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US 2021/0280798 A1Published application
Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic apparatus including organic light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsSunyoung Pak, Seokhwan Hwang, Junha Park, Hankyu Pak, Jangyeol Baek, Chanseok Oh, Hyoyoung Lee
Life of this patent
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Abstract
An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1, as defined herein.
Claims20
An organic light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- an organic layer between the first electrode and the second electrode and comprising an emission layer;
- and
- a heterocyclic compound represented by Formula 1:
- wherein, in Formula 1,
- E1 to E3 are each, independently from one another, a cyano group, a fluoro group, a cyano group-containing C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a fluoro group-containing C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a cyano group-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a fluoro group-containing C1-C30 cyclic group, a π electron-depleted nitrogen-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a boron-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a C1-C30 cyclic group unsubstituted or substituted with at least one R10a and comprising *—S(═O)2—*′ as a ring-forming moiety, a group represented by *—B(Q51)(Q52), a group represented by *—C(═O)(Q51), a group represented by *—S(═O)2(Q51), or a group represented by *—P(═O)(Q51)(Q52);
- L1 to L3 are each, independently from one another, a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C2-C30 heterocyclic group unsubstituted or substituted with at least one R10a;
- a1 to a3 and b1 to b3 are each, independently from one another, an integer from 1 to 10;
- n1 to n3 are each, independently from one another, an integer from 0 to 4, and at least one of n1 to n3 is 1 or greater;
- R1 to R3, R10a, Q51, Q52, and R21 to R23 are each, independently from one another, of 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 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 C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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 fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2);
- d21 to d23 are each, independently from one another, an integer from 0 to 4;
- 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 fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:
- deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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, independently from one another, substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
- 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group, each, independently from one another, unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22);
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
- wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another, of:
- 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 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 C1-C60 heteroaryl group;
- a monovalent non-aromatic fused polycyclic group;
- a monovalent non-aromatic fused heteropolycyclic group;
- a C1-C60 alkyl group substituted with at least one of deuterium, —F, and a cyano group;
- a C6-C60 aryl group substituted with at least one of deuterium, —F, and a cyano group;
- a biphenyl group;
- or a terphenyl group.
45 more elements
A heterocyclic compound represented by Formula 1:
- wherein, in Formula 1,
- E1 to E3 are each, independently from one another, a cyano group, a fluoro group, a cyano group-containing C1-C60 alkyl group, a fluoro group-containing C1-C60 alkyl group, a cyano group-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a fluoro group-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a π electron-depleted nitrogen-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a boron-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a C1-C30 cyclic group unsubstituted or substituted with at least one R10a and comprising *—S(═O)2—*′ as a ring-forming moiety, a group represented by *—B(Q51)(Q52), a group represented by *—C(═O)(Q51), a group represented by *—S(═O)2(Q51), or a group represented by *—P(═O)(Q51)(Q52),
- L1 to L3 are each, independently from one another, a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C2-C30 heterocyclic group unsubstituted or substituted with at least one R10a;
- a1 to a3 and b1 to b3 are each, independently from one another, an integer from 1 to 10;
- n1 to n3 are each, independently from one another, an integer from 0 to 4, and at least one of n1 to n3 is 1 or greater;
- R1 to R3, R10a, Q51, Q52, and R21 to R23 are each, independently from one another, of 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 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 C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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 fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2);
- d21 to d23 are each, independently from one another, an integer from 0 to 4, 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 fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:
- deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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, independently from one another, substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 so group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
- 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group, each, independently from one another, unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22);
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
- wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another, of:
- 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 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 C1-C60 heteroaryl group;
- a monovalent non-aromatic fused polycyclic group;
- a monovalent non-aromatic fused heteropolycyclic group;
- a C1-C60 alkyl group substituted with at least one of deuterium, —F, and a cyano group;
- a C6-C60 aryl group substituted with at least one of deuterium, —F, and a cyano group;
- a biphenyl group;
- or a terphenyl group.
39 more elements
Dependencies are inferred from the claim text.