US 12,139,501 B2
Organic electroluminescent materials and devices
Wei-Chun Shih, Lawrenceville, NJ (US); Hsiao-Fan Chen, Lawrence Township, NJ (US); Pierre-Luc T. Boudreault, Pennington, NJ (US); Bert Alleyne, Newtown, PA (US); and Zhiqiang Ji, Chalfont, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jul. 28, 2020, as Appl. No. 16/941,123.
Claims priority of provisional application 62/888,081, filed on Aug. 16, 2019.
Prior Publication US 2021/0047354 A1, Feb. 18, 2021
Int. Cl. C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC C07F 15/0033 (2013.01) [C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/6572 (2023.02); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 9 Claims
 
1. A compound having a formula of M(LA)x(LB)y(LC)z wherein LB and LC are each a bidentate ligand; and wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M;
wherein ligand LA has the structure of Formula I

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wherein:
A1 is CF3;
R1 is selected from the group consisting of alkyl, cycloalkyl, fluorine, and combinations thereof;
R2 is and does not comprise fluorine;
R3, R4, and R5 are each independently a hydrogen or a substituent selected from the group consisting of deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, fluorine, and combinations thereof;
one of R3, R4, or R5 is fluorine;
A1 and R1 are different;
R6 is hydrogen, alkyl, or cycloalkyl; and
wherein one of the following is true:
R5 is fluorine and R1, R3, and R4 are each alkyl; or
R5 is CF3;
wherein the ligand LA is coordinated to a metal M;
wherein the metal M can be coordinated to other ligands;
wherein M is Ir;
wherein the ligand LA can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein two of R3, R4, or R5 can be joined or fused together to form a ring;
wherein ligand LB is selected from the group consisting of:

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wherein j′ is an integer from 1 to 400, and for each LBj′, the substituents RE and G are defined as follows:
 
 
 
Ligand RE G
 
 
 
LB1 R1 G1
 
LB2 R2 G1
 
LB3 R3 G1
 
LB4 R4 G1
 
LB5 R5 G1
 
LB6 R6 G1
 
LB7 R7 G1
 
LB8 R8 G1
 
LB9 R9 G1
 
LB10 R10 G1
 
LB11 R11 G1
 
LB12 R12 G1
 
LB13 R13 G1
 
LB14 R14 G1
 
LB15 R15 G1
 
LB16 R16 G1
 
LB17 R17 G1
 
LB18 R18 G1
 
LB19 R19 G1
 
LB20 R20 G1
 
LB21 R1 G2
 
LB22 R2 G2
 
LB23 R3 G2
 
LB24 R4 G2
 
LB25 R5 G2
 
LB26 R6 G2
 
LB27 R7 G2
 
LB28 R8 G2
 
LB29 R9 G2
 
LB30 R10 G2
 
LB31 R11 G2
 
LB32 R12 G2
 
LB33 R13 G2
 
LB34 R14 G2
 
LB35 R15 G2
 
LB36 R16 G2
 
LB37 R17 G2
 
LB38 R18 G2
 
LB39 R19 G2
 
LB40 R20 G2
 
LB41 R1 G3
 
LB42 R2 G3
 
LB43 R3 G3
 
LB44 R4 G3
 
LB45 R5 G3
 
LB46 R6 G3
 
LB47 R7 G3
 
LB48 R8 G3
 
LB49 R9 G3
 
LB50 R10 G3
 
LB51 R11 G3
 
LB52 R12 G3
 
LB53 R13 G3
 
LB54 R14 G3
 
LB55 R15 G3
 
LB56 R16 G3
 
LB57 R17 G3
 
LB58 R18 G3
 
LB59 R19 G3
 
LB60 R20 G3
 
LB61 R1 G4
 
LB62 R2 G4
 
LB63 R3 G4
 
LB64 R4 G4
 
LB65 R5 G4
 
LB66 R6 G4
 
LB67 R7 G4
 
LB68 R8 G4
 
LB69 R9 G4
 
LB70 R10 G4
 
LB71 R11 G4
 
LB72 R12 G4
 
LB73 R13 G4
 
LB74 R14 G4
 
LB75 R15 G4
 
LB76 R16 G4
 
LB77 R17 G4
 
LB78 R18 G4
 
LB79 R19 G4
 
LB80 R20 G4
 
LB81 R1 G5
 
LB82 R2 G5
 
LB83 R3 G5
 
LB84 R4 G5
 
LB85 R5 G5
 
LB86 R6 G5
 
LB87 R7 G5
 
LB88 R8 G5
 
LB89 R9 G5
 
LB90 R10 G5
 
LB91 R11 G5
 
LB92 R12 G5
 
LB93 R13 G5
 
LB94 R14 G5
 
LB95 R15 G5
 
LB96 R16 G5
 
LB97 R17 G5
 
LB98 R18 G5
 
LB99 R19 G5
 
LB100 R20 G5
 
LB101 R1 G6
 
LB102 R2 G6
 
LB103 R3 G6
 
LB104 R4 G6
 
LB105 R5 G6
 
LB106 R6 G6
 
LB107 R7 G6
 
LB108 R8 G6
 
LB109 R9 G6
 
LB110 R10 G6
 
LB111 R11 G6
 
LB112 R12 G6
 
LB113 R13 G6
 
LB114 R14 G6
 
LB115 R15 G6
 
LB116 R16 G6
 
LB117 R17 G6
 
LB118 R18 G6
 
LB119 R19 G6
 
LB120 R20 G6
 
LB121 R1 G7
 
LB122 R2 G7
 
LB123 R3 G7
 
LB124 R4 G7
 
LB125 R5 G7
 
LB126 R6 G7
 
LB127 R7 G7
 
LB128 R8 G7
 
LB129 R9 G7
 
LB130 R10 G7
 
LB131 R11 G7
 
LB132 R12 G7
 
LB133 R13 G7
 
LB134 R14 G7
 
LB135 R15 G7
 
LB136 R16 G7
 
LB137 R17 G7
 
LB138 R18 G7
 
LB139 R19 G7
 
LB140 R20 G7
 
LB141 R1 G8
 
LB142 R2 G8
 
LB143 R3 G8
 
LB144 R4 G8
 
LB145 R5 G8
 
LB146 R6 G8
 
LB147 R7 G8
 
LB148 R8 G8
 
LB149 R9 G8
 
LB150 R10 G8
 
LB151 R11 G8
 
LB152 R12 G8
 
LB153 R13 G8
 
LB154 R14 G8
 
LB155 R15 G8
 
LB156 R16 G8
 
LB157 R17 G8
 
LB158 R18 G8
 
LB159 R19 G8
 
LB160 R20 G8
 
LB161 R1 G9
 
LB162 R2 G9
 
LB163 R3 G9
 
LB164 R4 G9
 
LB165 R5 G9
 
LB166 R6 G9
 
LB167 R7 G9
 
LB168 R8 G9
 
LB169 R9 G9
 
LB170 R10 G9
 
LB171 R11 G9
 
LB172 R12 G9
 
LB173 R13 G9
 
LB174 R14 G9
 
LB175 R15 G9
 
LB176 R16 G9
 
LB177 R17 G9
 
LB178 R18 G9
 
LB179 R19 G9
 
LB180 R20 G9
 
LB181 R1 G10
 
LB182 R2 G10
 
LB183 R3 G10
 
LB184 R4 G10
 
LB185 R5 G10
 
LB186 R6 G10
 
LB187 R7 G10
 
LB188 R8 G10
 
LB189 R9 G10
 
LB190 R10 G10
 
LB191 R11 G10
 
LB192 R12 G10
 
LB193 R13 G10
 
LB194 R14 G10
 
LB195 R15 G10
 
LB196 R16 G10
 
LB197 R17 G10
 
LB198 R18 G10
 
LB199 R19 G10
 
LB200 R20 G10
 
LB201 R1 G11
 
LB202 R2 G11
 
LB203 R3 G11
 
LB204 R4 G11
 
LB205 R5 G11
 
LB206 R6 G11
 
LB207 R7 G11
 
LB208 R8 G11
 
LB209 R9 G11
 
LB210 R10 G11
 
LB211 R11 G11
 
LB212 R12 G11
 
LB213 R13 G11
 
LB214 R14 G11
 
LB215 R15 G11
 
LB216 R16 G11
 
LB217 R17 G11
 
LB218 R18 G11
 
LB219 R19 G11
 
LB220 R20 G11
 
LB221 R1 G12
 
LB222 R2 G12
 
LB223 R3 G12
 
LB224 R4 G12
 
LB225 R5 G12
 
LB226 R6 G12
 
LB227 R7 G12
 
LB228 R8 G12
 
LB229 R9 G12
 
LB230 R10 G12
 
LB231 R11 G12
 
LB232 R12 G12
 
LB233 R13 G12
 
LB234 R14 G12
 
LB235 R15 G12
 
LB236 R16 G12
 
LB237 R17 G12
 
LB238 R18 G12
 
LB239 R19 G12
 
LB240 R20 G12
 
LB241 R1 G13
 
LB242 R2 G13
 
LB243 R3 G13
 
LB244 R4 G13
 
LB245 R5 G13
 
LB246 R6 G13
 
LB247 R7 G13
 
LB248 R8 G13
 
LB249 R9 G13
 
LB250 R10 G13
 
LB251 R11 G13
 
LB252 R12 G13
 
LB253 R13 G13
 
LB254 R14 G13
 
LB255 R15 G13
 
LB256 R16 G13
 
LB257 R17 G13
 
LB258 R18 G13
 
LB259 R19 G13
 
LB260 R20 G13
 
LB261 R1 G14
 
LB262 R2 G14
 
LB263 R3 G14
 
LB264 R4 G14
 
LB265 R5 G14
 
LB266 R6 G14
 
LB267 R7 G14
 
LB268 R8 G14
 
LB269 R9 G14
 
LB270 R10 G14
 
LB271 R11 G14
 
LB272 R12 G14
 
LB273 R13 G14
 
LB274 R14 G14
 
LB275 R15 G14
 
LB276 R16 G14
 
LB277 R17 G14
 
LB278 R18 G14
 
LB279 R19 G14
 
LB280 R20 G14
 
LB281 R1 G15
 
LB282 R2 G15
 
LB283 R3 G15
 
LB284 R4 G15
 
LB285 R5 G15
 
LB286 R6 G15
 
LB287 R7 G15
 
LB288 R8 G15
 
LB289 R9 G15
 
LB290 R10 G15
 
LB291 R11 G15
 
LB292 R12 G15
 
LB293 R13 G15
 
LB294 R14 G15
 
LB295 R15 G15
 
LB296 R16 G15
 
LB297 R17 G15
 
LB298 R18 G15
 
LB299 R19 G15
 
LB300 R20 G15
 
LB301 R1 G16
 
LB302 R2 G16
 
LB303 R3 G16
 
LB304 R4 G16
 
LB305 R5 G16
 
LB306 R6 G16
 
LB307 R7 G16
 
LB308 R8 G16
 
LB309 R9 G16
 
LB310 R10 G16
 
LB311 R11 G16
 
LB312 R12 G16
 
LB313 R13 G16
 
LB314 R14 G16
 
LB315 R15 G16
 
LB316 R16 G16
 
LB317 R17 G16
 
LB318 R18 G16
 
LB319 R19 G16
 
LB320 R20 G16
 
LB321 R1 G17
 
LB322 R2 G17
 
LB323 R3 G17
 
LB324 R4 G17
 
LB325 R5 G17
 
LB326 R6 G17
 
LB327 R7 G17
 
LB328 R8 G17
 
LB329 R9 G17
 
LB330 R10 G17
 
LB331 R11 G17
 
LB332 R12 G17
 
LB333 R13 G17
 
LB334 R14 G17
 
LB335 R15 G17
 
LB336 R16 G17
 
LB337 R17 G17
 
LB338 R18 G17
 
LB339 R19 G17
 
LB340 R20 G17
 
LB341 R1 G18
 
LB342 R2 G18
 
LB343 R3 G18
 
LB344 R4 G18
 
LB345 R5 G18
 
LB346 R6 G18
 
LB347 R7 G18
 
LB348 R8 G18
 
LB349 R9 G18
 
LB350 R10 G18
 
LB351 R11 G18
 
LB352 R12 G18
 
LB353 R13 G18
 
LB354 R14 G18
 
LB355 R15 G18
 
LB356 R16 G18
 
LB357 R17 G18
 
LB358 R18 G18
 
LB359 R19 G18
 
LB360 R20 G18
 
LB361 R1 G19
 
LB362 R2 G19
 
LB363 R3 G19
 
LB364 R4 G19
 
LB365 R5 G19
 
LB366 R6 G19
 
LB367 R7 G19
 
LB368 R8 G19
 
LB369 R9 G19
 
LB370 R10 G19
 
LB371 R11 G19
 
LB372 R12 G19
 
LB373 R13 G19
 
LB374 R14 G19
 
LB375 R15 G19
 
LB376 R16 G19
 
LB377 R17 G19
 
LB378 R18 G19
 
LB379 R19 G19
 
LB380 R20 G19
 
LB381 R1 G20
 
LB382 R2 G20
 
LB383 R3 G20
 
LB384 R4 G20
 
LB385 R5 G20
 
LB386 R6 G20
 
LB387 R7 G20
 
LB388 R8 G20
 
LB389 R9 G20
 
LB390 R10 G20
 
LB391 R11 G20
 
LB392 R12 G20
 
LB393 R13 G20
 
LB394 R14 G20
 
LB395 R15 G20
 
LB396 R16 G20
 
LB397 R17 G20
 
LB398 R18 G20
 
LB399 R19 G20
 
LB400 R20 G20
 
 
wherein R1 to R20 have the following structures:

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and
wherein G1 to G20 have the following structures

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wherein when ligand LB has the structure LBj′-7 based on

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RE is selected from the
group consisting of

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wherein ligand LC is selected from the group consisting of:

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wherein: each Y1 to Y13 are independently selected from the group consisting of carbon and nitrogen;
Y′ is selected from the group consisting of B Re, N Re, P Re, O, S, Se, C=O, S=O, SO2, CReRf, SiReRf, and GeReRf′; wherein Re and Rf can be fused or joined to form a ring;
each Ra, Rb, Rc, and Rd independently represents from mono substitution to the maximum possible number of substitutions, or no substitution;
each Ra, Rb, Rc, Rd, Re and Rf is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two adjacent substituents of Ra, Rb, Rc, and Rd can be fused or joined to form a ring or form a multidentate ligand.