# US 12,120,947 B2 · Organometallic compound, composition including same, organic light-emitting device, and electronic apparatus

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- Number: US 12,120,947 B2
- Document ID: US12120947B2
- Status: Granted
- Kind: B2
- Application number: 17/199,655
- Filed: 2021-03-12
- Published: 2022-06-16
- Granted: 2024-10-15
- Earliest claimed: 2020-12-03
- Assignees: Samsung Electronics Co., Ltd.; Universitat De Barcelona
- Applicants: Samsung Electronics Co., Ltd.; Universitat De Barcelona
- Inventors: Yongsik Jung; Laura Rodriguez Raurell; Joao Carlos Lima; Hyeonho Choi; Seungyeon Kwak; Kyuyoung Hwang
- Web page: https://patentgrep.com/patent/US12120947B2

## CPC

- H10K 85/371: {Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver}
- C07F 1/00: Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F 1/12: Gold compounds
- C07F 9/5027: {Polyphosphines}
- C07F 9/5045: {Complexes or chelates of phosphines with metallic compounds or metals}
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1011: Condensed systems
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

An organometallic compound represented by Formula 1 wherein, M1 to M4 are each independently a first-row transition metal, a second-row transition metal, or a third-row transition metal; X1 and X2 are each independently C(R5)(R6), Si(R5)(R6), N(R5), O, S, Se, or Te; W1 to W4 are each independently N(R7)(R8), P(R7)(R8), S(R7), a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a; L1 to L6 are each independently a C1-C30 alkylene group unsubstituted or substituted with at least one R10a, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a3 to a6 are each independently an integer from 0 to 3, and R1 to R8 and R10a in Formula 1 are as described herein.

## Claims

### Claim 1

An organometallic compound represented by Formula 1:
wherein, in Formula 1,
M1 to M4 are each independently a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements,
X1 and X2 are each independently C(R5)(R6), Si(R5)(R6), N(R5), O, S, Se, or Te,
W1 to W4 are each independently N(R7)(R8), P(R7)(R8), S(R7), a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
L1 to L6 are each independently a C1-C30 alkylene group unsubstituted or substituted with at least one R10a, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
a3 to a6 are each independently an integer from 0 to 3,
R1 to R8 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkyl group unsubstituted or substituted with at least one R10a, a C3-C10 cycloalkenyl group unsubstituted or substituted with at least one R10a, a C1-C10 heterocycloalkenyl group unsubstituted or substituted with at least one R10a, a C6-C60 aryl group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C1-C10 heteroaryl group unsubstituted or substituted with at least one R10a, a C1-C10 heteroaryloxy group unsubstituted or substituted with at least one R10a, a C1-C60 heteroarylthio group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkylheteroaryl group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R10a, a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
R7 and R8 are optionally connected to each other to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
b1 and b3 are each independently an integer from 1 to 4,
b2 and b4 are each independently an integer from 1 to 3,
n1 is 0 or 1,
provided that when n1 is 0, a group represented by:
is not present, and
R10a is:
deuterium, —CD3, —CD2H, —CDH2, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with one or more of deuterium, —CD3, —CD2H, —CDH2, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —Ge(Q11)(Q12)(Q13), —N(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), or —P(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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C0 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —CD3, —CD2H, —CDH2, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C10 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —Ge(Q21)(Q22)(Q23), —N(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), or —P(Q28)(Q29); or
—Si(Q31)(Q32)(Q33), —Ge(Q31)(Q32)(Q33), —N(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39),
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C10 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 C1-C10 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

### Claim 2 (depends on 1)

The organometallic compound of claim 1, wherein M1 to M4 are each independently copper (Cu), silver (Ag), or gold (Au).

### Claim 3 (depends on 1)

The organometallic compound of claim 1, wherein W1 to W4 are each independently N(R7)(R8), P(R7)(R8), S(R7), or a group represented by one of Formulae 2-1 to 2-7:
wherein, in Formulae 2-1 to 2-7,
R10a is the same as described in claim 1,
c2 is 1 or 2,
c3 is 1, 2, or 3,
c4 is 1, 2, 3, or 4,
* indicates a binding site to M1, M2, M3, or M4, and
*′ indicates a binding site to L1 or L2.

### Claim 4 (depends on 1)

The organometallic compound of claim 1, wherein W1 to W4 are each independently N(R7)(R8), P(R7)(R8), S(R7), or a group represented by one of Formulae 2-11 to 2-18:
wherein, in Formulae 2-11 to 2-18,
R10a is the same as described in claim 1,
c2 is 1 or 2,
c3 is 1, 2, or 3,
c4 is 1, 2, 3, or 4,
* indicates a binding site to M1, M2, M3, or M4, and
*′ indicates a binding site to L1 or L2.

### Claim 5 (depends on 1)

The organometallic compound of claim 1, wherein Li and L2 are each independently a group represented by Formula 3-1 or 3-2:
wherein, in Formulae 3-1 and 3-2,
C1 and C2 each indicate a carbon atom,
a bond between C1 and C2 is a single bond or a double bond,
CY1 is a C5-C30 carbocyclic group, or a C1-C30 heterocyclic group,
Z11, Z12, and Z2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
Z11 and Z12 are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R10a is the same as described in claim 1,
n2 is an integer from 1 to 10,
k1 is an integer from 1 to 10,
Q1 to Q9 are the same as described in claim 1, and
* and *′ each indicate a binding site to a neighboring atom.

### Claim 6 (depends on 5)

The organometallic compound of claim 5, wherein in Formulae 3-1 and 3-2, Z11, Z12, and Z2 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C20 alkyl group, or a C1-C20 alkoxy group; or
a C1-C20 alkyl group, or a C1-C20 alkoxy group, each substituted with one or more of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, or an amino group.

### Claim 7 (depends on 5)

The organometallic compound of claim 5, wherein, in Formulae 3-1 and 3-2, Z11, Z12, and Z2 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-isopentyl group; or
a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-isopentyl group, each substituted with one or more of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, or an amino group.

### Claim 8 (depends on 1)

The organometallic compound of claim 1, wherein L1 and L2 are each independently a group represented by one of Formulae 3-11 to 3-22:
wherein, in Formulae 3-11 to 3-22,
X21 is C(Z22)(Z23), Si(Z22)(Z23), N(Z22), O, S, or Se,
Z11 to Z18, Z2, and Z21 to Z23 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 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 C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), P(═O)(Q8)(Q9), or —P(Q8)(Q9),
k3 is an integer from 1 to 3,
k4 is an integer from 1 to 4,
k6 is an integer from 1 to 6,
k8 is an integer from 1 to 8,
k10 is an integer from 1 to 10,
Q1 to Q9 are the same as described in claim 1, and
* and *′ each indicate a binding site to a neighboring atom.

### Claim 9 (depends on 1)

The organometallic compound of claim 1, wherein a3 to a6 are each 0.

### Claim 10 (depends on 1)

The organometallic compound of claim 1, wherein R1 to R8 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, or an amino group;
a C1-C60 alkyl group and a C1-C60 alkoxy group, each unsubstituted or substituted with one or more of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, or an amino group;
a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, or a pyridobenzothiazinyl group, each unsubstituted or substituted with one or more of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, or a pyridobenzothiazinyl group; or
—Si(Q1)(Q2)(Q3), —N(Q4)(Q5), or —B(Q6)(Q7),
wherein Q1 to Q7 are each independently hydrogen, deuterium, a C1-C10 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, or a triazinyl group.

### Claim 11 (depends on 1)

The organometallic compound of claim 1, wherein W1 to W4 are each independently P(R7)(R8), and
R7 and R8 are each independently a phenyl group unsubstituted or substituted with one or more of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C1-C20 alkyl group, or a C1-C20 alkoxy group.

### Claim 12 (depends on 1)

The organometallic compound of claim 1, wherein the organometallic compound is represented by Formula 1-1 or 1-2:
wherein, in Formula 1-1 or 1-2,
R71 to R74 are the same as described in connection with R7 in claim 1,
R81 to R84 are the same as described in connection with R8 in claim 1, and
W1 to W4, X1, X2, L1, L2, R1 to R4, and b1 to b4 are the same as described in claim 1.

### Claim 13 (depends on 1)

The organometallic compound of claim 1, wherein the organometallic compound is represented by one of Compounds 1 to 810:

### Claim 14 (depends on 1)

The organometallic compound of claim 1, wherein the organometallic compound absorbs ultraviolet light (UV) at 25° C. and emits phosphorescent light having a maximum luminescence wavelength of 470 nanometers to 500 nanometers.

### Claim 15 (depends on 1)

A composition comprising at least one organometallic compound of claim 1.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the composition is a diagnostic composition, a composition for measurement, or a security ink composition.