Organometallic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsJunghoon Han, Soobyung Ko, Sungbum Kim, Eunsoo Ahn, Jaesung Lee, Hyunjung Lee
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 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 the organometallic compound, which is represented by Formula 1, as defined 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,
- M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), iridium (Ir), or osmium (Os),
- X1 to X4 are each independently C or N,
- a bond between X1 and M is a coordinate bond,
- one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M is a coordinate bond,
- the remainder of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M are each a covalent bond,
- ring CY1 to ring CY7 are each independently a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
- L1 to L3 are each independently a single bond, *—C(R8)(R9)—*′, *—C(R8)═*′, *═C(R8)—*′, *—C(R8)═C(R9)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R8)—*′, *—N(R8)—*′, *—O—*′, *—P(R8)—*′, *—Si(R8)(R9)—*′, *—P(═O)(R8)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′ or *—Ge(R8)(R9)—*′,
- n1 to n3 are each independently an integer from 1 to 3,
- T1 is *—C(Z11)(Z12)—*′ or *—Si(Z11)(Z12)—*′,
- T2 is *—N(Z13)—*′, *—O—*′, *—S—*′, *—C(Z13)(Z14)—*′, or *—Si(Z13)(Z14)—*′,
- b2 is 0, 1, or 2, wherein T2 is not present when b2 is 0,
- * and *′ each indicate a binding site to a neighboring atom,
- R1 to R9 and Z11 to Z14 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-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), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
- a1 to a7 are each independently an integer from 0 to 20,
- each of two or more of R1 in the number of a1;
- two or more of R2 in the number of a2;
- two or more of R3 in the number of a3;
- two or more of R4 in the number of a4;
- two or more of R5 in the number of a5;
- two or more of R6 in the number of a6;
- two or more of R7 in the number of a7;
- R8 and R9;
- Z11 and Z12;
- and Z13 and Z14, 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 to R4, R8, and R9 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, —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), —P(Q11)(Q12), —C(═O)(Q11), —S(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), —P(═S)(Q11)(Q12), or a 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), —P(Q21)(Q22), —C(═O)(Q21), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), —P(═S)(Q21)(Q22), or a combination thereof;
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or —P(═S)(Q31)(Q32), and
- 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;
- 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 a combination thereof.
An organometallic compound represented by Formula 1:
- wherein in Formula 1,
- M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), iridium (Ir), or osmium (Os),
- X1 to X4 are each independently C or N,
- a bond between X1 and M is a coordinate bond,
- one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M is a coordinate bond,
- the remainder of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M are each a covalent bond,
- ring CY1 to ring CY7 are each independently a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
- L1 to L3 are each independently a single bond, *—C(R8)(R9)—*′, *—C(R8)═*′, *═C(R8)—*′, *—C(R8)═C(R9)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R8)—*′, *—N(R8)—*′, *—O—*′, *—P(R8)—*′, *—Si(R8)(R9)—*′, *—P(═O)(R8)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′ or *—Ge(R8)(R9)—*′,
- n1 to n3 are each independently an integer from 1 to 3,
- T1 is *—C(Z11)(Z12)—*′ or *—Si(Z11)(Z12)—*′,
- T2 is *—N(Z13)—*′, *—O—*′, *—S—*′, *—C(Z13)(Z14)—*′, or *—Si(Z13)(Z14)—*′,
- b2 is 0, 1, or 2, wherein T2 is not present when b2 is 0,
- * and *′ each indicate a binding site to a neighboring atom,
- R1 to R9 and Z11 to Z14 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-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), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
- a1 to a7 are each independently an integer from 0 to 20,
- each of two or more of R1 in the number of a1;
- two or more of R2 in the number of a2;
- two or more of R3 in the number of a3;
- two or more of R4 in the number of a4;
- two or more of R5 in the number of a5;
- two or more of R6 in the number of a6;
- two or more of R7 in the number of a7;
- R8 and R9;
- Z11 and Z12;
- and Z13 and Z14, 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 to R4, R8, and R9 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, —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), —P(Q11)(Q12), —C(═O)(Q11), —S(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), —P(═S)(Q11)(Q12), or a 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), —P(Q21)(Q22), —C(═O)(Q21), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), —P(═S)(Q21)(Q22), or a combination thereof;
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or —P(═S)(Q31)(Q32), and
- 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;
- 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 a combination thereof.
Dependencies are inferred from the claim text.