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US 2021/0171548 A1Published application
Organometallic compound, organic light-emitting device including organometallic compound and electronic apparatus including the organic light-emitting device
AssigneeSamsung Electronics Co., Ltd.
InventorsMinsik MIN, Hyejin BAE, Soonok JEON, Inkoo KIM, Jong soo KIM, Sungho NAM, Hyeonho CHOI
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Abstract
Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound and an electronic apparatus including the organic light-emitting device: Formula 1 may be understood by referring to the descriptions of Formula 1 provided herein.
Claims20
An organometallic compound represented by Formula 1:
- wherein, M in Formula 1 is a transition metal,
- X1 to X4 in Formula 1 are each independently C or N,
- in Formula 1, two of a bond between X1 and M, a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M are each a coordinate bond, and the rest are each a covalent bond,
- Z1 to Z4 in Formula 1 are each independently a group represented by Formula 2:
- b1 to b4 in Formula 1 are each independently an integer from 0 to 20, and the sum of b1 to b4 is 1 or greater,
- ring CY1 to ring CY4 in Formula 1 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
- T1 in Formula 1 is a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5a)=*′, *═C(R5a)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, *—C≡C—*′, 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,
- T2 in Formula 1 is a single bond, a double bond, *—N(R6a)—*′, *—B(R6a)—*′, *—P(R6a)—*′, *—C(R6a)(R6b)—*′, *—Si(R6a)(R6b)—*′, *—Ge(R6a)(R6b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R7a)═*′, *═C(R7a)—*′, *—C(R7a)═C(R7b)—*′, *—C(═S)—*′, *—C≡C—*′, 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,
- T3 in Formula 1 is a single bond, a double bond, *—N(R7a)—*′, *—B(R7a)—*′, *—P(R7a)—*′, *—C(R7a)(R7b)—*′, *—Si(R7a)(R7b)—*′, *—Ge(R7a)(R7b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R7a)—*′, *=C(R7a)—*′, *—C(R7a)═C(R7b)—*′, *—C(═S)—*′, *—C≡C—*′, 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,
- T4 in Formula 1 is a single bond, a double bond, *—N(R5a)—*′, *—B(R5a)—*′, *—P(R5a)—*′, *—C(R5a)(R5b)—*′, *—Si(R8a)(R8b)—*′, *—Ge(R8a)(R8b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5a)═*′, *=C(R5a)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, *—C≡C—*′, 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,
- n1 to n4 in Formula 1 are each independently an integer from 0 to 5, and at least three of n1 to n4 are each independently an integer from 1 to 5,
- in Formula 1, when n1 is 0, T1 is not present, when n2 is 0, T2 is not present, when n3 is 0, T3 is not present, and when n4 is 0, T4 is not present,
- in Formula 1, when n1 is 2 or greater, at least two T1(s) are identical to or different from each other, when n2 is 2 or greater, at least two T2(s) are identical to or different from each other, when n3 is 2 or greater, at least two T3(s) are identical to or different from each other, and when n4 is 2 or greater, at least two T4(s) are identical to or different from each other,
- R1 to R4, R5a, R5b, R6a, R6b, R7a, R7b, R8a, R8b, and Q51 to Q53 in Formulae 1 and 2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 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 C1-C60 alkylthio 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 unsaturated C1-C10 heterocyclic group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl 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 C2-C60 alkyl 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), and none of Q51 to Q53 in Formula 2 is hydrogen,
- at least one of Q51 to Q53 in Formula 2 is independently a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
- a1 to a4 in Formula 1 are each independently an integer from 0 to 20,
- L1 in Formula 2 is a single bond, 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,
- c1 in Formula 2 is an integer from 1 to 10,
- c2 in Formula 2 is an integer from 1 to 20,
- at least two R1(s) in the number of al in Formula 1 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,
- at least two R2(s) in the number of a2 in Formula 1 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,
- at least two R3(s) in the number of a3 in Formula 1 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,
- at least two R4(s) in the number of a4 in Formula 1 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,
- at least two of R1 to R4, R5a, R5b, R6a, R6b, R7a, R7b, R8a, and R8b 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 understood by referring to the description of R1 provided herein,
- * and *′ each indicate a binding site to an adjacent atom, and
- 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 C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted unsaturated C1-C10 heterocyclic group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl 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 C1-C60 alkoxy group, each 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 C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, an unsaturated C1-C10 heterocyclic 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, an unsaturated C1-C10 heterocyclic 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, an unsaturated C1-C10 heterocyclic 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(Q39)(Q39), or
- any combination thereof,
- wherein Q1 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;
- an unsaturated C1-C10 heterocyclic 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.
58 more elements
Dependencies are inferred from the claim text.