IP Library › Granted Patent US 10,439,149
Granted Patent B2
US 10,439,149 · App. 15/650,077 · Granted Oct 8, 2019

Compound and organic light-emitting device including the same

Inventors: Haejin Kim (Yongin-si, KR); Soobyung Ko (Yongin-si, KR); Mieun Jun (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Seokhwan Hwang (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0071C07D493/04C07D495/04C09K11/06H01L27/32H01L51/0061H01L51/0094C07D325/00H01L51/5056
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Quick Facts
Patent No.
US 10,439,149
App. No.
15/650,077
Granted
Oct 8, 2019
Kind
B2
Abstract

A compound represented by Formula 1 is provided: wherein Formula 1 is the same as described in the detailed description of the present disclosure. The compound of Formula 1 may be included in a hole transport layer and/or an emission layer of an organic light-emitting device (OLED).

Claims (66)

1. A compound represented by Formula 1:

<Formula 1>

wherein, in Formula 1,

R 1 , R 2 , Ar 1 , and Ar 2 are each independently selected from hydrogen, deuterium, 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,

L 1 and L 2 are each independently 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,

Y 1 and Y 2 are each independently selected from N, B, and Si,

X is selected from B, C, Si, Ge, Sn, SO, S(O) 2 , P, PO, and N,

A1 and A2 are each independently a phenylene group or a naphthylene group,

a1, a2, b1, b2, c1, and c2 are each independently an integer from 0 to 3, and

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 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl 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 monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, and the 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 1 -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 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, —CI, —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 X in Formula 1 is selected from B, C, Si, Ge, Sn, SO, S(O) 2 , P, and PO.

3. The compound of claim 1 , wherein R 1 and R 2 in Formula 1 are each independently represented by one of Formulae 2a and 2b:

wherein, in Formulae 2a and 2b, Z 1 is selected from hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy 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 from 1 to 5, and

* indicates a binding site.

4. The compound of claim 1 , wherein each of L 1 and L 2 in Formula 1 is a group represented by Formula 3a:

wherein * in Formula 3a indicates a binding site.

5. The compound of claim 1 , wherein each of Y 1 and Y 2 in Formula 1 is N.

6. The compound of claim 1 , wherein Ar 1 and Ar 2 in Formula 1 are each independently represented by one of Formulae 4a to 4e:

Wherein, in Formulae 4a to 4e, H 1 is O, S, CR 11 R 12 , or NR 13 ,

R 11 to R 13 and Z 1 are each independently selected from hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy 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 from 1 to 9, and

* indicates a binding site.

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

8. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 3:

9. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 4:

<Formula 4>

10. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 5:

11. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 6:

<Formula 6>

12. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 7:

13. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 8:

14. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 9:

<Formula 9>

15. The compound of claim 1 , wherein

the compound represented by Formula 1 is represented by Formula 10:

<Formula 10>

16. The compound of claim 1 , wherein

the compound represented by Formula 1 is any one of compounds below:

17. 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 comprising an emission layer,

wherein the organic layer comprises the compound of claim 1 .

18. The organic light-emitting device of claim 17 , 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, the hole transport region comprising a hole transport layer; and at least one of a hole injection 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 of an electron transport layer, a hole blocking layer, and an electron injection layer.

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

the emission layer or the hole transport layer comprises the compound of Formula I.

20. A display apparatus comprising:

the organic light-emitting device of claim 17 , wherein the first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2017
From: KIM, HAEJIN; KO, SOOBYUNG; JUN, MIEUN; KIM, YOUNGKOOK; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 043007/0770 →
Priority Claims (1)
KR 10-2016-0105582 · Aug 19, 2016 · national
Continuity (1)
Related Publication 20180053902A1 · Feb 22, 2018