# US 12,595,277 B2 · Light-emitting material with a polycyclic ligand

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- Number: US 12,595,277 B2
- Document ID: US12595277B2
- Status: Granted
- Kind: B2
- Application number: 17/720,515
- Filed: 2022-04-14
- Published: 2022-11-17
- Granted: 2026-04-07
- Earliest claimed: 2021-04-16
- Assignees: Beijing Summer Sprout Technology Co., Ltd.
- Applicants: Beijing Summer Sprout Technology Co., Ltd.
- Inventors: Zhihong Dai; Cuifang Zhang; Qi Zhang; Nannan Lu; Chi Yuen Raymond Kwong; Chuanjun Xia
- Web page: https://patentgrep.com/patent/US12595277B2

## CPC

- C07F 15/0033: {Iridium compounds}
- H10K 85/342: {comprising iridium}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Provided is a luminescent material having a polycyclic ligand. The luminescent material is a new metal complex having a polycyclic ligand and may be used as luminescent materials in electroluminescent devices. These new metal complexes achieve red light emission, have a very narrow full width at half maximum, and can achieve high saturation luminescence. In addition, these new metal complexes, when used as luminescent materials in electroluminescent devices, can achieve red light emission, have a very narrow full width at half maximum, achieve high saturation luminescence, reduce or maintain a low voltage, greatly improve device efficiency and lifetime, and provide better device performance. Further provided are an electroluminescent device and a compound composition.

## Claims

### Claim 1

A metal complex, having a general formula of M(La)m(Lb)n(Lc)q; wherein the metal M is selected from metals having a relative atomic mass greater than 40, La, Lb and Lc are a first ligand, a second ligand and a third ligand coordinated to the metal M, respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to an oxidation state of the metal M; when m is equal to 2 or 3, a plurality of La can be identical or different; when n is equal to 2, two Lb can be identical or different; and when q is equal to 2, two Lc can be identical or different; and La has a structure represented by Formula 1:
wherein,
Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;
W is, at each occurrence identically or differently, selected from B, N or P;
ring A, and ring C are, at each occurrence identically or differently, selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
ring D is selected from a benzene ring, a naphthalene ring, an aza-naphthalene ring, a pyridine ring or a pyrimidine ring;
ring B is selected from a heterocyclic ring having 2 to 30 carbon atoms or a heteroaromatic ring having 2 to 30 carbon atoms;
Ra, Rb, Rc, and Rd represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
Ra, Rb, Rc, and Rd are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Ra, Rb, Rc, and Rd can be optionally joined to form a ring;
La, Lb, and Lc can be optionally joined to form a multi-dentate ligand;
Lb and Lc are, at each occurrence identically or differently, selected from the group consisting of the following structures:
wherein,
Ri, Rii, and Riii represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
Xa is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NRN1, and CRC1RC2;
Xb and Xc are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NRN2;
Ri, Rii, Riii, RN1, RN2, RC1, and RC2 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Ri, Rii, Riii, RN1, RN2, RC1, and RC2 can be optionally joined to form a ring.

### Claim 2 (depends on 1)

The metal complex of claim 1, wherein in the La, ring A, and ring C are, at each occurrence identically or differently, selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; and ring B is selected form a heteroaromatic ring having 2 to 18 carbon atoms.

### Claim 3 (depends on 1)

The metal complex of claim 1, wherein the La is selected from a structure represented by any one of Formula 2 to Formula 18:
wherein,
Z1 and Z2 are each independently selected from C or N, and Z1 and Z2 are different;
W is, at each occurrence identically or differently, selected from B, N or P;
A1 to As are, at each occurrence identically or differently, selected from N or CRa;
B1 to B4 are, at each occurrence identically or differently, selected from N or CRb;
C1 to C4 are, at each occurrence identically or differently, selected from N or CRc;
in Formula 2 to Formula 9, and Formula 13 to Formula 18, D1 is selected from CRd, D2 is selected from N or CRa; in Formula 10 to Formula 12, D1 to D4 are, at each occurrence identically or differently, selected from N or CRd;
X1 is, at each occurrence identically or differently, selected from O, S, Se, NRc, CRcRc, SiRcRc or PRc;
Z3 is, at each occurrence identically or differently, selected from O, S, Se, NRz, CRzRz, SiRzRz or PRz;
Ra, Rb, Rc, Ra, and Rz are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Ra, Rb, Rc, Rd, and Rz can be optionally joined to form a ring.

### Claim 4 (depends on 3)

The metal complex of claim 3, wherein in Formula 1 to Formula 18, Z1 is N, and Z2 is C.

### Claim 5 (depends on 3)

The metal complex of claim 3, wherein in Formula 1 to Formula 18, W is N.

### Claim 6 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 9, Formula 13 to Formula 18, Z1 is N, and D2 is N; in Formula 10 to Formula 12, Z1 is N, and at least one of D1 and D2 is N; or in Formula 2 to Formula 17, Z2 is N, and at least one of C1 and C2 is N.

### Claim 7 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 18, A1 to As are each independently selected from CRa, and B1 to B4 are each independently selected from CRb; in Formula 2 to Formula 17, C1 to C4 are each independently selected from CRc; in Formula 2 to Formula 18, D1 to D4 are each independently selected from CRa; and the Ra, Rb, Rc, and Rd are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Ra, Rb, Rc, and Rd can be optionally joined to form a ring.

### Claim 8 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 18, at least one of A1 to An is, at each occurrence identically or differently, selected from CRa, and the An corresponds to one having the largest serial number of A1 to As in any one of Formula 2 to Formula 18; and the at least one Ra is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, a cyano group, a hydroxyl group, a sulfanyl group, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, and combinations thereof;
adjacent substituents Ra can be optionally joined to form a ring.

### Claim 9 (depends on 8)

The metal complex of claim 8, wherein in Formula 2 to Formula 14 and Formula 18, at least one of A1 to A3 is, at each occurrence identically or differently, selected from CRa.

### Claim 10 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 17, C2 is selected from CRc, and the Rc is selected from the group consisting of: deuterium, halogen, a cyano group, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, and combinations thereof.

### Claim 11 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 18, at least one of B1 to Bn is selected from CRb, and the Bn corresponds to one having the largest serial number of B1 to B4 in any one of Formula 2 to Formula 18; and/or in Formula 2 to Formula 18, at least one of D1 to Dn is selected from CRa, and the Dn corresponds to one having the largest serial number of D1 to D4 in any one of Formula 2 to Formula 18; and the Rb and Ra are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.

### Claim 12 (depends on 11)

The metal complex of claim 11, wherein in Formula 2 to Formula 12, Formula 16 and Formula 18, B2 and/or B3 are selected from CRb; in Formula 13 to Formula 15 and Formula 17, B1 and/or B2 are selected from CRb; and in Formula 2 to Formula 18, D1 and/or D2 are selected from CRd.

### Claim 13 (depends on 3)

The metal complex of claim 3, wherein La is selected from a structure represented by Formula 2, Formula 3, Formula 7, Formula 8, Formula 9 or Formula 12.

### Claim 14 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 18, Z1 is C, and Z2 is N.

### Claim 15 (depends on 3)

The metal complex of claim 3, wherein in Formula 2 to Formula 18, A1 to As are each independently selected from CRa, and B1 to B4 are each independently selected from CRb; in Formula 2 to Formula 17, C1 to C4 are each independently selected from CRc; in Formula 2 to Formula 18, D1 to D4 are each independently selected from CRd; and the Ra, Rb, Rc, and Rd are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, and combinations thereof.

### Claim 16 (depends on 1)

The metal complex of claim 1, wherein La is, at each occurrence identically or differently, selected from the group consisting of the following structures:
wherein TMS represents trimethylsilyl, and Ph represents phenyl;
wherein, optionally, hydrogen in the structures La1 to La956, La985 to La1009, La1020 to La1074, La1097 to La1100, La1105 to La1342 can be partially or completely substituted with deuterium.

### Claim 17 (depends on 1)

The metal complex of claim 1, having a general formula of M(La)m(Lb)n(Lc)q;
wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu La, Lb and Lc are a first ligand, a second ligand and a third ligand coordinated to the metal M, respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to an oxidation state of the metal M; when m is equal to 2 or 3, a plurality of La can be identical or different; when n is equal to 2, two Lb can be identical or different; and when q is equal to 2, two Lc can be identical or different;
La, Lb, and Lc can be optionally joined to form a multi-dentate ligand;
Lb and Lc are, at each occurrence identically or differently, selected from the group consisting of the following structures:
wherein,
Ri, Rii represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
Xb and Xc are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NRN2;
Ri, Rii, Riii, RN2 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Ri, Rii, Riii, RN2 can be optionally joined to form a ring.

### Claim 18 (depends on 17)

The metal complex of claim 17, wherein Lb is, at each occurrence identically or differently, selected from the following structure:
wherein R1 to R7 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

### Claim 19 (depends on 18)

The metal complex of claim 18, wherein at least one or two of R1 to R3 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms or combinations thereof; and/or at least one or two of R4 to R6 are selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms or combinations thereof.

### Claim 20 (depends on 16)

The metal complex of claim 16, wherein Lb is, at each occurrence identically or differently, selected from the group consisting of the following structures:
wherein, Lc is, at each occurrence identically or differently, selected from the group consisting of the following structures:

### Claim 21 (depends on 20)

The metal complex of claim 20, wherein the metal complex is an Ir complex and has a structure represented by any one of Ir(La)(Lb)(Lc), Ir(La)2(Lb), Ir(La)2(Lc) and Ir(La)(Lc)2; when the metal complex has a structure of Ir(La)(Lb)(Lc), La is selected from any one of the group consisting of La1 to La956, La985 to La1009, La1020 to La1074, La1097 to La1100, La1105 to La1342, Lb is selected from any one of the group consisting of Lb1 to Lb322, and Lc is selected from any one of the group consisting of LC1 to Lc231; when the metal complex has a structure of Ir(La)2(Lb), La is, at each occurrence identically or differently, selected from any one or any two of the group consisting of La1 to La956, La985 to La1009, La1020 to La1074, La1097 to La1100, La1105 to La1342, and Lb is selected from any one of the group consisting of Lb1 to Lb322; when the metal complex has a structure of Ir(La)2(Lc), La is, at each occurrence identically or differently, selected from any one or any two of the group consisting of La1 to La956, La985 to La1009, La1020 to La1074, La1097 to La1100, La1105 to La1342, and Lc is selected from any one of the group consisting of Lc1 to Lc231; and when the metal complex has a structure of Ir(La)(Lc)2, La is selected from any one of the group consisting of La1 to La956, La985 to La1009, La1020 to La1074, La1097 to La1100, La1105 to La1342, and Lc is, at each occurrence identically or differently, selected from any one or any two of the group consisting of Lc1 to Lc231.

### Claim 22 (depends on 20)

The metal complex of claim 20, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 530, and Compound 1 to Compound 530 have a general formula of Ir(La)2(Lb), wherein two La are identical and La and Lb are respectively selected from structures listed in the following table:
Compound
No.
La
Lb
1
La27
Lb31
2
La27
Lb57
3
La28
Lb31
4
La28
Lb57
5
La29
Lb31
6
La29
Lb57
7
La30
Lb31
8
La30
Lb57
9
La33
Lb31
10
La33
Lb57
11
La35
Lb31
12
La35
Lb57
13
La37
Lb31
14
La37
Lb57
15
La41
Lb31
16
La41
Lb57
17
La43
Lb31
18
La43
Lb57
19
La27
Lb66
20
La27
Lb88
21
La28
Lb66
22
La28
Lb88
23
La29
Lb66
24
La29
Lb88
25
La30
Lb66
26
La30
Lb88
27
La33
Lb66
28
La33
Lb88
29
La35
Lb66
30
La35
Lb88
31
La37
Lb66
32
La37
Lb88
33
La41
Lb66
34
La41
Lb88
35
La43
Lb66
36
La43
Lb88
37
La27
Lb90
38
La27
Lb122
39
La28
Lb90
40
La28
Lb122
41
La29
Lb90
42
La29
Lb122
43
La30
Lb90
44
La30
Lb122
45
La33
Lb90
46
La33
Lb122
47
La35
Lb90
48
La35
Lb122
49
La37
Lb90
50
La37
Lb122
51
La41
Lb90
52
La41
Lb122
53
La43
Lb90
54
La43
Lb122
55
La27
Lb126
56
La27
Lb139
57
La28
Lb126
58
La28
Lb139
59
La29
Lb126
60
La29
Lb139
61
La30
Lb126
62
La30
Lb139
63
La33
Lb126
64
La33
Lb139
65
La35
Lb126
66
La35
Lb139
67
La37
Lb126
68
La37
Lb139
69
La41
Lb126
70
La41
Lb139
71
La43
Lb126
72
La43
Lb139
73
La27
Lb245
74
La35
Lb245
75
La28
Lb245
76
La37
Lb245
77
La29
Lb245
78
La41
Lb245
79
La30
Lb245
80
La43
Lb245
81
La33
Lb245
82
La44
Lb245
83
La51
Lb31
84
La51
Lb57
85
La56
Lb31
86
La56
Lb57
87
La58
Lb31
88
La58
Lb57
89
La74
Lb31
90
La74
Lb57
91
La79
Lb31
92
La79
Lb57
93
La81
Lb31
94
La81
Lb57
95
La97
Lb31
96
La97
Lb57
97
La102
Lb31
98
La102
Lb57
99
La104
Lb31
100
La104
Lb57
101
La120
Lb31
102
La120
Lb57
103
La125
Lb31
104
La125
Lb57
105
La212
Lb31
106
La212
Lb57
107
La214
Lb31
108
La214
Lb57
109
La217
Lb31
110
La217
Lb57
111
La219
Lb31
112
La219
Lb57
113
La226
Lb31
114
La226
Lb57
115
La304
Lb31
116
La304
Lb57
117
La306
Lb31
118
La306
Lb57
119
La309
Lb31
120
La309
Lb57
121
La311
Lb31
122
La311
Lb57
123
La321
Lb31
124
La321
Lb57
125
La323
Lb31
126
La323
Lb57
127
La332
Lb31
128
La332
Lb57
129
La351
Lb31
130
La351
Lb57
131
La356
Lb31
132
La356
Lb57
133
La375
Lb31
134
La375
Lb57
135
La422
Lb31
136
La422
Lb57
137
La427
Lb31
138
La427
Lb57
139
La450
Lb31
140
La450
Lb57
141
La473
Lb31
142
La473
Lb57
143
La496
Lb31
144
La496
Lb57
145
La606
Lb31
146
La606
Lb57
147
La611
Lb31
148
La611
Lb57
149
La634
Lb31
150
La634
Lb57
151
La899
Lb31
152
La899
Lb57
153
La923
Lb31
154
La923
Lb57
155
La51
Lb66
156
La51
Lb88
157
La56
Lb66
158
La56
Lb88
159
La58
Lb66
160
La58
Lb88
161
La74
Lb66
162
La74
Lb88
163
La79
Lb66
164
La79
Lb88
165
La81
Lb66
166
La81
Lb88
167
La97
Lb66
168
La97
Lb88
169
La102
Lb66
170
La102
Lb88
171
La104
Lb66
172
La104
Lb88
173
La120
Lb66
174
La120
Lb88
175
La125
Lb66
176
La125
Lb88
177
La212
Lb66
178
La212
Lb88
179
La214
Lb66
180
La214
Lb88
181
La217
Lb66
182
La217
Lb88
183
La219
Lb66
184
La219
Lb88
185
La226
Lb66
186
La226
Lb88
187
La304
Lb66
188
La304
Lb88
189
La306
Lb66
190
La306
Lb88
191
La309
Lb66
192
La309
Lb88
193
La311
Lb66
194
La311
Lb88
195
La321
Lb66
196
La321
Lb88
197
La323
Lb66
198
La323
Lb88
199
La332
Lb66
200
La332
Lb88
201
La351
Lb66
202
La351
Lb88
203
La356
Lb66
204
La356
Lb88
205
La375
Lb66
206
La375
Lb88
207
La422
Lb66
208
La422
Lb88
209
La427
Lb66
210
La427
Lb88
211
La450
Lb66
212
La450
Lb88
213
La473
Lb66
214
La473
Lb88
215
La496
Lb66
216
La496
Lb88
217
La606
Lb66
218
La606
Lb88
219
La611
Lb66
220
La611
Lb88
221
La634
Lb66
222
La634
Lb88
223
La899
Lb66
224
La899
Lb88
225
La923
Lb66
226
La923
Lb88
227
La51
Lb90
228
La51
Lb122
229
La56
Lb90
230
La56
Lb122
231
La58
Lb90
232
La58
Lb122
233
La74
Lb90
234
La74
Lb122
235
La79
Lb90
236
La79
Lb122
237
La81
Lb90
238
La81
Lb122
239
La97
Lb90
240
La97
Lb122
241
La102
Lb90
242
La102
Lb122
243
La104
Lb90
244
La104
Lb122
245
La120
Lb90
246
La120
Lb122
247
La125
Lb90
248
La125
Lb122
249
La212
Lb90
250
La212
Lb122
251
La214
Lb90
252
La214
Lb122
253
La217
Lb90
254
La217
Lb122
255
La219
Lb90
256
La219
Lb122
257
La226
Lb90
258
La226
Lb122
259
La304
Lb90
260
La304
Lb122
261
La306
Lb90
262
La306
Lb122
263
La309
Lb90
264
La309
Lb122
265
La311
Lb90
266
La311
Lb122
267
La321
Lb90
268
La321
Lb122
269
La323
Lb90
270
La323
Lb122
271
La332
Lb90
272
La332
Lb122
273
La351
Lb90
274
La351
Lb122
275
La356
Lb90
276
La356
Lb122
277
La375
Lb90
278
La375
Lb122
279
La422
Lb90
280
La422
Lb122
281
La427
Lb90
282
La427
Lb122
283
La450
Lb90
284
La450
Lb122
285
La473
Lb90
286
La473
Lb122
287
La496
Lb90
288
La496
Lb122
289
La606
Lb90
290
La606
Lb122
291
La611
Lb90
292
La611
Lb122
293
La634
Lb90
294
La634
Lb122
295
La899
Lb90
296
La899
Lb122
297
La923
Lb90
298
La923
Lb122
299
La51
Lb126
300
La51
Lb139
301
La56
Lb126
302
La56
Lb139
303
La58
Lb126
304
La58
Lb139
305
La74
Lb126
306
La74
Lb139
307
La79
Lb126
308
La79
Lb139
309
La81
Lb126
310
La81
Lb139
311
La97
Lb126
312
La97
Lb139
313
La102
Lb126
314
La102
Lb139
315
La104
Lb126
316
La104
Lb139
317
La120
Lb126
318
La120
Lb139
319
La125
Lb126
320
La125
Lb139
321
La212
Lb126
322
La212
Lb139
323
La214
Lb126
324
La214
Lb139
325
La217
Lb126
326
La217
Lb139
327
La219
Lb126
328
La219
Lb139
329
La226
Lb126
330
La226
Lb139
331
La304
Lb126
332
La304
Lb139
333
La306
Lb126
334
La306
Lb139
335
La309
Lb126
336
La309
Lb139
337
La311
Lb126
338
La311
Lb139
339
La321
Lb126
340
La321
Lb139
341
La323
Lb126
342
La323
Lb139
343
La332
Lb126
344
La332
Lb139
345
La351
Lb126
346
La351
Lb139
347
La356
Lb126
348
La356
Lb139
349
La375
Lb126
350
La375
Lb139
351
La422
Lb126
352
La422
Lb139
353
La427
Lb126
354
La427
Lb139
355
La450
Lb126
356
La450
Lb139
357
La473
Lb126
358
La473
Lb139
359
La496
Lb126
360
La496
Lb139
361
La606
Lb126
362
La606
Lb139
363
La611
Lb126
364
La611
Lb139
365
La634
Lb126
366
La634
Lb139
367
La899
Lb126
368
La899
Lb139
369
La923
Lb126
370
La923
Lb139
371
La51
Lb245
372
La309
Lb245
373
La56
Lb245
374
La311
Lb245
375
La58
Lb245
376
La321
Lb245
377
La74
Lb245
378
La323
Lb245
379
La79
Lb245
380
La332
Lb245
381
La81
Lb245
382
La351
Lb245
383
La97
Lb245
384
La356
Lb245
385
La102
Lb245
386
La375
Lb245
387
La104
Lb245
388
La422
Lb245
389
La120
Lb245
390
La427
Lb245
391
La125
Lb245
392
La450
Lb245
393
La212
Lb245
394
La473
Lb245
395
La214
Lb245
396
La496
Lb245
397
La217
Lb245
398
La606
Lb245
399
La219
Lb245
400
La611
Lb245
401
La226
Lb245
402
La634
Lb245
403
La304
Lb245
404
La899
Lb245
405
La306
Lb245
406
La923
Lb245
407
La993
Lb31
408
La993
Lb90
409
La997
Lb31
410
La997
Lb90
411
La1008
Lb31
412
La1008
Lb90
413
La995
Lb31
414
La995
Lb90
415
La1300
Lb31
416
La1300
Lb88
417
La1308
Lb31
418
La1308
Lb88
419
La1314
Lb31
420
La1314
Lb88
421
La1315
Lb31
422
La1315
Lb88
423
La1316
Lb31
424
La1316
Lb88
425
La1317
Lb31
426
La1317
Lb88
427
La1321
Lb31
428
La1321
Lb88
429
La1323
Lb31
430
La1323
Lb88
431
La1324
Lb31
432
La1324
Lb88
433
La1326
Lb31
434
La1326
Lb88
435
La1330
Lb31
436
La1330
Lb88
437
La1331
Lb31
438
La1331
Lb88
439
La1334
Lb31
440
La1334
Lb88
441
La1335
Lb31
442
La1335
Lb88
443
La1338
Lb31
444
La1338
Lb88
445
La1339
Lb31
446
La1339
Lb88
447
La1340
Lb31
448
La1340
Lb88
449
La993
Lb122
450
La993
Lb126
451
La997
Lb122
452
La997
Lb126
453
La1008
Lb122
454
La1008
Lb126
455
La995
Lb122
456
La995
Lb126
457
La1300
Lb122
458
La1300
Lb126
459
La1308
Lb122
460
La1308
Lb126
461
La1314
Lb122
462
La1314
Lb126
463
La1315
Lb122
464
La1315
Lb126
465
La1316
Lb122
466
La1316
Lb126
467
La1317
Lb122
468
La1317
Lb126
469
La1321
Lb122
470
La1321
Lb126
471
La1323
Lb122
472
La1323
Lb126
473
La1324
Lb122
474
La1324
Lb126
475
La1326
Lb122
476
La1326
Lb126
477
La1330
Lb122
478
La1330
Lb126
479
La1331
Lb122
480
La1331
Lb126
481
La1334
Lb122
482
La1334
Lb126
483
La1335
Lb122
484
La1335
Lb126
485
La1338
Lb122
486
La1338
Lb126
487
La1339
Lb122
488
La1339
Lb126
489
La1340
Lb122
490
La1340
Lb126
491
La997
Lb139
492
La997
Lb135
493
La1008
Lb139
494
La1008
Lb135
495
La995
Lb139
496
La995
Lb135
497
La1300
Lb139
498
La1300
Lb135
499
La1308
Lb139
500
La1308
Lb135
501
La1314
Lb139
502
La1314
Lb135
503
La1315
Lb139
504
La1315
Lb135
505
La1316
Lb139
506
La1316
Lb135
507
La1317
Lb139
508
La1317
Lb135
509
La1321
Lb139
510
La1321
Lb135
511
La1323
Lb139
512
La1323
Lb135
513
La1324
Lb139
514
La1324
Lb135
515
La1326
Lb139
516
La1326
Lb135
517
La1330
Lb139
518
La1330
Lb135
519
La1331
Lb139
520
La1331
Lb135
521
La1334
Lb139
522
La1334
Lb135
523
La1335
Lb139
524
La1335
Lb135
525
La1338
Lb139
526
La1338
Lb135
527
La1339
Lb139
528
La1339
Lb135
529
La1340
Lb139
530
La1340
Lb135.

### Claim 23 (depends on 1)

An electroluminescent device, comprising:
an anode,
a cathode, and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex of claim 1.

### Claim 24 (depends on 23)

The electroluminescent device of claim 23, wherein the organic layer is an emissive layer, and the metal complex is a luminescent material.

### Claim 25 (depends on 24)

The electroluminescent device of claim 24, wherein the electroluminescent device emits red light or white light.

### Claim 26 (depends on 25)

The electroluminescent device of claim 25, wherein the emissive layer further comprises at least one host material.

### Claim 27 (depends on 1)

A compound composition, comprising the metal complex of claim 1.

### Claim 28 (depends on 1)

The metal complex of claim 1, wherein in the La, ring A, ring C are, at each occurrence identically or differently, selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, an aza-naphthalene ring, a furan ring, a thiophene ring, an isoxazole ring, an isothiazole ring, a pyrrole ring, a pyrazole ring, a benzofuran ring, a benzothiophene ring, an azabenzofuran ring or an azabenzothiophene ring.