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US 12,628,548 B2Granted
Organometallic compound and organic light-emitting device including the same
AssigneeSamsung Display Co., Ltd.
InventorsSunwoo Kang, Sangho Jeon, Youngmi Cho
Life of this patent
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Abstract
An organometallic compound and an organic light-emitting device including the same.
Claims17
An organic light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- an organic layer between the first electrode and the second electrode and comprising an emission layer;
- and
- at least one of an organometallic compound represented by Formula 1:
- M(L1)n1(L2)n2 <Formula 1>
- wherein, in Formula 1,
- M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
- in Formula 1, L1 is a ligand represented by Formula 2-2, and n1 is 2 or 3, wherein, when n1 is 2 or more, two or more L1(s) are identical to or different from each other,
- in Formula 1, L2 is a ligand represented by Formula 3, and n2 is 0, 1, or 2, wherein, when n2 is 2, two or more L2(s) are identical to or different from each other,
- the sum of n1 and n2 in Formula 1 is 2 or 3,
- in Formula 1, L1(s) in the number of n1 and L2(s) in the number of n2 are optionally linked to each other via a single bond, a first linking group, a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group,
- the first linking group is selected from *″—N(R4)—*′″, *″—B(R4)—*′″, *″—P(R4)—*′″, *″—C(R4)(R5)—*′″, *″—Si(R4)(R5)—*′″, *″—Ge(R4)(R5)—*′″, *″—S—*′″, *″—Se—*′″, *″—O—*′″, *″—C(═O)—*′″, *″—S(═O)—*′″, *″—S(═O)2—*′″, *″—C(R4)═*′, *″═C(R4)—*′″, *″—C(R4)═C(R5)—*′″, *″—C(═S)—*′″, and *″—C≡C—*′″;
- in Formula 2-2, X11 and X12 are each C(R15), and X13 is N or C(R15),
- T21 in Formula 3 may be selected from *″—N(R24)—*′″, *″—B(R24)—*′″, *″—P(R24)—*′″, *″—C(R24)(R25)—*′″, *″—Si(R24)(R25)—*′″, *″—Ge(R24)(R25)—*′″, *″—S—*, *″—Se—*′″, *″O—*′″, *″—C(═O)—*′″, *″—S(═O)—*′″, *″—S(═O)2—*′″, *″—C(R24)═*′, *″═C(R24)—*′″, *″—C(R24)═C(R25)—*″, *″—C(═S)—*′″, and *″—C≡C—*′″;
- R4 and R5, R11 to R15, and R21 to R25 in Formulae 2-2 and 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
- b21 to b23 in Formula 3 are each independently an integer from 1 to 3, wherein, when b21 is 2 or more, two or more R21(s) are identical to or different from each other, when b22 is 2 or more, two or more R22(s) are identical to or different from each other, and when b23 is 2 or more, two or more R23(s) are identical to or different from each other,
- in Formulae 2-2 and 3, two neighboring substituents among R11 to R14, R15, R21(s) in the number of b21, R22(s) in the number of b22, R23(s) in the number of b23, R24, and R25 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,
- a21 in Formula 3 is an integer of 2 or 3, wherein two or more T21(s) are identical to or different from each other,
- * and *′ in Formula 2-1 and 2-2 each indicate a binding site to M in Formula 1, and *″ and *′″ in Formulae 1 and 3 each indicate a binding site to a neighboring atom, at least one 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 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
- 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22);
- and
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), and
- Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, and a cyano group, a C6-C60 aryl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, and a cyano group, a biphenyl group, and a terphenyl group.
24 more elements
An organometallic compound represented by Formula 1:
- M(L1)n1(L2)n2 <Formula 1>
- wherein, in Formula 1,
- M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
- in Formula 1, L1 is a ligand represented by Formula 2-2, and n1 is 2 or 3, wherein, when n1 is 2 or more, two or more L1(s) are identical to or different from each other,
- in Formula 1, L2 is a ligand represented by Formula 3, and n2 is 0, 1, or 2, wherein, when n2 is 2, two or more L2(s) are identical to or different from each other,
- the sum of n1 and n2 in Formula 1 is 2 or 3,
- L1(s) in the number of n1 and L2(s) in the number of n2 in Formula 1 are optionally linked to each other via a single bond or a first linking group,
- the first linking group may be selected from *″—N(R4)—*′″, *″—B(R4)—*′″, *″—P(R4)—*′″, *″—C(R4)(R5)—*′″, *″—Si(R4)(R5)—*′″, *″—Ge(R4)(R5)—*′″, *″—S—*′″, *″—Se—*′″, *″—O—*′″, *″—C(═O)—*′″, *″—S(═O)—*′″, *″—S(═O)2—*′″, *″—C(R4)═*′, *″═C(R4)—*′″, *″—C(R4)═C(R5)—*′″, *″—C(═S)—*′″, and *″—C≡C—*′″;
- X11 and X12 in Formula 2-2 are each C(R15), and X13 is N or C(R15),
- T21 in Formula 3 may be selected from *″—N(R24)—*′″, *″—B(R24)—*′″, *″—P(R24)—*′″, *″—C(R24)(R25)—*′″, *″—Si(R24)(R25)—*′″, *″—Ge(R24)(R25)—*′″, *″—S—*, *″—Se—*′″, *″O—*′″, *″—C(═O)—*′″, *″—S(═O)—*′″, *″—S(═O)2—*′″, *″—C(R24)═*′, *″═C(R24)—*′″, *″—C(R24)═C(R25)—*″, *″—C(═S)—*′″, and *″—C≡C—*′″;
- R4 and R5, R11 to R15, and R21 to R25 in Formulae 2-2 and 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
- b21 to b23 in Formula 3 are each independently an integer from 1 to 3, wherein, when b21 is 2 or more, two or more R21(s) are identical to or different from each other, when b22 is 2 or more, two or more R22(s) are identical to or different from each other, and when b23 is 2 or more, two or more R23(s) are identical to or different from each other,
- in Formulae 2-2 and 3, two neighboring substituents among R11 to R14, R15, R21(s) in the number of b21, R22(s) in the number of b22, R23(s) in the number of b23, R24, and R25 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,
- a21 in Formula 3 is an integer of 2 or 3, wherein two or more T21(s) are identical to or different from each other,
- * and *′ in Formula 2-2 each indicate a binding site to M in Formula 1, and *″ and *′″ in Formulae 1 and 3 each indicate a binding site to a neighboring atom,
- 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 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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
- 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22);
- and
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), and
- Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, and a cyano group, a C6-C60 aryl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, and a cyano group, a biphenyl group, and a terphenyl group.
20 more elements
Dependencies are inferred from the claim text.