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US 2022/0102652 A1Published application
Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
AssigneeSamsung Electronics Co., Ltd.
InventorsYong Joo Lee, Byungjoon Kang, Shingo ISHIHARA, Jeoungin Yi, Byoungki Choi, Yasushi KOISHIKAWA, Kyuyoung Hwang
Life of this patent
Estimating the term…
Abstract
An organometallic compound represented by Formula 1: M(L1)n1(L2)n2 Formula 1 wherein, in Formula 1, M, L1, L2, n1 and n2 are the same as described in the specification.
Claims20
An organometallic compound represented by Formula 1:
- M(L1)n1(L2)n2 Formula 1
- wherein, in Formula 1,
- M is a transition metal,
- L1 is a ligand represented by Formula 2A,
- L2 is a ligand represented by Formula 2B,
- n1 and n2 are each independently 1 or 2, wherein, when n1 is 2, two Li(s) are identical to or different from each other, and when n2 is 2, two L2(s) are identical to or different from each other,
- the sum of n1 and n2 is 2 or 3, and
- L1 and L2 are different from each other:
- wherein, in Formulae 2A and 2B,
- Y4 is C or N,
- X21 is O, S, Se, S(═O), N(R29), C(R29)(R30), or Si(R29)(R30),
- T1 to T4 are each independently C, N, carbon bonded to ring CY1, or carbon bonded to M in Formula 1, wherein one of T1 to T4 is the carbon bonded to M in Formula 1, and one of the remaining groups T1 to T4 that is not bonded to M in Formula 1 is the carbon bonded to ring CY1,
- T5 to T8 are each independently C or N,
- ring CY1 and ring CY3 are each independently a C1-C30 heterocyclic group,
- ring CY4 is a C3-C30 carbocyclic group or a C1-C30 heterocyclic group,
- Z1, Z3, and Z4 are each independently a fluoro group or a fluorinated group,
- Z2 is a fluoro group, a fluorinated non-cyclic group, or a fluorinated saturated cyclic group,
- a1, a3, and a4 are each independently an integer from 0 to 20, wherein a2 is an integer from 0 to 6, and the sum of a1, a2, a3, and a4 is 1 or more,
- R1 to R4, R29, and R30 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
- b1, b3, and b4 are each independently an integer from 0 to 20, and b2 is an integer from 0 to 6,
- when i) none of T1 to T8 in Formula 2 Å is N, ii) a2 in Formula 2 Å is not 0, and iii) Z2 in Formula 2 Å is a fluoro group, then a) b3 in Formula 2B is not 0, and b) at least one of R3(s) in the number of b3 in Formula 2B is —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5),
- two or more of a plurality of R1(s) are optionally linked together to form a C3-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
- two or more of a plurality of R2(s) are optionally linked together to form a C3-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
- two or more of a plurality of R3(s) are optionally linked together to form a O3—C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
- two or more of a plurality of R3(s) are optionally linked together to form a C3-C30 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R10a,
- R10a is the same as described in connection with R1,
- * and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1, and
- a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
- deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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;
- 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 independently substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or a combination thereof;
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or a combination thereof;
- —N(Q31) (Q32), —Si(Q33) (Q34) (Q35), —Ge(Q33) (Q34) (Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39), or
- a combination thereof,
- wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- an amino group;
- an amidino group;
- a hydrazine group;
- a hydrazone group;
- a carboxylic acid group or a salt thereof;
- a sulfonic acid group or a salt thereof;
- a phosphoric acid group or a salt thereof;
- a C1-C60 alkyl group which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof;
- a C2-C60 alkenyl group;
- a C2-C60 alkynyl group;
- a C1-C60 alkoxy group;
- a C1-C60 alkylthio group;
- a C3-C10 cycloalkyl group;
- a C1-C10 heterocycloalkyl group;
- a C3-C10 cycloalkenyl group;
- a C1-C10 heterocycloalkenyl group;
- a C6-C60 aryl group which is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof;
- a C6-C60 aryloxy group;
- a C6-C60 arylthio group;
- a C7-C60 arylalkyl group;
- a C1-C60 heteroaryl group;
- a C1-C60 heteroaryloxy group;
- a C1-C60 heteroarylthio group;
- a C2-C60 heteroarylalkyl group;
- a monovalent non-aromatic condensed polycyclic group;
- or a monovalent non-aromatic condensed heteropolycyclic group.
66 more elements
Dependencies are inferred from the claim text.