IP Library › Granted Patent US 12,349,589

Granted Patent B2

US 12,349,589 · App. 17/528,552 · Granted Jul 1, 2025

Organic electroluminescent materials and devices

Inventors: Morgan C. Macinnis (Yardley, PA); Hsiao-Fan Chen (Lawrence Township, NJ); Tyler Fleetham (Newtown, PA); Peter Wolohan (Princeton Junction, NJ); Jerald Feldman (Cherry Hill, NJ); Jui-Yi Tsai (Newtown, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Zhiqiang Ji (Chalfont, PA); Sean Michael Ryno (Yardley, PA); Rasha Hamze (Philadelphia, PA); Chun Lin (Yardley, PA); Elena Sheina (Langhorne, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/346 C07F15/0033 C07F15/0086 C09K11/02 C09K11/06 H10K85/342 C07B2200/05 C09K2211/1007 C09K2211/1014 C09K2211/1022 C09K2211/1029 C09K2211/104 C09K2211/1044 C09K2211/1096 C09K2211/185 H10K50/11 H10K2101/10

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

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

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 12,349,589
App. No.: 17/528,552
Granted: Jul 1, 2025
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

A compound comprising a ligand L A comprising a moiety L having a structure of Formula I is provided. In Formula I, L A coordinated to a metal M; A 1 is selected from B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″; where rings A, B, and C are 5- or 6-membered rings; Y 1 , Y 2 , and Y 3 are selected from direct bonds, the metal M, and a variety of linkers; a+b+c=2 or 3; and one of a number of specific conditions is met. OLED devices, consumer products, and formulations including the compound are also provided.

Claims (495)

1. A compound comprising a ligand L A ,

wherein L A comprises a moiety L having a structure of Formula I:

wherein:

L A coordinated to a metal M;

A 1 is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″;

each rings A, B, and C is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

Y 1 , Y 2 , and Y 3 are each independently a moiety selected from the group consisting of direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO 2 , CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, metal M and combinations thereof;

wherein X is selected from the group consisting of O, S, Se, NR′, and CR″R′″;

a, b, and c are each independently 0 for not present or 1 for present;

a+b+c=2 or 3;

R A , R B , and R C each independently represent mono to the maximum allowable substitution, or no substitution;

each R, R′, R″, R′″, R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

M can be coordinated to other ligands;

the ligand L A can be joined with other ligands to form a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two substituents of R, R′, R″, R′″, R A , R B , and R C can be joined or fused to form a ring;

if the compound comprises a ring that includes metal M and A1, then one or more of the following is true: (i) A 1 is not B, (ii) at least one of Y 1 , Y 2 , or Y 3 is present and is not metal M, O, or S, (iii) one of Y 1 , Y 2 , or Y 3 comprises metal M and one of the remaining two of Y 1 , Y 2 , or Y 3 is not present, or (iv) at least one of ring A, ring B, or Ring C is pyrazole or imidazole coordinated to metal M by a N atom; and

at least one of the following conditions is true:

1) At least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring;

2) At least one of Y 1 , Y 2 , or Y 3 is present as C═R;

3) A 1 is B and at least one of Y 1 , Y 2 , and Y 3 is present as a direct bond;

4) A 1 is B, a=b=1, and Y 1 is different from Y 2 ;

5) A 1 is N and at least one of Y 1 , Y 2 , and Y 3 is present as BR;

6) A 1 is B, a=b=1, and Y 1 is not O;

7) The compound comprises a metal-carbene bond; or

8) At least one pair of adjacent R A , R B , or R C join together to form a fused moiety comprising one or more rings fused to and extending from Ring A, Ring B, or Ring C, respectively, wherein the fused moiety coordinates directly to the metal M, and at most only one of rings A, B, or C is coordinated to the metal M.

2. The compound of claim 1 , wherein each R, R′, R″, R′″, R A , R B , and R C is independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein at most only one of rings A, B, and C is coordinated to the metal M.

4. The compound of claim 3 , wherein none of rings A, B, and C are coordinated to the metal M.

5. The compound of claim 1 , wherein M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.

6. The compound of claim 1 , wherein the moiety L has a structure selected from the group consisting of:

wherein

each of X 1 , X 2 , X 3 , X 4 , X 3 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , and X 19 is independently C or N;

R D and R E each independently represent mono to the maximum allowable substitution, or no substitution;

each R D and R E is independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

each of Y 4 , Y 5 , and Y 6 is independently selected from the group consisting of C═R, NR, O, S, Se, BR, CRR′, SiRR′, GeRR′, and SnRR′; and

any two substituents of R, R′, R″, R′″, R A , R B , R C , R D and R E can be joined or fused to form a ring.

7. The compound of claim 1 , wherein the compound has a structure of

wherein:

Z 1 , Z 2 , Z 3 , and Z 4 are independently selected from C or N;

M 1 is Pd or Pt;

each one of rings A 1 , A 2 , A 3 , and A 4 is independently monocyclic or multicyclic ring structures comprising at least one 5-membered or 6-membered carbocyclic or heterocyclic ring;

K 1 to K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least one of K 3 and K 4 is a direct bond;

L 1 to L 4 are each independently selected from the group consisting of a single bond, absent a bond, O, S, C═R′, CR′R″, SiR′R″, BR′, BR′R″, and NR′, wherein at least two of L 1 to L 4 are present;

R 1 ′, R 2 ′, R 3 ′ and R 4 ′ each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R 1 ′, R 2 ′, R 3 ′ R 4 ′, R′, and R″ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

any two of R 1 ′, R 2 ′, R 3 ′ R 4 ′, R′, and R″ can be joined or fused together to form a ring; and

at least one of R 1 ′, R 2 ′, R 3 ′, R 4 ′, L 1 , L 2 , L 3 , L 4 , ring A 1 , ring A 2 , ring A 3 , ring A 4 , or a combination thereof comprises a structure of Formula I.

8. The compound of claim 7 , wherein each one of rings A 1 , A 2 , A 3 , and A 4 is independently a monocyclic or a multicyclic aromatic ring structure.

9. The compound of claim 7 , wherein each one of rings A 1 , A 2 , A 3 , and A 4 is independently selected from the group consisting of phenyl, pyridine, pyrazine, pyrimidine, pyridazine, imidazole, imidazole derived carbene, pyrazole, furane, thiophene, pyrrole, and benzo-fused variants thereof.

10. The compound of claim 7 , wherein at least one of L 1 , L 2 , L 3 , and L 4 is O, NR′, or CR′R″.

11. The compound of claim 7 , wherein two of Z 1 , Z 2 , Z 3 , and Z 4 are C, and the remaining two of Z 1 , Z 2 , Z 3 , and Z 4 are N.

12. The compound of claim 7 , wherein two of Z 1 , Z 2 , Z 3 , and Z 4 are C, one of Z 1 , Z 2 , Z 3 , and Z 4 is carbene C, and the remaining one of Z 1 , Z 2 , Z 3 , and Z 4 is N.

13. The compound of claim 7 , wherein K 1 , K 2 , K 3 , and K 4 are all direct bonds.

14. The compound of claim 7 , wherein one of K 1 , K 2 , K 3 , and K 4 is O.

15. The compound of claim 7 , wherein Formula II has a structure selected from the group consisting of:

wherein:

each R A′ , R B′ , R C′ , R D′ , R E′ , R F′ , and R G′ is independently hydrogen or a substituent selected from the group consisting of the metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any two substituents of R A′ , R B′ , R C′ , R D′ , R E′ , R F′ , and R G′ are optionally joined or fused into a ring; and

at least one of R A′ , R B′ , R C′ , R D′ , R E′ , R F′ , R G′ , or a combination thereof, with or without, the remaining portions of Formula II comprises a structure of Formula I.

16. The compound of claim 7 , wherein the compound has the formula Pt(L A′ )(L B′ ), where the ligand L A′ has the structure

wherein L 4 is connected to ring A 1 of ligand L B′ , and the ligand L B′ has the structure

where the ligand L A′ has the formula L A′ a -(i)(j)(k)(l)(m) wherein a is an integer from 65 to 172; and each of L A′ 65-(1)(1)(1)(1)(1) to L A′ 197-(307)(307)(307)(307)(307) has the structure defined below:

Ligand #

Structure of L A ′

R A1 -R A6

L A ′65-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′65-(1)(1)(1)(1)(1) to L A ′65- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′66-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′66-(1)(1)(1)(1)(1) to L A ′66- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′67-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′67-(1)(1)(1)(1)(1) to L A ′67- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′68-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′68-(1)(1)(1)(1)(1) to L A ′68- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′69-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′69-(1)(1)(1)(1)(1) to L A ′69- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′70-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′70-(1)(1)(1)(1)(1) to L A ′70- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′71-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′71-(1)(1)(1)(1)(1) to L A ′71- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′72-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′72-(1)(1)(1)(1)(1) to L A ′72- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′73-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′73-(1)(1)(1)(1)(1) to L A ′73- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′74-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′74-(1)(1)(1)(1)(1) to L A ′74- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′75-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′75-(1)(1)(1)(1)(1) to L A ′75- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′76-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′76-(1)(1)(1)(1)(1) to L A ′76- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′77-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′77-(1)(1)(1)(1)(1) to L A ′77- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′78-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′78-(1)(1)(1)(1)(1) to L A ′78- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′79-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′79-(1)(1)(1)(1)(1) to L A ′79- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′80-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′80-(1)(1)(1)(1)(1) to L A ′80- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′81-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′81-(1)(1)(1)(1)(1) to L A ′81- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′82-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′82-(1)(1)(1)(1)(1) to L A ′82- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′83-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′83-(1)(1)(1)(1)(1) to L A ′83- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′84-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′84-(1)(1)(1)(1)(1) to L A ′84- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′85-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′85-(1)(1)(1)(1)(1) to L A ′85- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′86-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′86-(1)(1)(1)(1)(1) to L A ′86- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′87-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′87-(1)(1)(1)(1)(1) to L A ′87- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′88-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′88-(1)(1)(1)(1)(1) to L A ′88- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′89-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′89-(1)(1)(1)(1)(1) to L A ′89- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′90-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′90-(1)(1)(1)(1)(1) to L A ′90- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′91-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′91-(1)(1)(1)(1)(1) to L A ′91- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′92-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′92-(1)(1)(1)(1)(1) to L A ′92- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′93-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′93-(1)(1)(1)(1)(1) to L A ′93- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′94-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′94-(1)(1)(1)(1)(1) to L A ′94- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′95-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′95-(1)(1)(1)(1)(1) to L A ′95- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′96-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′96-(1)(1)(1)(1)(1) to L A ′96- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′97-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′97-(1)(1)(1) to L A ′97- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′98-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′98-(1)(1)(1)(1) to L A ′98- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′99-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′99-(1)(1)(1)(1) to L A ′99- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′100-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′100-(1)(1)(1)(1)(1) to L A ′100- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′101-(i), wherein i is an integer from 1 to 307, wherein L A ′101-(1) to L A ′101- (307) have the structure

wherein R A1 = Ri,

L A ′102-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L A ′102-(1)(1) to L A ′102- (307)(307) have the structure

wherein R A1 = Ri, and R A2 = Rj,

L A ′103-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L A ′103-(1)(1) to L A ′103- (307)(307) have the structure

wherein R A1 = Ri, and R A2 = Rj,

L A ′104-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L A ′104-(1)(1) to L A ′104- (307)(307) have the structure

wherein R A1 = Ri, and R A2 = Rj,

L A ′105-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′105-(1)(1)(1) to L A ′105- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′106-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′106-(1)(1)(1) to L A ′1056- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′107-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′107-(1)(1)(1) to L A ′107- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′108-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′108-(1)(1)(1)(1) to L A ′108- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′109-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′109-(1)(1)(1)(1) to L A ′109- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′110-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′110-(1)(1)(1)(1)(1) to L A ′110- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′111-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′111-(1)(1)(1)(1)(1) to L A ′111- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′112-(i)(j)(k)(l)(m)(n), wherein i, j, k, l, m, and n are each independently an integer from 1 to 307, wherein L A ′112- (1)(1)(1)(1)(1)(1) to L A ′112- (307)(307)(307)(307)(307)(307 have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, R A5 = Rm, and R A6 = Rn,

L A ′113-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L A ′113-(1)(1) to L A ′113- (307)(307) have the structure

wherein R A1 = Ri, and R A2 = Rj,

L A ′114-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′114-(1)(1)(1) to L A ′114- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′115-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′115-(1)(1)(1) to L A ′115- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′116-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L A ′116-(1)(1)(1) to L A ′116- (307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, and R A3 = Rk,

L A ′117-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′117-(1)(1)(1)(1) to L A ′117- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′118-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′118-(1)(1)(1)(1) to L A ′118- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′119-(i)(j)(k)(l), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′119-(1)(1)(1)(1) to L A ′119- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′120-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′120-(1)(1)(1)(1)(1) to L A ′120- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′121-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′121-(1)(1)(1)(1)(1) to L A ′121- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′122-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′122-(1)(1)(1)(1)(1) to L A ′122- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′123-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′123-(1)(1)(1)(1)(1) to L A ′123- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′124-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′124-(1)(1)(1)(1)(1) to L A ′124- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′125-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′125-(1)(1)(1)(1)(1) to L A ′125- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′126-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′126-(1)(1)(1)(1)(1) to L A ′126- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′127-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′127-(1)(1)(1)(1)(1) to L A ′127- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′128-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′128-(1)(1)(1)(1)(1) to L A ′128- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′129-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′129-(1)(1)(1)(1)(1) to L A ′129- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′130-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′130-(1)(1)(1)(1)(1) to L A ′130- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′131-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′131-(1)(1)(1)(1)(1) to L A ′131- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′132-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′132-(1)(1)(1)(1)(1) to L A ′132- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′133-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′133-(1)(1)(1)(1)(1) to L A ′133- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′134-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′134-(1)(1)(1)(1)(1) to L A ′134- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′135-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′135-(1)(1)(1)(1)(1) to L A ′135- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′136-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′136-(1)(1)(1)(1)(1) to L A ′136- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′137-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′137-(1)(1)(1)(1)(1) to L A ′137- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′138-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′138-(1)(1)(1)(1)(1) to L A ′138- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′139-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′139-(1)(1)(1)(1)(1) to L A ′139- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′140-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′140-(1)(1)(1)(1)(1) to L A ′140- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′141-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′141-(1)(1)(1)(1)(1) to L A ′141- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′142-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′142-(1)(1)(1)(1)(1) to L A ′142- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′143-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′143-(1)(1)(1)(1)(1) to L A ′143- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′144-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′144-(1)(1)(1)(1)(1) to L A ′144- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′145-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′145-(1)(1)(1)(1)(1) to L A ′145- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′146-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′146-(1)(1)(1)(1)(1) to L A ′146- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′147-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′147-(1)(1)(1)(1)(1) to L A ′147- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′148-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′148-(1)(1)(1)(1)(1) to L A ′148- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′149-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′149-(1)(1)(1)(1)(1) to L A ′149- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′150-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′150-(1)(1)(1)(1)(1) to L A ′150- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′151-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′151-(1)(1)(1)(1)(1) to L A ′151- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′152-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′152-(1)(1)(1)(1)(1) to L A ′152- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′153-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′153-(1)(1)(1)(1)(1) to L A ′153- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′154-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′154-(1)(1)(1)(1)(1) to L A ′154- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′155-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′155-(1)(1)(1)(1)(1) to L A ′155- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′156-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′156-(1)(1)(1)(1)(1) to L A ′156- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′157-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′157-(1)(1)(1)(1)(1) to L A ′157- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′158-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′158-(1)(1)(1)(1)(1) to L A ′158- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′159-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′159-(1)(1)(1)(1)(1) to L A ′159- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′160-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′160-(1)(1)(1)(1)(1) to L A ′160- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′161-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′161-(1)(1)(1)(1)(1) to L A ′161- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′162-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′162-(1)(1)(1)(1)(1) to L A ′162- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′163-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′163-(1)(1)(1)(1)(1) to L A ′163- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′164-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′164-(1)(1)(1)(1)(1) to L A ′164- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′165-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′165-(1)(1)(1)(1)(1) to L A ′165- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′166-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′166-(1)(1)(1)(1)(1) to L A ′166- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′167-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′167-(1)(1)(1)(1)(1) to L A ′167- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′168-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′168-(1)(1)(1)(1)(1) to L A ′168- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′169-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′169-(1)(1)(1)(1)(1) to L A ′169- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′170-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′170-(1)(1)(1)(1)(1) to L A ′170- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′171-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′171-(1)(1)(1)(1)(1) to L A ′171- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′172-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′172-(1)(1)(1)(1)(1) to L A ′172- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′173-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′173-(1)(1)(1)(1)(1) to L A ′173- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′174-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′174-(1)(1)(1)(1)(1) to L A ′174- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′175-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′175-(1)(1)(1)(1)(1) to L A ′175- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′176-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′176-(1)(1)(1)(1)(1) to L A ′176- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′177-(i)(j)(k)(l)(m), wherein i, j, k, and l are each independently an integer from 1 to 307, wherein L A ′177-(1)(1)(1)(1) to L A ′177- (307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′178-(i)(j)(k)(l), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′178-(1)(1)(1)(1)(1) to L A ′178- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, and R A4 = Rl,

L A ′179-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′179-(1)(1)(1)(1)(1) to L A ′179- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′180-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′180-(1)(1)(1)(1)(1) to L A ′180- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′181-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′181-(1)(1)(1)(1)(1) to L A ′181- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′182-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′182-(1)(1)(1)(1)(1) to L A ′182- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′183-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′183-(1)(1)(1)(1)(1) to L A ′183- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′184-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′184-(1)(1)(1)(1)(1) to L A ′184- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′185-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′185-(1)(1)(1)(1)(1) to L A ′185- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′186-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′186-(1)(1)(1)(1)(1) to L A ′186- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′187-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′187-(1)(1)(1)(1)(1) to L A ′187- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′188-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′188-(1)(1)(1)(1)(1) to L A ′188- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′189-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′189-(1)(1)(1)(1)(1) to L A ′189- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′190-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′190-(1)(1)(1)(1)(1) to L A ′190- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′191-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′191-(1)(1)(1)(1)(1) to L A ′191- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′192-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′192-(1)(1)(1)(1)(1) to L A ′192- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′193-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′193-(1)(1)(1)(1)(1) to L A ′193- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′194-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′194-(1)(1)(1)(1)(1) to L A ′194- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′195-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′195-(1)(1)(1)(1)(1) to L A ′195- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′196-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′196-(1)(1)(1)(1)(1) to L A ′196- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

L A ′197-(i)(j)(k)(l)(m), wherein i, j, k, l, and m are each independently an integer from 1 to 307, wherein L A ′197-(1)(1)(1)(1)(1) to L A ′197- (307)(307)(307)(307)(307) have the structure

wherein R A1 = Ri, R A2 = Rj, R A3 = Rk, R A4 = Rl, and R A5 = Rm,

wherein L B′ has the formula L B′ b -(i)(j)(k)(o)(l) wherein b is an integer from 1 to 43; and each of L B′ 1-(1)(1)(1)(1)(1) to L B′ 43-(307)(307)(307)(307)(307) has the structure defined below:

R B1 , R B2 , R B3 , R B4 , R B6 ,

Ligand #

Structure of L B′

R B7 , R B8 , R B9 , and R B11

L B′ 1-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 1- (1)(1)(1)(1) to L B′ 1- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,

L B′ 2-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 2-(1)(1)(1) to L B′ 2- (307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 3-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 3- (1)(1)(1)(1) to L B′ 3- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B7 = Rj, R B8 = Rk, and R B11 = Ro,

L B′ 4-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 4-(1)(1)(1) to L B′ 4- (307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 5-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 5-(1)(1)(1) to L B′ 5- (307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 6-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 6-(1)(1) to L B′ 6- (307)(307) have the structure

wherein R B6 = Ri and R B7 = Rj,

L B′ 7-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 7-(1)(1)(1) to L B′ 7- (307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 8-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 8-(1)(1) to L B′ 8- (307)(307) have the structure

wherein R B1 = Ri and R B6 = Rj,

L B′ 9-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 9- (1)(1)(1)(1) to L B′ 9- (307)(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,

L B′ 10-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 10-(1)(1)(1) to L B′ 10-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 11-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 11-(1)(1)(1) to L B′ 11-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 12-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 12- (1)(1)(1)(1) to L B′ 12- (307)(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,

L B′ 13-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 13-(1)(1)(1) to L B ,13-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 14-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 14-(1)(1)(1) to L B′ 14-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 15-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 15-(1)(1)(1) to L B′ 15-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 16-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 16- (1)(1)(1)(1) to L B′ 16- (307)(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,

L B′ 17-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 17-(1)(1)(1) to L B′ 17-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 18-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 18-(1)(1) to L B′ 18- (307)(307) have the structure

wherein R B1 = Ri and R B6 = Rj,

L B′ 19-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 19-(1)(1)(1) to L B′ 19-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 20-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 20-(1)(1)(1) to L B′ 20-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 21-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 21-(1)(1)(1) to L B′ 21-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 22-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 22-(1)(1)(1) to L B′ 22-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 23-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 23-(1)(1)(1) to L B′ 23-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 24-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 24-(1)(1)(1) to L B′ 24-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 25-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 25-(1)(1)(1) to L B′ 25-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 26-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 26-(1)(1)(1) to L B′ 26-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 27-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 27- (1)(1)(1)(1) to L B′ 27- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,

L B′ 28-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 28- (1)(1)(1)(1) to L B′ 28- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,

L B′ 29-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 29-(1)(1)(1) to L B′ 29-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 30-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 30- (1)(1)(1)(1) to L B′ 30- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, R B7 = Rk, and R B8 = Ro,

L B′ 31-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 31-(1)(1)(1) to L B′ 31-(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, and R B8 = Rk,

L B′ 32-(i)(j)(k), wherein i, j, and k are each independently an integer from 1 to 307, wherein L B′ 32-(1)(1)(1) to L B′ 32-(307)(307)(307) have the structure

wherein R B1 = Ri, R B6 = Rj, and R B7 = Rk,

L B′ 33-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 33-(1)(1) to L B′ 33- (307)(307) have the structure

wherein R B1 = Ri and R B6 = Rj,

L B′ 34-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 34-(1)(1) to L B′ 34- (307)(307) have the structure

wherein R B1 = Ri and R B6 = Rj,

L B′ 35-(i)(j)(k)(o), wherein i, j, k, and o are each independently an integer from 1 to 307, wherein L B′ 35- (1)(1)(1)(1) to L B′ 35- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B2 = Rj, R B6 = Rk, and R B7 = Ro,

L B′ 36-(i)(j), wherein i and j are each an integer independently from 1 to 307, wherein L B′ 36-(1)(1) to L B′ 36- (307)(307) have the structure

wherein R B1 = Ri and R B2 = Rj,

L B′ 37-(i)(j)(k) wherein each of i, j, and k is independently an integer from 1 to 307, wherein L B′ 37-(1)(1)(1) to L B′ 37- (307)(307)(307) have the structure

wherein R B1 = Ri, R B3 = Rj, and R B3 = Rk,

L B′ 38-(i)(j) wherein each of i and j is independently an integer from 1 to 307, wherein L B′ 38-(1)(1) to L B′ 38- (307)(307) have the structure

wherein R B1 = Ri and R B3 = Rj,

L B′ 39-(i)(j) wherein each of i and j is independently an integer from 1 to 307, wherein L B′ 39-(1)(1) to L B′ 39- (307)(307) have the structure

wherein R B1 = Ri and R B2 = Rj,

L B′ 40-(i)(j) wherein each of i and j is independently an integer from 1 to 307, wherein L B′ 40-(1)(1) to L B′ 40- (307)(307) have the structure

wherein R B1 = Ri and R B2 = Rj,

L B′ 41-(i)(j) wherein each of i and j is independently an integer from 1 to 307, wherein L B′ 41-(1)(1) to L B′ 41- (307)(307) have the structure

wherein R B1 = Ri and R B2 = Rj,

L B′ 42-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 307, L B′ 42-(1)(1)(1)(1) to L B′ 42-(307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, and R B4 = Rl,

L B′ 43-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 307, wherein L B′ 43- (1)(1)(1)(1) to L B′ 43- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B2 = Rj, R B3 = Rk, and R B4 = Rl.

L B′ 44-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 307, wherein L B′ 44- (1)(1)(1)(1) to L B′ 44- (307)(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,

L B′ 45-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 307, wherein L B′ 45- (1)(1)(1)(1) to L B′ 45- (307)(307)(307)(307) have the structure

wherein R B6 = Ri, R B7 = Rj, R B8 = Rk, and R B9 = Ro,

L B′ 46-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 46-(1)(1) to L B′ 46- (307)(307), have the structure

wherein R B6 = Ri and R B7 = Rj,

L B′ 47-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 47-(1)(1) to L B′ 47- (307)(307), have the structure

wherein R B6 = Ri and R B7 = Rj,

L B′ 48-(i)(j), wherein i and j are each independently an integer from 1 to 307, wherein L B′ 48-(1)(1) to L B′ 48- (307)(307), have the structure

wherein R B6 = Ri and R B7 = Rj,

L B′ 49-(i)(j)(k)(l) wherein each of i, j, k, and l is independently an integer from 1 to 307, wherein L B′ 49- (1)(1)(1)(1) to L B′ 49- (307)(307)(307)(307) have the structure

wherein R B1 = Ri, R B3 = Rj, R B3 = Rk, and R B4 = Rl,

with the proviso that when L A′ is selected from the group consisting of L A′ 187 to L A′ 198, L B′ is selected from the group consisting of L B′ 46 to L B′ 49;

where R1 to R307 are defined below:

wherein Me is methyl, iPr is isopropyl, tBu is t-butyl, and Ph is phenyl.

17. The compound of claim 7 , wherein the compound has a structure selected from below:

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

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand L A ,

wherein L A comprises a moiety L having a structure of Formula I:

wherein:

L A coordinated to a metal M;

A 1 is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″;

each rings A, B, and C is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

wherein X is selected from the group consisting of O, S, Se, NR′, and CR″R′″;

a, b, and c are each independently 0 for not present or 1 for present;

a+b+c=2 or 3;

R A , R B , and R C each independently represent mono to the maximum allowable substitution, or no substitution;

M can be coordinated to other ligands;

the ligand L A can be joined with other ligands to form a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two substituents of R, R′, R″, R′″, R A , R B , and R C can be joined or fused to form a ring;

if the compound comprises a ring that includes metal M and A 1 , then one or more of the following is true: (i) A 1 is not B, (ii) at least one of Y 1 , Y 2 , or Y 3 is present and is not metal M, O, or S, (iii) one of Y 1 , Y 2 , or Y 3 comprises metal M and one of the remaining two of Y 1 , Y 2 , or Y 3 is not present, or (iv) at least one of ring A, ring B, or Ring C is pyrazole or imidazole coordinated to metal M by a N atom; and

at least one of the following conditions is true:

1) At least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring;

2) At least one of Y 1 , Y 2 , or Y 3 is present as C═R;

3) A 1 is B and at least one of Y 1 , Y 2 , and Y 3 is present as a direct bond;

4) A 1 is B, a=b=1, and Y 1 is different from Y 2 ;

5) A 1 is N and at least one of Y 1 , Y 2 , and Y 3 is present as BR;

6) A 1 is B, a=b=1, and Y 1 is not O;

7) The compound comprises a metal-carbene bond; or

8) at least one pair of adjacent R A , R B , or R C join together to form a fused moiety comprising one or more rings fused to and extending from Ring A, Ring B, or Ring C, respectively, wherein the fused moiety coordinates directly to the metal M, and at most only one of rings A, B, or C is coordinated to the metal M.

19. The OLED of claim 18 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

20. 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, wherein the organic layer comprises a compound comprising a ligand L A ,

wherein L A comprises a moiety L having a structure of Formula I:

wherein:

L A coordinated to a metal M;

A 1 is selected from the group consisting of B, N, P, P═O, P═S, Al, Ga, SiR″, GeR″, and SnR″;

each rings A, B, and C is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

wherein X is selected from the group consisting of O, S, Se, NR′, and CR″R′″;

a, b, and c are each independently 0 for not present or 1 for present;

a+b+c=2 or 3;

R A , R B , and R C each independently represent mono to the maximum allowable substitution, or no substitution;

M can be coordinated to other ligands;

the ligand L A can be joined with other ligands to form a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two substituents of R, R′, R″, R′″, R A , R B , and R C can be joined or fused to form a ring;

if the compound comprises a ring that includes metal M and A 1 , then one or more of the following is true: (i) A 1 is not B, (ii) at least one of Y 1 , Y 2 , or Y 3 is present and is not metal M, O, or S, (iii) one of Y 1 , Y 2 , or Y 3 comprises metal M and one of the remaining two of Y 1 , Y 2 , or Y 3 is not present, or (iv) at least one of ring A, ring B, or Ring C is pyrazole or imidazole coordinated to metal M by a N atom; and

at least one of the following conditions is true:

1) At least one of rings A, B, and C is a 5-membered carbocyclic or heterocyclic ring;

2) At least one of Y 1 , Y 2 , or Y 3 is present as C═R;

3) A 1 is B and at least one of Y 1 , Y 2 , and Y 3 is present as a direct bond;

4) A 1 is B, a=b=1, and Y 1 is different from Y 2 ;

5) A 1 is N and at least one of Y 1 , Y 2 , and Y 3 is present as BR;

6) A 1 is B, a=b=1, and Y 1 is not O;

7) The compound comprises a metal-carbene bond; or

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2022

From: MACINNIS, MORGAN C.; CHEN, HSIAO-FAN; FLEETHAM, TYLER; WOLOHAN, PETER; FELDMAN, JERALD; TSAI, JUI-YI; BOUDREAULT, PIERRE-LUC T.; DYATKIN, ALEXEY BORISOVICH; JI, ZHIQIANG; RYNO, SEAN MICHAEL; HAMZE, RASHA; LIN, CHUN

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 058556/0517 →

Continuity (5)

Continuation 17148838 · Jan 14, 2021

Continuation In Part 17001052 · Aug 24, 2020

Provisional Application 63106035 · Oct 27, 2020

Provisional Application 62966650 · Jan 28, 2020

Related Publication 20220109120A1 · Apr 7, 2022

References Cited (201)

US 4769292A · Tang et al. · 1988 [cited by applicant]

US 5061569A · VanSlyke et al. · 1991 [cited by applicant]

US 5247190A · Friend et al. · 1993 [cited by applicant]

US 5703436A · Forrest et al. · 1997 [cited by applicant]

US 5707745A · Forrest et al. · 1998 [cited by applicant]

US 5834893A · Bulovic et al. · 1998 [cited by applicant]

US 5844363A · Gu et al. · 1998 [cited by applicant]

US 6013982A · Thompson et al. · 2000 [cited by applicant]

US 6087196A · Sturm et al. · 2000 [cited by applicant]

US 6091195A · Forrest et al. · 2000 [cited by applicant]

US 6097147A · Baldo et al. · 2000 [cited by applicant]

US 6294398B1 · Kim et al. · 2001 [cited by applicant]

US 6303238B1 · Thompson et al. · 2001 [cited by applicant]

US 6337102B1 · Forrest et al. · 2002 [cited by applicant]

US 6468819B1 · Kim et al. · 2002 [cited by applicant]

US 6528187B1 · Okada · 2003 [cited by applicant]

US 6687266B1 · Ma et al. · 2004 [cited by applicant]

US 6835469B2 · Kwong et al. · 2004 [cited by applicant]

US 6921915B2 · Takiguchi et al. · 2005 [cited by applicant]

US 7087321B2 · Kwong et al. · 2006 [cited by applicant]

US 7090928B2 · Thompson et al. · 2006 [cited by applicant]

US 7154114B2 · Brooks et al. · 2006 [cited by applicant]

US 7250226B2 · Tokito et al. · 2007 [cited by applicant]

US 7279704B2 · Walters et al. · 2007 [cited by applicant]

US 7332232B2 · Ma et al. · 2008 [cited by applicant]

US 7338722B2 · Thompson et al. · 2008 [cited by applicant]

US 7393599B2 · Thompson et al. · 2008 [cited by applicant]

US 7396598B2 · Takeuchi et al. · 2008 [cited by applicant]

US 7431968B1 · Shtein et al. · 2008 [cited by applicant]

US 7445855B2 · Mackenzie et al. · 2008 [cited by applicant]

US 7534505B2 · Lin et al. · 2009 [cited by applicant]

US 9312505B2 · Brooks et al. · 2016 [cited by applicant]

US 10103340B2 · Stoessel et al. · 2018 [cited by applicant]

US 20020034656A1 · Thompson et al. · 2002 [cited by applicant]

US 20020134984A1 · Igarashi · 2002 [cited by applicant]

US 20020158242A1 · Son et al. · 2002 [cited by applicant]

US 20030138657A1 · Li et al. · 2003 [cited by applicant]

US 20030152802A1 · Tsuboyama et al. · 2003 [cited by applicant]

US 20030162053A1 · Marks et al. · 2003 [cited by applicant]

US 20030175553A1 · Thompson et al. · 2003 [cited by applicant]

US 20030230980A1 · Forrest et al. · 2003 [cited by applicant]

US 20040036077A1 · Ise · 2004 [cited by applicant]

US 20040137267A1 · Igarashi et al. · 2004 [cited by applicant]

US 20040137268A1 · Igarashi et al. · 2004 [cited by applicant]

US 20040174116A1 · Lu et al. · 2004 [cited by applicant]

US 20050025993A1 · Thompson et al. · 2005 [cited by applicant]

US 20050112407A1 · Ogasawara et al. · 2005 [cited by applicant]

US 20050238919A1 · Ogasawara · 2005 [cited by applicant]

US 20050244673A1 · Satoh et al. · 2005 [cited by applicant]

US 20050260441A1 · Thompson et al. · 2005 [cited by applicant]

US 20050260449A1 · Walters et al. · 2005 [cited by applicant]

US 20060008670A1 · Lin et al. · 2006 [cited by applicant]

US 20060202194A1 · Jeong et al. · 2006 [cited by applicant]

US 20060240279A1 · Adamovich et al. · 2006 [cited by applicant]

US 20060251923A1 · Lin et al. · 2006 [cited by applicant]

US 20060263635A1 · Ise · 2006 [cited by applicant]

US 20060280965A1 · Kwong et al. · 2006 [cited by applicant]

US 20070190359A1 · Knowles et al. · 2007 [cited by applicant]

US 20070278938A1 · Yabunouchi et al. · 2007 [cited by applicant]

US 20080015355A1 · Schafer et al. · 2008 [cited by applicant]

US 20080018221A1 · Egen et al. · 2008 [cited by applicant]

US 20080106190A1 · Yabunouchi et al. · 2008 [cited by applicant]

US 20080124572A1 · Mizuki et al. · 2008 [cited by applicant]

US 20080220265A1 · Xia et al. · 2008 [cited by applicant]

US 20080297033A1 · Knowles et al. · 2008 [cited by applicant]

US 20090008605A1 · Kawamura et al. · 2009 [cited by applicant]

US 20090009065A1 · Nishimura et al. · 2009 [cited by applicant]

US 20090017330A1 · Iwakuma et al. · 2009 [cited by applicant]

US 20090030202A1 · Iwakuma et al. · 2009 [cited by applicant]

US 20090039776A1 · Yamada et al. · 2009 [cited by applicant]

US 20090045730A1 · Nishimura et al. · 2009 [cited by applicant]

US 20090045731A1 · Nishimura et al. · 2009 [cited by applicant]

US 20090101870A1 · Prakash et al. · 2009 [cited by applicant]

US 20090108737A1 · Kwong et al. · 2009 [cited by applicant]

US 20090115316A1 · Zheng et al. · 2009 [cited by applicant]

US 20090165846A1 · Johannes et al. · 2009 [cited by applicant]

US 20090167162A1 · Lin et al. · 2009 [cited by applicant]

US 20090179554A1 · Kuma et al. · 2009 [cited by applicant]

US 20140014922A1 · Lin et al. · 2014 [cited by applicant]

US 20140091265A1 · Stoessel · 2014 [cited by examiner]

US 20140371825A1 · Anémian · 2014 [cited by applicant]

US 20150287933A1 · Kottas · 2015 [cited by applicant]

US 20150349279A1 · Li · 2015 [cited by applicant]

US 20160233444A1 · Hayer · 2016 [cited by applicant]

US 20160359125A1 · Li · 2016 [cited by applicant]

US 20180053904A1 · Li · 2018 [cited by applicant]

US 20180287070A1 · Ji · 2018 [cited by applicant]

US 20180301629A1 · Hatakeyama et al. · 2018 [cited by applicant]

US 20190103568A1 · Hwang · 2019 [cited by applicant]

US 20190157579A1 · Jeon · 2019 [cited by applicant]

US 20190225636A1 · Bae · 2019 [cited by applicant]

US 20190312210A1 · Akashi · 2019 [cited by applicant]

US 20200203634A1 · Kim · 2020 [cited by examiner]

US 20200216481A1 · Chen et al. · 2020 [cited by applicant]

US 20210074932A1 · Park et al. · 2021 [cited by applicant]

US 20210130382A1 · Park · 2021 [cited by applicant]

US 20230002429A1 · Min · 2023 [cited by applicant]

CN 108467553 · 2017 [cited by applicant]

CN 108409762 · 2018 [cited by applicant]

CN 108484683 · 2018 [cited by applicant]

CN 113234106 · 2021 [cited by applicant]

EP 0650955 · 1995 [cited by applicant]

EP 1725079 · 2006 [cited by applicant]

EP 2034538 · 2009 [cited by applicant]

JP 200511610 · 2005 [cited by applicant]

JP 2007123392 · 2007 [cited by applicant]

JP 2007254297 · 2007 [cited by applicant]

JP 2008074939 · 2008 [cited by applicant]

KR 20180120619 · 2018 [cited by applicant]

WO 0139234 · 2001 [cited by applicant]

WO 0202714 · 2002 [cited by applicant]

WO 02015654 · 2002 [cited by applicant]

WO 03040257 · 2003 [cited by applicant]

WO 03060956 · 2003 [cited by applicant]

WO 2004093207 · 2004 [cited by applicant]

WO 04107822 · 2004 [cited by applicant]

WO 2005014551 · 2005 [cited by applicant]

WO 2005019373 · 2005 [cited by applicant]

WO 2005030900 · 2005 [cited by applicant]

WO 2005089025 · 2005 [cited by applicant]

WO 2005123873 · 2005 [cited by applicant]

WO 2006009024 · 2006 [cited by applicant]

WO 2006056418 · 2006 [cited by applicant]

WO 2006072002 · 2006 [cited by applicant]

WO 2006082742 · 2006 [cited by applicant]

WO 2006098120 · 2006 [cited by applicant]

WO 2006100298 · 2006 [cited by applicant]

WO 2006103874 · 2006 [cited by applicant]

WO 2006114966 · 2006 [cited by applicant]

WO 2006132173 · 2006 [cited by applicant]

WO 2007002683 · 2007 [cited by applicant]

WO 2007004380 · 2007 [cited by applicant]

WO 2007063754 · 2007 [cited by applicant]

WO 2007063796 · 2007 [cited by applicant]

WO 2008056746 · 2008 [cited by applicant]

WO 2008101842 · 2008 [cited by applicant]

WO 2008132085 · 2008 [cited by applicant]

WO 2009000673 · 2008 [cited by applicant]

WO 2009003898 · 2009 [cited by applicant]

WO 2009008311 · 2009 [cited by applicant]

WO 2009018009 · 2009 [cited by applicant]

WO 2009021126 · 2009 [cited by applicant]

WO 2009050290 · 2009 [cited by applicant]

WO 2009062578 · 2009 [cited by applicant]

WO 2009063833 · 2009 [cited by applicant]

WO 2009066778 · 2009 [cited by applicant]

WO 2009066779 · 2009 [cited by applicant]

WO 2009086028 · 2009 [cited by applicant]

WO 2009100991 · 2009 [cited by applicant]

WO 2019114764 · 2019 [cited by applicant]

PubChem “CID 147613853; Molecular Formula: C36H18BNOU—PubChem,” Feb. 7, 2018 (Feb. 7, 2018), pp. 1-8, XP055803252, Retrieved from the Internet: URL:https://pubchem.ncbi.nlm.nih.gov/compound/147613853#section=Substances … [cited by applicant]

Li, Q., et al., “B- and N-embedded color-tunable phosphorescent iridium complexes and B—N Lewis adducts with intriguing structural and optical changes,” Chem. Sci., Mar. 2019, vol. 10, No. 11, pp. 3257-3263. [cited by applicant]

Li, Q., et al., “An oxygen-bridged triarylamine polycyclic unit based tris-cyclometalated heteroleptic iridium(iii) complex: correlation between the structure and photophysical properties,” Dalton Trans., Apr. 2019, vol… [cited by applicant]

Wu, C. et al., “Tuning the Photophysical and Excited State Properties of Phosphorescent Iridium(III) Complexes by Polycyclic Unit Substitution,” ChemistryOpen, Mar. 2019, vol. 8, No. 3. pp. 339-343. [cited by applicant]

Li, Q., et al., “Comparison of Structural and Optical Properties for N-Embedded Polycyclic and Non-Embedded Cationic Phosphorescent Iridium(III) Complexes,” Eur. J. Inorg. Chem., Mar. 2019, vol. 2019, No. 10, pp. 1343-1… [cited by applicant]

Adachi, Chihaya et al., “Organic Electroluminescent Device Having a Hole Conductor as an Emitting Layer,” Appl. Phys. Lett., 55(15): 1489-1491 (1989). [cited by applicant]

Adachi, Chihaya et al., “Nearly 100% Internal Phosphorescence Efficiency in an Organic Light Emitting Device,” J. Appl. Phys., 90(10): 5048-5051 (2001). [cited by applicant]

Adachi, Chihaya et al., “High-Efficiency Red Electrophosphorescence Devices,” Appl. Phys. Lett., 78(11)1622-1624 (2001). [cited by applicant]

Aonuma, Masaki et al., “Material Design of Hole Transport Materials Capable of Thick-Film Formation in Organic Light Emitting Diodes,” Appl. Phys. Lett., 90, Apr. 30, 2007, 183503-1-183503-3. [cited by applicant]

Baldo et al., Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices, Nature, vol. 395. 151-154, (1998). [cited by applicant]

Baldo et al., Very high-efficiency green organic light-emitting devices based on electrophosphorescence, Appl. Phys. Lett., vol. 75, No. 1, 4-6 (1999). [cited by applicant]

Gao, Zhiqiang et al., “Bright-Blue Electroluminescence From a Silyl-Substituted ter-(phenylene-vinylene) derivative,” Appl. Phys. Lett., 74(6): 865-867 (1999). [cited by applicant]

Guo, Tzung-Fang et al., “Highly Efficient Electrophosphorescent Polymer Light-Emitting Devices,” Organic Electronics, 1: 15-20 (2000). [cited by applicant]

Hamada, Yují et al., “High Luminance in Organic Electroluminescent Devices with Bis(10-hydroxybenzo[h]quinolinato)beryllium as an Emitter,” Chem. Lett., 905-906 (1993). [cited by applicant]

Holmes, R.J et al., “Blue Organic Electrophosphorescence Using Exothermic Host-Guest Energy Transfer,” Appl. Phys. Lett, 82(15):2422-2424 (2003). [cited by applicant]

Hu, Nan-Xing et al., “Novel High Tg Hole-Transport Molecules Based on Indolo[3,2-b]carbazoles for Organic Light-Emitting Devices,” Synthetic Metals, 111-112:421-424 (2000). [cited by applicant]

Huang, Jinsong et al., “Highly Efficient Red-Emission Polymer Phosphorescent Light-Emitting Diodes Based on Two Novel Tris(1-phenylisoquinolinato-C2,N)iridium(III) Derivatives,” Adv. Mater., 19:739-743 (2007). [cited by applicant]

Huang, Wei-Sheng et al., “Highly Phosphorescent Bis-Cyclometalated Iridium Complexes Containing Benzoimidazole-Based Ligands,” Chem, Mater., 16(12):2480-2488 (2004). [cited by applicant]

Hung, L.S et al., “Anode Modification in Organic Light-Emitting Diodes by Low-Frequency Plasma Polymerization of CHF3,” Appl. Phys. Lett., 78(5):673-675 (2001). [cited by applicant]

Ikai, Masamichi et al., “Highly Efficient Phosphorescence From Organic Light-Emitting Devices with an Exciton-Block Layer,” Appl. Phys. Lett., 79(2):156-158 (2001). [cited by applicant]

Ikeda, Hisao et al., “P-185 Low-Drive-Voltage OLEDs with a Buffer Layer Having Molybdenum Oxide,” SID Symposium Digest, 37:923-926 (2006). [cited by applicant]

Inada, Hiroshi and Shirota, Yasuhiko, “1,3,5-Tris[4-(diphenylamino)phenyl]benzene and its Methylsubstituted Derivatives as a Novel Class of Amorphous Molecular Materials,” J. Mater. Chem., 3(3):319-320 (1993). [cited by applicant]

Kanno, Hiroshi et al., “Highly Efficient and Stable Red Phosphorescent Organic Light-Emitting Device Using bis[2-(2-benzothiazoyl)phenolato]zinc(II) as host material,” Appl. Phys. Lett., 90:123509-1-123509-3 (2007). [cited by applicant]

Kido, Junji et al., 1,2,4-Triazole Derivative as an Electron Transport Layer in Organic Electroluminescent Devices, Jpn. J. Appl. Phys., 32:1917-L920 (1993). [cited by applicant]

Kuwabara, Yoshiyuki et al., “Thermally Stable Multilayered Organic Electroluminescent Devices Using Novel Starburst Molecules, 4,4′,4″-Tri(N-carbazolyl)triphenylamine (TCTA) and 4,4′,4″-Tris(3-methylphenylphenyl-amino) … [cited by applicant]

Kwong, Raymond C. et al., “High Operational Stability of Electrophosphorescent Devices,” Appl. Phys. Left., 81(1) 162-164 (2002). [cited by applicant]

Lamansky, Sergey et al., “Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes,” Inorg. Chem., 40(7):1704-1711 (2001). [cited by applicant]

Lee, Chang-Lyoul et al., “Polymer Phosphorescent Light-Emitting Devices Doped with Tris(2-phenylpyridine) Iridium as a Triplet Emitter,” Appl. Phys. Lett., 77(15):2280-2282 (2000). [cited by applicant]

Lo, Shih-Chun et al., “Blue Phosphorescence from Iridium(III) Complexes at Room Temperature,” Chem, Mater,, 18 (21)5119-5129 (2006). [cited by applicant]

Ma, Yuguang et al., “Triplet Luminescent Dinuclear-Gold(I) Complex-Based Light-Emitting Diodes with Low Turn-On voltage,” Appl. Phys. Lett., 74(10):1361-1363 (1999). [cited by applicant]

Mi, Bao-Xiu et al., “Thermally Stable Hole-Transporting Material for Organic Light-Emitting Diode an Isoindole Derivative,” Chem, Mater,, 15(16):3148-3151 (2003). [cited by applicant]

Nishida, Jun-ichi et al., “Preparation, Characterization, and Electroluminescence Characteristics of α-Diimine-type Platinum(II) Complexes with Perfluorinated Phenyl Groups as Ligands,” Chem. Lett., 34(4): 592-593 (2005… [cited by applicant]

Niu, Yu-Hua et al., “Highly Efficient Electrophosphorescent Devices with Saturated Red Emission from a Neutral Osmium Complex,” Chem, Mater., 17(13):3532-3536 (2005). [cited by applicant]

Noda, Tetsuya and Shirota, Yasuhiko, “5,5′-Bis(dimesitylboryl)-2,2′-bithiophene and 5,5″-Bis (dimesitylboryl)-2,2′5′,2″-terthiophene as a Novel Family of Electron-Transporting Amorphous Molecular Materials,” J. Am. Chem… [cited by applicant]

Okumoto, Kenji et al., “Green Fluorescent Organic Light-Emitting Device with External Quantum Efficiency of Nearly 10%,” Appl. Phys, Lett., 89:063504-1-063504-3 (2006). [cited by applicant]

Palilis, Leonidas C., “High Efficiency Molecular Organic Light-Emitting Diodes Based on Silole Derivatives and Their Exciplexes.” Organic Electronics, 4:113-121 (2003). [cited by applicant]

Paulose, Betty Marie Jennifer S et al., “First Examples of Alkenyl Pyridines as Organic Ligands for Phosphorescent Iridium Complexes,” Adv. Mater,, 16(22):2003-2007 (2004). [cited by applicant]

Ranjan, Sudhir et al., “Realizing Green Phosphorescent Light-Emitting Materials from Rhenium(I) Pyrazolato Diimine Complexes,” Inorg. Chem., 42(4):1248-1255 (2003). [cited by applicant]

Sakamoto, Youichi et al., “Synthesis, Characterization, and Electron-Transport Property of Perfluorinated Phenylene Dendrimers,” J. Am. Chem. Soc., 122(8):1832-1833 (2000). [cited by applicant]

Salbeck, J. et al., “Low Molecular Organic Glasses for Blue Electroluminescence,” Synthetic Metals, 91: 209-215 (1997). [cited by applicant]

Shirota, Yasuhiko et al., “Starburst Molecules Based on pi-Electron Systems as Materials for Organic Electroluminescent Devices,” Journal of Luminescence, 72-74:985-991 (1997). [cited by applicant]

Sotoyama, Wataru et al., “Efficient Organic Light-Emitting Diodes with Phosphorescent Platinum Complexes Containing N{circumflex over (0)}C{circumflex over (0)}N-Coordinating Tridentate Ligand,” Appl. Phys. Lett., 86:15… [cited by applicant]

Sun, Yiru and Forrest, Stephen R., “High-Efficiency White Organic Light Emitting Devices with Three Separate Phosphorescent Emission Layers,” Appl. Phys. Lett., 91:263503-1-263503-3 (2007). [cited by applicant]

T. Östergård et al., “Langmuir-Blodgett Light-Emitting Diodes of Poly(3-Hexylthiophene) Electro-Optical Characteristics Related to Structure,” Synthetic Metals, 88:171-177 (1997). [cited by applicant]

Takizawa, Shin-ya et al., “Phosphorescent Iridium Complexes Based on 2-Phenylimidazo[1,2-α]pyridine Ligands Tuning of Emission Color toward the Blue Region and Application to Polymer Light-Emitting Devices,” Inorg. Chem… [cited by applicant]

Tang, C.W. and VanSlyke, S.A., “Organic Electroluminescent Diodes,” Appl. Phys. Lett,, 51(12):913-915 (1987). [cited by applicant]

Tung, Yung-Liang et al., “Organic Light-Emitting Diodes Based on Charge-Neutral Ru II PHosphorescent Emitters,” Adv. Mater., 17(8)1059-1064 (2005). [cited by applicant]

Van Slyke, S. A. et al., “Organic Electroluminescent Devices with Improved Stability, ” Appl. Phys. Lett., 69(15):2160-2162 (1996). [cited by applicant]

Wang, Y. et al., “Highly Efficient Electroluminescent Materials Based on Fluorinated Organometallic Iridium Compounds,” Appl. Phys. Lett., 79(4):449-461 (2001). [cited by applicant]

Wong, Keith Man-Chung et al., A Novel Class of Phosphorescent Gold(III) Alkynyl-Based Organic Light-Emitting Devices with Tunable Colour, Chem. Commun., 2906-2908 (2005). [cited by applicant]

Wong, Wai-Yeung, “Multifunctional Iridium Complexes Based on Carbazole Modules as Highly Efficient Electrophosphors,” Angew. Chem, Int. Ed., 45:7800-7803 (2006). [cited by applicant]