Fluorinated organic electroluminescent materials and devices
Novel ligands for metal complex compounds that are useful as a phosphorescent emitter in organic light emitting devices that incorporate fluorinated side chains in the ligands are disclosed. Such metal complex 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.
1. A composition comprising a first compound having 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 L 1 , L 2 , and L 3 can be the same or different;
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 L 1 , L 2 , and L 3 are each independently selected from the group consisting of:
wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a , R b , R c , and R d 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 two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a ring or form a multidentate ligand;
wherein at least one of the R a , R b , R c , and R d includes at least one R, wherein R is 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 an aromatic ring;
wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring; and
wherein when one of L 1 , L 2 , and L 3 is
then at least one of the other L 1 , L 2 , and L 3 is different.
2. The composition of claim 1 , wherein the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.
3. The composition of claim 1 , wherein the first compound is a metal coordination complex having a metal-carbon bond.
4. The composition of claim 1 , wherein C having an F attached thereto is separated by at least two carbon atoms from the aromatic ring.
5. The composition of claim 1 , wherein C having an F attached thereto is separated by at least three carbon atoms from the aromatic ring.
6. The composition of claim 1 , wherein each of the at least one R contains at least one CF 3 group.
7. The composition of claim 1 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ), wherein L 1 has the formula selected from the group consisting of:
and
wherein L 2 has the formula:
8. The composition of claim 7 , 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;
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.
9. The composition of claim 1 , wherein L 1 and L 2 are different and each independently selected from the group consisting of:
10. The composition of claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of:
11. The composition of claim 1 , wherein the first compound has the formula of Pt(L 1 ) 2 or Pt(L 1 )(L 2 ).
12. 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 deuterium.
13. The composition of claim 1 , wherein L 1 , L 2 , and L 3 are each independently 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 A15 , 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 ;,
and
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 ,
and in L A451 , R = R A41 ;,
wherein, R A1 through R A41 have the formulas:
14. The composition of claim 1 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ), wherein L 1 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 A15 , 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 LA 123 , R = R A41 ;,
LA 124 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 LA 369 , 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 ;,
and
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 ,
and in L A451 , R = R A41 ;,
wherein, R A1 through R A41 have the formulas:
and
wherein L 2 is selected from the group consisting of:
15. The compound of claim 14 , wherein the first compound is selected from the group consisting of Compound 1 through Compound 5,863; and
wherein each of Compound x, where x=451j+k−451, k is an integer from 1 to 451, and j is an integer from 1 to 13, has the formula Ir(L Ak ) 2 (L Bj ).
16. The composition of claim 1 , wherein the first compound is selected from the group consisting of
17. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode,
comprising a first compound, 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 L 1 , L 2 , and L 3 can be the same or different;
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 L 1 , L 2 , and L 3 are each independently selected from the group consisting of:
wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a , R b , R c , and R d 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 two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a ring or form a multidentate ligand;
wherein at least one of the R a , R b , R c , and R d includes at least one R, wherein R is 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 an aromatic ring;
wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring; and
wherein if one of L 1 , L 2 , and L 3 is
then at least one of the other L 1 , L 2 , and L 3 is different.
18. The first device of claim 17 , wherein the first compound is selected from the group consisting of
19. The first device of claim 17 , wherein the first device is a consumer product selected from the group consisting of flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cell phones, tablets, phablets, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, a wall, theater or stadium screen, and a sign.