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US 12,735,634 B2Granted
Light-emitting device including heterocyclic compound and electronic apparatus including the light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsSeran Kim, Hoilim Kim, Dongsun Yoo, Saena Yun
Life of this patent
Estimating the term…
Abstract
An electronic device that includes a light-emitting device includes: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound of Formula 1: wherein the variables in Formula 1 are defined herein.
Claims20
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- an interlayer located between the first electrode and the second electrode and comprising an emission layer;
- and
- a heterocyclic compound of Formula 1:
- wherein, in Formulae 1 and 2,
- Y1 is B, P(═O), or P(═S),
- Y2 is B, P(═O), or P(═S),
- a1 to a5 are each, independently from one another, an integer from 0 to 4,
- X1 is N(Ar1a)(Ar1b), N(Ar1a)(Z1a), or N(Z1a)(Z1b),
- X2 is N(Ar2z)(Ar2b), N(Ar2z)(Z2a), or N(Z2a)(Z2b),
- X3 is N(Ar3a)(Ar3b), N(Ar3a)(Z3a), or N(Z3a)(Z3b),
- X4 is N(Ar4a)(Ar4b), N(Ar4a)(Z4a), or N(Z4a)(Z4b),
- X5 is N(Ar5a)(Ar5b), N(Ar5a)(Z5a), or N(Z5a)(Z5b),
- X6 is O, S, N(Ar6), or N(Z6),
- X7 is O, S, N(Ar7), or N(Z7),
- X8 is O, S, N(Ar8), or N(Z8),
- X9 is O, S, N(Ar9), or N(Z9),
- Ar1a, Ar1b, Ar2a, Ar2b, Ar3a, Ar3b, Ar4a, Ar4b, Ar5a, Ar5b, and Ar6 to Ar9 are each, independently from one another, a group of Formula 2,
- ring CY1 to ring CY7 are each, independently from one another, a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
- T1 is Se or Te,
- b1 to b7 are each, independently from one another, an integer from 0 to 8,
- Z1a, Z1b, Z2a, Z2b, Z3a, Z3b, Z4a, Z4b, Z5a, Z5b, Z6 to Z9, and R1 to R7 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 aryl alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroaryl alkyl group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- c1 is an integer from 0 to 3,
- L1 is a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
- Formula 1 satisfies at least one of Conditions (1) to (9),
- Condition (1)
- a1 is an integer of 1 or more, and at least one of X1(s) in the number of a1 is N(Ar1a)(Ar1b) or N(Ar1a)(Z1a)
- Condition (2)
- a2 is an integer of 1 or more, and at least one of X2(s) in the number of a2 is N(Ar2a)(Ar2b) or N(Ar2a)(Z2a)
- Condition (3)
- a3 is an integer of 1 or more, and at least one of X3(s) in the number of a3 is N(Ar3a)(Ar3b) or N(Ar3a)(Z3a)
- Condition (4)
- a4 is an integer of 1 or more, and at least one of X4(s) in the number of a4 is N(Ar4a)(Ar4b) or N(Ar4a)(Z4a)
- Condition (5)
- a5 is an integer of 1 or more, and at least one of X5(s) in the number of a5 is N(Ar5a)(Ar5b) or N(Ar5a)(Z5a)
- Condition (6)
- X6 is N(Ar6)
- Condition (7)
- X7 is N(Ar7)
- Condition (8)
- X8 is N(Ar8)
- Condition (9)
- X9 is N(Ar9),
- provided that when T1 is Se, Formula 1 satisfies at least two of Conditions (1) to (9),
- * in Formula 2 is a binding site to Formula 1, and
- R10a is:
- deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro 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, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(q11)(q12)(q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11),
- —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-Coo aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof;
- 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:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- a C1-C60 alkyl group;
- a C2-C60 alkenyl group;
- a C2-C60 alkynyl group;
- a C1-C60 alkoxy group;
- a C3-C60 carbocyclic group or a C1-C60 heterocyclic group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof;
- a C7-C60 aryl alkyl group;
- or a C2-C60 heteroaryl alkyl group.
67 more elements
Dependencies are inferred from the claim text.