IP Library › Granted Patent US 10,326,080

Granted Patent B2

US 10,326,080 · App. 15/960,254 · Granted Jun 18, 2019

Organic light-emitting devices

Inventors: Hwan-Hee Cho (Yongin, KR); Mi-Kyung Kim (Yongin, KR); Jae-Yong Lee (Yongin, KR); Dong-Hyun Kim (Yongin, KR); Se-Hun Kim (Yongin, KR); Chang-Woong Chu (Yongin, KR)

Assignee: Samsung Display Co., Ltd.

H01L51/0067 H01L51/0052 H01L51/0054 H01L51/0058 H01L51/0059 H01L51/0071 H01L51/0072 H01L51/0073 H01L51/0074 H01L51/0094 H01L51/5016 H01L2251/5384

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Quick Facts

Patent No.: US 10,326,080
App. No.: 15/960,254
Granted: Jun 18, 2019
Kind: B2

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Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer including an emission layer between the first electrode and the second electrode. The emission layer includes at least one compound selected from carbazole-based compounds, and at least one compound selected from heterocyclic compounds as described in the detailed description.

Claims (109)

1. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

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

wherein the emission layer comprises at least one compound selected from carbazole-based compounds represented by Formula 1, and at least one compound selected from heterocyclic compounds represented by Formulae 10A, 10B 10C, 10D, and 10E:

wherein, in Formulae 1, 10A, 10B, 10C, 10D, and 10E, A 11 to A 14 , A 21 , and A 22 are each independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, 2,6-naphthyridine, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7- naphthyridine, 2,7-naphthyridine, quinoxaline, phthalazine, and quinazoline;

X 11 is O, S, C(R 16 )(R 17 ), Si(R 16 )(R 17 ), P(R 16 ), B(R 16 ), P(═O)(R 16 ), or N(R 16 );

X 21 is N-(L 21 ) a21 -R 21 , and X 22 is O or S; or X 21 is O or S, and X 22 is N-(L 21 ) a21 -R 21 ;

L 11 is selected from:

a C 3 -C 10 cycloalkylene group, a C 3 -C 10 heterocycloalkylene group, a C 3 -C 10 cycloalkenylene group, a C 3 -C 10 heterocycloalkenylene group, a C 6 -C 60 arylene group, a C 1 -C 60 heteroarylene group, a divalent nonaromatic condensed polycyclic group, and a divalent nonaromatic condensed heteropolycyclic group; and

a C 3 -C 10 cycloalkylene group, a C 3 -C 10 heterocycloalkylene group, a C 3 -C 10 cycloalkenylene group, a C 3 -C 10 heterocycloalkenylene group, a C 6 -C 60 arylene group, a C 2 -C 60 heteroarylene group, a divalent nonaromatic condensed polycyclic group, and a divalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium; —F; —Cl; —Br; —I; a C 1 -C 60 alkyl group; a C 6 -C 60 aryl group; a monovalent nonaromatic condensed polycyclic group; and a monovalent nonaromatic condensed heteropolycyclic group; except for a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a nitrogen (N)-containing C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;

a11 is an integer selected from 0 to 5;

R 11 , R 16 , and R 17 are each independently selected from:

a hydrogen, a C 1 -C 60 alkyl group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and

a C 1 -C 60 alkyl group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium; —F; —Cl; —Br; —I; a C 1 -C 60 alkyl group; a C 6 -C 60 aryl group; a monovalent nonaromatic condensed polycyclic group; and a monovalent nonaromatic condensed heteropolycyclic group; except for a nitrogen (N)-containing C 1 -C 60 heteroaryl group, and a nitrogen (N)-containing C 1 -C 60 heteroaryl group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;

L 21 is selected from a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;

a21 is an integer selected from 0 to 5;

R 21 is selected from:

R 12 to R 15 , and R 22 to R 24 are each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 2 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;

a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -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 2 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group; and

—N(Q 21 )(Q 22 );

b12 to b15, and b22 to b24 are each independently an integer selected from 1 to 5; and

Q 11 , Q 12 , Q 21 , and Q 22 are each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group,

wherein -(L 11 ) a11 -R 11 is free of a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a nitrogen (N)-containing C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group; and

when a21 is 0, R 21 is selected from a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group.

2. The organic light-emitting device of claim 1 , wherein X 11 is O, S, C(R 16 )(R 17 ), or N(R 16 );

R 16 , and R 17 are each independently selected from:

a hydrogen, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and —N(Q 11 )(Q 12 ); and

a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and monovalent nonaromatic condensed polycyclic group; and

Q 11 and Q 12 are each independently selected from a hydrogen, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group.

3. The organic light-emitting device of claim 1 , wherein L 11 is selected from:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, and an ovalenylene group; and

4. The organic light-emitting device of claim 1 , wherein R 11 is seleced from:

a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and

a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group; and

Q 11 and Q 12 are each independently selected from a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group.

5. The organic light-emitting device of claim 1 , wherein L 21 is selected from:

a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, an indolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a triazolylene group, and a tetrazolylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group.

6. The organic light-emitting device of claim 1 , wherein R 21 is selected from: a hydrogen, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and

a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group; and

Q 11 and Q 12 are each independently selected from a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group.

7. The organic light-emitting device of claim 1 , wherein R 12 to R 15 , and R 22 to R 24 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, and —N(Q 21 )(Q 22 ); and

Q 21 and Q 22 are each independently selected from a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group.

8. The organic light-emitting device of claim 1 , wherein the carbazole-based compound represented by Formula 1 is selected from Compounds 101A to 163A, and the heterocyclic compound represented by Formulae 10A, 10B, 10C, 10D, and 10E is selected from Compounds 109, 112, 113, 119, 122, 125, 126, 128, 131, 132, 219, 220, and 234:

9. The organic light-emitting device of claim 1 , wherein the emission layer further comprises a phosphorescent dopant.

10. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

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

wherein, in Formulae 1, and 10A, 10B, 10C, 10D, and 10E,

A 11 to A 14 , A 21 , and A 22 are each independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, 2,6-naphthyridine, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, 2,7-naphthyridine, quinoxaline, phthalazine, and quinazoline;

X 11 is O, S, C(R 16 )(R 17 ), Si(R 16 )(R 17 ), P(R 16 ), B(R 16 ), P(═O)(R 16 ), or N(R 16 );

X 21 is N-(L 21 ) a21 -R 21 , and X 22 is O or S; or X 21 is O or S, and X 22 is N-(L 21 ) a21 -R 21 ;

L 11 is selected from:

a nitrogen (N)-containing C 1 -C 60 heteroarylene group; and

a C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group;

a11 is an integer selected from 0 to 5;

R 11 , R 16 , and R 17 are each independently selected from:

L 21 is selected from:

a21 is an integer selected from 0 to 5;

R 21 is selected from:

R 12 to R 15 , and R 22 to R 24 are each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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;

—N(Q 21 )(Q 22 );

b12 to b15, and b22 to b24 are each independently an integer selected from 1 to 5; and

Q 11 , Q 12 , Q 21 , and Q 22 are each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group,

wherein:

when a11 is 0, R 11 is selected from a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a C 1 -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group; and

-(L 21 ) a21 -R 21 is free of a nitrogen (N)-containing C 1 -C 60 heteroarylene group, and a nitrogen (N)-containing C l -C 60 heteroarylene group substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, and a monovalent nonaromatic condensed heteropolycyclic group.

11. The organic light-emitting device of claim 10 , wherein X 11 is O, S, C(R 16 )(R 17 ), or N(R 16 );

R 16 and R 17 are each independently selected from:

a hydrogen, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and —N(Q 11 )(Q 12 ); and

Q 11 and Q 12 are each independently selected from a hydrogen, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group.

12. The organic light-emitting device of claim 10 , wherein L 11 is selected from:

13. The organic light-emitting device of claim 10 , wherein R 11 is selected from:

a hydrogen, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and

Q 11 and Q 12 are each independently selected from a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group.

14. The organic light-emitting device of claim 10 , wherein L 21 is selected from:

15. The organic light-emitting device of claim 10 , wherein R 21 is selected from:

a C 6 -C 60 aryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, and —N(Q 11 )(Q 12 ); and

Q 11 and Q 12 are each independently selected from a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group.

16. The organic light-emitting device of claim 10 , wherein R 12 to R 15 , and R 22 to R 24 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, and —N(Q 21 )(Q 22 ); and

Q 21 and Q 22 are each independently selected from a C 6 -C 60 aryl group, and a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group.

17. The organic light-emitting device of claim 10 , wherein the carbazole-based compound represented by Formula 1 is selected from Compounds 101B to 196B:

18. The organic light-emitting device of claim 10 , wherein the emission layer further comprises a phosphorescent dopant.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 23, 2018

From: CHO, HWAN-HEE; KIM, MI-KYUNG; LEE, JAE-YONG; KIM, DONG-HYUN; KIM, SE-HUN; CHU, CHANG-WOONG

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 045615/0200 →

Priority Claims (1)

KR 10-2014-0017518 · Feb 14, 2014 · national

Continuity (2)

Division 14447559 · Jul 30, 2014

Related Publication 20180240981A1 · Aug 23, 2018