Organic electroluminescent materials and devices
Provided are compounds including a ligand L A of the following Formula I: that contain heavy elements like Sb, Bi, or Te. Also provided are formulations including such compounds. Further provided are OLEDs and related consumer products that utilize such compounds.
1 . A compound comprising a ligand L A of the following Formula I:
wherein:
rings A and B are each independently a monocyclic or fused multicyclic ring system consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic ring;
X 1 -X 4 are each independently C or N with the proviso that at least two of X 1 -X 4 are C, and the rest of X 1 -X 4 are N;
each R A and R B independently represents mono to the maximum allowable substitution, or no substitution;
K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, and S;
when K 1 is O or S, X 1 is C; when K 2 is O or S, X 3 is C;
L is selected from the group consisting of a direct bond, ER n , O, S, CR′R″, SiR′R″, BR′, and NR′;
each R A , R B , R′, and R″ is independently a hydrogen or a substituent selected from the group consisting of ER n , deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
at least one of R A , R B , R′, or R″ comprising a substituent E;
E is selected from the group consisting of Sb, Bi, and Te;
n is an integer from 1 to 5;
each R can be the same or different;
R can be fused to ring A or ring B to form a five or six-membered ring;
each R is a hydrogen or a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, oxo, and combinations thereof;
if E is a ring atom, then E is a ring atom in a metal chelate with the metal M or E is a ring atom in a 5-membered ring;
L A is coordinated to a metal M through the dashed lines;
M is selected from the group consisting of Os, Ir, Rh, Re, Ru, Pd, Pt, Cu, Ag, and Au;
M can be coordinated to other ligands;
when M is Pt, L A is joined with at least one of the other ligands to comprise a tridentate or tetradentate ligand;
L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two of R A , R B , R, R′, and R″ can be joined or fused to form a ring; and
the compound is a neutral compound.
2 . The compound of claim 1 , wherein at least one of R A or R B comprises ER n .
3 . The compound of claim 1 , wherein one of the following is true:
X 1 -X 4 are all C;
only one of X 1 -X 4 is N, and the rest of X 1 -X 4 are C; or
only two of X 1 -X 4 are C, and the rest of X 1 -X 4 are N.
4 . The compound of claim 1 , wherein each R A and R B is independently a hydrogen or a substituent selected from the group consisting of ER n deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, boryl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and
each R is independently a hydrogen or a substituent selected from the group consisting of halogen, aryl, alkyl, heteroalkyl and combinations thereof.
5 . The compound of claim 1 , wherein one of K 1 and K 2 is a direct bond and the other one is O or S.
6 . The compound of claim 1 , wherein ring A or ring B is selected from the group consisting of:
wherein,
K represents K 1 or K 2 , which are independently selected from the group consisting of a direct bond, O, and S;
X is C or N, wherein when K is O or S, X is C;
X 5 -X 12 are each independently C or N;
R C represents mono to the maximum allowable substitution, or no substitution;
each R C can be a hydrogen or a substituent selected from the group consisting of ER n , deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
at least one of R C comprising a substituent E&, wherein the index n is an integer from 1 to 5;
E is selected from the group consisting of Sb, Bi, and Te;
each R can be same or different;
R can be fused to ring A or ring B to form a five or six-membered ring;
each R is a hydrogen or a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, oxo, and combinations thereof; and
Y A is selected from the group consisting of O, S, CR′R″, SiR′R″, BR′, NR′, and ER n-1 .
7 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
wherein
Y B is selected from the group consisting of O and S.
8 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of L Ai-m wherein i=1 to 800, m=1 to 42, and based on formula L Ai-1 to L A1-42 ; L Ai-m′ wherein i=801 to 1500, m′=43 to 60, and based on formula L Ai-43 to L Ai-60 ; and L Ai-m″ wherein i=1501 to 3000, m″=61 to 107, and based on formula L Ai-61 to L A1-107 , wherein the structures of L Ai-1 through L Ai-107 are shown in the following table:
L Ai-1 is based on formula 1
L Ai-2 is based on formula 2
L Ai-3 is based on formula 3
L Ai-4 is based on formula 4
L Ai-5 is based on formula 5
L Ai-6 is based on formula 6
L Ai-7 is based on formula 7
L Ai-8 is based on formula 8
L Ai-9 is based on formula 9
L Ai-10 is based on formula 10
L Ai-11 is based on formula 11
L Ai-12 is based on formula 12
L Ai-13 is based on formula 13
L Ai-14 is based on formula 14
L Ai-15 is based on formula 15
L Ai-16 is based on formula 16
L Ai-17 is based on formula 17
L Ai-18 is based on formula 18
L Ai-19 is based on formula 19
L Ai-20 is based on formula 20
L Ai-21 is based on formula 21
L Ai-22 is based on formula 22
L Ai-23 is based on formula 23
L Ai-24 is based on formula 24
L Ai-25 is based on formula 25
L Ai-26 is based on formula 26
L Ai-27 is based on formula 27
L Ai-28 is based on formula 28
L Ai-29 is based on formula 29
L Ai-30 is based on formula 30
L Ai-31 is based on formula 31
L Ai-32 is based on formula 32
L Ai-33 is based on formula 33
L Ai-34 is based on formula 34
L Ai-35 is based on formula 35
L Ai-36 is based on formula 36
L Ai-37 is based on formula 37
L Ai-38 is based on formula 38
L Ai-39 is based on formula 39
L Ai-40 is based on formula 40
L Ai-41 is based on formula 41
L Ai-42 is based on formula 42
L Ai-43 is based on formula 43
L Ai-44 is based on formula 44
L Ai-45 is based on formula 45
L Ai-46 is based on formula 46
L Ai-47 is based on formula 47
L Ai-48 is based on formula 48
L Ai-49 is based on formula 49
L Ai-50 is based on formula 50
L Ai-51 is based on formula 51
L Ai-52 is based on formula 52
L Ai-53 is based on formula 53
L Ai-54 is based on formula 54
L Ai-55 is based on formula 55
L Ai-56 is based on formula 56
L Ai-57 is based on formula 57
L Ai-58 is based on formula 58
L Ai-59 is based on formula 59
L Ai-60 is based on formula 60
L Ai-61 is based on formula 61
L Ai-62 is based on formula 62
L Ai-63 is based on formula 63
L Ai-64 is based on formula 64
L Ai-65 is based on formula 65
L Ai-66 is based on formula 66
L Ai-67 is based on formula 67
L Ai-68 is based on formula 68
L Ai-69 is based on formula 69
L Ai-70 is based on formula 70
L Ai-71 is based on formula 71
L Ai-72 is based on formula 72
L Ai-73 is based on formula 73
L Ai-74 is based on formula 74
L Ai-75 is based on formula 75
L Ai-76 is based on formula 76
L Ai-77 is based on formula 77
L Ai-78 is based on formula 78
L Ai-79 is based on formula 79
L Ai-80 is based on formula 80
L Ai-81 is based on formula 81
L Ai-82 is based on formula 82
L Ai-83 is based on formula 83
L Ai-84 is based on formula 84
L Ai-85 is based on formula 85
L Ai-86 is based on formula 86
L Ai-87 is based on formula 87
L Ai-88 is based on formula 88
L Ai-89 is based on formula 89
L Ai-90 is based on formula 90
L Ai-91 is based on formula 91
L Ai-92 is based on formula 92
L Ai-93 is based on formula 93
L Ai-94 is based on formula 94
L Ai-95 is based on formula 95
L Ai-96 is based on formula 96
L Ai-97 is based on formula 97
L Ai-98 is based on formula 98
L Ai-99 is based on formula 99
L Ai-100 is based on formula 100
L Ai-101 is based on formula 101
L Ai-102 is based on formula 102
L Ai-103 is based on formula 103
L Ai-104 is based on formula 104
L Ai-105 is based on formula 105
L Ai-106 is based on formula 106
L Ai-107 is based on formula 107
wherein for each L Ai , where i=1 to 3000, ER n/n-1 , R E , and G have the structures defined in the following Table 2, where index n is an integer from 1 to 5:
L Ai
ER n/n−1
G
L Ai
ER n/n−1
G
L Ai
R E
G
L Ai
R E
G
L A1
R 1
G 1
L A751
R 31
G 10
L A1501
R E1
G 11
L A2251
R E1
G 26
L A2
R 2
G 1
L A752
R 32
G 10
L A1502
R E2
G 11
L A2252
R E2
G 26
L A3
R 3
G 1
L A753
R 33
G 10
L A1503
R E3
G 11
L A2253
R E3
G 26
L A4
R 4
G 1
L A754
R 34
G 10
L A1504
R E4
G 11
L A2254
R E4
G 26
L A5
R 5
G 1
L A755
R 35
G 10
L A1505
R E5
G 11
L A2255
R E5
G 26
L A6
R 6
G 1
L A756
R 36
G 10
L A1506
R E6
G 11
L A2256
R E6
G 26
L A7
R 7
G 1
L A757
R 37
G 10
L A1507
R E7
G 11
L A2257
R E7
G 26
L A8
R 8
G 1
L A758
R 38
G 10
L A1508
R E8
G 11
L A2258
R E8
G 26
L A9
R 9
G 1
L A759
R 39
G 10
L A1509
R E9
G 11
L A2259
R E9
G 26
L A10
R 10
G 1
L A760
R 40
G 10
L A1510
R E10
G 11
L A2260
R E10
G 26
L A11
R 11
G 1
L A761
R 41
G 10
L A1511
R E11
G 11
L A2261
R E11
G 26
L A12
R 12
G 1
L A762
R 42
G 10
L A1512
R E12
G 11
L A2262
R E12
G 26
L A13
R 13
G 1
L A763
R 43
G 10
L A1513
R E13
G 11
L A2263
R E13
G 26
L A14
R 14
G 1
L A764
R 44
G 10
L A1514
R E14
G 11
L A2264
R E14
G 26
L A15
R 15
G 1
L A765
R 45
G 10
L A1515
R E15
G 11
L A2265
R E15
G 26
L A16
R 16
G 1
L A766
R 46
G 10
L A1516
R E16
G 11
L A2266
R E16
G 26
L A17
R 17
G 1
L A767
R 47
G 10
L A1517
R E17
G 11
L A2267
R E17
G 26
L A18
R 18
G 1
L A768
R 48
G 10
L A1518
R E18
G 11
L A2268
R E18
G 26
L A19
R 19
G 1
L A769
R 49
G 10
L A1519
R E19
G 11
L A2269
R E19
G 26
L A20
R 20
G 1
L A770
R 50
G 10
L A1520
R E20
G 11
L A2270
R E20
G 26
L A21
R 21
G 1
L A771
R 51
G 10
L A1521
R E21
G 11
L A2271
R E21
G 26
L A22
R 22
G 1
L A772
R 52
G 10
L A1522
R E22
G 11
L A2272
R E22
G 26
L A23
R 23
G 1
L A773
R 53
G 10
L A1523
R E23
G 11
L A2273
R E23
G 26
L A24
R 24
G 1
L A774
R 54
G 10
L A1524
R E24
G 11
L A2274
R E24
G 26
L A25
R 25
G 1
L A775
R 55
G 10
L A1525
R E25
G 11
L A2275
R E25
G 26
L A26
R 26
G 1
L A776
R 56
G 10
L A1526
R E26
G 11
L A2276
R E26
G 26
L A27
R 27
G 1
L A777
R 57
G 10
L A1527
R E27
G 11
L A2277
R E27
G 26
L A28
R 28
G 1
L A778
R 58
G 10
L A1528
R E28
G 11
L A2278
R E28
G 26
L A29
R 29
G 1
L A779
R 59
G 10
L A1529
R E29
G 11
L A2279
R E29
G 26
L A30
R 30
G 1
L A780
R 60
G 10
L A1530
R E30
G 11
L A2280
R E30
G 26
L A31
R 31
G 1
L A781
R 61
G 10
L A1531
R E31
G 11
L A2281
R E31
G 26
L A32
R 32
G 1
L A782
R 62
G 10
L A1532
R E32
G 11
L A2282
R E32
G 26
L A33
R 33
G 1
L A783
R 63
G 10
L A1533
R E33
G 11
L A2283
R E33
G 26
L A34
R 34
G 1
L A784
R 64
G 10
L A1534
R E34
G 11
L A2284
R E34
G 26
L A35
R 35
G 1
L A785
R 65
G 10
L A1535
R E35
G 11
L A2285
R E35
G 26
L A36
R 36
G 1
L A786
R 66
G 10
L A1536
R E36
G 11
L A2286
R E36
G 26
L A37
R 37
G 1
L A787
R 67
G 10
L A1537
R E37
G 11
L A2287
R E37
G 26
L A38
R 38
G 1
L A788
R 68
G 10
L A1538
R E38
G 11
L A2288
R E38
G 26
L A39
R 39
G 1
L A789
R 69
G 10
L A1539
R E39
G 11
L A2289
R E39
G 26
L A40
R 40
G 1
L A790
R 70
G 10
L A1540
R E40
G 11
L A2290
R E40
G 26
L A41
R 41
G 1
L A791
R 71
G 10
L A1541
R E41
G 11
L A2291
R E41
G 26
L A42
R 42
G 1
L A792
R 72
G 10
L A1542
R E42
G 11
L A2292
R E42
G 26
L A43
R 43
G 1
L A793
R 73
G 10
L A1543
R E43
G 11
L A2293
R E43
G 26
L A44
R 44
G 1
L A794
R 74
G 10
L A1544
R E44
G 11
L A2294
R E44
G 26
L A45
R 45
G 1
L A795
R 75
G 10
L A1545
R E45
G 11
L A2295
R E45
G 26
L A46
R 46
G 1
L A796
R 76
G 10
L A1546
R E46
G 11
L A2296
R E46
G 26
L A47
R 47
G 1
L A797
R 77
G 10
L A1547
R E47
G 11
L A2297
R E47
G 26
L A48
R 48
G 1
L A798
R 78
G 10
L A1548
R E48
G 11
L A2298
R E48
G 26
L A49
R 49
G 1
L A799
R 79
G 10
L A1549
R E49
G 11
L A2299
R E49
G 26
L A50
R 50
G 1
L A800
R 80
G 10
L A1550
R E50
G 11
L A2300
R E50
G 26
L A51
R 51
G 1
L A801
R 81
G 1
L A1551
R E1
G 12
L A2301
R E1
G 27
L A52
R 52
G 1
L A802
R 82
G 1
L A1552
R E2
G 12
L A2302
R E2
G 27
L A53
R 53
G 1
L A803
R 83
G 1
L A1553
R E3
G 12
L A2303
R E3
G 27
L A54
R 54
G 1
L A804
R 84
G 1
L A1554
R E4
G 12
L A2304
R E4
G 27
L A55
R 55
G 1
L A805
R 85
G 1
L A1555
R E5
G 12
L A2305
R E5
G 27
L A56
R 56
G 1
L A806
R 86
G 1
L A1556
R E6
G 12
L A2306
R E6
G 27
L A57
R 57
G 1
L A807
R 87
G 1
L A1557
R E7
G 12
L A2307
R E7
G 27
L A58
R 58
G 1
L A808
R 88
G 1
L A1558
R E8
G 12
L A2308
R E8
G 27
L A59
R 59
G 1
L A809
R 89
G 1
L A1559
R E9
G 12
L A2309
R E9
G 27
L A60
R 60
G 1
L A810
R 90
G 1
L A1560
R E10
G 12
L A2310
R E10
G 27
L A61
R 61
G 1
L A811
R 91
G 1
L A1561
R E11
G 12
L A2311
R E11
G 27
L A62
R 62
G 1
L A812
R 92
G 1
L A1562
R E12
G 12
L A2312
R E12
G 27
L A63
R 63
G 1
L A813
R 93
G 1
L A1563
R E13
G 12
L A2313
R E13
G 27
L A64
R 64
G 1
L A814
R 94
G 1
L A1564
R E14
G 12
L A2314
R E14
G 27
L A65
R 65
G 1
L A815
R 95
G 1
L A1565
R E15
G 12
L A2315
R E15
G 27
L A66
R 66
G 1
L A816
R 96
G 1
L A1566
R E16
G 12
L A2316
R E16
G 27
L A67
R 67
G 1
L A817
R 97
G 1
L A1567
R E17
G 12
L A2317
R E17
G 27
L A68
R 68
G 1
L A818
R 98
G 1
L A1568
R E18
G 12
L A2318
R E18
G 27
L A69
R 69
G 1
L A819
R 99
G 1
L A1569
R E19
G 12
L A2319
R E19
G 27
L A70
R 70
G 1
L A820
R 100
G 1
L A1570
R E20
G 12
L A2320
R E20
G 27
L A71
R 71
G 1
L A821
R 101
G 1
L A1571
R E21
G 12
L A2321
R E21
G 27
L A72
R 72
G 1
L A822
R 102
G 1
L A1572
R E22
G 12
L A2322
R E22
G 27
L A73
R 73
G 1
L A823
R 103
G 1
L A1573
R E23
G 12
L A2323
R E23
G 27
L A74
R 74
G 1
L A824
R 104
G 1
L A1574
R E24
G 12
L A2324
R E24
G 27
L A75
R 75
G 1
L A825
R 105
G 1
L A1575
R E25
G 12
L A2325
R E25
G 27
L A76
R 76
G 1
L A826
R 106
G 1
L A1576
R E26
G 12
L A2326
R E26
G 27
L A77
R 77
G 1
L A827
R 107
G 1
L A1577
R E27
G 12
L A2327
R E27
G 27
L A78
R 78
G 1
L A828
R 108
G 1
L A1578
R E28
G 12
L A2328
R E28
G 27
L A79
R 79
G 1
L A829
R 109
G 1
L A1579
R E29
G 12
L A2329
R E29
G 27
L A80
R 80
G 1
L A830
R 110
G 1
L A1580
R E30
G 12
L A2330
R E30
G 27
L A81
R 1
G 2
L A831
R 111
G 1
L A1581
R E31
G 12
L A2331
R E31
G 27
L A82
R 2
G 2
L A832
R 112
G 1
L A1582
R E32
G 12
L A2332
R E32
G 27
L A83
R 3
G 2
L A833
R 113
G 1
L A1583
R E33
G 12
L A2333
R E33
G 27
L A84
R 4
G 2
L A834
R 114
G 1
L A1584
R E34
G 12
L A2334
R E34
G 27
L A85
R 5
G 2
L A835
R 115
G 1
L A1585
R E35
G 12
L A2335
R E35
G 27
L A86
R 6
G 2
L A836
R 116
G 1
L A1586
R E36
G 12
L A2336
R E36
G 27
L A87
R 7
G 2
L A837
R 117
G 1
L A1587
R E37
G 12
L A2337
R E37
G 27
L A88
R 8
G 2
L A838
R 118
G 1
L A1588
R E38
G 12
L A2338
R E38
G 27
L A89
R 9
G 2
L A839
R 119
G 1
L A1589
R E39
G 12
L A2339
R E39
G 27
L A90
R 10
G 2
L A840
R 120
G 1
L A1590
R E40
G 12
L A2340
R E40
G 27
L A91
R 11
G 2
L A841
R 121
G 1
L A1591
R E41
G 12
L A2341
R E41
G 27
L A92
R 12
G 2
L A842
R 122
G 1
L A1592
R E42
G 12
L A2342
R E42
G 27
L A93
R 13
G 2
L A843
R 123
G 1
L A1593
R E43
G 12
L A2343
R E43
G 27
L A94
R 14
G 2
L A844
R 124
G 1
L A1594
R E44
G 12
L A2344
R E44
G 27
L A95
R 15
G 2
L A845
R 125
G 1
L A1595
R E45
G 12
L A2345
R E45
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R 16
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R 130
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R E40
G 30
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R 1
G 4
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R 131
G 3
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G 15
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L A242
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G 4
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R 132
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R 133
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G 4
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G 4
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L A246
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G 4
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R 136
G 3
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G 4
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G 3
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G 4
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G 4
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R 10
G 4
L A1000
R 140
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L A2500
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R 11
G 4
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G 4
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G 4
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R 60
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G 33
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R 65
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R 135
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R 66
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R 136
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R 67
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R 137
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R 68
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R 69
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R 70
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R 140
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G 33
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R 71
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R 141
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G 33
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R 72
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R 142
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R 73
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R 143
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R 74
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R 144
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R 75
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R 145
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R 76
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R 78
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R 80
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R 29
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R 37
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R 38
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R 39
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R 119
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R 40
G 6
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R 41
G 6
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R 42
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R 43
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R 127
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R 48
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R 128
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R 49
G 6
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R 129
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R 50
G 6
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R 130
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G 34
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R 51
G 6
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R 131
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G 20
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R 52
G 6
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R 132
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R 53
G 6
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R 133
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R 54
G 6
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R 134
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R 55
G 6
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R 135
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R 56
G 6
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R 136
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R 57
G 6
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R 137
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R 58
G 6
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R 138
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R 59
G 6
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R 139
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R 60
G 6
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R 140
G 6
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G 20
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R 61
G 6
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R 141
G 6
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G 20
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R 62
G 6
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R 142
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G 20
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L A463
R 63
G 6
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R 143
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G 20
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L A464
R 64
G 6
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R 144
G 6
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G 20
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L A465
R 65
G 6
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R 145
G 6
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G 20
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R 66
G 6
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R 146
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G 20
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R 67
G 6
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R 147
G 6
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G 20
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R E17
G 35
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R 68
G 6
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G 6
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G 20
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R E18
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R 69
G 6
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R 149
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G 20
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R 70
G 6
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G 20
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R 71
G 6
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R 81
G 7
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G 20
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R 72
G 6
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R 82
G 7
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R 73
G 6
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R 83
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R 74
G 6
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R 84
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R 75
G 6
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R 76
G 6
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R 86
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G 20
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R 77
G 6
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R 78
G 6
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R 88
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R 79
G 6
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R 80
G 6
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R 90
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R 1
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R 91
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G 20
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R 92
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G 20
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R 3
G 7
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R 93
G 7
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G 20
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R E33
G 35
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R 4
G 7
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G 20
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R 5
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R 95
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R 6
G 7
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G 7
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R 8
G 7
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G 20
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R 9
G 7
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G 20
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R 10
G 7
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G 20
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R 11
G 7
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R 12
G 7
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G 20
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R 13
G 7
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G 20
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R 14
G 7
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G 20
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R 15
G 7
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G 20
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R 16
G 7
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G 20
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R 18
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R 21
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R 22
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G 21
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R 23
G 7
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R 24
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G 21
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R 25
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R 26
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R 27
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R 28
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R 29
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R 30
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G 21
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R 31
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G 21
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R 32
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G 21
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R 33
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G 21
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R 34
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G 21
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G 21
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G 21
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R 37
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G 21
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R 38
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G 21
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R 39
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G 21
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R 40
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G 21
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R 41
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R 42
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G 7
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R 50
G 7
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R 140
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R 51
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R 71
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G 9
L A1423
R 143
G 9
L A2173
R E23
G 24
L A2923
R E23
G 39
L A674
R 34
G 9
L A1424
R 144
G 9
L A2174
R E24
G 24
L A2924
R E24
G 39
L A675
R 35
G 9
L A1425
R 145
G 9
L A2175
R E25
G 24
L A2925
R E25
G 39
L A676
R 36
G 9
L A1426
R 146
G 9
L A2176
R E26
G 24
L A2926
R E26
G 39
L A677
R 37
G 9
L A1427
R 147
G 9
L A2177
R E27
G 24
L A2927
R E27
G 39
L A678
R 38
G 9
L A1428
R 148
G 9
L A2178
R E28
G 24
L A2928
R E28
G 39
L A679
R 39
G 9
L A1429
R 149
G 9
L A2179
R E29
G 24
L A2929
R E29
G 39
L A680
R 40
G 9
L A1430
R 150
G 9
L A2180
R E30
G 24
L A2930
R E30
G 39
L A681
R 41
G 9
L A1431
R 81
G 10
L A2181
R E31
G 24
L A2931
R E31
G 39
L A682
R 42
G 9
L A1432
R 82
G 10
L A2182
R E32
G 24
L A2932
R E32
G 39
L A683
R 43
G 9
L A1433
R 83
G 10
L A2183
R E33
G 24
L A2933
R E33
G 39
L A684
R 44
G 9
L A1434
R 84
G 10
L A2184
R E34
G 24
L A2934
R E34
G 39
L A685
R 45
G 9
L A1435
R 85
G 10
L A2185
R E35
G 24
L A2935
R E35
G 39
L A686
R 46
G 9
L A1436
R 86
G 10
L A2186
R E36
G 24
L A2936
R E36
G 39
L A687
R 47
G 9
L A1437
R 87
G 10
L A2187
R E37
G 24
L A2937
R E37
G 39
L A688
R 48
G 9
L A1438
R 88
G 10
L A2188
R E38
G 24
L A2938
R E38
G 39
L A689
R 49
G 9
L A1439
R 89
G 10
L A2189
R E39
G 24
L A2939
R E39
G 39
L A690
R 50
G 9
L A1440
R 90
G 10
L A2190
R E40
G 24
L A2940
R E40
G 39
L A691
R 51
G 9
L A1441
R 91
G 10
L A2191
R E41
G 24
L A2941
R E41
G 39
L A692
R 52
G 9
L A1442
R 92
G 10
L A2192
R E42
G 24
L A2942
R E42
G 39
L A693
R 53
G 9
L A1443
R 93
G 10
L A2193
R E43
G 24
L A2943
R E43
G 39
L A694
R 54
G 9
L A1444
R 94
G 10
L A2194
R E44
G 24
L A2944
R E44
G 39
L A695
R 55
G 9
L A1445
R 95
G 10
L A2195
R E45
G 24
L A2945
R E45
G 39
L A696
R 56
G 9
L A1446
R 96
G 10
L A2196
R E46
G 24
L A2946
R E46
G 39
L A697
R 57
G 9
L A1447
R 97
G 10
L A2197
R E47
G 24
L A2947
R E47
G 39
L A698
R 58
G 9
L A1448
R 98
G 10
L A2198
R E48
G 24
L A2948
R E48
G 39
L A699
R 59
G 9
L A1449
R 99
G 10
L A2199
R E49
G 24
L A2949
R E49
G 39
L A700
R 60
G 9
L A1450
R 100
G 10
L A2200
R E50
G 24
L A2950
R E50
G 39
L A701
R 61
G 9
L A1451
R 101
G 10
L A2201
R E1
G 25
L A2951
R E1
G 40
L A702
R 62
G 9
L A1452
R 102
G 10
L A2202
R E2
G 25
L A2952
R E2
G 40
L A703
R 63
G 9
L A1453
R 103
G 10
L A2203
R E3
G 25
L A2953
R E3
G 40
L A704
R 64
G 9
L A1454
R 104
G 10
L A2204
R E4
G 25
L A2954
R E4
G 40
L A705
R 65
G 9
L A1455
R 105
G 10
L A2205
R E5
G 25
L A2955
R E5
G 40
L A706
R 66
G 9
L A1456
R 106
G 10
L A2206
R E6
G 25
L A2956
R E6
G 40
L A707
R 67
G 9
L A1457
R 107
G 10
L A2207
R E7
G 25
L A2957
R E7
G 40
L A708
R 68
G 9
L A1458
R 108
G 10
L A2208
R E8
G 25
L A2958
R E8
G 40
L A709
R 69
G 9
L A1459
R 109
G 10
L A2209
R E9
G 25
L A2959
R E9
G 40
L A710
R 70
G 9
L A1460
R 110
G 10
L A2210
R E10
G 25
L A2960
R E10
G 40
L A711
R 71
G 9
L A1461
R 111
G 10
L A2211
R E11
G 25
L A2961
R E11
G 40
L A712
R 72
G 9
L A1462
R 112
G 10
L A2212
R E12
G 25
L A2962
R E12
G 40
L A713
R 73
G 9
L A1463
R 113
G 10
L A2213
R E13
G 25
L A2963
R E13
G 40
L A714
R 74
G 9
L A1464
R 114
G 10
L A2214
R E14
G 25
L A2964
R E14
G 40
L A715
R 75
G 9
L A1465
R 115
G 10
L A2215
R E15
G 25
L A2965
R E15
G 40
L A716
R 76
G 9
L A1466
R 116
G 10
L A2216
R E16
G 25
L A2966
R E16
G 40
L A717
R 77
G 9
L A1467
R 117
G 10
L A2217
R E17
G 25
L A2967
R E17
G 40
L A718
R 78
G 9
L A1468
R 118
G 10
L A2218
R E18
G 25
L A2968
R E18
G 40
L A719
R 79
G 9
L A1469
R 119
G 10
L A2219
R E19
G 25
L A2969
R E19
G 40
L A720
R 80
G 9
L A1470
R 120
G 10
L A2220
R E20
G 25
L A2970
R E20
G 40
L A721
R 1
G 10
L A1471
R 121
G 10
L A2221
R E21
G 25
L A2971
R E21
G 40
L A722
R 2
G 10
L A1472
R 122
G 10
L A2222
R E22
G 25
L A2972
R E22
G 40
L A723
R 3
G 10
L A1473
R 123
G 10
L A2223
R E23
G 25
L A2973
R E23
G 40
L A724
R 4
G 10
L A1474
R 124
G 10
L A2224
R E24
G 25
L A2974
R E24
G 40
L A725
R 5
G 10
L A1475
R 125
G 10
L A2225
R E25
G 25
L A2975
R E25
G 40
L A726
R 6
G 10
L A1476
R 126
G 10
L A2226
R E26
G 25
L A2976
R E26
G 40
L A727
R 7
G 10
L A1477
R 127
G 10
L A2227
R E27
G 25
L A2977
R E27
G 40
L A728
R 8
G 10
L A1478
R 128
G 10
L A2228
R E28
G 25
L A2978
R E28
G 40
L A729
R 9
G 10
L A1479
R 129
G 10
L A2229
R E29
G 25
L A2979
R E29
G 40
L A730
R 10
G 10
L A1480
R 130
G 10
L A2230
R E30
G 25
L A2980
R E30
G 40
L A731
R 11
G 10
L A1481
R 131
G 10
L A2231
R E31
G 25
L A2981
R E31
G 40
L A732
R 12
G 10
L A1482
R 132
G 10
L A2232
R E32
G 25
L A2982
R E32
G 40
L A733
R 13
G 10
L A1483
R 133
G 10
L A2233
R E33
G 25
L A2983
R E33
G 40
L A734
R 14
G 10
L A1484
R 134
G 10
L A2234
R E34
G 25
L A2984
R E34
G 40
L A735
R 15
G 10
L A1485
R 135
G 10
L A2235
R E35
G 25
L A2985
R E35
G 40
L A736
R 16
G 10
L A1486
R 136
G 10
L A2236
R E36
G 25
L A2986
R E36
G 40
L A737
R 17
G 10
L A1487
R 137
G 10
L A2237
R E37
G 25
L A2987
R E37
G 40
L A738
R 18
G 10
L A1488
R 138
G 10
L A2238
R E38
G 25
L A2988
R E38
G 40
L A739
R 19
G 10
L A1489
R 139
G 10
L A2239
R E39
G 25
L A2989
R E39
G 40
L A740
R 20
G 10
L A1490
R 140
G 10
L A2240
R E40
G 25
L A2990
R E40
G 40
L A741
R 21
G 10
L A1491
R 141
G 10
L A2241
R E41
G 25
L A2991
R E41
G 40
L A742
R 22
G 10
L A1492
R 142
G 10
L A2242
R E42
G 25
L A2992
R E42
G 40
L A743
R 23
G 10
L A1493
R 143
G 10
L A2243
R E43
G 25
L A2993
R E43
G 40
L A744
R 24
G 10
L A1494
R 144
G 10
L A2244
R E44
G 25
L A2994
R E44
G 40
L A745
R 25
G 10
L A1495
R 145
G 10
L A2245
R E45
G 25
L A2995
R E45
G 40
L A746
R 26
G 10
L A1496
R 146
G 10
L A2246
R E46
G 25
L A2996
R E46
G 40
L A747
R 27
G 10
L A1497
R 147
G 10
L A2247
R E47
G 25
L A2997
R E47
G 40
L A748
R 28
G 10
L A1498
R 148
G 10
L A2248
R E48
G 25
L A2998
R E48
G 40
L A749
R 29
G 10
L A1499
R 149
G 10
L A2249
R E49
G 25
L A2999
R E49
G 40
L A750
R 30
G 10
L A1500
R 150
G 10
L A2250
R E50
G 25
L A3000
R E50
G 40
wherein R 1 to R 80 have the following structures:
wherein R 81 to R 150 have the following structures:
wherein R E1 to R E50 have the following structures:
wherein G 1 to G 40 have the following structures:
9 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
10 . The compound of claim 1 , wherein the compound has a formula of M(L A ) p (L B ) q (L C ) r wherein L B and L C are each a bidentate ligand; and wherein p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p+q+r is the oxidation state of the metal M.
11 . The compound of claim 10 , wherein L B and L C are each independently selected from the group consisting of:
wherein:
T is selected from the group consisting of B, Al, Ga, and In;
each of Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen; Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
R e and R f can be fused or joined to form a ring;
each R a , R b , R c , and R d independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R a1 , R b1 , R c1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and
two adjacent substituents of R a , R b , R c , and R d can be fused or joined to form a ring or form a multidentate ligand.
12 . The compound of claim 10 , wherein L B is selected from the group consisting of L Bk , wherein k is an integer of from 1 to 324, wherein L B1 to L B324 have the following structures:
and
wherein each L Cj-I has a structure based on formula
and
each L Cj-II has a structure based on formula
wherein for each L Cj in L Cj-I and L Cj-II , R 201 and R 202 are each independently defined as in the Table 3 described herein, wherein j is an integer of from 1 to 1416;
wherein R D1 to R D246 have the following structures:
13 . The compound of claim 1 , wherein the compound has the following Formula II:
wherein:
M 1 is Pd or Pt;
rings E and F are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 and Z 2 are each independently C or N;
K 3 and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least one of K 3 and K 4 is a direct bond;
L 1 , L 2 , and L 3 are each independently selected from the group consisting of a single bond, absent a bond, O, S, CR′R″, SiR′R″, BR′, NR′ and ER n , wherein at least one of L 1 and L 2 is present;
X 6 -X 7 are each independently C or N;
R E and R F each independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R′, R″, R E , and R F is independently a hydrogen or a substituent selected from the group consisting of ER n deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and
two substituents can be joined or fused together to form a ring where chemically feasible.
14 . The compound of claim 13 , wherein the compound is selected from the group consisting of:
wherein:
R x and R y are each selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;
R G for each occurrence is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; or
the compound is selected from the group consisting of:
wherein rings A 1 and A 2 are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring.
15 . The compound of claim 13 , wherein the compound is selected from the group consisting of compounds having the formula of Pt(L L )(L 2 )(L R ) with the following structure:
wherein L 1 is L 1 to L 18 , L L and L R are selected from the group consisting of:
L L and L R
Structure
Substituent pattern
L L 1-(i)(j)(k)(l) or L R 1-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 1- (l)(l)(l)(l) to L L 1-(330)(330)(330)(330) or L R 1-(l)(l)(l)(l) to L R 1- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 2-(i)(j)(k)(l) or L R 2-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 2- (l)(l)(l)(l) to L L 2-(330)(330)(330)(330) or L R 2-(l)(l)(l)(l) to L R 2- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 3-(i)(j)(k) or L R 3-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 3- (l)(l)(l) to L L 3-(330)(330)(330) or L R 3-(l)(l)(l) to L R 3- (330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 4-(i)(j) or L R 4-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 4-(l)(l) to L L 4-(330)(330) or L R 4-(l)(l) to L R 4-(330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 5-(i)(j)(k) or L R 5-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 5- (l)(l)(l) to L L 5-(330)(330)(330) or L R 5-(l)(l)(l) to L R 5- (330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 6-(i)(j) or L R 6-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 6-(l)(l) to L L 6-(330)(330) or L R 6-(l)(l) to L R 6-(330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 can equals to ER n in the form of R A1 = ER n ,.
L L 7-(i)(j)(k)(l) or L R 7-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 7- (l)(l)(l)(l) to L L 7-(330)(330)(330)(330) or L R 7-(l)(l)(l)(l) to L R 7- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , R A3 , and R A4 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 4.
L L 8-(i)(j)(k)(l) or L R 8-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 8- (l)(l)(l)(l) to L L 8-(330)(330)(330)(330) or L R 7-(l)(l)(l)(l) to L R 8- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , R A3 , and R A4 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 4.
L L 9-(i)(j)(k) or L R 9-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 9- (l)(l)(l) to L L 9-(330)(330)(330) or L R 9-(l)(l)(l) to L R 9- (330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 10-(i)(j)(k)(l) or L R 10-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 10- (l)(l)(l)(l) to L L 10-(330)(330)(330)(330) or L R 10-(l)(l)(l)(l) to L R 10- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , R A3 , and R A4 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 4.
L L 11-(i)(j)(k)(l) or L R 11-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 11- (l)(l)(l)(l) to L L 11-(330)(330)(330)(330) or L R 11-(l)(l)(l)(l) to L R 11- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 12-(i)(j)(k) or L R 12-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 12- (l)(l)(l) to L L 12-(330)(330)(330) or L R 12-(l)(l)(l) to L R 12- (330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 13-(i)(j)(k) or L R 13-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 13- (l)(l)(l) to L L 13-(330)(330)(330) or L R 13-(l)(l)(l) to L R 13- (330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 14-(i)(j)(k) or L R 14-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 14- (l)(l)(l) to L L 14-(330)(330)(330) or L R 14-(l)(l)(l) to L R 14- (330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 15-(i)(j) or L R 15-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 15-(l)(l) to L L 15-(330)(330) or L R 15-(l)(l) to L R 15-(330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 can equals to ER n in the form of R A1 = ER n
L L 16-(i)(j) or L R 16-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 16-(l)(l) to L L 16-(330)(330) or L R 16-(l)(l) to L R 16-(330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 can equals to ER n in the form of R A1 = ER n
L L 17-(i)(j)(k)(l) or L R 17-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 17- (l)(l)(l)(l) to L L 17-(330)(330)(330)(330) or L R 17-(l)(l)(l)(l) to L R 17- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 18-(i)(j)(k) or L R 18-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 18-(l)(l)(l) to L L 18-(330)(330)(330) or L R 18-(l)(l)(l) to L R 18-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 19-(i)(j) or L R 19-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 19-(l)(l) to L L 19- (330)(330) or L R 19-(l)(l) to L R 19- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 20-(i)(j) or L R 20-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 20-(l)(l) to L L 20- (330)(330) or L R 20-(l)(l) to L R 20- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 21-(i)(j) or L R 21-(i)(j) wherein each of i and j is independently an integer from 1 to 330, wherein L L 21-(l)(l) to L L 21- (330)(330) or L R 21-(l)(l) to L R 21- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 22-(i)(j)(k)(l) or L R 22-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 22- (l)(l)(l)(l) to L L 22-(330)(330)(330)(330) or L R 22-(l)(l)(l)(l) to L R 22- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , R A3 , and R A4 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 4.
L L 23-(i)(j)(k)(l) or L R 23-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 23- (l)(l)(l)(l) to L L 23-(330)(330)(330)(330) or L R 23-(l)(l)(l)(l) to L R 23- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , R A3 , and R A4 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 4.
L L 24-(i)(j)(k)(l) or L R 24-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 24- (l)(l)(l)(l) to L L 24-(330)(330)(330)(330) or L R 24-(l)(l)(l)(l) to L R 24- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 25-(i)(j) or L R 21-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 25-(l)(l) to L L 25- (330)(330) or L R 25-(l)(l) to L R 25- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 26-(i)(j) or L R 26-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 26-(l)(l) to L L 26- (330)(330) or L R 26-(l)(l) to L R 26- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 27-(i)(j) or L R 27-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 27-(l)(l) to L L 27- (330)(330) or L R 27-(l)(l) to L R 27- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 28-(i)(j) or L R 28-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 28-(l)(l) to L L 28- (330)(330) or L R 28-(l)(l) to L R 28- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 29-(i)(j) or L R 29-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 29-(l)(l) to L L 29- (330)(330) or L R 29-(l)(l) to L R 29- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 30-(i)(j) or L R 30-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 30-(l)(l) to L L 30- (330)(330) or L R 30-(l)(l) to L R 30- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 31-(i)(j) or L R 31-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 31-(l)(l) to L L 31- (330)(330) or L R 31-(l)(l) to L R 31- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 32-(i)(j) or L R 32-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 32-(l)(l) to L L 32- (330)(330) or L R 32-(l)(l) to L R 32- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 33-(i)(j) or L R 33-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 33-(l)(l) to L L 33- (330)(330) or L R 33-(l)(l) to L R 33- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 34-(i)(j)(k) or L R 34-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 34-(l)(l)(l) to L L 34-(330)(330)(330) or L R 34-(l)(l)(l) to L R 34-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 35-(i)(j)(k) or L R 35-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 35-(l)(l)(l) to L L 35-(330)(330)(330) or L R 35-(l)(l)(l) to L R 35-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 36-(i)(j)(k) or L R 36-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 34-(l)(l)(l) to L L 36-(330)(330)(330) or L R 36-(l)(l)(l) to L R 36-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 37-(i)(j)(k) or L R 37-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 37-(l)(l)(l) to L L 37-(330)(330)(330) or L R 37-(l)(l)(l) to L R 37-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 38-(i)(j)(k) or L R 38-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 38-(l)(l)(l) to L L 38-(330)(330)(330) or L R 37-(l)(l)(l) to L R 38-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 39-(i)(j)(k) or L R 39-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 39-(l)(l)(l) to L L 39-(330)(330)(330) or L R 39-(l)(l)(l) to L R 39-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 40-(i)(j)(k)(l) or L R 40-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 40- (l)(l)(l)(l) to L L 40-(330)(330)(330)(330) or L R 40-(l)(l)(l)(l) to L R 40- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 41-(i)(j)(k)(l) or L R 41-(i)(j)(k)(1) wherein each of i, j, k, and l, is independently an integer from 1 to 330, wherein L L 41- (l)(l)(l)(l) to L L 41-(330)(330)(330)(330) or L R 41-(l)(l)(l)(l) to L R 41- (330)(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 42-(i)(j) or L R 42-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 42-(l)(l) to L L 42- (330)(330) or L R 42-(l)(l) to L R 42- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 43-(i)(j) or L R 43-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 43-(l)(l) to L L 43- (330)(330) or L R 43-(l)(l) to L R 43- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 44-(i)(j)(k) or L R 44-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 44-(l)(l)(l) to L L 44-(330)(330)(330) or L R 44-(l)(l)(l) to L R 44-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 45-(i)(j)(k) or L R 45-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 45-(l)(l)(l) to L L 45-(330)(330)(330) or L R 45-(l)(l)(l) to L R 45-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
L L 46-(i)(j)(k) or L R 46-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 46-(l)(l)(l) to L L 46-(330)(330)(330) or L R 46-(l)(l)(l) to L R 46-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 47-(i)(j)(k) or L R 47-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 47-(l)(l)(l) to L L 47-(330)(330)(330) or L R 47-(l)(l)(l) to L R 47-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 48-(i)(j)(k) or L R 48-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 48-(l)(l)(l) to L L 48-(330)(330)(330) or L R 48-(l)(l)(l) to L R 48-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 49-(i)(j)(k) or L R 49-(i)(j)(k) wherein each of i, j, and k, is independently an integer from 1 to 330, wherein L L 49-(l)(l)(l) to L L 49-(330)(330)(330) or L R 49-(l)(l)(l) to L R 49-(330)(330)(330) having the structure
wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk, in addition, R A1 , R A2 , and R A3 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 3.
L L 50-(i)(j) or L R 50-(i)(j) wherein each of i, and j is independently an integer from 1 to 330, wherein L L 50-(l)(l) to L L 50- (330)(330) or L R 50-(l)(l) to L R 50- (330)(330) having the structure
wherein R A1 = Ri and R A2 = Rj, in addition, R A1 and R A2 can independently equals to ER n in the form of R Ax = ER n , wherein x in an integer from 1 to 2.
wherein R1 to R330 have the following structures of the List P described herein:
and
L 1 to L 18 have the following structures:
16 . The compound of claim 13 , wherein the compound is selected from the group consisting of:
17 . An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand L A of the following Formula I:
wherein:
rings A and B are each independently a monocyclic or fused multicyclic ring system consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic ring;
X 1 -X 4 are each independently C or N with the proviso that at least two of X 1 -X 4 are C, and the rest of X 1 -X 4 are N;
each R A and R B independently represents mono to the maximum allowable substitution, or no substitution;
K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, and S;
when K 1 is O or S, X 1 is C; when K 2 is O or S, X 3 is C;
L is selected from the group consisting of a direct bond, ER n , S, CR′R″, SiR′R″, BR′, and NR′;
each R A , R B , R′, and R″ is independently a hydrogen or a substituent selected from the group consisting of ER n , deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
at least one of R A , R B , R′, or R″ comprising a substituent ER n wherein the index n is an integer from 1 to 5;
E is selected from the group consisting of Sb, Bi, and Te;
each R can be the same or different;
R can be fused to ring A or ring B to form a five or six-membered ring;
each R is a hydrogen or a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, oxo, and combinations thereof;
if E is a ring atom, then E is a ring atom in a metal chelate with the metal M or E is a ring atom in a 5-membered ring:
L A is coordinated to a metal M through the dashed lines;
M is selected from the group consisting of Os, Ir, Rh, Re, Ru, Pd, Pt, Cu, Ag, and Au;
M can be coordinated to other ligands;
when M is Pt, L A is joined with at least one of the other ligands to comprise a tridentate or tetradentate ligand;
L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two of R A , R B , R, R′, and R″ can be joined or fused to form a ring; and
the compound is a neutral compound.
18 . The OLED of claim 17 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).
19 . The OLED of claim 18 , wherein the host is selected from the group consisting of:
and combinations thereof.
20 . 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, wherein the organic layer comprises a compound comprising a ligand L A of the following Formula I:
wherein:
rings A and B are each independently a monocyclic or fused multicyclic ring system consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic ring;
X 1 -X 4 are each independently C or N with the proviso that at least two of X 1 -X 4 are C, and the rest of X 1 -X 4 are N;
each R A and R B independently represents mono to the maximum allowable substitution, or no substitution;
K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, and S;
when K 1 is O or S, X 1 is C; when K 2 is O or S, X 3 is C;
L is selected from the group consisting of a direct bond, ER n , S, CR′R″, SiR′R″, BR′, and NR′;
each R A , R B , R′, and R″ is independently a hydrogen or a substituent selected from the group consisting of ER n , deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
at least one of R A , R B , R′, or R″ comprising a substituent ER n , wherein n is an integer from 1 to 5;
E is selected from the group consisting of Sb, Bi, and Te;
each R can be the same or different;
R can be fused to ring A or ring B to form a five or six-membered ring;
each R is a hydrogen or a substituent selected from the group consisting of halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, oxo, and combinations thereof;
if E is a ring atom, then E is a ring atom in a metal chelate with the metal M or E is a ring atom in a 5-membered ring:
L A is coordinated to a metal M through the dashed lines;
M is selected from the group consisting of Os, Ir, Rh, Re, Ru, Pd, Pt, Cu, Ag, and Au;
M can be coordinated to other ligands;
when M is Pt, L A is joined with at least one of the other ligands to comprise a tridentate or tetradentate ligand;
L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two of R A , R B , R, R′, and R″ can be joined or fused to form a ring; and
the compound is a neutral compound.