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US 2024/0196731 A1Published application
Light-emitting device including organometallic compound, electronic apparatus including the light-emitting device, and the organometallic compound
AssigneeSamsung Display Co., Ltd.
InventorsEunsoo Ahn, Soobyung Ko, Sujin Shin, Hyunjung Lee, Mina Jeon, Junghoon Han
Life of this patent
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Abstract
Embodiments provide an organometallic compound, a light-emitting device that includes the organometallic compound, and an electronic apparatus that includes the light-emitting device. The organometallic compound is represented by Formula 1, which is explained in the specification.
Claims20
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- an interlayer between the first electrode and the second electrode, the interlayer comprising an emission layer;
- and
- an organometallic compound represented by Formula 1:
- wherein in Formula 1,
- M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
- rings CY1 to CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
- X1 to X3 are each independently N or C,
- X41 is N or C(R41),
- X42 is N or C(R42),
- X43 is N or C(R43),
- X44 is N or C(R44),
- X45 is N or C(R45),
- L1 to L3, L41, and L42 are each independently *—C(R5)(R6)—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R5)—*′, *—N(R5)—*′, *—O—*′, *—P(R5)—*′, *—Si(R5)(R6)—*′, *—P(═O)(R5)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R5)(R6)—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
- n1 to n3 are each independently an integer from 0 to 5, wherein
- when n1 is 0, a group represented by *-(L1)n1-*′ is a single bond,
- when n2 is 0, a group represented by *-(L2)n2-*′ is a single bond,
- when n3 is 0, a group represented by *-(L3)n3-*′ is a single bond,
- when n1 is an integer from 2 to 5, a plurality of L1 (s) are identical to or different from each other,
- when n2 is an integer from 2 to 5, a plurality of L2(s) are identical to or different from each other, and
- when n3 is an integer from 2 to 5, a plurality of L3(s) are identical to or different from each other,
- n41 and n42 are each independently an integer from 1 to 5, wherein
- when n41 is an integer from 2 to 5, a plurality of L41(s) are identical to or different from each other, and
- when n42 is an integer from 2 to 5, a plurality of L42(s) are identical to or different from each other,
- R1 to R6 and R41 to R45 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- a1 to a4 are each independently an integer from 0 to 10,
- two or more of R1 to R6 are optionally bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
- 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, —Cl, —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, a C7-C60 arylalkyl group, a C2-C60 heteroaryl alkyl group, —Si(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, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl 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, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(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), —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;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- or a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C20 alkoxy group, a C3-C60 carbocyclic group, or a C1-C60 heterocyclic 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, or a combination thereof.
42 more elements
An organometallic compound represented by Formula 1:
- wherein in Formula 1,
- M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
- rings CY1 to CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
- X1 to X3 are each independently N or C,
- X41 is N or C(R41),
- X42 is N or C(R42),
- X43 is N or C(R43),
- X44 is N or C(R44),
- X45 is N or C(R45),
- L1 to L3, L41, and L42 are each independently *—C(R5)(R6)—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R5)—*′, *—N(R5)—*′, *—O—*′, *—P(R5)—*′, *—Si(R5)(R6)—*′, *—P(═O)(R5)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R5)(R6)—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
- n1 to n3 are each independently an integer from 0 to 5, wherein
- when n1 is 0, a group represented by *-(L1)n1-*′ is a single bond,
- when n2 is 0, a group represented by *-(L2)n2-*′ is a single bond,
- when n3 is 0, a group represented by *-(L3)n3-*′ is a single bond,
- when n1 is an integer from 2 to 5, a plurality of L1 (s) are identical to or different from each other,
- when n2 is an integer from 2 to 5, a plurality of L2(s) are identical to or different from each other, and
- when n3 is an integer from 2 to 5, a plurality of L3(s) are identical to or different from each other,
- n41 and n42 are each independently an integer from 1 to 5, wherein
- when n41 is an integer from 2 to 5, a plurality of L41(s) are identical to or different from each other, and
- when n42 is an integer from 2 to 5, a plurality of L42(s) are identical to or different from each other,
- R1 to R6 and R41 to R45 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(a)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- a1 to a4 are each independently an integer from 0 to 10,
- two or more of R1 to R6 are optionally bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
- 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, —Cl, —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, a C7-C60 arylalkyl group, a C2-C60 heteroaryl alkyl group, —Si(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, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl 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, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(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), —N(Q31)(Q32), —B(Q31)(032), —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;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- or a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C20 alkoxy group, a C3-C60 carbocyclic group, or a C1-C60 heterocyclic 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, or a combination thereof.
37 more elements
Dependencies are inferred from the claim text.