IP Library Granted Patent US 10,199,581
Granted Patent B2
US 10,199,581 · App. 13/932,508 · Granted Feb 5, 2019

Organic electroluminescent materials and devices

Inventors: Pierre-Luc T. Boudreault (Pennington, NJ); Alexey Dyatkin (Ambler, PA); David Zenan Li (Princeton, NJ); Scott Joseph (Ewing, NJ); Chuanjun Xia (Lawrenceville, NJ); Hitoshi Yamamoto (Pennington, NJ); Michael S. Weaver (Princeton, NJ); Bert Alleyne (Newtown, PA); James Fiordeliso (Yardley, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0085C07F15/0033C09K11/06C09K2211/1007C09K2211/1029C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 10,199,581
App. No.
13/932,508
Granted
Feb 5, 2019
Kind
B2
Abstract

A compound having an ancillary ligand L 1 having the formula: Formula I is disclosed. The ligand L 1 is coordinated to a metal M having an atomic number greater than 40, and two adjacent substituents are optionally joined to form into a ring. Such compound is suitable for use as emitters in organic light emitting devices.

Claims (2457)

1. A compound having the formula Ir(L 1 ) x (L 2 ) y (L 3 ) z :

wherein L 1 is selected from the group consisting of

wherein L 2 is a second ligand and L 3 is a third ligand and L 2 and L 3 can be the same or different;

wherein the second ligand L 2 and the third ligand L 3 are structure (a) independently selected from the group consisting of:

or structure (b) independently selected from the group consisting of

wherein x is 1 or 2;

wherein y is 1, or 2;

wherein z is 0 or 1;

wherein x+y+z is 3;

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; and

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

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

3. The compound of claim 1 , wherein L 1 is

4. The compound of claim 1 , wherein L 2 is selected from group consisting of:

5. The compound of claim 4 , wherein the compound having the formula of M(L 1 )(L 2 ) 2 is selected from the group consisting of Compounds 267-399, 533-666, 799-931, 1065-1330, and 1597-1729 defined in the table below:

Compound

number

L 1

L 2

267.

L A3

L Q1

268.

L A3

L Q2

269.

L A3

L Q3

270.

L A3

L Q4

271.

L A3

L Q5

272.

L A3

L Q6

273.

L A3

L Q7

274.

L A3

L Q8

275.

L A3

L Q9

276.

L A3

L Q10

277.

L A3

L Q11

278.

L A3

L Q12

279.

L A3

L Q13

280.

L A3

L Q14

281.

L A3

L Q15

282.

L A3

L Q16

283.

L A3

L Q17

284.

L A3

L Q18

285.

L A3

L Q19

286.

L A3

L Q20

287.

L A3

L Q21

288.

L A3

L Q22

289.

L A3

L Q23

290.

L A3

L Q24

291.

L A3

L Q25

292.

L A3

L Q26

293.

L A3

L Q27

294.

L A3

L Q28

295.

L A3

L Q29

296.

L A3

L Q30

297.

L A3

L Q31

298.

L A3

L Q32

299.

L A3

L Q33

300.

L A3

L Q34

301.

L A3

L Q35

302.

L A3

L Q36

303.

L A3

L Q37

304.

L A3

L Q38

305.

L A3

L Q39

306.

L A3

L Q40

307.

L A3

L Q41

308.

L A3

L Q42

309.

L A3

L Q43

310.

L A3

L Q44

311.

L A3

L Q45

312.

L A3

L Q46

313.

L A3

L Q47

314.

L A3

L Q48

315.

L A3

L Q49

316.

L A3

L Q50

317.

L A3

L Q51

318.

L A3

L Q52

319.

L A3

L Q53

320.

L A3

L Q54

321.

L A3

L Q55

322.

L A3

L Q56

323.

L A3

L Q57

324.

L A3

L Q58

325.

L A3

L Q59

326.

L A3

L Q60

327.

L A3

L Q61

328.

L A3

L Q62

329.

L A3

L Q63

330.

L A3

L Q64

331.

L A3

L Q65

332.

L A3

L Q66

333.

L A3

L Q67

334.

L A3

L Q68

335.

L A3

L Q69

336.

L A3

L Q70

337.

L A3

L Q71

338.

L A3

L Q72

339.

L A3

L Q73

340.

L A3

L Q74

341.

L A3

L Q75

342.

L A3

L Q76

343.

L A3

L Q77

344.

L A3

L Q78

345.

L A3

L Q79

346.

L A3

L Q80

347.

L A3

L Q81

348.

L A3

L Q82

349.

L A3

L Q83

350.

L A3

L Q84

351.

L A3

L Q85

352.

L A3

L Q86

353.

L A3

L Q87

354.

L A3

L Q88

355.

L A3

L Q89

356.

L A3

L Q90

357.

L A3

L Q91

358.

L A3

L Q92

359.

L A3

L Q93

360.

L A3

L Q94

361.

L A3

L Q95

362.

L A3

L Q96

363.

L A3

L Q97

364.

L A3

L Q98

365.

L A3

L Q99

366.

L A3

L Q100

367.

L A3

L Q101

368.

L A3

L Q102

369.

L A3

L Q103

370.

L A3

L Q104

371.

L A3

L Q105

372.

L A3

L Q106

373.

L A3

L Q107

374.

L A3

L Q108

375.

L A3

L Q109

376.

L A3

L Q110

377.

L A3

L Q111

378.

L A3

L Q112

379.

L A3

L Q113

380.

L A3

L Q114

381.

L A3

L Q115

382.

L A3

L Q116

383.

L A3

L Q117

384.

L A3

L Q118

385.

L A3

L Q119

386.

L A3

L Q120

387.

L A3

L Q121

388.

L A3

L Q122

389.

L A3

L Q123

390.

L A3

L Q124

391.

L A3

L Q125

392.

L A3

L Q126

393.

L A3

L Q127

394.

L A3

L Q128

395.

L A3

L Q129

396.

L A3

L Q130

397.

L A3

L Q131

398.

L A3

L Q132

399.

L A3

L Q133

533.

L A5

L Q1

534.

L A5

L Q2

535.

L A5

L Q3

536.

L A5

L Q4

537.

L A5

L Q5

538.

L A5

L Q6

539.

L A5

L Q7

540.

L A5

L Q8

541.

L A5

L Q9

542.

L A5

L Q10

543.

L A5

L Q11

544.

L A5

L Q12

545.

L A5

L Q13

546.

L A5

L Q14

547.

L A5

L Q15

548.

L A5

L Q16

549.

L A5

L Q17

550.

L A5

L Q18

551.

L A5

L Q19

552.

L A5

L Q20

553.

L A5

L Q21

554.

L A5

L Q22

555.

L A5

L Q23

556.

L A5

L Q24

557.

L A5

L Q25

558.

L A5

L Q26

559.

L A5

L Q27

560.

L A5

L Q28

561.

L A5

L Q29

562.

L A5

L Q30

563.

L A5

L Q31

564.

L A5

L Q32

565.

L A5

L Q33

566.

L A5

L Q34

567.

L A5

L Q35

568.

L A5

L Q36

569.

L A5

L Q37

570.

L A5

L Q38

571.

L A5

L Q39

572.

L A5

L Q40

573.

L A5

L Q41

574.

L A5

L Q42

575.

L A5

L Q43

576.

L A5

L Q44

577.

L A5

L Q45

578.

L A5

L Q46

579.

L A5

L Q47

580.

L A5

L Q48

581.

L A5

L Q49

582.

L A5

L Q50

583.

L A5

L Q51

584.

L A5

L Q52

585.

L A5

L Q53

586.

L A5

L Q54

587.

L A5

L Q55

588.

L A5

L Q56

589.

L A5

L Q57

590.

L A5

L Q58

591.

L A5

L Q59

592.

L A5

L Q60

593.

L A5

L Q61

594.

L A5

L Q62

595.

L A5

L Q63

596.

L A5

L Q64

597.

L A5

L Q65

598.

L A5

L Q66

599.

L A5

L Q67

600.

L A5

L Q68

601.

L A5

L Q69

602.

L A5

L Q70

603.

L A5

L Q71

604.

L A5

L Q72

605.

L A5

L Q73

606.

L A5

L Q74

607.

L A5

L Q75

608.

L A5

L Q76

609.

L A5

L Q77

610.

L A5

L Q78

611.

L A5

L Q79

612.

L A5

L Q80

613.

L A5

L Q81

614.

L A5

L Q82

615.

L A5

L Q83

616.

L A5

L Q84

617.

L A5

L Q85

618.

L A5

L Q86

619.

L A5

L Q87

620.

L A5

L Q88

621.

L A5

L Q89

622.

L A5

L Q90

623.

L A5

L Q91

624.

L A5

L Q92

625.

L A5

L Q93

626.

L A5

L Q94

627.

L A5

L Q95

628.

L A5

L Q96

629.

L A5

L Q97

630.

L A5

L Q98

631.

L A5

L Q99

632.

L A5

L Q100

633.

L A5

L Q101

634.

L A5

L Q102

635.

L A5

L Q103

636.

L A5

L Q104

637.

L A5

L Q105

638.

L A5

L Q106

639.

L A5

L Q107

640.

L A5

L Q108

641.

L A5

L Q109

642.

L A5

L Q110

643.

L A5

L Q111

644.

L A5

L Q112

645.

L A5

L Q113

646.

L A5

L Q114

647.

L A5

L Q115

648.

L A5

L Q116

649.

L A5

L Q117

650.

L A5

L Q118

651.

L A5

L Q119

652.

L A5

L Q120

653.

L A5

L Q121

654.

L A5

L Q122

655.

L A5

L Q123

656.

L A5

L Q124

657.

L A5

L Q125

658.

L A5

L Q126

659.

L A5

L Q127

660.

L A5

L Q128

661.

L A5

L Q129

662.

L A5

L Q130

663.

L A5

L Q131

664.

L A5

L Q132

665.

L A5

L Q133

799.

L A7

L Q1

800.

L A7

L Q2

801.

L A7

L Q3

802.

L A7

L Q4

803.

L A7

L Q5

804.

L A7

L Q6

805.

L A7

L Q7

806.

L A7

L Q8

807.

L A7

L Q9

808.

L A7

L Q10

809.

L A7

L Q11

810.

L A7

L Q12

811.

L A7

L Q13

812.

L A7

L Q14

813.

L A7

L Q15

814.

L A7

L Q16

815.

L A7

L Q17

816.

L A7

L Q18

817.

L A7

L Q19

818.

L A7

L Q20

819.

L A7

L Q21

820.

L A7

L Q22

821.

L A7

L Q23

822.

L A7

L Q24

823.

L A7

L Q25

824.

L A7

L Q26

825.

L A7

L Q27

826.

L A7

L Q28

827.

L A7

L Q29

828.

L A7

L Q30

829.

L A7

L Q31

830.

L A7

L Q32

831.

L A7

L Q33

832.

L A7

L Q34

833.

L A7

L Q35

834.

L A7

L Q36

835.

L A7

L Q37

836.

L A7

L Q38

837.

L A7

L Q39

838.

L A7

L Q40

839.

L A7

L Q41

840.

L A7

L Q42

841.

L A7

L Q43

842.

L A7

L Q44

843.

L A7

L Q45

844.

L A7

L Q46

845.

L A7

L Q47

846.

L A7

L Q48

847.

L A7

L Q49

848.

L A7

L Q50

849.

L A7

L Q51

850.

L A7

L Q52

851.

L A7

L Q53

852.

L A7

L Q54

853.

L A7

L Q55

854.

L A7

L Q56

855.

L A7

L Q57

856.

L A7

L Q58

857.

L A7

L Q59

858.

L A7

L Q60

859.

L A7

L Q61

860.

L A7

L Q62

861.

L A7

L Q63

862.

L A7

L Q64

863.

L A7

L Q65

864.

L A7

L Q66

865.

L A7

L Q67

866.

L A7

L Q68

867.

L A7

L Q69

868.

L A7

L Q70

869.

L A7

L Q71

870.

L A7

L Q72

871.

L A7

L Q73

872.

L A7

L Q74

873.

L A7

L Q75

874.

L A7

L Q76

875.

L A7

L Q77

876.

L A7

L Q78

877.

L A7

L Q79

878.

L A7

L Q80

879.

L A7

L Q81

880.

L A7

L Q82

881.

L A7

L Q83

882.

L A7

L Q84

883.

L A7

L Q85

884.

L A7

L Q86

885.

L A7

L Q87

886.

L A7

L Q88

887.

L A7

L Q89

888.

L A7

L Q90

889.

L A7

L Q91

890.

L A7

L Q92

891.

L A7

L Q93

892.

L A7

L Q94

893.

L A7

L Q95

894.

L A7

L Q96

895.

L A7

L Q97

896.

L A7

L Q98

897.

L A7

L Q99

898.

L A7

L Q100

899.

L A7

L Q101

900.

L A7

L Q102

901.

L A7

L Q103

902.

L A7

L Q104

903.

L A7

L Q105

904.

L A7

L Q106

905.

L A7

L Q107

906.

L A7

L Q108

907.

L A7

L Q109

908.

L A7

L Q110

909.

L A7

L Q111

910.

L A7

L Q112

911.

L A7

L Q113

912.

L A7

L Q114

913.

L A7

L Q115

914.

L A7

L Q116

915.

L A7

L Q117

916.

L A7

L Q118

917.

L A7

L Q119

918.

L A7

L Q120

919.

L A7

L Q121

920.

L A7

L Q122

921.

L A7

L Q123

922.

L A7

L Q124

923.

L A7

L Q125

924.

L A7

L Q126

925.

L A7

L Q127

926.

L A7

L Q128

927.

L A7

L Q129

928.

L A7

L Q130

929.

L A7

L Q131

930.

L A7

L Q132

931.

L A7

L Q133

1065.

L A9

L Q1

1066.

L A9

L Q2

1067.

L A9

L Q3

1068.

L A9

L Q4

1069.

L A9

L Q5

1070.

L A9

L Q6

1071.

L A9

L Q7

1072.

L A9

L Q8

1073.

L A9

L Q9

1074.

L A9

L Q10

1075.

L A9

L Q11

1076.

L A9

L Q12

1077.

L A9

L Q13

1078.

L A9

L Q14

1079.

L A9

L Q15

1080.

L A9

L Q16

1081.

L A9

L Q17

1082.

L A9

L Q18

1083.

L A9

L Q19

1084.

L A9

L Q20

1085.

L A9

L Q21

1086.

L A9

L Q22

1087.

L A9

L Q23

1088.

L A9

L Q24

1089.

L A9

L Q25

1090.

L A9

L Q26

1091.

L A9

L Q27

1092.

L A9

L Q28

1093.

L A9

L Q29

1094.

L A9

L Q30

1095.

L A9

L Q31

1096.

L A9

L Q32

1097.

L A9

L Q33

1098.

L A9

L Q34

1099.

L A9

L Q35

1100.

L A9

L Q36

1101.

L A9

L Q37

1102.

L A9

L Q38

1103.

L A9

L Q39

1104.

L A9

L Q40

1105.

L A9

L Q41

1106.

L A9

L Q42

1107.

L A9

L Q43

1108.

L A9

L Q44

1109.

L A9

L Q45

1110.

L A9

L Q46

1111.

L A9

L Q47

1112.

L A9

L Q48

1113.

L A9

L Q49

1114.

L A9

L Q50

1115.

L A9

L Q51

1116.

L A9

L Q52

1117.

L A9

L Q53

1118.

L A9

L Q54

1119.

L A9

L Q55

1120.

L A9

L Q56

1121.

L A9

L Q57

1122.

L A9

L Q58

1123.

L A9

L Q59

1124.

L A9

L Q60

1125.

L A9

L Q61

1126.

L A9

L Q62

1127.

L A9

L Q63

1128.

L A9

L Q64

1129.

L A9

L Q65

1130.

L A9

L Q66

1131.

L A9

L Q67

1132.

L A9

L Q68

1133.

L A9

L Q69

1134.

L A9

L Q70

1135.

L A9

L Q71

1136.

L A9

L Q72

1137.

L A9

L Q73

1138.

L A9

L Q74

1139.

L A9

L Q75

1140.

L A9

L Q76

1141.

L A9

L Q77

1142.

L A9

L Q78

1143.

L A9

L Q79

1144.

L A9

L Q80

1145.

L A9

L Q81

1146.

L A9

L Q82

1147.

L A9

L Q83

1148.

L A9

L Q84

1149.

L A9

L Q85

1150.

L A9

L Q86

1151.

L A9

L Q87

1152.

L A9

L Q88

1153.

L A9

L Q89

1154.

L A9

L Q90

1155.

L A9

L Q91

1156.

L A9

L Q92

1157.

L A9

L Q93

1158.

L A9

L Q94

1159.

L A9

L Q95

1160.

L A9

L Q96

1161.

L A9

L Q97

1162.

L A9

L Q98

1163.

L A9

L Q99

1164.

L A9

L Q100

1165.

L A9

L Q101

1166.

L A9

L Q102

1167.

L A9

L Q103

1168.

L A9

L Q104

1169.

L A9

L Q105

1170.

L A9

L Q106

1171.

L A9

L Q107

1172.

L A9

L Q108

1173.

L A9

L Q109

1174.

L A9

L Q110

1175.

L A9

L Q111

1176.

L A9

L Q112

1177.

L A9

L Q113

1178.

L A9

L Q114

1179.

L A9

L Q115

1180.

L A9

L Q116

1181.

L A9

L Q117

1182.

L A9

L Q118

1183.

L A9

L Q119

1184.

L A9

L Q120

1185.

L A9

L Q121

1186.

L A9

L Q122

1187.

L A9

L Q123

1188.

L A9

L Q124

1189.

L A9

L Q125

1190.

L A9

L Q126

1191.

L A9

L Q127

1192.

L A9

L Q128

1193.

L A9

L Q129

1194.

L A9

L Q130

1195.

L A9

L Q131

1196.

L A9

L Q132

1197.

L A9

L Q133

1198.

L A10

L Q1

1199.

L A10

L Q2

1200.

L A10

L Q3

1201.

L A10

L Q4

1202.

L A10

L Q5

1203.

L A10

L Q6

1204.

L A10

L Q7

1205.

L A10

L Q8

1206.

L A10

L Q9

1207.

L A10

L Q10

1208.

L A10

L Q11

1209.

L A10

L Q12

1210.

L A10

L Q13

1211.

L A10

L Q14

1212.

L A10

L Q15

1213.

L A10

L Q16

1214.

L A10

L Q17

1215.

L A10

L Q18

1216.

L A10

L Q19

1217.

L A10

L Q20

1218.

L A10

L Q21

1219.

L A10

L Q22

1220.

L A10

L Q23

1221.

L A10

L Q24

1222.

L A10

L Q25

1223.

L A10

L Q26

1224.

L A10

L Q27

1225.

L A10

L Q28

1226.

L A10

L Q29

1227.

L A10

L Q30

1228.

L A10

L Q31

1229.

L A10

L Q32

1230.

L A10

L Q33

1231.

L A10

L Q34

1232.

L A10

L Q35

1233.

L A10

L Q36

1234.

L A10

L Q37

1235.

L A10

L Q38

1236.

L A10

L Q39

1237.

L A10

L Q40

1238.

L A10

L Q41

1239.

L A10

L Q42

1240.

L A10

L Q43

1241.

L A10

L Q44

1242.

L A10

L Q45

1243.

L A10

L Q46

1244.

L A10

L Q47

1245.

L A10

L Q48

1246.

L A10

L Q49

1247.

L A10

L Q50

1248.

L A10

L Q51

1249.

L A10

L Q52

1250.

L A10

L Q53

1251.

L A10

L Q54

1252.

L A10

L Q55

1253.

L A10

L Q56

1254.

L A10

L Q57

1255.

L A10

L Q58

1256.

L A10

L Q59

1257.

L A10

L Q60

1258.

L A10

L Q61

1259.

L A10

L Q62

1260.

L A10

L Q63

1261.

L A10

L Q64

1262.

L A10

L Q65

1263.

L A10

L Q66

1264.

L A10

L Q67

1265.

L A10

L Q68

1266.

L A10

L Q69

1267.

L A10

L Q70

1268.

L A10

L Q71

1269.

L A10

L Q72

1270.

L A10

L Q73

1271.

L A10

L Q74

1272.

L A10

L Q75

1273.

L A10

L Q76

1274.

L A10

L Q77

1275.

L A10

L Q78

1276.

L A10

L Q79

1277.

L A10

L Q80

1278.

L A10

L Q81

1279.

L A10

L Q82

1280.

L A10

L Q83

1281.

L A10

L Q84

1282.

L A10

L Q85

1283.

L A10

L Q86

1284.

L A10

L Q87

1285.

L A10

L Q88

1286.

L A10

L Q89

1287.

L A10

L Q90

1288.

L A10

L Q91

1289.

L A10

L Q92

1290.

L A10

L Q93

1291.

L A10

L Q94

1292.

L A10

L Q95

1293.

L A10

L Q96

1294.

L A10

L Q97

1295.

L A10

L Q98

1296.

L A10

L Q99

1297.

L A10

L Q100

1298.

L A10

L Q101

1299.

L A10

L Q102

1300.

L A10

L Q103

1301.

L A10

L Q104

1302.

L A10

L Q105

1303.

L A10

L Q106

1304.

L A10

L Q107

1305.

L A10

L Q108

1306.

L A10

L Q109

1307.

L A10

L Q110

1308.

L A10

L Q111

1309.

L A10

L Q112

1310.

L A10

L Q113

1311.

L A10

L Q114

1312.

L A10

L Q115

1313.

L A10

L Q116

1314.

L A10

L Q117

1315.

L A10

L Q118

1316.

L A10

L Q119

1317.

L A10

L Q120

1318.

L A10

L Q121

1319.

L A10

L Q122

1320.

L A10

L Q123

1321.

L A10

L Q124

1322.

L A10

L Q125

1323.

L A10

L Q126

1324.

L A10

L Q127

1325.

L A10

L Q128

1326.

L A10

L Q129

1327.

L A10

L Q130

1328.

L A10

L Q131

1329.

L A10

L Q132

1330.

L A10

L Q133

1597.

L A13

L Q1

1598.

L A13

L Q2

1599.

L A13

L Q3

1600.

L A13

L Q4

1601.

L A13

L Q5

1602.

L A13

L Q6

1603.

L A13

L Q7

1604.

L A13

L Q8

1605.

L A13

L Q9

1606.

L A13

L Q10

1607.

L A13

L Q11

1608.

L A13

L Q12

1609.

L A13

L Q13

1610.

L A13

L Q14

1611.

L A13

L Q15

1612.

L A13

L Q16

1613.

L A13

L Q17

1614.

L A13

L Q18

1615.

L A13

L Q19

1616.

L A13

L Q20

1617.

L A13

L Q21

1618.

L A13

L Q22

1619.

L A13

L Q23

1620.

L A13

L Q24

1621.

L A13

L Q25

1622.

L A13

L Q26

1623.

L A13

L Q27

1624.

L A13

L Q28

1625.

L A13

L Q29

1626.

L A13

L Q30

1627.

L A13

L Q31

1628.

L A13

L Q32

1629.

L A13

L Q33

1630.

L A13

L Q34

1631.

L A13

L Q35

1632.

L A13

L Q36

1633.

L A13

L Q37

1634.

L A13

L Q38

1635.

L A13

L Q39

1636.

L A13

L Q40

1637.

L A13

L Q41

1638.

L A13

L Q42

1639.

L A13

L Q43

1640.

L A13

L Q44

1641.

L A13

L Q45

1642.

L A13

L Q46

1643.

L A13

L Q47

1644.

L A13

L Q48

1645.

L A13

L Q49

1646.

L A13

L Q50

1647.

L A13

L Q51

1648.

L A13

L Q52

1649.

L A13

L Q53

1650.

L A13

L Q54

1651.

L A13

L Q55

1652.

L A13

L Q56

1653.

L A13

L Q57

1654.

L A13

L Q58

1655.

L A13

L Q59

1656.

L A13

L Q60

1657.

L A13

L Q61

1658.

L A13

L Q62

1659.

L A13

L Q63

1660.

L A13

L Q64

1661.

L A13

L Q65

1662.

L A13

L Q66

1663.

L A13

L Q67

1664.

L A13

L Q68

1665.

L A13

L Q69

1666.

L A13

L Q70

1667.

L A13

L Q71

1668.

L A13

L Q72

1669.

L A13

L Q73

1670.

L A13

L Q74

1671.

L A13

L Q75

1672.

L A13

L Q76

1673.

L A13

L Q77

1674.

L A13

L Q78

1675.

L A13

L Q79

1676.

L A13

L Q80

1677.

L A13

L Q81

1678.

L A13

L Q82

1679.

L A13

L Q83

1680.

L A13

L Q84

1681.

L A13

L Q85

1682.

L A13

L Q86

1683.

L A13

L Q87

1684.

L A13

L Q88

1685.

L A13

L Q89

1686.

L A13

L Q90

1687.

L A13

L Q91

1688.

L A13

L Q92

1689.

L A13

L Q93

1690.

L A13

L Q94

1691.

L A13

L Q95

1692.

L A13

L Q96

1693.

L A13

L Q97

1694.

L A13

L Q98

1695.

L A13

L Q99

1696.

L A13

L Q100

1697.

L A13

L Q101

1698.

L A13

L Q102

1699.

L A13

L Q103

1700.

L A13

L Q104

1701.

L A13

L Q105

1702.

L A13

L Q106

1703.

L A13

L Q107

1704.

L A13

L Q108

1705.

L A13

L Q109

1706.

L A13

L Q110

1707.

L A13

L Q111

1708.

L A13

L Q112

1709.

L A13

L Q113

1710.

L A13

L Q114

1711.

L A13

L Q115

1712.

L A13

L Q116

1713.

L A13

L Q117

1714.

L A13

L Q118

1715.

L A13

L Q119

1716.

L A13

L Q120

1717.

L A13

L Q121

1718.

L A13

L Q122

1719.

L A13

L Q123

1720.

L A13

L Q124

1721.

L A13

L Q125

1722.

L A13

L Q126

1723.

L A13

L Q127

1724.

L A13

L Q128

1725.

L A13

L Q129

1726.

L A13

L Q130

1727.

L A13

L Q131

1728.

L A13

L Q132

1729.

L A13

L Q133 .

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

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

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

9. The compound of claim 1 , wherein L 1 is,

10. The compound of claim 1 , wherein L 1 is

11. The compound of claim 1 , wherein L 1 is

12. 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 compound-having the formula Ir(L 1 ) x (L 2 ) y (L 3 ) z :

wherein L 1 is selected from the group consisting of

wherein L 2 is a second ligand and L 3 is a third ligand and L 2 and L 3 can be the same or different;

wherein the second ligand L 2 and the third ligand L 3 are structure (a) independently selected from the group consisting of:

or structure (b) independently selected from the group consisting of

wherein x is 1 or 2;

wherein y is 1, or 2;

wherein z is 0 or 1;

wherein x+y+z is 3;

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; and

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

13. The first device of claim 12 , wherein the compound is selected from the group consisting of

14. The first device of claim 12 , wherein the first device is a consumer product selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, lights for interior or exterior illumination and/or signaling, a heads up display, a fully transparent display, a flexible display, a laser printer, a telephone, a cell phone, 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 wall, theater or stadium screen, and a sign.

15. The first device of claim 12 , wherein the organic layer is an emissive layer and the compound is an emissive dopant, or the organic layer is an emissive layer and the compound is a non-emissive dopant.

16. The first device of claim 12 , wherein the organic layer further comprises a host material.

17. The first device of claim 16 , wherein the host material comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host material is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡C—C n H 2n+1 , Ar 1 , Ar 1 -Ar 2 , and C n H 2n —Ar 1 ;

wherein n is from 1 to 10; and

wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

18. The first device of claim 16 , wherein the host material comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

19. The first device of claim 16 , wherein the host material is selected from the group consisting of:

and combinations thereof.

20. The first device of claim 16 , wherein the host material comprises a metal complex.

21. The first device of claim 20 , wherein the host material is a metal 8-hydroxyquinolate.

22. A formulation comprising a compound having the formula Ir(L 1 ) x (L 2 ) y (L 3 ) z :

wherein L 1 is selected from the group consisting of

wherein L 2 is a second ligand and L 3 is a third ligand and L 2 and L 3 can be the same or different;

wherein the second ligand L 2 and the third ligand L 3 are structure (a) independently selected from the group consisting of:

or structure (b) independently selected from the group consisting of

wherein x is 1 or 2;

wherein y is 1, or 2;

wherein z is 0 or 1;

wherein x+y+z is 3;

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; and

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 8, 2013
From: BOUDREAULT, PIERRE-LUC; DYATKIN, ALEXEY; LI, DAVID ZENAN; JOSEPH, SCOTT; XIA, CHUANJUN; YAMAMOTO, HITOSHI; WEAVER, MICHAEL S.; ALLEYNE, BERT; FIORDELISO, JAMES
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 030748/0702 →
Continuity (1)
Related Publication 20150001472A1 · Jan 1, 2015
Cited By (3)
US 12,262,630 US 12,325,716 US 12,615,957