EP-4742867-A1 - HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS
Abstract
Provided are a heterocyclic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus: Descriptions of the substituents in Formula 1 are as provided herein.
Inventors
- LEE, Halim
- CHO, Hwayoung
- CHWAE, JUN
- KIM, SANGMO
- KIM, HWANG SUK
- LEE, EUNKYUNG
- KIM, RAESUNG
- KIM, JIWHAN
- NAM, SUNGHO
- LEE, YEONKYUNG
- JEONG, Daun
Assignees
- Samsung Electronics Co., Ltd.
Dates
- Publication Date
- 20260513
- Application Date
- 20251030
Claims (15)
- A heterocyclic compound represented by Formula 1: wherein, in Formula 1, Y 11 and Y 12 are each independently a single bond, O, S, Se, N(Ar 3 ), N(R 1 ), C(R 1 )(R 2 ), Si(R 1 )(R 2 ), Ge(R 1 )(R 2 ), B(R 1 ), P(R 1 ), P(=O)(R 1 ), S(=O) 2 , or C(=O), Y 21 and Y 22 are each independently a single bond, O, S, Se, N(Ar 4 ), N(R 3 ), C(R 3 )(R 4 ), Si(R 3 )(R 4 ), Ge(R 3 )(R 4 ), B(R 3 ), P(R 3 ), P(=O)(R 3 ), S(=O) 2 , or C(=O), Ar 1 to Ar 4 are each independently a group represented by Formula 2, wherein, in Formulae 1 and 2, CY 11 to CY 13 , CY 21 to CY 23 , and CY 3 to CY 6 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, indicates a single bond or a double bond, * indicates a binding site to a neighboring atom, R 1 to R 4 , R 10 , R 20 , R 30 , R 40 , R 50 and R 60 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono 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 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 ), -Si(Q 1 )(Q 2 )(Q 3 ), -Ge(Q 1 )(Q 2 )(Q 3 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), - S(=O) 2 (Q 1 ), -B(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -P(=O)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ), b11 to b13, b21 to b23, b30, b40, b50, and b60 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, two or more of adjacent R 1 to R 4 , R 10 , R 20 , R 30 , R 40 , R 50 , and R 60 are optionally bonded to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, substituents of the substituted C 5 -C 30 carbocyclic group, the substituted C 1 -C 30 heterocyclic group, 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 1 -C 60 alkylthio group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 7 -C 60 alkyl aryl group, the substituted C 7 -C 60 aryl alkyl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 2 -C 60 alkyl heteroaryl group, the substituted C 2 -C 60 heteroaryl alkyl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are: deuterium, -F, -Cl, -Br, -I, -SF 5 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 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, C 1 -C 60 alkylthio group, or 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, C 1 -C 60 alkylthio group, or a C 1 -C 60 alkoxy group, each substituted with deuterium, -F, -Cl, -Br, -I, -SF 5 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 11 )(Q 12 )(Q 13 ), -Ge(Q 11 )(Q 12 )(Q 13 ), -C(=O)(Q 11 ), -S(=O)(Q 11 ), -S(=O) 2 (Q 11 ) , -B(Q 11 )(Q 12 ) , -P(Q 11 )(Q 12 ) , -P(=O)(Q 11 )(Q 12 ) , - P(=S)(Q 11 )(Q 12 ), or a combination 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -SF 5 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, - CFH 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, C 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 21 )(Q 22 )(Q 23 ), - Ge(Q 21 )(Q 22 )(Q 23 ) , -C(=O)(Q 21 ), -S(=O)(Q 21 ) , -S(=O) 2 (Q 21 ) , -B(Q 21 )(Q 22 ) , -P(Q 21 )(Q 22 ) , -P(=O)(Q 21 )(Q 22 ), -P(=S)(Q 21 )(Q 22 ), or a combination thereof; -N(Q 31 )(Q 32 ), -Si(Q 31 )(Q 32 )(Q 33 ), -Ge(Q 31 )(Q 32 )(Q 33 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O) 2 (Q 31 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -P(=O)(Q 31 )(Q 32 ), or -P(=S)(Q 31 )(Q 32 ); or a combination thereof, and Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently: hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , 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, C 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; or 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, C 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.
- The heterocyclic compound of claim 1, wherein Y 11 and Y 21 are each independently O, S, or Se, and Y 12 and Y 22 are each independently O, S, Se, N(Ar 3 ), N(R 1 ), C(R 1 )(R 2 ), or Si(R 1 )(R 2 ).
- The heterocyclic compound of claims 1 or 2, wherein CY 11 to CY 13 , CY 21 to CY 23 , and CY 3 to CY 6 are each independently a benzene group, a naphthalene group, a phenanthrene group, a fluorene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene 5,5-dioxide group.
- The heterocyclic compound of any of claims 1-3, wherein the group represented by Formula 2 is a group represented by Formula 2A: wherein, in Formula 2A, X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, and X 43 is C(R 43 ) or N, X 51 is C(R 51 ) or N, X 52 is C(R 52 ) or N, X 53 is C(R 53 ) or N, X 54 is C(R 54 ) or N, X 55 is C(R 55 ) or N, X 61 is C(R 61 ) or N, X 62 is C(R 62 ) or N, X 63 is C(R 63 ) or N, X 64 is C(R 64 ) or N, X 65 is C(R 65 ) or N, R 41 to R 43 are each independently as described in connection with R 40 in claim 1, R 51 to R 55 are each independently as described in connection with R 50 in claim 1, R 61 to R 65 are each independently as described in connection with R 60 in claim 1, and * indicates a binding site to a neighboring atom; preferably wherein the group represented by Formula 2 is a group represented by Formula 2A-1: wherein, in Formula 2A-1, R 41 to R 43 are each independently as described in connection with R 40 in claim 1, R 51 to R 55 are each independently as described in connection with R 50 in claim 1, R 61 to R 65 are each independently as described in connection with R 60 in claim 1, and * indicates a binding site to a neighboring atom.
- The heterocyclic compound of any of claims 1-4, wherein R 1 to R 4 , R 10 , R 20 , R 30 , R 40 , R 50 , and R 60 are each independently: hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , 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, C 1 -C 20 alkylthio group, or a C 1 -C 20 alkoxy group; a C 1 -C 20 alkyl group, C 1 -C 20 alkylthio group, or a C 1 -C 20 alkoxy group, each substituted with deuterium, -F, -Cl, -Br, -I, -SF 5 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, - CFH 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 20 alkyl group, a deuterium-containing C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (a norbornanyl group), a bicyclo[2.2.2]octyl group, a (C 1 -C 20 alkyl)cyclopentyl group, a (C 1 -C 20 alkyl)cyclohexyl group, a (C 1 -C 20 alkyl)cycloheptyl group, a (C 1 -C 20 alkyl)cyclooctyl group, a (C 1 -C 20 alkyl)adamantanyl group, a (C 1 -C 20 alkyl)norbornenyl group, a (C 1 -C 20 alkyl)cyclopentenyl group, a (C 1 -C 20 alkyl)cyclohexenyl group, a (C 1 -C 20 alkyl)cycloheptenyl group, a (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl group, a (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl group, a (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl group, a (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl group, a silolanyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof; a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a silolanyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl 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 imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, -F, - Cl, -Br, -I, -SF 5 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 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 20 alkyl group, a deuterium-containing C 1 -C 20 alkyl group, a fluorine-containing C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C 1 -C 20 alkyl)cyclopentyl group, a (C 1 -C 20 alkyl)cyclohexyl group, a (C 1 -C 20 alkyl)cycloheptyl group, a (C 1 -C 20 alkyl)cyclooctyl group, a (C 1 -C 20 alkyl)adamantanyl group, a (C 1 -C 20 alkyl)norbornenyl group, a (C 1 -C 20 alkyl)cyclopentenyl group, a (C 1 -C 20 alkyl)cyclohexenyl group, a (C 1 -C 20 alkyl)cycloheptenyl group, a (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl group, a (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl group, a (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl group, a (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl group, a silolanyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl 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 imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or a combination thereof; or -N(Q 1 )(Q 2 ), -Si(Q 1 )(Q 2 )(Q 3 ), -Ge(Q 1 )(Q 2 )(Q 3 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), - S(=O) 2 (Q 1 ), -B(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -P(=O)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ).
- The heterocyclic compound of any of claims 1-5, wherein at least one of R 30 in the number of b30 is -F, -Cl, -Br, -I, -SF 5 , a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
- The heterocyclic compound of any of claims 1-6, wherein the heterocyclic compound is a compound represented by Formula 11: wherein, in Formula 11, Y 11 , Y 12 , Y 21 , Y 22 , Ar 1 , and Ar 2 are as in claim 1, X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 15 is C(R 15 ) or N, X 16 is C(R 16 ) or N, X 17 is C(R 17 ) or N, X 18 is C(R 18 ) or N, X 19 is C(R 19 ) or N, X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, X 24 is C(R 24 ) or N, X 25 is C(R 25 ) or N, X 26 is C(R 26 ) or N, X 27 is C(R 27 ) or N, X 28 is C(R 28 ) or N, X 29 is C(R 29 ) or N, X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, R 11 to R 19 are each independently as described in connection with R 10 in claim 1, R 21 to R 29 are each independently as described in connection with R 20 in claim 1, and R 31 to R 33 are each independently as described in connection with R 30 in claim 1; preferably wherein R 32 is -F, -Cl, -Br, -I, -SF 5 , a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and R 31 and R 33 are each independently hydrogen or deuterium.
- The heterocyclic compound of any of claims 1-7, wherein the heterocyclic compound is a compound represented by Formula 21: wherein, in Formula 21, Y 11 , Y 12 , Y 21 , Y 22 , Ar 1 , and Ar 2 are as in claim 1, R 11 to R 19 are each independently as described in connection with R 10 in claim 1, R 21 to R 29 are each independently as described in connection with R 20 in claim 1, and R 31 to R 33 are each independently as described in connection with R 30 in claim 1.
- The heterocyclic compound of any of claims 1-8, wherein the heterocyclic compound is a compound represented by Formula 31: wherein, in Formula 31, Y 11 , Y 12 , Y 21 , and Y 22 are as in claim 1, R 11 to R 19 are each independently as described in connection with R 10 in claim 1, R 21 to R 29 are each independently as described in connection with R 20 in claim 1, and R 31 to R 33 are each independently as described in connection with R 30 in claim 1, R 41 to R 43 and R 41a to R 43a are each independently as described in connection with R 40 in claim 1, R 51 to R 55 and R 51a to R 55a are each independently as described in connection with R 50 in claim 1, and R 61 to R 65 and R 61a to R 65a are each independently as described in connection with R 60 in claim 1.
- The heterocyclic compound of claim 1, wherein the heterocyclic compound is any one of compounds 1 to 510:
- An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer further comprises at least one of the heterocyclic compounds of any of claims 1-10.
- The organic light-emitting device of claim 11, wherein the emission layer comprises the at least one heterocyclic compound.
- The organic light-emitting device of claim 12, wherein the emission layer comprises a host and an emitter, and the emitter comprises the at least one heterocyclic compound; preferably wherein the emission layer emits a blue light with a maximum emission wavelength of 400 nanometers to 490 nanometers.
- The organic light-emitting device of claim 13, wherein an amount of the host in the emission layer is greater than an amount of the at least one heterocyclic compound in the emission layer, based on weight; and/or wherein the emission layer further comprises a sensitizer, preferably wherein the sensitizer comprises a phosphorescent dopant.
- An electronic apparatus, comprising the organic light-emitting device of any of claims 11-14.
Description
FIELD OF THE INVENTION The disclosure relates to a heterocyclic compound, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device. BACKGROUND OF THE INVENTION Organic light-emitting devices (OLEDs) are self-emissive devices that have excellent characteristics in terms of viewing angles, response time, brightness, driving voltage, response speed, and the like, and produce full-color images. Organic light-emitting devices include an anode, a cathode, and an organic layer arranged between the anode and the cathode and including an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. When the excitons transition from an excited state to a ground state, light is emitted. SUMMARY OF THE INVENTION Provided are a heterocyclic compound, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus. Additional aspects will be set forth in part in the detailed description that follows and, in part, will be apparent from the detailed description, or may be learned by practice of the presented exemplary embodiments described herein. According to an aspect, provided is a heterocyclic compound represented by Formula 1: wherein, in Formula 1, Y11 and Y12 are each independently a single bond, O, S, Se, N(Ar3), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(=O)(R1), S(=O)2, or C(=O),Y21 and Y22 are each independently a single bond, O, S, Se, N(Ar4), N(R3), C(R3)(R4), Si(R3)(R4), Ge(R3)(R4), B(R3), P(R3), P(=O)(R3), S(=O)2, or C(=O),Ar1 to Ar4 are each independently a group represented by Formula 2, CY11 to CY13, CY21 to CY23, and CY3 to CY6 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, indicates a single bond or a double bond,* indicates a binding site to a neighboring atom,R1 to R4, R10, R20, R30, R40, R50 and R60 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono 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 C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), - C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -B(Q1)(Q2), -P(Q1)(Q2), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2),b11 to b13, b21 to b23, b30, b40, b50, and b60 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14,two or more adjacent of R1 to R4, R10, R20, R30, R40, R50, and R60 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,substituents of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C7-C60 aryl alkyl group, the substituted C6-C60 aryloxy group