IP Library Granted Patent US 10,062,852
Granted Patent B2
US 10,062,852 · App. 15/145,158 · Granted Aug 28, 2018

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

Inventors: Hyunjung Kim (Suwon-si, KR); Miyoung Chae (Suwon-si, KR); Sangmo Kim (Hwaseong-si, KR); Soonok Jeon (Seoul, KR); Yeonsook Chung (Seoul, KR); Yongsik Jung (Yongin-si, KR); Dalho Huh (Suwon-si, KR); Youngmok Son (Hwaseong-si, KR); Namheon Lee (Suwon-si, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
H01L51/0072C07D209/86C07D403/10C09K11/02C09K11/06H01L51/008H01L51/009H01L51/0085C09K2211/1007C09K2211/1022C09K2211/1029C09K2211/1044C09K2211/185H01L51/0061H01L51/5004H01L51/5012H01L51/5016H01L51/5028H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096H01L51/5206H01L51/5221H01L2251/552
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 10,062,852
App. No.
15/145,158
Granted
Aug 28, 2018
Kind
B2
Abstract

A condensed cyclic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.

Claims (124)

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 5 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, C(R 15 ), or a carbon atom connected to *-(L 1 ) a1 -*′, X 16 is N, C(R 16 ), or a carbon atom connected to *-(L 1 ) a1 -*′, X 17 is N, C(R 17 ), or a carbon atom connected to *-(L 1 ) a1 -*′, and X 18 is N, C(R 18 ), or a carbon atom connected to *-(L 1 ) a1 -*′, wherein one of X 15 to X 18 is connected to *-(L 1 ) a1 -*′,

ring A 1 is selected from a C 5 -C 60 carbocyclic group and a C 3 -C 60 heterocyclic group comprising at least one heteroatom selected from O, S, and Si,

L 1 is selected from

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene 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, 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, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

L 2 is selected from

a phenylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene 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, 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 fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

a1 and a2 are each independently an integer selected from 0 to 5, wherein when a1 is 2 or greater, two or more groups L 1 are identical to or different from each other, and when a2 is 2 or greater, two or more groups L 2 are identical to or different from each other,

R 1 to R 8 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, 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 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 1 -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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 1 )(Q 2 )(Q 3 ),

R 11 to R 15 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group (—CN), a nitro group, an amino group, an amindino 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 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 1 -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 —Si(Q 1 )(Q 2 )(Q 3 ),

R 31 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, 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 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 1 -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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 1 )(Q 2 )(Q 3 ),

b1 is an integer selected from 0 to 4,

c1 is an integer selected from 1 to 4,

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 1 -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, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from a deuterium, —F, —Cl, —Br, 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 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 21 )(Q 22 )(Q 23 ),

wherein Q 1 to Q 3 , Q 11 to Q 13 , and Q 21 to Q 23 are each independently selected from a hydrogen, a deuterium, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group

in *-(L 1 ) a1 -*′, * and *′ are each a binding site to a neighboring atom.

2. The condensed cyclic compound of claim 1 , wherein ring A 1 is selected from a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a benzene ring, a pentalene ring, an indene ring, a naphthene ring, an azulene ring, a heptalene ring, an indacene ring, an acenaphthene ring, a fluorene ring, a spirobifluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a naphthacene ring, a picene ring, a perylene ring, a pentaphene ring, a hexacene ring, a furane ring, a thiophene ring, a benzofurane ring, a benzothiophene ring, a dibenzofurane ring, and a dibenzothiophene ring.

3. The condensed cyclic compound of claim 1 , wherein ring A 1 is selected from a benzene ring, a dibenzofurane ring, and a dibenzothiophene ring.

4. The condensed cyclic compound of claim 1 , wherein L 1 is selected from groups represented by Formulae 3-1 to 3-56, and L 2 is selected from groups represented by Formulae 3-1, 3-15, 3-28, and 3-41 to 3-56:

wherein, in Formulae 3-1 to 3-56,

Y 1 is selected from O, S, and C(Z 3 )(Z 4 ),

Z 1 to Z 4 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 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, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently selected from a 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, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

d4 is an integer selected from 0 to 4,

d3 is an integer selected from 0 to 3,

d2 is an integer selected from 0 to 2, and

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

5. The condensed cyclic compound of claim 4 , wherein

i) a1 is 0; or

ii) when a1 is not 0, at least one of groups L 1 is selected from groups represented by Formulae 3-15 to 3-56.

6. The condensed cyclic compound of claim 4 , wherein

L 1 is selected from groups represented by Formulae 3-15, 3-28, 3-41, and 3-51,

L 2 is selected from groups represented by Formulae 3-1, 3-15, 3-28, 3-41, and 3-51, and

a1 and a2 are each independently 0, 1, or 2.

7. The condensed cyclic compound of claim 1 , wherein a group represented by *-(L 1 ) a1 -*′ is selected from groups represented by Formulae 4-1 to 4-39:

wherein, in Formulae 4-1 to 4-39,

X 21 is N or C(Z 21 ), X 22 is N or C(Z 22 ), X 23 is N or C(Z 23 ), X 24 is N or C(Z 24 ), X 31 is N or C(Z 31 ), X 32 is N or C(Z 32 ), X 33 is N or C(Z 33 ), X 34 is N or C(Z 34 ), X 41 is N or C(Z 41 ), X 42 is N or C(Z 42 ), X 43 is N or C(Z 43 ), and X 44 is N or C(Z 44 ), provided that at least one of X 21 to X 24 is not N, provided that at least one of X 31 to X 34 is not N, and provided that at least one of X 41 to X 44 is not N,

Z 21 to Z 24 , Z 31 to Z 34 , and Z 41 to Z 44 are each independently selected from a hydrogen, a deuterium, a cyano group, 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, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently a 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, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and

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

8. The condensed cyclic compound of claim 1 , wherein

R 1 to R 8 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 10 alkoxy group;

a C 1 -C 10 alkoxy group 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, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl 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, 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, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

wherein Q 1 to Q 3 and Q 21 to Q 23 are each independently selected from a 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, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and

R 11 to R 18 , and R 31 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 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, and a C 1 -C 10 alkoxy group;

a C 1 -C 10 alkyl group and a C 1 -C 10 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 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 naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl 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, 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, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

wherein Q 1 to Q 3 and Q 21 to Q 23 are each independently selected from a 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, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

9. The condensed cyclic compound of claim 1 , wherein

R 1 to R 8 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, and a C 1 -C 10 alkoxy group:

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

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ) g; and

—Si(Q 1 )(Q 2 )(Q 3 ),

R 11 to R 18 , and R 31 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group,

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

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

Q 1 to Q 3 and Q 21 to Q 23 are each independently a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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 a group represented by

is selected from groups represented by Formulae 5-1 to 5-60:

wherein, in Formulae 5-1 to 5-60, * is a binding site to a neighboring atom.

12. The condensed cyclic compound of claim 1 , represented by one of Formulae 1A to 1D:

wherein, in Formulae 1A to 1D,

ring A 1 is independently selected from a benzene ring, a dibenzofurane ring, and a dibenzothiophene ring,

L 1 is selected from groups represented by Formulae 3-15, 3-28, 3-41, and 3-51,

L 2 is selected from groups represented by Formulae 3-1, 3-15, 3-28, 3-41, and 3-51,

a1 and a2 are each independently selected from 0, 1, and 2,

R 1 to R 8 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, and a C 1 -C 10 alkoxy group;

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

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

wherein Q 1 to Q 3 and Q 21 to Q 23 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

R 11 to R 18 , and R 31 are each independently selected from

a hydrogen, a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkoxy group;

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

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

wherein Q 1 to Q 3 and Q 21 to Q 23 are each independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

b1 is 0 or 1, and

c1 is 1 or 2:

wherein, in Formulae 3-41 and 3-51,

Y 1 is selected from O, S, and C(Z 3 )(Z 4 ),

wherein, in Formulae 3-1, 3-15, 3-28, 3-41, and 3-51,

Z 1 to Z 4 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 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, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

wherein Q 11 to Q 13 are each independently selected from a 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, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

d4 is an integer selected from 0 to 4,

d3 is an integer selected from 0 to 3, and

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

13. The condensed cyclic compound of claim 12 , wherein a group represented by

is selected from groups represented by Formulae 5-1 to 5-3, 5-31, 5-39, 5-47, and 5-55:

14. The condensed cyclic compound of claim 1 , represented by one of Compounds 1 to 336:

15. 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 .

16. The organic light-emitting device of claim 15 , wherein

the first electrode is an anode,

the second electrode is a cathode,

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

wherein the hole transport region comprises at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and

wherein the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

17. The organic light-emitting device of claim 15 , wherein the emission layer comprises the at least one condensed cyclic compound represented by Formula 1.

18. The organic light-emitting device of claim 15 , wherein the emission layer comprises the at least one condensed cyclic compound represented by Formula 1, wherein the emission layer further comprises a phosphorescent dopant, and wherein an amount of the at least one condensed cyclic compound is larger than an amount of the phosphorescent dopant.

19. The organic light-emitting device of claim 17 , wherein the emission layer emits blue light.

20. The organic light-emitting device of claim 15 , wherein the emission layer comprises the condensed cyclic compound represented by Formula 1, and wherein the condensed cyclic compound represented by Formula 1 is a thermally activated delayed fluorescence emitter.

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 May 11, 2016
From: KIM, HYUNJUNG; CHAE, MIYOUNG; KIM, SANGMO; JEON, SOONOK; CHUNG, YEONSOOK; JUNG, YONGSIK; HUH, DALHO; SON, YOUNGMOK; LEE, NAMHEON
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 038547/0852 →
Priority Claims (2)
KR 10-2015-0089088 · Jun 23, 2015 · national
KR 10-2016-0039619 · Mar 31, 2016 · national
Continuity (1)
Related Publication 20160380210A1 · Dec 29, 2016
Cited By (1)
US 12,570,636