IP Library › Granted Patent US 12,048,241
Granted Patent B2
US 12,048,241 · App. 15/374,793 · Granted Jul 23, 2024

Carbazole-based compound and organic light-emitting device including the same

Inventors: Seokhwan Hwang (Yongin-si, KR); Jongwoo Kim (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Hyejin Jung (Yongin-si, KR); Sanghyun Han (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/636C07D209/86C07D209/88C07D405/12C09K11/025H10K85/615H10K85/631H10K85/633H10K85/6572H10K85/6574H10K85/6576H10K50/15
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Quick Facts
Patent No.
US 12,048,241
App. No.
15/374,793
Granted
Jul 23, 2024
Kind
B2
Abstract

An organic light-emitting device including: 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 a carbazole-based compound represented by Formula 1A or 1B: When the carbazole-based compound represented by Formula 1A or 1B is included in the hole transport layer, an organic light-emitting device may have improved driving voltage, efficiency, luminance, and lifespan characteristics.

Claims (56)

1. A carbazole-based compound represented by Formula 1B-2 or 1B-3:

wherein, in Formulae 1B-2 and 1B-3,

L 1 and L 2 are each independently selected from:

a phenylene group and a naphthylene group; and

a phenylene group and a naphthylene group, each substituted with at least one selected from deuterium, —F, a cyano group, 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, and —Si(Q 31 )(Q 32 )(Q 33 ),

a1 and a2 are each independently an integer selected from 0, 1, 2, and 3; wherein when a1 is two or more, two or more L 1 (s) are identical to or different from each other; when a2 is two or more, two or more L 2 (s) are identical to or different from each other,

Ar 1 is a biphenyl group, a terphenyl group, or a naphthyl group, each substituted with —N(Q 31 )(Q 32 ), or is a group represented by Formula 6-11:

Ar 2 is selected from the group consisting of:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, and a naphthyl group; and

a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, —F, a cyano group, 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, and —Si(Q 31 )(Q 32 )(Q 33 ),

Ar 3 is selected from the group consisting of:

a C 2 -C 20 alkyl group;

a C 2 -C 20 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group;

a phenyl group; and

a phenyl group substituted with at least one selected from deuterium, —F, a cyano group, and a C 1 -C 10 alkyl group,

R 1 to R 5 are each independently selected from hydrogen, deuterium, —F, a cyano group, a nitro group, 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, and —Si(Q 1 )(Q 2 )(Q 3 ),

b1 and b3 to b5 are each independently an integer selected from 0 to 4, and b2 is an integer selected from 0 to 3; wherein when b1 is two or more, two or more R 1 (s) are identical to or different from each other; when b2 is two or more, two or more R 2 (s) are identical to or different from each other; when b3 is two or more, two or more R 3 (s) are identical to or different from each other; when b4 is two or more, two or more R 4 (s) are identical to or different from each other; and when b5 is two or more, two or more R5(s) are identical to or different from each other, and

wherein Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

2. The carbazole-based compound of claim 1 , wherein:

L 1 and L 2 are each independently selected from groups represented by Formulae 3-1, 3-2, 3-5, 3-6, 3-7, 3-33, 3-34, 3-42 and 3-43:

wherein, in Formulae 3-1, 3-2, 3-5, 3-6, 3-7, 3-33, 3-34, 3-42 and 3-43,

Z 1 is selected from hydrogen, deuterium, —F, cyano group, 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, —Si(Q 31 )(Q 32 )(Q 33 ),

Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,

d4 is an integer selected from 0 to 4,

d6 is an integer selected from 0 to 6, and

* and *′ each indicate a binding site to a neighboring atom.

3. The carbazole-based compound of claim 1 , wherein a1 and a2 are each independently 0, 1, or 2.

4. The carbazole-based compound of claim 1 , wherein:

Ar 2 is selected from groups represented by Formulae 5-1 to 5-3:

wherein, in Formulae 5-1 to 5-3,

Z 31 is selected from hydrogen, deuterium, —F, a cyano group, 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, —N(Q 31 )(Q 32 ), and —Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group;

e5 is an integer selected from 0 to 5,

e7 is an integer selected from 0 to 7, and

indicates a binding site to a neighboring atom.

5. The carbazole-based compound of claim 1 , wherein:

Ar 3 is selected from the group consisting of:

a phenyl group; and

a phenyl group substituted with at least one selected from deuterium, —F, a cyano group, and a C 1 -C 10 alkyl group.

6. 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 at least one of the carbazole-based compounds of claim 1 .

7. The organic light-emitting device of claim 6 , wherein:

the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

8. The organic light-emitting device of claim 7 , wherein the hole transport region comprises the carbazole-based compound.

9. The organic light-emitting device of claim 7 , wherein

the hole transport region comprises a hole transport layer, which comprises the carbazole-based compound.

10. The organic light-emitting device of claim 7 , wherein the hole transport region comprises an emission auxiliary layer, which comprises the carbazole-based compound.

11. The organic light-emitting device of claim 6 , wherein the emission layer comprises an anthracene-based compound.

12. A compound 37:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2016
From: HWANG, SEOKHWAN; KIM, JONGWOO; KIM, YOUNGKOOK; JUNG, HYEJIN; HAN, SANGHYUN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 040730/0434 →
Priority Claims (1)
KR 10-2015-0184064 · Dec 22, 2015 · national
Continuity (1)
Related Publication 20170179400A1 · Jun 22, 2017