IP Library Granted Patent US 9,722,185
Granted Patent B2
US 9,722,185 · App. 14/221,940 · Granted Aug 1, 2017

Heterocyclic compound and organic light-emitting device including the same

Inventor: Jung-Sub Lee (Yongin, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0067H01L51/0072H01L51/0073H01L51/0074H01L51/0094H01L51/006H01L51/0051H01L51/0085H01L51/5016
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,722,185
App. No.
14/221,940
Granted
Aug 1, 2017
Kind
B2
Abstract

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

Claims (136)

1. A heterocyclic compound represented by Formula 1 below:

wherein, in Formula 1,

a moiety represented by

 is one selected from moieties represented by Formulae a to f below;

wherein, in Formulae a to f,

X is —O—, —S—,

and

in Formula 1 and Formulae a to f,

L 1 to L 6 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, and a substituted or unsubstituted C 2 -C 60 heteroarylene group;

n1 to n6 are each independently an integer of 0 to 3;

R 1 to R 10 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, —N(Q 1 )(Q 2 ), and —Si(Q 3 )(Q 4 )(Q 5 ), where Q 1 to Q 5 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, an amino group, a nitro group, a carboxyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, and a substituted or unsubstituted C 2 -C 30 heteroaryl group;

m1 to m4 are each independently an integer of 0 to 5; and

o1 to o3 are each independently an integer of 0 to 2,

provided that at least one of o1 to o3 is 1 or 2 or provided that X is

and

provided that at least one of n1 to n6 is 1, 2, or 3 such that at least one of L 1 to L 6 is present in the compound represented by Formula 1.

2. The heterocyclic compound as claimed in claim 1 , wherein L 1 to L 6 are each independently selected from:

a phenylene group, a naphthylene group, an anthracenyl group, a pyrimidinylene group, a triazinylene group, and a pyridyl group; and

a phenylene group, a naphthylene group, an anthracenyl group, a pyrimidinylene group, a triazinylene group, and a pyridyl group, each substituted with at least one selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group.

3. The heterocyclic compound as claimed in claim 1 , wherein L 1 to L 6 are each independently selected from:

a phenylene group, a pyrimidinylene group, a triazinylene group, and a pyridyl group; and

a phenylene group, a pyrimidinylene group, a triazinylene group, and a pyridyl group, each substituted with at least one selected from

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, and a nitro group;

a phenyl group, a naphthyl group, and an anthracenyl group; and

a phenyl group, a naphthyl group, and an anthracenyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, and a nitro group.

4. The heterocyclic compound as claimed in claim 1 , wherein L 1 to L 6 are each independently selected from:

a phenylene group, a pyrimidinylene group, a triazinylene group, and a pyridyl group; and

a phenylene group, a pyrimidinylene group, a triazinylene group, and a pyridyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthracenyl group.

5. The heterocyclic compound as claimed in claim 1 , wherein n1 to n6 in Formula 1 and Formulae a to f are each independently an integer of 1 or 2.

6. The heterocyclic compound as claimed in claim 1 , wherein at least one of n1 to n6 is 1, 2, or 3, and moieties represented by (L 1 ) n1 , (L 2 ) n2 , (L 3 ) n3 , (L 4 ) n4 , (L 5 ) n5 , and (L 6 ) n6 in Formula 1 and Formulae a to f are each independently selected from moieties represented by Formulae 4-1 to 4-14 below:

wherein, in Formulae 4-1 to 4-14,

Y 1 to Y 18 are each independently selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group,

a1 to a18 are each independently an integer of 0 to 2,

* indicates a binding site to a ring, and

** indicates a binding site to one of R 1 to R 6 .

7. The heterocyclic compound as claimed in claim 1 , wherein at least one of n1 to n6 is 1, 2, or 3, and moieties represented by (L 1 ) n1 , (L 2 ) n2 , (L 3 ) n3 , (L 4 ) n4 , (L 5 ) n5 , and (L 6 ) n6 in Formula 1 and Formulae a to f are each independently selected from moieties represented by Formulae 5-1 to 5-14 below:

wherein, in Formulae 5-1 to 5-14,

Y 1 to Y 13 are each independently selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthracenyl group:

* indicates a binding site to a ring, and

** indicates a binding site to one of R 1 to R 6 .

8. The heterocyclic compound as claimed in claim 1 , wherein at least one of m1 to m6 is 1, 2, 3, 4, or 5, and R 1 to R 6 in Formula 1 and Formulae a to f are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, and groups represented by Formulae 6-1 to 6-13 below:

wherein, in Formulae 6-1 to 6-13,

Z 1 to Z 33 are each independently selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group,

b1 to b6, b8, b10, and b14 to b33 are each independently an integer of 0 to 2, and

* indicates a binding site to one of L 1 to L 6 .

9. The heterocyclic compound as claimed in claim 1 , wherein at least one of m1 to m6 is 1, 2, 3, 4, or 5, and R 1 to R 6 in Formula 1 and Formulae a to f are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, and groups represented by Formulae 7-1 to 7-15 below:

wherein, in Formulae 7-1 to 7-15,

Z 7 , Z 9 , and Z 11 to Z 13 are each independently selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthracenyl group, and

* indicates a binding site to one of L 1 to L 6 .

10. The heterocyclic compound as claimed in claim 1 , wherein R 7 to R 10 in Formula 1 and Formulae a to f are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group.

11. The heterocyclic compound as claimed in claim 1 , wherein R 7 to R 10 in Formula 1 and Formulae a to f are hydrogen atoms.

12. The heterocyclic compound as claimed in claim 1 , wherein o1 to o3 in Formula 1 and Formulae a to f are each independently an integer of 0 or 1 provided that at least one of o1 to o3 is 1 or provided that X is

13. The heterocyclic compound as claimed in claim 1 , wherein the heterocyclic compound of Formula 1 is one selected from compounds represented by Formulae A to C:

wherein, in Formulae A to C,

X is —O—, —S—,

moieties represented by (L 1 ) n1 , (L 2 ) n2 , and (L 4 ) n4 to (L 6 ) n6 are each independently selected from the moieties represented by Formulae 4-1 to 4-14 below:

wherein, in Formulae 4-1 to 4-14,

Y 1 to Y 18 are each independently selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group,

a1 to a18 are each independently an integer of 0 to 2,

* indicates a binding site to a ring, and

** indicates a binding site to one of R 1 , R 2 , and R 4 to R 6 ;

R 1 , R 2 , and R 4 to R 6 in Formulae A to C are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, and groups represented by Formulae 6-1 to 6-13 below:

wherein, in Formulae 6-1 to 6-13,

Z 1 to Z 33 are each independently selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group,

b1 to b6, b8, b10, and b14 to b33 are each independently an integer of 0 to 2,

* indicates a binding site to one of L 1 , L 2 , and L 4 to L 6 , and

m1, m2, and m4 to m6 are each 1;

R 7 to R 10 in Formulae A to C are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group; and

o1 and o2 in Formulae A to C are each independently an integer of 0 or 1 provided that at least one of o1 or o2 is 1 or provided that X is

14. The heterocyclic compound as claimed in claim 1 , wherein the heterocyclic compound of Formula 1 is selected from compounds represented by Formulae 1a to 1c, 2a to 2c, and 3a to 3c:

wherein, in Formulae 1a to 1c, 2a to 2c, and 3a to 3c,

X 1 and X 2 are each independently —O— or —S—;

moieties represented by (L 1 ) n1 , (L 2 ) n2 , and (L 4 ) n4 are each independently selected from moieties represented by Formulae 4-1 to 4-14 below:

wherein, in Formulae 4-1 to 4-14,

Y 1 to Y 18 are each independently selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group,

a1 to a18 are each independently an integer of 0 to 2,

* indicates a binding site to a ring, and

** indicates a binding site to one of R 1 , R 2 , and R 4 ;

R 1 , R 2 , and R 4 in Formulae 1a to 1c, 2a to 2c, and 3a to 3c are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, and groups represented by Formulae 6-1 to 6-13 below:

wherein, in Formulae 6-1 to 6-13,

Z 1 to Z 33 are each independently selected from:

a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkyl group;

a C 1 -C 10 alkyl group substituted with at least one of a deuterium atom, a halogen atom a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group; and

a C 6 -C 16 aryl group and a C 2 -C 16 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 6 -C 16 aryl group, and a C 2 -C 16 heteroaryl group,

b1 to b6, b8, b10, and b14 to b33 are each independently an integer of 0 to 2,

* indicates a binding site to one of L 1 , L 2 , and L 4 ; and

m1, m2, and m4 in Formulae 1a to 1c, 2a to 2c, and 3a to 3c are each 1.

15. The heterocyclic compound as claimed in claim 1 , wherein the heterocyclic compound of Formula 1 is selected from compounds represented by Formulae 1a to 1c, 2a to 2c, and 3a to 3c below:

wherein, in Formulae 1a to 1c, 2a to 2c, and 3a to 3c,

X 1 and X 2 are each independently —O— or —S—;

moieties represented by (L 1 ) n1 , (L 2 ) n2 , and (L 4 ) n4 are each independently selected from moieties represented by Formulae 5-1 to 5-14:

wherein, in Formulae 5-1 to 5-14,

Y 1 to Y 13 are each independently selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthracenyl group,

* indicates a binding site to ring,

** indicates a binding site to one of R 1 , R 2 , and R 4 ; and

R 1 , R 2 , and R 4 in Formulae 1a to 1c, 2a to 2c, and 3a to 3c are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, and groups represented by Formulae 7-1 to 7-15:

wherein, in Formulae 7-1 to 7-15,

Z 7 , Z 9 , and Z 11 to Z 13 are each independently selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a phenyl group, a naphthyl group, and an anthracenyl group, and

* indicates a binding site to one of L 1 , L 2 , and L 4 .

16. The heterocyclic compound as claimed in claim 1 , wherein the heterocyclic compound of Formula 1 is one selected from Compounds 1 to 68 below:

17. An organic light-emitting device comprising:

a first electrode;

a second electrode disposed opposite to the first electrode; and

an organic layer between the first electrode and the second electrode, the organic layer including an emission layer,

wherein the organic layer includes a heterocyclic compound as claimed in claim 1 .

18. The organic light-emitting device as claimed in claim 17 , wherein the organic layer includes:

a hole transport region between the first electrode and the emission layer, the hole transport region including at least one of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport capabilities, a buffer layer, and an electron blocking layer, and

an electron transport region between the emission layer and the second electrode, the electron transport region including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

19. The organic light-emitting device as claimed in claim 17 , wherein the heterocyclic compound is present in the emission layer.

20. The organic light-emitting device as claimed in claim 19 , wherein the emission layer further includes a dopant, and the heterocyclic compound in the emission layer is a host.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 21, 2014
From: LEE, JUNG-SUB
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 032498/0798 →
Priority Claims (1)
KR 10-2013-0095605 · Aug 12, 2013 · national
Continuity (1)
Related Publication 20150041770A1 · Feb 12, 2015