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US 11,697,645 B2Granted
Heterocyclic compound, composition including heterocyclic compound, and organic light-emitting device including heterocyclic compound
AssigneeSamsung Electronics Co., Ltd.
InventorsMasaki Numata, Mitsunori Ito, Norihito Ishii, Rie Sakurai
Life of this patent
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Abstract
A heterocyclic compound, a composition including the heterocyclic compound, and an organic light-emitting device including the heterocyclic compound are disclosed. The heterocyclic compound is represented by Formula 1: wherein, X1, L1, a1, Ar1, R1 to R6, b3, b4, and b5 are described herein.
Claims19
A heterocyclic compound represented by Formula 1:
- wherein the heterocyclic compound satisfies Equation 1:
- |EHOMO−ELUMO|≥3.0 eV Equation 1
- wherein, in Equation 1, EHOMO indicates a HOMO energy level value of the heterocyclic compound, and ELUMO indicates a LUMO energy level value of the heterocyclic compound,
- wherein, in Formulae 1 and 2,
- X1 is O, S, or Se,
- L1 and L11 are each independently a single bond, a substituted or unsubstituted benzene group, or a substituted or unsubstituted naphthalene group,
- a1 and a11 are each independently an integer from 1 to 10,
- Ar1 and Ar11 are each independently a substituted or unsubstituted benzene group, or a substituted or unsubstituted naphthalene group,
- R1 to R6 are each independently a group represented by Formula 2, hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, or a substituted or unsubstituted C1-C60 alkoxy group,
- b3 is an integer from 0 to 3,
- b4 is an integer from 0 to 4,
- b5 is an integer from 0 to 5,
- at least one substituent of the substituted benzene group, the substituted naphthalene group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, and the substituted C1-C60 alkoxy group is:
- deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —NCS, 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, or any combination thereof,
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —NCS, 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, Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —C(═O)(Q11), or any combination thereof;
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, or any combination thereof,
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, or any combination thereof, each substituted with at least one 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, 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —C(═O)(Q21), or any combination thereof;
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —C(═O)(Q31), or any combination thereof,
- wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, or a biphenyl group, and
- * indicates a binding site to an adjacent atom.
18 more elements
A heterocyclic compound represented by Formula 1:
- wherein, in Formulae 1 and 2,
- X1 is O, S, or Se,
- i) L1 is a single bond, L11 is a substituted or unsubstituted benzene group, and a11 is 1 or 2;
- ii) L1 and L11 are each a substituted or unsubstituted benzene group, and a1 and a11 are each 1;
- iii) L1 and L11 are each a substituted or unsubstituted benzene group, a1 is 1, and a11 is 2;
- or
- iv) L1 and L11 are each a substituted or unsubstituted benzene group, and a1 and a11 are each 2,
- Ar1 and Ar11 are each independently a substituted or unsubstituted benzene group, or a substituted or unsubstituted naphthalene group,
- R1 to R6 are each independently a group represented by Formula 2, hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, or a substituted or unsubstituted C1-C60 alkoxy group,
- b3 is an integer from 0 to 3,
- b4 is an integer from 0 to 4,
- b5 is an integer from 0 to 5,
- at least one substituent of the substituted benzene group, the substituted naphthalene group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, and the substituted C1-C60 alkoxy group is:
- deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —NCS, 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, or any combination thereof;
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or any combination thereof, each substituted with at least one deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —NCS, 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, Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —C(═O)(Q11), or any combination thereof;
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, or any combination thereof:
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, or any combination thereof, each substituted with at least one 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, 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —C(═O)(Q21), or any combination thereof;
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —C(═O)(Q31), or any combination thereof,
- wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, or a biphenyl group, and
- * indicates a binding site to an adjacent atom.
18 more elements
A heterocyclic compound, wherein the heterocyclic compound is at least one of Compounds 1 to 24:
Dependencies are inferred from the claim text.