13 are each independently selected from the groups represented by Formulae 3A through 3O below:

wherein Z 1 , Z 2 , Z 3 , Z 11 and Z 12 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 14 aryl group; p is an integer from 1 to 8; and * denotes a binding site with Ar 11 , Ar 12 or Ar 13 , wherein at least two adjacent groups of Z 1 , Z 2 , Z 3 , Z 11 and Z 12 may be linked to form a saturated or unsaturated ring.

17. A heterocyclic compound of claim 10 , wherein a, b, and c are each independently 0, 1, 2 or 3.

18. A heterocyclic compound of claim 10 , wherein R 1 and R 8 are each independently selected from the group consisting of a group represented by —(Ar 1 ) a —(Ar 11 ) and a group represented by —N[—(Ar 2 ) b —(Ar 12 )][—(Ar 3 ) c —(Ar 13 )]; and R 2 and R 3 are each independently selected from the group consisting of a methyl group and a phenyl group;

Ar 1 through Ar 3 are each independently selected from the group consisting of a substituted or unsubstituted C 5 -C 20 arylene group and a substituted or unsubstituted C 4 -C 20 heteroarylene group;

Ar 11 , Ar 12 and Ar 13 are each independently selected from the group consisting of a phenyl group, a C 1 -C 10 alkyl phenyl group, a di(C 1 -C 10 alkyl)phenyl group, a C 6 -C 14 aryl phenyl group, a di(C 6 -C 14 aryl)phenyl group, a naphthyl group, a C 1 -C 10 alkyl naphthyl group, a di(C 1 -C 10 alkyl)naphthyl group, a C 6 -C 14 aryl naphthyl group, a di(C 6 -C 14 aryl)naphthyl group, an anthryl group, a C 1 -C 10 alkyl anthryl group, a di(C 1 -C 10 alkyl)anthryl group, a C 6 -C 14 aryl anthryl group, a di(C 6 -C 14 aryl)anthryl group, a phenanthryl group, a C 1 -C 10 alkyl phenanthryl group, a di(C 1 -C 10 alkyl)phenanthryl group, a C 6 -C 14 aryl phenanthryl group, a di(C 6 -C 14 aryl)phenanthryl group, a fluorenyl group, a C 1 -C 10 alkyl fluorenyl group, a di(C 1 -C 10 alkyl)fluorenyl group, a C 6 -C 14 aryl fluorenyl group, a di(C 6 -C 14 aryl) fluorenyl group, a pyridyl group, a C 1 -C 10 alkyl pyridyl group, a di(C 1 -C 10 alkyl)pyridyl group, a pyrenyl group, a C 1 -C 10 alkyl pyrenyl group, a di(C 1 -C 10 alkyl)pyrenyl group, a C 6 -C 14 aryl pyrenyl group, a di(C 6 -C 14 aryl)pyrenyl group, a phenanthrolinyl group, a C 1 -C 10 alkyl phenanthrolinyl group, a di(C 1 -C 10 alkyl)phenanthrolinyl group, a C 6 -C 14 aryl phenanthrolinyl group, a di(C 6 -C 14 aryl)phenanthrolinyl group, a quinolinyl group, a C 1 -C 10 alkyl quinolinyl group, a di(C 1 -C 10 alkyl)quinolinyl group, a C 6 -C 14 aryl quinolinyl group, a di(C 6 -C 14 aryl)quinolinyl group, a benzoxazolyl group, a C 1 -C 10 alkyl benzoxazolyl group, a di(C 1 -C 10 alkyl)benzoxazolyl group, a C 6 -C 14 aryl benzoxazolyl group, a di(C 6 -C 14 aryl)benzoxazolyl group, a benzothiazolyl group, a C 1 -C 10 alkyl benzothiazolyl group, a di(C 1 -C 10 alkyl)benzothiazolyl group, a C 6 -C 14 aryl benzothiazolyl group, a di(C 6 -C 14 aryl)benzothiazolyl group, a benzimidazolyl group, a C 1 -C 10 alkyl benzimidazolyl group, a di(C 1 -C 10 alkyl)benzimidazolyl group, a C 6 -C 14 aryl benzimidazolyl group, a di(C 6 -C 14 aryl)benzimidazolyl group, an imidazolpyridinyl group, a C 1 -C 10 alkyl imidazolpyridinyl group, a di(C 1 -C 10 alkyl) imidazolpyridinyl group, a C 6 -C 14 aryl imidazolpyridinyl group, a di(C 6 -C 14 aryl)imidazolpyridinyl group, an imidazolpyrimidinyl group, a C 1 -C 10 alkyl imidazolpyrimidinyl group, a di(C 1 -C 10 alkyl)imidazolpyrimidinyl group, a C 6 -C 14 aryl imidazolpyrimidinyl group, a di(C 6 -C 14 aryl)imidazolpyrimidinyl group, a carbazolyl group, a C 1 -C 10 alkyl carbazolyl group, a di(C 1 -C 10 alkyl)carbazolyl group, a C 6 -C 14 aryl carbazolyl group, and a di(C 6 -C 14 aryl)carbazolyl group; and

a, b, and c are each independently 0, 1, 2 or 3.

19. An organic light-emitting device comprising:

a first electrode;

a second electrode disposed opposite to the first electrode; and

an organic layer disposed between the first electrode and the second electrode, the organic layer comprising a heterocyclic compound of claim 1 .

20. The organic light-emitting device of claim 19 , wherein the organic layer is selected from the group consisting of an electron injection layer, an electron transport layer, and an emission layer.

Assignments (1)
MERGER Recorded Sep 21, 2012
From: SAMSUNG MOBILE DISPLAY CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
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