IP Library › Granted Patent US 10,998,508

Granted Patent B2

US 10,998,508 · App. 15/684,307 · Granted May 4, 2021

Organic electroluminescent materials and devices

Inventors: Pierre-Luc T. Boudreault (Pennington, NJ); Walter Yeager (Yardley, PA); Chuanjun Xia (Lawrenceville, NJ)

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

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Quick Facts

Patent No.: US 10,998,508
App. No.: 15/684,307
Granted: May 4, 2021
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 (312)

1. A composition comprising a first compound having the formula of M(L 1 ) x (L 2 ) y (L 3 ) z ;

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 is independently selected from the group consisting of:

wherein L 2 and L 3 are independently selected from the group of possible ligands for L 1 and

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 R a of L 1 is selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, and is directly bonded to an aromatic ring, and

wherein in the at least one R a of L 1 , any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

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 metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

4. The composition of claim 1 , wherein the metal is Ir or Pt.

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

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

7. The composition of claim 1 , wherein none of the at least one R a contain any CF 3 groups.

8. The composition of claim 1 , wherein the first compound does not have any F atoms other than in the at least one R a .

9. The composition of claim 1 , wherein the aromatic ring comprises LUMO electron density of the first compound.

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

11. The composition of claim 10 , wherein L 1 has the formula selected from the group consisting of:

and

wherein L 2 has the formula:

12. The composition of claim 11 , 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, sulfonyl, sulfonyl, phosphino, and combinations thereof.

13. The composition of claim 10 , wherein L 1 and L 2 are different and each independently selected from the group consisting of:

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

15. The composition of claim 1 , wherein L 1 is selected from the group consisting of:

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 ;

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 ;

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 ;

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 ,

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 ;

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 ;

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 ;

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 ;

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 ;

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 ;

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:

16. 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 is capable of functioning as a phosphorescent emitter at room temperature;

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

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 is independently selected from the group consisting of:

wherein L 1 and L 2 are independently selected from the group of possible ligands for L 1 and

wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein two adjacent substituents of R a , R b , R e , and R d are optionally joined to form a ring or form a multidentate ligand;

wherein in the at least one R a of L 1 , any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

17. The first device of claim 16 , wherein the organic layer further comprises a host; wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

18. The first device of claim 16 , wherein the organic layer further comprises a host, wherein the host material is selected from the group consisting of:

19. A consumer product comprising an 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 is capable of functioning as a phosphorescent emitter at room temperature;

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

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 is independently selected from the group consisting of:

wherein L 2 and L 3 are independently selected from the group of possible ligands for L 1 and

wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein in the at least one R a of L 1 , any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

20. The consumer product of claim 19 , wherein the consumer product is one of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a vehicle, a large area wall, a theater or stadium screen, and a sign.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2017

From: BOUDREAULT, PIERRE-LUC T.; YEAGER, WALTER; XIA, CHUANJUN

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 043373/0666 →

Continuity (3)

Continuation 15177906 · Jun 9, 2016

Continuation 14509274 · Oct 8, 2014

Related Publication 20170352821A1 · Dec 7, 2017