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KR-20260067845-A - HETEROCYCLIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS

KR20260067845AKR 20260067845 AKR20260067845 AKR 20260067845AKR-20260067845-A

Abstract

A heterocyclic compound represented by the following chemical formula 1, an organic light-emitting device including the same, and an electronic device are disclosed: <Chemical Formula 1> Refer to the description of the invention for the description of the substituents of Chemical Formula 1 above.

Inventors

  • 이하림
  • 조화영
  • 최준
  • 김상모
  • 김황석
  • 이은경
  • 김래성
  • 김지환
  • 남성호
  • 이연경
  • 정다운

Assignees

  • 삼성전자주식회사

Dates

Publication Date
20260513
Application Date
20241106

Claims (20)

  1. Heterocyclic compounds represented by the following chemical formula 1: <Chemical Formula 1> Among the above chemical formula 1, Y 11 and Y 12 are independently single bonds, 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), and Y 21 and Y 22 are independently single bonds, 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), and Ar 1 to Ar 4 are independently groups represented by the following chemical formula 2, and <Chemical Formula 2> Among the above chemical formulas 1 and 2, CY 11 to CY 13 , CY 21 to CY 23 and CY 3 to CY 6 are independently C 5 -C 30 carbocyclic groups or substituted or unsubstituted C 1 -C 30 heterocyclic groups, and represents a single bond or a double bond, * is a bonding site with a neighboring atom, and R1 to R4 , R10 , R20 , R30 , R40 , R50 , and R60 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5 , hydroxyl group, cyano group, nitro group, amido group, hydrazino group, hydrazono group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C2 - C60 alkenyl group, substituted or unsubstituted C2 - C60 alkynyl group, substituted or unsubstituted C1 - C60 alkoxy group, substituted or unsubstituted C3 - C10 cycloalkyl group, substituted or unsubstituted C1 - C10 heterocycloalkyl group, substituted or unsubstituted C3 - C10 cycloalkenyl group, substituted or unsubstituted C1 - C10 Heterocycloalkenyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C7 - C60 alkylaryl group, substituted or unsubstituted C6 - C60 aryloxy group, substituted or unsubstituted C6- C60 arylthio group, substituted or unsubstituted C1 - C60 heteroaryl group, substituted or unsubstituted C2 - C60 alkylheteroaryl group, substituted or unsubstituted C1 - C60 heteroaryloxy group, substituted or unsubstituted C1 - C60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N( Q1 )( Q2 ), -Si( Q1 )( Q2 )( Q3 ), -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 ), -P(=S)(Q 1 )(Q 2 ), or -P(=S)(Q 1 )(Q 2 ), b11 to b13, b21 to b23, b30, b40, b50 and b60 are independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, and Two or more adjacent of R1 to R4 , R10 , R20 , R30 , R40 , R50 , and R60 optionally combine to form a substituted or unsubstituted C5 - C30 carbocyclic group or a C1 - C30 heterocyclic group, and The above substituted C5 - C30 carbocyclic group, substituted C1 - C30 heterocyclic group, substituted C1 -C60 alkyl group, substituted C2- C60 alkenyl group, substituted C2 - C60 alkynyl group, substituted C1 - C60 alkoxy group, substituted C3 - C10 cycloalkyl group, substituted C1 - C10 heterocycloalkyl group, substituted C3 - C10 cycloalkenyl group, substituted C1 - C10 heterocycloalkenyl group, substituted C6 - C60 aryl group, substituted C6- C60 aryloxy group, substituted C6 - C60 arylthio group, substituted C1 - C60 heteroaryl group, substituted C1 - C60 heteroaryloxy group, substituted C The 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituents of the substituted monovalent non-aromatic heterocondensed polycyclic group are, Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group or C1 - C60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent A non-aromatic heterocondensed polycyclic group, substituted with -N( Q11 )( Q12 ), -Si( Q11 )( Q12 )( Q13 ), -Ge( Q11 )( Q12)(Q13 ), -C(=O)( Q11 ), -S(=O)( Q11 ) , -S(=O) 2 ( Q11 ), -B( Q11 )( Q12 ), -P(Q11)( Q12 ), -P(=O)( Q11 )( Q12 ), -P(=S)( Q11 )( Q12 ) , or any combination thereof, a C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, or C1 - C60 Alkoxygenation; Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 aryltio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N( Q21 )( Q22 ), -Si( Q21 )( Q22 )( Q23 ), -Ge( Q21 )(Q22)( Q23 ), -C(=O)( Q21 ), -S(=O)( Q21 ), -S(=O) 2 ( Q21 ), -B( Q21 )( Q22 ), -P( Q21 ) (Q22 ) , -P(=O)( Q21 )( Q22 ), -P(=S)( Q21 )( Q22 ), or any combination thereof, substituting or unsubstituted, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group; -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(Q 31 )(Q 32 ); or Any combination of these; and, The above Q1 to Q3 , Q11 to Q13 , Q21 to Q23 , and Q31 to Q33 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3 - C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C 6 - C60 aryloxy group, C6 - C60 aryltio group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group; or Deuterium, C1 - C60 alkyl group, C6 - C60 aryl group, C1 - C60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group or any combination thereof substituted with, C1 - C60 alkyl group, C2 - C60 alkenyl group, C2 - C60 alkynyl group, C1 - C60 alkoxy group, C3 - C10 cycloalkyl group, C1 - C10 heterocycloalkyl group, C3- C10 cycloalkenyl group, C1 - C10 heterocycloalkenyl group, C6 - C60 aryl group, C6 - C60 aryloxy group, C6 - C60 arylthio group, C1 - C60 heteroaryl group, It is a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group.
  2. In paragraph 1, Y 11 and Y 21 are independently O, S, or Se, and Y 12 and Y 22 are heterocyclic compounds in which they are independently O, S, Se, N(Ar 3 ), N(R 1 ), C(R 1 )(R 2 ) or Si(R 1 )(R 2 ).
  3. In paragraph 1, A heterocyclic compound in which CY 11 to CY 13 , CY 21 to CY 23 and CY 3 to CY 6 are 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 naphthiridine group, a quinoxaline group, a quinazoline group, a carbazole group, a dibenzofuran group, a dibenzothiophen group, a dibenzosilol group, a dibenzoborol group, a dibenzophosphor group, a dibenzoselenophene group, a dibenzozermol group, a dibenzothiophen 5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophen 5,5-dioxide group.
  4. In paragraph 1, A heterocyclic compound in which the group represented by the above chemical formula 2 is the group represented by the following chemical formula 2A: <Chemical Formula 2A> Among the above chemical formula 2A, X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, and 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, and 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, and The descriptions of R 41 to R 43 are independent of each other and are identical to the description of R 40 in claim 1, and The descriptions of R 51 to R 55 are independent of each other and are identical to the description of R 50 in claim 1, and The descriptions of R 61 to R 65 are independent of each other and are identical to the description of R 50 in claim 1, and * is a bonding site with a neighboring atom.
  5. In paragraph 1, A heterocyclic compound in which the group represented by the above chemical formula 2 is the group represented by the following chemical formula 2A-1: <Chemical Formula 2A-1> In the above chemical formula 2A-1, The descriptions of R 41 to R 43 are independent of each other and are identical to the description of R 40 in claim 1, and The descriptions of R 51 to R 55 are independent of each other and are identical to the description of R 50 in claim 1, and The descriptions of R 61 to R 65 are independent of each other and are identical to the description of R 50 in claim 1, and * is a bonding site with a neighboring atom.
  6. In paragraph 1, R 1 to R 4 , R 10 , R 20 , R 30 , R 40 , R 50 , and R 60 independently of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, -SF5 , C1 - C20 alkyl group or C1 - C20 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 - C20 alkyl group, deuterium-containing C1 - C20 alkyl group, fluorinated C1 - C20 alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, Bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group (norbonanyl group), bicyclo[2.2.2]octyl group, ( C1 - C20 alkyl)cyclopentyl group, ( C1 - C20 alkyl)cyclohexyl group, ( C1 - C20 alkyl)cycloheptyl group, ( C1 - C20 alkyl)cyclooctyl group, ( C1 - C20 alkyl)adamantanyl group, ( C1 - C20 alkyl)norbornenyl group, ( C1 - C20 alkyl)cyclopentenyl group, (C1- C20 alkyl)cyclohexenyl group, ( C1 - C20 alkyl)cycloheptenyl group, ( C1 - C20 alkyl)bicyclo[1.1.1]pentyl group, ( C1 -C20 alkyl)bicyclo[2.1.1]hexyl group, ( C1 - C20 alkyl)bicyclo[2.2.1]heptyl group, ( C1 - C20 alkyl)bicyclo[2.2.2]octyl group, silolanyl group, phenyl group, ( C1 - C20 alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof, substituted with a C1 - C20 alkyl group or a C1 - C20 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3 , -CD2H , -CDH2, -CF3 , -CF2H , -CFH2 , hydroxyl group , cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1 - C20 alkyl group, deuterium-containing C1 - C20 alkyl group, fluorinated C1 - C20 alkyl group, C1 - C20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, Bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, ( C1 - C20 alkyl)cyclopentyl group, ( C1 - C20 alkyl)cyclohexyl group, ( C1 - C20 alkyl)cycloheptyl group, (C1- C20 alkyl)cyclooctyl group, ( C1 -C20 alkyl)adamantanyl group, ( C1 - C20 alkyl )norbornenyl group, ( C1 - C20 alkyl)cyclopentenyl group, ( C1 - C20 alkyl)cyclohexenyl group, ( C1 - C20 alkyl)cycloheptenyl group, ( C1 - C20 alkyl)bicyclo[1.1.1]pentyl group, ( C1 - C20 Alkyl)bicyclo[2.1.1]hexyl group, ( C1 - C20 alkyl)bicyclo[2.2.1]heptyl group, ( C1 - C20 alkyl)bicyclo[2.2.2]octyl group, silanyl group, phenyl group, ( C1 - C20 alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazoleyl group, pyrazolyl group, thiazoleyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridadinyl group, isoindole group, indole group, indazole group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole group, phenanthrolinyl group, benzimidazole group, benzofuranyl group, benzothiophenyl group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole group, dibenzocarbazole group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophenyl group, or Substituted or unsubstituted by any combination thereof, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, silanyl group, phenyl group, ( C1 - C20 alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, Imidazole single group, pyrazol single group, thiazole single group, isothiazol single group, oxazol single group, isoxazol single group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole single group, indole single group, indazole single group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole single group, phenanthrolinyl group, benzimidazole single group, benzofuranyl group, benzothiophenyl group, isobenzothiazol single group, benzoxazol single group, isobenzoxazol single group, triazole single group, tetrazol single group, oxadiazole single group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole single group, Dibenzocarbazole yl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazole yl group, azadibenzofuranyl group or azadibenzothiophenyl group; or Heterocyclic compounds that are -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 ).
  7. In paragraph 1, A heterocyclic compound in which at least one of the R 30 of b30 is -F, -Cl, -Br, -I, -SF5 , cyano group, substituted or unsubstituted C1 - C60 alkyl group, substituted or unsubstituted C3 - C10 cycloalkyl group, substituted or unsubstituted C6 - C60 aryl group, substituted or unsubstituted C1 - C60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.
  8. In paragraph 1, The above heterocyclic compound is a heterocyclic compound represented by the following chemical formula 11: <Chemical Formula 11> Among the above chemical formula 11, The descriptions of Y 11 , Y 12 , Y 21 , Y 22 , Ar 1 , and Ar 2 are the same as in Paragraph 1, and 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, and 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, and X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, and The descriptions of R 11 to R 19 are independent of each other and are identical to the description of R 10 in claim 1, and The descriptions of R 21 to R 29 are independent of each other and are identical to the description of R 20 in claim 1, and The descriptions of R 31 to R 33 are independent of each other and are identical to the description of R 30 in paragraph 1.
  9. In paragraph 8, R 32 is -F, -Cl, -Br, -I, -SF 5 , cyano group, substituted or unsubstituted C 1 -C 60 alkyl group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, and A heterocyclic compound in which R 31 and R 33 are independently hydrogen or deuterium.
  10. In paragraph 1, The above heterocyclic compound is a heterocyclic compound represented by the following chemical formula 21: <Chemical Formula 21> Among the above chemical formula 21, The descriptions of Y 11 , Y 12 , Y 21 , Y 22 , Ar 1 , and Ar 2 are the same as in Paragraph 1, and The descriptions of R 11 to R 19 are independent of each other and are identical to the description of R 10 in claim 1, and The descriptions of R 21 to R 29 are independent of each other and are identical to the description of R 20 in claim 1, and The descriptions of R 31 to R 33 are independent of each other and are identical to the description of R 30 in paragraph 1.
  11. In paragraph 1, The above heterocyclic compound is a heterocyclic compound represented by the following chemical formula 31: <Chemical Formula 31> Among the above chemical formula 31, The descriptions of Y 11 , Y 12 , Y 21 , Y 22 , Ar 1 , and Ar 2 are the same as in Paragraph 1, and The descriptions of R 11 to R 19 are independent of each other and are identical to the description of R 10 in claim 1, and The descriptions of R 21 to R 29 are independent of each other and are identical to the description of R 20 in claim 1, and The descriptions of R 31 to R 33 are independent of each other and are identical to the description of R 30 in claim 1, and The descriptions of R 41 to R 43 and R 41a to R 43a are independent of each other and are identical to the description of R 40 in claim 1, and The descriptions of R 51 to R 55 and R 51a to R 55a are independent of each other and are identical to the description of R 50 in claim 1, and The descriptions of R 61 to R 65 and R 61a to R 65a are independent of each other and are identical to the description of R 60 in claim 1.
  12. In paragraph 1, A heterocyclic compound, any one of the following compounds 1 to 510: .
  13. First electrode; Second electrode; and An organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; comprising An organic light-emitting device in which the above organic layer comprises a heterocyclic compound of any one of claims 1 to 12.
  14. In Paragraph 13, An organic light-emitting device in which the light-emitting layer comprises the heterocyclic compound.
  15. In Paragraph 14, The above-mentioned light-emitting layer includes a host and an emitter, and An organic light-emitting device in which the emitter comprises the heterocyclic compound.
  16. In paragraph 15, An organic light-emitting device in which the content of the above host is greater than the content of the above heterocyclic compound.
  17. In paragraph 15, An organic light-emitting device in which the light-emitting layer further includes a sensorizer.
  18. In Paragraph 17, The above-mentioned sensor is an organic light-emitting device including a phosphorescent dopant.
  19. In Paragraph 14, The above-described light-emitting layer is an organic light-emitting device that emits blue light with a maximum emission wavelength of 400 nm to 490 nm.
  20. An electronic device including the organic light-emitting element of paragraph 13.

Description

Heterocyclic compound, organic light-emitting device including the same, and electronic apparatus A heterocyclic compound, an organic light-emitting diode containing the same, and an electronic device are presented. Organic light-emitting devices are self-luminous devices that have excellent viewing angle, response time, brightness, driving voltage, and response speed, and can be multicolored. According to one example, an organic light-emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode, which includes a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. FIG. 1 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment. FIGS. 2 to 6 are schematic diagrams showing the energy transition of an organic light-emitting device according to one embodiment. A heterocyclic compound according to one embodiment is represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, Y 11 and Y 12 are independently single bonds, 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). In the above chemical formula 1, Y 21 and Y 22 are independently single bonds, 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). According to one embodiment, Y 11 and Y 21 may be O, S, or Se independently of each other. According to one embodiment, Y12 and Y22 may be independently O, S, Se, N( Ar3 ), N( R1 ), C( R1 )( R2 ) or Si( R1 )( R2 ). In the above Chemical Formula 1, Ar 1 to Ar 4 are independently of each other the group represented by the following Chemical Formula 2. <Chemical Formula 2> In the above chemical formulas 1 and 2, CY 11 to CY 13 , CY 21 to CY 23 and CY 3 to CY 6 are independently C 5 -C 30 carbocyclic groups or substituted or unsubstituted C 1 -C 30 heterocyclic groups. Among the above chemical formula 2, represents a single bond or a double bond. In the above chemical formula 2, * is a bonding site with an adjacent atom. According to one embodiment, the CY 11 to CY 13 , CY 21 to CY 23 and CY 3 to CY 6 are independently of each other i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed together, iv) a condensed ring in which two or more second rings are condensed together, or v) a condensed ring in which one or more first rings and one or more second rings are condensed together. The first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzocilol group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiazole group, a thiatriazole group, an isothiazole group, a pyrazol group, an imidazole group, a triazole group, a tetrazole group, an azacilol group, a diazcilol group, or a triazcilol group, and The second ring above may be an adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2.2]octane group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group. According to one embodiment, CY 11 to CY 13 , CY 21 to CY 23 and CY 3 to CY 6 may independently be C 6 -C 30 aromatic carbocyclic groups or C 1 -C 30 aromatic heterocyclic groups. According to one embodiment, CY 11 to CY 13 , CY 21 to CY 23 and CY 3 to CY 6 are independently a benzene group, a naphthalene group, anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzocilol group, a benzoborol group, a benzophospol group, a benzoselenopene group, a benzozermol group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzocilol group, a dibenzoborol group, a dibenzophospol group, a dibenzoselenopene group, a dibenzozermol group, a dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5