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US 12,713,828 B2Granted
Light-emitting device including organometallic compound, electronic apparatus including the light-emitting device, and the organometallic compound
AssigneeSamsung Display Co., Ltd.
InventorsMina Jeon, Soobyung Ko, Eunsoo Ahn, Jaesung Lee, Hyunjung Lee, Junghoon Han
Life of this patent
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Abstract
A light-emitting device including an organometallic compound represented by Formula 1, an electronic apparatus including the light-emitting device, and the organometallic compound are provided in the present application. The detailed description of Formula 1 is the same as described 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 and comprising an emission layer, and
- an organometallic compound represented by Formula 1:
- wherein, in Formula 1,
- M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium, or thulium, ring CY1, ring CY21, and ring CY23 are each independently a C3-C30 carbocyclic group or a C1-C30 heterocyclic group,
- ring CY22 is a C1-C30 heterocyclic group,
- X1, and X21 to X23 are each independently C or N, L1 to L3 are each independently a single bond, *—C(R1a)(R1b)—*′, *—C(R1a)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1a)—*′, *—N(R1a)—*′, * O—*′, *—P(R1a)(R1b)—*′, *—Si(R1a)(R1b)*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2*′, or *—Ge(R1a)(R1b)—*′,
- T1 is a single bond, *—C(R2a)(R2b)—*′, *—C(R2a)═*′, *═C(R2a)—*′, *—C(R2a)═C(R2b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R2a)—*′, *—N(R2a)—*′, *—O—*′, *—P(R2a)(R2b)—*′, *—Si(R2a)(R2b)—*′, *—P(═O)(R2a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R2a)(R2b)*′,
- T2 is a single bond, *—C(R3a)(R3b)—*′, *—C(R3a)═*′, *═C(R3a)—*′, *—C(R3a)═C(R3b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R3a)—*′, *—N(R3a)—*′, *—O—*′, *—P(R3a)(R3b)—*′, *—Si(R3a)(R3b)—*′, *—P(═O)(R3a)—*′, *—S—*′, *—S(═O)*′, *—S(═O)2—*′, or *—Ge(R3a)(R3b)*′,
- * and *′ each indicate a binding site to a neighboring atom,
- n1 to n3 are each independently an integer selected from 1 to 5,
- m1 is an integer selected from 0 to 2, wherein, when m1 is 0, T1 does not exist and thus ring CY1 and ring CY23 are not bound to each other,
- m2 is 1 or 2,
- Y1 is C(Z1) or N,
- Y2 is C(Z2) or N,
- Y3 is C(Z3) or N,
- Y4 is C(Z4) or N,
- Y5 is C(Z5) or N,
- Y6 is C(Z6) or N,
- Y7 is C(Z7) or N,
- Y8 is C(Z8) or N,
- R1, R21, R23, Z1 to Za, R1a, R1b, R2a, R2b, R3a, and R3b 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 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, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- a1, a21 and a23 are each independently an integer selected from 0 to 10,
- in Formula 1 indicates a single bond or a double bond,
- Z1 and Z2 are optionally bound 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,
- Z3 and Z4 are optionally bound 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,
- Z5 and Z6 are optionally bound 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,
- Z7 and Z8 are optionally bound 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,
- R2a and R2b are optionally bound 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,
- R3a and R3b are optionally bound 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,
- one selected from among R2a and R2b and one of R1(s) in the number of a1 are optionally bound 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,
- one selected from among R2a and R2b and one of R23(s) in the number of a23 are optionally bound 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,
- one selected from among R3a and R3b and one of R21(s) in the number of a21 are optionally bound 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,
- one selected from among R3a and R3b and one of R23(s) in the number of a23 are optionally bound 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, 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-C60 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), —O(Q31), —S(Q31), —P(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;
- hydroxyl group;
- 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 unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof;
- or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C60 heteroaryl alkyl 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
49 more elements
An organometallic compound represented by Formula 1:
- wherein, in Formula 1,
- M is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium, or thulium,
- ring CY1, ring CY21, and ring CY23 are each independently a C3-C30 carbocyclic group or a C1-C30 heterocyclic group,
- ring CY22 is a C1-C30 heterocyclic group,
- X1, and X21 to X23 are each independently C or N,
- L1 to L3 are each independently a single bond, *—C(R1a)(R1b)—*′, *—C(R1a)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1a)—*′, *—N(R1a)—*′, *—O—*′, *—P(R1a)(R1b)—*′, *—Si(R1a)(R1b)*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2*′, or *—Ge(R1a)(R1b)—*′,
- T1 is a single bond, *—C(R2a)(R2b)—*′, *—C(R2a)═*′, *═C(R2a)—*′, *—C(R2a)═C(R2b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R2a)—*′, *—N(R2a)—*′, *—O—*′, *—P(R2a)(R2b)—*′, *—Si(R2a)(R2b)—*′, *—P(═O)(R2a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R2a)(R2b)*′,
- T2 is a single bond, *—C(R3a)(R3b)—*′, *—C(R3a)═*′, *═C(R3a)—*′, *—C(R3a)═C(R3b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R3a)—*′, *—N(R3a)—*′, *—O—*′, *—P(R3a)(R3b)—*′, *—Si(R3a)(R3b)—*′, *—P(═O)(R3a)—*′, *—S—*′, *—S(═O)*′, *—S(═O)2—*′, or *—Ge(R3a)(R3b)*′,
- * and *′ each indicate a binding site to a neighboring atom,
- n1 to n3 are each independently an integer selected from 1 to 5,
- m1 is an integer selected from 0 to 2, wherein, when m1 is 0, T1 does not exist and thus ring CY1 and ring CY23 are not bound to each other,
- m2 is 1 or 2,
- Y1 is C(Z1) or N,
- Y2 is C(Z2) or N,
- Y3 is C(Z3) or N,
- Y4 is C(Z4) or N,
- Y5 is C(Z5) or N,
- Y6 is C(Z6) or N,
- Y7 is C(Z7) or N,
- Y8 is C(Z8) or N,
- R1, R21, R23, Z1 to Z8, R1a, R1b, R2a, R2b, R3a, and R3b 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 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, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- a1, a21 and a23 are each independently an integer selected from 0 to 10,
- in Formula 1 indicates a single bond or a double bond,
- Z1 and Z2 are optionally bound 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,
- Z3 and Z4 are optionally bound 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,
- Z5 and Z6 are optionally bound 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,
- Z7 and Z8 are optionally bound 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,
- R2a and R2b are optionally bound 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,
- R3a and R3b are optionally bound 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,
- one selected from among R2a and R2b and one of R1(s) in the number of a1 are optionally bound 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,
- one selected from among R2a and R2b and one of R23(s) in the number of a23 are optionally bound 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,
- one selected from among R3a and R3b and one of R21(s) in the number of a21 are optionally bound 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,
- one selected from among R3a and R3b and one of R23(s) in the number of a23 are optionally bound 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, 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-C60 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), —O(Q31), —S(Q31), —P(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;
- hydroxyl group;
- 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 unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof;
- or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 arylalkyl group, or a C2-C00 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C6 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
47 more elements
Dependencies are inferred from the claim text.