IP Library Granted Patent US 11,180,513
Granted Patent B2
US 11,180,513 · App. 16/509,333 · Granted Nov 23, 2021

Compound and organic light-emitting device including the same

Inventors: Yeseul Lee (Yongin-si, KR); Hyeongmin Kim (Yongin-si, KR); Heechoon Ahn (Yongin-si, KR); Hyunah Um (Yongin-si, KR); Yirang Im (Yongin-si, KR); Soobyung Ko (Yongin-si, KR); Jongwoo Kim (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
C07F7/0816H01L51/0094H01L51/5008H01L51/5072H01L51/5092
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Quick Facts
Patent No.
US 11,180,513
App. No.
16/509,333
Granted
Nov 23, 2021
Kind
B2
Abstract

Provided is a compound represented by Formula 1 and an organic light-emitting device including the same. The 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, the organic layer including an emission layer and the compound represented by Formula 1.

Claims (70)

1. A compound represented by Formula 1:

wherein, in Formula 1,

X 1 and X 2 are each independently selected from a single bond, O, S, NR 11 R 12 , CR 13 R 14 , and SiR 15 R 16 ,

R 1 to R 9 and R 11 to R 16 are each independently selected from hydrogen, deuterium, 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 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),

L 1 to L 4 are each independently selected from a single bond, a substituted or unsubstituted C 4 -C 60 carbocyclic group, and a substituted or unsubstituted C 1 -C 60 heterocyclic group, wherein a case where L 2 to L 4 are each a single bond at the same time is excluded,

n is 0 or 1,

a1 and a2 are each independently 0 or 1,

when a2 is 0, n is 0,

b3, b4, and b6 to b9 are each independently an integer from 1 to 4,

b5 is an integer from 1 to 5,

when b3 to b9 are each independently two or more, two or more adjacent substituents selected from R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are coupled to form a ring,

at least one substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 arylene group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroarylene group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 4 -C 60 carbocyclic group, and the substituted C 1 -C 60 heterocyclic group is selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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;

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 amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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 amidino group, a hydrazino group, a hydrazono group, 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 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -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, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

2. The compound of claim 1 , wherein:

X 1 and X 2 are each independently selected from a single bond, O, S, CR 13 R 14 , and SiR 15 R 16 .

3. The compound of claim 1 , wherein:

L 1 to L 4 are each independently selected from a single bond, a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group.

4. The compound of claim 1 , wherein:

L 1 and L 2 are each a phenylene group at the same time, and L 3 and L 4 are each independently a single bond or a phenylene group.

5. The compound of claim 1 , wherein:

R 1 and R 2 are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group.

6. The compound of claim 1 , wherein:

R 1 and R 2 are each independently represented by Formula 2a:

wherein, in Formula 2a, R 21 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group,

a21 is an integer from 0 to 4, and

* indicates a binding site to a neighboring atom.

7. The compound of claim 1 , wherein:

R 11 to R 16 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.

8. The compound of claim 1 , wherein:

R 3 , R 4 , and R 5 are each independently selected from hydrogen, deuterium, —N(Q 1 )(Q 2 ), and a group represented by Formula 3a:

wherein, in Formula 3a, R 31 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group,

a31 is an integer from 0 to 4, and

* indicates a binding site to a neighboring atom.

9. The compound of claim 1 , wherein:

R 6 to R 9 are each independently selected from hydrogen, deuterium, —Si(Q 1 )(Q 2 )(Q 3 ), a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.

10. The compound of claim 1 , wherein:

the compound represented by Formula 1 is selected from Compounds 1 to 33:

11. 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 .

12. The organic light-emitting device of claim 11 , wherein:

the first electrode is an anode,

the second electrode is a cathode, and

the organic layer between the first electrode and the second electrode and comprising the emission layer comprises i) a hole transport region between the first electrode and the emission layer and comprising a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer, or any combination thereof and ii) an electron transport region between the emission layer and the second electrode and comprising a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

13. The organic light-emitting device of claim 11 , wherein:

the emission layer is a phosphorescence emission layer.

14. The organic light-emitting device of claim 11 , wherein:

the emission layer is a fluorescence emission layer.

15. The organic light-emitting device of claim 11 , wherein:

the emission layer is a phosphorescence emission layer, and the compound is a host.

16. The organic light-emitting device of claim 11 , wherein:

the emission layer comprises an iridium complex as a phosphorescent dopant.

17. The organic light-emitting device of claim 11 , wherein:

the emission layer comprises Ir(pmp) 3 as a phosphorescent dopant.

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

the electron transport region comprises a metal-containing material.

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

the electron injection layer comprises an alkali metal halide.

20. An electronic apparatus comprising:

a thin-film transistor; and

the organic light-emitting device of claim 11 ,

wherein the thin-film transistor comprises a source electrode, a drain electrode, an activation layer, and a gate electrode, and

the first electrode of the organic light-emitting device is electrically coupled to one of the source electrode and the drain electrode of the thin-film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: LEE, YESEUL; KIM, HYEONGMIN; AHN, HEECHOON; UM, HYUNAH; IM, YIRANG; KO, SOOBYUNG; KIM, JONGWOO
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 050128/0778 →
Priority Claims (1)
KR 10-2019-0023293 · Feb 27, 2019 · national
Continuity (1)
Related Publication 20200270283A1 · Aug 27, 2020