IP Library › Granted Patent US 10,854,826

Granted Patent B2

US 10,854,826 · App. 15/911,418 · Granted Dec 1, 2020

Organic electroluminescent compounds, compositions and devices

Inventors: Jui-Yi Tsai (Newtown, PA); Alexey Borisovich Dyatkin (Ambler, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Walter Yeager (Yardley, PA); Chuanjun Xia (Lawrenceville, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

H01L51/0085 C07F15/0033 C09K11/06 C09K2211/1007 C09K2211/1029 C09K2211/1033 C09K2211/1044 C09K2211/185 H01L51/0072 H01L51/0074 H01L51/5016 H01L51/5024 H01L51/5206 H01L51/5221

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Quick Facts

Patent No.: US 10,854,826
App. No.: 15/911,418
Granted: Dec 1, 2020
Kind: B2

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Abstract

An OLED including an organic layer that contains metal complex compounds that are useful as a phosphorescent emitter is disclosed. The metal complex compounds include ligands that incorporate fluorinated side chains and has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring. In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

Claims (500)

1. A composition comprising a first compound;

wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;

wherein the first compound has at least one aromatic ring and at least one substituent R;

wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;

wherein each of the at least one R is directly bonded to one of the aromatic rings;

wherein in each of the at least one R, any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;

wherein the first compound has the formula of M(L 1 ) x (L 2 ) y (L 3 ) z ;

wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;

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 when L 1 , L 2 , and L 3 are each present, at least one of L 1 , L 2 , and L 3 is different from the others;

wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of:

wherein when one or both of L 2 or L 3 are present, L 2 or L 3 each can independently be

wherein each X 1 to X 13 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, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may represent from a mono substitution to a maximum possible number of substitutions, or no substitution;

wherein each of R′, R″, R a , R b , R c , and R d is 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 two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand; and

wherein L 1 comprises an R of the at least one substituent R.

2. The composition of claim 1 , wherein X is selected from the group consisting of NR′, O, S, Se, CR′R″, and SiR′R″.

3. The composition of claim 1 , wherein each R′, R″, R a , R b , R c , and R d is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

4. The composition of claim 1 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ).

5. The composition of claim 4 , wherein L 1 has the formula selected from the group consisting of:

and

wherein L 2 has the formula:

6. The composition of claim 5 , wherein L 2 has the formula:

wherein R e , R f , R h , and R i , are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

wherein at least one of R e , R f , R h , and R i has at least two carbon atoms; and

wherein R g is selected from 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.

7. The composition of claim 4 , wherein L 1 and L 2 are different and each independently selected from the group consisting of:

8. The composition of claim 1 , wherein the first compound has the formula of Pt(L 1 ) 2 or Pt(L 1 )(L 2 ).

9. The composition of claim 1 , wherein at least one of R a , R b , R c , and R d includes an alkyl or cycloalkyl group that includes CD, CD 2 , or CD 3 , wherein D is a deuterium.

10. The composition of claim 1 , wherein the any C having an F attached thereto is separated by at least two carbon atoms from the aromatic ring.

11. The composition of claim 1 , wherein the any C having an F attached thereto is separated by at least one CD 2 group from the aromatic ring, wherein D is a deuterium.

12. The composition of claim 1 , wherein each of the at least one R contains at least one CF 3 group.

13. The composition of claim 1 , wherein at least one of L 1 , L 2 , and L 3 is a ligand L A , wherein L A is selected from the group consisting of:

L A1 through L A41 , each

represented by the formula

wherein,

in L A1 , R = R A1 , in L A2 , R = R A2 ,

in L A3 , R = R A3 , in L A4 , R = R A4 ,

in L A5 , R = R A5 , in L A6 , R = R A6 ,

in L A7 , R = R A7 , in L A8 , R = R A8 ,

in L A9 , R = R A9 , in L A10 , R = R A10 ,

in L A11 , R = R A11 , in L A12 , R = R A12 ,

in L A13 , R = R A13 , in L A14 , R = R A14 ,

in L A15 , R = R A15 , in L A16 , R = R A16 ,

in L A17 , R = R A17 , in L A18 , R = R A18 ,

in L A19 , R = R A19 , in L A20 , R = R A20 ,

in L A21 , R = R A21 , in L A22 , R = R A22 ,

in L A23 , R = R A23 , in L A24 , R = R A24 ,

in L A25 , R = R A25 , in L A26 , R = R A26 ,

in L A27 , R = R A27 , in L A28 , R = R A28 ,

in L A29 , R = R A29 , in L A30 , R = R A30 ,

in L A31 , R = R A31 , in L A32 , R = R A32 ,

in L A33 , R = R A33 , in L A34 , R = R A34 ,

in L A35 , R = R A35 , in L A36 , R = R A36 ,

in L A37 , R = R A37 , in L A38 , R = R A38 ,

in L A39 , R = R A39 , in L A40 , R = R A40 ,

and in L A41 , R = R A41 ;

L A42 through L A82 , each

represented by the formula

wherein,

in L A42 , R = R A1 , in L A43 , R = R A2 ,

in L A44 , R = R A3 , in L A45 , R = R A4 ,

in L A46 , R = R A5 , in L A47 , R = R A6 ,

in L A48 , R = R A7 , in L A49 , R = R A8 ,

in L A50 , R = R A9 , in L A51 , R = R A10 ,

in L A52 , R = R A11 , in L A53 , R = R A12 ,

in L A54 , R = R A13 , in L A55 , R = R A14 ,

in L A56 , R = R A15 , in L A57 , R = R A16 ,

in L A58 , R = R A17 , in L A59 , R = R A18 ,

in L A60 , R = R A19 , in L A61 , R = R A20 ,

in L A62 , R = R A21 , in L A63 , R = R A22 ,

in L A64 , R = R A23 , in L A65 , R = R A24 ,

in L A66 , R = R A25 , in L A67 , R = R A26 ,

in L A68 , R = R A27 , in L A69 , R = R A28 ,

in L A70 , R = R A29 , in L A71 , R = R A30 ,

in L A72 , R = R A31 , in L A73 , R = R A32 ,

in L A74 , R = R A33 , in L A75 , R = R A34 ,

in L A76 , R = R A35 , in L A77 , R = R A36 ,

in L A78 , R = R A37 , in L A79 , R = R A38 ,

in L A80 , R = R A39 , in L A81 , R = R A40 ,

and in L A82 , R = R A41 ;

L A83 through L A123 , each

represented by the formula

wherein,

in L A83 , R = R A1 , in L A84 , R = R A2 ,

in L A85 , R = R A3 , in L A86 , R = R A4 ,

in L A87 , R = R A5 , in L A88 , R = R A6 ,

in L A89 , R = R A7 , in L A90 , R = R A8 ,

in L A91 , R = R A9 , in L A92 , R = R A10 ,

in L A93 , R = R A11 , in L A94 , R = R A12 ,

in L A95 , R = R A13 , in L A96 , R = R A14 ,

in L A97 , R = R A18 , in L A98 , R = R A16 ,

in L A99 , R = R A17 , in L A100 , R = R A18 ,

in L A101 , R = R A19 , in L A102 , R = R A20 ,

in L A103 , R = R A21 , in L A104 , R = R A22 ,

in L A105 , R = R A23 , in L A106 , R = R A24 ,

in L A107 , R = R A25 , in L A108 , R = R A26 ,

in L A109 , R = R A27 , in L A110 , R = R A28 ,

in L A111 , R = R A29 , in L A112 , R = R A30 ,

in L A113 , R = R A31 , in L A114 , R = R A32 ,

in L A115 , R = R A33 , in L A116 , R = R A34 ,

in L A117 , R = R A35 , in L A118 , R = R A36 ,

in L A119 , R = R A37 , in L A120 , R = R A38 ,

in L A121 , R = R A39 , in L A122 , R = R A40 ,

and in L A123 , R = R A41 ;

L A124 through L A164 , each

represented by the formula

wherein,

in L A124 , R = R A1 , in L A125 , R = R A2 ,

in L A126 , R = R A3 , in L A127 , R = R A4 ,

in L A128 , R = R A5 , in L A129 , R = R A6 ,

in L A130 , R = R A7 , in L A131 , R = R A8 ,

in L A132 , R = R A9 , in L A133 , R = R A10 ,

in L A134 , R = R A11 , in L A135 , R = R A12 ,

in L A136 , R = R A13 , in L A137 , R = R A14 ,

in L A138 , R = R A15 , in L A139 , R = R A16 ,

in L A140 , R = R A17 , in L A141 , R = R A18 ,

in L A142 , R = R A19 , in L A143 , R = R A20 ,

in L A144 , R = R A21 , in L A145 , R = R A22 ,

in L A146 , R = R A23 , in L A147 , R = R A24 ,

in L A148 , R = R A25 , in L A149 , R = R A26 ,

in L A150 , R = R A27 , in L A151 , R = R A28 ,

in L A152 , R = R A29 , in L A153 , R = R A30 ,

in L A154 , R = R A31 , in L A155 , R = R A32 ,

in L A156 , R = R A33 , in L A157 , R = R A34 ,

in L A158 , R = R A35 , in L A159 , R = R A36 ,

in L A160 , R = R A37 , in L A161 , R = R A38 ,

in L A162 , R = R A39 , in L A163 , R = R A40 ,

and in L A164 , R = R A41 ,

L A165 through L A205 , each

represented by the formula

wherein,

in L A165 , R = R A1 , in L A166 , R = R A2 ,

in L A167 , R = R A3 , in L A168 , R = R A4 ,

in L A169 , R = R A5 , in L A170 , R = R A6 ,

in L A171 , R = R A7 , in L A172 , R = R A8 ,

in L A173 , R = R A9 , in L A174 , R = R A10 ,

in L A175 , R = R A11 , in L A176 , R = R A12 ,

in L A177 , R = R A13 , in L A178 , R = R A14 ,

in L A179 , R = R A15 , in L A180 , R = R A16 ,

in L A181 , R = R A17 , in L A182 , R = R A18 ,

in L A183 , R = R A19 , in L A184 , R = R A20 ,

in L A185 , R = R A21 , in L A186 , R = R A22 ,

in L A187 , R = R A23 , in L A188 , R = R A24 ,

in L A189 , R = R A25 , in L A190 , R = R A26 ,

in L A191 , R = R A27 , in L A192 , R = R A28 ,

in L A193 , R = R A29 , in L A194 , R = R A30 ,

in L A195 , R = R A31 , in L A196 , R = R A32 ,

in L A197 , R = R A33 , in L A198 , R = R A34 ,

in L A199 , R = R A35 , in L A200 , R = R A36 ,

in L A201 , R = R A37 , in L A202 , R = R A38 ,

in L A203 , R = R A39 , in L A204 , R = R A40 ,

and in L A205 , R = R A41 ;

L A206 through L A246 , each

represented by the formula

wherein,

in L A206 , R = R A1 , in L A207 , R = R A2 ,

in L A208 , R = R A3 , in L A209 , R = R A4 ,

in L A210 , R = R A5 , in L A211 , R = R A6 ,

in L A212 , R = R A7 , in L A213 , R = R A8 ,

in L A214 , R = R A9 , in L A215 , R = R A10 ,

in L A216 , R = R A11 , in L A217 , R = R A12 ,

in L A218 , R = R A13 , in L A219 , R = R A14 ,

in L A220 , R = R A15 , in L A221 , R = R A16 ,

in L A222 , R = R A17 , in L A223 , R = R A18 ,

in L A224 , R = R A19 , in L A225 , R = R A20 ,

in L A226 , R = R A21 , in L A227 , R = R A22 ,

in L A228 , R = R A23 , in L A229 , R = R A24 ,

in L A230 , R = R A25 , in L A231 , R = R A26 ,

in L A232 , R = R A27 , in L A233 , R = R A28 ,

in L A234 , R = R A29 , in L A235 , R = R A30 ,

in L A236 , R = R A31 , in L A237 , R = R A32 ,

in L A238 , R = R A33 , in L A239 , R = R A34 ,

in L A240 , R = R A35 , in L A241 , R = R A36 ,

in L A242 , R = R A37 , in L A243 , R = R A38 ,

in L A244 , R = R A39 , in L A245 , R = R A40 ,

and in L A246 , R = R A41 ;

L A247 through L A287 , each

represented by the formula

wherein,

in L A247 , R = R A1 , in L A248 , R = R A2 ,

in L A249 , R = R A3 , in L A250 , R = R A4 ,

in L A251 , R = R A5 , in L A252 , R = R A6 ,

in L A253 , R = R A7 , in L A254 , R = R A8 ,

in L A255 , R = R A9 , in L A256 , R = R A10 ,

in L A257 , R = R A11 , in L A258 , R = R A12 ,

in L A259 , R = R A13 , in L A260 , R = R A14 ,

in L A261 , R = R A15 , in L A262 , R = R A16 ,

in L A263 , R = R A17 , in L A264 , R = R A18 ,

in L A265 , R = R A19 , in L A266 , R = R A20 ,

in L A267 , R = R A21 , in L A268 , R = R A22 ,

in L A269 , R = R A23 , in L A270 , R = R A24 ,

in L A271 , R = R A25 , in L A272 , R = R A26 ,

in L A273 , R = R A27 , in L A274 , R = R A28 ,

in L A275 , R = R A29 , in L A276 , R = R A30 ,

in L A277 , R = R A31 , in L A278 , R = R A32 ,

in L A279 , R = R A33 , in L A280 , R = R A34 ,

in L A281 , R = R A35 , in L A282 , R = R A36 ,

in L A283 , R = R A37 , in L A284 , R = R A38 ,

in L A285 , R = R A39 , in L A286 , R = R A40 ,

and in L A287 , R = R A41 ;

L A288 through L A328 , each

represented by the formula

wherein,

in L A288 , R = R A1 , in L A289 , R = R A2 ,

in L A290 , R = R A3 , in L A291 , R = R A4 ,

in L A292 , R = R A5 , in L A293 , R = R A6 ,

in L A294 , R = R A7 , in L A295 , R = R A8 ,

in L A296 , R = R A9 , in L A297 , R = R A10 ,

in L A298 , R = R A11 , in L A299 , R = R A12 ,

in L A300 , R = R A13 , in L A301 , R = R A14 ,

in L A302 , R = R A15 , in L A303 , R = R A16 ,

in L A304 , R = R A17 , in L A305 , R = R A18 ,

in L A306 , R = R A19 , in L A307 , R = R A20 ,

in L A308 , R = R A21 , in L A309 , R = R A22 ,

in L A310 , R = R A23 , in L A311 , R = R A24 ,

in L A312 , R = R A25 , in L A313 , R = R A26 ,

in L A314 , R = R A27 , in L A315 , R = R A28 ,

in L A316 , R = R A29 , in L A317 , R = R A30 ,

in L A318 , R = R A31 , in L A319 , R = R A32 ,

in L A320 , R = R A33 , in L A321 , R = R A34 ,

in L A322 , R = R A35 , in L A323 , R = R A36 ,

in L A324 , R = R A37 , in L A325 , R = R A38 ,

in L A326 , R = R A39 , in L A327 , R = R A40 ,

and in L A328 , R = R A41 ;

L A329 through L A369 , each

represented by the formula

wherein,

in L A329 , R = R A1 , in L A330 , R = R A2 ,

in L A331 , R = R A3 , in L A332 , R = R A4 ,

in L A333 , R = R A5 , in L A334 , R = R A6 ,

in L A335 , R = R A7 , in L A336 , R = R A8 ,

in L A337 , R = R A9 , in L A338 , R = R A10 ,

in L A339 , R = R A11 , in L A340 , R = R A12 ,

in L A341 , R = R A13 , in L A342 , R = R A14 ,

in L A343 , R = R A15 , in L A344 , R = R A16 ,

in L A345 , R = R A17 , in L A346 , R = R A18 ,

in L A347 , R = R A19 , in L A348 , R = R A20 ,

in L A349 , R = R A21 , in L A350 , R = R A22 ,

in L A351 , R = R A23 , in L A352 , R = R A24 ,

in L A353 , R = R A25 , in L A354 , R = R A26 ,

in L A355 , R = R A27 , in L A356 , R = R A28 ,

in L A357 , R = R A29 , in L A358 , R = R A30 ,

in L A359 , R = R A31 , in L A360 , R = R A32 ,

in L A361 , R = R A33 , in L A362 , R = R A34 ,

in L A363 , R = R A35 , in L A364 , R = R A36 ,

in L A365 , R = R A37 , in L A366 , R = R A38 ,

in L A367 , R = R A39 , in L A368 , R = R A40 ,

and in L A369 , R = R A41 ;

L A370 through L A410 , each

represented by the formula

wherein,

in L A370 , R = R A1 , in L A371 , R = R A2 ,

in L A372 , R = R A3 , in L A373 , R = R A4 ,

in L A374 , R = R A5 , in L A375 , R = R A6 ,

in L A376 , R = R A7 , in L A377 , R = R A8 ,

in L A378 , R = R A9 , in L A379 , R = R A10 ,

in L A380 , R = R A11 , in L A381 , R = R A12 ,

in L A382 , R = R A13 , in L A383 , R = R A14 ,

in L A384 , R = R A15 , in L A385 , R = R A16 ,

in L A386 , R = R A17 , in L A387 , R = R A18 ,

in L A388 , R = R A19 , in L A389 , R = R A20 ,

in L A390 , R = R A21 , in L A391 , R = R A22 ,

in L A392 , R = R A23 , in L A393 , R = R A24 ,

in L A394 , R = R A25 , in L A395 , R = R A26 ,

in L A396 , R = R A27 , in L A397 , R = R A28 ,

in L A398 , R = R A29 , in L A399 , R = R A30 ,

in L A400 , R = R A31 , in L A401 , R = R A32 ,

in L A402 , R = R A33 , in L A403 , R = R A34 ,

in L A404 , R = R A35 , in L A405 , R = R A36 ,

in L A406 , R = R A37 , in L A407 , R = R A38 ,

in L A408 , R = R A39 , in L A409 , R = R A40 ,

and in L A410 , R = R A41 ;

L A411 through L A451 , each

represented by the formula

wherein,

in L A411 , R = R A1 , in L A412 , R = R A2 ,

in L A413 , R = R A3 , in L A414 , R = R A4 ,

in L A415 , R = R A5 , in L A416 , R = R A6 ,

in L A417 , R = R A7 , in L A418 , R = R A8 ,

in L A419 , R = R A9 , in L A420 , R = R A10 ,

in L A421 , R = R A11 , in L A422 , R = R A12 ,

in L A423 , R = R A13 , in L A424 , R = R A14 ,

in L A425 , R = R A15 , in L A426 , R = R A16 ,

in L A427 , R = R A17 , in L A428 , R = R A18 ,

in L A429 , R = R A19 , in L A430 , R = R A20 ,

in L A431 , R = R A21 , in L A432 , R = R A22 ,

in L A433 , R = R A23 , in L A434 , R = R A24 ,

in L A435 , R = R A25 , in L A436 , R = R A26 ,

in L A437 , R = R A27 , in L A438 , R = R A28 ,

in L A439 , R = R A29 , in L A440 , R = R A30 ,

in L A441 , R = R A31 , in L A442 , R = R A32 ,

in L A443 , R = R A33 , in L A444 , R = R A34 ,

in L A445 , R = R A35 , in L A446 , R = R A36 ,

in L A447 , R = R A37 , in L A448 , R = R A38 ,

in L A449 , R = R A39 , in L A450 , R = R A40 ,

in L A451 , R = R A41 , in L A452 , R = R A42 ,

and in L A453 , R = R A43 ;

L A454 through L A458 , each

represented by the formula

wherein,

in L A454 , R = R A2 , in L A455 , R = R A11 ,

in L A456 , R = R A18 , in L A457 , R = R A25 ,

and in L A458 , R = R A28 ;

and in L A453 , R = R A43 ;

L A459 through L A463 , each

represented by the formula

wherein,

in L A459 , R = R A2 , in L A460 , R = R A11 ,

in L A461 , R = R A18 , in L A462 , R = R A25 ,

and in L A463 , R = R A28 ;

L A464 through L A468 , each

represented by the formula

wherein,

in L A464 , R = R A2 , in L A465 , R = R A11 ,

in L A466 , R = R A18 , in L A467 , R = R A25 ,

and in L A468 , R = R A28 ;

L A469 through L A473 , each

represented by the formula

wherein,

in L A469 , R = R A2 , in L A470 , R = R A11 ,

in L A471 , R = R A18 , in L A472 , R = R A25 ,

and in L A473 , R = R A28 ;

L A474 through L A478 , each

represented by the formula

wherein,

in L A474 , R = R A2 , in L A475 , R = R A11 ,

in L A476 , R = R A18 , in L A477 , R = R A25 ,

and in L A478 , R = R A28 ;

L A479 through L A483 , each

represented by the formula

wherein,

in L A479 , R = R A2 , in L A480 , R = R A11 ,

in L A481 , R = R A18 , in L A482 , R = R A25 ,

and in L A483 , R = R A28 ;

L A484 through L A488 , each

represented by the formula

wherein,

in L A484 , R = R A2 , in L A485 , R = R A11 ,

in L A486 , R = R A18 , in L A487 , R = R A25 ,

and in L A488 , R = R A28 ;

L A489 through L A493 , each

represented by the formula

wherein,

in L A489 , R = R A2 , in L A490 , R = R A11 ,

in L A491 , R = R A18 , in L A492 , R = R A25 ,

and in L A493 , R = R A28 ;

L A494 through L A498 , each

represented by the formula

wherein,

in L A494 , R = R A2 , in L A495 , R = R A11 ,

in L A496 , R = R A18 , in L A497 , R = R A25 ,

and in L A498 , R = R A28 ;

L A499 through L A503 , each

represented by the formula

wherein,

in L A499 , R = R A2 , in L A500 , R = R A11 ,

in L A501 , R = R A18 , in L A502 , R = R A25 ,

and in L A503 , R = R A28 ;

L A499 through L A503 , each

represented by the formula

wherein,

in L A504 , R = R A2 , in L A505 , R = R A11 ,

in L A506 , R = R A18 , in L A507 , R = R A25 ,

and in L A508 , R = R A28 ;

L A508 through L A512 , each

represented by the formula

wherein,

in L A508 , R = R A2 , in L A509 , R = R A11 ,

in L A510 , R = R A18 , in L A511 , R = R A25 ,

and in L A512 , R = R A28 ;

L A513 through L A517 , each

represented by the formula

wherein,

in L A513 , R = R A2 , in L A514 , R = R A11 ,

in L A515 , R = R A18 , in L A516 , R = R A25 ,

and in L A517 , R = R A28 ;

L A518 through L A522 , each

represented by the formula

wherein,

in L A518 , R = R A2 , in L A519 , R = R A11 ,

in L A520 , R = R A18 , in L A521 , R = R A25 ,

and in L A522 , R = R A28 ;

L A513 through L A527 , each

represented by the formula

wherein,

in L A523 , R = R A2 , in L A524 , R = R A11 ,

in L A525 , R = R A18 , in L A526 , R = R A25 ,

and in L A527 , R = R A28 ;

L A528 through L A532 , each

represented by the formula

wherein,

in L A528 , R = R A2 , in L A529 , R = R A11 ,

in L A530 , R = R A18 , in L A531 , R = R A25 ,

and in L A532 , R = R A28 ;

L A533 through L A537 , each

represented by the formula

wherein,

in L A533 , R = R A2 , in L A534 , R = R A11 ,

in L A535 , R = R A18 , in L A536 , R = R A25 ,

and in L A537 , R = R A28 ;

L A538 through L A542 , each

represented by the formula

wherein,

in L A538 , R = R A2 , in L A539 , R = R A11 ,

in L A540 , R = R A18 , in L A541 , R = R A25 ,

and in L A542 , R = R A28 ;

L A543 through L A547 , each

represented by the formula

wherein,

in L A543 , R = R A2 , in L A544 , R = R A11 ,

in L A545 , R = R A18 , in L A546 , R = R A25 ,

and in L A547 , R = R A28 ;

L A548 through L A552 , each

represented by the formula

wherein,

in L A548 , R = R A2 , in L A549 , R = R A11 ,

in L A550 , R = R A18 , in L A551 , R = R A25 ,

and in L A552 , R = R A28 ;

L A553 through L A557 , each

represented by the formula

wherein,

in L A553 , R = R A2 , in L A554 , R = R A11 ,

in L A555 , R = R A18 , in L A556 , R = R A25 ,

and in L A557 , R = R A28 ; and

L A558 through L A562 , each

represented by the formula

wherein,

in L A558 , R = R A2 , in L A559 , R = R A11 ,

in L A560 , R = R A18 , in L A561 , R = R A25 ,

and in L A562 , R = R A28 ;

and

wherein R A1 through R A43 have the formulas:

14. The composition of claim 13 , wherein the first compound is selected from the group consisting of:

Compound Ax, having the formula Ir(L Ak ) 2 (L Cj ), wherein x is an integer from 1 to 15,174;

Compound By having the formula Ir(L Ai ) 3 , wherein y is an integer from 1 to 562; or

Compound Cz having the formula Ir(L Ai )(L Bk ) 2 , wherein z is an integer from 1 to 258,520;

wherein x=562j+k 562, y=i, z=460i+k−460;

wherein k is an integer from 1 to 460, j is an integer from 1 to 27, and i is an integer from 1 to 562; and

wherein L Cj has the following structures:

and

wherein L Bk has the following structures:

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 first compound;

wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;

wherein the first compound has at least one aromatic ring and at least one substituent R;

wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;

wherein each of the at least one R is directly bonded to one of the aromatic rings;

wherein in each of the at least one R, any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;

wherein the first compound has the formula of M(L 1 ) x (L 2 ) y (L 3 ) z ;

wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;

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 when L 1 , L 2 , and L 3 are each present, at least one of L 1 , L 2 , and L 3 is different from the others;

wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of:

wherein when one or both of L 2 or L 3 are present, L 2 or L 3 each can independently be

wherein each X 1 to X 13 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, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d represents from a mono substitution to a maximum possible number of substitutions, or no substitutions;

wherein each of R′, R″, R a , R b , R c , and R d is 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 two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand; and

wherein L 1 comprises an R of the at least one substituent R.

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

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

18. The OLED of claim 17 , wherein the organic layer further comprises a host; wherein the host material is selected from the group consisting of:

and combinations thereof.

19. A consumer product comprising an organic light-emitting device (OLED) comprising: