Back to results
US 12,757,628 B2Granted
Light-emitting device including heterocyclic compound, electronic apparatus including the same, and the heterocyclic compound
AssigneeSamsung Display Co., Ltd.
InventorsYeseul Lee, Hyeongmin Kim, Youngjin Park, Heechoon Ahn, Hyunah Um, Juhui Yun
Life of this patent
Estimating the term…
Abstract
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, the interlayer including an emission layer, and a heterocyclic compound represented by Formula 1, and an electronic apparatus includes the light-emitting device: wherein Formula 1 is as defined in the present specification.
Claims20
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- an interlayer between the first electrode and the second electrode, the interlayer comprising an emission layer;
- and
- a heterocyclic compound represented by Formula 1:
- wherein in Formula 1,
- X1 is a single bond, O, S, N(Q1), P(Q1), C(Q1)(Q2), or Si(Q1)(Q2),
- Y1 is C or Si,
- rings CY1 to CY4 are each independently a C6-C60 carbocyclic group or a C3-C60 heterocyclic group,
- L11, L12, L21, L22, L23, L24, Ar11, Ar12, Ar21, Ar22, and Ar23 are each independently a C6-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C3-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- a11, a12, a21, a22, a23, and a24 are each independently an integer from 0 to 3,
- *-(L11)a11-*′ is a single bond when a11 is 0,
- *-(L12)a12-*′ is a single bond when a12 is 0,
- *-(L21)a21-*′ is a single bond when a21 is 0,
- *-(L22)a22-*′ is a single bond when a22 is 0,
- *-(L23)a23-*′ is a single bond when a23 is 0,
- *-(L24)a24-*′ is a single bond when a24 is 0,
- * and *′ each indicate a binding site to a neighboring atom,
- b11 and b12 are each independently an integer of 0 to 4,
- R10a, R10aa, R10ab, R10ac, R10ad, and R10ae are each independently:
- 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),
- c11 to c14 are each independently an integer from 0 to 8,
- c15 is an integer from 0 to 3,
- a sum of b11+c11 is 8 or less,
- a sum of b12+c12 is 8 or less,
- Q1, Q2, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently:
- 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;
- or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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
- Q1 and Q2 are optionally bonded to each other to form 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.
42 more elements
A heterocyclic compound represented by Formula 1:
- wherein in Formula 1,
- X1 is a single bond, O, S, N(Q1), P(Q1), C(Q1)(Q2), or Si(Q1)(Q2),
- Y1 is C or Si,
- rings CY1 to CY4 are each independently a C6-C60 carbocyclic group or a C3-C60 heterocyclic group,
- L11, L12, L21, L22, L23, L24, Ar11, Ar12, Ar21, Ar22, and Ar23 are each independently a C6-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C3-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- a11, a12, a21, a22, a23, and a24 are each independently an integer from 0 to 3,
- *-(L11)a11-*′ is a single bond when a11 is 0,
- *-(L12)a12-*′ is a single bond when a12 is 0,
- *-(L21)a21-*′ is a single bond when a21 is 0,
- *-(L22)a22-*′ is a single bond when a22 is 0,
- *-(L23)a23-*′ is a single bond when a23 is 0,
- *-(L24)a24-*′ is a single bond when a24 is 0,
- * and *′ each indicate a binding site to a neighboring atom,
- b11 and b12 are each independently an integer from 0 to 4,
- R10a, R10aa, R10ab, R10ac, R10ad, and R10ae are each independently:
- 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),
- c11 to c14 are each independently an integer from 0 to 8,
- c15 is an integer from 0 to 3,
- a sum of b11+c11 is 8 or less,
- a sum of b12+c12 is 8 or less,
- Q1, Q2, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently:
- 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;
- or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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
- Q1 and Q2 are optionally bonded to each other to form 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.
37 more elements
A heterocyclic compound satisfying both Conditions v and vi:
- v) the heterocyclic compound comprises a core represented by Formula 1-1:
- wherein in Formula 1-1,
- X1 is a single bond, O, S, N(Q1), P(Q1), C(Q1)(Q2), or Si(Q1)(Q2),
- Q1 and Q2 are each independently 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;
- or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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
- Q1 and Q2 are optionally bonded to each other to form 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;
- and
- vi) a T1 energy level of the heterocyclic compound is in a range of about 2.95 eV to about 3.05 eV, or
- a HOMO energy level of the heterocyclic compound is in a range of about −5.60 eV to about −5.35 eV, or
- a LUMO energy level of the heterocyclic compound is in a range of about −2.30 eV to about −1.75 eV.
19 more elements
Dependencies are inferred from the claim text.