IP Library › Granted Patent US 12,501,821

Granted Patent B2

US 12,501,821 · App. 18/414,720 · Granted Dec 16, 2025

Organic light-emitting device and organometallic compound

Inventors: Soobyung Ko (Yongin-si, KR); Mina Jeon (Yongin-si, KR); Sungbum Kim (Yongin-si, KR); Sujin Shin (Yongin-si, KR); Eunsoo Ahn (Yongin-si, KR); Eunyoung Lee (Yongin-si, KR); Jaesung Lee (Yongin-si, KR); Jihyung Lee (Yongin-si, KR); Hyunjung Lee (Yongin-si, KR); Junghoon Han (Yongin-si, KR)

Assignee: Samsung Display Co., Ltd.

H10K85/346 C07F15/0086 C09K11/06 C07B2200/05 C09K2211/1044 C09K2211/1059 C09K2211/185 H10K50/11 H10K50/121 H10K2101/10 H10K2101/90

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Quick Facts

Patent No.: US 12,501,821
App. No.: 18/414,720
Granted: Dec 16, 2025
Kind: B2

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Abstract

Provided are an organometallic compound represented by Formula 1 and an organic light-emitting device including a first compound represented by Formula 1. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the first compound represented by Formula 1:

Claims (169)

1 . An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode and comprising an emission layer,

wherein the organic layer comprises a first compound represented by Formulae 1B or 1C:

wherein, in Formulae 1B and 1C,

M is Pt, Pd, or Au, and

L 2 is a monodentate ligand represented by Formula 2-1 or 2-2, wherein L 2 is none of —F, —Cl, —Br, and —I:

wherein, in Formulae 1B, 1C, 2-1, and 2-2,

X 1 to X 3 are C, and X 4 is N or C,

T 14 is a chemical bond, *—O—*′, *—S—*′, *—B(R′)—*′, *—N(R′)—*′, *—P(R′)—*′, *—C(R′)(R″)—*′, *—Si(R′)(R″)—*′, *—Ge(R′)(R″)—*′, *—C(═O)—*′, or *—C(═S)—*′,

T 15 is a chemical bond, *—O—*′, *—S—**′, * *—B(R′)-*′, *—N(R′)—*′, *—P(R′)—*′, *—C(R′)(R″)—*′, *—Si(R′)(R″)—*′, *—Ge(R′)(R″)—*′, *—C(═O)—*′, *—C(═S)—*′, *—O—C(═O)—*′, *—S—C(═O)—*′, *—O—C(═S)—*′, *—S—C(═S)—*′, *—C(R′)═C(R″)—*′, *—C═C—*′, *—C═C—C(═O)—*′, or *—C═C—C(═S)—*′,

when T 14 or T 15 is a chemical bond, X 4 or R 5 and M are directly linked to each other,

a bond between X 4 , T 14 , R 5 , or T 15 and M are each a coordinate bond or covalent bond,

T 1 is a single bond,

T 2 is a single bond,

ring CY 4 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

X 12 is N(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ),

X 21 is C(R 21 ), X 22 is C(R 22 ), X 23 is C(R 23 ),

X 32 is N(R 32 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), at least one of X 33 to X 36 is N,

R 4 , R 12 to R 16 , R 21 to R 23 , R 32 to R 36 , R′, and R″ 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 substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),

R 5 is 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 substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), wherein, when T 15 in Formula 2-2 is a chemical bond, R 5 is not —F, —Cl, —Br, and —I,

a4 is an integer from 0 to 20,

* and *′ each indicate a binding site to a neighboring atom,

a substituent(s) of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 7 -C 60 alkylaryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 2 -C 60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is (are):

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alkylaryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —O(Q 11 ), —S(Q 11 ), —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —P(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alkylaryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkylheteroaryl 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, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alkylaryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —O(Q 21 ), —S(Q 21 ), —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —P(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof;

—O(Q 31 ), —S(Q 31 ), —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ); or

any combination thereof, and

Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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; C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; C 2 -C 60 alkenyl group; C 2 -C 60 alkynyl group; C 1 -C 60 alkoxy group; C 3 -C 10 cycloalkyl group; C 1 -C 10 heterocycloalkyl group; C 3 -C 10 cycloalkenyl group; C 1 -C 10 heterocycloalkenyl group; C 6 -C 60 aryl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; C 6 -C 60 aryloxy group; C 6 -C 60 arylthio group; C 1 -C 60 heteroaryl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

2 . The organic light-emitting device of claim 1 , wherein,

the organic layer further comprises a second compound represented by Formula 2, a third compound comprising a group represented by Formula 3, or any combination thereof, and

the second compound is different from the third compound:

wherein, in Formulae 2 and 3,

ring CY 71 and ring CY 72 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

L 51 to L 53 are each independently a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a , R 10a is the same as defined in connection with R 1 , and R 10a is not hydrogen,

b51 to b53 are each independently an integer from 0 to 5, wherein, when b51 is 0, *-(L 51 ) b51 -*′ is a single bond, when b52 is 0, *-(L 52 ) b52 -*′ is a single bond, and when b53 is 0, *-(L 53 ) b53 -*′ is a single bond,

X 54 is N or C(R 54 ), X 55 is N or C(R 55 ), X 56 is N or C(R 56 ), and at least one of X 54 to X 56 is N,

X 81 is a single bond, O, S, N(R 81 ), B(R 81 ), C(R 81a )(R 81b ), or Si(R 81a )(R 81b ),

R 51 to R 56 , R 71 , R 72 , R 81 , R 81a , and R 81b 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 substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),

a71 and a72 are each independently an integer from 0 to 20,

* and *′ each indicate a binding site to a neighboring atom,

—O(Q 31 ), —S(Q 31 ), —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ); or

any combination thereof, and

3 . The organic light-emitting device of claim 1 , wherein,

in Formula 2-1,

ring CY 4 is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzoboracyclohexadiene group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a phenothiazine 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

4 . The organic light-emitting device of claim 1 , wherein,

at least one of R 21 to R 23 in Formulae 1B and 1C is a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

5 . The organic light-emitting device of claim 1 , wherein,

L 2 in Formulae 1B and 1C is a ligand represented by one of Formulae A4-1 (1) to A4-1 (4):

wherein, in Formulae A4-1 (1) to A4-1 (4),

X 4 is the same as described in claim 1 ,

X 40a is a single bond, O, S, S(═O) 2 , C(R 40a )(R 40b ), Si(R 40a )(R 40b ), N(R 40a ), or B(R 40a ),

X 40c is O, S, C(R 40c )(R 40d ), Si(R 40c )(R 40d ), or N(R 40c ),

X 40e is O, S, C(R 40e )(R 40f ), Si(R 40e )(R 40f ), or N(R 40e ),

X 40g is N, B, or P,

X 41 is N or C(R 41 ), X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), X 44 is N or C(R 44 ), X 45 is N or C(R 45 ), X 46 is N or C(R 46 ), X 47 is N or C(R 47 ), X 48 is N or C(R 48 ), and X 49 is N or C(R 49 ),

R 40a to R 40f and R 41 to R 49 are each independently the same as defined in connection with R 4 , and

* indicates a binding site to M in Formulae 1B or 1C.

6 . The organic light-emitting device of claim 1 , wherein,

in Formulae 1B and 1C, X 22 is C(R 22 ), and R 22 is a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkylaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

7 . The organic light-emitting device of claim 2 , wherein,

a group represented by *-(L 51 ) b51 -R 51 in Formula 2 is a group represented by one of Formulae CY 51 -1 to CY 51 -22,

a group represented by *-(L 52 ) b52 -R 52 in Formula 2 is a group represented by one of Formulae CY 52 -1 to CY 52 -22, and

a group represented by *-(L 53 ) b53 -R 53 in Formula 2 is a group represented by one of Formulae CY 53 -1 to CY 53 -18, —C(Q 1 )(Q 2 )(Q 3 ), or —Si(Q 1 )(Q 2 )(Q 3 ):

wherein, in Formulae CY51-1 to CY51-22, CY52-1 to CY52-22, and CY53-1 to CY53-18,

Y 63 is a single bond, O, S, N(R 63 ), B(R 63 ), C(R 63a )(R 63b ), or Si(R 63a )(R 63b ),

Y 64 is a single bond, O, S, N(R 64 ), B(R 64 ), C(R 64a )(R 64b ), or Si(R 64a )(R 64b ),

Y 67 is a single bond, O, S, N(R 67 ), B(R 67 ), C(R 67a )(R 67b ), or Si(R 67a )(R 67b ),

Y 68 is a single bond, O, S, N(R 68 ), B(R 68 ), C(R 68a )(R 68b ), or Si(R 68a )(R 68b ),

Y 63 and Y 64 in Formulae CY 51 -16 and CY 51 -17 are not a single bond at the same time,

Y 67 and Y 68 in Formulae CY 52 -16 and CY 52 -17 are not a single bond at the same time,

R 51a to R 51e , R 61 to R 64 , R 63a , R 63b , R 64a , and R 64b are each independently the same as defined in connection with R 51 in claim 2 , wherein each of R 51a to R 51e is not hydrogen,

R 52a to R 52e , R 65 to R 68 , R 67a , R 67b , R 68a , and R 68b are each independently the same as defined in connection with R 52 in claim 2 , wherein each of R 52a to R 52e is not hydrogen,

R 53a to R 53e are each independently the same as defined in connection with R 53 in claim 2 , wherein each of R 53a to R 53e is not hydrogen, and

* indicates a binding site to a neighboring atom.

8 . The organic light-emitting device of claim 2 , wherein,

the third compound is represented by one of Formulae 3-1 to 3-5:

wherein, in Formulae 3-1 to 3-5,

ring CY 71 , ring CY 72 , X 81 , R 71 , R 72 , a71, and a72 are each independently the same as described in claim 2 ,

ring CY 73 , ring CY 74 , R 73 , R 74 , a73, and a74 are each independently the same as defined in connection with ring CY 71 , ring CY 72 , R 71 , R 72 , a71, and a72 in claim 2 ,

L 81 is *—C(Q 4 )(Q 5 )-*′, *—Si(Q 4 )(Q 5 )-*′, a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a , wherein Q 4 and Q 5 are each independently the same as defined in connection with Q 1 in claim 2 ,

b81 is an integer from 0 to 5, wherein, when b81 is 0, *-(L 81 ) b81 -*′ is a single bond, and when b81 is 2 or more, two or more L 81 (s) are identical to or different from each other,

X 82 is a single bond, O, S, N(R 82 ), B(R 82 ), C(R 82a )(R 82b ), or Si(R 82a )(R 82b ),

X 83 is a single bond, O, S, N(R 83 ), B(R 83 ), C(R 83a )(R 83b ), or Si(R 83a )(R 83b ),

X 82 and X 83 in Formulae 3-2 and 3-4 are not a single bond at the same time,

X 84 is C or Si,

R 80 , R 82 , R 83 , R 82a , R 82b , R 83a , R 83b , and R 84 are each independently the same as defined in connection with R 81 in claim 2 ,

R 10a is the same as defined in claim 2 , and

* and *′ each indicate a binding site to a neighboring atom.

9 . The organic light-emitting device of claim 2 , wherein,

a group represented by

in Formulae 3-1 and 3-2 is a group represented by one of Formulae CY71-1 (1) to CY71-1 (8),

a group represented by

in Formulae 3-1 and 3-3 is a group represented by one of Formulae CY71-2 (1) to CY71-2 (8),

a group represented by

in Formulae 3-2 and 3-4 is a group represented by one of Formulae CY71-3 (1) to CY71-3 (32),

a group represented by

in Formulae 3-3 to 3-5 is a group represented by one of Formulae CY71-4 (1) to CY71-4 (32), and

a group represented by

in Formula 3-5 is a group represented by one of Formulae CY71-5 (1) to CY71-5 (8):

wherein, in Formulae CY71-1 (1) to CY71-1 (8), CY71-2 (1) to CY71-2 (8), CY71-3 (1) to CY71-3 (32), CY71-4 (1) to CY71-4 (32), and CY71-5 (1) to CY71-5 (8),

X 81 to X 84 , R 80 , and R 84 are each independently the same as described in claim 8 ,

X 85 is a single bond, O, S, N(R 85 ), B(R 85 ), C(R 85a )(R 85b ), or Si(R 85a )(R 85b ),

X 86 is a single bond, O, S, N(R 86 ), B(R 86 ), C(R 86a )(R 86b ), or Si(R 86a )(R 86b ),

X 85 and X 86 in Formulae CY71-1 (1) to CY71-1 (8) and CY71-4 (1) to CY71-4 (32) are not a single bond at the same time,

X 87 is a single bond, O, S, N(R 87 ), B(R 87 ), C(R 87a )(R 87b ), or Si(R 87a )(R 87b ),

X 88 is a single bond, O, S, N(R 88 ), B(R 88 ), C(R 88a )(R 88b ), or Si(R 88a )(R 88b ),

X 87 and X 88 in Formulae CY71-2 (1) to CY71-2 (8), CY71-3 (1) to CY71-3 (32), and CY71-5 (1) to CY71-5 (8) are not a single bond at the same time, and

R 85 to R 88 , R 85a , R 85b , R 86a , R 86b , R 87a , R 87b , R 88a , and R 88b are each independently the same as defined in connection with R 81 in claim 2 .

10 . The organic light-emitting device of claim 1 , wherein,

the emission layer comprises the first compound,

the emission layer further comprises a host,

the first compound and the host are different from each other, and

the emission layer is configured to emit blue light emitted from the first compound.

11 . The organic light-emitting device of claim 1 , wherein,

the emission layer comprises the first compound,

the emission layer further comprises a host and a dopant,

the first compound, the host, and the dopant are different from each other, and

the emission layer is configured to emit phosphorescence light or fluorescence light emitted from the dopant.

12 . An organometallic compound represented by Formulae 1B or 1C:

wherein, in Formulae 1B and 1C,

M is Pt, Pd, or Au, and

L 2 is a monodentate ligand represented by Formula 2-1 or 2-2, wherein L 2 is none of —F, —Cl, —Br, and —I:

wherein, in Formulae 1B, 1C, 2-1, and 2-2,

X 1 to X 3 are C, and X 4 is N or C,

T 15 is a chemical bond, *—O—*′, *—S—*′, *—B(R′)—*′, *—N(R′)—*′, *—P(R′)—*′, *—C(R′)(R″)—*′, *—Si(R′)(R″)—*′, *—Ge(R′)(R″)—*, *—C(═O)—*′, *—C(═S)—*′, *—O—C(═O)—*, *—S—C(═O)—*, *—O—C(═S)—*′, *—S—C(═S)—*′, *—C(R′)═C(R″)—*′, *—C═C—*′, *—C═C—C(═O)—*′, or *—C═C—C(═S)—*′,

when T 14 or T 15 is a chemical bond, X 4 or R 5 and M are directly linked to each other,

a bond between X 4 , T 14 , R 5 , or T 15 and M are each a coordinate bond or covalent bond,

T 1 is a single bond,

T 2 is a single bond,

ring CY 4 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

X 12 is N(R 12 ), X 13 is C(R 13 ), X 14 is C(R 14 ), X 15 is N or C(R 15 ), X 16 is N or C(R 16 ),

X 21 is C(R 21 ), X 22 is C(R 22 ), X 23 is C(R 23 ),

X 32 is N(R 32 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), at least one of X 33 to X 36 is N,

a4 is an integer from 0 to 20,

* and *′ each indicate a binding site to a neighboring atom,

—O(Q 31 ), —S(Q 31 ), —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ); or

any combination thereof, and

13 . The organometallic compound of claim 12 , wherein,

14 . The organometallic compound of claim 12 , wherein,

L 2 in Formulae 1B and 1C is a ligand represented by one of Formulae A4-1 (1) to A4-1 (4):

wherein, in Formulae A4-1 (1) to A4-1 (4),

X 4 is the same as described in claim 12 ,

X 40a is a single bond, O, S, S(═O) 2 , C(R 40a )(R 40b ), Si(R 40a )(R 40b ), N(R 40a ), or B(R 40a ),

X 40c is O, S, C(R 40c )(R 40d ), Si(R 40c )(R 40d ), or N(R 40c ),

X 40e is O, S, C(R 40e )(R 40f ), Si(R 40e )(R 40f ), or N(R 40e ),

X 40g is N, B, or P,

X 41 is N or C(R 41 ), X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), X 4 is N or C(R 4 ) , X 45 is N or C(R 45 ), X 46 is N or C(R 46 ), X 47 is N or C(R 47 ), X 48 is N or C(R 48 ), and X 49 is N or C(R 49 ),

R 40a to R 40f and R 41 to R 49 are each independently the same as defined in connection with R 4 , and

* indicates a binding site to M in Formulae 1B or 1C.

15 . The organometallic compound of claim 12 , wherein,

the organometallic compound is selected from Compounds BD11 to BD20, BD31 to BD40, BD51 to BD60, BD71 to BD80, BD85, BD90, BD95, BD100 and BD101 to BD105:

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 17, 2024

From: KO, SOOBYUNG; JEON, MINA; KIM, SUNGBUM; SHIN, SUJIN; AHN, EUNSOO; LEE, EUNYOUNG; LEE, JAESUNG; LEE, JIHYUNG; LEE, HYUNJUNG; HAN, JUNGHOON

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 066147/0779 →

Priority Claims (1)

KR 10-2019-0071060 · Jun 14, 2019 · national

Continuity (2)

Continuation 16889067 · Jun 1, 2020

Related Publication 20240244952A1 · Jul 18, 2024

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