Organic electroluminescent materials and devices

Abstract

A ligand for metal complexes are disclosed, in which an imidazole ring is fused to an aromatic ring as a substituent or an imidazole ring is fused to a six-member ring of the original ligand. The features of these elements within the ligand afford a better device performance in general OLED device.

Claims

1. A compound comprising a first ligand L.sub.A having Formula I, ##STR05764## wherein rings A and B are each a 6-membered carbocyclic or heterocyclic aromatic ring; wherein R.sup.A and R.sup.B each independently represent mono to the possible maximum number of substitution, or no substitution; wherein Z.sup.1 and Z.sup.2 is are each independently selected from the group consisting of carbon or nitrogen; wherein each R.sup.A and R.sup.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 of R.sup.A or R.sup.B comprises an aromatic group further fused by a first group, wherein the aromatic group is fused directly to Ring A or Ring B, respectively; or (2) at least one pair of two adjacent R.sup.A or one pair of two adjacent R.sup.B form the first group fused to ring A or B; wherein the first group is ##STR05765## wherein in (1), * represents the points fused to the aromatic group; and in (2), * represents the points fused to ring A or B, and R.sup.1 and R.sup.2 are joined or fused into a ring when the first group is fused to ring A that is coordinated to a metal M by a N or the first group is fused to ring B that is coordinated to a metal M by a N; wherein, when two R.sup.A are joined or fused to form a 5-membered ring, no R.sup.B comprises a polycyclic heteroaromatic system comprising three or more rings fused together; wherein, when two R.sup.B are joined or fused to form a 5-membered ring, no R.sup.A comprises a polycyclic heteroaromatic system comprising three or more rings fused together; wherein, when Z.sup.1 is N and Z.sup.2 is C, and the first group is fused to Ring B, then R.sup.B is exactly di-substituted; wherein, when Z.sup.1 is C and Z.sup.2 is N, and the first group is fused to Ring A, then R.sup.A is exactly di-substituted; wherein R.sup.1 and R.sup.2 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 R.sup.1 and R.sup.2 are optionally joined or fused into a ring; wherein (a) one of Z.sup.1 and Z.sup.2 is C and the other one of Z.sup.1 and Z.sup.2 is N, or (b) both of R.sup.1 and R.sup.2 are other than H, or (c) both (a) and (b); wherein the ligand L.sub.A is coordinated to a metal M; wherein the metal M can be coordinated to other ligands; and wherein the ligand L.sub.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 one of Z.sup.1 and Z.sup.2 is nitrogen, and one of Z.sup.1 and Z.sup.2 is carbon.

4. The compound of claim 1, wherein i ring A is pyridine, (ii) ring B is benzene, or both (i) and (ii) are true.

5. The compound of claim 1, wherein R.sup.1 and R.sup.2 are each independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.

6. The compound of claim 1, wherein R.sup.1 and R.sup.2 are joined or fused into a ring.

7. The compound of claim 1, wherein ligand L.sub.A is selected from the group consisting of: ##STR05766##

8. The compound of claim 1, wherein the first group is selected from the group consisting of: ##STR05767## ##STR05768## ##STR05769## ##STR05770##

9. The compound of claim 1, wherein ligand L.sub.A is selected from the group consisting of: ##STR05771## and substituted variants thereof; wherein each R.sup.3, R.sup.4, and R.sup.5 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 any adjacent substituents are optionally joined or fused into a ring.

10. The compound of claim 1, wherein the compound has a formula of M(L.sub.A).sub.n(L.sub.B).sub.m-n; wherein M is Ir or Pt; L.sub.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 L.sub.B is selected from the group consisting of: ##STR05772## wherein each X.sup.1 to X.sup.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.sub.2, CR′R″, SiR′R″, and GeR′R″; wherein R′ and R″ are optionally fused or joined to form a ring; wherein each R.sub.a, R.sub.b, R.sub.c, and R.sub.d may represent from mono substitution to the possible maximum number of substitution, or no substitution; wherein R′, R″, R.sub.a, R.sub.b, R.sub.c, and R.sub.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.sub.a, R.sub.b, R.sub.c, and R.sub.d are optionally fused or joined to form a ring or form a multidentate ligand.

12. 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.sub.A having Formula I, ##STR05773## wherein rings A and B are each a 6-membered carbocyclic or heterocyclic aromatic ring; wherein R.sup.A and R.sup.B each independently represent mono to the possible maximum number of substitution, or no substitution; wherein Z.sup.1 and Z.sup.2 is are each independently selected from the group consisting of carbon or nitrogen; wherein each R.sup.A and R.sup.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 of R.sup.A or R.sup.B comprises an aromatic group further fused by a first group, wherein the aromatic group is fused directly to Ring A or Ring B, respectively; or (2) at least one pair of two adjacent R.sup.A or one pair of two adjacent R.sup.B form the first group fused to ring A or B; wherein the first group is ##STR05774## wherein in (1), * represents the points fused to the aromatic group; and in (2), * represents the points fused to ring A or B, and R.sup.1 and R.sup.2 are joined or fused into a ring when the first group is fused to ring A that is coordinated to a metal M by a N or the first group is fused to ring B that is coordinated to a metal M by a N; wherein, when two R.sup.A are joined or fused to form a 5-membered ring, no R.sup.B comprises a polycyclic heteroaromatic system comprising three or more rings fused together; wherein, when two R.sup.B are joined or fused to form a 5-membered ring, no R.sup.A comprises a polycyclic heteroaromatic system comprising three or more rings fused together; wherein, when Z.sup.1 is N and Z.sup.2 is C, and the first group is fused to Ring B, then R.sup.B is exactly di-substituted; wherein, when Z.sup.1 is C and Z.sup.2 is N, and the first group is fused to Ring A, then R.sup.A is exactly di-substituted; wherein R.sup.1 and R.sup.2 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 R.sup.1 and R.sup.2 are optionally joined or fused into a ring; wherein (a) one of Z.sup.1 and Z.sup.2 is C and the other one of Z.sup.1 and Z.sup.2 is N, or (b) both of R.sup.1 and R.sup.2 are other than H, or (c) both (a) and (b); wherein the ligand L.sub.A is coordinated to a metal M; wherein the metal M can be coordinated to other ligands; and wherein the ligand L.sub.A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

13. The OLED of claim 12, 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.

14. The OLED of claim 12, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of: ##STR05775## ##STR05776## ##STR05777## ##STR05778## and combinations thereof.

15. A consumer product comprising an organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand L.sub.A having Formula I, ##STR05779## wherein rings A and B are each a 6-membered carbocyclic or heterocyclic aromatic ring; wherein R.sup.A and R.sup.B each independently represent mono to the possible maximum number of substitution, or no substitution; wherein Z.sup.1 and Z.sup.2 is are each independently selected from the group consisting of carbon or nitrogen; wherein each R.sup.A and R.sup.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 of R.sup.A or R.sup.B comprises an aromatic group further fused by a first group, wherein the aromatic group is fused directly to Ring A or Ring B, respectively; or (2) at least one pair of two adjacent R.sup.A or one pair of two adjacent R.sup.B form the first group fused to ring A or B; wherein the first group is ##STR05780## wherein in (1), * represents the points fused to the aromatic group; and in (2), * represents the points fused to ring A or B, and R.sup.1 and R.sup.2 are joined or fused into a ring when the first group is fused to ring A that is coordinated to a metal M by a N or the first group is fused to ring B that is coordinated to a metal M by a N; wherein, when two R.sup.A are joined or fused to form a 5-membered ring, no R.sup.B comprises a polycyclic heteroaromatic system comprising three or more rings fused together; wherein, when two R.sup.B are joined or fused to form a 5-membered ring, no R.sup.A comprises a polycyclic heteroaromatic system comprising three or more rings fused together; wherein, when Z.sup.1 is N and Z.sup.2 is C, and the first group is fused to Ring B, then R.sup.B is exactly di-substituted; wherein, when Z.sup.1 is C and Z.sup.2 is N, and the first group is fused to Ring A, then R.sup.A is exactly di-substituted; wherein R.sup.1 and R.sup.2 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 R.sup.1 and R.sup.2 are optionally joined or fused into a ring; wherein (a) one of Z.sup.1 and Z.sup.2 is C and the other one of Z.sup.1 and Z.sup.2 is N, or (b) both of R.sup.1 and R.sup.2 are other than H, or (c) both (a) and (b); wherein the ligand L.sub.A is coordinated to a metal M; wherein the metal M can be coordinated to other ligands; and wherein the ligand L.sub.A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

16. The consumer product of claim 15, wherein the consumer product is selected from the group consisting of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, and a sign.

17. The compound of claim 1, wherein ligand L.sub.A is selected from the group consisting of LA1 to LA2891 defined below: TABLE-US-00012 LA1 to LA252 having the following structure embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1 LA2 LA3 LA4 LA5 LA6 LA7 LA8 LA9 LA10 LA11 LA12 LA13 LA14 LA15 LA16 LA17 LA18 LA19 LA20 LA21 LA22 LA23 LA24 LA25 LA26 LA27 LA28 LA29 LA30 LA31 LA32 LA33 embedded image LA34 LA35 LA36 LA37 LA38 LA39 LA40 LA41 LA42 LA43 LA44 LA45 LA46 LA47 LA48 LA49 LA50 LA51 LA52 LA53 LA54 LA55 LA56 LA57 LA58 LA59 LA60 LA61 LA62 LA63 LA64 LA65 LA66 LA67 LA68 LA69 LA70 LA71 LA72 LA73 LA74 embedded image LA75 LA76 LA77 LA78 LA79 LA80 LA81 LA82 LA83 LA84 LA85 LA86 LA87 LA88 LA89 LA90 LA91 LA92 LA93 LA94 LA95 LA96 LA97 LA98 LA99 LA100 LA101 LA102 LA103 LA104 LA105 LA106 LA107 LA108 LA109 LA110 LA111 LA112 LA113 embedded image LA114 LA115 LA116 LA117 LA118 LA119 LA120 LA121 LA122 LA123 LA124 LA125 LA126 LA127 LA128 LA129 LA130 LA131 LA132 LA133 LA134 LA135 LA136 LA137 LA138 LA139 LA140 LA141 LA142 LA143 LA144 LA145 LA146 LA147 LA148 LA149 embedded image LA150 LA151 LA152 LA153 LA154 LA155 LA156 LA157 LA158 LA159 LA160 LA161 LA162 LA163 LA164 LA165 LA166 LA167 LA168 LA169 LA170 LA171 LA172 LA173 LA174 LA175 LA176 LA177 LA178 LA179 LA180 LA181 LA182 LA183 LA184 LA185 embedded image LA186 LA187 LA188 LA189 LA190 LA191 LA192 LA193 LA194 LA195 LA196 LA197 LA198 LA199 LA200 LA201 LA202 LA203 LA204 LA205 LA206 LA207 LA208 LA209 LA210 LA211 LA212 LA213 LA214 LA215 LA216 LA217 LA218 LA219 LA220 LA221 embedded image LA222 LA223 LA224 LA225 LA226 LA227 LA228 LA229 LA230 LA231 LA232 LA233 LA234 LA235 LA236 LA237 LA238 LA239 LA240 LA241 LA242 LA243 LA244 LA245 LA246 LA247 LA248 LA249 LA250 LA251 LA252 TABLE-US-00013 LA253 to LA504 having the following structure embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA253 LA254 LA255 LA256 LA257 LA258 LA259 LA260 LA261 LA262 LA263 LA264 LA265 LA266 LA267 LA268 LA269 LA270 LA271 LA272 LA273 LA274 LA275 LA276 LA277 LA278 LA279 LA280 embedded image LA281 LA282 LA283 LA284 LA285 LA286 LA287 LA288 LA289 LA290 LA291 LA292 LA293 LA294 LA295 LA296 LA297 LA298 LA299 LA300 LA301 LA302 LA303 LA304 LA305 LA306 LA307 LA308 LA309 LA310 LA311 LA312 LA313 LA314 LA315 LA316 embedded image LA317 LA318 LA319 LA320 LA321 LA322 LA323 LA324 LA325 LA326 LA327 LA328 LA329 LA330 LA331 LA332 LA333 LA334 LA335 LA336 LA337 LA338 LA339 LA340 LA341 LA342 LA343 LA344 LA345 LA346 LA347 LA348 LA349 LA350 LA351 LA352 embedded image LA353 LA354 LA355 LA356 LA357 LA358 LA359 LA360 LA361 LA362 LA363 LA364 LA365 LA366 LA367 LA368 LA369 LA370 LA371 LA372 LA373 LA374 LA375 LA376 LA377 LA378 LA379 LA380 LA381 LA382 LA383 LA384 LA385 LA386 LA387 LA388 embedded image LA389 LA390 LA391 LA392 LA393 LA394 LA395 LA396 LA397 LA398 LA399 LA400 LA401 LA402 LA403 LA404 LA405 LA406 LA407 LA408 LA409 LA410 LA411 LA412 LA413 LA414 LA415 LA416 LA417 LA418 LA419 LA420 LA421 LA422 LA423 LA424 embedded image LA425 LA426 LA427 LA428 LA429 LA430 LA431 LA432 LA433 LA434 LA435 LA436 LA437 LA438 LA439 LA440 LA441 LA442 LA443 LA444 LA445 LA446 LA447 LA448 LA449 LA450 LA451 LA452 LA453 LA454 LA455 LA456 LA457 LA458 LA459 LA460 embedded image LA461 LA462 LA463 LA464 LA465 LA466 LA467 LA468 LA469 LA470 LA471 LA472 LA473 LA474 LA475 LA476 LA477 LA478 LA479 LA480 LA481 LA482 LA483 LA484 LA485 LA486 LA487 LA488 LA489 LA490 LA491 LA492 LA493 LA494 LA495 LA496 embedded image LA497 LA498 LA499 LA500 LA501 LA502 LA503 LA504 TABLE-US-00014 LA505 to LA756 having the following structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA505 LA506 LA507 LA508 LA509 LA510 LA511 LA512 LA513 LA514 LA515 LA516 embedded image LA517 LA518 LA519 LA520 LA521 LA522 LA523 LA524 LA525 LA526 LA527 LA528 LA529 LA530 LA531 LA532 LA533 LA534 LA535 LA536 LA537 LA538 LA539 LA540 LA541 LA542 LA543 LA544 LA545 LA546 LA547 LA548 LA549 LA550 LA551 LA552 embedded image LA553 LA554 LA555 LA556 LA557 LA558 LA559 LA560 LA561 LA562 LA563 LA564 LA565 LA566 LA567 LA568 LA569 LA570 LA571 LA572 LA573 LA574 LA575 LA576 LA577 LA578 LA579 LA580 LA581 LA582 LA583 LA584 LA585 LA586 LA587 LA588 embedded image LA589 LA590 LA591 LA592 LA593 LA594 LA595 LA596 LA597 LA598 LA599 LA600 LA601 LA602 LA603 LA604 LA605 LA606 LA607 LA608 LA609 LA610 LA611 LA612 LA613 LA614 LA615 LA616 LA617 LA618 LA619 LA620 LA621 LA622 LA623 LA624 embedded image LA625 LA626 LA627 LA628 LA629 LA630 LA631 LA632 LA633 LA634 LA635 LA636 LA637 LA638 LA639 LA640 LA641 LA642 LA643 LA644 LA645 LA646 LA647 LA648 LA649 LA650 LA651 LA652 LA653 LA654 LA655 LA656 LA657 LA658 LA659 LA660 embedded image LA661 LA662 LA663 LA664 LA665 LA666 LA667 LA668 LA669 LA670 LA671 LA672 LA673 LA674 LA675 LA676 LA677 LA678 LA679 LA680 LA681 LA682 LA683 LA684 LA685 LA686 LA687 LA688 LA689 LA690 LA691 LA692 LA693 LA694 LA695 LA696 embedded image LA697 LA698 LA699 LA700 LA701 LA702 LA703 LA704 LA705 LA706 LA707 LA708 LA709 LA710 LA711 LA712 LA713 LA714 LA715 LA716 LA717 LA718 LA719 LA720 LA721 LA722 LA723 LA724 LA725 LA726 LA727 LA728 LA729 LA730 LA731 LA732 embedded image LA733 LA734 LA735 LA736 LA737 LA738 LA739 LA740 LA741 LA742 LA743 LA744 LA745 LA746 LA747 LA748 LA749 LA750 LA751 LA752 LA753 LA754 LA755 LA756 TABLE-US-00015 ID R.sup.1 R.sup.2 LA757 LA758 LA759 LA760 LA761 LA762 LA763 embedded image LA764 LA765 LA766 LA767 LA768 LA769 LA770 LA771 LA772 LA773 LA774 LA775 LA776 LA777 LA778 LA779 LA780 LA781 LA782 LA783 LA784 LA785 LA786 LA787 LA788 LA789 LA790 LA791 LA792 LA793 LA794 LA795 LA796 LA797 LA798 LA799 embedded image LA800 LA801 LA802 LA803 LA804 LA805 LA806 LA807 LA808 LA809 LA810 LA811 LA812 LA813 LA814 LA815 LA816 LA817 LA818 LA819 LA820 LA821 LA822 LA823 LA824 LA825 LA826 LA827 LA828 LA829 LA830 LA831 LA832 LA833 LA834 LA835 embedded image LA836 LA837 LA838 LA839 LA840 LA841 LA842 LA843 LA844 LA845 LA846 LA847 LA848 LA849 LA850 LA851 LA852 LA853 LA854 LA855 LA856 LA857 LA858 LA859 LA860 LA861 LA862 LA863 LA864 LA865 LA866 LA867 LA868 LA869 LA870 LA871 embedded image LA872 LA873 LA874 LA875 LA876 LA877 LA878 LA879 LA880 LA881 LA882 LA883 LA884 LA885 LA886 LA887 LA888 LA889 LA890 LA891 LA892 LA893 LA894 LA895 LA896 LA897 LA898 LA899 LA900 LA901 LA902 LA903 LA904 LA905 LA906 LA907 embedded image LA908 LA909 LA910 LA911 LA912 LA913 LA914 LA915 LA916 LA917 LA918 LA919 LA920 LA921 LA922 LA923 LA924 LA925 LA926 LA927 LA928 LA929 LA930 LA931 LA932 LA933 LA934 LA935 LA936 LA937 LA938 LA939 LA940 LA941 LA942 LA943 embedded image LA944 LA945 LA946 LA947 LA948 LA949 LA950 LA951 LA952 LA953 LA954 LA955 LA956 LA957 LA958 LA959 LA960 LA961 LA962 LA963 LA964 LA965 LA966 LA967 LA968 LA969 LA970 LA971 LA972 LA973 LA974 LA975 LA976 LA977 LA978 LA979 embedded image LA980 LA981 LA982 LA983 LA984 LA985 LA986 LA987 LA988 LA989 LA990 LA991 LA992 LA993 LA994 LA995 LA996 LA997 LA998 LA999 LA1000 LA1001 LA1002 LA1003 LA1004 LA1005 LA1006 LA1007 LA1008 TABLE-US-00016 LA1009 to LA1260 having the following structure embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1009 LA1010 LA1011 LA1012 LA1013 LA1014 LA1015 LA1016 LA1017 LA1018 LA1019 LA1020 LA1021 LA1022 LA1023 LA1024 LA1025 LA1026 LA1027 LA1028 LA1029 LA1030 LA1031 LA1032 LA1033 embedded image LA1034 LA1035 LA1036 LA1037 LA1038 LA1039 LA1040 LA1041 LA1042 LA1043 LA1044 LA1045 LA1046 LA1047 LA1048 LA1049 LA1050 LA1051 LA1052 LA1053 LA1054 LA1055 LA1056 LA1057 LA1058 LA1059 LA1060 LA1061 LA1062 LA1063 LA1064 LA1065 embedded image LA1066 LA1067 LA1068 LA1069 LA1070 LA1071 LA1072 LA1073 LA1074 LA1075 LA1076 LA1077 LA1078 LA1079 LA1080 LA1081 LA1082 LA1083 LA1084 LA1085 LA1086 LA1087 LA1088 LA1089 LA1090 LA1091 LA1092 LA1093 LA1094 LA1095 LA1096 LA1097 embedded image LA1098 LA1099 LA1100 LA1101 LA1102 LA1103 LA1104 LA1105 LA1106 LA1107 LA1108 LA1109 LA1110 LA1111 LA1112 LA1113 LA1114 LA1115 LA1116 LA1117 LA1118 LA1119 LA1120 LA1121 LA1122 LA1123 LA1124 LA1125 LA1126 LA1127 LA1128 LA1129 embedded image LA1130 LA1131 LA1132 LA1133 LA1134 LA1135 LA1136 LA1137 LA1138 LA1139 LA1140 LA1141 LA1142 LA1143 LA1144 LA1145 LA1146 LA1147 LA1148 LA1149 LA1150 LA1151 LA1152 LA1153 LA1154 LA1155 LA1156 LA1157 LA1158 LA1159 LA1160 LA1161 embedded image LA1162 LA1163 LA1164 LA1165 LA1166 LA1167 LA1168 LA1169 LA1170 LA1171 LA1172 LA1173 LA1174 LA1175 LA1176 LA1177 LA1178 LA1179 LA1180 LA1181 LA1182 LA1183 LA1184 LA1185 LA1186 LA1187 LA1188 LA1189 LA1190 LA1191 LA1192 LA1193 embedded image LA1194 LA1195 LA1196 LA1197 LA1198 LA1199 LA1200 LA1201 LA1202 LA1203 LA1204 LA1205 LA1206 LA1207 LA1208 LA1209 LA1210 LA1211 LA1212 LA1213 LA1214 LA1215 LA1216 LA1217 LA1218 LA1219 LA1220 LA1221 LA1222 LA1223 LA1224 LA1225 embedded image LA1226 LA1227 LA1228 LA1229 LA1230 LA1231 LA1232 LA1233 LA1234 LA1235 LA1236 LA1237 LA1238 LA1239 LA1240 LA1241 LA1242 LA1243 LA1244 LA1245 LA1246 LA1247 LA1248 LA1249 LA1250 LA1251 LA1252 LA1253 LA1254 LA1255 LA1256 LA1257 embedded image LA1258 LA1259 LA1260 TABLE-US-00017 LA1261 to LA1512 having the following structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1261 LA1262 LA1263 LA1264 LA1265 LA1266 LA1267 LA1268 LA1269 LA1270 LA1271 LA1272 LA1273 LA1274 embedded image LA1275 LA1276 LA1277 LA1278 LA1279 LA1280 LA1281 LA1282 LA1283 LA1284 LA1285 LA1286 LA1287 LA1288 LA1289 LA1290 LA1291 LA1292 LA1293 LA1294 LA1295 LA1296 LA1297 LA1298 LA1299 LA1300 LA1301 LA1302 LA1303 LA1304 LA1305 LA1306 embedded image LA1307 LA1308 LA1309 LA1310 LA1311 LA1312 LA1313 LA1314 LA1315 LA1316 LA1317 LA1318 LA1319 LA1320 LA1321 LA1322 LA1323 LA1324 LA1325 LA1326 LA1327 LA1328 LA1329 LA1330 LA1331 LA1332 LA1333 LA1334 LA1335 LA1336 LA1337 LA1338 embedded image LA1139 LA1340 LA1341 LA1342 LA1343 LA1344 LA1345 LA1346 LA1347 LA1348 LA1349 LA1350 LA1351 LA1352 LA1353 LA1354 LA1355 LA1356 LA1357 LA1358 LA1359 LA1360 LA1361 LA1362 LA1363 LA1364 LA1365 LA1366 LA1367 LA1368 LA1369 LA1370 embedded image LA1371 LA1372 LA1373 LA1374 LA1375 LA1376 LA1377 LA1378 LA1379 LA1380 LA1381 LA1382 LA1383 LA1384 LA1385 LA1386 LA1387 LA1388 LA1389 LA1390 LA1391 LA1392 LA1393 LA1394 LA1395 LA1396 LA1397 LA1398 LA1399 LA1400 LA1401 LA1402 embedded image LA1403 LA1404 LA1405 LA1406 LA1407 LA1408 LA1409 LA1410 LA1411 LA1412 LA1413 LA1414 LA1415 LA1416 LA1417 LA1418 LA1419 LA1420 LA1421 LA1422 LA1423 LA1424 LA1425 LA1426 LA1427 LA1428 LA1429 LA1430 LA1431 LA1432 LA1433 LA1434 embedded image LA1435 LA1436 LA1437 LA1438 LA1439 LA1440 LA1441 LA1442 LA1443 LA1444 LA1445 LA1446 LA1447 LA1448 LA1449 LA1450 LA1451 LA1452 LA1453 LA1454 LA1455 LA1456 LA1457 LA1458 LA1459 LA1460 LA1461 LA1462 LA1463 LA1464 LA1465 LA1466 embedded image LA1467 LA1468 LA1469 LA1470 LA1471 LA1472 LA1473 LA1474 LA1475 LA1476 LA1477 LA1478 LA1479 LA1480 LA1481 LA1482 LA1483 LA1484 LA1485 LA1486 LA1487 LA1488 LA1489 LA1490 LA1491 LA1492 LA1493 LA1494 LA1495 LA1496 LA1497 LA1498 embedded image LA1499 LA1500 LA1501 LA1502 LA1503 LA1504 LA1505 LA1506 LA1507 LA1508 LA1509 LA1510 LA1511 LA1512 TABLE-US-00018 LA1513 to LA1764 having the following structure wherein R.sup.1and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1513 LA1514 LA1515 LA1516 embedded image LA1517 LA1518 LA1519 LA1520 LA1521 LA1522 LA1523 LA1524 LA1525 LA1526 LA1527 LA1528 LA1529 LA1530 LA1531 LA1532 LA1533 LA1534 LA1535 LA1536 LA1537 LA1538 LA1539 LA1540 LA1541 LA1542 LA1543 LA1544 LA1545 LA1546 LA1547 LA1548 embedded image LA1549 LA1550 LA1551 LA1552 LA1553 LA1554 LA1555 LA1556 LA1557 LA1558 LA1559 LA1560 LA1561 LA1562 LA1563 LA1564 LA1565 LA1566 LA1567 LA1568 LA1569 LA1570 LA1571 LA1572 LA1573 LA1574 LA1575 LA1576 LA1577 LA1578 LA1579 LA1580 embedded image LA1581 LA1582 LA1583 LA1584 LA1585 LA1586 LA1587 LA1588 LA1589 LA1590 LA1591 LA1592 LA1593 LA1594 LA1595 LA1596 LA1597 LA1598 LA1599 LA1600 LA1601 LA1602 LA1603 LA1604 LA1605 LA1606 LA1607 LA1608 LA1609 LA1610 LA1611 LA1612 embedded image LA1613 LA1614 LA1615 LA1616 LA1617 LA1618 LA1619 LA1620 LA1621 LA1622 LA1623 LA1624 LA1625 LA1626 LA1627 LA1628 LA1629 LA1630 LA1631 LA1632 LA1633 LA1634 LA1635 LA1636 LA1637 LA1638 LA1639 LA1640 LA1641 LA1642 LA1643 LA1644 embedded image LA1645 LA1646 LA1647 LA1648 LA1649 LA1650 LA1651 LA1652 LA1653 LA1654 LA1655 LA1656 LA1657 LA1658 LA1659 LA1660 LA1661 LA1662 LA1663 LA1664 LA1665 LA1666 LA1667 LA1668 LA1669 LA1670 LA1671 LA1672 LA1673 LA1674 LA1675 LA1676 embedded image LA1677 LA1678 LA1679 LA1680 LA1681 LA1682 LA1683 LA1684 LA1685 LA1686 LA1687 LA1688 LA1689 LA1690 LA1691 LA1692 LA1693 LA1694 LA1695 LA1696 LA1697 LA1698 LA1699 LA1700 LA1701 LA1702 LA1703 LA1704 LA1705 LA1706 LA1707 LA1708 embedded image LA1709 LA1710 LA1711 LA1712 LA1713 LA1714 LA1715 LA1716 LA1717 LA1718 LA1719 LA1720 LA1721 LA1722 LA1723 LA1724 LA1725 LA1726 LA1727 LA1728 LA1729 LA1730 LA1731 LA1732 LA1733 LA1734 LA1735 LA1736 LA1737 LA1738 LA1739 LA1740 embedded image LA1741 LA1742 LA1743 LA1744 LA1745 LA1746 LA1747 LA1748 LA1749 LA1750 LA1751 LA1752 LA1753 LA1754 LA1755 LA1756 LA1757 LA1758 LA1759 LA1760 LA1761 LA1762 LA1763 LA1764 TABLE-US-00019 LA1765 to LA2016 having the following structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1765 embedded image LA1766 LA1767 LA1768 LA1769 LA1770 LA1771 LA1772 LA1773 LA1774 LA1775 LA1776 LA1777 LA1778 LA1779 LA1780 LA1781 LA1782 LA1783 LA1784 LA1785 LA1786 LA1787 LA1788 LA1789 LA1790 LA1791 LA1792 LA1793 LA1794 LA1795 LA1796 LA1797 embedded image LA1798 LA1799 LA1800 LA1801 LA1802 LA1803 LA1804 LA1805 LA1806 LA1807 LA1808 LA1809 LA1810 LA1811 LA1812 LA1813 LA1814 LA1815 LA1816 LA1817 LA1818 LA1819 LA1820 LA1821 LA1822 LA1823 LA1824 LA1825 LA1826 LA1827 LA1828 LA1829 embedded image LA1830 LA1831 LA1832 LA1833 LA1834 LA1835 LA1836 LA1837 LA1838 LA1839 LA1840 LA1841 LA1842 LA1843 LA1844 LA1845 LA1846 LA1847 LA1848 LA1849 LA1850 LA1851 LA1852 LA1853 LA1854 LA1855 LA1856 LA1857 LA1858 LA1859 LA1860 LA1861 embedded image LA1862 LA1863 LA1864 LA1865 LA1866 LA1867 LA1868 LA1869 LA1870 LA1871 LA1872 LA1873 LA1874 LA1875 LA1876 LA1877 LA1878 LA1879 LA1880 LA1881 LA1882 LA1883 LA1884 LA1885 LA1886 LA1887 LA1888 LA1889 LA1890 LA1891 LA1892 LA1893 embedded image LA1894 LA1895 LA1896 LA1897 LA1898 LA1899 LA1900 LA1901 LA1902 LA1903 LA1904 LA1905 LA1906 LA1907 LA1908 LA1909 LA1910 LA1911 LA1912 LA1913 LA1914 LA1915 LA1916 LA1917 LA1918 LA1919 LA1920 LA1921 LA1922 LA1923 LA1924 LA1925 embedded image LA1926 LA1927 LA1928 LA1929 LA1930 LA1931 LA1932 LA1933 LA1934 LA1935 LA1936 LA1937 LA1938 LA1939 LA1940 LA1941 LA1942 LA1943 LA1944 LA1945 LA1946 LA1947 LA1948 LA1949 LA1950 LA1951 LA1952 LA1953 LA1954 LA1955 LA1956 LA1957 embedded image LA1958 LA1959 LA1960 LA1961 LA1962 LA1963 LA1964 LA1965 LA1966 LA1967 LA1968 LA1969 LA1970 LA1971 LA1972 LA1973 LA1974 LA1975 LA1976 LA1977 LA1978 LA1979 LA1980 LA1981 LA1982 LA1983 LA1984 LA1985 LA1986 LA1987 LA1988 LA1989 embedded image LA1990 LA1991 LA1992 LA1993 LA1994 LA1995 LA1996 LA1997 LA1998 LA1999 LA2000 LA2001 LA2002 LA2003 LA2004 LA2005 LA2006 LA2007 LA2008 LA2009 LA2010 LA2011 LA2012 LA2013 LA2014 LA2015 LA2016 TABLE-US-00020 LA2017 to LA2268 having the following structure embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA2017 LA2018 LA2019 LA2020 LA2021 LA2022 LA2023 LA2024 LA2025 LA2026 LA2027 LA2028 LA2029 LA2030 LA2031 LA2032 LA2033 LA2034 LA2035 LA2036 LA2037 LA2038 LA2039 LA2040 LA2041 embedded image LA2042 LA2043 LA2044 LA2045 LA2046 LA2047 LA2048 LA2049 LA2050 LA2051 LA2052 LA2053 LA2054 LA2055 LA2056 LA2057 LA2058 LA2059 LA2060 LA2061 LA2062 LA2063 LA2064 LA2065 LA2066 LA2067 LA2068 LA2069 LA2070 LA2071 LA2072 LA2073 embedded image LA2074 LA2075 LA2076 LA2077 LA2078 LA2079 LA2080 LA2081 LA2082 LA2083 LA2084 LA2085 LA2086 LA2087 LA2088 LA2089 LA2090 LA2091 LA2092 LA2093 LA2094 LA2095 LA2096 LA2097 LA2098 LA2099 LA2100 LA2101 LA2102 LA2103 LA2104 LA2105 embedded image LA2106 LA2107 LA2108 LA2109 LA2110 LA2111 LA2112 LA2113 LA2114 LA2115 LA2116 LA2117 LA2118 LA2119 LA2120 LA2121 LA2122 LA2123 LA2124 LA2125 LA2126 LA2127 LA2128 LA2129 LA2130 LA2131 LA2132 LA2133 LA2134 LA2135 LA2136 LA2137 embedded image LA2138 LA2139 LA2140 LA2141 LA2142 LA2143 LA2144 LA2145 LA2146 LA2147 LA2148 LA2149 LA2150 LA2151 LA2152 LA2153 LA2154 LA2155 LA2156 LA2157 LA2158 LA2159 LA2160 LA2161 LA2162 LA2163 LA2164 LA2165 LA2166 LA2167 LA2168 LA2169 embedded image LA2170 LA2171 LA2172 LA2173 LA2174 LA2175 LA2176 LA2177 LA2178 LA2179 LA2180 LA2181 LA2182 LA2183 LA2184 LA2185 LA2186 LA2187 LA2188 LA2189 LA2190 LA2191 LA2192 LA2193 LA2194 LA2195 LA2196 LA2197 LA2198 LA2199 LA2200 LA2201 embedded image LA2202 LA2203 LA2204 LA2205 LA2206 LA2207 LA2208 LA2209 LA2210 LA2211 LA2212 LA2213 LA2214 LA2215 LA2216 LA2217 LA2218 LA2219 LA2220 LA2221 LA2222 LA2223 LA2224 LA2225 LA2226 LA2227 LA2228 LA2229 LA2230 LA2231 LA2232 LA2233 embedded image LA2234 LA2235 LA2236 LA2237 LA2238 LA2239 LA2240 LA2241 LA2242 LA2243 LA2244 LA2245 LA2246 LA2247 LA2248 LA2249 LA2250 LA2251 LA2252 LA2253 LA2254 LA2255 LA2256 LA2257 LA2258 LA2259 LA2260 LA2261 LA2262 LA2263 LA2264 LA2265 embedded image LA2266 LA2267 LA2268 TABLE-US-00021 LA2269 to LA2520 having the following structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA2269 LA2270 LA2271 LA2272 LA2273 LA2274 LA2275 LA2276 LA2277 LA2278 LA2279 LA2280 LA2281 LA2282 embedded image LA2283 LA2284 LA2285 LA2286 LA2287 LA2288 LA2289 LA2290 LA2291 LA2292 LA2293 LA2294 LA2295 LA2296 LA2297 LA2298 LA2299 LA2300 LA2301 LA2302 LA2303 LA2304 LA2305 LA2306 LA2307 LA2308 LA2309 LA2310 LA2311 LA2312 LA2313 LA2314 embedded image LA2315 LA2316 LA2317 LA2318 LA2319 LA2320 LA2321 LA2322 LA2323 LA2324 LA2325 LA2326 LA2327 LA2328 LA2329 LA2330 LA2331 LA2332 LA2333 LA2334 LA2335 LA2336 LA2337 LA2338 LA2339 LA2340 LA2341 LA2342 LA2343 LA2344 LA2345 LA2346 embedded image LA2347 LA2348 LA2349 LA2350 LA2351 LA2352 LA2353 LA2354 LA2355 LA2356 LA2357 LA2358 LA2359 LA2360 LA2361 LA2362 LA2363 LA2364 LA2365 LA2366 LA2367 LA2368 LA2369 LA2370 LA2371 LA2372 LA2373 LA2374 LA2375 LA2376 LA2377 LA2378 embedded image LA2379 LA2380 LA2381 LA2382 LA2383 LA2384 LA2385 LA2386 LA2387 LA2388 LA2389 LA2390 LA2391 LA2392 LA2393 LA2394 LA2395 LA2396 LA2397 LA2398 LA2399 LA2400 LA2401 LA2402 LA2403 LA2404 LA2405 LA2406 LA2407 LA2408 LA2409 LA2410 embedded image LA2411 LA2412 LA2413 LA2414 LA2415 LA2416 LA2417 LA2418 LA2419 LA2420 LA2421 LA2422 LA2423 LA2424 LA2425 LA2426 LA2427 LA2428 LA2429 LA2430 LA2431 LA2432 LA2433 LA2434 LA2435 LA2436 LA2437 LA2438 LA2439 LA2440 LA2441 LA2442 embedded image LA2443 LA2444 LA2445 LA2446 LA2447 LA2448 LA2449 LA2450 LA2451 LA2452 LA2453 LA2454 LA2455 LA2456 LA2457 LA2458 LA2459 LA2460 LA2461 LA2462 LA2463 LA2464 LA2465 LA2466 LA2467 LA2468 LA2469 LA2470 LA2471 LA2472 LA2473 LA2474 embedded image LA2475 LA2476 LA2477 LA2478 LA2479 LA2480 LA2481 LA2482 LA2483 LA2484 LA2485 LA2486 LA2487 LA2488 LA2489 LA2490 LA2491 LA2492 LA2493 LA2494 LA2495 LA2496 LA2497 LA2498 LA2499 LA2500 LA2501 LA2502 LA2503 LA2504 LA2505 LA2506 embedded image LA2507 LA2508 LA2509 LA2510 LA2511 LA2512 LA2513 LA2514 LA2515 LA2516 LA2517 LA2518 LA2519 LA2520 TABLE-US-00022 LA2521 to LA2772 having the following structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA2521 LA2522 LA2523 embedded image LA2524 LA2525 LA2526 LA2527 LA2528 LA2529 LA2530 LA2531 LA2532 LA2533 LA2534 LA2535 LA2536 LA2537 LA2538 LA2539 LA2540 LA2541 LA2542 LA2543 LA2544 LA2545 LA2546 LA2547 LA2548 LA2549 LA2550 LA2551 LA2552 LA2553 LA2554 LA2555 embedded image LA2556 LA2557 LA2558 LA2559 LA2560 LA2561 LA2562 LA2563 LA2564 LA2565 LA2566 LA2567 LA2568 LA2569 LA2570 LA2571 LA2572 LA2573 LA2574 LA2575 LA2576 LA2577 LA2578 LA2579 LA2580 LA2581 LA2582 LA2583 LA2584 LA2585 LA2586 LA2587 embedded image LA2588 LA2589 LA2590 LA2591 LA2592 LA2593 LA2594 LA2595 LA2596 LA2597 LA2598 LA2599 LA2600 LA2601 LA2602 LA2603 LA2604 LA2605 LA2606 LA2607 LA2608 LA2609 LA2610 LA2611 LA2612 LA2613 LA2614 LA2615 LA2616 LA2617 LA2618 LA2619 embedded image LA2620 LA2621 LA2622 LA2623 LA2624 LA2625 LA2626 LA2627 LA2628 LA2629 LA2630 LA2631 LA2632 LA2633 LA2634 LA2635 LA2636 LA2637 LA2638 LA2639 LA2640 LA2641 LA2642 LA2643 LA2644 LA2645 LA2646 LA2647 LA2648 LA2649 LA2650 LA2651 embedded image LA2652 LA2653 LA2654 LA2655 LA2656 LA2657 LA2658 LA2659 LA2660 LA2661 LA2662 LA2663 LA2664 LA2665 LA2666 LA2667 LA2668 LA2669 LA2670 LA2671 LA2672 LA2673 LA2674 LA2675 LA2676 LA2677 LA2678 LA2679 LA2680 LA2681 LA2682 LA2683 embedded image LA2684 LA2685 LA2686 LA2687 LA2688 LA2689 LA2690 LA2691 LA2692 LA2693 LA2694 LA2695 LA2696 LA2697 LA2698 LA2699 LA2700 LA2701 LA2702 LA2703 LA2704 LA2705 LA2706 LA2707 LA2708 LA2709 LA2710 LA2711 LA2712 LA2713 LA2714 LA2715 embedded image LA2716 LA2717 LA2718 LA2719 LA2720 LA2721 LA2722 LA2723 LA2724 LA2725 LA2726 LA2727 LA2728 LA2729 LA2730 LA2731 LA2732 LA2733 LA2734 LA2735 LA2736 LA2737 LA2738 LA2739 LA2740 LA2741 LA2742 LA2743 LA2744 LA2745 LA2746 LA2747 embedded image LA2748 LA2749 LA2750 LA2751 LA2752 LA2753 LA2754 LA2755 LA2756 LA2757 LA2758 LA2759 LA2760 LA2761 LA2762 LA2763 LA2764 LA2765 LA2766 LA2767 LA2768 LA2769 LA2770 LA2771 LA2772 ##STR11336## ##STR11337## ##STR11338## ##STR11339## ##STR11340## ##STR11341## ##STR11342## ##STR11343## ##STR11344## ##STR11345## ##STR11346## ##STR11347## ##STR11348## ##STR11349## ##STR11350## ##STR11351## ##STR11352## ##STR11353## ##STR11354## ##STR11355## ##STR11356## ##STR11357## ##STR11358## ##STR11359## ##STR11360## ##STR11361## ##STR11362##

18. The compound of claim 17, wherein the compound is the Compound Ax having the formula Ir(L.sub.Ai).sub.2(L.sub.Cj); wherein x=17i+j-17; i is an integer from 1 to 1512 and 2269 to 2891, and j is an integer from 1 to 17; and wherein L.sub.C is selected from the group consisting of: ##STR11363## ##STR11364## ##STR11365##

19. The compound of claim 17, wherein the compound is the Compound By having the formula Ir(L.sub.Ai)(L.sub.Bk).sub.2; wherein y=300i+k-300; i is an integer from 1 to 1512 and 2269 to 2891 and k is an integer from 1 to 300; and wherein L.sub.B is selected from the group consisting of: ##STR11366## ##STR11367## ##STR11368## ##STR11369## ##STR11370## ##STR11371## ##STR11372## ##STR11373## ##STR11374## ##STR11375## ##STR11376## ##STR11377## ##STR11378## ##STR11379## ##STR11380## ##STR11381## ##STR11382## ##STR11383## ##STR11384## ##STR11385## ##STR11386## ##STR11387## ##STR11388## ##STR11389## ##STR11390## ##STR11391## ##STR11392## ##STR11393## ##STR11394## ##STR11395## ##STR11396## ##STR11397## ##STR11398## ##STR11399## ##STR11400## ##STR11401## ##STR11402## ##STR11403## ##STR11404## ##STR11405## ##STR11406## ##STR11407## ##STR11408## ##STR11409## ##STR11410## ##STR11411## ##STR11412## ##STR11413## ##STR11414## ##STR11415## ##STR11416## ##STR11417## ##STR11418## ##STR11419## ##STR11420## ##STR11421## ##STR11422## ##STR11423## ##STR11424## ##STR11425## ##STR11426## ##STR11427## ##STR11428## ##STR11429## ##STR11430##

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 shows an organic light emitting device.

(2) FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.

DETAILED DESCRIPTION

(3) Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.

(4) The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.

(5) More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 151-154, 1998; (“Baldo-I”) and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.

(6) FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.

(7) More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

(8) FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.

(9) The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.

(10) Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.

(11) Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processability than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

(12) Devices fabricated in accordance with embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge. The barrier layer may comprise a single layer, or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

(13) Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. A consumer product comprising an OLED that includes the compound of the present disclosure in the organic layer in the OLED is disclosed. Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays. Some examples of such consumer products include 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 (displays that are less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, and a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from −40 degree C. to +80 degree C.

(14) The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.

(15) The term “halo,” “halogen,” or “halide” as used herein includes fluorine, chlorine, bromine, and iodine.

(16) The term “alkyl” as used herein contemplates both straight and branched chain alkyl radicals. Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group may be optionally substituted.

(17) The term “cycloalkyl” as used herein contemplates cyclic alkyl radicals. Preferred cycloalkyl groups are those containing 3 to 10 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, and the like. Additionally, the cycloalkyl group may be optionally substituted.

(18) The term “alkenyl” as used herein contemplates both straight and branched chain alkene radicals. Preferred alkenyl groups are those containing two to fifteen carbon atoms. Additionally, the alkenyl group may be optionally substituted.

(19) The term “alkynyl” as used herein contemplates both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may be optionally substituted.

(20) The terms “aralkyl” or “arylalkyl” as used herein are used interchangeably and contemplate an alkyl group that has as a substituent an aromatic group. Additionally, the aralkyl group may be optionally substituted.

(21) The term “heterocyclic group” as used herein contemplates aromatic and non-aromatic cyclic radicals. Hetero-aromatic cyclic radicals also means heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 to 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers, such as tetrahydrofuran, tetrahydropyran, and the like. Additionally, the heterocyclic group may be optionally substituted.

(22) The term “aryl” or “aromatic group” as used herein contemplates single-ring groups and polycyclic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may be optionally substituted.

(23) The term “heteroaryl” as used herein contemplates single-ring hetero-aromatic groups that may include from one to five heteroatoms. The term heteroaryl also includes polycyclic hetero-aromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.

(24) The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl may be unsubstituted or may be substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

(25) As used herein, “substituted” indicates that a substituent other than H is bonded to the relevant position, such as carbon. Thus, for example, where R.sup.1 is mono-substituted, then one R.sup.1 must be other than H. Similarly, where R.sup.1 is di-substituted, then two of R.sup.1 must be other than H. Similarly, where R.sup.1 is unsubstituted, R.sup.1 is hydrogen for all available positions.

(26) The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective fragment can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.

(27) It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.

(28) A compound comprising a first ligand L.sub.A having a structure according to Formula I

(29) ##STR00004##
is disclosed. In Formula I, rings A and B are each a 6-membered carbocyclic or heterocyclic ring; R.sup.A and R.sup.B each independently represent mono to the possible maximum number of substitution, or no substitution; Z.sup.1 and Z.sup.2 are each independently selected from the group consisting of carbon or nitrogen; each R.sup.A and R.sup.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;

(30) wherein (1) at least one of R.sup.A or R.sup.B comprises an aromatic group further fused by a first group; or (2) at least one pair of two adjacent R.sup.A or one pair of two adjacent R.sup.B form the first group fused to ring A or B;

(31) ##STR00005##
wherein the first group is; wherein in (1), * represents the points fused to the aromatic group; and in (2), * represents the points fused to ring A or B, and the rings to which the first group is fused is not pyridine when R.sup.1 and R.sup.2 are not joined or fused into a ring; wherein R.sup.1 and R.sup.2 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 R.sup.1 and R.sup.2 are optionally joined or fused into a ring;

(32) wherein the ligand L.sub.A is coordinated to a metal M;

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

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

(35) In some embodiments of the compound, M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In some embodiments, M is Ir or Pt.

(36) In some embodiments, the compound is homoleptic. In some embodiments, the compound is heteroleptic.

(37) In some embodiments of the compound, one of Z.sup.1 and Z.sup.2 is nitrogen, and one of Z.sup.1 and Z.sup.2 is carbon.

(38) In some embodiments of the compound, ring A is pyridine. In some embodiments of the compound, ring B is benzene. In some embodiments, ring A is pyridine and ring B is benzene.

(39) In some embodiments of the compound, R.sup.1 and R.sup.2 are each independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof. R.sup.1 and R.sup.2 can be joined or fused into a ring.

(40) In some embodiments, at least one R.sup.A or R.sup.B comprises an aromatic group further fused by the first group.

(41) In some embodiments, at least one pair of two adjacent R.sup.A form the first group fused to the ring A; or at least one pair of two adjacent R.sup.B form the first group fused to the ring B.

(42) In some embodiments, at least one R.sup.A or R.sup.B comprises an aromatic group further fused by the first group, and this R.sup.A or R.sup.B joins with an adjacent substituent and fuses to ring A or B.

(43) In some embodiments of the compound, the ligand L.sub.A is selected from the group consisting of:

(44) ##STR00006##

(45) In some embodiments of the compound, the first group is selected from the group consisting of:

(46) ##STR00007## ##STR00008## ##STR00009## ##STR00010##

(47) In some embodiments of the compound, the ligand L.sub.A is

(48) ##STR00011##

(49) In some embodiments of the compound, the ligand L.sub.A is selected from the group consisting of:

(50) ##STR00012## ##STR00013## ##STR00014##
and substituted variants thereof, wherein each R.sup.3, R.sup.4, and R.sup.5 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 any adjacent substituents are optionally joined or fused into a ring.

(51) In some embodiments of the compound, the ligand L.sub.A is selected from the group consisting of LA1 to LA2891 defined below:

(52) TABLE-US-00001 LA1 to LA252 having the following structure embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1 LA2 LA3 0 LA4 LA5 LA6 LA7 LA8 0 LA9 LA10 LA11 LA12 LA13 0 LA14 LA15 LA16 LA17 LA18 0 LA19 LA20 LA21 LA22 LA23 0 LA24 LA25 LA26 LA27 LA28 0 LA29 LA30 LA31 LA32 LA33 0 embedded image LA34 LA35 LA36 LA37 LA38 0 LA39 LA40 LA41 LA42 LA43 00 01 LA44 02 03 LA45 04 05 LA46 06 07 LA47 08 09 LA48 0 LA49 LA50 LA51 LA52 LA53 0 LA54 LA55 LA56 LA57 LA58 0 LA59 LA60 LA61 LA62 LA63 0 LA64 LA65 LA66 LA67 LA68 0 LA69 LA70 embedded image LA71 LA72 LA73 0 LA74 LA75 LA76 LA77 LA78 0 LA79 LA80 LA81 LA82 LA83 0 LA84 LA85 LA86 LA87 LA88 0 LA89 LA90 LA91 LA92 LA93 00 01 LA94 02 03 LA95 04 05 LA96 06 07 LA97 08 09 LA98 0 LA99 LA100 LA101 LA102 LA103 0 LA104 LA105 LA106 LA107 embedded image LA108 0 LA109 LA110 LA111 LA112 LA113 0 LA114 LA115 LA116 LA117 LA118 0 LA119 LA120 LA121 LA122 LA123 0 LA124 LA125 LA126 LA127 LA128 0 LA129 LA130 LA131 LA132 LA133 0 LA134 LA135 LA136 LA137 LA138 0 LA139 LA140 LA141 LA142 embedded image LA143 00 01 LA144 02 03 LA145 04 05 LA146 06 07 LA147 08 09 LA148 0 LA149 LA150 LA151 LA152 LA153 0 LA154 LA155 LA156 LA157 LA158 0 LA159 LA160 LA161 LA162 LA163 0 LA164 LA165 LA166 LA167 LA168 0 LA169 LA170 LA171 LA172 LA173 0 LA174 LA175 embedded image LA176 LA177 LA178 0 LA179 LA180 LA181 LA182 LA183 0 LA184 LA185 LA186 LA187 LA188 0 LA189 LA190 LA191 LA192 LA193 00 01 LA194 02 03 LA195 04 05 LA196 06 07 LA197 08 09 LA198 0 LA199 LA200 LA201 LA202 LA203 0 LA204 LA205 LA206 LA207 LA208 0 embedded image LA209 LA210 LA211 LA212 LA213 0 LA214 LA215 LA216 LA217 LA218 0 LA219 LA220 LA221 LA222 LA223 0 LA224 LA225 LA226 LA227 LA228 0 LA229 LA230 LA231 LA232 LA233 0 LA234 LA235 LA236 LA237 LA238 0 LA239 LA240 LA241 LA242 LA243 00 embedded image 01 LA244 02 03 LA245 04 05 LA246 06 07 LA247 08 09 LA248 0 LA249 LA250 LA251 LA252

(53) TABLE-US-00002 LA253 to LA504 having the following structure 0 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA253 LA254 LA255 LA256 LA257 0 LA258 LA259 LA260 LA261 LA262 0 LA263 LA264 LA265 LA266 LA267 0 LA268 LA269 LA270 LA271 LA272 0 LA273 LA274 LA275 LA276 LA277 0 LA278 LA279 embedded image LA280 LA281 LA282 0 LA283 LA284 LA285 LA286 LA287 0 LA288 LA289 LA290 LA291 LA292 00 LA293 01 02 LA294 03 04 LA295 05 06 LA296 07 08 LA297 09 0 LA298 LA299 LA300 LA301 LA302 0 LA303 LA304 LA305 LA306 LA307 0 LA308 LA309 LA310 LA311 LA312 embedded image 0 LA313 LA314 LA315 LA316 LA317 0 LA318 LA319 LA320 LA321 LA322 0 LA323 LA324 LA325 LA326 LA327 0 LA328 LA329 LA330 LA331 LA332 0 LA333 LA334 LA335 LA336 LA337 0 LA338 LA339 LA340 LA341 LA342 00 LA343 01 02 LA344 03 04 LA345 05 06 LA346 07 embedded image 08 LA347 09 0 LA348 LA349 LA350 LA351 LA352 0 LA353 LA354 LA355 LA356 LA357 0 LA358 LA359 LA360 LA361 LA362 0 LA363 LA364 LA365 LA366 LA367 0 LA368 LA369 LA370 LA371 LA372 0 LA373 LA374 LA375 LA376 LA377 0 LA378 LA379 LA380 LA381 embedded image LA382 0 LA383 LA384 LA385 LA386 LA387 0 LA388 LA389 LA390 LA391 LA392 00 LA393 01 02 LA394 03 04 LA395 05 06 LA396 07 08 LA397 09 0 LA398 LA399 LA400 LA401 LA402 0 LA403 LA404 LA405 LA406 LA407 0 LA408 LA409 LA410 LA411 LA412 0 LA413 LA414 embedded image LA415 LA416 LA417 0 LA418 LA419 LA420 LA421 LA422 0 LA423 LA424 LA425 LA426 LA427 0 LA428 LA429 LA430 LA431 LA432 0 LA433 LA434 LA435 LA436 LA437 0 LA438 LA439 LA440 LA441 LA442 00 LA443 01 02 LA444 03 04 LA445 05 06 LA446 07 08 LA447 09 embedded image 0 LA448 LA449 LA450 LA451 LA452 0 LA453 LA454 LA455 LA456 LA457 0 LA458 LA459 LA460 LA461 LA462 0 LA463 LA464 LA465 LA466 LA467 0 LA468 LA469 LA470 LA471 LA472 0 LA473 LA474 LA475 LA476 LA477 0 LA478 LA479 LA480 LA481 LA482 embedded image 0 LA483 LA484 LA485 LA486 LA487 0 LA488 LA489 LA490 LA491 LA492 000 LA493 001 002 LA494 003 004 LA495 005 006 LA496 007 008 LA497 009 010 LA498 011 012 LA499 013 014 LA500 015 016 LA501 017 018 LA502 019 020 LA503 021 022 LA504 023 024

(54) TABLE-US-00003 LA505 to LA756 having the following structure 025 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA505 026 027 LA506 028 029 LA507 030 031 LA508 032 033 LA509 034 035 LA510 036 037 LA511 038 039 LA512 040 041 LA513 042 043 LA514 044 045 LA515 046 047 LA516 048 049 LA517 050 051 LA518 052 053 LA519 054 055 LA520 056 embedded image 057 LA521 058 059 LA522 060 061 LA523 062 063 LA524 064 065 LA525 066 067 LA526 068 069 LA527 070 071 LA528 072 073 LA529 074 075 LA530 076 077 LA531 078 079 LA532 080 081 LA533 082 083 LA534 084 085 LA535 086 087 LA536 088 089 LA537 090 091 LA538 092 093 LA539 094 095 LA540 096 097 LA541 098 embedded image 099 LA542 00 01 LA543 02 03 LA544 04 05 LA545 06 07 LA546 08 09 LA547 0 LA548 LA549 LA550 LA551 LA552 0 LA553 LA554 LA555 LA556 LA557 0 LA558 LA559 LA560 LA561 LA562 0 LA563 LA564 LA565 LA566 LA567 0 LA568 LA569 LA570 LA571 LA572 0 LA573 embedded image LA574 LA575 LA576 LA577 0 LA578 LA579 LA580 LA581 LA582 0 LA583 LA584 LA585 LA586 LA587 0 LA588 LA589 LA590 LA591 LA592 00 01 LA593 02 03 LA594 04 05 LA595 06 07 LA596 08 09 LA597 0 LA598 LA599 LA600 LA601 LA602 0 LA603 LA604 LA605 LA606 embedded image LA607 0 LA608 LA609 LA610 LA611 LA612 0 LA613 LA614 LA615 LA616 LA617 0 LA618 LA619 LA620 LA621 LA622 0 LA623 LA624 LA625 LA626 LA627 0 LA628 LA629 LA630 LA631 LA632 0 LA633 LA634 LA635 LA636 LA637 0 LA638 LA639 LA640 LA641 embedded image LA642 00 01 LA643 02 03 LA644 04 05 LA645 06 07 LA646 08 09 LA647 0 LA648 LA649 LA650 LA651 LA652 0 LA653 LA654 LA655 LA656 LA657 0 LA658 LA659 LA660 LA661 LA662 0 LA663 LA664 LA665 LA666 LA667 0 LA668 LA669 LA670 LA671 LA672 0 LA673 LA674 embedded image LA675 LA676 LA677 0 LA678 LA679 LA680 LA681 LA682 0 LA683 LA684 LA685 LA686 LA687 0 LA688 LA689 LA690 LA691 LA692 00 01 LA693 02 03 LA694 04 05 LA695 06 07 LA696 08 09 LA697 0 LA698 LA699 LA700 LA701 LA702 0 LA703 LA704 LA705 LA706 LA707 0 embedded image LA708 LA709 LA710 LA711 LA712 0 LA713 LA714 LA715 LA716 LA717 0 LA718 LA719 LA720 LA721 LA722 0 LA723 LA724 LA725 LA726 LA727 0 LA728 LA729 LA730 LA731 LA732 0 LA733 LA734 LA735 LA736 LA737 0 LA738 LA739 LA740 LA741 LA742 00 embedded image 01 LA743 02 03 LA744 04 05 LA745 06 07 LA746 08 09 LA747 0 LA748 LA749 LA750 LA751 LA752 0 LA753 LA754 LA755 LA756

(55) TABLE-US-00004 LA756 to LA1008 having the following structure 0 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA757 LA758 LA759 LA760 LA761 0 LA762 LA763 LA764 LA765 LA766 0 LA767 LA768 LA769 LA770 LA771 0 LA772 LA773 LA774 LA775 LA776 0 LA777 LA778 LA779 LA780 LA781 0 LA782 LA783 embedded image LA784 LA785 LA786 0 LA787 LA788 LA789 LA790 LA791 00 LA792 01 02 LA793 03 04 LA794 05 06 LA795 07 08 LA796 09 0 LA797 LA798 LA799 LA800 LA801 0 LA802 LA803 LA804 LA805 LA806 0 LA807 LA808 LA809 LA810 LA811 0 LA812 LA813 LA814 LA815 LA816 embedded image 0 LA817 LA818 LA819 LA820 LA821 0 LA822 LA823 LA824 LA825 LA826 0 LA827 LA828 LA829 LA830 LA831 0 LA832 LA833 LA834 LA835 LA836 0 LA837 LA838 LA839 LA840 LA841 00 LA842 01 02 LA843 03 04 LA844 05 06 LA845 07 08 LA846 09 0 LA847 LA848 LA849 embedded image LA850 LA851 0 LA852 LA853 LA854 LA855 LA856 0 LA857 LA858 LA859 LA860 LA861 0 LA862 LA863 LA864 LA865 LA866 0 LA867 LA868 LA869 LA870 LA871 0 LA872 LA873 LA874 LA875 LA876 0 LA877 LA878 LA879 LA880 LA881 0 LA882 LA883 LA884 embedded image LA885 LA886 0 LA887 LA888 LA889 LA890 LA891 00 LA892 01 02 LA893 03 04 LA894 05 06 LA895 07 08 LA896 09 0 LA897 LA898 LA899 LA900 LA901 0 LA902 LA903 LA904 LA905 LA906 0 LA907 LA908 LA909 LA910 LA911 0 LA912 LA913 LA914 LA915 LA916 0 LA917 embedded image LA918 LA919 LA920 LA921 0 LA922 LA923 LA924 LA925 LA926 0 LA927 LA928 LA929 LA930 LA931 0 LA932 LA933 LA934 LA935 LA936 0 LA937 LA938 LA939 LA940 LA941 00 LA942 01 02 LA943 03 04 LA944 05 06 LA945 07 08 LA946 09 0 LA947 LA948 LA949 LA950 embedded image LA951 0 LA952 LA953 LA954 LA955 LA956 0 LA957 LA958 LA959 LA960 LA961 0 LA962 LA963 LA964 LA965 LA966 0 LA967 LA968 LA969 LA970 LA971 0 LA972 LA973 LA974 LA975 LA976 0 LA977 LA978 LA979 LA980 LA981 0 LA982 LA983 LA984 LA985 embedded image LA986 0 LA987 LA988 LA989 LA990 LA991 000 LA992 001 002 LA993 003 004 LA994 005 006 LA995 007 008 LA996 009 010 LA997 011 012 LA998 013 014 LA999 015 016 LA1000 017 018 LA1001 019 020 LA1002 021 022 LA1003 023 024 LA1004 025 026 LA1005 027 028 LA1006 029 030 LA1007 031 032 LA1008 033 embedded image 034

(56) TABLE-US-00005 LA1009 to LA1260 having the following structure 035 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1009 036 037 LA1010 038 039 LA1011 040 041 LA1012 042 043 LA1013 044 045 LA1014 046 047 LA1015 048 049 LA1016 050 051 LA1017 052 053 LA1018 054 055 LA1019 056 057 LA1020 058 059 LA1021 060 061 LA1022 062 063 LA1023 064 embedded image 065 LA1024 066 067 LA1025 068 069 LA1026 070 071 LA1027 072 073 LA1028 074 075 LA1029 076 077 LA1030 078 079 LA1031 080 081 LA1032 082 083 LA1033 084 085 LA1034 086 087 LA1035 088 089 LA1036 090 091 LA1037 092 093 LA1038 094 095 LA1039 096 097 LA1040 098 099 LA1041 00 01 LA1042 02 03 LA1043 04 embedded image 05 LA1044 06 07 LA1045 08 09 LA1046 0 LA1047 LA1048 LA1049 LA1050 LA1051 0 LA1052 LA1053 LA1054 LA1055 LA1056 0 LA1057 LA1058 LA1059 LA1060 LA1061 0 LA1062 LA1063 LA1064 LA1065 LA1066 0 LA1067 LA1068 LA1069 LA1070 LA1071 0 LA1072 LA1073 embedded image LA1074 LA1075 LA1076 0 LA1077 LA1078 LA1079 LA1080 LA1081 0 LA1082 LA1083 LA1084 LA1085 LA1086 0 LA1087 LA1088 LA1089 LA1090 LA1091 00 01 LA1092 02 03 LA1093 04 05 LA1094 06 07 LA1095 08 09 LA1096 0 LA1097 LA1098 LA1099 LA1100 LA1101 0 LA1102 embedded image LA1103 LA1104 LA1105 LA1106 0 LA1107 LA1108 LA1109 LA1110 LA1111 0 LA1112 LA1113 LA1114 LA1115 LA1116 0 LA1117 LA1118 LA1119 LA1120 LA1121 0 LA1122 LA1123 LA1124 LA1125 LA1126 0 LA1127 LA1128 LA1129 LA1130 LA1131 0 LA1132 LA1133 embedded image LA1134 LA1135 LA1136 0 LA1137 LA1138 LA1139 LA1140 LA1141 00 01 LA1142 02 03 LA1143 04 05 LA1144 06 07 LA1145 08 09 LA1146 0 LA1147 LA1148 LA1149 LA1150 LA1151 0 LA1152 LA1153 LA1154 LA1155 LA1156 0 LA1157 LA1158 LA1159 LA1160 LA1161 0 LA1162 embedded image LA1163 LA1164 LA1165 LA1166 0 LA1167 LA1168 LA1169 LA1170 LA1171 0 LA1172 LA1173 LA1174 LA1175 LA1176 0 LA1177 LA1178 LA1179 LA1180 LA1181 0 LA1182 LA1183 LA1184 LA1185 LA1186 0 LA1187 LA1188 LA1189 LA1190 LA1191 00 01 LA1192 02 03 LA1193 04 embedded image 05 LA1194 06 07 LA1195 08 09 LA1196 0 LA1197 LA1198 LA1199 LA1200 LA1201 0 LA1202 LA1203 LA1204 LA1205 LA1206 0 LA1207 LA1208 LA1209 LA1210 LA1211 0 LA1212 LA1213 LA1214 LA1215 LA1216 0 LA1217 LA1218 LA1219 LA1220 LA1221 0 LA1222 LA1223 embedded image LA1224 LA1225 LA1226 0 LA1227 LA1228 LA1229 LA1230 LA1231 0 LA1232 LA1233 LA1234 LA1235 LA1236 0 LA1237 LA1238 LA1239 LA1240 LA1241 00 01 LA1242 02 03 LA1243 04 05 LA1244 06 07 LA1245 08 09 LA1246 0 LA1247 LA1248 LA1249 LA1250 LA1251 0 LA1252 embedded image LA1253 LA1254 LA1255 LA1256 0 LA1257 LA1258 LA1259 LA1260

(57) TABLE-US-00006 LA1261 to LA1512 having the following structure 0 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1261 LA1262 LA1263 LA1264 LA1265 0 LA1266 LA1267 LA1268 LA1269 LA1270 0 LA1271 LA1272 LA1273 LA1274 LA1275 0 LA1276 LA1277 LA1278 LA1279 LA1280 0 LA1281 LA1282 LA1283 LA1284 LA1285 embedded image 0 LA1286 LA1287 LA1288 LA1289 LA1290 00 LA1291 01 02 LA1292 03 04 LA1293 05 06 LA1294 07 08 LA1295 09 0 LA1296 LA1297 LA1298 LA1299 LA1300 0 LA1301 LA1302 LA1303 LA1304 LA1305 0 LA1306 LA1307 LA1308 LA1309 LA1310 0 LA1311 LA1312 LA1313 LA1314 embedded image LA1315 0 LA1316 LA1317 LA1318 LA319 LA1320 0 LA1321 LA1322 LA1323 LA1324 LA1325 0 LA1326 LA1327 LA1328 LA1329 LA1330 0 LA1331 LA1332 LA1333 LA1334 LA1335 0 LA1336 LA1337 LA1338 LA1339 LA1340 00 LA1341 01 02 LA1342 03 04 LA1343 05 06 LA1344 07 embedded image 08 LA1345 09 0 LA1346 LA1347 LA1348 LA1349 LA1350 0 LA1351 LA1352 LA1353 LA1354 LA1355 0 LA1356 LA1357 LA1358 LA1359 LA1360 0 LA1361 LA1362 LA1363 LA1364 LA1365 0 LA1366 LA1367 LA1368 LA1369 LA1370 0 LA1371 LA1372 LA1373 LA1374 LA1375 embedded image 0 LA1376 LA1377 LA1378 LA1379 LA1380 0 LA1381 LA1382 LA1383 LA1384 LA1385 0 LA1386 LA1387 LA1388 LA1389 LA1390 00 LA1391 01 02 LA1392 03 04 LA1393 05 06 LA1394 07 08 LA1395 09 0 LA1396 LA1397 LA1398 LA1399 LA1400 0 LA1401 LA1402 LA1403 LA1404 embedded image LA1405 0 LA1406 LA1407 LA1408 LA1409 LA1410 0 LA1411 LA1412 LA1413 LA1414 LA1415 0 LA1416 LA1417 LA1418 LA1419 LA1420 0 LA1421 LA1422 LA1423 LA1424 LA1425 0 LA1426 LA1427 LA1428 LA1429 LA1430 0 LA1431 LA1432 LA1433 LA1434 LA1435 0 embedded image LA1436 LA1437 LA1438 LA1439 LA1440 00 LA1441 01 02 LA1442 03 04 LA1443 05 06 LA1444 07 08 LA1445 09 0 LA1446 LA1447 LA1448 LA1449 LA1450 0 LA1451 LA1452 LA1453 LA1454 LA1455 0 LA1456 LA1457 LA1458 LA1459 LA1460 0 LA1461 LA1462 LA1463 LA1464 LA1465 embedded image 0 LA1466 LA1467 LA1468 LA1469 LA1470 0 LA1471 LA1472 LA1473 LA1474 LA1475 0 LA1476 LA1477 LA1478 LA1479 LA1480 0 LA1481 LA1482 LA1483 LA1484 LA1485 0 LA1486 LA1487 LA1488 LA1489 LA1490 000 LA1491 001 002 LA1492 003 004 LA1493 005 006 LA1494 007 embedded image 008 LA1495 009 010 LA1496 011 012 LA1497 013 014 LA1498 015 016 LA1499 017 018 LA1500 019 020 LA1501 021 022 LA1502 023 024 LA1503 025 026 LA1504 027 028 LA1505 029 030 LA1506 031 032 LA1507 033 034 LA1508 035 036 LA1509 037 038 LA1510 039 040 LA1511 041 042 LA1512 043 044

(58) TABLE-US-00007 LA1513 to LA1764 having the following structure 045 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1513 046 047 LA1514 048 049 LA1515 050 051 LA1516 052 053 LA1517 054 055 LA1518 056 057 LA1519 058 059 LA1520 060 061 LA1521 062 063 LA1522 064 065 LA1523 066 067 LA1524 068 069 LA1525 070 071 LA1526 072 073 LA1527 074 075 embedded image LA1528 076 077 LA1529 078 079 LA1530 080 081 LA1531 082 083 LA1532 084 085 LA1533 086 087 LA1534 088 089 LA1535 090 091 LA1536 092 093 LA1537 094 095 LA1538 096 097 LA1539 098 099 LA1540 00 01 LA1541 02 03 LA1542 04 05 LA1543 06 07 LA1544 08 09 LA1545 0 LA1546 LA1547 LA1548 LA1549 embedded image LA1550 0 LA1551 LA1552 LA1553 LA1554 LA1555 0 LA1556 LA1557 LA1558 LA1559 LA1560 0 LA1561 LA1562 LA1563 LA1564 LA1565 0 LA1566 LA1567 LA1568 LA1569 LA1570 0 LA1571 LA1572 LA1573 LA1574 LA1575 0 LA1576 LA1577 LA1578 LA1579 LA1580 0 embedded image LA1581 LA1582 LA1583 LA1584 LA1585 0 LA1586 LA1587 LA1588 LA1589 LA1590 00 01 LA1591 02 03 LA1592 04 05 LA1593 06 07 LA1594 08 09 LA1595 0 LA1596 LA1597 LA1598 LA1599 LA1600 0 LA1601 LA1602 LA1603 LA1604 LA1605 0 LA1606 LA1607 LA1608 LA1609 embedded image LA1610 0 LA1611 LA1612 LA1613 LA1614 LA1615 0 LA1616 LA1617 LA1618 LA1619 LA1620 0 LA1621 LA1622 LA1623 LA1624 LA1625 0 LA1626 LA1627 LA1628 LA1629 LA1630 0 LA1631 LA1632 LA1633 LA1634 LA1635 0 LA1636 LA1637 LA1638 LA1639 LA1640 00 embedded image 01 LA1641 02 03 LA1642 04 05 LA1643 06 07 LA1644 08 09 LA1645 0 LA1646 LA1647 LA1648 LA1649 LA1650 0 LA1651 LA1652 LA1653 LA1654 LA1655 0 LA1656 LA1657 LA1658 LA1659 LA1660 0 LA1661 LA1662 LA1663 LA1664 LA1665 0 LA1666 LA1667 LA1668 LA1669 LA1670 0 embedded image LA1671 LA1672 LA1673 LA1674 LA1675 0 LA1676 LA1677 LA1678 LA1679 LA1680 0 LA1681 LA1682 LA1683 LA1684 LA1685 0 LA1686 LA1687 LA1688 LA1689 LA1690 00 01 LA1691 02 03 LA1692 04 05 LA1693 06 07 LA1694 08 09 LA1695 0 LA1696 LA1697 LA1698 LA1699 embedded image LA1700 0 LA1701 LA1702 LA1703 LA1704 LA1705 0 LA1706 LA1707 LA1708 LA1709 LA1710 0 LA1711 LA1712 LA1713 LA1714 LA1715 0 LA1716 LA1717 LA1718 LA1719 LA1720 0 LA1721 LA1722 LA1723 LA1724 LA1725 0 LA1726 LA1727 LA1728 LA1729 LA1730 0 embedded image LA1731 LA1732 LA1733 LA1734 LA1735 0 LA1736 LA1737 LA1738 LA1739 LA1740 00 01 LA1741 02 03 LA1742 04 05 LA1743 06 07 LA1744 08 09 LA1745 0 LA1746 LA1747 LA1748 LA1749 LA1750 0 LA1751 LA1752 LA1753 LA1754 LA1755 0 LA1756 LA1757 LA1758 LA1759 LA1760 0 embedded image LA1761 LA1762 LA1763 LA1764

(59) TABLE-US-00008 LA1765 to LA2016 having the following 0 embedded image structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA1765 LA1766 LA1767 LA1768 LA1769 0 LA1770 LA1771 LA1772 LA1773 LA1774 0 LA1775 LA1776 LA1777 LA1778 LA1779 0 LA1780 LA1781 LA1782 LA1783 LA1784 0 LA1785 LA1786 LA1787 LA1788 embedded image LA1789 00 LA1790 01 02 LA1791 03 04 LA1792 05 06 LA1793 07 08 LA1794 09 0 LA1795 LA1796 LA1797 LA1798 LA1799 0 LA1800 LA1801 LA1802 LA1803 LA1804 0 LA1805 LA1806 LA1807 LA1808 LA1809 0 LA1810 LA1811 LA1812 LA1813 LA1814 0 LA1815 LA1816 LA1817 embedded image LA1818 LA1819 0 LA1820 LA1821 LA1822 LA1823 LA1824 0 LA1825 LA1826 LA1827 LA1828 LA1829 0 LA1830 LA1831 LA1832 LA1833 LA1834 0 LA1835 LA1836 LA1837 LA1838 LA1839 00 LA1840 01 02 LA1841 03 04 LA1842 05 06 LA1843 07 08 LA1844 09 0 LA1845 LA1846 embedded image LA1847 LA1848 LA1849 0 LA1850 LA1851 LA1852 LA1853 LA1854 0 LA1855 LA1856 LA1857 LA1858 LA1859 0 LA1860 LA1861 LA1862 LA1863 LA1864 0 LA1865 LA1866 LA1867 LA1868 LA1869 0 LA1870 LA1871 LA1872 LA1873 LA1874 0 LA1875 LA1876 LA1877 embedded image LA1878 LA1879 0 LA1880 LA1881 LA1882 LA1883 LA1884 0 LA1885 LA1886 LA1887 LA1888 LA1889 00 LA1890 01 02 LA1891 03 04 LA1892 05 06 LA1893 07 08 LA1894 09 0 LA1895 LA1896 LA1897 LA1898 LA1899 0 LA1900 LA1901 LA1902 LA1903 LA1904 0 LA1905 LA1906 embedded image LA1907 LA1908 LA1909 0 LA1910 LA1911 LA1912 LA1913 LA1914 0 LA1915 LA1916 LA1917 LA1918 LA1919 0 LA1920 LA1921 LA1922 LA1923 LA1924 0 LA1925 LA1926 LA1927 LA1928 LA1929 0 LA1930 LA1931 LA1932 LA1933 LA1934 0 LA1935 LA1936 LA1937 LA1938 embedded image LA1939 00 LA1940 01 02 LA1941 03 04 LA1942 05 06 LA1943 07 08 LA1944 09 0 LA1945 LA1946 LA1947 LA1948 LA1949 0 LA1950 LA1951 LA1952 LA1953 LA1954 0 LA1955 LA1956 LA1957 LA1958 LA1959 0 LA1960 LA1961 LA1962 LA1963 LA1964 0 LA1965 LA1966 LA1967 embedded image LA1968 LA1969 0 LA1970 LA1971 LA1972 LA1973 LA1974 0 LA1975 LA1976 LA1977 LA1978 LA1979 0 LA1980 LA1981 LA1982 LA1983 LA1984 0 LA1985 LA1986 LA1987 LA1988 LA1989 000 LA1990 001 002 LA1991 003 004 LA1992 005 006 LA1993 007 008 LA1994 009 010 LA1995 011 embedded image 012 LA1996 013 014 LA1997 015 016 LA1998 017 018 LA1999 019 020 LA2000 021 022 LA2001 023 024 LA2002 025 026 LA2003 027 028 LA2004 029 030 LA2005 031 032 LA2006 033 034 LA2007 035 036 LA2008 037 038 LA2009 039 040 LA2010 041 042 LA2011 043 044 LA2012 045 046 LA2013 047 048 LA2014 049 050 embedded image LA2015 051 052 LA2016 053 054

(60) TABLE-US-00009 LA2017 to LA2268 having the following 055 embedded image structure wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA2017 056 057 LA2018 058 059 LA2019 060 061 LA2020 062 063 LA2021 064 065 LA2022 066 067 LA2023 068 069 LA2024 070 071 LA2025 072 073 LA2026 074 075 LA2027 076 077 LA2028 078 079 LA2029 080 081 LA2030 082 083 LA2031 084 embedded image 085 LA2032 086 087 LA2033 088 089 LA2034 090 091 LA2035 092 093 LA2036 094 095 LA2037 096 097 LA2038 098 099 LA2039 00 01 LA2040 02 03 LA2041 04 05 LA2042 06 07 LA2043 08 09 LA2044 0 LA2045 LA2046 LA2047 LA2048 LA2049 0 LA2050 LA2051 LA2052 LA2053 LA2054 0 LA2055 LA2056 embedded image LA2057 LA2058 LA2059 0 LA2060 LA2061 LA2062 LA2063 LA2064 0 LA2065 LA2066 LA2067 LA2068 LA2069 0 LA2070 LA2071 LA2072 LA2073 LA2074 0 LA2075 LA2076 LA2077 LA2078 LA2079 0 LA2080 LA2081 LA2082 LA2083 LA2084 0 LA2085 LA2086 LA2087 embedded image LA2088 LA2089 00 01 LA2090 02 03 LA2091 04 05 LA2092 06 07 LA2093 08 09 LA2094 0 LA2095 LA2096 LA2097 LA2098 LA2099 0 LA2100 LA2101 LA2102 LA2103 LA2104 0 LA2105 LA2106 LA2107 LA2108 LA109 0 LA2110 LA2111 LA2112 LA2113 LA2114 0 LA2115 LA2116 LA2117 embedded image LA2118 LA2119 0 LA2120 LA2121 LA2122 LA2123 LA2124 0 LA2125 LA2126 LA2127 LA2128 LA2129 0 LA2130 LA2131 LA2132 LA2133 LA2134 0 LA2135 LA2136 LA2137 LA2138 LA2139 00 01 LA2140 02 03 LA2141 04 05 LA2142 06 07 LA2143 08 09 LA2144 0 LA2145 LA2146 embedded image LA2147 LA2148 LA2149 0 LA2150 LA2151 LA2152 LA2153 LA2154 0 LA2155 LA2156 LA2157 LA2158 LA2159 0 LA2160 LA2161 LA2162 LA2163 LA2164 0 LA2165 LA2166 LA2167 LA2168 LA2169 0 LA2170 LA2171 LA2172 LA2173 LA2174 0 LA2175 LA2176 LA2177 embedded image LA2178 LA2179 0 LA2180 LA2181 LA2182 LA2183 LA2184 0 LA2185 LA2186 LA2187 LA2188 LA2189 00 01 LA2190 02 03 LA2191 04 05 LA2192 06 07 LA2193 08 09 LA2194 0 LA2195 LA2196 LA2197 LA2198 LA2199 0 LA2200 LA2201 LA2202 LA2203 LA2204 0 LA2205 LA2206 embedded image LA2207 LA2208 LA2209 0 LA2210 LA2211 LA2212 LA2213 LA2214 0 LA2215 LA2216 LA2217 LA2218 LA2219 0 LA2220 LA2221 LA2222 LA2223 LA2224 0 LA2225 LA2226 LA2227 LA2228 LA2229 0 LA2230 LA2231 LA2232 LA2233 LA2234 0 LA2235 LA2236 LA2237 LA2238 embedded image LA2239 00 01 LA2240 02 03 LA2241 04 05 LA2242 06 07 LA2243 08 09 LA2244 0 LA2245 LA2246 LA2247 LA2248 LA2249 0 LA2250 LA2251 LA2252 LA2253 LA2254 0 LA2255 LA2256 LA2257 LA2258 LA2259 0 LA2260 LA2261 LA2262 LA2263 LA2264 0 LA2265 LA2266 LA2267 embedded image LA2268

(61) TABLE-US-00010 LA2269 to LA2520 having the following structure 0 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA2269 LA2270 LA2271 LA2272 LA2273 0 LA2274 LA2275 LA2276 LA2277 LA2278 0 LA2279 LA2280 LA2281 LA2282 LA2283 0 LA2284 LA2285 LA2286 LA2287 LA2288 00 LA2289 01 02 LA2290 03 04 LA2291 05 embedded image 06 LA2292 07 08 LA2293 09 0 LA2294 LA2295 LA2296 LA2297 LA2298 0 LA2299 LA2300 LA2301 LA2302 LA2303 0 LA2304 LA2305 LA2306 LA2307 LA2308 0 LA2309 LA2310 LA2311 LA2312 LA2313 0 LA2314 LA2315 LA2316 LA2317 LA2318 0 LA2319 LA2320 LA2321 LA2322 embedded image LA2323 0 LA2324 LA2325 LA2326 LA2327 LA2328 0 LA2329 LA2330 LA2331 LA2332 LA2333 0 LA2334 LA2335 LA2336 LA2337 LA2338 00 LA2339 01 02 LA2340 03 04 LA2341 05 06 LA2342 07 08 LA2343 09 0 LA2344 LA2345 LA2346 LA2347 LA2348 0 LA2349 LA2350 LA2351 embedded image LA2352 LA2353 0 LA2354 LA2355 LA2356 LA2357 LA2358 0 LA2359 LA2360 LA2361 LA2362 LA2363 0 LA2364 LA2365 LA2366 LA2367 LA2368 0 LA2369 LA2370 LA2371 LA2372 LA2373 0 LA2374 LA2375 LA2376 LA2377 LA2378 0 LA2379 LA2380 LA2381 LA2382 embedded image LA2383 0 LA2384 LA2385 LA2386 LA2387 LA2388 00 LA2389 01 02 LA2390 03 04 LA2391 05 06 LA2392 07 08 LA2393 09 0 LA2394 LA2395 LA2396 LA2397 LA2398 0 LA2399 LA2400 LA2401 LA2402 LA2403 0 LA2404 LA2405 LA2406 LA2407 LA2408 0 LA2409 LA2410 LA2411 embedded image LA2412 LA2413 0 LA2414 LA2415 LA2416 LA2417 LA2418 0 LA2419 LA2420 LA2421 LA2422 LA2423 0 LA2424 LA2425 LA2426 LA2427 LA2428 0 LA2429 LA2430 LA2431 LA2432 LA2433 0 LA2434 LA2435 LA2436 LA2437 LA2438 00 LA2439 01 02 LA2440 03 04 LA2441 05 embedded image 06 LA2442 07 08 LA2443 09 0 LA2444 LA2445 LA2446 LA2447 LA2448 0 LA2449 LA2450 LA2451 LA2452 LA2453 0 LA2454 LA2455 LA2456 LA2457 LA2458 0 LA2459 LA2460 LA2461 LA2462 LA2463 0 LA2464 LA2465 LA2466 LA2467 LA2468 0 LA2469 LA2470 LA2471 LA2472 embedded image LA2473 0 LA2474 LA2475 LA2476 LA2477 LA2478 0 LA2479 LA2480 LA2481 LA2482 LA2483 0 LA2484 LA2485 LA2486 LA2487 LA2488 000 LA2489 001 002 LA2490 003 004 LA2491 005 006 LA2492 007 008 LA2493 009 010 LA2494 011 012 LA2495 013 014 LA2496 015 016 LA2497 017 018 embedded image LA2498 019 020 LA2499 021 022 LA2500 023 024 LA2501 025 026 LA2502 027 028 LA2503 029 030 LA2504 031 032 LA2505 033 034 LA2506 035 036 LA2507 037 038 LA2508 039 040 LA2509 041 042 LA2510 043 044 LA2511 045 046 LA2512 047 048 LA2513 049 050 LA2514 051 052 LA2515 053 054 LA2516 055 056 LA2517 057 embedded image 058 LA2518 059 060 LA2519 061 062 LA2520 063 064

(62) TABLE-US-00011 LA2521 to LA2772 having the following structure 065 embedded image wherein R.sup.1 and R.sup.2 are defined as: ID R.sup.1 R.sup.2 LA2521 066 067 LA2522 068 069 LA2523 070 071 LA2524 072 073 LA2525 074 075 LA2526 076 077 LA2527 078 079 LA2528 080 081 LA2529 082 083 LA2530 084 085 LA2531 086 087 LA2532 088 089 LA2533 090 091 LA2534 092 093 LA2535 094 embedded image 095 LA2536 096 097 LA2537 098 099 LA2538 00 01 LA2539 02 03 LA2540 04 05 LA2541 06 07 LA2542 08 09 LA2543 0 LA2544 LA2545 LA2546 LA2547 LA2548 0 LA2549 LA2550 LA2551 LA2552 LA2553 0 LA2554 LA2555 LA2556 LA2557 LA2558 0 LA2559 LA2560 LA2561 LA2562 LA2563 0 embedded image LA2564 LA2565 LA2566 LA2567 LA2568 0 LA2569 LA2570 LA2571 LA2572 LA2573 0 LA2574 LA2575 LA2576 LA2577 LA2578 0 LA2579 LA2580 LA2581 LA2582 LA2583 0 LA2584 LA2585 LA2586 LA2587 LA2588 00 01 LA2589 02 03 LA2590 04 05 LA2591 06 07 LA2592 08 09 embedded image LA2593 0 LA2594 LA2595 LA2596 LA2597 LA2598 0 LA2599 LA2600 LA2601 LA2602 LA2603 0 LA2604 LA2605 LA2606 LA2607 LA2608 0 LA2609 LA2610 LA2611 LA2612 LA2613 0 LA2614 LA2615 LA2616 LA2617 LA2618 0 LA2619 LA2620 LA2621 LA2622 LA2623 0 embedded image LA2624 LA2625 LA2626 LA2627 LA2628 0 LA2629 LA2630 LA2631 LA2632 LA2633 0 LA2634 LA2635 LA2636 LA2637 LA2638 00 01 LA2639 02 03 LA2640 04 05 LA2641 06 07 LA2642 08 09 LA2643 0 LA2644 LA2645 LA2646 LA2647 LA2648 0 LA2649 LA2650 LA2651 LA2652 LA2653 0 embedded image LA2654 LA2655 LA2656 LA2657 LA2658 0 LA2659 LA2660 LA2661 LA2662 LA2663 0 LA2664 LA2665 LA2666 LA2667 LA2668 0 LA2669 LA2670 LA2671 LA2672 LA2673 0 LA2674 LA2675 LA2676 LA2677 LA2678 0 LA2679 LA2680 LA2681 LA2682 LA2683 0 LA2684 embedded image LA2685 LA2686 LA2687 LA2688 00 01 LA2689 02 03 LA2690 04 05 LA2691 06 07 LA2692 08 09 LA2693 0 LA2694 LA2695 LA2696 LA2697 LA2698 0 LA2699 LA2700 LA2701 LA2702 LA2703 0 LA2704 LA2705 LA2706 LA2707 LA2708 0 LA2709 LA2710 LA2711 LA2712 LA2713 0 embedded image LA2714 LA2715 LA2716 LA2717 LA2718 0 LA2719 LA2720 LA2721 LA2722 LA2723 0 LA2724 LA2725 LA2726 LA2727 LA2728 0 LA2729 LA2730 LA2731 LA2732 LA2733 0 LA2734 LA2735 LA2736 LA2737 LA2738 00 01 LA2739 02 03 LA2740 04 05 LA2741 06 07 LA2742 08 09 LA2743 0 embedded image LA2744 LA2745 LA2746 LA2747 LA2748 0 LA2749 LA2750 LA2751 LA2752 LA2753 0 LA2754 LA2755 LA2756 LA2757 LA2758 0 LA2759 LA2760 LA2761 LA2762 LA2763 0 LA2764 LA2765 LA2766 LA2767 LA2768 0 LA2769 LA2770 LA2771 LA2772

(63) ##STR05570## ##STR05571## ##STR05572## ##STR05573## ##STR05574## ##STR05575## ##STR05576## ##STR05577## ##STR05578## ##STR05579## ##STR05580## ##STR05581## ##STR05582## ##STR05583## ##STR05584## ##STR05585## ##STR05586## ##STR05587## ##STR05588## ##STR05589## ##STR05590## ##STR05591## ##STR05592## ##STR05593## ##STR05594##

(64) In some embodiments of the compound, the compound has a formula of M(L.sub.A).sub.n(L.sub.B).sub.m-n;

(65) wherein M is Ir or Pt; L.sub.B is a bidentate ligand; and

(66) 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.

(67) In some embodiments of the compound having the formula of M(L.sub.A).sub.n(L.sub.B).sub.m-n as defined above, the compound has a formula of Ir(L.sub.A).sub.3. In some embodiments, the compound has a formula of Ir(L.sub.A)(L.sub.B).sub.2 or Ir(L.sub.A).sub.2(L.sub.B); and wherein L.sub.B is different from L.sub.A.

(68) In some embodiments of the compound having the formula of M(L.sub.A).sub.n(L.sub.B).sub.m-n as defined above, the compound has a formula of Pt(L.sub.A)(L.sub.B); and L.sub.A and L.sub.B can be same or different. In some embodiments, L.sub.A and L.sub.B are connected to form a tetradentate ligand. In some embodiments, L.sub.A and L.sub.B are connected at two places to form a macrocyclic tetradentate ligand.

(69) In some embodiments of the compound having the formula of M(L.sub.A).sub.n(L.sub.B).sub.m-n as defined above, L.sub.B is selected from the group consisting of:

(70) ##STR05595## ##STR05596##

(71) wherein each X.sup.1 to X.sup.13 are independently selected from the group consisting of carbon and nitrogen;

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

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

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

(75) wherein R′, R″, R.sub.a, R.sub.b, R.sub.c, and R.sub.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

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

(77) In some embodiments of the compound having the formula of M(L.sub.A).sub.n(L.sub.B).sub.m-n as defined above, L.sub.B is selected from the group consisting of:

(78) ##STR05597## ##STR05598## ##STR05599##

(79) In some embodiments of the compound wherein the ligand L.sub.A is selected from the group consisting of LA1 to LA2891, the compound is the Compound Ax having the formula Ir(L.sub.Ai).sub.2(L.sub.Cj);

(80) wherein x=17i+j-17; i is an integer from 1 to 2891, and j is an integer from 1 to 17; and

(81) wherein L.sub.c is selected from the group consisting of:

(82) ##STR05600## ##STR05601## ##STR05602## ##STR05603##

(83) In some embodiments of the compound wherein the ligand L.sub.A is selected from the group consisting of LA1 to LA2891, the compound is the Compound By having the formula Ir(L.sub.Ai)(L.sub.Bk).sub.2;

(84) wherein y=300i+k-300; i is an integer from 1 to 2891 and k is an integer from 1 to 300; and

(85) wherein L.sub.B is selected from the group consisting of:

(86) ##STR05604## ##STR05605## ##STR05606## ##STR05607## ##STR05608## ##STR05609## ##STR05610## ##STR05611## ##STR05612## ##STR05613## ##STR05614## ##STR05615## ##STR05616## ##STR05617## ##STR05618## ##STR05619## ##STR05620## ##STR05621## ##STR05622## ##STR05623## ##STR05624## ##STR05625## ##STR05626## ##STR05627## ##STR05628## ##STR05629## ##STR05630## ##STR05631## ##STR05632## ##STR05633## ##STR05634## ##STR05635## ##STR05636## ##STR05637## ##STR05638## ##STR05639## ##STR05640## ##STR05641## ##STR05642## ##STR05643## ##STR05644## ##STR05645## ##STR05646## ##STR05647## ##STR05648## ##STR05649## ##STR05650## ##STR05651## ##STR05652## ##STR05653## ##STR05654## ##STR05655## ##STR05656## ##STR05657## ##STR05658## ##STR05659## ##STR05660## ##STR05661## ##STR05662## ##STR05663## ##STR05664## ##STR05665## ##STR05666## ##STR05667## ##STR05668## ##STR05669## ##STR05670##

(87) According to another aspect, an organic light emitting device (OLED) is disclosed. The OLED comprises: an anode; a cathode; and an organic layer, disposed between the anode and the cathode. The organic layer comprises a compound comprising a first ligand L.sub.A having a structure according to Formula I

(88) ##STR05671##
In Formula I, rings A and B are each a 6-membered carbocyclic or heterocyclic ring; R.sup.A and R.sup.B each independently represent mono to the possible maximum number of substitution, or no substitution; Z.sup.1 and Z.sup.2 are each independently selected from the group consisting of carbon or nitrogen; each R.sup.A and R.sup.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 of R.sup.A or R.sup.B comprises an aromatic group further fused by a first group; or (2) at least one pair of two adjacent R.sup.A or one pair of two adjacent R.sup.B form the first group fused to ring A or B; wherein the first group is

(89) ##STR05672##

(90) wherein in (1), * represents the points fused to the aromatic group; and in (2), * represents the points fused to ring A or B and the rings to which the first group is fused is not pyridine when R.sup.1 and R.sup.2 are not joined or fused into a ring;

(91) wherein R.sup.1 and R.sup.2 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;

(92) wherein R.sup.1 and R.sup.2 are optionally joined or fused into a ring;

(93) wherein the ligand L.sub.A is coordinated to a metal M;

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

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

(96) According to another aspect, a consumer product comprising the OLED is also disclosed.

(97) In some embodiments, the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.

(98) In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED comprises a RGB pixel arrangement or white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a hand held device, or a wearable device. In some embodiments, the OLED is a display panel having less than 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a display panel having at least 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a lighting panel.

(99) According to another aspect, an emissive region in an OLED is disclosed. The emissive region comprises a compound a compound comprising a first ligand L.sub.A having a structure according to Formula I

(100) ##STR05673##
defined herein.

(101) In some embodiments of the emissive region, the compound is an emissive dopant or a non-emissive dopant.

(102) In some embodiments, the emissive region further comprises a host, wherein the host comprises at least one selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

(103) In some embodiments, the emissive region further comprises a host, wherein the host is selected from the group consisting of:

(104) ##STR05674## ##STR05675## ##STR05676## ##STR05677## ##STR05678##
and combinations thereof.

(105) In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.

(106) According to another aspect, a formulation comprising the compound described herein is also disclosed.

(107) The OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.

(108) The organic layer can also include a host. In some embodiments, two or more hosts are preferred. In some embodiments, the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport. In some embodiments, the host can include a metal complex. The host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the host can be an unfused substituent independently selected from the group consisting of C.sub.nH.sub.2n+1, OC.sub.nH.sub.2n+1, OAr.sub.1, N(C.sub.nH.sub.2n+1).sub.2, N(Ar.sub.1)(Ar.sub.2), CH═CH—C.sub.nH.sub.2n+1, C≡C—C.sub.nH.sub.2n+1, Ar.sub.1, Ar.sub.1—Ar.sub.2, and C.sub.nH.sub.2n—Ar.sub.1, or the host has no substitutions. In the preceding substituents n can range from 1 to 10; and Ar.sub.1 and Ar.sub.2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. The host can be an inorganic compound. For example a Zn containing inorganic material e.g. ZnS.

(109) The host can be a compound comprising 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. The host can include a metal complex. The host can be, but is not limited to, a specific compound selected from the group consisting of:

(110) ##STR05679## ##STR05680## ##STR05681## ##STR05682## ##STR05683##
and combinations thereof.
Additional information on possible hosts is provided below.

(111) In yet another aspect of the present disclosure, a formulation that comprises the novel compound disclosed herein is described. The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, and an electron transport layer material, disclosed herein.

(112) Combination with Other Materials

(113) The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

(114) Conductivity Dopants:

(115) A charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved. Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.

(116) Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804 and US2012146012.

(117) ##STR05684## ##STR05685## ##STR05686##
HIL/HTL:

(118) A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoO.sub.x; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.

(119) Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:

(120) ##STR05687##

(121) Each of Ar.sup.1 to Ar.sup.9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each Ar may be unsubstituted or may be substituted by a substituent selected from the group consisting of 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.

(122) In one aspect, Ar.sup.1 to Ar.sup.9 is independently selected from the group consisting of

(123) ##STR05688##
wherein k is an integer from 1 to 20; X.sup.101 to X.sup.108 is C (including CH) or N; Z.sup.101 is NAr.sup.1, O, or S; Ar.sup.1 has the same group defined above.

(124) Examples of metal complexes used in HIL or HTL include, but are not limited to the following general formula:

(125) ##STR05689##
wherein Met is a metal, which can have an atomic weight greater than 40; (Y.sup.101-Y.sup.102) is a bidentate ligand, Y.sup.101 and Y.sup.102 are independently selected from C, N, O, P, and S; L.sup.101 is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

(126) In one aspect, (Y.sup.101-Y.sup.102) is a 2-phenylpyridine derivative. In another aspect, (Y.sup.101-Y.sup.102) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc.sup.+/Fc couple less than about 0.6 V.

(127) Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, U.S. Ser. No. 06/517,957, US20020158242, US20030162053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US20080106190, US20080124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US2011007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, U.S. Pat. Nos. 5,061,569, 5,639,914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018.

(128) ##STR05690## ##STR05691## ##STR05692## ##STR05693## ##STR05694## ##STR05695## ##STR05696## ##STR05697## ##STR05698## ##STR05699## ##STR05700## ##STR05701## ##STR05702## ##STR05703## ##STR05704## ##STR05705## ##STR05706## ##STR05707## ##STR05708## ##STR05709## ##STR05710## ##STR05711##
EBL:

(129) An electron blocking layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies, and or longer lifetime, as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and or higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.

(130) Host:

(131) The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.

(132) Examples of metal complexes used as host are preferred to have the following general formula:

(133) ##STR05712##
wherein Met is a metal; (Y.sup.103-Y.sup.104) is a bidentate ligand, Y.sup.103 and Y.sup.104 are independently selected from C, N, O, P, and S; L.sup.101 is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

(134) In one aspect, the metal complexes are:

(135) ##STR05713##
wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.

(136) In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y.sup.103-Y.sup.104) is a carbene ligand.

(137) Examples of other organic compounds used as host are selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each option within each group may be unsubstituted or may be substituted by a substituent selected from the group consisting of 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.

(138) In one aspect, the host compound contains at least one of the following groups in the molecule:

(139) ##STR05714## ##STR05715##
wherein each of R.sup.101 to R.sup.107 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 when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20; k′″ is an integer from 0 to 20. X.sup.101 to X.sup.108 is selected from C (including CH) or N. Z.sup.101 and Z.sup.102 is selected from NR.sup.101, O, or S.

(140) Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S. Pat. No. 7,154,114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472,

(141) ##STR05716## ##STR05717## ##STR05718## ##STR05719## ##STR05720## ##STR05721## ##STR05722## ##STR05723## ##STR05724## ##STR05725## ##STR05726##
Additional Emitters:

(142) One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials. Examples of suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.

(143) Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Ser. No. 06/699,599, U.S. Ser. No. 06/916,554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US20070231600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US20080233410, US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663, US20100244004, US20100295032, US2010102716, US2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US2011285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US2014103305, U.S. Pat. Nos. 6,303,238, 6,413,656, 6,653,654, 6,670,645, 6,687,266, 6,835,469, 6,921,915, 7,279,704, 7,332,232, 7,378,162, 7,534,505, 7,675,228, 7,728,137, 7,740,957, 7,759,489, 7,951,947, 8,067,099, 8,592,586, 8,871,361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.

(144) ##STR05727## ##STR05728## ##STR05729## ##STR05730## ##STR05731## ##STR05732## ##STR05733## ##STR05734## ##STR05735## ##STR05736## ##STR05737## ##STR05738## ##STR05739## ##STR05740## ##STR05741## ##STR05742## ##STR05743## ##STR05744## ##STR05745## ##STR05746## ##STR05747## ##STR05748## ##STR05749## ##STR05750##
HBL:

(145) A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and or higher triplet energy than one or more of the hosts closest to the HBL interface.

(146) In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.

(147) In another aspect, compound used in HBL contains at least one of the following groups in the molecule:

(148) ##STR05751##
wherein k is an integer from 1 to 20; L.sup.101 is an another ligand, k′ is an integer from 1 to 3.
ETL:

(149) Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.

(150) In one aspect, compound used in ETL contains at least one of the following groups in the molecule: I

(151) ##STR05752##
wherein R.sup.101 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, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar.sup.1 to Ar.sup.3 has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X.sup.101 to X.sup.108 is selected from C (including CH) or N.

(152) In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:

(153) ##STR05753##
wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L.sup.101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.

(154) Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, U.S. Pat. Nos. 6,656,612, 8,415,031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

(155) ##STR05754## ##STR05755## ##STR05756## ##STR05757## ##STR05758## ##STR05759## ##STR05760## ##STR05761## ##STR05762##
Charge Generation Layer (CGL)

(156) In tandem or stacked OLEDs, the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually. Typical CGL materials include n and p conductivity dopants used in the transport layers.

(157) In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.

EXPERIMENTAL

(158) An example of the inventive compounds (Ir(L.sub.A2795).sub.2L.sub.C5) can be synthesized by the following scheme.

(159) ##STR05763##

(160) 1-chloroimidazo[1,2-a:4,5-c′]dipyridine can be synthesized by following the literature procedure (Russian Journal of Organic Chemistry, 2006, 42, 883-886), which can react with (3,5-dimethylphenyl)boronic acid to give the ligand L.sub.A2795. Ir dimer can be made by refluxing L.sub.A2795 with IrCl.sub.3 and (Z)-3,7-diethyl-6-hydroxynon-5-en-4-one in the presence of base to give Ir(L.sub.A2795).sub.2L.sub.C5.

(161) The structure of Ir(L.sub.A2795).sub.2L.sub.C5 was modeled by DFT calculation using B3LYP method and the energy of the lowest triplet excited state (T1) was calculated to be 644 nm. The compound will emit light of red color, which is useful for display and lighting applications. Because of the fused rings, the invented compounds are expected to have strong interactions with host materials in the OLED devices, which might enhance the electronic conductivity of the emission layer. In addition, the inventive compounds exhibit large dipole moment lying in the same direction of the molecular long axis. This feature has been proposed to help the horizontal alignment of the transition dipole moment of the emitter in order to achieve better light extraction, which will improve the efficiency the OLED devices. In summary, the invented compounds are useful materials as emitters in OLED devices to improve the performance.

(162) It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.

Organic electroluminescent materials and devices

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Abstract

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Description