IP Library Patent Application 15258544
Patent Application
App. No. 15/258,544

CONDENSED CYCLIC COMOPUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

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Patent No.
US None
App. No.
15/258,544
Abstract

A condensed cyclic compound represented by Formula 1: Ar 1 -L 1 -L 2 -Ar 2   Formula 1 wherein Ar 1 , Ar 2 , L 1 , and L 2 are the same as described in the specification.

Claims (111)

1 . A condensed cyclic compound represented by Formula 1:

in Formulae 1 to 5,

Ar 1 is a group represented by Formula 2,

Ar 2 is a group represented by Formula 3,

CY 1 is selected from a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group,

CY 2 and CY 3 are each independently selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group,

L 1 and L 2 are each independently a group represented by Formula 4 or a group represented by Formula 5, and at least one of L 1 and L 2 is selected from groups represented by Formula 4,

CY 4 and CY 5 are each independently selected from C 5 -C 30 carbocyclic groups,

R 1 to R 4 , R 10 , R 20 and R 30 are each independently selected from a hydrogen, a deuterium, 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 1 -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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),

R 40 and R 50 are each independently selected from a hydrogen, a deuterium, 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 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 1 -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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),

a1 to a5 are each independently an integer of 0 to 10,

each of * and *′ is a binding site to a neighboring atom,

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 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -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 7 -C 60 arylalkyl group, substituted C 1 -C 60 heteroaryl group, substituted C 2 -C 60 heteroaryloxy group, substituted C 2 -C 60 heteroarylthio group, substituted C 3 -C 60 heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

a deuterium, —CD 3 , —CD 2 H, —CDH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group and a C 1 -C 60 alkoxy group, each substituted with at least one selected from a deuterium, —CD 3 , —CD 2 H, —CDH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 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 C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryloxy group, a C 2 -C 60 heteroarylthio group, a C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 14 )(Q 15 ) and —B(Q 16 )(Q 17 );

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 C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryloxy group, a C 2 -C 60 heteroarylthio group, a C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic 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 C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryloxy group, a C 2 -C 60 heteroarylthio group, a C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —CD 3 , —CD 2 H, —CDH 2 , 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 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 C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryloxy group, a C 2 -C 60 heteroarylthio group, a C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 24 )(Q 25 ) and —B(Q 26 )(Q 27 ); and

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 34 )(Q 35 ) and —B(Q 36 )(Q 37 ), and

Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 and Q 31 to Q 37 are each independently selected from a hydrogen, a deuterium, 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 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 1 -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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2 . The condensed cyclic compound of claim 1 , wherein

Ar 1 is selected from groups represented by Formulae 2-1 to 2-6, and

Ar 2 is selected from groups represented by Formulae 3-1 to 3-7:

in Formulae 2-1 to 2-6 and 3-1 to 3-7,

X 1 is C(R 17 )(R 18 ), N(R 19 ), O or S,

X 2 is C(R 27 )(R 28 ), N(R 29 ), O or S,

R 1 to R 4 , R 11 to R 19 , R 21 to R 29 and R 31 to R 34 are each independently selected from

a hydrogen, a deuterium, 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, 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 phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheplenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anlhracenyl group, a fluoranlhenyl 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 qumazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl 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, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopynmidinyl group, an imidazopyridinyl group, a pyridomdolyl group, a benzofuropyndinyl group, a benzolhienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group and a pyridobenzothiazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cyctoheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 Iriphenylenyl 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 carbazolyl 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, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group and a pyridobenzothiazinyl group, each substituted with at least one selected from a deuterium, 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 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 biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl 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, —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 34 )(Q 35 ) and —B(Q 36 )(Q 37 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),

wherein Q 1 to Q 7 and Q 31 to Q 37 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, and

* is a binding site to a neighboring atom.

3 . The condensed cyclic compound of claim 2 , wherein

R 1 to R 4 , R 11 to R 19 , R 21 to R 29 and R 31 to R 34 are each independently selected from

a hydrogen, a deuterium, a cyano group (CN), 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, a cyano group (CN), a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), and

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

4 . The condensed cyclic compound of claim 2 , wherein

X 1 is O or S.

5 . The condensed cyclic compound of claim 1 , wherein

Ar 1 is the same as Ar 2 in Formula 1; or

CY 2 and CY 3 in Formula 3 are each independently a benzene group.

6 . The condensed cyclic compound of claim 2 , wherein

Ar 1 is represented by Formula 2-1, and Ar 2 is represented by Formula 3-1;

Ar 1 is represented by Formula 2-2, and Ar 2 is represented by Formula 3-2; or

Ar 1 is represented by Formula 2-6, and Ar 2 is represented by Formula 3-6.

7 . The condensed cyclic compound of claim 1 , wherein

L 1 is the same as L 2 .

8 . The condensed cyclic compound of claim 1 , wherein

CY 4 and CY 5 are each independently selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

9 . The condensed cyclic compound of claim 1 , wherein

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

in Formulae 1-1 to 1-3,

Ar 1 and Ar 2 are the same as in claim 1 ,

R 41 to R 48 are each independently the same as R 40 in claim 1 , and

R 51 to R 54 are each independently the same as R 50 in claim 1 .

10 . The condensed cyclic compound of claim 9 , wherein

the condensed cyclic compound is represented by Formula 1-1.

11 . The condensed cyclic compound of claim 9 , wherein

R 41 to R 48 and R 51 to R 54 are each independently selected from

a hydrogen, a deuterium, 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, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ), and

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

12 . The condensed cyclic compound of claim 9 , wherein

Ar 1 is selected from groups represented by Formulae 2-1 to 2-6,

Ar 2 is selected from groups represented by Formulae 3-1 to 3-7:

in Formulae 2-1 to 2-6 and 3-1 to 3-7,

X 1 is C(R 17 )(R 18 ), N(R 19 ), O or S,

X 2 is C(R 27 )(R 28 ), N(R 29 ), O or S,

R 1 to R 4 , R 11 to R 19 , R 21 to R 29 and R 31 to R 34 are each independently selected from

a hydrogen, a deuterium, a cyano group (CN), 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, a cyano group (CN), a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q 31 )(Q 32 )(Q 33 ); and

—Si(Q 1 )(Q 2 )(Q 3 ),

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

13 . The condensed cyclic compound of claim 12 , wherein

the condensed cyclic compound is represented by Formula 1-1, and

X 1 in Formulae 2-1 to 2-6 is O or S.

14 . The condensed cyclic compound of claim 1 , wherein

the condensed cyclic compound is selected from Compounds 1 to 108:

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 and comprising an emission layer,

wherein the organic layer comprises one or more of the condensed cyclic compounds 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; and

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 a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof; and

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

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

the emission layer comprises the condensed cyclic compound represented by Formula 1.

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

the emission layer comprises a host and a dopant,

the host comprises the condensed cyclic compound represented by Formula 1, and

an amount of the host is greater than an amount of the dopant.

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

the hole transport region comprises a hole transport layer, and

the hole transport layer comprises the condensed cyclic compound represented by Formula 1.

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

the hole transport region comprises the electron blocking layer, and

the electron blocking layer comprises the condensed cyclic compound represented by Formula 1.

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 Sep 8, 2016
From: KIM, SANGMO; KIM, HYUNJUNG; JEON, SOONOK; CHUNG, YEONSOOK; CHAE, MIYOUNG; HUH, DALHO; KWON, EUNSUK; KIM, JONGSOO; SIM, MYUNGSUN
To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 039674/0356 →