IP Library › Granted Patent US 9,761,809
Granted Patent B2
US 9,761,809 · App. 14/683,744 · Granted Sep 12, 2017

Compound and organic light-emitting device comprising same

Inventors: Jongwoo Kim (Yongin, KR); Youngkook Kim (Yongin, KR); Seunggak Yang (Yongin, KR); Jino Lim (Yongin, KR); Hyungseok Jang (Yongin, KR); Seokhwan Hwang (Yongin, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0061C07D209/86C07D401/14C07D403/14C07D405/14C09K11/06H01L51/006C09K2211/1029H01L51/0052H01L51/0058H01L51/0067H01L51/0071H01L51/0072H01L51/5056H01L51/5072H01L2251/301H01L2251/308
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 9,761,809
App. No.
14/683,744
Granted
Sep 12, 2017
Kind
B2
Abstract

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

Claims (55)

1. A compound represented by Formula 1 below:

wherein in Formula 1,

R 1 to R 22 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 );

L is selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group; a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group; a substituted or unsubstituted C 3 -C 10 cycloalkenylene group; a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group; a substituted or unsubstituted C 6 -C 60 arylene group; a substituted or unsubstituted C 2 -C 60 heteroarylene group; a substituted or unsubstituted divalent non-aromatic condensed polycyclic group; a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group; a substituent comprising two or more groups selected from the C 3 -C 10 cycloalkylene group, the C 2 -C 10 heterocycloalkylene group, the C 3 -C 10 cycloalkenylene group, the C 2 -C 10 heterocycloalkenylene group, the C 6 -C 60 arylene group, the C 2 -C 60 heteroarylene group, the divalent non-aromatic condensed polycyclic group, and the divalent non-aromatic condensed heteropolycyclic group;

adjacent substituents from among R 1 to R 22 are separate or are connected to form a ring;

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 2 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C 3 -C 10 cycloalkylene group, substituted C 2 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 2 -C 10 heterocycloalkenylene group, substituted C 6 -C 60 arylene group, substituted C 2 -C 60 heteroarylene group, substituted a divalent non-aromatic condensed polycyclic group and substituted a divalent non-aromatic condensed heteropolycyclic group, is 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 2 -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 2 -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 2 -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 a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 2 -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

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), and —B(Q 36 )(Q 37 );

wherein Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 37 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 group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

2. The compound as claimed in claim 1 , wherein in Formula 1, R 1 to R 22 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 2 -C 60 alkenyl group, and a substituted or unsubstituted C 6 -C 60 aryl group.

3. The compound as claimed in claim 1 , wherein in Formula 1, L is selected from a substituted or unsubstituted C 6 -C 60 arylene group; a substituted or unsubstituted C 2 -C 60 heteroarylene group; or a substituent that includes two or more groups selected from the C 6 -C 60 arylene group and the C 2 -C 60 heteroarylene group.

4. The compound as claimed in claim 1 , wherein

in Formula 1, R 1 to R 12 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 2 -C 10 alkenyl group, or a group represented Formula 2a below:

wherein, in Formula 2a, Z 1 is a hydrogen, a deuterium, 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 C 6 -C 20 condensed polycyclic group, halogen group, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group;

p is an integer selected from 1 to 5; and

* denotes a bonding site to a neighboring atom.

5. The compound as claimed in claim 1 , wherein in Formula 1, R 1 to R 12 are each independently a hydrogen or a deuterium.

6. The compound of claim 1 , wherein in Formula 1, R 13 to R 22 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 2 -C 10 alkenyl group, or a group represented by one of Formulae 3a to 3c below:

wherein in Formulae 3a to 3c, Z 1 and Z 2 are each independently a hydrogen, a deuterium, 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 C 6 -C 20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group;

p and q are each independently an integer selected from 1 to 5; and

* denotes a bonding site to a neighboring atom.

7. The compound as claimed in claim 1 , wherein, in Formula 1, L is a group represented by one of Formulae 4a to 4f below:

wherein, in Formulae 4a to 4f, * denotes a bonding site to a neighboring atom.

8. The compound as claimed in claim 1 , wherein the compound represented by Formula 1 is represented by Formula 2 below:

wherein, in Formula 2, R 1 to R 22 are the same as those defined with respect to Formula 1.

9. The compound as claimed in claim 1 , wherein the compound represented by Formula 1 is represented by Formula 3 below:

wherein, in Formula 3, R 1 to R 22 are the same as those defined with respect to Formula 1.

10. The compound as claimed in claim 1 , wherein the compound represented by Formula 1 is one of the following compounds:

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, the organic layer including an emission layer,

wherein the organic layer includes the compound of claim 1 .

12. The organic light-emitting device as claimed in claim 11 , wherein the organic layer is formed by using wet process.

13. The organic light-emitting device as claimed in claim 11 , wherein:

the first electrode is an anode,

the second electrode is a cathode,

and the organic layer further includes:

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

14. The organic light-emitting device as claimed in claim 13 , wherein the hole transport region includes the compound.

15. The organic light-emitting device as claimed in claim 13 , wherein:

the hole transport region includes the hole transport layer, and

the hole transport layer includes the compound.

16. The organic light-emitting device as claimed in claim 13 , wherein the electron transport region comprises a metal complex.

17. The organic light-emitting device as claimed in claim 16 , wherein the metal complex is a lithium (Li) complex.

18. The organic light-emitting device as claimed in claim 16 , wherein the metal complex is lithium quinolate (LiQ).

19. The organic light-emitting device as claimed in claim 16 , wherein the metal complex is Compound ET-D2 below:

20. A flat display apparatus comprising:

a thin film transistor, the thin film transistor including a source electrode and a drain electrode; and

the organic light-emitting device as claimed in claim 11 ,

wherein the first electrode of the organic light-emitting device is electrically connected to the source electrode or the drain electrode of the thin film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2015
From: KIM, JONGWOO; KIM, YOUNGKOOK; YANG, SEUNGGAK; LIM, JINO; JANG, HYUNGSEOK; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 035383/0077 →
Priority Claims (1)
KR 10-2014-0151583 · Nov 3, 2014 · national
Continuity (1)
Related Publication 20160126465A1 · May 5, 2016