# US 10,873,036 B2 · Organic electroluminescent materials and devices

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- Number: US 10,873,036 B2
- Document ID: US10873036B2
- Status: Granted
- Kind: B2
- Application number: 15/202,845
- Filed: 2016-07-06
- Published: 2017-01-12
- Granted: 2020-12-22
- Earliest claimed: 2015-07-07
- Assignees: Universal Display Corporation
- Applicants: Universal Display Corporation
- Inventors: Pierre-Luc T. Boudreault; Chuanjun Xia
- Web page: https://patentgrep.com/patent/US10873036B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 5/027: {Organoboranes and organoborohydrides}
- C07F 7/0814: {said ring is substituted at a C ring atom by Si}
- C07F 7/12: Organo silicon halides
- C07F 9/5045: {Complexes or chelates of phosphines with metallic compounds or metals}
- C07F 15/0033: {Iridium compounds}
- C07F 15/0093: {without a metal-carbon linkage}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- H10K 85/342: {comprising iridium}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1051: with sulfur
- C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms
- C09K 2211/1092: containing sulfur 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 50/12: comprising dopants
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 2101/10: Triplet emission
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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

## Abstract

This invention discloses novel ligands for metal complexes. These ligands contain a phenyl with an iso-quinoline (or other type of heterocycles) which are bridged together with a carbon substituted by two aliphatic side chains. The resulting light-emitting metal complexes exhibited high external quantum efficiency and better line shape.

## Claims

### Claim 1

A compound of 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, 2, or 3;
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 X1, X2, X3, X4, X5, and X6 are each independently a CR or N;
wherein X7 is CH;
wherein X8 is carbon or nitrogen;
wherein when X6 is a CR, R is hydrogen;
wherein Y is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RCC, and RDD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R″, RCC, and RDD 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;
wherein each of RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein each of RX, RY, and RZ do not comprise alkenyl,
wherein when X1 to X5 is carbon, then R1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof; and when R1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein when at least one of X1 to X5 is nitrogen, then R1 is 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 R1, R, R′, RCC, RDD, RX, RY, and RZ are optionally joined or fused into 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 M is Ir.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound has the formula selected from the group consisting of M(LA)2(LC) and M(LA)(LB)2.

### Claim 5 (depends on 1)

The compound of claim 1, wherein X1, X2, X3, X4, X5, X6, and X7 are each a carbon.

### Claim 6 (depends on 1)

The compound of claim 1, wherein one of X1, X2, X3, X4, and X5 is nitrogen, and the rest of X1, X2, X3, X4, X5, X6, and X7 are carbon.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Y is CR′R″.

### Claim 8 (depends on 1)

The compound of claim 1, wherein ring C is benzene, and ring D is pyridine of which X8 is N.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
wherein each R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, and R20 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.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the ligand LA is selected from the group consisting of:
LA1 to LA165 based on the following formula:
RA
RB
RC
RD
RE
Y
LA1
H
H
H
H
H
C(CH3)2
LA2
H
RB1
H
H
H
C(CH3)2
LA3
H
RB2
H
H
H
C(CH3)2
LA4
H
RB3
H
H
H
C(CH3)2
LA5
H
RB4
H
H
H
C(CH3)2
LA6
H
RB5
H
H
H
C(CH3)2
LA7
H
RA2
H
H
H
C(CH3)2
LA8
H
RA22
H
H
H
C(CH3)2
LA9
H
RA28
H
H
H
C(CH3)2
LA10
H
H
H
H
H
NCH3
LA11
H
RB1
H
H
H
NCH3
LA12
H
RB2
H
H
H
NCH3
LA13
H
RB3
H
H
H
NCH3
LA14
H
RB4
H
H
H
NCH3
LA15
H
RB5
H
H
H
NCH3
LA16
H
RA2
H
H
H
NCH3
LA17
H
RA22
H
H
H
NCH3
LA18
H
RA28
H
H
H
NCH3
LA19
H
H
H
H
H
S
LA20
H
RB1
H
H
H
S
LA21
H
RB2
H
H
H
S
LA22
H
RB3
H
H
H
S
LA23
H
RB4
H
H
H
S
LA24
H
RB5
H
H
H
S
LA25
H
RA2
H
H
H
S
LA26
H
RA22
H
H
H
S
LA27
H
RA28
H
H
H
S
LA28
H
H
H
H
H
O
LA29
H
RB1
H
H
H
O
LA30
H
RB2
H
H
H
O
LA31
H
RB3
H
H
H
O
LA32
H
RB4
H
H
H
O
LA33
H
RB5
H
H
H
O
LA34
H
RA2
H
H
H
O
LA35
H
RA22
H
H
H
O
LA36
H
RA28
H
H
H
O
LA37
H
H
H
H
H
Si(CH3)2
LA38
H
RB1
H
H
H
Si(CH3)2
LA39
H
RB2
H
H
H
Si(CH3)2
LA40
H
RB3
H
H
H
Si(CH3)2
LA41
H
RB4
H
H
H
Si(CH3)2
LA42
H
RB5
H
H
H
Si(CH3)2
LA43
H
RA2
H
H
H
Si(CH3)2
LA44
H
RA22
H
H
H
Si(CH3)2
LA45
H
RA28
H
H
H
Si(CH3)2
LA46
H
H
RB1
H
H
C(CH3)2
LA47
H
H
RB2
H
H
C(CH3)2
LA48
H
H
RB3
H
H
C(CH3)2
LA49
H
H
RB4
H
H
C(CH3)2
LA50
H
H
RB5
H
H
C(CH3)2
LA51
H
H
RA2
H
H
C(CH3)2
LA52
H
H
RA22
H
H
C(CH3)2
LA53
H
H
RA28
H
H
C(CH3)2
LA54
H
H
RB1
H
H
NCH3
LA55
H
H
RB2
H
H
NCH3
LA56
H
H
RB3
H
H
NCH3
LA57
H
H
RB4
H
H
NCH3
LA58
H
H
RB5
H
H
NCH3
LA59
H
H
RA2
H
H
NCH3
LA60
H
H
RA22
H
H
NCH3
LA61
H
H
RA28
H
H
NCH3
LA62
H
H
RB1
H
H
S
LA63
H
H
RB2
H
H
S
LA64
H
H
RB3
H
H
S
LA65
H
H
RB4
H
H
S
LA66
H
H
RB5
H
H
S
LA67
H
H
RA2
H
H
S
LA68
H
H
RA22
H
H
S
LA69
H
H
RA28
H
H
S
LA70
H
H
RB1
H
H
O
LA71
H
H
RB2
H
H
O
LA72
H
H
RB3
H
H
O
LA73
H
H
RB4
H
H
O
LA74
H
H
RB5
H
H
O
LA75
H
H
RA2
H
H
O
LA76
H
H
RA22
H
H
O
LA77
H
H
RA28
H
H
O
LA78
H
H
RB1
H
H
Si(CH3)2
LA79
H
H
RB2
H
H
Si(CH3)2
LA80
H
H
RB3
H
H
Si(CH3)2
LA81
H
H
RB4
H
H
Si(CH3)2
LA82
H
H
RB5
H
H
Si(CH3)2
LA83
H
H
RA2
H
H
Si(CH3)2
LA84
H
H
RA22
H
H
Si(CH3)2
LA85
H
H
RA28
H
H
Si(CH3)2
LA86
H
H
H
RB1
H
C(CH3)2
LA87
H
H
H
RB2
H
C(CH3)2
LA88
H
H
H
RB3
H
C(CH3)2
LA89
H
H
H
RB4
H
C(CH3)2
LA90
H
H
H
RB5
H
C(CH3)2
LA91
H
H
H
RA2
H
C(CH3)2
LA92
H
H
H
RA22
H
C(CH3)2
LA93
H
H
H
RA28
H
C(CH3)2
LA94
H
H
H
RB1
H
NCH3
LA95
H
H
H
RB2
H
NCH3
LA96
H
H
H
RB3
H
NCH3
LA97
H
H
H
RB4
H
NCH3
LA98
H
H
H
RB5
H
NCH3
LA99
H
H
H
RA2
H
NCH3
LA100
H
H
H
RA22
H
NCH3
LA101
H
H
H
RA28
H
NCH3
LA102
H
H
H
RB1
H
S
LA103
H
H
H
RB2
H
S
LA104
H
H
H
RB3
H
S
LA105
H
H
H
RB4
H
S
LA106
H
H
H
RB5
H
S
LA107
H
H
H
RA2
H
S
LA108
H
H
H
RA22
H
S
LA109
H
H
H
RA28
H
S
LA110
H
H
H
RB1
H
O
LA111
H
H
H
RB2
H
O
LA112
H
H
H
RB3
H
O
LA113
H
H
H
RB4
H
O
LA114
H
H
H
RB5
H
O
LA115
H
H
H
RA2
H
O
LA116
H
H
H
RA22
H
O
LA117
H
H
H
RA28
H
O
LA118
H
H
H
RB1
H
Si(CH3)2
LA119
H
H
H
RB2
H
Si(CH3)2
LA120
H
H
H
RB3
H
Si(CH3)2
LA121
H
H
H
RB4
H
Si(CH3)2
LA122
H
H
H
RB5
H
Si(CH3)2
LA123
H
H
H
RA2
H
Si(CH3)2
LA124
H
H
H
RA22
H
Si(CH3)2
LA125
H
H
H
RA28
H
Si(CH3)2
LA126
H
H
H
H
RB1
C(CH3)2
LA127
H
H
H
H
RB2
C(CH3)2
LA128
H
H
H
H
RB3
C(CH3)2
LA129
H
H
H
H
RB4
C(CH3)2
LA130
H
H
H
H
RB5
C(CH3)2
LA131
H
H
H
H
RA2
C(CH3)2
LA132
H
H
H
H
RA22
C(CH3)2
LA133
H
H
H
H
RA28
C(CH3)2
LA134
H
H
H
H
RB1
NCH3
LA135
H
H
H
H
RB2
NCH3
LA136
H
H
H
H
RB3
NCH3
LA137
H
H
H
H
RB4
NCH3
LA138
H
H
H
H
RB5
NCH3
LA139
H
H
H
H
RA2
NCH3
LA140
H
H
H
H
RA22
NCH3
LA141
H
H
H
H
RA28
NCH3
LA142
H
H
H
H
RB1
S
LA143
H
H
H
H
RB2
S
LA144
H
H
H
H
RB3
S
LA145
H
H
H
H
RB4
S
LA146
H
H
H
H
RB5
S
LA147
H
H
H
H
RA2
S
LA148
H
H
H
H
RA22
S
LA149
H
H
H
H
RA28
S
LA150
H
H
H
H
RB1
O
LA151
H
H
H
H
RB2
O
LA152
H
H
H
H
RB3
O
LA153
H
H
H
H
RB4
O
LA154
H
H
H
H
RB5
O
LA155
H
H
H
H
RA2
O
LA156
H
H
H
H
RA22
O
LA157
H
H
H
H
RA28
O
LA158
H
H
H
H
RB1
Si(CH3)2
LA159
H
H
H
H
RB2
Si(CH3)2
LA160
H
H
H
H
RB3
Si(CH3)2
LA161
H
H
H
H
RB4
Si(CH3)2
LA162
H
H
H
H
RB5
Si(CH3)2
LA163
H
H
H
H
RA2
Si(CH3)2
LA164
H
H
H
H
RA22
Si(CH3)2
LA165
H
H
H
H
RA28
Si(CH3)2
LA331 to LA455 and LA581 to LA705 based on the following formula:
RA
RB
RC
RD
RF
RG
Y
LA331
H
H
H
H
H
H
C(CH3)2
LA332
H
RB1
H
H
H
H
C(CH3)2
LA333
H
RB2
H
H
H
H
C(CH3)2
LA334
H
RB3
H
H
H
H
C(CH3)2
LA335
H
RB4
H
H
H
H
C(CH3)2
LA336
H
RB5
H
H
H
H
C(CH3)2
LA337
H
RA2
H
H
H
H
C(CH3)2
LA338
H
RA22
H
H
H
H
C(CH3)2
LA339
H
RA28
H
H
H
H
C(CH3)2
LA340
H
H
H
H
H
H
NCH3
LA341
H
RB1
H
H
H
H
NCH3
LA342
H
RB2
H
H
H
H
NCH3
LA343
H
RB3
H
H
H
H
NCH3
LA344
H
RB4
H
H
H
H
NCH3
LA345
H
RB5
H
H
H
H
NCH3
LA346
H
RA2
H
H
H
H
NCH3
LA347
H
RA22
H
H
H
H
NCH3
LA348
H
RA28
H
H
H
H
NCH3
LA349
H
H
H
H
H
H
S
LA350
H
RB1
H
H
H
H
S
LA351
H
RB2
H
H
H
H
S
LA352
H
RB3
H
H
H
H
S
LA353
H
RB4
H
H
H
H
S
LA354
H
RB5
H
H
H
H
S
LA355
H
RA2
H
H
H
H
S
LA356
H
RA22
H
H
H
H
S
LA357
H
RA28
H
H
H
H
S
LA358
H
H
H
H
H
H
O
LA359
H
RB1
H
H
H
H
O
LA360
H
RB2
H
H
H
H
O
LA361
H
RB3
H
H
H
H
O
LA362
H
RB4
H
H
H
H
O
LA363
H
RB5
H
H
H
H
O
LA364
H
RA2
H
H
H
H
O
LA365
H
RA22
H
H
H
H
O
LA366
H
RA28
H
H
H
H
O
LA367
H
H
H
H
H
H
Si(CH3)2
LA368
H
RB1
H
H
H
H
Si(CH3)2
LA369
H
RB2
H
H
H
H
Si(CH3)2
LA370
H
RB3
H
H
H
H
Si(CH3)2
LA371
H
RB4
H
H
H
H
Si(CH3)2
LA372
H
RB5
H
H
H
H
Si(CH3)2
LA373
H
RA2
H
H
H
H
Si(CH3)2
LA374
H
RA22
H
H
H
H
Si(CH3)2
LA375
H
RA28
H
H
H
H
Si(CH3)2
LA376
H
H
RB1
H
H
H
C(CH3)2
LA377
H
H
RB2
H
H
H
C(CH3)2
LA378
H
H
RB3
H
H
H
C(CH3)2
LA379
H
H
RB4
H
H
H
C(CH3)2
LA380
H
H
RB5
H
H
H
C(CH3)2
LA381
H
H
RA2
H
H
H
C(CH3)2
LA382
H
H
RA22
H
H
H
C(CH3)2
LA383
H
H
RA28
H
H
H
C(CH3)2
LA384
H
H
RB1
H
H
H
NCH3
LA385
H
H
RB2
H
H
H
NCH3
LA386
H
H
RB3
H
H
H
NCH3
LA387
H
H
RB4
H
H
H
NCH3
LA388
H
H
RB5
H
H
H
NCH3
LA389
H
H
RA2
H
H
H
NCH3
LA390
H
H
RA22
H
H
H
NCH3
LA391
H
H
RA28
H
H
H
NCH3
LA392
H
H
RB1
H
H
H
S
LA393
H
H
RB2
H
H
H
S
LA394
H
H
RB3
H
H
H
S
LA395
H
H
RB4
H
H
H
S
LA396
H
H
RB5
H
H
H
S
LA397
H
H
RA2
H
H
H
S
LA398
H
H
RA22
H
H
H
S
LA399
H
H
RA28
H
H
H
S
LA400
H
H
RB1
H
H
H
O
LA401
H
H
RB2
H
H
H
O
LA402
H
H
RB3
H
H
H
O
LA403
H
H
RB4
H
H
H
O
LA404
H
H
RB5
H
H
H
O
LA405
H
H
RA2
H
H
H
O
LA406
H
H
RA22
H
H
H
O
LA407
H
H
RA28
H
H
H
O
LA408
H
H
RB1
H
H
H
Si(CH3)2
LA409
H
H
RB2
H
H
H
Si(CH3)2
LA410
H
H
RB3
H
H
H
Si(CH3)2
LA411
H
H
RB4
H
H
H
Si(CH3)2
LA412
H
H
RB5
H
H
H
Si(CH3)2
LA413
H
H
RA2
H
H
H
Si(CH3)2
LA414
H
H
RA22
H
H
H
Si(CH3)2
LA415
H
H
RA28
H
H
H
Si(CH3)2
LA416
H
H
H
RB1
H
H
C(CH3)2
LA417
H
H
H
RB2
H
H
C(CH3)2
LA418
H
H
H
RB3
H
H
C(CH3)2
LA419
H
H
H
RB4
H
H
C(CH3)2
LA420
H
H
H
RB5
H
H
C(CH3)2
LA421
H
H
H
RA2
H
H
C(CH3)2
LA422
H
H
H
RA22
H
H
C(CH3)2
LA423
H
H
H
RA28
H
H
C(CH3)2
LA424
H
H
H
RB1
H
H
NCH3
LA425
H
H
H
RB2
H
H
NCH3
LA426
H
H
H
RB3
H
H
NCH3
LA427
H
H
H
RB4
H
H
NCH3
LA428
H
H
H
RB5
H
H
NCH3
LA429
H
H
H
RA2
H
H
NCH3
LA430
H
H
H
RA22
H
H
NCH3
LA431
H
H
H
RA28
H
H
NCH3
LA432
H
H
H
RB1
H
H
S
LA433
H
H
H
RB2
H
H
S
LA434
H
H
H
RB3
H
H
S
LA435
H
H
H
RB4
H
H
S
LA436
H
H
H
RB5
H
H
S
LA437
H
H
H
RA2
H
H
S
LA438
H
H
H
RA22
H
H
S
LA439
H
H
H
RA28
H
H
S
LA440
H
H
H
RB1
H
H
O
LA441
H
H
H
RB2
H
H
O
LA442
H
H
H
RB3
H
H
O
LA443
H
H
H
RB4
H
H
O
LA444
H
H
H
RB5
H
H
O
LA445
H
H
H
RA2
H
H
O
LA446
H
H
H
RA22
H
H
O
LA447
H
H
H
RA28
H
H
O
LA448
H
H
H
RB1
H
H
Si(CH3)2
LA449
H
H
H
RB2
H
H
Si(CH3)2
LA450
H
H
H
RB3
H
H
Si(CH3)2
LA451
H
H
H
RB4
H
H
Si(CH3)2
LA452
H
H
H
RB5
H
H
Si(CH3)2
LA453
H
H
H
RA2
H
H
Si(CH3)2
LA454
H
H
H
RA22
H
H
Si(CH3)2
LA455
H
H
H
RA28
H
H
Si(CH3)2
LA581
H
H
H
H
H
CH3
C(CH3)2
LA582
H
RB1
H
H
H
CH3
C(CH3)2
LA583
H
RB2
H
H
H
CH3
C(CH3)2
LA584
H
RB3
H
H
H
CH3
C(CH3)2
LA585
H
RB4
H
H
H
CH3
C(CH3)2
LA586
H
RB5
H
H
H
CH3
C(CH3)2
LA587
H
RA2
H
H
H
CH3
C(CH3)2
LA588
H
RA22
H
H
H
CH3
C(CH3)2
LA589
H
RA28
H
H
H
CH3
C(CH3)2
LA590
H
H
H
H
H
CH3
NCH3
LA591
H
RB1
H
H
H
CH3
NCH3
LA592
H
RB2
H
H
H
CH3
NCH3
LA593
H
RB3
H
H
H
CH3
NCH3
LA594
H
RB4
H
H
H
CH3
NCH3
LA595
H
RB5
H
H
H
CH3
NCH3
LA596
H
RA2
H
H
H
CH3
NCH3
LA597
H
RA22
H
H
H
CH3
NCH3
LA598
H
RA28
H
H
H
CH3
NCH3
LA599
H
H
H
H
H
CH3
S
LA600
H
RB1
H
H
H
CH3
S
LA601
H
RB2
H
H
H
CH3
S
LA602
H
RB3
H
H
H
CH3
S
LA603
H
RB4
H
H
H
CH3
S
LA604
H
RB5
H
H
H
CH3
S
LA605
H
RA2
H
H
H
CH3
S
LA606
H
RA22
H
H
H
CH3
S
LA607
H
RA28
H
H
H
CH3
S
LA608
H
H
H
H
H
CH3
O
LA609
H
RB1
H
H
H
CH3
O
LA610
H
RB2
H
H
H
CH3
O
LA611
H
RB3
H
H
H
CH3
O
LA612
H
RB4
H
H
H
CH3
O
LA613
H
RB5
H
H
H
CH3
O
LA614
H
RA2
H
H
H
CH3
O
LA615
H
RA22
H
H
H
CH3
O
LA616
H
RA28
H
H
H
CH3
O
LA617
H
H
H
H
H
CH3
Si(CH3)2
LA618
H
RB1
H
H
H
CH3
Si(CH3)2
LA619
H
RB2
H
H
H
CH3
Si(CH3)2
LA620
H
RB3
H
H
H
CH3
Si(CH3)2
LA621
H
RB4
H
H
H
CH3
Si(CH3)2
LA622
H
RB5
H
H
H
CH3
Si(CH3)2
LA623
H
RA2
H
H
H
CH3
Si(CH3)2
LA624
H
RA22
H
H
H
CH3
Si(CH3)2
LA625
H
RA28
H
H
H
CH3
Si(CH3)2
LA626
H
H
RB1
H
H
CH3
C(CH3)2
LA627
H
H
RB2
H
H
CH3
C(CH3)2
LA628
H
H
RB3
H
H
CH3
C(CH3)2
LA629
H
H
RB4
H
H
CH3
C(CH3)2
LA630
H
H
RB5
H
H
CH3
C(CH3)2
LA631
H
H
RA2
H
H
CH3
C(CH3)2
LA632
H
H
RA22
H
H
CH3
C(CH3)2
LA633
H
H
RA28
H
H
CH3
C(CH3)2
LA634
H
H
RB1
H
H
CH3
NCH3
LA635
H
H
RB2
H
H
CH3
NCH3
LA636
H
H
RB3
H
H
CH3
NCH3
LA637
H
H
RB4
H
H
CH3
NCH3
LA638
H
H
RB5
H
H
CH3
NCH3
LA639
H
H
RA2
H
H
CH3
NCH3
LA640
H
H
RA22
H
H
CH3
NCH3
LA641
H
H
RA28
H
H
CH3
NCH3
LA642
H
H
RB1
H
H
CH3
S
LA643
H
H
RB2
H
H
CH3
S
LA644
H
H
RB3
H
H
CH3
S
LA645
H
H
RB4
H
H
CH3
S
LA646
H
H
RB5
H
H
CH3
S
LA647
H
H
RA2
H
H
CH3
S
LA648
H
H
RA22
H
H
CH3
S
LA649
H
H
RA28
H
H
CH3
S
LA650
H
H
RB1
H
H
CH3
O
LA651
H
H
RB2
H
H
CH3
O
LA652
H
H
RB3
H
H
CH3
O
LA653
H
H
RB4
H
H
CH3
O
LA654
H
H
RB5
H
H
CH3
O
LA655
H
H
RA2
H
H
CH3
O
LA656
H
H
RA22
H
H
CH3
O
LA657
H
H
RA28
H
H
CH3
O
LA658
H
H
RB1
H
H
CH3
Si(CH3)2
LA659
H
H
RB2
H
H
CH3
Si(CH3)2
LA660
H
H
RB3
H
H
CH3
Si(CH3)2
LA661
H
H
RB4
H
H
CH3
Si(CH3)2
LA662
H
H
RB5
H
H
CH3
Si(CH3)2
LA663
H
H
RA2
H
H
CH3
Si(CH3)2
LA664
H
H
RA22
H
H
CH3
Si(CH3)2
LA665
H
H
RA28
H
H
CH3
Si(CH3)2
LA666
H
H
H
RB1
H
CH3
C(CH3)2
LA667
H
H
H
RB2
H
CH3
C(CH3)2
LA668
H
H
H
RB3
H
CH3
C(CH3)2
LA669
H
H
H
RB4
H
CH3
C(CH3)2
LA670
H
H
H
RB5
H
CH3
C(CH3)2
LA671
H
H
H
RA2
H
CH3
C(CH3)2
LA672
H
H
H
RA22
H
CH3
C(CH3)2
LA673
H
H
H
RA28
H
CH3
C(CH3)2
LA674
H
H
H
RB1
H
CH3
NCH3
LA675
H
H
H
RB2
H
CH3
NCH3
LA676
H
H
H
RB3
H
CH3
NCH3
LA677
H
H
H
RB4
H
CH3
NCH3
LA678
H
H
H
RB5
H
CH3
NCH3
LA679
H
H
H
RA2
H
CH3
NCH3
LA680
H
H
H
RA22
H
CH3
NCH3
LA681
H
H
H
RA28
H
CH3
NCH3
LA682
H
H
H
RB1
H
CH3
S
LA683
H
H
H
RB2
H
CH3
S
LA684
H
H
H
RB3
H
CH3
S
LA685
H
H
H
RB4
H
CH3
S
LA686
H
H
H
RB5
H
CH3
S
LA687
H
H
H
RA2
H
CH3
S
LA688
H
H
H
RA22
H
CH3
S
LA689
H
H
H
RA28
H
CH3
S
LA690
H
H
H
RB1
H
CH3
O
LA691
H
H
H
RB2
H
CH3
O
LA692
H
H
H
RB3
H
CH3
O
LA693
H
H
H
RB4
H
CH3
O
LA694
H
H
H
RB5
H
CH3
O
LA695
H
H
H
RA2
H
CH3
O
LA696
H
H
H
RA22
H
CH3
O
LA697
H
H
H
RA28
H
CH3
O
LA698
H
H
H
RB1
H
CH3
Si(CH3)2
LA699
H
H
H
RB2
H
CH3
Si(CH3)2
LA700
H
H
H
RB3
H
CH3
Si(CH3)2
LA701
H
H
H
RB4
H
CH3
Si(CH3)2
LA702
H
H
H
RB5
H
CH3
Si(CH3)2
LA703
H
H
H
RA2
H
CH3
Si(CH3)2
LA704
H
H
H
RA22
H
CH3
Si(CH3)2
LA705
H
H
H
RA28
H
CH3
Si(CH3)2
LA1331 to LA1455 and LA1581 to LA1705 based on the following formula:
RA
RB
RC
RE
RF
RG
Y
LA1331
H
H
H
H
H
H
C(CH3)2
LA1332
H
RB1
H
H
H
H
C(CH3)2
LA1333
H
RB2
H
H
H
H
C(CH3)2
LA1334
H
RB3
H
H
H
H
C(CH3)2
LA1335
H
RB4
H
H
H
H
C(CH3)2
LA1336
H
RB5
H
H
H
H
C(CH3)2
LA1337
H
RA2
H
H
H
H
C(CH3)2
LA1338
H
RA22
H
H
H
H
C(CH3)2
LA1339
H
RA28
H
H
H
H
C(CH3)2
LA1340
H
H
H
H
H
H
NCH3
LA1341
H
RB1
H
H
H
H
NCH3
LA1342
H
RB2
H
H
H
H
NCH3
LA1343
H
RB3
H
H
H
H
NCH3
LA1344
H
RB4
H
H
H
H
NCH3
LA1345
H
RB5
H
H
H
H
NCH3
LA1346
H
RA2
H
H
H
H
NCH3
LA1347
H
RA22
H
H
H
H
NCH3
LA1348
H
RA28
H
H
H
H
NCH3
LA1349
H
H
H
H
H
H
S
LA1350
H
RB1
H
H
H
H
S
LA1351
H
RB2
H
H
H
H
S
LA1352
H
RB3
H
H
H
H
S
LA1353
H
RB4
H
H
H
H
S
LA1354
H
RB5
H
H
H
H
S
LA1355
H
RA2
H
H
H
H
S
LA1356
H
RA22
H
H
H
H
S
LA1357
H
RA28
H
H
H
H
S
LA1358
H
H
H
H
H
H
O
LA1359
H
RB1
H
H
H
H
O
LA1360
H
RB2
H
H
H
H
O
LA1361
H
RB3
H
H
H
H
O
LA1362
H
RB4
H
H
H
H
O
LA1363
H
RB5
H
H
H
H
O
LA1364
H
RA2
H
H
H
H
O
LA1365
H
RA22
H
H
H
H
O
LA1366
H
RA28
H
H
H
H
O
LA1367
H
H
H
H
H
H
Si(CH3)2
LA1368
H
RB1
H
H
H
H
Si(CH3)2
LA1369
H
RB2
H
H
H
H
Si(CH3)2
LA1370
H
RB3
H
H
H
H
Si(CH3)2
LA1371
H
RB4
H
H
H
H
Si(CH3)2
LA1372
H
RB5
H
H
H
H
Si(CH3)2
LA1373
H
RA2
H
H
H
H
Si(CH3)2
LA1374
H
RA22
H
H
H
H
Si(CH3)2
LA1375
H
RA28
H
H
H
H
Si(CH3)2
LA1376
H
H
RB1
H
H
H
C(CH3)2
LA1377
H
H
RB2
H
H
H
C(CH3)2
LA1378
H
H
RB3
H
H
H
C(CH3)2
LA1379
H
H
RB4
H
H
H
C(CH3)2
LA1380
H
H
RB5
H
H
H
C(CH3)2
LA1381
H
H
RA2
H
H
H
C(CH3)2
LA1382
H
H
RA22
H
H
H
C(CH3)2
LA1383
H
H
RA28
H
H
H
C(CH3)2
LA1384
H
H
RB1
H
H
H
NCH3
LA1385
H
H
RB2
H
H
H
NCH3
LA1386
H
H
RB3
H
H
H
NCH3
LA1387
H
H
RB4
H
H
H
NCH3
LA1388
H
H
RB5
H
H
H
NCH3
LA1389
H
H
RA2
H
H
H
NCH3
LA1390
H
H
RA22
H
H
H
NCH3
LA1391
H
H
RA28
H
H
H
NCH3
LA1392
H
H
RB1
H
H
H
S
LA1393
H
H
RB2
H
H
H
S
LA1394
H
H
RB3
H
H
H
S
LA1395
H
H
RB4
H
H
H
S
LA1396
H
H
RB5
H
H
H
S
LA1397
H
H
RA2
H
H
H
S
LA1398
H
H
RA22
H
H
H
S
LA1399
H
H
RA28
H
H
H
S
LA1400
H
H
RB1
H
H
H
O
LA1401
H
H
RB2
H
H
H
O
LA1402
H
H
RB3
H
H
H
O
LA1403
H
H
RB4
H
H
H
O
LA1404
H
H
RB5
H
H
H
O
LA1405
H
H
RA2
H
H
H
O
LA1406
H
H
RA22
H
H
H
O
LA1407
H
H
RA28
H
H
H
O
LA1408
H
H
RB1
H
H
H
Si(CH3)2
LA1409
H
H
RB2
H
H
H
Si(CH3)2
LA1410
H
H
RB3
H
H
H
Si(CH3)2
LA1411
H
H
RB4
H
H
H
Si(CH3)2
LA1412
H
H
RB5
H
H
H
Si(CH3)2
LA1413
H
H
RA2
H
H
H
Si(CH3)2
LA1414
H
H
RA22
H
H
H
Si(CH3)2
LA1415
H
H
RA28
H
H
H
Si(CH3)2
LA1416
H
H
H
RB1
H
H
C(CH3)2
LA1417
H
H
H
RB2
H
H
C(CH3)2
LA1418
H
H
H
RB3
H
H
C(CH3)2
LA1419
H
H
H
RB4
H
H
C(CH3)2
LA1420
H
H
H
RB5
H
H
C(CH3)2
LA1421
H
H
H
RA2
H
H
C(CH3)2
LA1422
H
H
H
RA22
H
H
C(CH3)2
LA1423
H
H
H
RA28
H
H
C(CH3)2
LA1424
H
H
H
RB1
H
H
NCH3
LA1425
H
H
H
RB2
H
H
NCH3
LA1426
H
H
H
RB3
H
H
NCH3
LA1427
H
H
H
RB4
H
H
NCH3
LA1428
H
H
H
RB5
H
H
NCH3
LA1429
H
H
H
RA2
H
H
NCH3
LA1430
H
H
H
RA22
H
H
NCH3
LA1431
H
H
H
RA28
H
H
NCH3
LA1432
H
H
H
RB1
H
H
S
LA1433
H
H
H
RB2
H
H
S
LA1434
H
H
H
RB3
H
H
S
LA1435
H
H
H
RB4
H
H
S
LA1436
H
H
H
RB5
H
H
S
LA1437
H
H
H
RA2
H
H
S
LA1438
H
H
H
RA22
H
H
S
LA1439
H
H
H
RA28
H
H
S
LA1440
H
H
H
RB1
H
H
O
LA1441
H
H
H
RB2
H
H
O
LA1442
H
H
H
RB3
H
H
O
LA1443
H
H
H
RB4
H
H
O
LA1444
H
H
H
RB5
H
H
O
LA1445
H
H
H
RA2
H
H
O
LA1446
H
H
H
RA22
H
H
O
LA1447
H
H
H
RA28
H
H
O
LA1448
H
H
H
RB1
H
H
Si(CH3)2
LA1449
H
H
H
RB2
H
H
Si(CH3)2
LA1450
H
H
H
RB3
H
H
Si(CH3)2
LA1451
H
H
H
RB4
H
H
Si(CH3)2
LA1452
H
H
H
RB5
H
H
Si(CH3)2
LA1453
H
H
H
RA2
H
H
Si(CH3)2
LA1454
H
H
H
RA22
H
H
Si(CH3)2
LA1455
H
H
H
RA28
H
H
Si(CH3)2
LA1581
H
H
H
H
H
CH3
C(CH3)2
LA1582
H
RB1
H
H
H
CH3
C(CH3)2
LA1583
H
RB2
H
H
H
CH3
C(CH3)2
LA1584
H
RB3
H
H
H
CH3
C(CH3)2
LA1585
H
RB4
H
H
H
CH3
C(CH3)2
LA1586
H
RB5
H
H
H
CH3
C(CH3)2
LA1587
H
RA2
H
H
H
CH3
C(CH3)2
LA1588
H
RA22
H
H
H
CH3
C(CH3)2
LA1589
H
RA28
H
H
H
CH3
C(CH3)2
LA1590
H
H
H
H
H
CH3
NCH3
LA1591
H
RB1
H
H
H
CH3
NCH3
LA1592
H
RB2
H
H
H
CH3
NCH3
LA1593
H
RB3
H
H
H
CH3
NCH3
LA1594
H
RB4
H
H
H
CH3
NCH3
LA1595
H
RB5
H
H
H
CH3
NCH3
LA1596
H
RA2
H
H
H
CH3
NCH3
LA1597
H
RA22
H
H
H
CH3
NCH3
LA1598
H
RA28
H
H
H
CH3
NCH3
LA1599
H
H
H
H
H
CH3
S
LA1600
H
RB1
H
H
H
CH3
S
LA1601
H
RB2
H
H
H
CH3
S
LA1602
H
RB3
H
H
H
CH3
S
LA1603
H
RB4
H
H
H
CH3
S
LA1604
H
RB5
H
H
H
CH3
S
LA1605
H
RA2
H
H
H
CH3
S
LA1606
H
RA22
H
H
H
CH3
S
LA1607
H
RA28
H
H
H
CH3
S
LA1608
H
H
H
H
H
CH3
O
LA1609
H
RB1
H
H
H
CH3
O
LA1610
H
RB2
H
H
H
CH3
O
LA1611
H
RB3
H
H
H
CH3
O
LA1612
H
RB4
H
H
H
CH3
O
LA1613
H
RB5
H
H
H
CH3
O
LA1614
H
RA2
H
H
H
CH3
O
LA1615
H
RA22
H
H
H
CH3
O
LA1616
H
RA28
H
H
H
CH3
O
LA1617
H
H
H
H
H
CH3
Si(CH3)2
LA1618
H
RB1
H
H
H
CH3
Si(CH3)2
LA1619
H
RB2
H
H
H
CH3
Si(CH3)2
LA1620
H
RB3
H
H
H
CH3
Si(CH3)2
LA1621
H
RB4
H
H
H
CH3
Si(CH3)2
LA1622
H
RB5
H
H
H
CH3
Si(CH3)2
LA1623
H
RA2
H
H
H
CH3
Si(CH3)2
LA1624
H
RA22
H
H
H
CH3
Si(CH3)2
LA1625
H
RA28
H
H
H
CH3
Si(CH3)2
LA1626
H
H
RB1
H
H
CH3
C(CH3)2
LA1627
H
H
RB2
H
H
CH3
C(CH3)2
LA1628
H
H
RB3
H
H
CH3
C(CH3)2
LA1629
H
H
RB4
H
H
CH3
C(CH3)2
LA1630
H
H
RB5
H
H
CH3
C(CH3)2
LA1631
H
H
RA2
H
H
CH3
C(CH3)2
LA1632
H
H
RA22
H
H
CH3
C(CH3)2
LA1633
H
H
RA28
H
H
CH3
C(CH3)2
LA1634
H
H
RB1
H
H
CH3
NCH3
LA1635
H
H
RB2
H
H
CH3
NCH3
LA1636
H
H
RB3
H
H
CH3
NCH3
LA1637
H
H
RB4
H
H
CH3
NCH3
LA1638
H
H
RB5
H
H
CH3
NCH3
LA1639
H
H
RA2
H
H
CH3
NCH3
LA1640
H
H
RA22
H
H
CH3
NCH3
LA1641
H
H
RA28
H
H
CH3
NCH3
LA1642
H
H
RB1
H
H
CH3
NCH3
LA1643
H
H
RB2
H
H
CH3
S
LA1644
H
H
RB3
H
H
CH3
S
LA1645
H
H
RB4
H
H
CH3
S
LA1646
H
H
RB5
H
H
CH3
S
LA1647
H
H
RA2
H
H
CH3
S
LA1648
H
H
RA22
H
H
CH3
S
LA1649
H
H
RA28
H
H
CH3
S
LA1650
H
H
RB1
H
H
CH3
O
LA1651
H
H
RB2
H
H
CH3
O
LA1652
H
H
RB3
H
H
CH3
O
LA1653
H
H
RB4
H
H
CH3
O
LA1654
H
H
RB5
H
H
CH3
O
LA1655
H
H
RA2
H
H
CH3
O
LA1656
H
H
RA22
H
H
CH3
O
LA1657
H
H
RA28
H
H
CH3
O
LA1658
H
H
RB1
H
H
CH3
Si(CH3)2
LA1659
H
H
RB2
H
H
CH3
Si(CH3)2
LA1660
H
H
RB3
H
H
CH3
Si(CH3)2
LA1661
H
H
RB4
H
H
CH3
Si(CH3)2
LA1662
H
H
RB5
H
H
CH3
Si(CH3)2
LA1663
H
H
RA2
H
H
CH3
Si(CH3)2
LA1664
H
H
RA22
H
H
CH3
Si(CH3)2
LA1665
H
H
RA28
H
H
CH3
Si(CH3)2
LA1666
H
H
H
RB1
H
CH3
C(CH3)2
LA1667
H
H
H
RB2
H
CH3
C(CH3)2
LA1668
H
H
H
RB3
H
CH3
C(CH3)2
LA1669
H
H
H
RB4
H
CH3
C(CH3)2
LA1670
H
H
H
RB5
H
CH3
C(CH3)2
LA1671
H
H
H
RA2
H
CH3
C(CH3)2
LA1672
H
H
H
RA22
H
CH3
C(CH3)2
LA1673
H
H
H
RA28
H
CH3
C(CH3)2
LA1674
H
H
H
RB1
H
CH3
NCH3
LA1675
H
H
H
RB2
H
CH3
NCH3
LA1676
H
H
H
RB3
H
CH3
NCH3
LA1677
H
H
H
RB4
H
CH3
NCH3
LA1678
H
H
H
RB5
H
CH3
NCH3
LA1679
H
H
H
RA2
H
CH3
NCH3
LA1680
H
H
H
RA22
H
CH3
NCH3
LA1681
H
H
H
RA28
H
CH3
NCH3
LA1682
H
H
H
RB1
H
CH3
S
LA1683
H
H
H
RB2
H
CH3
S
LA1684
H
H
H
RB3
H
CH3
S
LA1685
H
H
H
RB4
H
CH3
S
LA1686
H
H
H
RB5
H
CH3
S
LA1687
H
H
H
RA2
H
CH3
S
LA1688
H
H
H
RA22
H
CH3
S
LA1689
H
H
H
RA28
H
CH3
S
LA1690
H
H
H
RB1
H
CH3
O
LA1691
H
H
H
RB2
H
CH3
O
LA1692
H
H
H
RB3
H
CH3
O
LA1693
H
H
H
RB4
H
CH3
O
LA1694
H
H
H
RB5
H
CH3
O
LA1695
H
H
H
RA2
H
CH3
O
LA1696
H
H
H
RA22
H
CH3
O
LA1697
H
H
H
RA28
H
CH3
O
LA1698
H
H
H
RB1
H
CH3
Si(CH3)2
LA1699
H
H
H
RB2
H
CH3
Si(CH3)2
LA1700
H
H
H
RB3
H
CH3
Si(CH3)2
LA1701
H
H
H
RB4
H
CH3
Si(CH3)2
LA1702
H
H
H
RB5
H
CH3
Si(CH3)2
LA1703
H
H
H
RA2
H
CH3
Si(CH3)2
LA1704
H
H
H
RA22
H
CH3
Si(CH3)2
LA1705
H
H
H
RA28
H
CH3
Si(CH3)2
wherein RA2, RA22, and RA28 have the following structures:
and
wherein RB1 to RB5 have the following structures:

### Claim 11 (depends on 1)

The compound of claim 1, wherein ligand LB is selected from the group consisting of:
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, Ra, Rb, Rc, and Rd are each 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 two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 10)

The compound of claim 10, wherein the compound is Compound x having the formula M(LAi)2(LCj);
wherein x=13(i−1)+j, i is an integer from 1 to 830 or 1331 to 1830, and j is an integer from 1 to 13; and
wherein LCj has one of the following formula:

### Claim 15

An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of 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, 2, or 3;
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 X1, X2, X3, X4, X5, and X6 are each independently a CR or N;
wherein X7 is CH;
wherein X8 is carbon or nitrogen;
wherein when X6 is a CR, R is hydrogen;
wherein Y is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RCC, and RDD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R″, RCC, and RDD 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;
wherein each of RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein each of RX, RY, and RZ do not comprise alkenyl;
wherein when X1 to X5 is carbon, then R1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof; and when R1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein when at least one of X1 to X5 is nitrogen, then R1 is 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 R1, R, R′, R″, RCC, RDD, RX, RY, and RZ are optionally joined or fused into a ring.

### Claim 16 (depends on 15)

The OLED of claim 15, wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

### Claim 17 (depends on 15)

The OLED of claim 15, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

### Claim 18 (depends on 15)

The OLED of claim 15, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 19

A formulation comprising a compound of 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, 2, or 3;
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 X1, X2, X3, X4, X5, and X6 are each independently a CR or N;
wherein X7 is CH;
wherein X8 is carbon or nitrogen;
wherein when X6 is a CR, R is hydrogen;
wherein Y is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RCC, and RDD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
wherein each of R, R′, R″, RCC, and RDD 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;
wherein each of RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein each of RX, RY, and RZ do not comprise alkenyl;
wherein when X1 to X5 is carbon, then R1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof; and when R1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein when at least one of X1 to X5 is nitrogen, then R1 is 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 R1, R, R′, R″, RCC, RDD, RX, RY, and RZ are optionally joined or fused into a ring.

### Claim 20 (depends on 1)

A compound of claim 1, wherein the ligand LB is selected from the group consisting of:
wherein in ligand LB:
X1 to X13 are each independently selected from the group consisting of carbon and nitrogen;
Ra, Rb, Rc, and Rd may each represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein any adjacent substituents of Ra, Rb, Rc, Rd, do not join or fuse to form a ring;
wherein x is 1 or 2;
wherein y is 1 or 2;
wherein z is 0 or 1; and
wherein each of Ra, Rb, Rc, Rd, 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.