IP Library › Granted Patent US 11,832,507

Granted Patent B2

US 11,832,507 · App. 17/325,829 · Granted Nov 28, 2023

Organic electroluminescent materials and devices

Inventors: Pierre-Luc T. Boudreault (Pennington, NJ); Harvey Wendt (Medford Lakes, NJ); Chuanjun Xia (Lawrenceville, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/342 C07F15/0033 C09K11/025 C09K11/06 H10K85/657 H10K85/6572 H10K85/6576 C09K2211/1029 C09K2211/1059 C09K2211/1088 C09K2211/185 H10K50/11 H10K2101/10

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Quick Facts

Patent No.: US 11,832,507
App. No.: 17/325,829
Granted: Nov 28, 2023
Kind: B2

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Abstract

A compound having a formula M(L A ) x (L B ) y (L C ) z , where ligand L A is ligand L B is and ligand L C is is disclosed. In formula M(L A ) x (L B ) y (L C ) 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; A 1 -A 8 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 NR 1 ; rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; at least one R 4 is a five-membered or six-membered heterocyclic ring which can be further substituted by R E ; each R substituent is independently selected from the several substituents; and any adjacent R substitutents are optionally joined to form a ring.

Claims (601)

1. A compound having a formula M(L A ) x (L B ) y (L C ) z :

wherein the ligand L A is

wherein the ligand L B is

wherein the ligand L C is

wherein the compound is heteroleptic;

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 A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 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 NR 1 ;

wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R 3 represents mono, or di-substitution, or no substitution;

wherein R 2 , R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution;

wherein R 4 represents mono, di, tri, or tetra-substitution;

wherein at least one R 4 is a five-membered or six-membered heterocyclic ring which can be further substituted by R E ;

wherein R E represents mono, di, tri, or tetra-substitution, or no substitution;

wherein each of R, R′, R 1 , R 2 , R 3 , R 4 , R C , R D , R X , R Y , R Z and R E 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 any adjacent substitutents of R, R′, R 1 , R 2 , R 3 , R 4 , R C , R D , R X , R Y , R Z and R E are optionally joined to form a ring; and

wherein at least one of the following is true:

(i) x is 1, y is 1, and z is 1;

(ii) y is 1 or 2, X is CRR′ or NR 1 , and (a) each R E is hydrogen, or (b) each R E that is not hydrogen, does not comprise aryl or heteroaryl; or

(iii) z is 1 or 2, and at least one of A 1 to A 8 is N.

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

3. The compound of claim 1 , wherein the compound has the formula M(L A ) 2 (L C ) or the formula M(L A )(L B ) 2 .

4. The compound of claim 1 , wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 are carbon.

5. The compound of claim 1 , wherein X is CRR′ or NR 1 .

6. The compound of claim 1 , wherein at least one R 4 is a five-membered or six-membered aromatic heterocyclic ring.

7. The compound of claim 1 , wherein at least one R 4 is a six-membered aromatic heterocyclic ring where the only heteroatom is nitrogen.

8. The compound of claim 1 , wherein at least one R 4 is pyridine, triazine, pyrazine, pyrimidine, or pyridazine.

9. The compound of claim 1 , wherein z is 1 or 2 and L C has the formula:

wherein R 5 , R 6 , R 7 , and R 8 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

wherein at least one of R 5 , R 6 , R 7 , or R 8 has at least two C atoms.

10. The compound of claim 1 , wherein each of R, R′, R 1 , R 2 , R 3 , R 4 , R C , R D , R X , R Y , R Z and R E is independently selected from group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and combinations thereof.

11. The compound of claim 1 , wherein y is 1 or 2, ring C is benzene, and ring D is pyridine.

12. The compound of claim 1 , wherein L A is selected from the group consisting of:

13. The compound of claim 1 , wherein L A is selected from the group consisting of:

L A1 through L A8 , each represented by the formula:

wherein in L A1 : R 1 = R A1 and R 2 = R B1 ,

in L A2 : R 1 = R A2 and R 2 = R B1 ,

in L A3 : R 1 = R A3 , R 2 = R B1 ,

in L A4 : R 1 = R A4 , R 2 = R B1 ,

in L A5 : R 1 = R A1 , R 2 = R B2 ,

in L A6 : R 1 = R A2 , R 2 = R B2 ,

in L A7 : R 1 = R A3 , R 2 = R B2 , and

in L A8 : R 1 = R A4 , R 2 = R B2 ,

L A9 through L A16 , each represented by the formula:

wherein in L A9 : R 1 = R A1 , R 2 = R B1 ,

in L A10 : R 1 = R A2 , R 2 = R B1 ,

in L A11 : R 1 = R A3 , R 2 = R B1 ,

in L A12 : R 1 = R A4 , R 2 = R B1 ,

in L A13 : R 1 = R A1 , R 2 = R B2 ,

in L A14 : R 1 = R A2 , R 2 = R B2 ,

in L A15 : R 1 = R A3 , R 2 = R B2 , and

in L A16 : R 1 = R A4 , R 2 = R B2 ,

L A17 through L A24 , each represented by the formula:

wherein L A17 : R 1 = R A1 , R 2 = R B1 ,

in L A18 : R 1 = R A2 , R 2 = R B1 ,

in L A19 : R 1 = R A3 , R 2 = R B1 ,

in L A20 : R 1 = R A4 , R 2 = R B1 ,

in L A21 : R 1 = R A1 , R 2 = R B2 ,

in L A22 : R 1 = R A2 , R 2 = R B2 ,

in L A23 : R 1 = R A3 , R 2 = R B2 , and

in L A24 : R 1 = R A4 , R 2 = R B2 ,

L A25 through L A32 , each represented by the formula:

wherein in L A25 : R 1 = R A1 , R 2 = R B1 ,

in L A26 : R 1 = R A2 , R 2 = R B1 ,

in L A27 : R 1 = R A3 , R 2 = R B1 ,

in L A28 : R 1 = R A4 , R 2 = R B1 ,

in L A29 : R 1 = R A1 , R 2 = R B2 ,

in L A30 : R 1 = R A2 , R 2 = R B2 ,

in L A31 : R 1 = R A3 , R 2 = R B2 , and

in L A32 : R 1 = R A4 , R 2 = R B2 ,

L A33 through L A40 , each represented by the formula:

wherein in L A33 : R 1 = R A1 , R 2 = R B1 ,

in L A34 : R 1 = R A2 , R 2 = R B1 ,

in L A35 : R 1 = R A3 , R 2 = R B1 ,

in L A36 : R 1 = R A4 , R 2 = R B1 ,

in L A37 : R 1 = R A1 , R 2 = R B2 ,

in L A38 : R 1 = R A2 , R 2 = R B2 ,

in L A39 : R 1 = R A3 , R 2 = R B2 , and

in L A40 : R 1 = R A4 , R 2 = R B2 ,

L A41 through L A48 , each represented by the formula:

where in L A41 : R 1 = R A1 , R 2 = R B1 ,

in L A42 : R 1 = R A2 , R 2 = R B1 ,

in L A43 : R 1 = R A3 , R 2 = R B1 ,

in L A44 : R 1 = R A4 , R 2 = R B1 ,

in L A45 : R 1 = R A1 , R 2 = R B2 ,

in L A46 : R 1 = R A2 , R 2 = R B2 ,

in L A47 : R 1 = R A3 , R 2 = R B2 , and

in L A48 : R 1 = R A4 , R 2 = R B2 ,

L A49 through L A56 , each represented by the formula:

wherein in L A49 : R 1 = R A1 , R 2 = R B1 ,

in L A50 : R 1 = R A2 , R 2 = R B1 ,

in L A51 : R 1 = R A3 , R 2 = R B1 ,

in L A52 : R 1 = R A4 , R 2 = R B1 ,

in L A53 : R 1 = R A1 , R 2 = R B2 ,

in L A54 : R 1 = R A2 , R 2 = R B2 ,

in L A55 : R 1 = R A3 , R 2 = R B2 , and

in L A56 : R 1 = R A4 , R 2 = R B2 ,

L A57 through L A64 , each represented by the formula:

where in L A57 : R 1 = R A1 , R 2 = R B1 ,

in L A58 : R 1 = R A2 , R 2 = R B1 ,

in L A59 : R 1 = R A3 , R 2 = R B1 ,

in L A60 : R 1 = R A4 , R 2 = R B1 ,

in L A61 : R 1 = R A1 , R 2 = R B2 ,

in L A62 : R 1 = R A2 , R 2 = R B2 ,

in L A63 : R 1 = R A3 , R 2 = R B2 , and

in L A64 : R 1 = R A4 , R 2 = R B2 ,

L A65 through L A72 , each represented by the formula:

wherein in L A65 : R 1 = R A1 , R 2 = R B1 ,

in L A66 : R 1 = R A2 , R 2 = R B1 ,

in L A67 : R 1 = R A3 , R 2 = R B1 ,

in L A68 : R 1 = R A4, R 2 = R B1 ,

in L A69 : R 1 = R A1 , R 2 = R B2 ,

in L A70 : R 1 = R A2 , R 2 = R B2 ,

in L A71 : R 1 = R A3 , R 2 = R B2 , and

in L A72 : R 1 = R A4 , R 2 = R B2 ,

L A73 through L A80 , each represented by the formula:

wherein in L A73 : R 1 = R A1 , R 2 = R B1 ,

in L A74 : R 1 = R A2 , R 2 = R B1 ,

in L A75 : R 1 = R A3 , R 2 = R B1 ,

in L A76 : R 1 = R A4 , R 2 = R B1 ,

in L A77 : R 1 = R A1 , R 2 = R B2 ,

in L A78 : R 1 = R A2 , R 2 = R B2 ,

in L A79 : R 1 = R A3 , R 2 = R B2 , and

in L A80 : R 1 = R A4 , R 2 = R B2 ,

L A81 through L A88 , each represented by the formula:

wherein in L A81 : R 1 = R A1 , R 2 = R B1 ,

in L A82 : R 1 = R A2 , R 2 = R B1 ,

in L A83 : R 1 = R A3 , R 2 = R B1 ,

in L A84 : R 1 = R A4 , R 2 = R B1 ,

in L A85 : R 1 = R A1 , R 2 = R B2 ,

in L A86 : R 1 = R A2 , R 2 = R B2

in L A87 : R 1 = R A3 , R 2 = R B2 , and

in L A88 : R 1 = R A4 , R 2 = R B2 ,

L A89 through L A96 , each represented by the formula:

wherein in L A89 : R 1 = R A1 , R 2 = R B1 ,

in L A90 : R 1 = R A2 , R 2 = R B1 ,

in L A91 : R 1 = R A3 , R 2 = R B1 ,

in L A92 : R 1 = R A4 , R 2 = R B1 ,

in L A93 : R 1 = R A1 , R 2 = R B2 ,

in L A94 : R 1 = R A2 , R 2 = R B2 ,

in L A95 : R 1 = R A3 , R 2 = R B2 , and

in L A96 : R 1 = R A4, R 2 = R B2 ,

L A109 through L A110 , each represented by the formula:

wherein

in L A109 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A110 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A115 through L A116 , each represented by the formula:

wherein

in L A115 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A116 : X = C(CH 3 ) 2 , R 2 = R B2

L A121 through L A122 , each represented by the formula:

wherein

in L A121 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A122 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A127 through L A128 , each represented by the formula:

wherein

in L A127 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A128 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A133 through L A134 , each represented by the formula:

wherein

in L A133 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A134 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A139 through L A140 , each represented by the formula:

wherein

in L A139 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A140 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A145 through L A146 , each represented by the formula:

wherein

in L A145 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A146 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A151 through L A152 , each represented by the formula:

wherein

in L A151 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A152 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A157 through L A158 , each represented by the formula:

wherein

in L A157 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A158 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A163 through L A164 , each represented by the formula:

wherein

in L A163 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A164 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A169 through L A170 , each represented by the formula:

wherein

in L A169 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A170 : X = C(CH 3 ) 2 , R 2 = R B2 ,

L A171 through L A176 , each represented by the formula:

wherein in L A171 : X = O, R 2 = R B1 ,

in L A172 : X = O, R 2 = R B2 ,

in L A173 : X = S, R 2 = R B1 ,

in L A174 : X = S, R 2 = R B2 ,

in L A175 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A176 : X = C(CH3) 2 , R 2 = R B2 .

L A177 through L A182 each represented by the formula:

wherein in L A177 : X = O, R 2 = R B1 ,

in L A178 : X = O, R 2 = R B2 ,

in L A179 : X = S, R 2 = R B1 ,

in L A180 : X = S, R 2 = R B2 ,

in L A181 : X = C(CH 3 ) 2 , R 2 = R B1 , and

in L A182 : X = C(CH 3 ) 2 , R 2 = R B2 ; and

wherein R A1 to R A4 have the following structures:

R A1 , R A2 , R A3 , and R A4 , and

wherein R B1 and R B2 have the following structures:

R B1 , and R B2 ; and

wherein L A215 through L A230 , each represented

by the formula:

wherein in L A215 : X = O, R E = R A5 , R 2 = R B1 ,

in L A216 : X = O, R E = R A5 , R 2 = R B2 ,

in L A217 : X = O, R E = R A6 , R 2 = R B1 ,

in L A218 : X = O, R E = R A6 , R 2 = R B2 ,

in L A219 : X = O, R E = R A7 , R 2 = R B1 ,

in L A220 : X = O, R E = R A7 , R 2 = R B2 ,

in L A221 : X = O, R E = R A8 , R 2 = R B1 ,

in L A222 : X = O, R E = R A8 , R 2 = R B2 ,

in L A223 : X = S, R E = R A5 , R 2 = R B1 ,

in L A224 : X = S, R E = R A5 , R 2 = R B2 ,

in L A225 : X = S, R E = R A6 , R 2 = R B1 ,

in L A226 : X = S, R E = R A6 , R 2 = R B2 ,

in L A227 : X = S, R E = R A7 , R 2 = R B1 ,

in L A228 : X = S, R E = R A7 , R 2 = R B2 ,

in L A229 : X = S, R E = R A8 , R 2 = R B1 , and

in L A230 : X = S, R E = R A8 , R 2 = R B2 .

L A231 through L A246 , each represented by the formula:

wherein in L A231 : X = O, R E = R A5 , R 2 = R B1 ,

in L A232 : X = O, R E = R A5 , R 2 = R B2 ,

in L A233 : X = O, R E = R A6 , R 2 = R B1 ,

in L A234 : X = O, R E = R A6 , R 2 = R B2 ,

in L A235 : X = O, R E = R A7 , R 2 = R B1 ,

in L A236 : X = O, R E = R A7 , R 2 = R B2 ,

in L A237 : X = O, R E = R A8 , R 2 = R B1 ,

in L A238 : X = O, R E = R A8 , R 2 = R B2 ,

in L A239 : X = S, R E = R A5 , R 2 = R B1 ,

in L A240 : X = S, R E = R A5 , R 2 = R B2 ,

in L A241 : X = S, R E = R A6 , R 2 = R B1 ,

in L A242 : X = S, R E = R A6 , R 2 = R B2 ,

in L A243 : X = S, R E = R A7 , R 2 = R B1 ,

in L A244 : X = S, R E = R A7 , R 2 = R B2 ,

in L A245 : X = S, R E = R A8 , R 2 = R B1 , and

in L A246 : X = S, R E = R A8 , R 2 = R B2 .

L A279 through L A294 , each represented by the formula:

wherein in L A279 : X = O, R E = R A5 , R 2 = R B1 ,

in L A280 : X = O, R E = R A5 , R 2 = R B2 ,

in L A281 : X = O, R E = R A6 , R 2 = R B1 ,

in L A282 : X = O, R E = R A6 , R 2 = R B2 ,

in L A283 : X = O, R E = R A7 , R 2 = R B1 ,

in L A284 : X = O, R E = R A7 , R 2 = R B2 ,

in L A285 : X = O, R E = R A8 , R 2 = R B1 ,

in L A286 : X = O, R E = R A8 , R 2 = R B2 ,

in L A287 : X = S, R E = R A5 , R 2 = R B1 ,

in L A288 : X = S, R E = R A5 , R 2 = R B2 ,

in L A289 : X = S, R E = R A6 , R 2 = R B1 ,

in L A290 : X = S, R E = R A6 , R 2 = R B2 ,

in L A291 : X = S, R E = R A7 , R 2 = R B1 ,

in L A292 : X = S, R E = R A7 , R 2 = R B2 ,

in L A293 : X = S, R E = R A8 , R 2 = R B1 , and

in L A294 : X = S, R E = R A8 , R 2 = R B2 .

L A295 through L A310 , each represented by the formula:

wherein in L A295 : X = O, R E = R A5 , R 2 = R B1 ,

in L A296 : X = O, R E = R A5 , R 2 = R B2 ,

in L A297 : X = O, R E = R A6 , R 2 = R B1 ,

in L A298 : X = O, R E = R A6 , R 2 = R B2 ,

in L A299 : X = O, R E = R A7 , R 2 = R B1 ,

in L A300 : X = O, R E = R A7 , R 2 = R B2 ,

in L A301 : X = O, R E = R A8 , R 2 = R B1 ,

in L A302 : X = O, R E = R A8 , R 2 = R B2 ,

in L A303 : X = S, R E = R A5 , R 2 = R B1 ,

in L A304 : X = S, R E = R A5 , R 2 = R B2 ,

in L A305 : X = S, R E = R A6 , R 2 = R B1 ,

in L A306 : X = S, R E = R A6 , R 2 = R B2 ,

in L A307 : X = S, R E = R A7 , R 2 = R B1 ,

in L A308 : X = S, R E = R A7 , R 2 = R B2 ,

in L A309 : X = S, R E = R A8 , R 2 = R B1 , and

in L A310 : X = S, R E = R A8 , R 2 = R B2 .

L A311 through L A326 , each represented by the formula:

wherein in L A311 : R E = R A5 , R 2 = R B1 , R 1 = R C1 ,

in L A312 : R E = R A5 , R 2 = R B2 , R 1 = R C1 ,

in L A313 : R E = R A6 , R 2 = R B1 , R 1 = R C1 ,

in L A314 : R E = R A6 , R 2 = R B2 , R 1 = R C1 ,

in L A315 : R E = R A7 , R 2 = R B1 , R 1 = R C1 ,

in L A316 : R E = R A7 , R 2 = R B2 , R 1 = R C1 ,

in L A317 : R E = R A8 , R 2 = R B1 , R 1 = R C1 ,

in L A318 : R E = R A8 , R 2 = R B2 , R 1 = R C1 ,

in L A319 : R E = R A5 , R 2 = R B1 , R 1 = R C2 ,

in L A320 : R E = R A5 , R 2 = R B2 , R 1 = R C2 ,

in L A321 : R E = R A6 , R 2 = R B1 , R 1 = R C2 ,

in L A322 : R E = R A6 , R 2 = R B2 , R 1 = R C2 ,

in L A323 : R E = R A7 , R 2 = R B1 , R 1 = R C2 ,

in L A324 : R E = R A7 , R 2 = R B2 , R 1 = R C2 ,

in L A325 : R E = R A8 , R 2 = R B1 , R 1 = R C2 , and

in L A326 : R E = R A8 , R 2 = R B2 , R 1 = R C2 .

L A327 through L A342 , each represented by the formula:

wherein in L A327 : R E = R A5 , R 2 = R B1 , R 1 = R C1 ,

in L A328 : R E = R A5 , R 2 = R B2 , R 1 = R C1 ,

in L A329 : R E = R A6 , R 2 = R B1 , R 1 = R C1 ,

in L A330 : R E = R A6 , R 2 = R B2 , R 1 = R C1 ,

in L A331 : R E = R A7 , R 2 = R B1 , R 1 = R C1 ,

in L A332 : R E = R A7 , R 2 = R B2 , R 1 = R C1 ,

in L A333 : R E = R A8 , R 2 = R B1 , R 1 = R C1 ,

in L A334 : R E = R A8 , R 2 = R B2 , R 1 = R C1 ,

in L A335 : R E = R A5 , R 2 = R B1 , R 1 = R C2 ,

in L A336 : R E = R A5 , R 2 = R B2 , R 1 = R C2 ,

in L A337 : R E = R A6 , R 2 = R B1 , R 1 = R C2 ,

in L A338 : R E = R A6 , R 2 = R B2 , R 1 = R C2 ,

in L A339 : R E = R A7 , R 2 = R B1 , R 1 = R C2 ,

in L A340 : R E = R A7 , R 2 = R B2 , R 1 = R C2 ,

in L A341 : R E = R A8 , R 2 = R B1 , R 1 = R C2 , and

in L A342 : R E = R A8 , R 2 = R B2 , R 1 = R C2 .

L A343 through L A358 , each represented by the formula:

wherein in L A343 : R E = R A5 , R 2 = R B1 , R 1 = R C1 ,

in L A344 : R E = R A5 , R 2 = R B2 , R 1 = R C1 ,

in L A345 : R E = R A6 , R 2 = R B1 , R 1 = R C1 ,

in L A346 : R E = R A6 , R 2 = R B2 , R 1 = R C1 ,

in L A347 : R E = R A7 , R 2 = R B1 , R 1 = R C1 ,

in L A348 : R E = R A7 , R 2 = R B2 , R 1 = R C1 ,

in L A349 : R E = R A8 , R 2 = R B1 , R 1 = R C1 ,

in L A350 : R E = R A8 , R 2 = R B2 , R 1 = R C1 ,

in L A351 : R E = R A5 , R 2 = R B1 , R 1 = R C2 ,

in L A352 : R E = R A5 , R 2 = R B2 , R 1 = R C2 ,

in L A353 : R E = R A6 , R 2 = R B1 , R 1 = R C2 ,

in L A354 : R E = R A6 , R 2 = R B2 , R 1 = R C2 ,

in L A355 : R E = R A7 , R 2 = R B1 , R 1 = R C2 ,

in L A356 : R E = R A7 , R 2 = R B2 , R 1 = R C2 ,

in L A357 : R E = R A8 , R 2 = R B1 , R 1 = R C2 , and

in L A358 : R E = R A8 , R 2 = R B2 , R 1 = R C2 .

L A359 through L A374 , each represented by the formula:

wherein in L A359 : R E = R A5 , R 2 = R B1 , R 1 = R C1

in L A360 : R E = R A5 , R 2 = R B2 , R 1 = R C1 ,

in L A361 : R E = R A6 , R 2 = R B1 , R 1 = R C1 ,

in L A362 : R E = R A6 , R 2 = R B2 , R 1 = R C1 ,

in L A363 : R E = R A7 , R 2 = R B1 , R 1 = R C1 ,

in L A364 : R E = R A7 , R 2 = R B2 , R 1 = R C1 ,

in L A365 : R E = R A8 , R 2 = R B1 , R 1 = R C1 ,

in L A366 : R E = R A8 , R 2 = R B2 , R 1 = R C1 ,

in L A367 : R E = R A5 , R 2 = R B1 , R 1 = R C2 ,

in L A368 : R E = R A5 , R 2 = R B2 , R 1 = R C2 ,

in L A369 : R E = R A6 , R 2 = R B1 , R 1 = R C2 ,

in L A370 : R E = R A6 , R 2 = R B2 , R 1 = R C2 ,

in L A371 : R E = R A7 , R 2 = R B1 , R 1 = R C2 ,

in L A372 : R E = R A7 , R 2 = R B2 , R 1 = R C2 ,

in L A373 : R E = R A8 , R 2 = R B1 , R 1 = R C2 , and

in L A374 : R E = R A8 , R 2 = R B2 , R 1 = R C2 .

L A391 through L A406 , each represented by the formula:

wherein in L A391 : X = O, R E = R A5 , R 2 = R B1 ,

in L A392 : X = O, R E = R A5 , R 2 = R B2 ,

in L A393 : X = O, R E = R A6 , R 2 = R B1 ,

in L A394 : X = O, R E = R A6 , R 2 = R B2 ,

in L A395 : X = O, R E = R A7 , R 2 = R B1 ,

in L A396 : X = O, R E = R A7 , R 2 = R B2 ,

in L A397 : X = O, R E = R A8 , R 2 = R B1 ,

in L A398 : X = O, R E = R A8 , R 2 = R B2 ,

in L A399 : X = S, R E = R A5 , R 2 = R B1 ,

in L A400 : X = S, R E = R A5 , R 2 = R B2 ,

in L A401 : X = S, R E = R A6 , R 2 = R B1 ,

in L A402 : X = S, R E = R A6 , R 2 = R B2 ,

in L A403 : X = S, R E = R A7 , R 2 = R B1 ,

in L A404 : X = S, R E = R A7 , R 2 = R B2 ,

in L A405 : X = S, R E = R A8 , R 2 = R B1 , and

in L A406 : X = S, R E = R A8 , R 2 = R B2 .

L A407 through L A422 , each represented by the formula:

wherein in L A407 : X = O, R E = R A5 , R 2 = R B1 ,

in L A408 : X = O, R E = R A5 , R 2 = R B2 ,

in L A409 : X = O, R E = R A6 , R 2 = R B1 ,

in L A410 : X = O, R E = R A6 , R 2 = R B2 ,

in L A411 : X = O, R E = R A7 , R 2 = R B1 ,

in L A412 : X = O, R E = R A7 , R 2 = R B2 ,

in L A413 : X = O, R E = R A8 , R 2 = R B1 ,

in L A414 : X = O, R E = R A8 , R 2 = R B2 ,

in L A415 : X = S, R E = R A5 , R 2 = R B1 ,

in L A416 : X = S, R E = R A5 , R 2 = R B2 ,

in L A417 : X = S, R E = R A6 , R 2 = R B1 ,

in L A418 : X = S, R E = R A6 , R 2 = R B2 ,

in L A419 : X = S, R E = R A7 , R 2 = R B1 ,

in L A420 : X = S, R E = R A7 , R 2 = R B2 ,

in L A421 : X = S, R E = R A8 , R 2 = R B1 , and

in L A422 : X = S, R E = R A8 , R 2 = R B2 .

L A423 through L A438 , each represented by the formula:

wherein in L A423 : X = O, R E = R A5 , R 4 = R B1 ,

in L A424 : X = O, R E = R A5 , R 4 = R B2 ,

in L A425 : X = O, R E = R A6 , R 4 = R B1 ,

in L A426 : X = O, R E = R A6 , R 4 = R B2 ,

in L A427 : X = O, R E = R A7 , R 4 = R B1 ,

in L A428 : X = O, R E = R A7 , R 4 = R B2 ,

in L A429 : X = O, R E = R A8 , R 4 = R B1 ,

in L A430 : X = O, R E = R A8 , R 4 = R B2 ,

in L A431 : X = S, R E = R A5 , R 4 = R B1 ,

in L A432 : X = S, R E = R A5 , R 4 = R B2 ,

in L A433 : X = S, R E = R A6 , R 4 = R B1 ,

in L A434 : X = S, R E = R A6 , R 4 = R B2 ,

in L A435 : X = S, R E = R A7 , R 4 = R B1 ,

in L A436 : X = S, R E = R A7 , R 4 = R B2 ,

in L A437 : X = S, R E = R A8 , R 4 = R B1 , and

in L A438 : X = S, R E = R A8 , R 4 = R B2 .

L A439 through L A454 , each represented by the formula:

wherein in L A439 : X = O, R E = R A5 , R 4 = R B1 ,

in L A440 : X = O, R E = R A5 , R 4 = R B2 ,

in L A441 : X = O, R E = R A6 , R 4 = R B1 ,

in L A442 : X = O, R E = R A6 , R 4 = R B2 ,

in L A443 : X = O, R E = R A7 , R 4 = R B1 ,

in L A444 : X = O, R E = R A7 , R 4 = R B2 ,

in L A445 : X = O, R E = R A8 , R 4 = R B1 ,

in L A446 : X = O, R E = R A8 , R 4 = R B2 ,

in L A447 : X = S, R E = R A5 , R 4 = R B1 ,

in L A448 : X = S, R E = R A5 , R 4 = R B2 ,

in L A449 : X = S, R E = R A6 , R 4 = R B1 ,

in L A450 : X = S, R E = R A6 , R 4 = R B2 ,

in L A451 : X = S, R E = R A7 , R 4 = R B1 ,

in L A452 : X = S, R E = R A7 , R 4 = R B2 ,

in L A453 : X = S, R E = R A8 , R 4 = R B1 , and

in L A454 : X = S, R E = R A8 , R 4 = R B2 .

L A471 through L A478 , each represented by the formula:

wherein in L A471 : R E = R A5 , R 1 = R C1 ,

in L A472 : R E = R A6 , R 1 = R C1 ,

in L A473 : R E = R A7 , R 1 = R C1 ,

in L A474 : R E = R A8 , R 1 = R C1 ,

in L A475 : R E = R A5 , R 1 = R C2 ,

in L A476 : R E = R A6 , R 1 = R C2 ,

in L A477 : R E = R A7 , R 1 = R C2 , and

in L A478 : R E = R A8 , R 1 = R C2 .

L A479 through L A486 , each represented by the formula:

wherein in L A479 : R E = R A5 , R 1 = R C1 ,

in L A480 : R E = R A6 , R 1 = R C1 ,

in L A481 : R E = R A7 , R 1 = R C1 ,

in L A482 : R E = R A8 , R 1 = R C1 ,

in L A483 : R E = R A5 , R 1 = R C2 ,

in L A484 : R E = R A6 , R 1 = R C2 ,

in L A485 : R E = R A7 , R 1 = R C2 , and

in L A486 : R E = R A8 , R 1 = R C2

L A487 through L A494 , each represented by the formula:

wherein in L A487 : R E = R A5 , R 1 = R C1 ,

in L A488 : R E = R A6 , R 1 = R C1 ,

in L A489 : R E = R A7 , R 1 = R C1 ,

in L A490 : R E = R A8 , R 1 = R C1 ,

in L A491 : R E = R A5 , R 1 = R C2 ,

in L A492 : R E = R A6 , R 1 = R C2 ,

in L A493 : R E = R A7 , R 1 = R C2 , and

in L A494 : R E = R A8 , R 1 = R C2 .

L A495 through L A502 , each represented by the formula:

wherein in L A495 : R E = R A5 , R 1 = R C1 ,

in L A496 : R E = R A6 , R 1 = R C1 ,

in L A497 : R E = R A7 , R 1 = R C1 ,

in L A498 : R E = R A8 , R 1 = R C1 ,

in L A499 : R E = R A5 , R 1 = R C2 ,

in L A500 : R E = R A6 , R 1 = R C2 ,

in L A501 : R E = R A7 , R 1 = R C2 , and

in L A502 : R E = R A8 , R 1 = R C2 .

L A535 through L A550 , each represented by the formula:

wherein in L A535 : X = O, R E = R A5 , R 2 = R B1 ,

in L A536 : X = O, R E = R A5 , R 2 = R B2 ,

in L A537 : X = O, R E = R A6 , R 2 = R B1 ,

in L A538 : X = O, R E = R A6 , R 2 = R B2 ,

in L A539 : X = O, R E = R A7 , R 2 = R B1 ,

in L A540 : X = O, R E = R A7 , R 2 = R B2 ,

in L A541 : X = O, R E = R A8 , R 2 = R B1 ,

in L A542 : X = O, R E = R A8 , R 2 = R B2 ,

in L A543 : X = S, R E = R A5 , R 2 = R B1 ,

in L A544 : X = S, R E = R A5 , R 2 = R B2 ,

in L A545 : X = S, R E = R A6 , R 2 = R B1 ,

in L A546 : X = S, R E = R A6 , R 2 = R B2 ,

in L A547 : X = S, R E = R A7 , R 2 = R B1 ,

in L A548 : X = S, R E = R A7 , R 2 = R B2 ,

in L A549 : X = S, R E = R A8 , R 2 = R B1 , and

in L A550 : X = S, R E = R A8 , R 2 = R B2 .

L A551 through L A566 , each represented by the formula:

wherein in L A551 : X = O, R E = R A5 , R 2 = R B1 ,

in L A552 : X = O, R E = R A5 , R 2 = R B2 ,

in L A553 : X = O, R E = R A6 , R 2 = R B1 ,

in L A554 : X = O, R E = R A6 , R 2 = R B2 ,

in L A555 : X = O, R E = R A7 , R 2 = R B1 ,

in L A556 : X = O, R E = R A7 , R 2 = R B2 ,

in L A557 : X = O, R E = R A8 , R 2 = R B1 ,

in L A558 : X = O, R E = R A8 , R 2 = R B2 ,

in L A559 : X = S, R E = R A5 , R 2 = R B1 ,

in L A560 : X = S, R E = R A5 , R 2 = R B2 ,

in L A561 : X = S, R E = R A6 , R 2 = R B1 ,

in L A562 : X = S, R E = R A6 , R 2 = R B2 ,

in L A563 : X = S, R E = R A7 , R 2 = R B1 ,

in L A564 : X = S, R E = R A7 , R 2 = R B2 ,

in L A565 : X = S, R E = R A8 , R 2 = R B1 , and

in L A566 : X = S, R E = R A8 , R 2 = R B2 ,

L A567 through L A582 , each represented by the formula:

wherein in L A567 : X = O, R E = R A5 , R 2 = R B1 ,

in L A568 : X = O, R E = R A5 , R 2 = R B2 ,

in L A569 : X = O, R E = R A6 , R 2 = R B1 ,

in L A570 : X = O, R E = R A6 , R 2 = R B2 ,

in L A571 : X = O, R E = R A7 , R 2 = R B1 ,

in L A572 : X = O, R E = R A7 , R 2 = R B2 ,

in L A573 : X = O, R E = R A8 , R 2 = R B1 ,

in L A574 : X = O, R E = R A8 , R 2 = R B2 ,

in L A575 : X = S, R E = R A5 , R 2 = R B1 ,

in L A576 : X = S, R E = R A5 , R 2 = R B2 ,

in L A577 : X = S, R E = R A6 , R 2 = R B1 ,

in L A578 : X = S, R E = R A6 , R 2 = R B2 ,

in L A579 : X = S, R E = R A7 , R 2 = R B1 ,

in L A580 : X = S, R E = R A7 , R 2 = R B2 ,

in L A581 : X = S, R E = R A8 , R 2 = R B1 , and

in L A582 : X = S, R E = R A8 , R 2 = R B2 .

L A583 through L A598 , each represented by the formula:

wherein in L A583 : X = O, R E = R A5 , R 2 = R B1 ,

in L A584 : X = O, R E = R A5 , R 2 = R B2 ,

in L A585 : X = O, R E = R A6 , R 2 = R B1 ,

in L A586 : X = O, R E = R A6 , R 2 = R B2 ,

in L A587 : X = O, R E = R A7 , R 2 = R B1 ,

in L A588 : X = O, R E = R A7 , R 2 = R B2 ,

in L A589 : X = O, R E = R A8 , R 2 = R B1 ,

in L A590 : X = O, R E = R A8 , R 2 = R B2 ,

in L A591 : X = S, R E = R A5 , R 2 = R B1 ,

in L A592 : X = S, R E = R A5 , R 2 = R B2 ,

in L A593 : X = S, R E = R A6 , R 2 = R B1 ,

in L A594 : X = S, R E = R A6 , R 2 = R B2 ,

in L A595 : X = S, R E = R A7 , R 2 = R B1 ,

in L A596 : X = S, R E = R A7 , R 2 = R B2 ,

in L A597 : X = S, R E = R A8 , R 2 = R B1 , and

in L A598 : X = S, R E = R A8 , R 2 = R B2 .

L A599 through L A606 , each represented by the formula:

wherein in L A599 : R E = R A5 , R 1 = R C1 ,

in L A600 : R E = R A6 , R 1 = R C1 ,

in L A601 : R E = R A7 , R 1 = R C1 ,

in L A602 : R E = R A8 , R 1 = R C1 ,

in L A603 : R E = R A5 , R 1 = R C2

in L A604 : R E = R A6 , R 1 = R C2 ,

in L A605 : R E = R A7 , R 1 = R C2 , and

in L A606 : R E = R A8 , R 1 = R C2 .

L A607 through L A614 , each represented by the formula:

wherein in L A607 : R E = R A5 , R 1 = R C1 ,

in L A608 : R E = R A6 , R 1 = R C1 ,

in L A609 : R E = R A7 , R 1 = R C1 ,

in L A610 : R E = R A8 , R 1 = R C1 ,

in L A611 : R E = R A5 , R 1 = R C2 ,

in L A612 : R E = R A6 , R 1 = R C2 ,

in L A613 : R E = R A7 , R 1 = R C2 , and

in L A614 : R E = R A8 , R 1 = R C2 ,

L A615 through L A622 , each represented by the formula:

wherein in L A615 : R E = R A5 , R 1 = R C1 ,

in L A616 : R E = R A6 , R 1 = R C1 ,

in L A617 : R E = R A7 , R 1 = R C1 ,

in L A618 : R E = R A8 , R 1 = R C1 ,

in L A619 : R E = R A5 , R 1 = R C2 ,

in L A620 : R E = R A6 , R 1 = R C2 ,

in L A621 : R E = R A7 , R 1 = R C2 , and

in L A622 : R E = R A8 , R 1 = R C2 .

and L A623 through L A630 , each represented by the formula:

wherein in L A623 : R E = R A5 , R 1 = R C1 ,

in L A624 : R E = R A6 , R 1 = R C1 ,

in L A625 : R E = R A7 , R 1 = R C1 ,

in L A626 : R E = R A8 , R 1 = R C1 ,

in L A627 : R E = R A5 , R 1 = R C2 ,

in L A628 : R E = R A6 , R 1 = R C2 ,

in L A629 : R E = R A7 , R 1 = R C2 , and

in L A630 : R E = R A8 , R 1 = R C2 ; and

wherein R A5 to R A8 have the following structures:

R A5 , R A6 , R A7 , and R A8 ;

wherein R B1 and R B2 have the following structures:

R B1 and R B2 , and

wherein R C1 to R C2 have the following structures:

R C1 and R C2 .

14. The compound of claim 13 , wherein y is 1 or 2; L A is selected from the group consisting of L Ai , where i is selected from 1 to 96, 109, 110, 115, 116, 121, 133, 127, 128, 133, 134, 139, 140, 145, 146, 151, 152, 157, 158, 163, 164, 311 to 374, 471 to 502, and 599 to 630; and

L B is selected from the group consisting of:

15. The compound of claim 13 , wherein z is 1 or 2; L A is selected from the group consisting of L Ai , where i is selected from 171 to 182, 215 to 246, 279 to 310, 391 to 454, and 535 to 598; and L C is selected from the group consisting of:

16. The compound of claim 13 , wherein the compound has the formula Ir(L Ak )(L Bj ) 2 ;

wherein k is an integer selected from 1 to 96, 109, 110, 115, 116, 121, 133, 127, 128, 133, 134, 139, 140, 145, 146, 151, 152, 157, 158, 163, 164, 311 to 374, 471 to 502, and 599 to 630, and j is an integer from 1 to 41; and

wherein L B1 through L B41 are defined as follows:

17. The compound of claim 13 , wherein the compound has the formula Ir(L Ak ) 2 (L Ci );

wherein k is an integer from 171 to 182, 215 to 246, 279 to 310, 391 to 454, and 535 to 598, and i is an integer from 1 to 13; and wherein L C1 through L C13 are defined as follows:

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(L A ) x (L B ) y (L C ) z :