IP Library › Granted Patent US 10,003,029
Granted Patent B2
US 10,003,029 · App. 15/140,342 · Granted Jun 19, 2018

Compound and organic light-emitting device including the same

Inventors: Hyejin Jung (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Seokhwan Hwang (Yongin-si, KR); Kwanghyun Kim (Yongin-si, KR); Sanghyun Han (Yongin-si, KR); Miehwa Park (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/006C07C211/54C07C211/61C07D209/80C07D209/86C07D209/88C07D213/38C07D307/91C07D405/04C07D405/12C07F7/0818H01L51/0061C07C2603/18C07C2603/26C07C2603/40C07F7/0812H01L51/001H01L51/0003H01L51/0056H01L51/0058H01L51/0067H01L51/0072H01L51/0073H01L51/506H01L2251/308
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Quick Facts
Patent No.
US 10,003,029
App. No.
15/140,342
Granted
Jun 19, 2018
Kind
B2
Abstract

An organic light-emitting device includes a first electrode; a second electrode facing the first electrode; and an organic emission layer between the first electrode and the second electrode. The organic emission layer may include a compound represented by Formula 1: wherein Formula 1 contains an indenoindenyl moiety. The compound may increase hole mobility in the device when used as a hole transport and/or hole injection material, thereby improving its lifetime, current, voltage, and luminescent characteristics.

Claims (52)

1. A compound represented by Formula 1:

wherein, in Formula 1,

R 1 to R 4 are each independently selected from hydrogen, deuterium, a halogen, an amino group, a nitro group, a nitrile group, 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,

Ar 1 and Ar 2 are each independently selected from 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;

X is selected from a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

n is an integer selected from 0 to 5, and

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, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, and substituted divalent 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; and

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 ),

wherein Q 11 to Q 17 and Q 21 to Q 27 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.

2. The compound of claim 1 , wherein, in Formula 1, R 1 to R 4 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group.

3. The compound of claim 1 , wherein, in Formula 1, adjacent substituents of R 1 to R 4 are linked to form a ring.

4. The compound of claim 1 , wherein, in Formula 1, Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl 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.

5. The compound of claim 1 , wherein, in Formula 1, X is at least one group selected from Formulae 2a and 2b:

wherein, in Formulae 2a and 2b, * denotes a binding site.

6. The compound of claim 1 , wherein, in Formula 1, Ar 1 and Ar 2 are each independently selected from Formulae 3a to 3g:

wherein, in Formulae 3a to 3g,

H 1 denotes O, S, NR 31 , or CR 32 R 33 ,

R 31 to R 33 , R 21 , and Z 1 are each independently selected from hydrogen, deuterium, a halogen, SiR 41 R 42 R 43 , a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

R 41 to R 43 are each independently selected from a substituted or unsubstituted C 1 -C 20 alkyl group and a substituted or unsubstituted C 6 -C 20 aryl group,

p denotes an integer selected from 1 to 9, and

* denotes a binding site.

7. The compound of claim 6 , wherein R 32 and R 33 are linked to form a ring.

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

wherein, in Formulae 4a to 4c,

Z 1 is selected from hydrogen, deuterium, a halogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

p is an integer selected from 1 to 5, and

* denotes a binding site.

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

wherein, in Formula 2, a, b, c, and d are each independently an integer selected from 0 and 1.

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

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

12. The compound of claim 1 , wherein the compound represented by Formula 1 is selected from the compounds below:

13. 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 .

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

the first electrode is an anode,

the second electrode is a cathode, and

the organic layer comprises:

i) a hole transport region between the first electrode and the emission layer and comprising a hole transport layer and at least one layer selected from a hole injection layer and an electron blocking layer; and

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

15. The organic light-emitting device of claim 14 , wherein the hole transport region comprises the compound of claim 1 .

16. The organic light-emitting device of claim 14 , wherein the hole transport layer comprises the compound of claim 1 .

17. The organic light-emitting device of claim 14 , wherein the hole transport region comprises a charge-generating material.

18. The organic light-emitting device of claim 17 , wherein the charge-generating material is a p-dopant.

19. The organic light-emitting device of claim 18 , wherein the p-dopant is selected from a quinone derivative, a metal oxide, and a compound containing a cyano group.

20. A display device comprising the organic light-emitting device of claim 13 , in which a first electrode is electrically connected to a source electrode or a drain electrode of a thin film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2016
From: JUNG, HYEJIN; KIM, YOUNGKOOK; HWANG, SEOKHWAN; KIM, KWANGHYUN; HAN, SANGHYUN; PARK, MIEHWA
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 038445/0223 →
Priority Claims (1)
KR 10-2015-0096778 · Jul 7, 2015 · national
Continuity (1)
Related Publication 20170012205A1 · Jan 12, 2017