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US 2024/0196725 A1Published application
Organometallic compound, light-emitting device including the organometallic compound, electronic apparatus and electronic device including the light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsDongsun Yoo, Donguk Kang, Gyeongheon Kim, Seran Kim, Sohae Kim, Jihye Kim, Hoilim Kim, Saerom Park, Yongsub Shim
Life of this patent
Estimating the term…
Abstract
Provided are an organometallic compound represented by Formula 1, a light-emitting device including the organometallic compound, and an electronic apparatus and an electronic device that include the light-emitting device. In Formula 1, L1 may be a ligand represented by Formula 2, and Formulae 1 and 2 are described in more detail in the specification.
Claims20
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- an interlayer arranged between the first electrode and the second electrode;
- and
- an organometallic compound represented by Formula 1:
- wherein, in Formula 1, M is a transition metal,
- in Formula 1, L1 is a ligand represented by Formula 2, and n1 is 1, 2, or 3, wherein, when n1 is 2 or more, two or more of L1 are identical to or different from each other,
- in Formula 1, L2 is an organic ligand, and n2 is 0, 1 or 2, wherein, when n2 is 2 or more, two or more of L2 are identical to or different from each other,
- in Formula 1, a sum of n1 and n2 is 2 or 3,
- in Formula 2,
- Y1 is C or N,
- Y2 is C or N,
- Z1 is N(R11a), O, S, Se, C(R11a)(R11b), or Si(R11a)(R11b),
- ring CY11, ring CY12, and ring CY21 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein ring CY21 is not a group in which three or more cyclic groups are condensed together,
- R11, R12, R11a, R11b, 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 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),
- d11, d12, and d21 are each independently an integer from 0 to 20,
- at least two groups among R11, R12, R11a, R11b, and R21 are optionally bonded to together to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C2-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- * and *′ each indicate a binding site to M in Formula 1,
- 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 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 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 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 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 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), 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, 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 any combination thereof.
36 more elements
An organometallic compound represented by Formula 1:
- wherein, in Formula 1, M is a transition metal,
- in Formula 1, L1 is a ligand represented by Formula 2, and n1 is 1, 2, or 3, wherein, when n1 is 2 or more, two or more of L1 are identical to or different from each other,
- in Formula 1, L2 is an organic ligand, and n2 is 0, 1 or 2, wherein, when n2 is 2 or more, two or more of L2 are identical to or different from each other,
- in Formula 1, a sum of n1 and n2 is 2 or 3,
- in Formula 2,
- Y1 is C or N,
- Y2 is C or N,
- Z11 is N(R11a), O, S, Se, C(R11a)(R11b), or Si(R11a)(R11b),
- ring CY11, ring CY12, and ring CY21 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein ring CY21 is not a group in which three or more cyclic groups are condensed together,
- R11, R12, R11a, R11b, 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 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),
- d11, d12, and d21 are each independently an integer from 0 to 20,
- at least two groups among R11, R12, R11a, R11b, and R21 are optionally bonded to together to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C2-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- * and *′ each indicate a binding site to M in Formula 1,
- 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 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 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 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 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 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), 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, 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 any combination thereof;
- a C7-C60 arylalkyl group;
- or a C2-C60 heteroarylalkyl group.
33 more elements
Dependencies are inferred from the claim text.