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US 2019/0103568 A1Published application
Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound
AssigneeSamsung Electronics Co., Ltd.
InventorsKyuyoung HWANG, Seungyeon KWAK, Sunyoung LEE, Jungin LEE, Aram JEON, Yuri CHO, Seokhwan HONG, Ohyun KWON, Byoungki CHOI
Life of this patent
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Abstract
An organometallic compound represented by Formula 1:2 wherein, in Formula 1, groups and variables are the same as described in the specification.
Claims20
An organometallic compound represented by Formula 1:
- wherein, in Formula 1,
- M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
- X1 is N,
- X2 to X4 are each independently N or C,
- a bond between X1 and M is a covalent bond,
- two bonds selected from 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 remaining bond is a covalent bond,
- ring CY11 and ring CY12 are each independently a C5-C15 carbocyclic group or a C1-C15 heterocyclic group,
- ring CY2 to ring CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
- T1 and T2 are each independently selected from a single bond, a double bond, *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *—S—, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)═*′, *═C(R5)—*′, *—C(R5)═C(R6)—*, C(R5a)(R5b)—C(R6a)(R6b)—*′, *—C(═S)—*′, and *—C≡C—*′, and * and *′ each indicate a binding site to a neighboring atom,
- X15 is a single bond, O, S, Se, N(R15), C(R5)(R16), or Si(R15)(R16),
- R5 and R6, and R15 and R16 are optionally linked via a single bond, a double bond, or a first linking group to form a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein the C5-C30 carbocyclic group and the C1-C30 heterocyclic group are each unsubstituted or substituted with at least one R1a,
- R1 to R6, R5a, R5b, R6a, R6b, R15, and R16 are each independently selected from 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 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, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
- a1 to a4 are each independently an integer from 0 to 20,
- two or more groups selected from a plurality of neighboring groups R1 are optionally linked to form a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein the C5-C30 carbocyclic group and the C1-C30 heterocyclic group are each unsubstituted or substituted with at least one R1a,
- two or more groups selected from a plurality of neighboring groups R2 are optionally linked to form a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein the C5-C30 carbocyclic group and the C1-C30 heterocyclic group are each unsubstituted or substituted with at least one R1a,
- two or more groups selected from a plurality of neighboring groups R3 are optionally linked to form a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein the C5-C30 carbocyclic group and the C1-C30 heterocyclic group are each unsubstituted or substituted with at least one R1a,
- two or more groups selected from a plurality of neighboring groups R4 are optionally linked to form a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein the C5-C30 carbocyclic group and the C1-C30 heterocyclic group are each unsubstituted or substituted with at least one R1a,
- two or more groups selected from R1 to R6, R5a, R5b, R6a, R6b, R15, and R16 are optionally linked to form a C5-C30 carbocyclic group or a C1-C30 heterocyclic group, wherein the C5-C30 carbocyclic group and the C1-C30 heterocyclic group are each unsubstituted or substituted with at least one R1a,
- R1a is defined the same as above R1,
- 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, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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, 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, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), and —P(═O)(Q18)(Q19);
- 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;
- 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, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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, 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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), and —P(═O)(Q28)(Q29);
- and
- —N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), and —P(═O)(Q38)(Q39), and
- Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 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 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 C1-C60 alkyl group substituted with at least one selected from deuterium, a C1-C60 alkyl group, and a C6-C60 aryl 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 selected from deuterium, a C1-C60 alkyl group, and 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.
24 more elements
Dependencies are inferred from the claim text.