IP Library › Granted Patent US 12,751,199
Granted Patent B2
US 12,751,199 · App. 18/107,609 · Granted Sep 29, 2026

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

Inventors: Junghoon Han (Yongin-si, KR); Soobyung Ko (Yongin-si, KR); Sungbum Kim (Yongin-si, KR); Eunsoo Ahn (Yongin-si, KR); Jaesung Lee (Yongin-si, KR); Hyunjung Lee (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/346C07F15/0086H10K50/12C07B2200/05H10K2102/301
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Quick Facts
Patent No.
US 12,751,199
App. No.
18/107,609
Granted
Sep 29, 2026
Kind
B2
Abstract

Embodiments provide an organometallic compound, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device. The light-emitting device includes a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, and the organometallic compound, which is represented by Formula 1, as defined in the specification:

Claims (179)

1 . A light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

an interlayer between the first electrode and the second electrode and comprising an emission layer; and

an organometallic compound represented by Formula 1:

wherein in Formula 1,

M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), iridium (Ir), or osmium (Os),

X 1 to X 4 are each independently C or N,

a bond between X 1 and M is a coordinate bond,

one of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond,

the remainder of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M are each a covalent bond,

ring CY 1 to ring CY 7 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

L 1 to L 3 are each independently a single bond, *—C(R 8 )(R 9 )—*′, *—C(R 8 )═*′, *═C(R 8 )—*′, *—C(R 8 )═C(R 9 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 8 )—*′, *—N(R 8 )—*′, *—O—*′, *—P(R 8 )—*′, *—Si(R 8 )(R 9 )—*′, *—P(═O)(R 8 )—*′, *—S—*′, *—S(═O)—*′, *—S(═O) 2 —*′ or *—Ge(R 8 )(R 9 )—*′,

n1 to n3 are each independently an integer from 1 to 3,

T 1 is *—C(Z 11 )(Z 12 )—*′ or *—Si(Z 11 )(Z 12 )—*′,

T 2 is *—N(Z 13 )—*′, *—O—*′, *—S—*′, *—C(Z 13 )(Z 14 )—*′, or *—Si(Z 13 )(Z 14 )—*′,

b2 is 0, 1, or 2, wherein T 2 is not present when b2 is 0,

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

R 1 to R 9 and Z 11 to Z 14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(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 ), or —P(═S)(Q 1 )(Q 2 ),

a1 to a7 are each independently an integer from 0 to 20,

each of two or more of R 1 in the number of a1; two or more of R 2 in the number of a2; two or more of R 3 in the number of a3; two or more of R 4 in the number of a4; two or more of R 5 in the number of a5; two or more of R 6 in the number of a6; two or more of R 7 in the number of a7; R 8 and R 9 ; Z 11 and Z 12 ; and Z 13 and Z 14 , are optionally bonded to each other to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

two or more of R 1 to R 4 , R 8 , and R 9 are optionally bonded to each other to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a is:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro 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 unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —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)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), —P(═S)(Q 11 )(Q 12 ), or a combination thereof;

a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —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)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), —P(═S)(Q 21 )(Q 22 ), or a combination thereof; or

—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)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), or —P(═S)(Q 31 )(Q 32 ), 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; 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; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.

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

the interlayer 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 includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and

the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or a combination thereof.

3 . The light-emitting device of claim 1 , wherein the emission layer includes the organometallic compound represented by Formula 1.

4 . The light-emitting device of claim 1 , wherein the emission layer emits blue light having a maximum emission wavelength in a range of about 410 nm to about 500 nm.

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

the interlayer comprises:

a first compound which is the organometallic compound represented by Formula 1; and

a second compound including a group represented by Formula 2, a third compound represented by Formula 3, a fourth compound including a group represented by Formula 4, or a combination thereof,

the first compound, the second compound, and the third compound are different from one another,

the first compound, the second compound, and the fourth compound are different from one another, and

the third compound and the fourth compound are identical to or different from each other:

wherein in Formula 2,

ring CY 71 and ring CY 72 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,

X 71 is:

a single bond; or

a linking group including O, S, N, B, C, Si, or a combination thereof,

* indicates a binding site to a neighboring atom in the second compound,

wherein in Formula 3,

L 61 to L 63 are each independently a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

b61 to b63 are each independently an integer from 1 to 5,

X 64 is N or C(R 64 ),

X 65 is N or C(R 65 ),

X 66 is N or C(R 66 ),

at least one of X 64 to X 66 is N,

R 61 to R 66 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —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 10a and Q 1 to Q 3 are each as defined in Formula 1,

wherein in Formula 4,

ring A 91 and ring A 92 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,

X 91 is:

a single bond; or

a linking group including O, S, N, B, C, Si, or a combination thereof,

R 91 and R 92 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —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 ),

a91 and a92 are each independently an integer from 0 to 10,

c1 and c2 are each independently an integer from 0 to 10,

a sum of c1 and c2 is 1 or more,

R 10a and Q 1 to Q 3 are each as defined in Formula 1, and

* indicates a binding site to a neighboring atom in the fourth compound.

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

the emission layer includes a dopant and a host,

the dopant includes the first compound, and

the host includes the second compound, the third compound, the fourth compound, or a combination thereof.

7 . An electronic apparatus comprising:

the light-emitting device of claim 1 ; and

a thin-film transistor, wherein

the thin-film transistor includes a source electrode and a drain electrode, and

the first electrode of the light-emitting device is electrically connected to at least one of the source electrode and the drain electrode.

8 . The electronic apparatus of claim 7 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.

9 . An electronic equipment comprising the light-emitting device of claim 1 , wherein the electronic equipment is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertisement board, an indoor lighting, an outdoor lighting, a signaling light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual-reality display, an augmented-reality display, a vehicle, a video wall including multiple displays tiled together, a theater screen, a stadium screen, a phototherapy device, or a sign.

10 . An organometallic compound represented by Formula 1:

wherein in Formula 1,

M is platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), iridium (Ir), or osmium (Os),

X 1 to X 4 are each independently C or N,

a bond between X 1 and M is a coordinate bond,

one of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond,

the remainder of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M are each a covalent bond,

ring CY 1 to ring CY 7 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

L 1 to L 3 are each independently a single bond, *—C(R 8 )(R 9 )—*′, *—C(R 8 )═*′, *═C(R 8 )—*′, *—C(R 8 )═C(R 9 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 8 )—*′, *—N(R 8 )—*′, *—O—*′, *—P(R 8 )—*′, *—Si(R 8 )(R 9 )—*′, *—P(═O)(R 8 )—*′, *—S—*′, *—S(═O)—*′, *—S(═O) 2 —*′ or *—Ge(R 8 )(R 9 )—*′,

n1 to n3 are each independently an integer from 1 to 3,

T 1 is *—C(Z 11 )(Z 12 )—*′ or *—Si(Z 11 )(Z 12 )—*′,

T 2 is *—N(Z 13 )—*′, *—O—*′, *—S—*′, *—C(Z 13 )(Z 14 )—*′, or *—Si(Z 13 )(Z 14 )—*′,

b2 is 0, 1, or 2, wherein T 2 is not present when b2 is 0,

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

R 1 to R 9 and Z 11 to Z 14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(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 ), or —P(═S)(Q 1 )(Q 2 ),

a1 to a7 are each independently an integer from 0 to 20,

each of two or more of R 1 in the number of a1; two or more of R 2 in the number of a2; two or more of R 3 in the number of a3; two or more of R 4 in the number of a4; two or more of R 5 in the number of a5; two or more of R 6 in the number of a6; two or more of R 7 in the number of a7; R 8 and R 9 ; Z 11 and Z 12 ; and Z 13 and Z 14 , are optionally bonded to each other to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

two or more of R 1 to R 4 , R 8 , and R 9 are optionally bonded to each other to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a is:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro 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 unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —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)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), —P(═S)(Q 11 )(Q 12 ), or a combination thereof;

a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —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)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), —P(═S)(Q 21 )(Q 22 ), or a combination thereof; or

—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)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), or —P(═S)(Q 31 )(Q 32 ), 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; 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; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.

11 . The organometallic compound of claim 10 , wherein each of X 1 to X 3 is C.

12 . The organometallic compound of claim 10 , wherein ring CY 1 to ring CY 7 are each independently a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzooxazole group, a benzoisooxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, a pyrido[2,3-b]indole group, a pyrido[3,4-b]indole group, a pyrido[4,3-b]indole group, a pyrido[3,2-b]indole group, or a pyrrolo[2,3-b]pyridine group.

13 . The organometallic compound of claim 10 , wherein

ring CY 1 is a benzene group, a pyridine group, a pyridazine group, a pyrimidine group, a pyrazine group, a naphthalene group, a quinoline group, or an isoquinoline group,

ring CY 2 and ring CY 3 are each independently a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an azacarbazole group, a fluorene group, or a dibenzosilole group,

ring CY 4 is:

an X 4 -containing 5-membered ring; or

an X 4 -containing 6-membered ring; or

an X 4 -containing 5-membered ring in which at least one 6-membered ring is condensed,

the X 4 -containing 5-membered ring is a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and

the X 4 -containing 6-membered ring and the at least one 6-membered ring that is optionally condensed with the X 4 -containing 5-membered ring are each independently a benzene group, a pyridine group, or a pyrimidine group.

14 . The organometallic compound of claim 10 , wherein at least one of Condition 1 to Condition 4 is satisfied:

[Condition 1]

a moiety represented by

 in Formula 1 is a moiety represented by one of Formulae CY1-1 to CY1-25:

wherein in Formulae CY1-1 to CY1-25,

X 1 is as defined in Formula 1,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to (L 1 ) n1 in Formula 1, and

*″ indicates a binding site to ring CY 7 in Formula 1;

[Condition 2]

a moiety represented by

 in Formula 1 is a moiety represented by one of Formulae CY2-1 to CY2-11:

wherein in Formulae CY2-1 to CY2-11,

X 2 is as defined in Formula 1,

Y 2 comprises O, S, N, C, or Si,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to (L 1 ) n1 in Formula 1, and

*″ indicates a binding site to (L 2 ) n2 in Formula 1;

[Condition 3]

a moiety represented by

 in Formula 1 is a moiety represented by one of Formulae CY3-1 to CY3-23:

wherein in Formulae CY3-1 to CY3-23,

X 3 is as defined in Formula 1,

Y 3 comprises O, S, N, C, or Si,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to (L 3 ) n3 in Formula 1, and

*″ indicates a binding site to (L 2 ) n2 in Formula 1; and

[Condition 4]

a moiety represented by

 in Formula 1 is a moiety represented by one of Formulae CY4-1 to CY4-48:

wherein in Formulae CY4-1 to CY4-48,

X 4 is as defined in Formula 1,

Y 4 comprises O, S, N, C, or Si,

* indicates a binding site to M in Formula 1, and

*′ indicates a binding site to (L 3 ) n3 in Formula 1.

15 . The organometallic compound of claim 10 , wherein ring CY 5 to ring CY 7 are each independently a benzene group, a naphthalene group, a pyridine group, a pyridazine group, a pyrimidine group, a pyrazine group, a triazine group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an azacarbazole group, an azadibenzofuran group, or an azadibenzothiophene group.

16 . The organometallic compound of claim 10 , wherein

L 1 is a single bond; or

L 2 is *—C(R 8 )(R 9 )—*′, *—B(R 8 )—*′, *—N(R 8 )—*′, *—O—*′, *—P(R 8 )—*′, *—Si(R 8 )(R 9 )—*′, or *—S—*′, or

L 3 is a single bond, *—N(R 8 )—*′, or *—O—*′; or

a combination thereof.

17 . The organometallic compound of claim 10 , wherein the organometallic compound satisfies Condition L-1 or Condition L-2:

[Condition L-1]

L 3 is a single bond, and ring CY 3 is a benzene group, a carbazole group, or an azacarbazole group;

[Condition L-2]

L 3 is *—O*′, and ring CY 3 is a benzene group, a pyridine group, or a pyrimidine group.

18 . The organometallic compound of claim 10 , wherein a moiety represented by

in Formula 1 is a moiety represented by one of Formulae B1-1 to B1-12:

wherein in Formulae B1-1 to B1-12,

T 1 , T 2 , ring CY 5 , and ring CY 6 are each as defined in Formula 1,

Y 71 is N or C(R 7a ),

Y 73 is N or C(R 7c ),

Y 74 is N or C(R 7d ),

Y 75 is N or C(R 7e ),

R 7a and R 7c to R 7e are each independently as defined in connection with R 7 in Formula 1, and

* indicates a binding site to a nitrogen atom in Formula 1.

19 . The organometallic compound of claim 10 , wherein Z 11 to Z 14 are each independently:

hydrogen, deuterium, —F, or a cyano group;

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, or a C 1 -C 20 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or a combination thereof; or

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrim idinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrim idinyl group, or a combination thereof.

20 . The organometallic compound of claim 10 , wherein the organometallic compound is selected from Compounds 1 to 100:

wherein in Compounds 1 to 100,

D 5 indicates substitution with five deuterium atoms, and

Ph indicates a phenyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2023
From: HAN, JUNGHOON; KO, SOOBYUNG; KIM, SUNGBUM; AHN, EUNSOO; LEE, JAESUNG; LEE, HYUNJUNG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 062689/0420 →
Priority Claims (1)
KR 10-2022-0034176 · Mar 18, 2022 · national
Continuity (1)
Related Publication 20230301170A1 · Sep 21, 2023
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