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US 12,120,953 B2Granted
Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic apparatus including organic light-emitting device
AssigneeSamsung Electronics Co., Ltd.
InventorsSoonok Jeon, Dmitry Androsov, Juhyun Kim, Jong Soo Kim, Sooghang Ihn
Life of this patent
Estimating the term…
Abstract
Provided are a heterocyclic compound represented by Formula 1, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device: wherein Formula 1 may be understood by referring to the description of Formula 1 provided herein.
Claims19
A heterocyclic compound represented by Formula 1:
- wherein, in Formula 1,
- ring CY1, ring CY2, ring CY4, and ring CY5 are each independently a π electron-rich C3-C60 cyclic group, wherein ring CY1, ring CY2, ring CY4, and ring CY5 are each independently a benzene group, a naphthalene group, a phenanthrene group, a furan group, a thiophene group, a pyrrole group, a cyclopentene group, a silole group, a germole group, a benzofuran group, a benzothiophene group, an indole group, an indene group, a benzosilole group, a benzogermole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, an indolodibenzofuran group, an indolodibenzothiophene group, an undolocarbazole group, an indolofluorene group, an indolodibenzosilole group, an indolodibenzogermole group, or a 9,10-dihydroacridine group,
- X1 is O, S, Si(R5)(R6), Ge(R5)(R6), or P(═O)(R5),
- X3 is a single bond, O, S, N(R31), C(R31)(R32), Si(R31)(R32), or Ge(R31)(R32),
- R1, R2, R4 to R6, R10, and R20 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 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 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 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 C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl 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(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
- R31, R32, R40, and R50 are each independently:
- hydrogen, deuterium, —F, or a cyano group;
- or
- a C1-C60 alkyl group, a C1-C60 alkoxy group, a π electron-rich C3-C60 cyclic group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a π electron-rich C3-C60 cyclic group, a pyridinyl group, a biphenyl group, a terphenyl group, or any combination thereof, wherein the π electron-rich C3-C60 cyclic group is a cyclic group having 3 to 60 carbon atoms and not including at least one *—N═*′ as a ring-forming moiety, wherein * and *′ each indicated a binding site to an adjacent atom,
- a1, a2, a4, and a5 are each independently an integer from 0 to 20, and
- a substituent of 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 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 C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
- deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —C1, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-Coo aryl group, a C6-Coo aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-Coo arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —C1, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-Coo arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
- —N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39);
- or
- any combination thereof,
- wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro 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 C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof;
- a C2-C60 alkenyl group;
- a C2-C60 alkynyl group;
- a C1-C60 alkoxy group;
- a C3-C10 cycloalkyl group;
- a C1-C10 heterocycloalkyl group;
- a C3-C10 cycloalkenyl group;
- a C1-C10 heterocycloalkenyl group;
- a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof;
- a C6-C60 aryloxy group;
- a C6-C60 arylthio group;
- a C1-C60 heteroaryl group;
- a monovalent non-aromatic condensed polycyclic group;
- or a monovalent non-aromatic condensed heteropolycyclic group.
44 more elements
Dependencies are inferred from the claim text.