IP Library Granted Patent US 9,929,360
Granted Patent B2
US 9,929,360 · App. 15/587,993 · Granted Mar 27, 2018

Organic electroluminescent materials and devices

Inventors: Pierre-Luc T. Boudreault (Pennington, NJ); Bert Alleyne (Newtown, PA); Chuanjun Xia (Lawrenceville, NJ)
Assignee: Universal Display Corporation
H01L51/0085C07F15/0033C09K11/025C09K11/06C09K2211/1007C09K2211/1051C09K2211/185H01L51/506H01L51/5016H01L51/5076H01L51/5092H01L51/5096
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Quick Facts
Patent No.
US 9,929,360
App. No.
15/587,993
Granted
Mar 27, 2018
Kind
B2
Abstract

New phosphorescent metal complexes containing substituents with succinimide moiety that are useful for phosphorescent organic light emitting devices are disclosed.

Claims (382)

1. A compound comprising a first ligand L A having a formula:

wherein rings A and B are each a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R A and R B each independently represent mono to the possible maximum number of substitution, or no substitution;

wherein Z 1 and Z 2 are each independently selected from the group consisting of carbon or nitrogen;

wherein R A and R B are each 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 any adjacent substituents are optionally joined or fused into a ring;

wherein (1) at least one R A comprises an aromatic group further fused by a first group; or (2) two adjacent R A s form a first group fused to ring A;

wherein the first group is selected from the group consisting of:

wherein R is 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 the ligand L A is coordinated to a metal M;

wherein the metal M can be coordinated to other ligands; and

wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.

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 Z 1 is a neutral donor atom.

4. The compound of claim 1 , wherein at least one R A comprises an aromatic group further fused by a first group.

5. The compound of claim 1 , wherein two adjacent R A s form a first group fused to ring A.

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

wherein X is selected from the group consisting of O, S, Se, C, Si, and N.

7. The compound of claim 1 , wherein the first group is selected from the group consisting of:

8. The compound of claim 6 , wherein the ligand L A is

wherein (1) at least one R A comprises a phenyl ring further fused by a first group; or (2) two adjacent R A s form a first group fused to the pyridine ring.

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

L A1 through L A15

L A16 through L A30

having the following structure

having the following structure

wherein L A1 : R 1 = CH 3 and R 2 = H

wherein in L A16 : R 1 = CH 3 and R 2 = H

L A2 : R 1 = CD 3 and R 2 = H

L A17 : R 1 = CD 3 and R 2 = H

L A3 : R 1 = i-propyl and R 2 = H

L A18 : R 1 = i-propyl and R 2 = H

L A4 : R 1 = i-butyl and R 2 = H

L A19 : R 1 = i-butyl and R 2 = H

L A5 : R 1 = cyclopentyl and R 2 = H

L A20 : R 1 = cyclopentyl and R 2 = H

L A6 : R 1 = CH 3 and R 2 = CH 3

L A21 : R 1 = CH 3 and R 2 = CH 3

L A7 : R 1 = CD 3 and R 2 = CH 3

L A22 : R 1 = CD 3 and R 2 = CH 3

L A8 : R 1 = i-propyl and R 2 = CH 3

L A23 : R 1 = i-propyl and R 2 = CH 3

L A9 : R 1 = i-butyl and R 2 = CH 3

L A24 : R 1 = i-butyl and R 2 = CH 3

L A10 : R 1 = cyclopentyl and R 3 = CH 3

L A25 : R 1 = cyclopentyl and R 3 = CH 3

L A11 : R 1 = CH 3 and R 2 = CD 3

L A26 : R 1 = CH 3 and R 2 = CD 3

L A12 : R 1 = CD 3 and R 2 = CD 3

L A27 : R 1 = CD 3 and R 2 = CD 3

L A13 : R 1 = i-propyl and R 2 = CD 3

L A28 : R 1 = i-propyl and R 2 = CD 3

L A14 : R 1 = i-butyl and R 2 = CD 3

L A29 : R 1 = i-butyl and R 2 = CD 3

L A15 : R 1 = cyclopentyl and R 3 = CD 3 ,

L A30 : R 1 = cyclopentyl and R 3 = CD 3 ,

L A31 through L A45

L A46 through L A60

having the following structure

having the following structure

wherein L A31 : R 1 = CH 3 and R 2 = H

wherein in L A46 : R 1 = CH 3 and R 2 = H

L A32 : R 1 = CD 3 and R 2 = H

L A47 : R 1 = CD 3 and R 2 = H

L A33 : R 1 = i-propyl and R 2 = H

L A48 : R 1 = i-propyl and R 2 = H

L A34 : R 1 = i-butyl and R 2 = H

L A49 : R 1 = i-butyl and R 2 = H

L A35 : R 1 = cyclopentyl and R 2 = H

L A50 : R 1 = cyclopentyl and R 2 = H

L A36 : R 1 = CH 3 and R 2 = CH 3

L A51 : R 1 = CH 3 and R 2 = CH 3

L A37 : R 1 = CD 3 and R 2 = CH 3

L A52 : R 1 = CD 3 and R 2 = CH 3

L A38 : R 1 = i-propyl and R 2 = CH 3

L A53 : R 1 = i-propyl and R 2 = CH 3

L A39 : R 1 = i-butyl and R 2 = CH 3

L A54 : R 1 = i-butyl and R 2 = CH 3

L A40 : R 1 = cyclopentyl and R 3 = CH 3

L A55 : R 1 = cyclopentyl and R 3 = CH 3

L A41 : R 1 = CH 3 and R 2 = CD 3

L A56 : R 1 = CH 3 and R 2 = CD 3

L A42 : R 1 = CD 3 and R 2 = CD 3

L A57 : R 1 = CD 3 and R 2 = CD 3

L A43 : R 1 = i-propyl and R 2 = CD 3

L A58 : R 1 = i-propyl and R 2 = CD 3

L A44 : R 1 = i-butyl and R 2 = CD 3

L A59 : R 1 = i-butyl and R 2 = CD 3

L A45 : R 1 = cyclopentyl and R 3 = CD 3 ,

L A60 : R 1 = cyclopentyl and R 3 = CD 3 ,

L A61 through L A75

L A76 through L A90

having the following structure

having the following structure

wherein L A61 : R 1 = CH 3 and R 2 = H

wherein in L A76 : R 1 = CH 3 and R 2 = H

L A62 : R 1 = CD 3 and R 2 = H

L A77 : R 1 = CD 3 and R 2 = H

L A63 : R 1 = i-propyl and R 2 = H

L A78 : R 1 = i-propyl and R 2 = H

L A64 : R 1 = i-butyl and R 2 = H

L A79 : R 1 = i-butyl and R 2 = H

L A65 : R 1 = cyclopentyl and R 2 = H

L A80 : R 1 = cyclopentyl and R 2 = H

L A66 : R 1 = CH 3 and R 2 = CH 3

L A81 : R 1 = CH 3 and R 2 = CH 3

L A67 : R 1 = CD 3 and R 2 = CH 3

L A82 : R 1 = CD 3 and R 2 = CH 3

L A68 : R 1 = i-propyl and R 2 = CH 3

L A83 : R 1 = i-propyl and R 2 = CH 3

L A69 : R 1 = i-butyl and R 2 = CH 3

L A84 : R 1 = i-butyl and R 2 = CH 3

L A70 : R 1 = cyclopentyl and R 3 = CH 3

L A85 : R 1 = cyclopentyl and R 3 = CH 3

L A71 : R 1 = CH 3 and R 2 = CD 3

L A86 : R 1 = CH 3 and R 2 = CD 3

L A72 : R 1 = CD 3 and R 2 = CD 3

L A87 : R 1 = CD 3 and R 2 = CD 3

L A73 : R 1 = i-propyl and R 2 = CD 3

L A88 : R 1 = i-propyl and R 2 = CD 3

L A74 : R 1 = i-butyl and R 2 = CD 3

L A89 : R 1 = i-butyl and R 2 = CD 3

L A75 : R 1 = cyclopentyl and R 3 = CD 3 ,

L A90 : R 1 = cyclopentyl and R 3 = CD 3 ,

L A91 through L A105

L A106 through L A120

having the following structure

having the following structure

wherein L A91 : Y 1 = S and R 2 = H

wherein L A106 : Y 1 = S and R 2 = H

L A92 : Y 1 = O and R 2 = H

L A107 : Y 1 = O and R 2 = H

L A93 : Y 1 = Se and R 2 = H

L A108 : Y 1 = Se and R 2 = H

L A94 : Y 1 = N(CH 3 ) and R 2 = H

L A109 : Y 1 = N(CH 3 ) and R 2 = H

L A95 : Y 1 = N(i-propyl) and R 2 = H

L A110 : Y 1 = N(i-propyl) and R 2 = H

L A96 : Y 1 = S and R 2 = CH 3

L A111 : Y 1 = S and R 2 = CH 3

L A97 : Y 1 = O and R 2 = CH 3

L A112 : Y 1 = O and R 2 = CH 3

L A98 : Y 1 = Se and R 2 = CH 3

L A113 : Y 1 = Se and R 2 = CH 3

L A99 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A114 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A100 : Y 1 = N(i-propyl) and R 2 = CH 3

L A115 : Y 1 = N(i-propyl) and R 2 = CH 3

L A101 : Y 1 = S and R 2 = CD 3

L A116 : Y 1 = S and R 2 = CD 3

L A102 : Y 1 = O and R 2 = CD 3

L A117 : Y 1 = O and R 2 = CD 3

L A103 : Y 1 = Se and R 2 = CD 3

L A118 : Y 1 = Se and R 2 = CD 3

L A104 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A119 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A105 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A120 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A121 through L A135

L A136 through L A150

having the following structure

having the following structure

wherein L A121 : Y 1 = S and R 2 = H

wherein L A136 : Y 1 = S and R 2 = H

L A122 : Y 1 = O and R 2 = H

L A137 : Y 1 = O and R 2 = H

L A123 : Y 1 = Se and R 2 = H

L A138 : Y 1 = Se and R 2 = H

L A124 : Y 1 = N(CH 3 ) and R 2 = H

L A139 : Y 1 = N(CH 3 ) and R 2 = H

L A125 : Y 1 = N(i-propyl) and R 2 = H

L A140 : Y 1 = N(i-propyl) and R 2 = H

L A126 : Y 1 = S and R 2 = CH 3

L A141 : Y 1 = S and R 2 = CH 3

L A127 : Y 1 = O and R 2 = CH 3

L A142 : Y 1 = O and R 2 = CH 3

L A128 : Y 1 = Se and R 2 = CH 3

L A143 : Y 1 = Se and R 2 = CH 3

L A129 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A144 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A130 : Y 1 = N(i-propyl) and R 2 = CH 3

L A145 : Y 1 = N(i-propyl) and R 2 = CH 3

L A131 : Y 1 = S and R 2 = CD 3

L A146 : Y 1 = S and R 2 = CD 3

L A132 : Y 1 = O and R 2 = CD 3

L A147 : Y 1 = O and R 2 = CD 3

L A133 : Y 1 = Se and R 2 = CD 3

L A148 : Y 1 = Se and R 2 = CD 3

L A134 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A149 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A135 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A150 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A151 through L A165

L A166 through L A180

having the following structure

having the following structure

wherein L A151 : Y 1 = S and R 2 = H

wherein L A166 : Y 1 = S and R 2 = H

L A152 : Y 1 = O and R 2 = H

L A167 : Y 1 = O and R 2 = H

L A153 : Y 1 = Se and R 2 = H

L A168 : Y 1 = Se and R 2 = H

L A154 : Y 1 = N(CH 3 ) and R 2 = H

L A169 : Y 1 = N(CH 3 ) and R 2 = H

L A155 : Y 1 = N(i-propyl) and R 2 = H

L A170 : Y 1 = N(i-propyl) and R 2 = H

L A156 : Y 1 = S and R 2 = CH 3

L A171 : Y 1 = S and R 2 = CH 3

L A157 : Y 1 = O and R 2 = CH 3

L A172 : Y 1 = O and R 2 = CH 3

L A158 : Y 1 = Se and R 2 = CH 3

L A173 : Y 1 = Se and R 2 = CH 3

L A159 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A174 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A160 : Y 1 = N(i-propyl) and R 2 = CH 3

L A175 : Y 1 = N(i-propyl) and R 2 = CH 3

L A161 : Y 1 = S and R 2 = CD 3

L A176 : Y 1 = S and R 2 = CD 3

L A162 : Y 1 = O and R 2 = CD 3

L A177 : Y 1 = O and R 2 = CD 3

L A163 : Y 1 = Se and R 2 = CD 3

L A178 : Y 1 = Se and R 2 = CD 3

L A164 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A179 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A165 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A180 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A181 through L A195

L A196 through L A210

having the following structure

having the following structure

wherein L A181 : Y 1 = S and R 2 = H

wherein L A196 : Y 1 = S and R 2 = H

L A182 : Y 1 = O and R 2 = H

L A197 : Y 1 = O and R 2 = H

L A183 : Y 1 = Se and R 2 = H

L A198 : Y 1 = Se and R 2 = H

L A184 : Y 1 = N(CH 3 ) and R 2 = H

L A199 : Y 1 = N(CH 3 ) and R 2 = H

L A185 : Y 1 = N(i-propyl) and R 2 = H

L A200 : Y 1 = N(i-propyl) and R 2 = H

L A186 : Y 1 = S and R 2 = CH 3

L A201 : Y 1 = S and R 2 = CH 3

L A187 : Y 1 = O and R 2 = CH 3

L A202 : Y 1 = O and R 2 = CH 3

L A188 : Y 1 = Se and R 2 = CH 3

L A203 : Y 1 = Se and R 2 = CH 3

L A189 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A204 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A190 : Y 1 = N(i-propyl) and R 2 = CH 3

L A205 : Y 1 = N(i-propyl) and R 2 = CH 3

L A191 : Y 1 = S and R 2 = CD 3

L A206 : Y 1 = S and R 2 = CD 3

L A192 : Y 1 = O and R 2 = CD 3

L A207 : Y 1 = O and R 2 = CD 3

L A193 : Y 1 = Se and R 2 = CD 3

L A208 : Y 1 = Se and R 2 = CD 3

L A194 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A209 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A195 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A210 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A211 through L A225

L A226 through L A240

having the following structure

having the following structure

wherein L A211 : Y 1 = S and R 2 = H

wherein L A226 : Y 1 = S and R 2 = H

L A212 : Y 1 = O and R 2 = H

L A227 : Y 1 = O and R 2 = H

L A213 : Y 1 = Se and R 2 = H

L A228 : Y 1 = Se and R 2 = H

L A214 : Y 1 = N(CH 3 ) and R 2 = H

L A229 : Y 1 = N(CH 3 ) and R 2 = H

L A215 : Y 1 = N(i-propyl) and R 2 = H

L A230 : Y 1 = N(i-propyl) and R 2 = H

L A216 : Y 1 = S and R 2 = CH 3

L A231 : Y 1 = S and R 2 = CH 3

L A217 : Y 1 = O and R 2 = CH 3

L A232 : Y 1 = O and R 2 = CH 3

L A218 : Y 1 = Se and R 2 = CH 3

L A233 : Y 1 = Se and R 2 = CH 3

L A219 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A234 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A220 : Y 1 = N(i-propyl) and R 2 = CH 3

L A235 : Y 1 = N(i-propyl) and R 2 = CH 3

L A221 : Y 1 = S and R 2 = CD 3

L A236 : Y 1 = S and R 2 = CD 3

L A222 : Y 1 = O and R 2 = CD 3

L A237 : Y 1 = O and R 2 = CD 3

L A223 : Y 1 = Se and R 2 = CD 3

L A238 : Y 1 = Se and R 2 = CD 3

L A224 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A239 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A225 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A240 : Y 1 = N(i-propyl) and R 2 = CD 3 ,

L A241 through L A255

L A256 through L A270

having the following structure

having the following structure

wherein L A241 : Y 1 = S and R 2 = H

wherein L A256 : Y 1 = S and R 2 = H

L A242 : Y 1 = O and R 2 = H

L A257 : Y 1 = O and R 2 = H

L A243 : Y 1 = Se and R 2 = H

L A258 : Y 1 = Se and R 2 = H

L A244 : Y 1 = N(CH 3 ) and R 2 = H

L A259 : Y 1 = N(CH 3 ) and R 2 = H

L A245 : Y 1 = N(i-propyl) and R 2 = H

L A260 : Y 1 = N(i-propyl) and R 2 = H

L A246 : Y 1 = S and R 2 = CH 3

L A261 : Y 1 = S and R 2 = CH 3

L A247 : Y 1 = O and R 2 = CH 3

L A262 : Y 1 = O and R 2 = CH 3

L A248 : Y 1 = Se and R 2 = CH 3

L A263 : Y 1 = Se and R 2 = CH 3

L A249 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A264 : Y 1 = N(CH 3 ) and R 2 = CH 3

L A250 : Y 1 = N(i-propyl) and R 2 = CH 3

L A265 : Y 1 = N(i-propyl) and R 2 = CH 3

L A251 : Y 1 = S and R 2 = CD 3

L A266 : Y 1 = S and R 2 = CD 3

L A252 : Y 1 = O and R 2 = CD 3

L A267 : Y 1 = O and R 2 = CD 3

L A253 : Y 1 = Se and R 2 = CD 3

L A268 : Y 1 = Se and R 2 = CD 3

L A254 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A269 : Y 1 = N(CH 3 ) and R 2 = CD 3

L A255 : Y 1 = N(i-propyl) and R 2 = CD 3 , and

L A270 : Y 1 = N(i-propyl) and R 2 = CD 3 .

10. The compound of claim 1 , wherein the compound has a formula of M(L A ) n (L B ) m-n ;

wherein M is Ir or Pt; L B is a bidentate ligand; and

wherein when M is Ir, m is 3, and n is 1, 2, or 3; when M is Pt, m is 2, and n is 1, or 2.

11. The compound of claim 10 , wherein the compound has a formula of Ir(L A ) 3 ;

Ir(L A )(L B ) 2 or Ir(L A ) 2 (L B ), wherein L B is different from L A ; or

Pt(L A )(L B ) wherein L A and L B can be same or different.

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

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;

wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, R a , R b , R c , and R d are each 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; and

wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

13. The compound of claim 9 , wherein the compound is the Compound Ax having the formula Ir(L Ai ) 2 (L Cj );

wherein x=17i+j−17; i is an integer from 1 to 270, and j is an integer from 1 to 17; and

wherein L Cj has the following formula:

14. The compound of claim 9 , wherein the compound is Compound By having the formula Ir(L Ai )(L Bk ) 2 ;

wherein y=300i+k−300; i is an integer from 1 to 270, and j is an integer from 1 to 300; and

wherein L Bk has the following formula:

15. 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 comprising a first ligand L A having the Formula:

wherein rings A and B are each a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R A and R B each independently represent mono to the possible maximum number of substitution, or no substitution;

wherein Z 1 and Z 2 are each independently selected from the group consisting of carbon or nitrogen;

wherein each R A and R B 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 any adjacent substituents are optionally joined or fused into a ring;

wherein (1) at least one R A comprises an aromatic group further fused by a first group; or (2) two adjacent R A s form a first group fused to ring A;

wherein the first group is selected from the group consisting of:

wherein R is 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 the ligand L A is coordinated to a metal M;

wherein the metal M can be coordinated to other ligands; and

wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

16. The OLED of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

17. The OLED of claim 15 , wherein the organic layer further comprises a host, wherein 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 OLED of claim 15 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

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 compound comprising a first ligand L A having the Formula:

wherein rings A and B are each a 5 or 6-membered carbocyclic or heterocyclic ring;

wherein R A and R B each independently represent mono to the possible maximum number of substitution, or no substitution;

wherein Z 1 and Z 2 are each independently selected from the group consisting of carbon or nitrogen;

wherein each R A and R B 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 any adjacent substituents are optionally joined or fused into a ring;

wherein (1) at least one R A comprises an aromatic group further fused by a first group; or (2) two adjacent R A s form a first group fused to ring A;

wherein the first group is selected from the group consisting of:

wherein R is 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 the ligand L A is coordinated to a metal M;

wherein the metal M can be coordinated to other ligands; and

wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

20. The consumer product of claim 19 , wherein the consumer product is 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, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, and a sign.

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded May 5, 2017
From: BOUDREAULT, PIERRE-LUC T.; ALLEYNE, BERT; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 042257/0445 →
Continuity (3)
Provisional Application 62425170 · Nov 22, 2016
Provisional Application 62359860 · Jul 8, 2016
Related Publication 20180013077A1 · Jan 11, 2018