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Organometallic compound and organic light-emitting device including the same

專利號(hào)
US12137604B2
公開日期
2024-11-05
申請(qǐng)人
Samsung Electronics Co., Ltd.（KR Gyeonggi-Do）
發(fā)明人
Soyeon Kim; Ohyun Kwon; Jiyoun Lee; Yongsuk Cho; Jongwon Choi; Dmitry Kravchuk; Seungyeon Kwak; Myungsun Sim; Sunghun Lee
IPC分類
H01L51/00; C07F15/00; C09K11/06; H10K85/30; H10K50/11; H10K101/10
技術(shù)領(lǐng)域
group,c60,c1,c10,alkyl,or,c20,c30,c3,formula
地域： Suwon-si

摘要

Provided are an organometallic compound represented by Formula 1 and an organic light-emitting device including the same: wherein, in Formula 1, Y1, Y2, Xa, Xb, ring CY1, ring CY2, R1, R2, A1 to A7, a1, and a2 are as defined in the specification.

說明書

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0171890, filed on Dec. 20, 2019, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference.

BACKGROUND 1. Field

One or more embodiments relate to an organometallic compound and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices, which have better characteristics in terms of a viewing angle, response time, brightness, driving voltage, and response speed, and produce full-color images.

In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.

SUMMARY

Aspects of the present disclosure provide an organometallic compound and an organic light-emitting device including the same.

權(quán)利要求

1
What is claimed is:1. An organometallic compound represented by Formula 1:embedded imagewherein, in Formula 1, Y1 is N, Y2 is C, and ring CY1 is a group represented by Formula 1-1 or 1-2,embedded imagein Formulae 1, 1-1 and 1-2, ring CY2, ring CY11 and ring CY12 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,in Formula 1, Xa is N or C(Ta), and Xb is N or C(Tb),in Formula 1-1, X1 is N or C(R11), and X2 is N or C(R12),in Formulae 1-1 and 1-2, * and *′ are condensation sites to the adjacent 6-membered ring of Formula 1,a group represented byembedded image?is a group represented by one of Formulae 3-1 to 3-36 and 3-38 to 3-48:embedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imagewherein, in Formulae 3-1 to 3-36 and 3-38 to 3-48,Xa is C(Ta), and Xb is C(Tb), or Xa is N and Xb is N,a19 is an integer of 0 to 12,a18 is an integer of 0 to 8,a17 is an integer of 0 to 7,a16 is an integer of 0 to 6,a15 is an integer of 0 to 5,a14 is an integer of 0 to 4,* is a binding site to Ir in Formula 1, and*″ is a binding site to an adjacent atom in Formula 1,in Formulae 1, R1, R2, Ta, Tb, and A1 to A7 are each independently 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 C2-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), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),R11 and R12 are the same as defined above in connection with R1,a1 is an integer of 1 to 20, and when a1 is 2 or greater, two or more of R1(s) are identical to or different from each other,a2 is an integer of 0 to 20, and when a2 is 2 or greater, two or more of R2(s) are identical to or different from each other,at least one of R1(s) in number of a1 is 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 C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,two or more of R1(s) in number of a1 are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a,two or more of R2(s) in number of a2 are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a,R1 and R2 are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a,two or more of A1 to A7 are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a,R1a is the same as defined in connection with A7,a 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 C2-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: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 or a C1-C60 alkoxy group;a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —C1, —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 C2-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), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with 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 C2-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), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); orany combination thereof, andQ1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 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 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 unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; 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 C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.2. The organometallic compound of claim 1, wherein, in Formula 1, ring CY2 is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group, andin Formulae 1-1 and 1-2, ring CY11 and ring CY12 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a quinazoline group, or a quinoxaline group.3. The organometallic compound of claim 1, wherein R1, R2, Ta, Tb, and A1 to A7 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted phenyl group, —Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5).4. The organometallic compound of claim 1, wherein R1, R2, Ta, Tb, and A1 to A7 are each independently:hydrogen or deuterium;a C1-C30 alkyl group, a C3-C10 cycloalkyl group, or a phenyl group, each unsubstituted or substituted with deuterium, a C1-C30 alkyl group, a deuterated C1-C30 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or any combination thereof; or—Si(Q3)(Q4)(Q5), or —Ge(Q3)(Q4)(Q5).5. The organometallic compound of claim 1, wherein, in Formula 1, at least one of R1(s) in number of a1 is a group having three or more carbons.6. The organometallic compound of claim 1, wherein, in Formula 1, at least one of R1(s) in number of a1 is a C1-C30 alkyl group, a C3-C10 cycloalkyl group, or a phenyl group, each unsubstituted or substituted with deuterium, a C1-C30 alkyl group, a deuterated C1-C30 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or any combination thereof.7. The organometallic compound of claim 1, wherein, in Formula 1, at least one of R1(s) in number of a1 is a group represented by Formula 2:embedded imagewherein, in Formula 2, R31 to R33 are each independently hydrogen, deuterium, a C1-C30 alkyl group, a deuterated C1-C30 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, or a biphenyl group; and * is a binding site to an adjacent atom.8. The organometallic compound of claim 7, wherein the group represented by Formula 2 satisfies at least one of <Condition A> and <Condition B>:<Condition A>in Formula 2, two or more of R31 to R33 are each independently a C1-C30 alkyl group, a deuterated C1-C30 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, or a biphenyl group; and<Condition B>in Formula 2, one or more of R31 to R33 are each independently a C2-C30 alkyl group, a deuterated C2-C30 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, or a biphenyl group.9. The organometallic compound of claim 1, wherein, in Formula 1, the number of carbons in a group represented by *—C(A1)(A2)(A3) is 5 or greater, and the number of carbons in a group represented by *—C(A4)(A5)(A6) is 5 or greater.10. The organometallic compound of claim 1, wherein the organometallic compound satisfies at least one of <Condition 1> to <Condition 3>:<Condition 1>A1 to A6 in Formula 1 are each independently a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;<Condition 2>at least one of A1 to A6 in Formula 1 is a substituted or unsubstituted C2-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group; and<Condition 3>A7 in Formula 1 is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.11. The organometallic compound of claim 1, wherein the organometallic compound satisfies at least one of <Condition 4> and <Condition 5>:<Condition 4>in Formula 1, two or more of A1 to A3 of the group represented by *—C(A1)(A2)(A3) are linked with C in the group represented by *—C(A1)(A2)(A3) to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a; and<Condition 5>In Formula 1, two or more of A4 to A6 of the group represented by *—C(A4)(A5)(A6) are linked with C in the group represented by *—C(A4)(A5)(A6) to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1a.12. The organometallic compound of claim 1, wherein, in Formula 1, a group represented byembedded imageis a group represented by one of Formulae 4-1 to 4-60 and 4-97 to 4-126:embedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imagewherein, in Formulae 4-1 to 4-126,Y1, Xa, and Xb are the same as defined in claim 1,R11 to R18 are each independently 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 C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,* is a binding site to Ir in Formula 1, and*″ is a binding site to an adjacent atom in Formula 1.13. The organometallic compound of claim 1, wherein, in Formula 1, a group represented byembedded imageis a group represented by one of Formulae CY2-1 to CY2-7:embedded imageembedded imagewherein, in Formulae CY1-1 to CY2-7,Y2 is C,X21 is O, S, N(R28), C(R28)(R29), or Si(R28)(R29),R20 to R29 are the same as defined in connection with R2 in claim 1,*′ is a binding site to Ir in Formula 1, and*″ is a binding site to an adjacent atom in Formula 1.14. The organometallic compound of claim 13, wherein, in Formula CY2-1, R20 and R22 are each independently a C1-C30 alkyl group, a C3-C10 cycloalkyl group, or a phenyl group, each unsubstituted or substituted with deuterium, a C1-C30 alkyl group, a deuterated C1-C30 alkyl group, a C3-C10 cycloalkyl group, a deuterated C3-C10 cycloalkyl group, a (C1-C20 alkyl)C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or any combination thereof.15. The organometallic compound of claim 1, wherein the organometallic compound is at least one of Compounds 1 to 48:embedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded imageembedded image16. An organic light-emitting device comprising:a first electrode;a second electrode; andan organic layer disposed between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer includes at least one organometallic compound represented by Formula 1 of claim 1.17. The organic light-emitting device of claim 16, whereinthe first electrode is an anode,the second electrode is a cathode,the organic layer further comprises a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode,the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer or any combination thereof, andthe electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.18. The organic light-emitting device of claim 16, wherein the organometallic compound is in the emission layer.19. The organic light-emitting device of claim 18, wherein the emission layer further comprises a host, and an amount of the host in the emission layer is larger than an amount of the organometallic compound in the emission layer.
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