IP Library › Granted Patent US 10,411,201

Granted Patent B2

US 10,411,201 · App. 14/851,917 · Granted Sep 10, 2019

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

H01L51/0085 C07F15/0033 C09K11/025 C09K11/06 H01L51/0071 H01L51/0072 H01L51/0074 C09K2211/1029 C09K2211/1059 C09K2211/1088 C09K2211/185 H01L51/5016

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Quick Facts

Patent No.: US 10,411,201
App. No.: 14/851,917
Granted: Sep 10, 2019
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 is 0, 1, or 2; z is 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; R 3 represents mono, or di-substitution, or no substitution; R 2 , R C , and R D each independently represent mono, di, tri, or tetra-substitution, or no substitution; R 4 represents mono, di, tri, or tetra-substitution; at least one R 4 is a five-membered or six-membered heterocyclic ring which can be further substituted by R E ; where R E represents mono, di, tri, or tetra-substitution, or no substitution; each R substituent is independently selected from a variety of moieties; and any adjacent R substitutents are optionally joined to form a ring.

Claims (510)

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 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 an 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 triazine ring which is further substituted by R E ;

wherein R E represents mono or di-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 at least one R E is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, sulfanyl, sulfinyl, sulfonyl, phosphino, partially or fully deuterated variations thereof, 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

at least one of the following is true:

(i) at least one R E is selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variations thereof, partially or fully fluorinated variations thereof, and combinations thereof, and

(ii) exactly one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen.

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 ).

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

5. 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.

6. The compound of claim 1 , wherein exactly one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen.

7. The compound of claim 1 , wherein X is O or NR 1 .

8. The compound of claim 1 , wherein ring C is benzene, and ring D is pyridine.

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

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

11. The compound of claim 1 , where L C is selected from the group consisting of:

12. The compound of claim 1 , wherein R E is di-substituted.

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

L A185 through L A190 and L A193 through L A198 ,

each represented by the formula:

wherein in L A185 : X = O, R E = R A6 , R 2 = R B1 ,

in L A186 : X = O, R E = R A6 , R 2 = R B2 ,

in L A187 : X = O, R E = R A7 , R 2 = R B1 ,

in L A188 : X = O, R E = R A7 , R 2 = R B2 ,

in L A189 : X = O, R E = R A8 , R 2 = R B1 ,

in L A190 : X = O, R E = R A8 , R 2 = R B2 ,

in L A193 : X = S, R E = R A6 , R 2 = R B1 ,

in L A194 : X = S, R E = R A6 , R 2 = R B2 ,

in L A195 : X = S, R E = R A7 , R 2 = R B1 ,

in L A196 : X = S, R E = R A7 , R 2 = R B2 ,

in L A197 : X = S, R E = R A8 , R 2 = R B1 , and

in L A198 : X = S, R E = R A8 , R 2 = R B2 ,

L A201 through L A206 and L A209 through L A214 ,

each represented by the formula:

wherein in L A201 : X = O, R E = R A6 , R 2 = R B1 ,

in L A202 : X = O, R E = R A6 , R 2 = R B2 ,

in L A203 : X = O, R E = R A7 , R 2 = R B1 ,

in L A204 : X = O, R E = R A7 , R 2 = R B2 ,

in L A205 : X = O, R E = R A8 , R 2 = R B1 ,

in L A206 : X = O, R E = R A8 , R 2 = R B2 ,

in L A209 : X = S, R E = R A6 , R 2 = R B1 ,

in L A210 : X = S, R E = R A6 , R 2 = R B2 ,

in L A211 : X = S, R E = R A7 , R 2 = R B1 ,

in L A212 : X = S, R E = R A7 , R 2 = R B2 ,

in L A213 : X = S, R E = R A8 , R 2 = R B1 , and

in L A214 : X = S, R E = R A8 , R 2 = R B2 ,

L A217 through L A222 and L A225 through L A230 ,

each represented by the formula:

wherein 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 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 A233 through L A238 and L A241 through L A246 ,

each represented by the formula:

wherein 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 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 A249 through L A254 and L A257 through L A262 ,

each represented by the formula:

wherein in L A249 : X = O, R E = R A6 , R 2 = R B1 ,

in L A250 : X = O, R E = R A6 , R 2 = R B2 ,

in L A251 : X = O, R E = R A7 , R 2 = R B1 ,

in L A252 : X = O, R E = R A7 , R 2 = R B2 ,

in L A253 : X = O, R E = R A8 , R 2 = R B1 ,

in L A254 : X = O, R E = R A8 , R 2 = R B2 ,

in L A257 : X = S, R E = R A6 , R 2 = R B1 ,

in L A258 : X = S, R E = R A6 , R 2 = R B2 ,

in L A259 : X = S, R E = R A7 , R 2 = R B1 ,

in L A260 : X = S, R E = R A7 , R 2 = R B2 ,

in L A261 : X = S, R E = R A8 , R 2 = R B1 , and

in L A262 : X = S, R E = R A8 , R 2 = R B2 ,

L A265 through L A270 and L A273 through L A278 ,

each represented by the formula:

wherein in L A265 : X = O, R E = R A6 , R 2 = R B1 ,

in L A266 : X = O, R E = R A6 , R 2 = R B2 ,

in L A267 : X = O, R E = R A7 , R 2 = R B1 ,

in L A268 : X = O, R E = R A7 , R 2 = R B2 ,

in L A269 : X = O, R E = R A8 , R 2 = R B1 ,

in L A270 : X = O, R E = R A8 , R 2 = R B2 ,

in L A273 : X = S, R E = R A6 , R 2 = R B1 ,

in L A274 : X = S, R E = R A6 , R 2 = R B2 ,

in L A275 : X = S, R E = R A7 , R 2 = R B1 ,

in L A276 : X = S, R E = R A7 , R 2 = R B2 ,

in L A277 : X = S, R E = R A8 , R 2 = R B1 , and

in L A278 : X = S, R E = R A8 , R 2 = R B2 ,

L A281 through L A286 and L A289 through L A294 ,

each represented by the formula:

wherein 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 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 A297 through L A302 and L A306 through L A310 ,

each represented by the formula:

wherein 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 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 A313 through L A318 and L A321 through L A326 ,

each represented by the formula:

wherein 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 A6 , R 2 = R B2 , R 1 = R C1 ,

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 A329 through L A334 and L A337 through L A342 ,

each represented by the formula:

wherein 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 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 B2 , 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 A345 through L A350 and L A353 through L A358 ,

each represented by the formula:

wherein 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 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 A361 through L A366 and L A369 through L A374 ,

each represented by the formula:

wherein 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 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 A376 through L A378 and L A380 through L A382 ,

each represented by the formula:

wherein in L A376 : X = O, R E = R A6 ,

in L A377 : X = O, R E = R A7 ,

in L A378 : X = O, R E = R A8 ,

in L A380 : X = S, R E = R A6 ,

in L A381 : X = S, R E = R A7 , and

in L A382 : X = S, R E = R A8 ,

L A384 through L A386 and L A388 through L A390 ,

each represented by the formula::

wherein in L A384 : X = O, R E = R A6 ,

in L A385 : X = O, R E = R A7 ,

in L A386 : X = O, R E = R A8 ,

in L A388 : X = S, R E = R A8 ,

in L A389 : X = S, R E = R A7 , and

in L A390 : X = S, R E = R A8 ,

L A393 through L A398 and L A401 through L A406 ,

each represented by the formula:

wherein 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 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 A409 through L A414 and L A417 through L A422 ,

each represented by the formula:

wherein 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 A6 , 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 A425 through L A430 and L A433 through L A438 ,

each represented by the formula:

wherein 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 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 A441 through L A446 and L A449 through L A454 ,

each represented by the formula:

wherein 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 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 A456 through L A458 and L A460 through L A462 ,

each represented by the formula:

wherein in L A456 : X = O, R E = R A6 ,

in L A457 : X = O, R E = R A7 ,

in L A458 : X = O, R E = R A8 ,

in L A460 : X = S, R E = R A6 ,

in L A461 : X = S, R E = R A7 , and

in L A462 : X = S, R E = R A8 ,

L A464 through L A466 and L A468 through L A470 ,

each represented by the formula:

wherein in L A464 : X = O, R E = R A6 ,

in L A465 : X = O, R E = R A7 ,

in L A466 : X = O, R E = R A8 ,

in L A468 : X = S, R E = R A6 ,

in L A469 : X = S, R E = R A7 , and

in L A470 : X = S, R E = R A8 ,

L A472 through L A474 and L A476 through L A478 ,

each represented by the formula:

wherein 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 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 A480 through L A482 and L A484 through L A486 ,

each represented by the formula:

wherein 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 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 A488 through L A490 and L A492 through L A494 ,

each represented by the formula:

wherein 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 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 A496 through L A498 and L A500 through L A502 ,

each represented by the formula:

wherein 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 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 A505 through L A510 and L A513 through L A518 ,

each represented by the formula:

wherein in L A505 : X = O, R E = R A6 , R 2 = R B1 ,

in L A506 : X = O, R E = R A6 , R 2 = R B2 ,

in L A507 : X = O, R E = R A7 , R 2 = R B1 ,

in L A508 : X = O, R E = R A7 , R 2 = R B2 ,

in L A509 : X = O, R E = R A8 , R 2 = R B1 ,

in L A510 : X = O, R E = R A8 , R 2 = R B2 ,

in L A513 : X = S, R E = R A6 , R 2 = R B1 ,

in L A514 : X = S, R E = R A6 , R 2 = R B2 ,

in L A515 : X = S, R E = R A7 , R 2 = R B1 ,

in L A516 : X = S, R E = R A7 , R 2 = R B2 ,

in L A517 : X = S, R E = R A8 , R 2 = R B1 , and

in L A518 : X = S, R E = R A8 , R 2 = R B2 ,

L A521 through L A526 and L A529 through L A534 ,

each represented by the formula:

wherein in L A521 : X = O, R E = R A6 , R 2 = R B1 ,

in L A522 : X = O, R E = R A6 , R 2 = R B2 ,

in L A523 : X = O, R E = R A7 , R 2 = R B1 ,

in L A524 : X = O, R E = R A7 , R 2 = R B2 ,

in L A525 : X = O, R E = R A8 , R 2 = R B1 ,

in L A526 : X = O, R E = R A8 , R 2 = R B2 ,

in L A529 : X = S, R E = R A6 , R 2 = R B1 ,

in L A530 : X = S, R E = R A6 , R 2 = R B2 ,

in L A531 : X = S, R E = R A7 , R 2 = R B1 ,

in L A532 : X = S, R E = R A7 , R 2 = R B2 ,

in L A533 : X = S, R E = R A8 , R 2 = R B1 , and

in L A534 : X = S R E = R A8 , R 2 = R B2 ,

L A537 through L A542 and L A545 through L A550 ,

each represented by the formula:

wherein 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 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 A553 through L A558 and L A561 through L A566 ,

each represented by the formula:

wherein 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 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 A569 through L A574 and L A577 through L A582 ,

each represented by the formula:

wherein 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 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 A585 through L A590 and L A593 through L A598 ,

each represented by the formula:

wherein 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 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 A600 through L A602 and L A604 through L A606 ,

each represented by the formula:

wherein 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 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 A608 through L A610 and L A612 through L A614 ,

each represented by the formula:

wherein 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 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 A616 through L A618 and L A620 through L A622 ,

each represented by the formula:

wherein 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 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 A624 through L A626 and L A628 through L A630 ,

each represented by the formula:

wherein 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 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 , R1= R C2 ,

wherein R A6 to R A8 have the following structures:

wherein R B1 and R B2 have the following structures:

and

wherein R C1 to R C2 have the following structures:

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

wherein L Ak is selected from L A185 -L A190 , L A193 -L A198 , L A201 -L A206 , L A209 -L A214 , L A217 -L A222 , L A225 -L A230 , L A233 -L A238 , L A241 -L A246 , L A249 -L A254 , L A257 -L A262 , L A265 -L A270 , L A273 -L A278 , L A281 -L A286 , L A289 -L A294 , L A297 -L A302 , L A305 -L A310 , L A313 -L A318 , L A321 -L A326 , L A329 -L A334 , L A337 -L A342 , L A345 -L A350 , L A353 -L A358 , L A361 -L A366 , L A369 -L A374 , L A376 -L A378 , L A380 -L A382 , L A384 -L A386 , L A388 -L A390 , L A393 -L A398 , L A401 -L A408 , L A411 -L A414 , L A417 -L A422 , L A425 -L A430 , L A433 -L A438 , L A441 -L A446 , L A449 -L A454 , L A456 -L A458 , L A460 -L A462 , L A464 -L A466 , L A468 -L A470 , L A472 -L A474 , L A476 -L A478 , L A480 -L A482 , L A484 -L A486 , L A488 -L A490 , L A492 -L A494 , L A496 -L A498 , L A500 -L A502 , L A505 -L A510 , L A513 -L A518 , L A521 -L A526 , L A529 -L A534 , L A534 -L A542 , L A545 -L A550 , L A553 -L A558 , L A561 -L A566 , L A569 -L A574 , L A577 -L A582 , L A585 -L A590 , L A593 -L A598 , L A600 -L A602 , L A604 -L A606 , L A608 -L A610 , L A612 -L A614 , L A616 -L A618 , L A620 -L A622 , L A624 -L A626 , and L A628 -L A630 ; and

wherein L Bj is selected from L B1 through L B41 are defined as follows:

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

wherein L Ci is selected from L C1 through L C13 are defined as follows:

16. The compound of claim 1 , wherein each R E is independently selected from the group consisting of alkyl, cycloalkyl, partially and fully deuterated variations thereof, partially or fully fluorinated variations thereof, and combinations thereof.

17. 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 :

wherein the ligand L A is

wherein the ligand L B is

wherein the ligand L C is

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 an 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 triazine ring which is further substituted by R E ;

wherein R E represents mono or di-substitution;

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

at least one of the following is true:

(ii) exactly one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen.

18. The device of claim 17 , wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

19. The device of claim 17 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

20. The device of claim 17 , 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.

21. The device of claim 17 , wherein the organic layer further comprises a host and the host is selected from the group consisting of:

and combinations thereof.

22. A formulation comprising 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 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 an 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 triazine ring which is further substituted by R E ;

wherein R E represents mono or di-substitution;

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

at least one of the following is true:

(ii) exactly one of A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , and A 8 is nitrogen.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 14, 2015

From: BOUDREAULT, PIERRE-LUC T.; WENDT, HARVEY; XIA, CHUANJUN

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 036551/0496 →

Continuity (3)

Continuation In Part 14539412 · Nov 12, 2014

Provisional Application 62089397 · Dec 9, 2014

Related Publication 20160133860A1 · May 12, 2016

Cited By (3)

US 12,453,280 US 12,552,821 US 12,615,957