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US 12,733,391 B2Granted
Organometallic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsJaesung Lee, Iljoon Kang, Sungbum Kim, Sujin Shin, Eunyoung Lee, Mina Jeon
Life of this patent
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Abstract
Embodiments provide an organometallic compound, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device. The organometallic compound is represented by Formula 1, which is explained in the 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 and comprising an emission layer;
- and
- an organometallic compound represented by Formula 1:
- wherein in Formula 1,
- M1 and M2 are each independently platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
- A1 to A4 and B1 to B4 are each independently a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
- Y10, Y20, Y30, Y40, Y50, Y60, Y70, and Y80 are each independently C or N,
- two bonds selected from a bond between Y10 and M1, a bond between Y20 and M1, a bond between Y50 and M1, and a bond between Y60 and M1 are each a coordinate bond, and the remainder thereof are each a covalent bond,
- two bonds selected from a bond between Y30 and M2, a bond between Y40 and M2, a bond between Y70 and M2, and a bond between Y80 and M2 are each a coordinate bond, and the remainder thereof are each a covalent bond,
- T1 and T2 are each independently a single bond, *—O—*′, *—S—*′, *—C(R1)(R2)—*′, *—C(R1)═′, *═C(R1)—*′, *—C(R1)═C(R2)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1)—*′, *—N(R1)—*′, *—P(R1)—*′, *—Si(R1)(R2)—*′, *—P(R1)(R2)—*′, or *—Ge(R1)(R2)—*′,
- T3 and T4 are each independently a single bond, *—O—*′, *—S—*′, *—C(R3)(R4)—*′, *—C(R3)═*′, *═C(R3)—*′, *—C(R3)═C(R4)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R3)—*′, *—N(R3)—*′, *—P(R3)—*′, *—Si(R3)(R4)—*′, *—P(R3)(R4)—*′ or *—Ge(R3)(R4)—*′,
- n1 to n4 are each independently 1, 2, or 3,
- X1 is N, P, C(R5), or Si(R5),
- X2 is N, P, C(R6), or Si(R6),
- L10 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,
- a10 is 1, 2, 3, 4, or 5,
- * and *′ each indicate a binding site to a neighboring atom,
- R1 to R6, R10, R20, R30, R40, R50, R60, R70, and R80 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 R10a, a C1-C60alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio 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),
- b10, b20, b30, b40, b50, b60, b70, and b80 are each independently an integer from 0 to 20,
- each of:
- R1 and R2;
- R3 and R4;
- two or more of R10 in the number of b10;
- two or more of R20 in the number of b20;
- two or more of R30 in the number of b30, two or more of R40 in the number of b40;
- two or more of R50 in the number of b50;
- two or more of R60 in the number of b60;
- two or more of R70 in the number of b70;
- and two or more of R80 in the number of b80 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,
- two or more of R1, R2, R10, R20, R50, and R60 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,
- two or more of R3, R4, R30, R40, R70, and R80 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,
- R10a is:
- deuterium, —F, —Cl, —Br, 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, a C1-C60 alkoxy group, or a C1-C60 alkylthio 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, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl 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 C1-C60 alkylthio group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a 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:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- or 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 C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl 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 a combination thereof.
47 more elements
An organometallic compound represented by Formula 1:
- wherein in Formula 1,
- M1 and M2 are each independently platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
- A1 to A4 and B1 to B4 are each independently a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
- Y10, Y20, Y30, Y40, Y50, Y60, Y70, and Y80 are each independently C or N,
- two bonds selected from a bond between Yeo and M1, a bond between Y20 and M1, a bond between Y50 and M1, and a bond between Y60 and M1 are each a coordinate bond, and the remainder thereof are each a covalent bond,
- two bonds selected from a bond between Y30 and M2, a bond between Y40 and M2, a bond between Y70 and M2, and a bond between Y80 and M2 are each a coordinate bond, and the remainder thereof are each a covalent bond,
- T1 and T2 are each independently a single bond, *—O—*′, *—S—*′, *—C(R1)(R2)—*′, *—C(R1)═*′, *═C(R1)—*′, *—C(R1)═C(R2)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1)—*′, *—N(R1)—*′, *—P(R1)—*′, *—Si(R1)(R2)—*′, *—P(R1)(R2)—*′, or *—Ge(R1)(R2)—*′,
- T3 and T4 are each independently a single bond, *—O—*′, *—S—*′, *—C(R3)(R4)—*′, *—C(R3)═*′, *═C(R3)—*′, *—C(R3)═C(R4)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R3)—*′, *—N(R3)—*′, *—P(R3)—*′, *—Si(R3)(R4)—*′, *—P(R3)(R4)—*′ or *—Ge(R3)(R4)—*′,
- n1 to n4 are each independently 1, 2, or 3,
- X1 is N, P, C(R5), or Si(R5),
- X2 is N, P, C(R6), or Si(R6),
- L10 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,
- a10 is 1, 2, 3, 4, or 5,
- * and *′ each indicate a binding site to a neighboring atom,
- R1 to R6, R10, R20, R30, R40, R50, R60, R70, and R80 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 R10a, a C1-C60alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio 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),
- b10, b20, b30, b40, b50, b60, b70, and b80 are each independently an integer from 0 to 20,
- each of:
- R1 and R2;
- R3 and R4;
- two or more of R10 in the number of b10;
- two or more of R20 in the number of b20;
- two or more of R30 in the number of b30;
- two or more of R40 in the number of b40;
- two or more of R50 in the number of b50;
- two or more of R60 in the number of b60;
- two or more of R70 in the number of b70;
- and two or more of R80 in the number of b80 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,
- two or more of R1, R2, R10, R20, R50, and R60 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,
- two or more of R3, R4, R30, R40, R70, and R80 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,
- R10a is:
- deuterium, —F, —Cl, —Br, 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, a C1-C60 alkoxy group, or a C1-C60 alkylthio 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, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, or a C2-C60 heteroarylalkyl 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 C1-C60 alkylthio group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C3-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a 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:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- or 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 C7-C60 arylalkyl group, or a C2-C60 heteroaralkyl 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 a combination thereof.
43 more elements
Dependencies are inferred from the claim text.