Near-infrared light-emitting diode and device including near-infrared light-emitting diode

A near-infrared light-emitting diode comprising:

• a first electrode;
• a second electrode;
• and
• an organic layer between the first electrode and the second electrode,
• wherein the organic layer comprises a near-infrared light-emitting layer, the near-infrared light-emitting layer comprises an osmium (Os)-containing organometallic compound, and the osmium (Os)-containing organometallic compound is configured to emit near-infrared light,
• wherein the osmium (Os)-containing organometallic compound is represented by Formula 1:
• M(L1)n1(L2)n2 Formula 1
• wherein, in Formula 1,
• M is Os,
• wherein L1 is selected from ligands represented by Formula 1-1(1):
• wherein, in Formula 1-1(1),
• ring A1, ring A2 and ring A10 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
• Z31 and Z32 are each independently a covalent bond, a coordinate bond, O, S, C(R7)(R8), Si(R7)(R8), N(R7), P(R7), C(R7)(R8)(R9), Si(R7)(R8)(R9), N(R7)(R8), or P(R7)(R8),
• X1 and X2 are each independently C or N,
• R1, R2 and R7 to R9 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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), —C(═O)2(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
• two adjacent groups selected from R1, R2 and R7 to R9 are optionally bound to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
• R10a is defined the same as R1,
• b1, b2 and b10 are each independently an integer from 0 to 10,
• *1 and *2 each indicate a binding site to M in Formula 1,
• a bond between M and Z31 or X1 in Formula 1-1(1) and a bond between M and Z32 or X2 in Formula 1-1(1) are each independently a covalent bond or a coordinate bond and
• 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 hydrazine group, a hydrazone 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 hydrazine group, a hydrazone 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(Q1 1)(Q12)(Q13), —N(Q1 1)(Q12), —B(Q1 1)(Q12), —C(═O)2(Q11), —S(═O)2(Q1 1), and —P(═O)(Q1 1)(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, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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 hydrazine group, a hydrazone 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 WOW), —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)2(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22);
• and
• —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)2(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
• wherein 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 hydrazine group, a hydrazone 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 aryl group substituted with at least one C1-C60 alkyl group, a C6-C60 aryl group substituted with at least one C6-C60 aryl group, a terphenyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group, a C1-C60 heteroaryl group substituted with at least one C6-C60 aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and
• wherein, a moiety represented by
• in Formula 1-1(1) is selected from groups represented by Formulae A1-1 to A1-51 and A1-54 to A1-56, and
• wherein a moiety represented by
• in Formula 1-1(1) is selected from groups represented by Formulae A2-1 to A2-32, A2-34, A2-35, A2-37 and A2-41 to A2-50:
• wherein in Formulae A1-1 to A1-51 and A1-54 to A1-56,
• X1 and R1 are respectively the same as those defined in Formula 1-1(1),
• b12 is an integer from 0 to 2,
• b13 is an integer from 0 to 3,
• b14 is an integer from 0 to 4,
• b15 is an integer from 0 to 5,
• b16 is an integer from 0 to 6,
• b17 is an integer from 0 to 7,
• *′ indicates a binding site to Z31 in Formula 1-1(1), and
• * indicates a binding site to T1 in Formula 1-1(1),
• wherein in Formulae A2-1 to A2-32, A2-34, A2-35, A2-37 and A2-41 to A2-50,
• X2 and R2 are respectively the same as those defined with respect to Formula 1-1(1),
• X21 is selected from O, S, N(R21), C(R21)(R22), and Si(R21)(R22),
• R21 and R22 are each defined the same as R2,
• b22 is an integer from 0 to 2,
• b23 is an integer from 0 to 3,
• b24 is an integer from 0 to 4,
• b25 is an integer from 0 to 5,
• b26 is an integer from 0 to 6,
• b27 is an integer from 0 to 7,
• *′ indicates a binding site to Z32 in Formula 1-1(1), and
• * indicates a binding site to T1 in Formula 1-1(1).

A near-infrared light-emitting diode comprising:

• a first electrode;
• a second electrode;
• and
• an organic layer between the first electrode and the second electrode,
• wherein the organic layer comprises a near-infrared light-emitting layer, the near-infrared light-emitting layer comprises an osmium (Os)-containing organometallic compound, and the osmium (Os)-containing organometallic compound is configured to emit near-infrared light,
• wherein the osmium (Os)-containing organometallic compound is represented by Formula 1:
• M(L1)n1(L2)n2 Formula 1
• wherein, in Formula 1,
• M is Os,
• L1 is selected from ligands represented by Formula 1-1:
• n1 is an integer from 1 to 4;
• and when n1 is 2 or greater, at least two L1(s) are identical to or different from each other,
• L2 is an organic ligand,
• n2 is an integer from 0 to 4;
• and when n2 is 2 or greater, at least two L2(s) are identical to or different from each other,
• i) at least two selected from L1(s) in the number of n1, ii) at least two selected from L2(s) in the number of n2, or iii) at least one selected from Li (s) in the number of n1 and at least one selected from L2(s) in the number of n2 are optionally bound via a single bond, a double bond, *═N—*′, *—N═*′, *═C[(L3)a3-(R3)]—*′, *-C[(L3)a3-(R3)]=*′, *—N[(L3)a3-(R3)]—*′, *—B(R3)—*′, *—P(R3)—*′, *—C(R3)(R4)—*′, *—Si(R3)(R4)—*′, *—Ge(R3)(R4)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R3)═*′, *═C(R3)—*′, *—C(R3)═C(R4)—*′, *—C(═S)—*′, or *—C≡C—*′ to form a tridentate ligand, a tetradentate ligand, a pentadentate ligand, or a hexadentate ligand, and * and *′ each indicate a binding site to an adjacent atom,
• wherein, in Formula 1-1,
• ring A1 and ring A2 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
• Z31 and Z32 are each independently a covalent bond, a coordinate bond, O, S, C(R7)(R8), Si(R7)(R8), N(R7), P(R7), C(R7)(R8)(R9), Si(R7)(R8)(R9), N(R7)(R8), or P(R7)(R8),
• X1 and X2 are each independently C or N,
• ring A1 and T1;
• and T1 and ring A2 are each independently bound via a single bond or a double bond,
• T1 is a single bond, a double bond, *═N—*′, *—N═*′, *═C[(L5)a5-(R)]-′, *—C[(L5)a5-(R5)]═*′, *—N[(L5)a5-(R5)]—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *-5-*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *-5(═O)—′, *—S(═O)2—*′, *—C(R5)═*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═S)—*′, or *—C≡C—*′, wherein * and *′ each indicate a binding site to an adjacent atom,
• L3 and L5 are each independently a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10,
• a3 and a5 are each independently an integer from 1 to 5,
• R1 to R10 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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), —C(═O)2(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
• two adjacent groups selected from R1 to R10 are optionally bound to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
• R10a is defined the same as R10,
• b1 and b2 are each independently an integer from 0 to 10,
• *1 and *2 each indicate a binding site to M in Formula 1,
• a bond between M and Z31 or X1 in Formula 1-1 and a bond between M and Z32 or X2 in Formula 1-1 are each independently a covalent bond or a coordinate bond, and
• 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 hydrazine group, a hydrazone 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 hydrazine group, a hydrazone 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(Q1 1)(Q12), —B(Q11)(Q12), —C(═O)2(Q1 1), —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, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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 hydrazine group, a hydrazone 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)2(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22);
• and
• —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)2(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
• wherein 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 hydrazine group, a hydrazone 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 aryl group substituted with at least one C1-C60 alkyl group, a C6-C60 aryl group substituted with at least one C6-C60 aryl group, a terphenyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group, a C1-C60 heteroaryl group substituted with at least one C6-C60 aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and
• wherein, a moiety represented by
• in Formula 1-1 is selected from groups represented by Formulae A1-1 to A1-51 and A1-54 to A1-56, and
• wherein a moiety represented by
• in Formula 1-1 is selected from groups represented by Formulae A2-1 to A2-32, A2-34, A2-35, A2-37 and A2-41 to A2-50:
• wherein in Formulae A1-1 to A1-51 and A1-54 to A1-56,
• X1 and R1 are respectively the same as those defined in Formula 1-1,
• b12 is an integer from 0 to 2,
• b13 is an integer from 0 to 3,
• b14 is an integer from 0 to 4,
• b15 is an integer from 0 to 5,
• b16 is an integer from 0 to 6,
• b17 is an integer from 0 to 7,
• *′ indicates a binding site to Z31 in Formula 1-1, and
• * indicates a binding site to T1 in Formula 1-1,
• wherein in Formulae A2-1 to A2-32, A2-34, A2-35, A2-37 and A2-41 to A2-50,
• X2 and R2 are respectively the same as those defined with respect to Formula 1-1,
• X21 is selected from O, S, N(R21), C(R21)(R22), and Si(R21)(R22),
• R21 and R22 are each defined the same as R2,
• b22 is an integer from 0 to 2,
• b23 is an integer from 0 to 3,
• b24 is an integer from 0 to 4,
• b25 is an integer from 0 to 5,
• b26 is an integer from 0 to 6,
• b27 is an integer from 0 to 7,
• *′ indicates a binding site to Z32 in Formula 1-1, and
• * indicates a binding site to T1 in Formula 1-1,
• wherein the organic layer further comprises a visible light-emitting layer.