IP Library › Granted Patent US 12,534,665
Granted Patent B2
US 12,534,665 · App. 16/666,327 · Granted Jan 27, 2026

Organometallic compound, organic light-emitting device including the same, and apparatus including the light-emitting device

Inventors: Soobyung Ko (Yongin-si, KR); Eunsoo Ahn (Yongin-si, KR); Hyunjung Lee (Yongin-si, KR); Mina Jeon (Yongin-si, KR); Sungbum Kim (Yongin-si, KR); Sujin Shin (Yongin-si, KR); Eunyoung Lee (Yongin-si, KR); Jaesung Lee (Yongin-si, KR); Jihyung Lee (Yongin-si, KR); Junghoon Han (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
C09K11/06C07F15/0033H10K85/342H10K85/40H10K85/6572C09K2211/1059C09K2211/185H10K50/11H10K50/121H10K2101/10H10K2101/90
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Quick Facts
Patent No.
US 12,534,665
App. No.
16/666,327
Granted
Jan 27, 2026
Kind
B2
Abstract

Provided are an organometallic compound, an organic light-emitting device including the same, and an apparatus including the organic light-emitting device. The organic light-emitting device includes: a first electrode; a second electrode; and an organic layer including an emission layer between the first electrode and the second electrode, wherein the organic layer includes the organometallic compound.

Claims (94)

1 . An organometallic compound, wherein:

the organometallic compound is selected from Group I:

2 . An organic light-emitting device comprising:

a first electrode;

a second electrode; and

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

wherein the organic layer comprises the organometallic compound of claim 1 .

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

the emission layer comprises the organometallic compound.

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

the emission layer further comprises a second compound and a third compound,

the organometallic compound, the second compound, and the third compound are different from each other,

the second compound and the third compound form an exciplex, and

the organometallic compound and at least one selected from the second compound and the third compound do not form an exciplex.

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

the second compound is represented by Formula 2; and

the third compound is represented by Formula 3:

wherein, in Formulae 2 and 3,

X 21 is selected from C(R 21 ) and N; X 22 is selected from C(R 22 ) and N; X 23 is selected from C(R 23 ) and N; X 24 is selected from C(R 24 ) and N; X 25 is selected from C(R 25 ) and N; X 26 is selected from C(R 26 ) and N; and at least one selected from X 21 to X 26 is N,

R 21 to R 26 are each independently selected from a group represented by *-(L 21 ) a21 -(R 27 ) b27 , hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 alkyl aryl 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 alkyl heteroaryl 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ) and —P(═S)(Q 1 )(Q 2 ), wherein at least one selected from R 21 to R 26 is a group represented by *-(L 21 ) a21 -(R 27 ) b27 ;

L 21 is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group, and

a21 is an integer from 0 to 6,

R 27 is selected from 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 alkyl aryl 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 alkyl heteroaryl 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 );

b27 is an integer from 1 to 10,

X 31 is selected from a single bond, O, S, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ), and Si(R 33 )(R 34 ); X 32 is selected from a single bond, O, S, B(R 35 ), N(R 35 ), C(R 35 )(R 36 ), and Si(R 35 )(R 36 ); and X 31 and X 32 are not each a single bond simultaneously,

ring A 31 to ring A 36 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,

R 31 to R 36 are each independently selected from a group represented by *-(L 31 ) a31 -(R 37 ) b37 , hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 alkyl aryl 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 alkyl heteroaryl 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ), wherein at least one selected from R 31 to R 36 is a group represented by *-(L 31 ) a31 -(R 37 ) b37 ;

b31 and b32 are each independently an integer from 1 to 10;

L 31 is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,

a31 is an integer from 0 to 6,

R 37 is selected from 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 alkyl aryl 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 alkyl heteroaryl 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 );

b37 is an integer from 1 to 10,

Q 1 to Q 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, a C 6 -C 60 aryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group, and a C 1 -C 60 heteroaryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group; and

* indicates a binding site to a neighbouring atom.

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

X 21 is N, X 22 is C(R 22 ); X 23 is C(R 23 ), X 24 is C(R 24 ); X 25 is C(R 25 ), and X 26 is C(R 26 );

X 21 is N, X 22 is C(R 22 ), X 23 is N, X 24 is C(R 24 ), X 25 is C(R 25 ), and X 26 is C(R 26 );

X 21 is N, X 22 is C(R 22 ), X 23 is C(R 23 ), X 24 is N, X 25 is C(R 25 ), and X 26 is C(R 26 ); or

X 21 is N, X 22 is C(R 22 ), X 23 is N, X 24 is C(R 24 ), X 25 is N, and X 26 is C(R 26 ).

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

R 27 is selected from —C(Q 1 )(Q 2 )(Q 3 ) and —Si(Q 1 )(Q 2 )(Q 3 ); and

a group represented by Formula 7-1 and a group represented by Formula 7-2:

wherein, in Formulae 7-1 and 7-2,

Y 71 is selected from 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 alkyl aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 31 )(Q 32 )(Q 33 ), and —Si(Q 31 )(Q 32 )(Q 33 ) ;

ring A 71 is selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,

X 71 is selected from C(R 71 ) and N;

R 71 and R 72 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 alkyl aryl 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 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), —N(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), and —P(═S)(Q 31 )(Q 32 ) ;

two groups selected from a plurality of R 71 and a plurality R 72 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group;

b72 is an integer from 1 to 10;

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 6 -C 60 aryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, and a C 1 -C 60 heteroaryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group; and

* indicates a binding site to a neighbouring atom.

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

ring A 31 and ring A 32 are each independently selected from a cyclohexane group, a cyclohexene group, a cyclohexadiene group, a benzene group, a naphthalene 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 siline group, an oxasiline group, a thiasiline group, an azasiline group, a dihydrodisiline group, a dioxine group, an oxathiine group, an oxazine group, a dithiine group, a thiazine group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a benzofluorene group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofuran group, a benzothienodibenzothiophene group, a dibenzosiline group, a dibenzooxasiline group, a dibenzothiasiline group, a dibenzoazasiline group, a dibenzodisiline group, a dibenzodioxine group, a dibenzooxathiine group, a dibenzooxazine group, a dibenzodithiine group, and a dibenzothiazine group.

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

R 37 is selected from a group represented by Formula 8-1 and a group represented by Formula 8-2:

wherein, in Formulae 8-1 and 8-2,

X 81 is selected from N, C(R 83 ), and Si(R 83 );

X 82 is selected from a single bond, O, S, B(R 84 ), N(R 84 ), C(R 84 )(R 85 ), and Si(R 84 )(R 85 );

X 83 is selected from a single bond, O, S, B(R 86 ), N(R 86 ), C(R 86 )(R 87 ), and Si(R 86 )(R 87 );

X 82 and X 83 in Formula 8-2 are not each a single bond simultaneously,

ring A 81 and ring A 82 may each independently be selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,

R 81 to R 87 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphtho silolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, an indolocarbazolyl group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), —N(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), and —P(═S)(Q 31 )(Q 32 ) ;

b81 and b82 are each independently an integer from 1 to 10; and

* indicates a binding site to a neighboring atom,

wherein Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, a C 6 -C 60 aryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group, and a C 1 -C 60 heteroaryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group.

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

the second compound is represented by one selected from Formulae 2-1 and 2-2:

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

X 21 is selected from C(R 21 ) and N; X 23 is selected from C(R 23 ) and N; X 24 is selected from C(R 24 ) and N; X 25 is selected from C(R 25 ) and N; and X 26 is selected from C(R 26 ) and N;

at least one selected from X 21 and X 23 to X 26 in Formula 2-1 is N,

at least one selected from X 21 and X 23 to X 25 in Formula 2-2 is N,

R 21 and R 23 to R 26 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 alkyl aryl 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 alkyl heteroaryl 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 );

L 21a and L 21b are each independently selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group, and a substituted or unsubstituted C 1 -C 60 heterocyclic group, a21a and a21b are each independently an integer from 0 to 6,

R 27a and R 27b may each independently be selected from —C(Q 1 )(Q 2 )(Q 3 ) and —Si(Q 1 )(Q 2 )(Q 3 ); and

a group represented by Formula 7-1 and a group represented by Formula 7-2;

wherein, in Formulae 7-1 and 7-2,

Y 71 is selected from 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 alkyl aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 31 )(Q 32 )(Q 33 ), and —Si(Q 31 )(Q 32 )(Q 33 ) ;

ring A 71 is selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,

X 71 is selected from C(R 71 ) and N;

R 71 and R 72 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 alkyl aryl 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 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), —N(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), and —P(═S)(Q 31 )(Q 32 ) ;

two groups selected from a plurality of R 71 and a plurality of R 72 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group;

b72 is an integer from 1 to 10;

b27a and b27b are each independently an integer from 1 to 10,

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 6 -C 60 aryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, and a C 1 -C 60 heteroaryl group which is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group; and

* indicates a binding site to a neighbouring atom.

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

the second compound is selected from Group II, and

the third compound is selected from Group III:

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

in a time-resolved electroluminescence (TREL) spectrum of the organic light-emitting device, the decay time of delayed fluorescence is 50 ns or more.

13 . An apparatus comprising:

a thin-film transistor comprising a source electrode, a drain electrode, and an active layer; and

the organic light-emitting device of claim 2 ,

wherein the first electrode of the organic light-emitting device is electrically coupled to one selected from the source electrode and the drain electrode of the thin-film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2019
From: KO, SOOBYUNG; AHN, EUNSOO; LEE, HYUNJUNG; JEON, MINA; KIM, SUNGBUM; SHIN, SUJIN; LEE, EUNYOUNG; LEE, JAESUNG; LEE, JIHYUNG; HAN, JUNGHOON
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 050848/0116 →
Priority Claims (1)
KR 10-2019-0043780 · Apr 15, 2019 · national
Continuity (1)
Related Publication 20200328359A1 · Oct 15, 2020
References Cited (145)
US 6310360B1 · Forrest et al. · 2001 [cited by applicant]
US 6515298B2 · Forrest et al. · 2003 [cited by applicant]
US 7279704B2 · Walters · 2007 [cited by examiner]
US 7381479B2 · Lamansky et al. · 2008 [cited by applicant]
US 7393599B2 · Thompson et al. · 2008 [cited by applicant]
US 7585573B2 · Lee et al. · 2009 [cited by applicant]
US 7776458B2 · Ragini et al. · 2010 [cited by applicant]
US 7990046B2 · Iwakuma et al. · 2011 [cited by applicant]
US 8106199B2 · Jabbour et al. · 2012 [cited by applicant]
US 8389725B2 · Li et al. · 2013 [cited by applicant]
US 8669364B2 · Li et al. · 2014 [cited by applicant]
US 8680760B2 · Cheng et al. · 2014 [cited by applicant]
US 8816080B2 · Li et al. · 2014 [cited by applicant]
US 8846940B2 · Li et al. · 2014 [cited by applicant]
US 8946417B2 · Jian et al. · 2015 [cited by applicant]
US 9051344B2 · Lin et al. · 2015 [cited by applicant]
US 9076974B2 · Li et al. · 2015 [cited by applicant]
US 9082986B2 · Kato et al. · 2015 [cited by applicant]
US 9203039B2 · Li et al. · 2015 [cited by applicant]
US 9221857B2 · Li et al. · 2015 [cited by applicant]
US 9224963B2 · Li et al. · 2015 [cited by applicant]
US 9238668B2 · Li et al. · 2016 [cited by applicant]
US 9312502B2 · Li et al. · 2016 [cited by applicant]
US 9324957B2 · Li et al. · 2016 [cited by applicant]
US 9382273B2 · Li et al. · 2016 [cited by applicant]
US 9425415B2 · Li et al. · 2016 [cited by applicant]
US 9458182B2 · Langer et al. · 2016 [cited by applicant]
US 9548467B2 · Archer · 2017 [cited by applicant]
US 9786858B2 · Adamovich et al. · 2017 [cited by applicant]
US 9991454B2 · Kim et al. · 2018 [cited by applicant]
US 10177329B2 · Kim et al. · 2019 [cited by applicant]
US 10411211B2 · Tsukamoto et al. · 2019 [cited by applicant]
US 10483328B2 · Lee et al. · 2019 [cited by applicant]
US 10559758B2 · Park et al. · 2020 [cited by applicant]
US 20010008271A1 · Ikeda et al. · 2001 [cited by applicant]
US 20050287394A1 · Yang et al. · 2005 [cited by applicant]
US 20050287396A1 · Nakamura · 2005 [cited by examiner]
US 20060103298A1 · Lee · 2006 [cited by examiner]
US 20080018221A1 · Egen et al. · 2008 [cited by applicant]
US 20100127616A1 · Kai · 2010 [cited by examiner]
US 20100219397A1 · Watanabe · 2010 [cited by examiner]
US 20100270916A1 · Xia · 2010 [cited by examiner]
US 20110301351A1 · Li et al. · 2011 [cited by applicant]
US 20120228583A1 · Wu · 2012 [cited by examiner]
US 20130105777A1 · Adamovich et al. · 2013 [cited by applicant]
US 20130200357A1 · Ludemann et al. · 2013 [cited by applicant]
US 20140309428A1 · Egen et al. · 2014 [cited by applicant]
US 20150041770A1 · Lee · 2015 [cited by applicant]
US 20150105556A1 · Li et al. · 2015 [cited by applicant]
US 20150137051A1 · Jung et al. · 2015 [cited by applicant]
US 20150137095A1 · Xia · 2015 [cited by examiner]
US 20150318487A1 · Ito et al. · 2015 [cited by applicant]
US 20160028025A1 · Ogiwara et al. · 2016 [cited by applicant]
US 20160240799A1 · Tsai et al. · 2016 [cited by applicant]
US 20160372687A1 · Murer et al. · 2016 [cited by applicant]
US 20170018600A1 · Ito et al. · 2017 [cited by applicant]
US 20170062730A1 · Ahn et al. · 2017 [cited by applicant]
US 20170077420A1 · Li et al. · 2017 [cited by applicant]
US 20170125699A1 · Ahn et al. · 2017 [cited by applicant]
US 20170149008A9 · Forrest et al. · 2017 [cited by applicant]
US 20170207398A1 · Yang et al. · 2017 [cited by applicant]
US 20170309841A1 · Kim et al. · 2017 [cited by applicant]
US 20180051003A1 · Koo et al. · 2018 [cited by applicant]
US 20180261791A1 · Yoo et al. · 2018 [cited by applicant]
US 20190109287A1 · Wu et al. · 2019 [cited by applicant]
US 20200258009A1 · Colon · 2020 [cited by applicant]
US 20200328359A1 · Ko et al. · 2020 [cited by applicant]
US 20210098714A1 · Choi et al. · 2021 [cited by applicant]
US 20210098716A1 · Lee et al. · 2021 [cited by applicant]
US 20210098721A1 · Jung et al. · 2021 [cited by applicant]
US 20210384450A1 · Shin et al. · 2021 [cited by applicant]
US 20220013737A1 · Kang et al. · 2022 [cited by applicant]
US 20220024958A1 · Ko et al. · 2022 [cited by applicant]
US 20220052276A1 · Lee et al. · 2022 [cited by applicant]
US 20220069235A1 · Kim et al. · 2022 [cited by applicant]
US 20230279029A1 · Fleetham et al. · 2023 [cited by applicant]
CN 1402885A · 2003 [cited by applicant]
CN 101253185A · 2008 [cited by applicant]
CN 103563118A · 2014 [cited by applicant]
CN 104370974A · 2015 [cited by applicant]
CN 104411702A · 2015 [cited by applicant]
CN 106232770A · 2016 [cited by applicant]
CN 106795166A · 2017 [cited by applicant]
CN 107431084A · 2017 [cited by applicant]
CN 112913040A · 2021 [cited by applicant]
JP 2004234952A · 2004 [cited by applicant]
JP 200745742A · 2007 [cited by applicant]
JP 2011140475A · 2011 [cited by applicant]
JP 015185728A · 2015 [cited by applicant]
JP 2017120867A · 2017 [cited by applicant]
JP 6232052B2 · 2017 [cited by applicant]
KR 100730115B1 · 2007 [cited by applicant]
KR 1020070106082A · 2007 [cited by applicant]
KR 1020080037006A · 2008 [cited by applicant]
KR 1020100118700A · 2010 [cited by applicant]
KR 1020120021215A · 2012 [cited by applicant]
KR 1020130048170A · 2013 [cited by applicant]
KR 1020130115027A · 2013 [cited by applicant]
KR 1020130118084A · 2013 [cited by applicant]
KR 1020140041732A · 2014 [cited by applicant]
KR 1020140134947A · 2014 [cited by applicant]
KR 101502316B1 · 2015 [cited by applicant]
KR 101505152B1 · 2015 [cited by applicant]
KR 1020150114791A · 2015 [cited by applicant]
KR 1020160045604 · 2016 [cited by applicant]
KR 1020160060569A · 2016 [cited by applicant]
KR 1020160073482A · 2016 [cited by applicant]
KR 1020160110764A · 2016 [cited by applicant]
KR 1020170008358A · 2017 [cited by applicant]
KR 1020170008673A · 2017 [cited by applicant]
KR 1020170103358A · 2017 [cited by applicant]
KR 1020180104258A · 2018 [cited by applicant]
KR 1020180115800A · 2018 [cited by applicant]
WO 0108230A1 · 2001 [cited by applicant]
WO WO2008096609A1 · 2008 [cited by applicant]
WO WO2010126234A1 · 2010 [cited by applicant]
WO WO2012121936A2 · 2012 [cited by applicant]
WO 2014003440A1 · 2014 [cited by applicant]
WO WO2015000955A1 · 2015 [cited by applicant]
WO 2016080749A1 · 2016 [cited by applicant]
WO WO2016080791A1 · 2016 [cited by applicant]
WO WO2017082169A1 · 2017 [cited by applicant]
WO 2020096167A1 · 2020 [cited by applicant]
Huiqing Pang et al. “A full-color, low-power, wearable display for mobile applications”, SPIE, Mar. 29, 2012 (Year: 2012). [cited by examiner]
Miguel A. Esteruelas et al. “Preparation of Phosphorescent Iridium(III) Complexes with a Dianionic C,C,C,C-Tetradentate Ligand”, Inorg. Chem. 2018, vol. 57, p. 3720-3730, Mar. 14, 2018 (Year: 2018). [cited by examiner]
Huei-Ru Tsai et al. “Metal-Ligand Bonding Strength of Fluoro-Substituted Cyclometalated Iridium(III) Complexes from Raman and Infrared Spectra”, J. Phys. Chem. 2011, vol. 115, p. 17163-17174 (Year: 2011). [cited by examiner]
Esteruelas, Miguel A., et al., “Preparation of Phosphorescent Iridium(III) Complexes with a Dianionic C,C,C,C-Tetradentate Ligand,” Inorg. Chem. 2018, 57, 7, pp. 3720-3730. [cited by applicant]
English Translation of International Preliminary Report issued in PCT/KR2019/009197, Search Authority search carriec JUI on Feb. 22, 2021, 3 pages. [cited by applicant]
Intemational Search Report issued in PCT/KR2019/009197 (English Version), mailed Oct. 21, 2019, 2 pages. [cited by applicant]
US Notice of Allowance dated Sep. 21, 2022, issued in U.S. Appl. No. 16/529,327 (7 pages). [cited by applicant]
Chemical Abstracts Service (CAS) Reg. No. 2422045-58-5, Jun. 10, 2020, 1 page. [cited by applicant]
EPO Extended European Search Report dated Jul. 21, 2021 issued in European Patent Application No. 21159425.4, 18 pages. [cited by applicant]
EPO Extended European Search Report dated Jun. 11, 2021 issued in European Patent Application No. 21159426.2, 8 pages. [cited by applicant]
Office Action for U.S. Appl. No. 16/529,327 dated Mar. 23, 2022, 12 pages. [cited by applicant]
Restriction Requirement for U.S. Appl. No. 16/529,327 dated Dec. 24, 2021, 5 pages. [cited by applicant]
Final Office Action for U.S. Appl. No. 16/529,327 dated Jul. 13, 2022, 12 pages. [cited by applicant]
US Notice of Allowance dated Feb. 2, 2023, issued in U.S. Appl. No. 16/529,327 (7 pages). [cited by applicant]
US Notice of Allowance dated Oct. 12, 2023, issued in U.S. Appl. No. 16/529,327 (8 pages). [cited by applicant]
Chinese Office Action dated Jan. 27, 2024, issued in Chinese Patent Application No. 201980068141.8, 11 pages. [cited by applicant]
“Analog Electronic Technology”, with English Abstract, dated Jul. 31, 2010, 22 pages. [cited by applicant]
Chinese Office Action for Chinese Patent Application No. 202010073332.8, dated Mar. 18, 2024, 29 pages. [cited by applicant]
US Office Action dated May 16, 2024, issued in U.S. Appl. No. 16/529,327 (13 pages). [cited by applicant]
US Final Office Action dated Sep. 26, 2024, issued in U.S. Appl. No. 16/529,327 (12 pages). [cited by applicant]
US Office Action dated Mar. 24, 2025, issued in U.S. Appl. No. 16/529,327 (14 pages). [cited by applicant]
US Office Action dated Jul. 16, 2025, issued in U.S. Appl. No. 16/529,327 (12 pages). [cited by applicant]