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US 12,588,354 B2Granted
Light-emitting device including fused cyclic compound, electronic apparatus including the light-emitting device, and the fused cyclic compound
AssigneeSamsung Display Co., Ltd.
InventorsSeran Kim, Hoilim Kim, Dongsun Yoo, Saena Yun
Life of this patent
Estimating the term…
Abstract
A light-emitting device having a fused cyclic compound 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 fused cyclic compound of Formula 1: wherein, in Formula 1, the variables are as defined herein.
Claims19
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- a first layer between the first electrode and the second electrode and comprising a second layer;
- and
- a fused cyclic compound of Formula 1:
- wherein, in Formula 1 and Formula 2,
- rings A1 to A4, B1, and B21 are each, independently from one another, a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
- Y1 and Y2 are each, independently from one another, B, P(═O), or P(═S),
- X1 is N(Ar1), N(Z1), O, S, or Se,
- X2 is N(Ar2), N(Z2), O, S, or Se,
- X3 is N(Ar3), N(Z3), O, S, or Se,
- X4 is N(Ar4), N(Z4), O, S, or Se,
- Z1 to Z4 are each, independently from one another, a group of Formula 2,
- Ar1 to Ar4, R1 to R5, and R21 are each independently 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 R10, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- T1 to T4 each independently comprise a group of Formula 2,
- a1 to a5, b1 to b4, and a21 are each, independently from one another, an integer from 0 to 10,
- X21 and X22 are each, independently from one another, carbon or a heteroatom, and X21 and X22 are linked to each other by a chemical bond,
- L21 is a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- d21 is an integer from 1 to 3,
- R22 is a hydroxyl group, a C1-C20 alkyl group unsubstituted or substituted with at least one R10a, provided that the C1-C20 alkyl group unsubstituted or substituted with at least one R10a is not a methyl group, 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 C1-C60 aryl group unsubstituted or substituted with at least one R10a, or —N(Q1)(Q2),
- * indicates a binding site to a neighboring atom,
- 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 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, —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, or a C6-C60 arylthio 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, —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:
- a group of Formula 2;
- 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 or a C1-C60 alkoxy group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group or any combination thereof;
- 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, and
- the fused cyclic compound satisfies at least one of Conditions 1 to 5:
- Condition 1 X1 is N(Z1),
- Condition 2 X2 is N(Z2),
- Condition 3 X3 is N(Z3),
- Condition 4 X4 is N(Z4),
- Condition 5 The sum of b1 to b4 is 1 or more.
42 more elements
A fused cyclic compound of Formula 1:
- wherein, in Formula 1 and Formula 2,
- rings A1 to A4, B1, and B21 are each, independently from one another, a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
- Y1 and Y2 are each, independently from one another, B, P(═O), or P(═S),
- X1 is N(Ar1), N(Z1), O, S, or Se,
- X2 is N(Ar2), N(Z2), O, S, or Se,
- X3 is N(Ar3), N(Z3), O, S, or Se,
- X4 is N(Ar4), N(Z4), O, S, or Se,
- Z1 to Z4 are each, independently from one another, a group of Formula 2,
- Ar1 to Ar4, R1 to R5, and R21 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 R10, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- T1 to T4 each independently comprise a group of Formula 2,
- a1 to a5, b1 to b4, and a21 are each, independently from one another, an integer from 0 to 10,
- X21 and X22 are each, independently from one another, carbon or a heteroatom, and X21 and X22 are linked to each other by a chemical bond,
- L21 is a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- d21 is an integer from 1 to 3,
- R22 is a hydroxyl group, a C1-C20 alkyl group unsubstituted or substituted with at least one R10a, provided that the C1-C20 alkyl group unsubstituted or substituted with at least one R10a is not a methyl group, 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 C1-C60 aryl group unsubstituted or substituted with at least one R10a, or —N(Q1)(Q2),
- * indicates a binding site to a neighboring atom,
- 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 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, —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, or a C6-C60 arylthio 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, —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:
- a group of Formula 2;
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- C1-C60 alkyl group, C2-C60 alkenyl group, C2-C60 alkynyl group or C1-C60 alkoxy group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group or any combination thereof;
- 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, and
- the fused cyclic compound satisfies at least one of Conditions 1 to 5:
- Condition 1 X1 is N(Z1),
- Condition 2 X2 is N(Z2),
- Condition 3 X3 is N(Z3),
- Condition 4 X4 is N(Z4),
- Condition 5 the sum of b1 to b4 is 1 or more.
38 more elements
Dependencies are inferred from the claim text.