IP Library › Granted Patent US 10,844,085

Granted Patent B2

US 10,844,085 · App. 15/918,114 · Granted Nov 24, 2020

Organic electroluminescent materials and devices

Inventors: Zhiqiang Ji (Ewing, NJ); Jui-Yi Tsai (Newtown, PA); Lichang Zeng (Lawrenceville, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Walter Yeager (Yardley, PA); Eric Margulies (Ewing, NJ); Pierre-Luc T. Boudreault (Pennington, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

C07F15/0033 C09K11/06 H01L51/0085 H01L51/5016 H01L51/5056 H01L51/5072 C09K2211/1007 C09K2211/1014 C09K2211/1029 C09K2211/1033 C09K2211/1037 C09K2211/185 H01L51/0054 H01L51/0067 H01L51/0074 H01L2251/5384

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 10,844,085
App. No.: 15/918,114
Granted: Nov 24, 2020
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

A compound having the formula [L A ] 3-n Ir[L B ] n is disclosed. In the formula, L A is and L B is Formula I.

Claims (638)

1. A compound having the formula [L A ] 3-n Ir[L B ] n ;

wherein L A is

and wherein L B is

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;

wherein X 1 to X 6 are each independently carbon or nitrogen;

wherein each R and R′ 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 each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof;

wherein any adjacent substitutions on the same ring are optionally joined or fused into a ring; and

wherein n is 1 or 2.

2. The compound of claim 1 , wherein each R and R′ 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.

3. The compound of claim 1 , wherein X is O.

4. The compound of claim 1 , wherein X 1 to X 6 are carbon.

5. The compound of claim 1 , wherein X 1 is nitrogen, and X 2 to X 6 are carbon.

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

L A1 to L A3 having the

L A4 to L A6 having the

L A7 to L A9 having the

L A10 to L A12 having the

following structure,

wherein

in L A1 , X═O;

in L A4 , X═O;

in L A7 , X═O;

in L A10 , X═O;

in L A2 , X═S; and

in L A5 , X═S;

in L A8 , X═S;

in L A11 , X═S;

in L A3 , X═C(CH 3 ) 2 ;

in L A6 , X═C(CH 3 ) 2 ;

in L A9 , X═C(CH 3 ) 2 ;

in L A12 , X═C(CH 3 ) 2 ;

L A13 to L A15 having the

L A16 to L A18 having the

L A19 to L A21 having the

L A22 to L A24 having the

following structure,

wherein

in L A13 , X═O;

in L A16 , X═O;

in L A19 , X═O;

in L A22 , X═O;

in L A14 , X═S;

in L A17 , X═S;

in L A20 , X═S;

in L A23 , X═S;

in L A15 , X═C(CH 3 ) 2 ;

in L A18 , X═C(CH 3 ) 2 ;

in L A21 , X═C(CH 3 ) 2 ;

in L A24 , X═C(CH 3 ) 2 ;

L A25 to L A27 having the

L A28 to L A30 having the

L A31 to L A33 having the

L A34 to L A36 having the

following structure,

wherein

in L A25 , X═O;

in L A28 , X═O;

in L A31 , X═O;

in L A34 , X═O;

in L A26 , X═S;

in L A29 , X═S;

in L A32 , X═S;

in L A35 , X═S;

in L A27 , X═C(CH 3 ) 2 ;

in L A30 , X═C(CH 3 ) 2 ;

in L A33 , X═C(CH 3 ) 2 ;

in L A36 , X═C(CH 3 ) 2 ;

L A37 to L A39 having the

L A40 to L A42 having the

L A43 to L A45 having the

L A46 to L A48 having the

following structure,

wherein

in L A37 , X═O;

in L A40 , X═O;

in L A43 , X═O;

in L A46 , X═O;

in L A38 , X═S;

in L A41 , X═S;

in L A44 , X═S;

in L A47 , X═S;

in L A39 , X═C(CH 3 ) 2 ;

in L A42 , X═C(CH 3 ) 2 ;

in L A45 , X═C(CH 3 ) 2 ;

in L A48 , X═C(CH 3 ) 2 ;

L A49 to L A51 having the

L A52 to L A54 having the

L A55 to L A57 having the

L A58 to L A60 having the

following structure,

wherein

in L A49 , X═O;

in L A52 , X═O;

in L A55 , X═O;

in L A58 , X═O;

in L A50 , X═S;

in L A53 , X═S;

in L A56 , X═S;

in L A59 , X═S;

in L A51 , X═C(CH 3 ) 2 ;

in L A54 , X═C(CH 3 ) 2 ;

in L A57 , X═C(CH 3 ) 2 ;

in L A60 , X═C(CH 3 ) 2 ;

L A61 to L A63 having the

L A64 to L A66 having the

L A67 to L A69 having the

L A70 to L A72 having the

following structure,

wherein

in L A61 , X═O;

in L A64 , X═O;

in L A67 , X═O;

in L A70 , X═O;

in L A62 , X═S;

in L A65 , X═S;

in L A68 , X═S;

in L A71 , X═S;

in L A63 , X═C(CH 3 ) 2 ;

in L A66 , X═C(CH 3 ) 2 ;

in L A69 , X═C(CH 3 ) 2 ;

in L A72 , X═C(CH 3 ) 2 ;

L A73 to L A75 having the

L A76 to L A78 having the

L A79 to L A81 having the

L A82 to L A84 having the

following structure,

wherein

in L A73 , X═O;

in L A76 , X═O;

in L A79 , X═O;

in L A82 , X═O;

in L A74 , X═S;

in L A77 , X═S;

in L A80 , X═S;

in L A83 , X═S;

in L A75 , X═C(CH 3 ) 2 ;

in L A78 , X═C(CH 3 ) 2 ;

in L A81 , X═C(CH 3 ) 2 ;

in L A84 , X═C(CH 3 ) 2 ;

L A85 to L A87 having the

L A88 to L A90 having the

L A91 to L A93 having the

L A94 to L A96 having the

following structure,

wherein

in L A85 , X═O;

in L A88 , X═O;

in L A91 , X═O;

in L A94 , X═O;

in L A86 , X═S;

in L A89 , X═S;

in L A92 , X═S;

in L A95 , X═S;

in L A87 , X═C(CH 3 ) 2 ;

in L A90 , X═C(CH 3 ) 2 ;

in L A93 , X═C(CH 3 ) 2 ;

in L A96 , X═C(CH 3 ) 2 ;

L A97 to L A99 having the

L A100 to L A102 having the

L A103 to L A105 having the

L A106 to L A108 having the

following structure,

wherein

in L A97 , X═O;

in L A100 , X═O;

in L A103 , X═O;

in L A106 , X═O;

in L A98 , X═S;

in L A101 , X═S;

in L A104 , X═S;

in L A107 , X═S;

in L A99 , X═C(CH 3 ) 2 ;

in L A102 , X═C(CH 3 ) 2 ;

in L A105 , X═C(CH 3 ) 2 ;

in L A108 , X═C(CH 3 ) 2 ;

L A109 to L A111 having the

L A112 to L A114 having the

L A115 to L A117 having the

L A118 to L A120 having the

following structure,

wherein

in L A109 , X═O;

in L A112 , X═O;

in L A115 , X═O;

in L A118 , X═O;

in L A110 , X═S;

in L A113 , X═S;

in L A116 , X═S;

in L A119 , X═S;

in L A111 , X═C(CH 3 ) 2 ;

in L A114 , X═C(CH 3 ) 2 ;

in L A117 , X═C(CH 3 ) 2 ;

in L A120 , X═C(CH 3 ) 2 ;

L A121 to L A123 having the

L A124 to L A126 having the

L A127 to L A129 having the

L A130 to L A132 having the

following structure,

wherein

in L A121 , X═O;

in L A124 , X═O;

in L A127 , X═O;

in L A130 , X═O;

in L A122 , X═S;

in L A125 , X═S;

in L A128 , X═S;

in L A131 , X═S;

in L A123 , X═C(CH 3 ) 2 ;

in L A126 , X═C(CH 3 ) 2 ;

in L A129 , X═C(CH 3 ) 2 ;

in L A132 , X═C(CH 3 ) 2 ;

L A133 to L A135 having the

L A136 to L A138 having the

L A139 to L A141 having the

L A142 to L A144 having the

following structure,

wherein

in L A133 , X═O;

in L A136 , X═O;

in L A139 , X═O;

in L A142 , X═O;

in L A134 , X═S;

in L A137 , X═S;

in L A140 , X═S;

in L A143 , X═S;

in L A135 , X═C(CH 3 ) 2 ;

in L A138 , X═C(CH 3 ) 2 ;

in L A141 , X═C(CH 3 ) 2 ;

in L A144 , X═C(CH 3 ) 2 ;

L A145 to L A147 having the

L A148 to L A150 having the

L A151 to L A153 having the

L A154 to L A156 having the

following structure,

wherein

in L A145 , X═O;

in L A148 , X═O;

in L A151 , X═O;

in L A154 , X═O;

in L A146 , X═S;

in L A149 , X═S;

in L A152 , X═S;

in L A155 , X═S;

in L A147 , X═C(CH 3 ) 2 ;

in L A150 , X═C(CH 3 ) 2 ;

in L A153 , X═C(CH 3 ) 2 ;

in L A156 , X═C(CH 3 ) 2 ;

L A157 to L A159 having the

L A160 to L A162 having the

L A163 to L A165 having the

L A166 to L A168 having the

following structure,

wherein

in L A157 , X═O;

in L A160 , X═O;

in L A163 , X═O;

in L A166 , X═O;

in L A158 , X═S;

in L A161 , X═S;

in L A164 , X═S;

in L A167 , X═S;

in L A159 , X═C(CH 3 ) 2 ;

in L A162 , X═C(CH 3 ) 2 ;

in L A165 , X═C(CH 3 ) 2 ;

in L A168 , X═C(CH 3 ) 2 ;

L A169 to L A171 having the

L A172 to L A174 having the

L A175 to L A177 having the

L A178 to L A180 having the

following structure,

wherein

in L A169 , X═O;

in L A172 , X═O;

in L A175 , X═O;

in L A178 , X═O;

in L A170 , X═S;

in L A173 , X═S;

in L A176 , X═S;

in L A179 , X═S;

in L A171 , X═C(CH 3 ) 2 ;

in L A174 , X═C(CH 3 ) 2 ;

in L A177 , X═C(CH 3 ) 2 ;

in L A180 , X═C(CH 3 ) 2 ;

L A181 to L A183 having the

L A184 to L A186 having the

L A187 to L A189 having the

L A190 to L A192 having the

following structure,

wherein

in L A181 , X═O;

in L A184 , X═O;

in L A187 , X═O;

in L A190 , X═O;

in L A182 , X═S;

in L A185 , X═S;

in L A188 , X═S;

in L A191 , X═S;

in L A183 , X═C(CH 3 ) 2 ;

in L A186 , X═C(CH 3 ) 2 ;

in L A189 , X═C(CH 3 ) 2 ;

in L A192 , X═C(CH 3 ) 2 ;

L A193 to L A195 having the

L A196 to L A198 having the

L A199 to L A201 having the

L A202 to L A204 having the

following structure,

wherein

in L A193 , X═O;

in L A196 , X═O;

in L A199 , X═O;

in L A202 , X═O;

in L A194 , X═S;

in L A197 , X═S;

in L A200 , X═S;

in L A203 , X═S;

in L A195 , X═C(CH 3 ) 2 ;

in L A198 , X═C(CH 3 ) 2 ;

in L A201 , X═C(CH 3 ) 2 ;

in L A204 , X═C(CH 3 ) 2 ;

L A205 to L A207 having the

L A208 to L A210 having the

L A211 to L A213 having the

L A214 to L A216 having the

following structure,

wherein

in L A205 , X═O;

in L A208 , X═O;

in L A211 , X═O;

in L A214 , X═O;

in L A206 , X═S;

in L A209 , X═S;

in L A212 , X═S;

in L A215 , X═S;

in L A207 , X═C(CH 3 ) 2 ;

in L A210 , X═C(CH 3 ) 2 ;

in L A213 , X═C(CH 3 ) 2 ;

in L A216 , X═C(CH 3 ) 2 ;

L A217 to L A219 having the

L A220 to L A222 having the

L A223 to L A225 having the

L A226 to L A228 having the

following structure,

wherein

in L A217 , X═O;

in L A220 , X═O;

in L A223 , X═O;

in L A226 , X═O;

in L A218 , X═S;

in L A221 , X═S;

in L A224 , X═S;

in L A227 , X═S;

in L A219 , X═C(CH 3 ) 2 ;

in L A222 , X═C(CH 3 ) 2 ;

in L A225 , X═C(CH 3 ) 2 ;

in L A228 , X═C(CH 3 ) 2 ;

L A229 to L A231 having the

L A232 to L A234 having the

L A235 to L A237 having the

L A238 to L A240 having the

following structure,

wherein

in L A229 , X═O;

in L A232 , X═O;

in L A235 , X═O;

in L A238 , X═O;

in L A230 , X═S;

in L A233 , X═S;

in L A236 , X═S;

in L A239 , X═S;

in L A231 , X═C(CH 3 ) 2 ;

in L A234 , X═C(CH 3 ) 2 ;

in L A237 , X═C(CH 3 ) 2 ;

in L A240 , X═C(CH 3 ) 2 ;

L A241 to L A243 having the

L A244 to L A246 having the

L A247 to L A249 having the

L A250 to L A252 having the

following structure,

wherein

in L A241 , X═O;

in L A244 , X═O;

in L A247 , X═O;

in L A250 , X═O;

in L A242 , X═S;

in L A245 , X═S;

in L A248 , X═S;

in L A251 , X═S;

in L A243 , X═C(CH 3 ) 2 ;

in L A246 , X═C(CH 3 ) 2 ;

in L A249 , X═C(CH 3 ) 2 ;

in L A252 , X═C(CH 3 ) 2 ;

L A253 to L A255 having the

L A256 to L A258 having the

L A259 to L A261 having the

L A262 to L A264 having the

following structure,

wherein

in L A253 , X═O;

in L A256 , X═O;

in L A259 , X═O;

in L A262 , X═O;

in L A254 , X═S;

in L A257 , X═S;

in L A260 , X═S;

in L A263 , X═S;

in L A255 , X═C(CH 3 ) 2 ;

in L A258 , X═C(CH 3 ) 2 ;

in L A261 , X═C(CH 3 ) 2 ;

in L A264 , X═C(CH 3 ) 2 ;

L A265 to L A267 having the

L A268 to L A270 having the

L A271 to L A273 having the

L A274 to L A276 having the

following structure,

wherein

in L A265 , X═O;

in L A268 , X═O;

in L A271 , X═O;

in L A274 , X═O;

in L A266 , X═S;

in L A269 , X═S;

in L A272 , X═S;

in L A275 , X═S;

in L A267 , X═C(CH 3 ) 2 ;

in L A270 , X═C(CH 3 ) 2 ;

in L A273 , X═C(CH 3 ) 2 ;

in L A276 , X═C(CH 3 ) 2 ;

L A277 to L A279 having the

L A280 to L A282 having the

L A283 to L A285 having the

L A286 to L A288 having the

following structure,

wherein

in L A277 , X═O;

in L A280 , X═O;

in L A283 , X═O;

in L A286 , X═O;

in L A278 , X═S;

in L A281 , X═S;

in L A284 , X═S;

in L A287 , X═S;

in L A279 , X═C(CH 3 ) 2 ;

in L A282 , X═C(CH 3 ) 2 ;

in L A285 , X═C(CH 3 ) 2 ;

in L A288 , X═C(CH 3 ) 2 ;

L A289 to L A291 having the

L A292 to L A294 having the

following structure,

wherein

in L A289 , X═O;

in L A292 , X═O;

in L A290 , X═S;

in L A293 , X═S;

in L A291 , X═C(CH 3 ) 2 ; and

in L A294 , X═C(CH 3 ) 2 .

7. The compound of claim 1 , wherein L A is:

8. The compound of claim 1 , wherein L A is:

9. The compound of claim 6 , wherein L B is selected from the group consisting of:

wherein the compound is selected from the group consisting of Compound A-x having the formula Ir(L Ai )(L Bj ) 2 or the group consisting of Compound B-x having the formula Ir(L Ai ) 2 (L Bj ); wherein x=242i+j−242; wherein i is an integer from 1 to 294, and j is an integer from 1 to 242.

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

11. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula [L A ] 3-n Ir[L B ] n ;

wherein L A is

and wherein L B is

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;

wherein X 1 to X 6 are each independently carbon or nitrogen;

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof;

wherein any adjacent substitutions on the same ring are optionally joined or fused into a ring; and

wherein n is 1 or 2.

12. The OLED of claim 11 , wherein X is O.

13. The OLED of claim 11 , wherein X 1 to X 6 are carbon.

14. The OLED of claim 11 , wherein X 1 is nitrogen, and X 2 to X 6 are carbon.

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

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula [L A ] 3-n Ir[L B ] n ;

wherein L A is

and wherein L B is

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;

wherein X 1 to X 6 are each independently carbon or nitrogen;

wherein each R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof;

wherein any adjacent substitutions on the same ring are optionally joined or fused into a ring; and

wherein n is 1 or 2.

16. The consumer product of claim 15 , wherein the consumer product is one of a flat panel display, a curved display, a computer monitor, a medical monitor, OLEDs used in photodynamic therapy, near IR (NIR) OLEDs, 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 rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, or a sign.

Assignments (2)

NUNC PRO TUNC ASSIGNMENT Recorded Mar 12, 2018

From: JI, ZHIQIANG; TSAI, JUI-YI; ZENG, LICHANG; DYATKIN, ALEXEY BORISOVICH

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 045174/0435 →

NUNC PRO TUNC ASSIGNMENT Recorded Mar 12, 2018

From: YEAGER, WALTER; MARGULIES, ERIC; BOUDREAULT, PIERRE-LUC T.

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 045174/0562 →

Continuity (3)

Provisional Application 62479730 · Mar 31, 2017

Provisional Application 62478072 · Mar 29, 2017

Related Publication 20180282356A1 · Oct 4, 2018

Cited By (2)

US 12,247,041 US 12,453,280