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US 11,377,458 B2Granted
Organometallic compound and organic light-emitting device including the same
AssigneesSamsung Electronics Co., Ltd., Samsung SDI Co., Ltd.
InventorsJuhyun Kim, Wook Kim, Youngchun Kwon, Sangmo Kim, Changho Noh, Minsik Min, Sangho Park, Hyejin Bae, Wonseok Oh, Hasup Lee, Yongsik Jung, Younsuk Choi
Life of this patent
Estimating the term…
Abstract
An organometallic compound represented by Formula 1: M(L1)n1(L2)n2(L3)n3 Formula 1 wherein in Formula 1, M, L1, L2, L3, n1, n2, and n3 are the same as defined in the specification.
Claims17
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,
- in Formula 1, n1 is 1, 2, or 3, wherein, when n1 is two or more, two or more of groups L1 are identical to or different from each other,
- in Formula 1, L2 and L3 are each independently selected from a monodentate ligand, a bidentate ligand, a tridentate ligand, and a tetradentate ligand,
- in Formula 1, n2 and n3 are each independently 0, 1, 2, 3, or 4, wherein, when n2 is two or more, two or more of groups L2 are identical to or different from each other, and when n3 is two or more, two or more of groups L3 are identical to or different from each other,
- in Formula 2, X1 is C(R1) or N, X2 is C(R2) or N, X3 is C(R3) or N, and X4 is C(R4) or N,
- in Formulae 4A and 4B, X11 is C(R11) or N, X12 is C(R12) or N, and X13 is O, S, Se, N(R13), B(R13), P(R13), or C(R13)(R14),
- in Formulae 4A and 4B, when X11 is C(R11) and X12 is C(R12), R11 and R12 are not linked to each other,
- in Formulae 4A and 4B, represents a single bond or a double bond,
- in Formula 2, i) X1 is C(R1) and X2 is C(R2), wherein R1 and R2 are linked to each other to form ring CY2 represented by Formula 4A or 4B, ii) X2 is C(R2) and X3 is C(R3), wherein R2 and R3 are linked to each other to form ring CY2 represented by Formula 4A or 4B, or iii) X3 is C(R3) and X4 is C(R4), wherein R3 and R4 are linked to each other to form ring CY2 represented by Formula 4A or 4B,
- ring CY1 in Formula 2 and ring CY2 represented by Formula 4A or 4B are condensed with each other,
- a) when X2 in Formula 2 is C(R2) and X3 is C(R3), then R2 and R3 are linked to each other to form ring CY2 represented by Formula 4A or 4B, b) when X13 in Formula 4A and 4B is N(R13), then at least one of X11 and X12 in Formula 4A and 4B is N,
- in Formula 2,
- X2 is C(R2) and X3 is C(R3), wherein R2 and R3 are linked to each other to form ring CY2 represented by Formula 4A or 4B, wherein in Formulae 4A and 4B, X11 is N and X13 is N(R13), O, or S, or
- in Formula 2, X21 is C or N,
- ring CY21 is i) a first ring, ii) a second ring, iii) a ring in which at least two second rings are condensed with each other, or iv) a ring in which at least one first ring and at least one second rings are condensed with each other,
- the first ring is a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isozadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, and a triazasilole group,
- the second ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group,
- provided that when CY21 is a ring in which at least one first ring and at least one second rings are condensed with each other, then the at least one second ring is bound to M,
- R1 to R4, R11 to R14, and R21 are each independently selected from 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 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 C1-C60 heteroaryl 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), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
- a21 is an integer from 0 to 20,
- in formula 2, when ring CY21 is a C5-C30 carbocyclic group, then i) R21 is selected from —F, —Cl, —Br, —I, —SF5, a cyano group, a substituted or unsubstituted C1-C60 alkoxy 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 C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and ii) a21 is an integer from 1 to 20,
- two of a plurality of neighboring groups R21 are optionally linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- in Formula 2, * and *′ each indicate a binding site to M in Formula 1,
- at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, 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 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 C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
- 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, and a C1-C60 alkoxy group;
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), and —P(═O)(Q18)(Q19);
- 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), and —P(═O)(Q28)(Q29);
- and
- —N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), and —P(═O)(Q38)(Q39), and
- Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently selected from 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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy 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, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group, and a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and
- the organometallic compound emits blue light having a maximum emission wavelength in a range from 440 nanometers to 480 nanometers.
30 more elements
An organometallic compound of Compounds 1 to 12, 14 to 18, 20 to 30, and 32 to 38 below:
Dependencies are inferred from the claim text.