IP Library › Granted Patent US 10,043,983

Granted Patent B2

US 10,043,983 · App. 14/963,862 · Granted Aug 7, 2018

Condensed cyclic compound and organic light-emitting device including the same

Inventors: Soonok Jeon (Seoul, KR); Sangmo Kim (Hwaseong-si, KR); Hyunjung Kim (Suwon-si, KR); Yeonsook Chung (Seoul, KR); Yongsik Jung (Yongin-si, KR); Miyoung Chae (Suwon-si, KR); Dalho Huh (Suwon-si, KR); Jongsoo Kim (Suwon-si, KR); Myungsun Sim (Seoul, KR)

Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

H01L51/0072 C07D401/10 C09K11/025 C09K11/06 H01L51/005 C09K2211/1007 C09K2211/1022 C09K2211/1044 C09K2211/185 H01L51/5016

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Quick Facts

Patent No.: US 10,043,983
App. No.: 14/963,862
Granted: Aug 7, 2018
Kind: B2

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Abstract

A condensed cyclic compound represented by Formula 1: wherein, in Formula 1, X 1 to X 8 , X 11 to X 18 , Y 11 , and Z 11 to Z 14 are the same as described in the specification.

Claims (120)

1. A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1,

X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 6 is N or C(R 5 ), X 6 is N or C(R 6 ), X 7 is N or C(R 7 ), X 8 is N or C(R 8 ), X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ), X 17 is N or C(R 17 ), and X 18 is N or C(R 18 );

Y 11 is O, S, C(R 101 )(R 102 ), or Si(R 101 )(R 102 );

Z 11 to Z 14 are each independently selected from N, C(A 11 ), and C(A 12 );

at least one of Z 11 to Z 14 is C(A 11 );

A 11 comprises at least one cyano group (CN); and is a cyano group (CN) or a group represented by one of Formulae 2-1 to 2-10;

A 12 is hydrogen, deuterium, —F, a hydroxyl group, a cyano group (CN), 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, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, a hydroxyl group, a cyano group (CN), 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, and a phosphoric acid group or a salt thereof;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl 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 pyridinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 31 )(Q 32 )(Q 33 );

wherein, in Formulae 2-1 to 2-10,

X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), X 24 is N or C(R 24 ), X 25 is N or C(R 25 ),

R 1 to R 8 , R 11 to R 18 , R 101 , R 102 , R 21 to R 25 , and R 201 to R 203 are each independently selected from

hydrogen, deuterium, —F, a hydroxyl group, a cyano group (CN), 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, and a C 1 -C 20 alkoxy group;

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

—Si(Q 11 )(Q 12 )(Q 13 ),

R 101 and R 102 are optionally linked to each other to form a saturated ring or an unsaturated ring;

b201 is selected from 1, 2, 3, 4, and 5;

b202 and b203 are each independently selected from 1, 2, 3, and 4; and

* indicates a carbon atom in Formula 1,

wherein 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, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

2. The condensed cyclic compound of claim 1 , wherein

X 1 is N, X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 15 );

X 1 is C(R 1 ), X 2 is N, X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is N, X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 5 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is N, X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is O(R 15 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is N, X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is N, X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is N, X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is N, X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 ); or

X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 16 is C(R 16 ), X 17 is C(R 17 ), and X 18 is C(R 18 ).

3. The condensed cyclic compound of claim 1 , wherein

A 11 is a cyano group (CN) or a group represented by one of Formulae 2-1 to 2-7.

4. The condensed cyclic compound of claim 1 , wherein

A 11 is a cyano group (CN) or a group represented by one of Formulae 3-1 to 3-110:

wherein, in Formulae 3-1 to 3-110,

* indicates a carbon atom in Formula 1; and

X 21 to X 25 , R 202 , R 203 , b201 and b202 are the same as in Formulae 2-1 to 2-10.

5. The condensed cyclic compound of claim 1 , wherein

A 11 is a cyano group (ON) or a group represented by one of Formulae 4-1 to 4-110:

wherein, in Formulae 4-1 to 4-110;

* indicates a carbon atom in Formula 1; and

R 202 , R 203 , b201 and b202 are the same as in Formulae 2-1 to 2-10.

6. The condensed cyclic compound of claim 1 , wherein

a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; 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 naphthyl group, and a pyridinyl group.

7. The condensed cyclic compound of claim 1 , wherein

R 1 to R 8 , R 11 to R 18 , R 101 , R 102 , R 21 to R 25 , and R 201 to R 203 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 methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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 group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; and

—Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently selected from hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

8. The condensed cyclic compound of claim 1 , wherein

R 1 to R 8 , R 11 to R 18 , R 21 to R 25 , and R 201 to R 203 are each independently selected from

hydrogen, deuterium, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently selected from hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group.

9. The condensed cyclic compound of claim 1 , wherein

R 101 and R 102 are linked to each other to from a structure represented by Formula 8:

wherein, in Formula 8,

* indicates a carbon atom belonging to Y 11 in Formula 1,

X 81 is N or C(R 81 ), X 82 is N or C(R 82 ), X 83 is N or C(R 83 ), X 84 is N or C(R 84 ), X 85 is N or C(R 85 ), X 86 is N or C(R 86 ), X 87 is N or C(R 87 ), and X 88 is N or C(R 88 ), and

R 81 to R 88 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 31 to Q 33 are each independently hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group.

10. The condensed cyclic compound of claim 1 , wherein

at least one of X 3 , X 6 , X 13 , and X 16 is C(CN).

11. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound represented by Formula 1 is represented by one of Formulae 1-1 and 1-2:

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

descriptions of X 1 to X 8 , X 11 to X 18 , Y 11 , and A 11 are the same as provided in connection with Formula 1; and

descriptions of A 12a , A 12b , and A 12c are the same as provided in connection with A 12 in Formula 1.

12. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound represented by Formula 1 is represented by one of Formulae 1-3 to 1-6:

wherein, in Formulae 1-3 to 1-6,

descriptions of X 1 to X 8 , X 11 to X 18 , Y 11 , R 101 , R 102 , and A 11 are the same as provided in connection with Formula 1;

A 12a , A 12b , and A 12c are the same as provided in connection with A 12 in Formula 1; and

13. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound represented by Formula 1 is represented by one of Formulae 1-11 to 1-25:

wherein, in Formulae 1-11 to 1-25,

X 1 , X 2 , X 4 , X 5 , X 7 , X 8 , X 11 , X 12 , X 14 , X 15 , X 17 , X 18 , Y 11 , and Z 11 to Z 14 are the same as in Formula 1.

14. The condensed cyclic compound of claim 13 , wherein

the condensed cyclic compound represented by Formula 1 is represented by one of Formulae 1-11 to 1-25; and

X 1 is N, X 2 is C(R 2 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is N, X 4 is C(R 4 ), X 5 is C(R 5 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 4 is N, X 5 is C(R 5 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 4 is C(R 4 ), X 5 is N, X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 17 is C(R 17 ), and X 18 is C(R 18 );

X 1 is C(R 1 ), X 2 is C(R 2 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 7 is N, X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 17 is C(R 17 ), and X 18 is C(R 18 ); or

X 1 is C(R 1 ), X 2 is C(R 2 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 7 is C(R 7 ), X 8 is N, X 11 is C(R 11 ), X 12 is C(R 12 ), X 14 is C(R 14 ), X 15 is C(R 15 ), X 17 is C(R 17 ), and X 18 is C(R 18 ).

15. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound represented by Formula 1 is represented by one of Formulae 1-31 to 1-45:

wherein, in Formulae 1-31 to 1-45,

X 1 , X 2 , X 4 , X 5 , X 7 , X 8 , X 11 , X 12 , X 14 , X 15 , X 17 , X 18 , and Z 11 to Z 14 are the same as in Formula 1; and

R 81 to R 88 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 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 31 to Q 33 are each independently selected from hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group.

16. The condensed cyclic compound of claim 15 , wherein

the condensed cyclic compound represented by Formula 1 is represented by one of Formulae 1-31 to 1-45; and

17. The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound represented by Formula 1 is selected from Compounds 1 to 134:

18. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer and at least one condensed cyclic compound represented by Formula 1 of claim 1 .

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

the emission layer comprises the at least one condensed cyclic compound.

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

the emission layer further comprises a phosphorescent dopant.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2019

From: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

Reel/Frame 051366/0480 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2015

From: JEON, SOONOK; KIM, SANGMO; KIM, HYUNJUNG; CHUNG, YEONSOOK; JUNG, YONGSIK; CHAE, MINOUNG; HUH, DALHO; KIM, JONGSOO; SIM, MYUNGSUN

To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

Reel/Frame 037250/0072 →

Priority Claims (1)

KR 10-2015-0105302 · Jul 24, 2015 · national

Continuity (1)

Related Publication 20170025620A1 · Jan 26, 2017