Light-emitting device including organometallic compound, electronic apparatus including the light-emitting device, and the organometallic compound

An electronic apparatus comprising a light-emitting device,

• wherein the light-emitting device comprises:
• a first electrode;
• a second electrode opposite to the first electrode;
• an interlayer between the first electrode and the second electrode and comprising an emission layer, and
• wherein the interlayer comprises an organometallic compound represented by Formula 1:
• wherein, in Formulae 1 and 1 Å,
• M1 is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
• X1 to X4 are each independently carbon (C) or nitrogen (N),
• ring CY1 to ring CY3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
• ring CY4 is a group represented by Formula 1 Å,
• ring A1 to ring A3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
• wherein at least one selected from among ring A1 to ring A3 is a condensed ring in which two or more rings are condensed with each other,
• Y1, Y2, Y4, Y5, Y7, and Y8 are each independently C or N,
• Y3 and Y6 are each C,
• L1 to L3 are each independently a single bond, *—C(R1a)(R1b)—*′, *—C(R1a)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1a)—*′, *—N(R1a)—*′, *—O—*′, *—P(R1a)—*′, *—Si(R1a)(R1b)—*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O )—*′, *—S(═O)2—*′, or *—Ge(R1a)(R1b)—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
• n1 to n3 are each independently an integer of 1 to 3,
• R1 to R4, R1a, and R1b 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), —Ge(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
• two or more of a plurality of R1 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
• two or more of a plurality of R2 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
• two or more of a plurality of R3 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
• two or more of a plurality of R4 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a1 to a4 are each independently an integer of 1 to 10,
• * indicates a binding site to M1,
• *′ indicates a binding site to a neighboring atom,
• R10a is:
• deuterium, —F, —CI, —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, —CI, —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, —Si(Q11)(Q12)(Q13), —Ge(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q1), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
• a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —CI, —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, —Si(Q21)(Q22)(Q23), —Ge(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a combination thereof;
• or
• —Si(Q31)(Q32)(Q33), —Ge(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;
• —CI;
• —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, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a combination thereof;
• 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a combination thereof, and
• wherein the organometallic compound satisfies at least one selected from among Conditions 1 to 3:
• Condition 1
• in Formula 1 Å, the ring comprising Y1, Y2, Y3, and Y6 is an n-membered ring, and n is 5 or more;
• Condition 2
• in Formula 1 Å, the ring comprising Y3, Y4, Y5, and Y6 is an n-membered ring, and n is 5 or more;
• and
• Condition 3
• in Formula 1 Å, the ring comprising Y3, Y6, Y7, and Y8 is an n-membered ring, and n is 5 or more.

An organometallic compound represented by Formula 1:

• wherein, in Formulae 1 and 1 Å,
• M1 is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
• X1 to X4 are each independently carbon (C) or nitrogen (N),
• ring CY1 to ring CY3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
• ring CY4 is a group represented by Formula 1 Å,
• ring A1 to ring A3 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
• wherein at least one selected from among ring A1 to ring A3 is a condensed ring in which two or more rings are condensed with each other,
• Y1, Y2, Y4, Y5, Y7, and Y8 are each independently C or N,
• Y3 and Y6 are each C,
• L1 to L3 are each independently a single bond, *—C(R1a)(R1b)—*′, *—C(R1a)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R1a)—*′, *—N(R1a)—*′, *—O—*′, *—P(R1a)—*′, *—Si(R1a)(R1b)—*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R1a)(R1b)—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
• n1 to n3 are each independently an integer of 1 to 3,
• R1 to R4, R1a, and R1b 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), —Ge(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
• two or more of a plurality of Ri are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
• two or more of a plurality of R2 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
• two or more of a plurality of R3 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
• two or more of a plurality of R4 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a1 to a4 are each independently an integer of 1 to 10,
• * indicates a binding site to M1,
• *′ indicates a binding site to a neighboring atom,
• 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, —CI, —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, —Si(Q11)(Q12)(Q13), —Ge(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
• a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio 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, —Si(Q21)(Q22)(Q23), —Ge(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a combination thereof;
• or
• —Si(Q31)(Q32)(Q33), —Ge(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;
• —C1;
• —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, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a combination thereof;
• 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a combination thereof, and
• wherein the organometallic compound satisfies at least one selected from among Conditions 1 to 3:
• Condition 1
• in Formula 1 Å, the ring comprising Y1, Y2, Y3, and Y6 is an n-membered ring, and n is 5 or more;
• Condition 2
• in Formula 1 Å, the ring comprising Y3, Y4, Y5, and Y6 is an n-membered ring, and n is 5 or more;
• and
• Condition 3
• in Formula 1 Å, the ring comprising Y3, Y6, Y7, and Y8 is an n-membered ring, and n is 5 or more.