IP Library Granted Patent US 10,043,984
Granted Patent B2
US 10,043,984 · App. 14/969,257 · 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); Hyungjun Kim (Suwon-si, KR); Yeonsook Chung (Seoul, KR); Yongsik Jung (Yongin-si, KR); Miyoung Chae (Suwon-si, KR); Dalho Huh (Suwon-si, KR); Joonghyuk Kim (Seoul, KR); Sooghang Ihn (Hwaseong-si, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
H01L51/0072C07D401/10C09K11/025C09K11/06H01L51/0061C09K2211/1007C09K2211/1022C09K2211/1044C09K2211/185H01L51/0085H01L51/0087H01L51/5004H01L51/5016H01L2251/552
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Quick Facts
Patent No.
US 10,043,984
App. No.
14/969,257
Granted
Aug 7, 2018
Kind
B2
Abstract

A condensed cyclic compound represented by Formula 1, comprising at least one cyano (—CN) group: wherein, in Formula 1, groups and variables are the same as described in the specification.

Claims (181)

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 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 ),

R 1 to R 8 are independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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, 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 of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

R 11 to R 18 , R 101 , and R 102 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group, and R 101 and R 102 are optionally linked to each other to form a saturated or unsaturated ring,

Ar is a group represented by one of Formulae 2A to 2D:

wherein, in Formulae 2A to 2D,

* and *′ each independently indicate a binding site to a neighboring atom,

X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), and X 24 is N or C(R 24 ), Y 21 is O, S, P(═O) 2 , Se, C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),

R 21 to R 26 each are independently selected from a hydrogen, a deuterium, a C 1 -C 4 alkyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

b21 and b22 each are independently selected from integers of 1 to 3, provided that when b21 is 2 or more, groups R 21 are identical to or different from each other, and provided that when b22 is 2 or more, groups R 22 are identical to or different from each other,

L 11 and L 12 each are independently selected from:

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

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, and a dibenzosilolylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, 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 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 21 )(Q 22 )(Q 23 ),

a11 and a12 each are independently selected from 0, 1, 2, 3, 4, and 5, provided that when a11 is 2 or more, groups L 11 are identical to or different from each other, and provided that when a12 is 2 or more, groups L 12 are identical to or different from each other, and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 each are independently selected from a hydrogen, a C 1 -C 60 alkyl 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, provided that the monovalent non-aromatic condensed heteropolycyclic group does not comprise a carbazolyl group,

wherein the condensed cyclic compound represented by Formula 1 comprises at least one cyano (—CN) group.

2. The condensed cyclic compound of claim 1 , wherein at least one of a group represented by

and a group represented by

comprises at least one cyano (—CN) group.

3. 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 18 ),

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 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 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 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 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 ).

4. The condensed cyclic compound of claim 1 , wherein R 11 to R 18 , R 101 , and R 102 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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, 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 of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, and —Si(Q 31 ) (Q 32 ) (Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

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

Q 1 to Q 3 and Q 31 to Q 33 each are independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group.

5. The condensed cyclic compound of claim 1 , wherein R 1 to R 8 , R 11 to R 18 , R 101 , and R 102 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl 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 naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl 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 naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 1 )(Q 2 )(Q 3 ),

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

Q 1 to Q 3 each are independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a phenyl group.

6. The condensed cyclic compound of claim 1 , wherein R 1 to R 8 and R 11 to R 18 each are independently selected from a hydrogen, a deuterium, a cyano (—CN) group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, and —Si(Q 1 )(Q 2 )(Q 3 ), and

Q 1 to Q 3 each are independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a phenyl group.

7. The condensed cyclic compound of claim 1 , wherein R 101 and R 102 each are independently selected from:

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group, each substituted with a cyano (—CN) group.

8. The condensed cyclic compound of claim 1 , wherein Ar is a group represented by one of Formulae 2-1 to 2-28:

wherein, in Formulae 2-1 to 2-28,

Y 21 is O or S,

R 21 to R 24 each are independently selected from a hydrogen, a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

Q 11 to Q 13 each are independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a phenyl group,

b21 and b22 each are independently selected from 1, 2, and 3, and

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

9. The condensed cyclic compound of claim 1 , wherein *-(L 11 ) a11 -Ar-(L 12 ) a12 -* is a group represented by one of Formulae 4-1 to 4-19:

wherein, in Formulae 4-1 to 4-19,

Y 21 is O or S,

R 21 to R 24 and R 31 each are independently selected from a hydrogen, a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 21 )(Q 22 )(Q 23 ),

Q 21 to Q 23 each are independently selected from a hydrogen, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a phenyl group,

b21 and b22 each are independently selected from 1, 2, and 3,

b31 is selected from 1, 2, 3, and 4, and

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

10. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is represented by one of Formulae 1-1 to 1-15:

wherein, in Formulae 1-1 to 1-15,

X 1 , X 2 , X 4 , X 5 , X 7 , X 8 , X 11 , X 12 , X 14 , X 15 , X 17 , X 17 , Y 11 , Ar, L 11 , L 12 , a11, and a12 are as defined in Formula 1.

11. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is selected from Compounds 1 to 103:

12. 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 the condensed cyclic compound of Formula 1 of claim 1 .

13. The organic light-emitting device of claim 12 , wherein the emission layer comprises the condensed cyclic compound of Formula 1.

14. The organic light-emitting device of claim 13 , wherein the emission layer further comprises a phosphorescent dopant.

15. The condensed cyclic compound of claim 1 , at least one of X 1 to X 8 in Formula 1 is C(CN); at least one of X 11 to X 18 in Formula 1 is C(CN); or Y 11 in Formula 1 is a group including a cyano (—CN) group.

16. 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 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 C(R 101 )(R 102 ) or Si(R 101 )(R 102 ),

R 1 to R 8 , R 11 to R 18 , R 101 , and R 102 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group,

wherein R 101 and R 102 are linked to each other to form a compound represented by Formula 8:

wherein, in Formula 8,

* indicates a carbon atom comprised in Y 11 of 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 ),

R 81 to R 88 each are independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 ), and

Q 31 to Q 33 each are 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, and a triazinyl group,

wherein, in Formula 1,

Ar is a group represented by one of Formulae 2A to 2D:

wherein, in Formulae 2A to 2D,

* and *′ each independently indicate a binding site to a neighboring atom,

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

Y 21 is O, S, P(═O) 2 , Se, C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),

R 21 to R 26 each are independently selected from a hydrogen, a deuterium, a C 1 -C 4 alkyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

b21 and b22 each are independently selected from integers of 1 to 3, provided that when b21 is 2 or more, groups R 21 are identical to or different from each other, and provided that when b22 is 2 or more, groups R 22 are identical to or different from each other,

L 11 and L 12 each are independently selected from:

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

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, and a dibenzosilolylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, 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 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 21 )(Q 22 )(Q 23 ),

a11 and a12 each are independently selected from 0, 1, 2, 3, 4, and 5, provided that when a11 is 2 or more, groups L 11 are identical to or different from each other, and provided that when a12 is 2 or more, groups L 12 are identical to or different from each other, and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 each are independently selected from a hydrogen, a C 1 -C 60 alkyl 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, provided that the monovalent non-aromatic condensed heteropolycyclic group does not comprise a carbazolyl group,

wherein the condensed cyclic compound represented by Formula 1 comprises at least one cyano (—CN) group.

17. 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 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 C(R 101 )(R 102 ) or Si(R 101 )(R 102 ),

R 1 to R 8 , R 11 to R 18 , R 101 , and R 102 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group,

wherein at least one of a 11 and a 12 is not 0, and L 11 and L 12 each are independently selected from:

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene 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 dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, 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 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 21 )(Q 22 )(Q 23 ),

wherein, in Formula 1,

Ar is a group represented by one of Formulae 2A to 2D:

wherein, in Formulae 2A to 2D,

* and *′ each independently indicate a binding site to a neighboring atom,

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

Y 21 is O, S, P(═O) 2 , Se, C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),

R 21 to R 26 each are independently selected from a hydrogen, a deuterium, a C 1 -C 4 alkyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

b21 and b22 each are independently selected from integers of 1 to 3, provided that when b21 is 2 or more, groups R 21 are identical to or different from each other, and provided that when b22 is 2 or more, groups R 22 are identical to or different from each other,

L 11 and L 12 each are independently selected from:

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

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, and a dibenzosilolylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, 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 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 21 )(Q 22 )(Q 23 ),

a11 and a12 each are independently selected from 0, 1, 2, 3, 4, and 5, provided that when a11 is 2 or more, groups L 11 are identical to or different from each other, and provided that when a12 is 2 or more, groups L 12 are identical to or different from each other, and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 each are independently selected from a hydrogen, a C 1 -C 60 alkyl 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, provided that the monovalent non-aromatic condensed heteropolycyclic group does not comprise a carbazolyl group,

wherein the condensed cyclic compound represented by Formula 1 comprises at least one cyano (—CN) group.

18. The condensed cyclic compound of claim 17 , wherein at least one of a 11 and a 12 is not 0, and L 11 and L 12 each are independently selected from:

a phenylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and

a phenylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group, each substituted with at least one of a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 21 )(Q 22 )(Q 23 ).

19. A condensed cyclic compound represented by one of Formulae 1-21 to 1-47:

wherein, in Formulae 1-21 to 1-47,

X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 4 is N or C(R 4 ), X 5 is N or C(R 5 ), 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 14 is N or C(R 14 ), X 15 is N or C(R 15 ), X 17 is N or C(R 17 ), and X 18 is N or C(R 18 ),

R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 11 , R 12 , R 14 , R 15 , R 17 , R 18 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group,

Ar is a group represented by one of Formulae 2A to 2D:

wherein, in Formulae 2A to 2D,

* and *′ each independently indicate a binding site to a neighboring atom,

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

Y 21 is O, S, P(═O) 2 , Se, C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),

R 21 to R 26 each are independently selected from a hydrogen, a deuterium, a C 1 -C 4 alkyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

b21 and b22 each are independently selected from integers of 1 to 3, provided that when b21 is 2 or more, groups R 21 are identical to or different from each other, and provided that when b22 is 2 or more, groups R 22 are identical to or different from each other,

L 11 and L 12 each are independently selected from:

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

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, and a dibenzosilolylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, 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 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 21 )(Q 22 )(Q 23 ),

a11 and a12 each are independently selected from 0, 1, 2, 3, 4, and 5, provided that when a11 is 2 or more, groups L 11 are identical to or different from each other, and provided that when a12 is 2 or more, groups L 12 are identical to or different from each other, and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 each are independently selected from a hydrogen, a C 1 -C 60 alkyl 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, provided that the monovalent non-aromatic condensed heteropolycyclic group does not comprise a carbazolyl group,

wherein the condensed cyclic compound represented by one of Formulae 1-44 comprises at least one cyano (—CN) group,

R 81 to R 88 each are independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 ),

Q 31 to Q 33 each are 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, and a triazinyl group, and

R 101 and R 102 each are independently selected from:

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group; and

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group, each substituted with a cyano (—CN) group.

20. 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 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 C(R 101 )(R 102 ) or Si(R 101 )(R 102 ),

R 11 to R 18 , R 101 , and R 102 each are independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group,

R 1 to R 8 each are independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group,

wherein 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 6 arylthio group, the substituted C 2 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 1 -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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 31 )(Q 32 )(Q 33 ), 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 a hydrogen, 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 1 -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,

wherein, in Formula 1,

Ar is a group represented by one of Formulae 2A to 2D:

wherein, in Formulae 2A to 2D,

* and *′ each independently indicate a binding site to a neighboring atom,

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

Y 21 is O, S, P(═O) 2 , Se, C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),

R 21 to R 26 each are independently selected from a hydrogen, a deuterium, a C 1 -C 4 alkyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, and —Si(Q 11 )(Q 12 )(Q 13 ),

b21 and b22 each are independently selected from integers of 1 to 3, provided that when b21 is 2 or more, groups R 21 are identical to or different from each other, and provided that when b22 is 2 or more, groups R 22 are identical to or different from each other,

L 11 and L 12 each are independently selected from:

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

a phenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, and a dibenzosilolylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, 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 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 21 )(Q 22 )(Q 23 ),

a11 and a12 each are independently selected from 0, 1, 2, 3, 4, and 5, provided that when a11 is 2 or more, groups L 11 are identical to or different from each other, and provided that when a12 is 2 or more, groups L 12 are identical to or different from each other, and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 each are independently selected from a hydrogen, a C 1 -C 60 alkyl 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, provided that the monovalent non-aromatic condensed heteropolycyclic group does not comprise a carbazolyl group,

wherein the condensed cyclic compound represented by Formula 1 comprises at least one cyano (—CN) group.

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 15, 2015
From: JEON, SOONOK; KIM, SANGMO; KIM, HYUNJUNG; CHUNG, YEONGSOOK; JUNG, YONGSIK; CHAE, MIYOUNG; HUH, DALHO; KIM, JOONGHYUK; IHN, SOOGHANG
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 037292/0914 →
Priority Claims (2)
KR 10-2015-0094004 · Jul 1, 2015 · national
KR 10-2015-0115420 · Aug 17, 2015 · national
Continuity (1)
Related Publication 20170005275A1 · Jan 5, 2017