IP Library › Granted Patent US 10,181,562
Granted Patent B2
US 10,181,562 · App. 15/139,208 · Granted Jan 15, 2019

Compound and organic light-emitting device comprising the same

Inventors: Dongwoo Shin (Yongin-si, KR); Seulong Kim (Yongin-si, KR); Younsun Kim (Yongin-si, KR); Jungsub Lee (Yongin-si, KR); Naoyuki Ito (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0072C07D223/14C07D223/18C07D403/14C07D405/14C07F9/6561C09K11/025C09K11/06H01L27/3248H01L51/0052H01L51/0067H01L51/0073H01L51/0077H01L51/0085C09K2211/1007C09K2211/1029C09K2211/185H01L51/001H01L51/0003H01L51/504H01L51/506H01L51/5016H01L51/5028H01L51/5076H01L51/5088H01L51/5092H01L51/5096H01L51/5206H01L51/5221H01L2251/558
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Quick Facts
Patent No.
US 10,181,562
App. No.
15/139,208
Granted
Jan 15, 2019
Kind
B2
Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer including a compound represented by Formula 1: An organic light-emitting device using the compound of Formula 1 may have high efficiency, low voltage, high luminance, and long lifespan.

Claims (58)

1. A compound represented by Formula 1:

wherein, in Formula 1,

R 3 to R 8 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

a, b, e, and f are each independently an integer selected from 1 to 4;

c and d are each independently an integer selected from 1 to 3;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and

—P(═O)Q 31 Q 32 ,

wherein Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 32 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and

when a to f are each independently 2 or more, a respective plurality of R 3 (s) to R 8 (s) are identical to or different from each other;

one of R 1 and R 2 is selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

the other one of R 1 and R 2 is hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 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 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 18 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 10 -C 60 aryl 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or a substituted phenyl group,

wherein a substituent of the substituted phenyl group is selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 7 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 7 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and

—P(═O)Q 31 Q 32 .

2. The compound of claim 1 , wherein, in Formula 1, R 3 to R 8 are each independently hydrogen or deuterium.

3. The compound of claim 1 , wherein, in Formula 1, the one of R 1 and R 2 is selected from a substituted or unsubstituted C 6 -C 60 aryl 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

4. The compound of claim 1 , wherein, in Formula 1, R 1 and R 2 are each independently selected from Formulae 2a to 2c:

wherein, in Formulae 2a to 2c,

Z 1 is selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carboxyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 7 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —P(═O)Q 31 Q 32 ;

p in Formula 2a is an integer selected from 1 to 5, p in Formulae 2b and 2c is an integer selected from 1 to 7, and when p is 2 or more, a respective plurality of Z 1 (s) are identical to or different from each other; and

* indicates a binding site.

5. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 2:

6. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 3:

7. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 4:

8. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 5:

wherein, in Formula 5, R 11 and R 12 are each independently selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 7 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 7 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and

—P(═O)Q 31 Q 32 ,

wherein Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 32 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and

m and n are each independently an integer selected from 1 to 5.

9. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 6:

wherein, in Formula 6, R 21 and R 22 are each independently defined the same as R 3 to R 8 , o is an integer selected from 1 to 5, and p is an integer selected from 1 to 7.

10. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by Formula 7:

wherein, in Formula 7, R 31 is defined the same as R 1 and R 3 to R 8 , and q is an integer selected from 1 to 4.

11. The compound of claim 1 , wherein the compound represented by Formula 1 is represented by one of Compounds 6 to 9, 15 to 18, 21, 22, and 25-69:

12. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer comprises the compound of claim 1 .

13. The organic light-emitting device of claim 12 , wherein

the first electrode is an anode,

the second electrode is a cathode,

and the organic layer further comprises i) a hole transport region between the first electrode and the emission layer, the hole transport region comprising at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and ii) an electron transport region between the emission layer and the second electrode, the electron transport region comprising at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

14. The organic light-emitting device of claim 13 , wherein the emission layer comprises the compound represented by Formula 1.

15. The organic light-emitting device of claim 13 , wherein the emission layer comprises the compound represented by Formula 1 as a host.

16. The organic light-emitting device of claim 13 , wherein the emission layer comprises at least one selected from an iridium (Ir) complex, a platinum (Pt) complex, an osmium (Os) complex, and a copper (Cu) complex as a dopant.

17. The organic light-emitting device of claim 13 , wherein the hole transport region comprises a charge-generating material.

18. The organic light-emitting device of claim 13 , wherein the electron transport region comprises a metal complex.

19. The organic light-emitting device of claim 13 , wherein the electron transport region comprises at least one selected from Compound ET-D1 and Compound ET-D2:

20. A flat panel display apparatus comprising the organic light-emitting device of claim 12 , wherein the first electrode of the organic light-emitting device is electrically coupled to a source electrode or a drain electrode of a thin film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2016
From: SHIN, DONGWOO; KIM, SEULONG; KIM, YOUNSUN; LEE, JUNGSUB; ITO, NAOYUKI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 038388/0601 →
Priority Claims (2)
KR 10-2015-0059636 · Apr 28, 2015 · national
KR 10-2015-0109571 · Aug 3, 2015 · national
Continuity (1)
Related Publication 20160322586A1 · Nov 3, 2016