# US 2021/0280803 A1 · Organic electroluminescent materials and devices

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- Number: US 2021/0280803 A1
- Document ID: US20210280803A1
- Status: Published application
- Kind: A1
- Application number: 17/325,829
- Filed: 2021-05-20
- Published: 2021-09-09
- Earliest claimed: 2014-11-12
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Pierre-Luc T. BOUDREAULT; Harvey WENDT; Chuanjun XIA
- Web page: https://patentgrep.com/patent/US20210280803A1

## CPC

- H10K 85/342: {comprising iridium}
- C07F 15/0033: {Iridium compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- 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

A compound having a formula M(LA)x(LB)y(LC)z, where ligand LA is ligand LB is and ligand LC is is disclosed. In formula M(LA)x(LB)y(LC)z, M is a metal having an atomic number greater than 40; x is 1 or 2; y and z are independently 0, 1, or 2; x+y+z is the oxidation state of the metal M; A1-A8 are carbon or nitrogen; ring B is bonded to ring A through a C—C bond; M is bonded to ring A through a M-C bond; X is O, S, Se, CRR′, or NR1; rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; at least one R4 is a five-membered or six-membered heterocyclic ring which can be further substituted by RE; each R substituent is independently selected from the general substituents; and any adjacent R substitutents are optionally joined to form a ring.

## Claims

### Claim 1

A compound having a formula M(LA)x(LB)y(LC)z:
wherein the ligand LA is
wherein the ligand LB is
wherein the ligand LC is
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, or 2;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein A1, A2, A3, A4, A5, A6, A7, and A8 are carbon or nitrogen;
wherein ring B is bonded to ring A through a C—C bond;
wherein M is bonded to ring A through a M-C bond;
wherein X is selected from the group consisting of O, S, Se, CRR′, and NR1;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R3 represents mono, or di-substitution, or no substitution;
wherein R2, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein R4 represents mono, di, tri, or tetra-substitution;
wherein at least one R4 is a five-membered or six-membered heterocyclic ring which can be further substituted by RE;
wherein RE represents mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any adjacent substitutents of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE are optionally joined to form a ring.

### Claim 2 (depends on 1)

The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound has the formula M(LA)2(LC) or the formula M(LA)(LB)2.

### Claim 4 (depends on 1)

The compound of claim 1, wherein A1, A2, A3, A4, A5, A6, A7, and A8 are carbon.

### Claim 5 (depends on 1)

The compound of claim 1, wherein X is O or NR1.

### Claim 6 (depends on 1)

The compound of claim 1, wherein at least one R4 is a five-membered or six-membered aromatic heterocyclic ring.

### Claim 7 (depends on 1)

The compound of claim 1, wherein at least one R4 is a six-membered aromatic heterocyclic ring where the only heteroatom is nitrogen.

### Claim 8 (depends on 1)

The compound of claim 1, wherein at least one R4 is pyridine, triazine, pyrazine, pyrimidine, or pyridazine.

### Claim 9 (depends on 1)

The compound of claim 1, wherein LC has the formula:
wherein R5, R6, R7, and R8 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;
wherein at least one of R5, R6, R7, and R8 has at least two C atoms.

### Claim 10 (depends on 1)

The compound of claim 1, wherein each of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE is independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

### Claim 11 (depends on 1)

The compound of claim 1, wherein ring C is benzene, and ring D is pyridine.

### Claim 12 (depends on 1)

The compound of claim 1, wherein LA is selected from the group consisting of:

### Claim 13 (depends on 1)

The compound of claim 1, wherein LA is selected from the group consisting of:
LA1 through LA8, each represented
by the formula:
wherein in LA1: R1 = RA1 and R2 = RB1,
in LA2: R1 = RA2 and R2 = RB1,
in LA3: R1 = RA3, R2 = RB1,
in LA4: R1 = RA4, R2 = RB1,
in LA5: R1 = RA1, R2 = RB2,
in LA6: R1 = RA2, R2 = RB2,
in LA7: R1 = RA3, R2 = RB2, and
in LA8: R1 = RA4, R2 = RB2,
LA9 through LA16, each represented
by the formula:
wherein in LA9: R1 = RA1, R2 = RB1,
in LA10: R1 = RA2, R2 = RB1,
in LA11: R1 = RA3, R2 = RB1,
in LA12: R1 = RA4, R2 = RB1,
in LA13: R1 = RA1, R2 = RB2,
in LA14: R1 = RA2, R2 = RB2,
in LA15: R1 = RA3, R2 = RB2, and
in LA16: R1 = RA4, R2 = RB2,
LA17 through LA24, each represented
by the formula:
wherein LA17: R1 = RA1, R2 = RB1,
in LA18: R1 = RA2, R2 = RB1,
in LA19: R1 = RA3, R2 = RB1,
in LA20: R1 = RA4, R2 = RB1,
in LA21: R1 = RA1, R2 = RB2,
in LA22: R1 = RA2, R2 = RB2,
in LA23: R1 = RA3, R2 = RB2, and
in LA24: R1 = RA4, R2 = RB2,
LA25 through LA32, each represented
by the formula:
wherein in LA25: R1 = RA1, R2 = RB1,
in LA26: R1 = RA2, R2 = RB1,
in LA27: R1 = RA3, R2 = RB1,
in LA28: R1 = RA4, R2 = RB1,
in LA29: R1 = RA1, R2 = RB2,
in LA30: R1 = RA2, R2 = RB2,
in LA31: R1 = RA3, R2 = RB2, and
in LA32: R1 = RA4, R2 = RB2,
LA33 through LA40, each represented
by the formula:
wherein in LA33: R1 = RA1, R2 = RB1,
in LA34: R1 = RA2, R2 = RB1,
in LA35: R1 = RA3, R2 = RB1,
in LA36: R1 = RA4, R2 = RB1,
in LA37: R1 = RA1, R2 = RB2,
in LA38: R1 = RA2, R2 = RB2,
in LA39: R1 = RA3, R2 = RB2, and
in LA40: R1 = RA4, R2 = RB2,
LA41 through LA48, each represented
by the formula:
where in LA41: R1 = RA1, R2 = RB1,
in LA42: R1 = RA2, R2 = RB1,
in LA43: R1 = RA3, R2 = RB1,
in LA44: R1 = RA4, R2 = RB1,
in LA45: R1 = RA1, R2 = RB2,
in LA46: R1 = RA2, R2 = RB2,
in LA47: R1 = RA3, R2 = RB2, and
in LA48: R1 = RA4, R2 = RB2,
LA49 through LA56, each represented
by the formula:
wherein in LA49: R1 = RA1, R2 = RB1,
in LA50: R1 = RA2, R2 = RB1,
in LA51: R1 = RA3, R2 = RB1,
in LA52: R1 = RA4, R2 = RB1,
in LA53: R1 = RA1, R2 = RB2,
in LA54: R1 = RA2, R2 = RB2,
in LA55: R1 = RA3, R2 = RB2, and
in LA56: R1 = RA4, R2 = RB2,
LA57 through LA64, each represented
by the formula:
where in LA57: R1 = RA1, R2 = RB1,
in LA58: R1 = RA2, R2 = RB1,
in LA59: R1 = RA3, R2 = RB1,
in LA60: R1 = RA4, R2 = RB1,
in LA61: R1 = RA1, R2 = RB2,
in LA62: R1 = RA2, R2 = RB2,
in LA63: R1 = RA3, R2 = RB2, and
in LA64: R1 = RA4, R2 = RB2,
LA65 through LA72, each represented
by the formula:
wherein in LA65: R1 = RA1, R2 = RB1,
in LA66: R1 = RA2, R2 = RB1,
in LA67: R1 = RA3, R2 = RB1,
in LA68: R1 = RA4, R2 = RB1,
in LA69: R1 = RA1, R2 = RB2,
in LA70: R1 = RA2, R2 = RB2,
in LA71: R1 = RA3, R2 = RB2, and
in LA72: R1 = RA4, R2 = RB2,
LA73 through LA80, each represented
by the formula:
wherein in LA73: R1 = RA1, R2 = RB1,
in LA74: R1 = RA2, R2 = RB1,
in LA75: R1 = RA3, R2 = RB1,
in LA76: R1 = RA4, R2 = RB1,
in LA77: R1 = RA1, R2 = RB2,
in LA78: R1 = RA2, R2 = RB2,
in LA79: R1 = RA3, R2 = RB2, and
in LA80: R1 = RA4, R2 = RB2,
LA81 through LA88, each represented
by the formula:
wherein in LA81: R1 = RA1, R2 = RB1,
in LA82: R1 = RA2, R2 = RB1,
in LA83: R1 = RA3, R2 = RB1,
in LA84: R1 = RA4, R2 = RB1,
in LA85: R1 = RA1, R2 = RB2,
in LA86: R1 = RA2, R2 = RB2,
in LA87: R1 = RA3, R2 = RB2, and
in LA88: R1 = RA4, R2 = RB2,
LA89 through LA96, each represented
by the formula:
wherein in LA89: R1 = RA1, R2 = RB1,
in LA90: R1 = RA2, R2 = RB1,
in LA91: R1 = RA3, R2 = RB1,
in LA92: R1 = RA4, R2 = RB1,
in LA93: R1 = RA1, R2 = RB2,
in LA94: R1 = RA2, R2 = RB2,
in LA95: R1 = RA3, R2 = RB2, and
in LA96: R1 = RA4, R2 = RB2,
LA97 through LA100, each represented
by the formula:
where in LA97: X = O, R2 = RB1,
in LA98: X = O, R2 = RB2,
in LA99: X = S, R2 = RB1, and
in LA100: X = S, R2 = RB2.
LA101 through LA104, each represented
by the formula:
wherein in LA101: X = O, R2 = RB1,
in LA102: X = O, R2 = RB2,
in LA103: X = S, R2 = RB1, and
in LA104: X = S, R2 = RB2.
LA105 through LA110, each represented
by the formula:
wherein in LA105: X = O, R2 = RB1,
in LA106: X = O, R2 = RB2,
in LA107: X = S, R2 = RB1,
in LA108: X = S, R2 = RB2,
in LA109: X = C(CH3)2, R2 = RB1, and
in LA110: X = C(CH3)2, R2 = RB2.
LA111 through LA116, each represented
by the formula:
wherein in LA111: X = O, R2 = RB1,
in LA112: X = O, R2 = RB2,
in LA113: X = S, R2 = RB1,
in LA114: X = S, R2 = RB2,
in LA115: X = C(CH3)2, R2 = RB1, and
in LA116: X = C(CH3)2, R2 = RB2.
LA117 through LA122, each represented
by the formula:
wherein in LA117: X = O, R2 = RB1,
in LA118: X = O, R2 = RB2,
in LA119: X = S, R2 = RB1,
in LA120: X = S, R2 = RB2,
in LA121: X = C(CH3)2, R2 = RB1, and
in LA122: X = C(CH3)2, R2 = RB2.
LA123 through LA128, each represented
by the formula:
wherein in LA123: X = O, R2 = RB1,
in LA124: X = O, R2 = RB2,
in LA125: X = S, R2 = RB1,
in LA126: X = S, R2 = RB2,
in LA127: X = C(CH3)2, R2 = RB1, and
in LA128: X = C(CH3)2, R2 = RB2.
LA129 through LA134, each represented
by the formula:
wherein in LA129: X = O, R2 = RB1,
in LA130: X = O, R2 = RB2,
in LA131: X = S, R2 = RB1,
in LA132: X = S, R2 = RB2,
in LA133: X = C(CH3)2, R2 = RB1, and
in LA134: X = C(CH3)2, R2 = RB2.
LA135 through LA140, each represented
by the formula:
wherein in LA135: X = O, R2 = RB1,
in LA136: X = O, R2 = RB2,
in LA137: X = S, R2 = RB1,
in LA138: X = S, R2 = RB2,
in LA139: X = C(CH3)2, R2 = RB1, and
in LA140: X = C(CH3)2, R2 = RB2.
LA141 through LA146, each represented
by the formula:
wherein in LA141: X = O, R2 = RB1,
in LA142: X = O, R2 = RB2,
in LA143: X = S, R2 = RB1,
in LA144: X = S, R2 = RB2,
in LA145: X = C(CH3)2, R2 = RB1, and
in LA146: X = C(CH3)2, R2 = RB2.
LA147 through LA152, each represented
by the formula:
wherein in LA147: R1 = RA1, R2 = RB1,
in LA148: R1 = RA2, R2 = RB1,
in LA149: R1 = RA1, R2 = RB2,
in LA150: R1 = RA2, R2 = RB2,
in LA151: X = C(CH3)2, R2 = RB1, and
in LA152: X = C(CH3)2, R2 = RB2.
LA153 through LA158, each represented
by the formula:
wherein in LA153: R1 = RA1, R2 = RB1,
in LA154: R1 = RA2, R2 = RB1,
in LA155: R1 = RA1, R2 = RB2,
in LA156: R1 = RA2, R2 = RB2,
in LA157: X = C(CH3)2, R2 = RB1, and
in LA158: X = C(CH3)2, R2 = RB2.
LA159 through LA164, each represented
by the formula:
wherein in LA159: X = O, R2 = RB1,
in LA160: X = O, R2 = RB2,
in LA161: X = S, R2 = RB1,
in LA162: X = S, R2 = RB2,
in LA163: X = C(CH3)2, R2 = RB1, and
in LA164: X = C(CH3)2, R2 = RB2.
LA165 through LA170, each represented
by the formula:
wherein in LA165: X = O, R2 = RB1,
in LA166: X = O, R2 = RB2,
in LA167: X = S, R2 = RB1,
in LA168: X = S, R2 = RB2,
in LA169: X = C(CH3)2, R2 = RB1, and
in LA170: X = C(CH3)2, R2 = RB2.
LA171 through LA176, each represented
by the formula:
wherein in LA171: X = O, R2 = RB1,
in LA172: X = O, R2 = RB2,
in LA173: X = S, R2 = RB1,
in LA174: X = S, R2 = RB2,
in LA175: X = C(CH3)2, R2 = RB1, and
in LA176: X = C(CH3)2, R2 = RB2.
LA177 through LA182, each represented
by the formula:
wherein in LA177: X = O, R2 = RB1,
in LA178: X = O, R2 = RB2,
in LA179: X = S, R2 = RB1,
in LA180: X = S, R2 = RB2,
in LA181: X = C(CH3)2, R2 = RB1, and
in LA182: X = C(CH3)2, R2 = RB2.
wherein RA1 to RA4 have the following structures:
wherein RB1 and RB2 have the following structures:
LA183 through LA198, each represented
by the formula:
wherein in LA183: X = O, RE = RA5, R2 = RB1,
in LA184: X = O, RE = RA5, R2 = RB2,
in LA185: X = O, RE = RA6, R2 = RB1,
in LA186: X = O, RE = RA6, R2 = RB2,
in LA187: X = O, RE = RA7, R2 = RB1,
in LA188: X = O, RE = RA7, R2 = RB2,
in LA189: X = O, RE = RA8, R2 = RB1,
in LA190: X = O, RE = RA8, R2 = RB2,
in LA191: X = S, RE = RA5, R2 = RB1,
in LA192: X = S, RE = RA5, R2 = RB2,
in LA193: X = S, RE = RA6, R2 = RB1,
in LA194: X = S, RE = RA6, R2 = RB2,
in LA195: X = S, RE = RA7, R2 = RB1,
in LA196: X = S, RE = RA7, R2 = RB2,
in LA197: X = S, RE = RA8, R2 = RB1, and
in LA198: X = S, RE = RA8, R2 = RB2.
LA199 through LA214, each represented
by the formula:
wherein in LA199: X = O, RE = RA5, R2 = RB1,
in LA200: X = O, RE = RA5, R2 = RB2,
in LA201: X = O, RE = RA6, R2 = RB1,
in LA202: X = O, RE = RA6, R2 = RB2,
in LA203: X = O, RE = RA7, R2 = RB1,
in LA204: X = O, RE = RA7, R2 = RB2,
in LA205: X = O, RE = RA8, R2 = RB1,
in LA206: X = O, RE = RA8, R2 = RB2,
in LA207: X = S, RE = RA5, R2 = RB1,
in LA208: X = S, RE = RA5, R2 = RB2,
in LA209: X = S, RE = RA6, R2 = RB1,
in LA210: X = S, RE = RA6, R2 = RB2,
in LA211: X = S, RE = RA7, R2 = RB1,
in LA212: X = S, RE = RA7, R2 = RB2,
in LA213: X = S, RE = RA8, R2 = RB1, and
in LA214: X = S, RE = RA8, R2 = RB2.
wherein
LA215 through LA230, each represented
by the formula:
wherein in LA215: X = O, RE = RA5, R2 = RB1,
in LA216: X = O, RE = RA5, R2 = RB2,
in LA217: X = O, RE = RA6, R2 = RB1,
in LA218: X = O, RE = RA6, R2 = RB2,
in LA219: X = O, RE = RA7, R2 = RB1,
in LA220: X = O, RE = RA7, R2 = RB2,
in LA221: X = O, RE = RA8, R2 = RB1,
in LA222: X = O, RE = RA8, R2 = RB2,
in LA223: X = S, RE = RA5, R2 = RB1,
in LA224: X = S, RE = RA5, R2 = RB2,
in LA225: X = S, RE = RA6, R2 = RB1,
in LA226: X = S, RE = RA6, R2 = RB2,
in LA227: X = S, RE = RA7, R2 = RB1,
in LA228: X = S, RE = RA7, R2 = RB2,
in LA229: X = S, RE = RA8, R2 = RB1, and
in LA230: X = S, RE = RA8, R2 = RB2.
LA231 through LA246, each represented
by the formula:
wherein in LA231: X = O, RE = RA5, R2 = RB1,
in LA232: X = O, RE = RA5, R2 = RB2,
in LA233: X = O, RE = RA6, R2 = RB1,
in LA234: X = O, RE = RA6, R2 = RB2,
in LA235: X = O, RE = RA7, R2 = RB1,
in LA236: X = O, RE = RA7, R2 = RB2,
in LA237: X = O, RE = RA8, R2 = RB1,
in LA238: X = O, RE = RA8, R2 = RB2,
in LA239: X = S, RE = RA5, R2 = RB1,
in LA240: X = S, RE = RA5, R2 = RB2,
in LA241: X = S, RE = RA6, R2 = RB1,
in LA242: X = S, RE = RA6, R2 = RB2,
in LA243: X = S, RE = RA7, R2 = RB1,
in LA244: X = S, RE = RA7, R2 = RB2,
in LA245: X = S, RE = RA8, R2 = RB1, and
in LA246: X = S, RE = RA8, R2 = RB2.
LA247 through LA262, each represented
by the formula:
wherein in LA247: X = O, RE = RA5, R2 = RB1,
in LA248: X = O, RE = RA5, R2 = RB2,
in LA249: X = O, RE = RA6, R2 = RB1,
in LA250: X = O, RE = RA6, R2 = RB2,
in LA251: X = O, RE = RA7, R2 = RB1,
in LA252: X = O, RE = RA7, R2 = RB2,
in LA253: X = O, RE = RA8, R2 = RB1,
in LA254: X = O, RE = RA8, R2 = RB2,
in LA255: X = S, RE = RA5, R2 = RB1,
in LA256: X = S, RE = RA5, R2 = RB2,
in LA257: X = S, RE = RA6, R2 = RB1,
in LA258: X = S, RE = RA6, R2 = RB2,
in LA259: X = S, RE = RA7, R2 = RB1,
in LA260: X = S, RE = RA7, R2 = RB2,
in LA261: X = S, RE = RA8, R2 = RB1, and
in LA262: X = S, RE = RA8, R2 = RB2.
LA263 through LA278, each represented
by the formula:
wherein in LA263: X = O, RE = RA5, R2 = RB1,
in LA264: X = O, RE = RA5, R2 = RB2,
in LA265: X = O, RE = RA6, R2 = RB1,
in LA266: X = O, RE = RA6, R2 = RB2,
in LA267: X = O, RE = RA7, R2 = RB1,
in LA268: X = O, RE = RA7, R2 = RB2,
in LA269: X = O, RE = RA8, R2 = RB1,
in LA270: X = O, RE = RA8, R2 = RB2,
in LA271: X = S, RE = RA5, R2 = RB1,
in LA272: X = S, RE = RA5, R2 = RB2,
in LA273: X = S, RE = RA6, R2 = RB1,
in LA274: X = S, RE = RA6, R2 = RB2,
in LA275: X = S, RE = RA7, R2 = RB1,
in LA276: X = S, RE = RA7, R2 = RB2,
in LA277: X = S, RE = RA8, R2 = RB1, and
in LA278: X = S, RE = RA8, R2 = RB2.
LA279 through LA294, each represented
by the formula:
wherein in LA279: X = O, RE = RA5, R2 = RB1,
in LA280: X = O, RE = RA5, R2 = RB2,
in LA281: X = O, RE = RA6, R2 = RB1,
in LA282: X = O, RE = RA6, R2 = RB2,
in LA283: X = O, RE = RA7, R2 = RB1,
in LA284: X = O, RE = RA7, R2 = RB2,
in LA285: X = O, RE = RA8, R2 = RB1,
in LA286: X = O, RE = RA8, R2 = RB2,
in LA287: X = S, RE = RA5, R2 = RB1,
in LA288: X = S, RE = RA5, R2 = RB2,
in LA289: X = S, RE = RA6, R2 = RB1,
in LA290: X = S, RE = RA6, R2 = RB2,
in LA291: X = S, RE = RA7, R2 = RB1,
in LA292: X = S, RE = RA7, R2 = RB2,
in LA293: X = S, RE = RA8, R2 = RB1, and
in LA294: X = S, RE = RA8, R2 = RB2.
LA295 through LA310, each represented
by the formula:
wherein in LA295: X = O, RE = RA5, R2 = RB1,
in LA296: X = O, RE = RA5, R2 = RB2,
in LA297: X = O, RE = RA6, R2 = RB1,
in LA298: X = O, RE = RA6, R2 = RB2,
in LA299: X = O, RE = RA7, R2 = RB1,
in LA300: X = O, RE = RA7, R2 = RB2,
in LA301: X = O, RE = RA8, R2 = RB1,
in LA302: X = O, RE = RA8, R2 = RB2,
in LA303: X = S, RE = RA5, R2 = RB1,
in LA304: X = S, RE = RA5, R2 = RB2,
in LA305: X = S , RE = RA6, R2 = RB1,
in LA306: X = S, RE = RA6, R2 = RB2,
in LA307: X = S, RE = RA7, R2 = RB1,
in LA308: X = S, RE = RA7, R2 = RB2,
in LA309: X = S, RE = RA8, R2 = RB1, and
in LA310: X = S, RE = RA8, R2 = RB2.
LA311 through LA326, each represented
by the formula:
wherein in LA311: RE = RA5, R2 = RB1, R1 = RC1,
in LA312: RE = RA5, R2 = RB2, R1 = RC1,
in LA313: RE = RA6, R2 = RB1, R1 = RC1,
in LA314: RE = RA6, R2 = RB2, R1 = RC1,
in LA315: RE = RA7, R2 = RB1, R1 = RC1,
in LA316: RE = RA7, R2 = RB2, R1 = RC1,
in LA317: RE = RA8, R2 = RB1, R1 = RC1,
in LA318: RE = RA8, R2 = RB2, R1 = RC1,
in LA319: RE = RA5, R2 = RB1, R1 = RC2,
in LA320: RE = RA5, R2 = RB2, R1 = RC2,
in LA321: RE = RA6, R2 = RB1, R1 = RC2,
in LA322: RE = RA6, R2 = RB2, R1 = RC2,
in LA323: RE = RA7, R2 = RB1, R1 = RC2,
in LA324: RE = RA7, R2 = RB2, R1 = RC2,
in LA325: RE = RA8, R2 = RB1, R1 = RC2, and
in LA326: RE = RA8, R2 = RB2, R1 = RC2.
LA327 through LA342, each represented
by the formula:
wherein in LA327: RE = RA5, R2 = RB1, R1 = RC1,
in LA328: RE = RA5, R2 = RB2, R1 = RC1,
in LA329: RE = RA6, R2 = RB1, R1 = RC1,
in LA330: RE = RA6, R2 = RB2, R1 = RC1,
in LA331: RE = RA7, R2 = RB1, R1 = RC1,
in LA332: RE = RA7, R2 = RB2, R1 = RC1,
in LA333: RE = RA8, R2 = RB1, R1 = RC1,
in LA334: RE = RA8, R2 = RB2, R1 = RC1,
in LA335: RE = RA5, R2 = RB1, R1 = RC2,
in LA336: RE = RA5, R2 = RB2, R1 = RC2,
in LA337: RE = RA6, R2 = RB1, R1 = RC2,
in LA338: RE = RA6, R2 = RB2, R1 = RC2,
in LA339: RE = RA7, R2 = RB1, R1 = RC2,
in LA340: RE = RA7, R2 = RB2, R1 = RC2,
in LA341: RE = RA8, R2 = RB1, R1 = RC2, and
in LA342: RE = RA8, R2 = RB2, R1 = RC2.
LA343 through LA358, each represented
by the formula:
wherein in LA343: RE = RA5, R2 = RB1, R1 = RC1,
in LA344: RE = RA5, R2 = RB2, R1 = RC1,
in LA345: RE = RA6, R2 = RB1, R1 = RC1,
in LA346: RE = RA6, R2 = RB2, R1 = RC1,
in LA347: RE = RA7, R2 = RB1, R1 = RC1,
in LA348: RE = RA7, R2 = RB2, R1 = RC1,
in LA349: RE = RA8, R2 = RB1, R1 = RC1,
in LA350: RE = RA8, R2 = RB2, R1 = RC1,
in LA351: RE = RA5, R2 = RB1, R1 = RC2,
in LA352: RE = RA5, R2 = RB2, R1 = RC2,
in LA353: RE = RA6, R2 = RB1, R1 = RC2,
in LA354: RE = RA6, R2 = RB2, R1 = RC2,
in LA355: RE = RA7, R2 = RB1, R1 = RC2,
in LA356: RE = RA7, R2 = RB2, R1 = RC2,
in LA357: RE = RA8, R2 = RB1, R1 = RC2, and
in LA358: RE = RA8, R2 = RB2, R1 = RC2.
LA359 through LA374, each represented
by the formula:
wherein in LA359: RE = RA5, R2 = RB1, R1 = RC1,
in LA360: RE = RA5, R2 = RB2, R1 = RC1,
in LA361: RE = RA6, R2 = RB1, R1 = RC1,
in LA362: RE = RA6, R2 = RB2, R1 = RC1,
in LA363: RE = RA7, R2 = RB1, R1 = RC1,
in LA364: RE = RA7, R2 = RB2, R1 = RC1,
in LA365: RE = RA8, R2 = RB1, R1 = RC1,
in LA366: RE = RA8, R2 = RB2, R1 = RC1,
in LA367: RE = RA5, R2 = RB1, R1 = RC2,
in LA368: RE = RA5, R2 = RB2, R1 = RC2,
in LA369: RE = RA6, R2 = RB1, R1 = RC2,
in LA370: RE = RA6, R2 = RB2, R1 = RC2,
in LA371: RE = RA7, R2 = RB1, R1 = RC2,
in LA372: RE = RA7, R2 = RB2, R1 = RC2,
in LA373: RE = RA8, R2 = RB1, R1 = RC2, and
in LA374: RE = RA8, R2 = RB2, R1 = RC2.
LA375 through LA382, each represented
by the formula:
wherein in LA375: X = O, RE = RA5,
in LA376: X = O, RE = RA6,
in LA377: X = O, RE = RA7,
in LA378: X = O, RE = RA8,
in LA379: X = S, RE = RA5,
in LA380: X = S, RE = RA6,
in LA381: X = S, RE = RA7, and
in LA382: X = S, RE = RA8.
LA383 through LA390, each represented
by the formula:
wherein in LA383: X = O, RE = RA5,
in LA384: X = O, RE = RA6,
in LA385: X = O, RE = RA7,
in LA386: X = O, RE = RA8,
in LA387: X = S, RE = RA5,
in LA388: X = S, RE = RA6,
in LA389: X = S, RE = RA7, and
in LA390: X = S, RE = RA8.
LA391 through LA406, each represented
by the formula:
wherein in LA391: X = O, RE = RA5, R2 = RB1,
in LA392: X = O, RE = RA5, R2 = RB2,
in LA393: X = O, RE = RA6, R2 = RB1,
in LA394: X = O, RE = RA6, R2 = RB2,
in LA395: X = O, RE = RA7, R2 = RB1,
in LA396: X = O, RE = RA7, R2 = RB2,
in LA397: X = O, RE = RA8, R2 = RB1,
in LA398: X = O, RE = RA8, R2 = RB2,
in LA399: X = S, RE = RA5, R2 = RB1,
in LA400: X = S, RE = RA5, R2 = RB2,
in LA401: X = S, RE = RA6, R2 = RB1,
in LA402: X = S, RE = RA6, R2 = RB2,
in LA403: X = S, RE = RA7, R2 = RB1,
in LA404: X = S, RE = RA7, R2 = RB2,
in LA405: X = S, RE = RA8, R2 = RB1, and
in LA406: X = S, RE = RA8, R2 = RB2.
LA407 through LA422, each represented
by the formula:
wherein in LA407: X = O, RE = RA5, R2 = RB1,
in LA408: X = O, RE = RA5, R2 = RB2,
in LA409: X = O, RE = RA6, R2 = RB1,
in LA410: X = O, RE = RA6, R2 = RB2,
in LA411: X = O, RE = RA7, R2 = RB1,
in LA412: X = O, RE = RA7, R2 = RB2,
in LA413: X = O, RE = RA8, R2 = RB1,
in LA414: X = O, RE = RA8, R2 = RB2,
in LA415: X = S, RE = RA5, R2 = RB1,
in LA416: X = S, RE = RA5, R2 = RB2,
in LA417: X = S, RE = RA6, R2 = RB1,
in LA418: X = S, RE = RA6, R2 = RB2,
in LA419: X = S, RE = RA7, R2 = RB1,
in LA420: X = S, RE = RA7, R2 = RB2,
in LA421: X = S, RE = RA8, R2 = RB1, and
in LA422: X = S, RE = RA8, R2 = RB2.
LA423 through LA438, each represented
by the formula:
wherein in LA423: X = O, RE = RA5, R4 = RB1,
in LA424: X = O, RE = RA5, R4 = RB2,
in LA425: X = O, RE = RA6, R4 = RB1,
in LA426: X = O, RE = RA6, R4 = RB2,
in LA427: X = O, RE = RA7, R4 = RB1,
in LA428: X = O, RE = RA7, R4 = RB2,
in LA429: X = O, RE = RA8, R4 = RB1,
in LA430: X = O, RE = RA8, R4 = RB2,
in LA431: X = S, RE = RA5, R4 = RB1,
in LA432: X = S, RE = RA5, R4 = RB2,
in LA433: X = S, RE = RA6, R4 = RB1,
in LA434: X = S, RE = RA6, R4 = RB2,
in LA435: X = S, RE = RA7, R4 = RB1,
in LA436: X = S, RE = RA7, R4 = RB2,
in LA437: X = S, RE = RA8, R4 = RB1, and
in LA438: X = S, RE = RA8, R4 = RB2.
LA439 through LA454, each represented
by the formula:
wherein in LA439: X = O, RE = RA5, R4 = RB1,
in LA440: X = O, RE = RA5, R4 = RB2,
in LA441: X = O, RE = RA6, R4 = RB1,
in LA442: X = O, RE = RA6, R4 = RB2,
in LA443: X = O, RE = RA7, R4 = RB1,
in LA444: X = O, RE = RA7, R4 = RB2,
in LA445: X = O, RE = RA8, R4 = RB1,
in LA446: X = O, RE = RA8, R4 = RB2,
in LA447: X = S, RE = RA5, R4 = RB1,
in LA448: X = S, RE = RA5, R4 = RB2,
in LA449: X = S, RE = RA6, R4 = RB1,
in LA450: X = S, RE = RA6, R4 = RB2,
in LA451: X = S, RE = RA7, R4 = RB1,
in LA452: X = S, RE = RA7, R4 = RB2,
in LA453: X = S, RE = RA8, R4 = RB1, and
in LA454: X = S, RE = RA8, R4 = RB2.
LA455 through LA462, each represented
by the formula:
wherein in LA455: X = O, RE = RA5,
in LA456: X = O, RE = RA6,
in LA457: X = O, RE = RA7,
in LA458: X = O, RE = RA8,
in LA459: X = S, RE = RA5,
in LA460: X = S, RE = RA6,
in LA461: X = S, RE = RA7, and
in LA462: X = S, RE = RA8.
LA463 through LA470, each represented
by the formula:
wherein in LA463: X = O, RE = RA5,
in LA464: X = O, RE = RA6,
in LA465: X = O, RE = RA7,
in LA466: X = O, RE = RA8,
in LA467: X = S, RE = RA5,
in LA468: X = S, RE = RA6,
in LA469: X = S, RE = RA7, and
in LA470: X = S, RE = RA8.
LA471 through LA478, each represented
by the formula:
wherein in LA471: RE = RA5, R1 = RC1,
in LA472: RE = RA6, R1 = RC1,
in LA473: RE = RA7, R1 = RC1,
in LA474: RE = RA8, R1 = RC1,
in LA475: RE = RA5, R1 = RC2,
in LA476: RE = RA6, R1 = RC2,
in LA477: RE = RA7, R1 = RC2, and
in LA478: RE = RA8, R1 = RC2.
LA479 through LA486, each represented
by the formula:
wherein in LA479: RE = RA5, R1 = RC1,
in LA480: RE = RA6, R1 = RC1,
in LA481: RE = RA7, R1 = RC1,
in LA482: RE = RA8, R1 = RC1,
in LA483: RE = RA5, R1 = RC2,
in LA484: RE = RA6, R1 = RC2,
in LA485: RE = RA7, R1 = RC2, and
in LA486: RE = RA8, R1 = RC2.
LA487 through LA494, each represented
by the formula:
wherein in LA487: RE = RA5, R1 = RC1,
in LA488: RE = RA6, R1 = RC1,
in LA489: RE = RA7, R1 = RC1,
in LA490: RE = RA8, R1 = RC1,
in LA491: RE = RA5, R1 = RC2,
in LA492: RE = RA6, R1 = RC2,
in LA493: RE = RA7, R1 = RC2, and
in LA494: RE = RA8, R1 = RC2.
LA495 through LA502, each represented
by the formula:
wherein in LA495: RE = RA5, R1 = RC1,
in LA496: RE = RA6, R1 = RC1,
in LA497: RE = RA7, R1 = RC1,
in LA498: RE = RA8, R1 = RC1,
in LA499: RE = RA5, R1 = RC2,
in LA500: RE = RA6, R1 = RC2,
in LA501: RE = RA7, R1 = RC2, and
in LA502: RE = RA8, R1 = RC2.
LA503 through LA518, each represented
by the formula:
wherein in LA503: X = O, RE = RA5, R2 = RB1,
in LA504: X = O, RE = RA5, R2 = RB2,
in LA505: X = O, RE = RA6, R2 = RB1,
in LA506: X = O, RE = RA6, R2 = RB2,
in LA507: X = O, RE = RA7, R2 = RB1,
in LA508: X = O, RE = RA7, R2 = RB2,
in LA509: X = O, RE = RA8, R2 = RB1,
in LA510: X = O, RE = RA8, R2 = RB2,
in LA511: X = S, RE = RA5, R2 = RB1,
in LA512: X = S, RE = RA5, R2 = RB2,
in LA513: X = S, RE = RA6, R2 = RB1,
in LA514: X = S, RE = RA6, R2 = RB2,
in LA515: X = S, RE = RA7, R2 = RB1,
in LA516: X = S, RE = RA7, R2 = RB2,
in LA517: X = S, RE = RA8, R2 = RB1, and
in LA518: X = S, RE = RA8, R2 = RB2.
LA519 through LA534, each represented
by the formula:
wherein in LA519: X = O, RE = RA5, R2 = RB1,
in LA520: X = O, RE = RA5, R2 = RB2,
in LA521: X = O, RE = RA6, R2 = RB1,
in LA522: X = O, RE = RA6, R2 = RB2,
in LA523: X = O, RE = RA7, R2 = RB1,
in LA524: X = O, RE = RA7, R2 = RB2,
in LA525: X = O, RE = RA8, R2 = RB1,
in LA526: X = O, RE = RA8, R2 = RB2,
in LA527: X = S, RE = RA5, R2 = RB1,
in LA528: X = S, RE = RA5, R2 = RB2,
in LA529: X = S, RE = RA6, R2 = RB1,
in LA530: X = S, RE = RA6, R2 = RB2,
in LA531: X = S, RE = RA7, R2 = RB1,
in LA532: X = S, RE = RA7, R2 = RB2,
in LA533: X = S, RE = RA8, R2 = RB1, and
in LA534: X = S, RE = RA8, R2 = RB2.
LA535 through LA550, each represented
by the formula:
wherein in LA535: X = O, RE = RA5, R2 = RB1,
in LA536: X = O, RE = RA5, R2 = RB2,
in LA537: X = O, RE = RA6, R2 = RB1,
in LA538: X = O, RE = RA6, R2 = RB2,
in LA539: X = O, RE = RA7, R2 = RB1,
in LA540: X = O, RE = RA7, R2 = RB2,
in LA541: X = O, RE = RA8, R2 = RB1,
in LA542: X = O, RE = RA8, R2 = RB2,
in LA543: X = S, RE = RA5, R2 = RB1,
in LA544: X = S, RE = RA5, R2 = RB2,
in LA545: X = S, RE = RA6, R2 = RB1,
in LA546: X = S, RE = RA6, R2 = RB2,
in LA547: X = S, RE = RA7, R2 = RB1,
in LA548: X = S, RE = RA7, R2 = RB2,
in LA549: X = S, RE = RA8, R2 = RB1, and
in LA550: X = S, RE = RA8, R2 = RB2.
LA551 through LA566, each represented
by the formula:
wherein in LA551: X = O, RE = RA5, R2 = RB1,
in LA552: X = O, RE = RA5, R2 = RB2,
in LA553: X = O, RE = RA6, R2 = RB1,
in LA554: X = O, RE = RA6, R2 = RB2,
in LA555: X = O, RE = RA7, R2 = RB1,
in LA556: X = O, RE = RA7, R2 = RB2,
in LA557: X = O, RE = RA8, R2 = RB1,
in LA558: X = O, RE = RA8, R2 = RB2,
in LA559: X = S, RE = RA5, R2 = RB1,
in LA560: X = S, RE = RA5, R2 = RB2,
in LA561: X = S, RE = RA6, R2 = RB1,
in LA562: X = S, RE = RA6, R2 = RB2,
in LA563: X = S, RE = RA7, R2 = RB1,
in LA564: X = S, RE = RA7, R2 = RB2,
in LA565: X = S, RE = RA8, R2 = RB1, and
in LA566: X = S, RE = RA8, R2 = RB2.
LA567 through LA582, each represented
by the formula:
wherein in LA567: X = O, RE = RA5, R2 = RB1,
in LA568: X = O, RE = RA5, R2 = RB2,
in LA569: X = O, RE = RA6, R2 = RB1,
in LA570: X = O, RE = RA6, R2 = RB2,
in LA571: X = O, RE = RA7, R2 = RB1,
in LA572: X = O, RE = RA7, R2 = RB2,
in LA573: X = O, RE = RA8, R2 = RB1,
in LA574: X = O, RE = RA8, R2 = RB2,
in LA575: X = S, RE = RA5, R2 = RB1,
in LA576: X = S, RE = RA5, R2 = RB2,
in LA577: X = S, RE = RA6, R2 = RB1,
in LA578: X = S, RE = RA6, R2 = RB2,
in LA579: X = S, RE = RA7, R2 = RB1,
in LA580: X = S, RE = RA7, R2 = RB2,
in LA581: X = S, RE = RA8, R2 = RB1, and
in LA582: X = S, RE = RA8, R2 = RB2.
LA583 through LA598, each represented
by the formula:
wherein in LA583: X = O, RE = RA5, R2 = RB1,
in LA584: X = O, RE = RA5, R2 = RB2,
in LA585: X = O, RE = RA6, R2 = RB1,
in LA586: X = O, RE = RA6, R2 = RB2,
in LA587: X = O, RE = RA7, R2 = RB1,
in LA588: X = O, RE = RA7, R2 = RB2,
in LA589: X = O, RE = RA8, R2 = RB1,
in LA590: X = O, RE = RA8, R2 = RB2,
in LA591: X = S, RE = RA5, R2 = RB1,
in LA592: X = S, RE = RA5, R2 = RB2,
in LA593: X = S, RE = RA6, R2 = RB1,
in LA594: X = S, RE = RA6, R2 = RB2,
in LA595: X = S, RE = RA7, R2 = RB1,
in LA596: X = S, RE = RA7, R2 = RB2,
in LA597: X = S, RE = RA8, R2 = RB1, and
in LA598: X = S, RE = RA8, R2 = RB2.
LA599 through LA606, each represented
by the formula:
wherein in LA599: RE = RA5, R1 = RC1,
in LA600: RE = RA6, R1 = RC1,
in LA601: RE = RA7, R1 = RC1,
in LA602: RE = RA8, R1 = RC1,
in LA603: RE = RA5, R1 = RC2,
in LA604: RE = RA6, R1 = RC2,
in LA605: RE = RA7, R1 = RC2, and
in LA606: RE = RA8, R1 = RC2.
LA607 through LA614, each represented
by the formula:
wherein in LA607: RE = RA5, R1 = RC1,
in LA608: RE = RA6, R1 = RC1,
in LA609: RE = RA7, R1 = RC1,
in LA610: RE = RA8, R1 = RC1,
in LA611: RE = RA5, R1 = RC2,
in LA612: RE = RA6, R1 = RC2,
in LA613: RE = RA7, R1 = RC2, and
in LA614: RE = RA8, R1 = RC2.
LA615 through LA622, each represented
by the formula:
wherein in LA615: RE = RA5, R1 = RC1,
in LA616: RE = RA6, R1 = RC1,
in LA617: RE = RA7, R1 = RC1,
in LA618: RE = RA8, R1 = RC1,
in LA619: RE = RA5, R1 = RC2,
in LA620: RE = RA6, R1 = RC2,
in LA621: RE = RA7, R1 = RC2, and
in LA622: RE = RA8, R1 = RC2.
LA623 through LA630, each represented
by the formula:
wherein in LA623: RE = RA5, R1 = RC1,
in LA624: RE = RA6, R1 = RC1,
in LA625: RE = RA7, R1 = RC1,
in LA626: RE = RA8, R1 = RC1,
in LA627: RE = RA5, R1 = RC2,
in LA628: RE = RA6, R1 = RC2,
in LA629: RE = RA7, R1 = RC2, and
in LA630: RE = RA8, R1 = RC2.
wherein RA5 to RA8 have the following structures:
wherein RB1 and RB2 have the following structures:
wherein RC1 to RC2 have the following structures:

### Claim 14 (depends on 13)

The compound of claim 13, wherein LB is selected from the group consisting of:

### Claim 15 (depends on 13)

The compound of claim 13, wherein LC is selected from the group consisting of:

### Claim 16 (depends on 13)

The compound of claim 13, wherein the compound is selected from the group consisting of Compound 1 through Compound 25,830;
where each Compound x has the formula Ir(LAk)(LBj)2;
wherein x=630j+k−630, k is an integer from 1 to 630, and j is an integer from 1 to 41; and wherein LB1 through LB41 are defined as follows:

### Claim 17 (depends on 13)

The compound of claim 13, wherein the compound is selected from the group consisting of Compound 25,831 through Compound 34,020;
where each Compound x has the formula Ir(LAk)2(LCi);
wherein x=(630i+k−630)+25,830, k is an integer from 1 to 630, and i is an integer from 1 to 13; and wherein LC1 through LC13 are defined as follows:

### Claim 18

A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(LA)x(LB)y(LC)z:
wherein the ligand LA is
wherein the ligand LB is
wherein the ligand LC is
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, or 2;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein A1, A2, A3, A4, A5, A6, A7, and A8 are carbon or nitrogen;
wherein ring B is bonded to ring A through a C—C bond;
wherein M is bonded to ring A through a M-C bond;
wherein X is selected from the group consisting of O, S, Se, CRR′, and NR1;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R3 represents mono, or di-substitution, or no substitution;
wherein R2, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein R4 represents mono, di, tri, or tetra-substitution;
wherein at least one R4 is a five-membered or six-membered heterocyclic ring which can be further substituted by RE;
wherein RE represents mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any adjacent substituents of R, R′, R1, R2, R3, R4, RC, RD, RX, RY, RZ and RE are optionally joined to form a ring.

### Claim 19 (depends on 18)

The device of claim 18, wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

### Claim 20 (depends on 18)

The device of claim 18, wherein the organic layer further comprises a host and the host is selected from the group consisting of:
and combinations thereof.