IP Library › Granted Patent US 10,294,417
Granted Patent B2
US 10,294,417 · App. 15/925,203 · Granted May 21, 2019

Metal-assisted delayed fluorescent materials as co-host materials for fluorescent OLEDS

Inventor: Jian Li (Tempe, AZ)
Assignee: Arizona Board of Regents on behalf of Arizona State University
C09K11/06H01L51/005H01L51/0052H01L51/0062H01L51/0065H01L51/0067H01L51/0068H01L51/0069H01L51/0071H01L51/0072H01L51/0073H01L51/0074H01L51/0083H01L51/0084H01L51/0085H01L51/0087H01L51/0091H01L51/0092H01L51/504H01L51/5012C09K2211/185C09K2211/187C09K2211/188H01L51/0054
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Quick Facts
Patent No.
US 10,294,417
App. No.
15/925,203
Granted
May 21, 2019
Kind
B2
Abstract

A light emitting device includes a first electrode, a hole transporting layer in contact with the first electrode, a second electrode, an electron transporting layer in contact with the second electrode; and an emissive layer between the hole transporting layer and the electron transporting layer. The emissive layer includes a metal-assisted delayed fluorescent (MADF) emitter, a fluorescent emitter, and a host, and the MADF emitter harvests electrogenerated excitons and transfers energy to the fluorescent emitter.

Claims (109)

1. A light emitting device comprising:

a first electrode;

a hole transporting layer in contact with the first electrode;

a second electrode;

an electron transporting layer in contact with the second electrode; and

an emissive layer between the hole transporting layer and the electron transporting layer, wherein the emissive layer comprises a donor, an acceptor, and a host,

wherein:

the donor is a metal-assisted delayed fluorescent (MADF) emitter that demonstrates an emission spectrum consisting of dual emission characteristics from delayed fluorescence and phosphorescence,

the acceptor is a fluorescent emitter,

the delayed fluorescence emission energy of the donor is greater than the emission energy of the acceptor and the phosphorescence emission energy of the donor is greater than or less than the emission energy of the acceptor, such that an emission spectrum of the donor partially overlaps in wavelength with an absorption spectrum of the acceptor, and

dipole coupling between the donor in an excited state and the acceptor in a ground state allows a transfer of energy from the donor to the acceptor.

2. The light emitting device of claim 1 , wherein the transfer of energy from the donor to the acceptor is a transfer of energy from an allowed relaxation transition of the donor to an allowed excitation transition of the acceptor.

3. The light emitting device of claim 1 , wherein the transfer of energy occurs between mixed singlet/triplet excitons of the donor and singlet excitons of the acceptor.

4. The light emitting device of claim 1 , wherein the transfer of energy occurs between a triplet exciton of the donor and a singlet exciton of the acceptor.

5. The light-emitting device of claim 1 , wherein the donor, in a triplet state, is less stable than the acceptor, in a singlet state.

6. The light-emitting device of claim 1 , wherein a dopant concentration of the acceptor is reasonably small, i.e. 3 weight percent or less, to encourage Foster energy transfer and suppress Dexter energy transfer between donor and acceptor.

7. The light-emitting device of claim 1 , wherein light emission from the light-emitting device is primarily from the acceptor.

8. The light emitting device of claim 1 , wherein the donor is a compound of structure (a) or (b):

wherein:

M is platinum (II), palladium (II), nickel (II), manganese (II), zinc (II), gold (III), silver (III), copper (III), iridium (I), rhodium (I), or cobalt (I);

A is an accepting group having one of the following structures, which can optionally be substituted:

D is a donor group having one of the following structures, which can optionally be substituted:

C has one of the following structures, which can optionally be substituted:

N has one of the following structures, which can optionally be substituted:

each of a 0 , a 1 , and a 2 is independently present or absent, and if present, is a direct bond or linking group having one of the following structures:

each of b 1 and b 2 is independently present or absent, and if present, is a linking group having one of the following structures:

X is B, C, N, O, Si, P, S, Ge, As, Se, Sn, Sb, or Te,

Y is N, P, P═O, As, As═O, CH, CR, SiH, SiR, GeH, GeR,

each R is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof, and

n is an integer that satisfies the valency of Y.

9. The light emitting device of claim 8 , wherein a 2 is absent.

10. The light emitting device of claim 8 , wherein a 2 and b 2 are absent.

11. The light emitting device of claim 8 , wherein X is N.

12. The light emitting device of claim 8 , wherein A is

a 2 is absent, b 2 is absent, and D is

13. The light emitting device of claim 8 , wherein C in structure (a) or (b) is

14. The light emitting device of claim 8 , wherein N in structure (a) or (b) is

or substituted

15. The light emitting device of claim 8 , wherein M is palladium (II).

16. The light emitting device of claim 8 , wherein the donor is one of the following:

17. The light emitting device of claim 8 , wherein the donor is a compound of General Formula A:

wherein:

M is Ir, Rh, Mn, Ni, Cu, or Ag;

each R 1 and R 2 is independently hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 1a and Y 1b is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , or a combination thereof, wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c and Y 2d is independently N or CR 5 , wherein R 5 is hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 4a , Y 4b , Y 4c and Y 4d is independently N, O, S, NR 6 , or CR 7 , wherein each of R 6 and R 7 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R 8 ) 2 , wherein Z is C or Si, and wherein each R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of m and n is independently 1 or 2; and

each independently represents partial or full unsaturation of the ring with which it is associated.

18. The light emitting device of claim 17 , wherein Y 2b is C; Y 2c , Y 3b and Y 4b are N; and M is Ir or Rh.

19. The light emitting device of claim 8 , wherein the MADF emitter is a compound of General Formula B:

wherein:

M is Pt, Pd, or Au;

each of R 1 and R 2 is independently hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 1a and Y 1b is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , or a combination thereof, wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c and Y 2d is independently N or CR 5 , wherein R 5 is hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 3f , Y 4a , Y 4b , Y 4c , and Y 4d is independently N, O, S, NR 6 , CR 7 , wherein each of R 6 and R 7 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R 8 ) 2 , wherein Z is C or Si, and wherein each R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

m is 1 or 2; and

each independently represents partial or full unsaturation of the ring with which it is associated.

20. The light emitting device of claim 19 , wherein M is Pt or Pd, Y 2b and Y 2c are C, Y 3b and Y 4b are N, each of Y 1a and Y 1b is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , or a combination thereof, wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure.

21. The light emitting device of claim 19 , wherein M is Au, Y 2b Y 2c and Y 4b are C, Y 3b is N, each of Y 1a and Y 1b is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , or a combination thereof, wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure.

22. The light emitting device of claim 8 , wherein the donor is a compound of General Formula C:

wherein:

M is Pt, Pd, Au, or Ag;

each of R 1 and R 2 is independently hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

one of Y 1a and Y 1b is B(R 3 ) 2 and the other of Y 1a and Y 1b is O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c and Y 2d is independently N or CR 5 , wherein R 5 is hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 4a , Y 4b , Y 4c and Y 4d is independently N, O, S, NR 6 , CR 7 , wherein each of R 6 and R 7 independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R 8 ) 2 , wherein Z is C or Si, and wherein each R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of m and n is independently 1 or 2; and

each independently represents partial or full unsaturation of the ring with which it is associated.

23. The light emitting device of claim 8 , wherein the donor is a compound of General Formula D:

wherein:

M is Ir, Rh, Pt, Os, Zr, Co, or Ru;

each of R 1 and R 2 is independently hydrogen, halogen, hydroxyl, nitro, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 1a , Y 1b , Y 1c and Y 1d is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

Y 1e , if present, is O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c and Y 2d is independently N or CR 5 , wherein R 5 is hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c and Y 4d is independently N, O, S, NR 6 , or CR 7 , wherein each of R 6 and R 7 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R 8 ) 2 , wherein Z is C or Si, and wherein each R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 5a , Y 5b , Y 5c , Y 5d , Y 6a , Y 6b , Y 6c and Y 6d is independently N, O, S, NR 5 , or CR 6 ;

each of m, n, l, and p is independently 1 or 2; and

each independently represents partial or full unsaturation of the ring with which it is associated.

24. The light emitting device of claim 8 , wherein the donor is a compound of General Formula E:

wherein:

M is Pt, Pd, Ir, Rh, Au, Co, Mn, Ni, Ag, or Cu;

each of Y 1a and Y 1b is independently O, NR 3 , CR 3 R 4 , S, AsR 3 , BR 3 , PR 3 , P(O)R 3 , or SiR 3 R 4 , wherein each of R 3 and R 4 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, arylalkene, or R 3 and R 4 together form C═O, wherein each of R 3 and R 4 is independently optionally linked to an adjacent ring structure, thereby forming a cyclic structure;

each of Y 2a , Y 2b , Y 2c , Y 2d , Y 2e , Y 2f , Y 2g and Y 2h is independently N or CR 5 , wherein R 5 is hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene;

each of Y 3a , Y 3b , Y 3c , Y 3d , Y 3e , Y 4a , Y 4b , Y 4c , Y 4d and Y 4e is independently N, O, S, NR 6 , or CR 7 , wherein each of R 6 and R 7 independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, amino, alkoxy, haloalkyl, arylalkane, or arylalkene; or Z(R 8 ) 2 , wherein Z is C or Si, and wherein each R 8 is independently hydrogen, halogen, hydroxyl, thiol, or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkane, cycloalkane, heterocyclyl, aminoalkoxy, haloalkyl, arylalkane, or arylalkene;

m is 1 or 2;

n is 1 or 2;

each independently represents partial or full unsaturation of the ring with which it is associated; and

each of Fl 1 , Fl 2 , Fl 3 and Fl 4 is independently present or absent, with at least one of Fl 1 , Fl 2 , Fl 3 and Fl 4 present, and if present each of Fl 1 , Fl 2 , Fl 3 and Fl 4 is a fluorescent emitter covalently bonded to one of Y 2a , Y 2d , Y 2e , Y 2f , Y 2g , Y 2h , Y 3c , Y 3d , Y 3e , Y 4c , Y 4d and Y 4e .

25. The light emitting device of claim 8 , wherein the donor has an energy of the singlet excited state(s) no more than 0.2 eV greater than the energy of the lowest triplet state, and the MADF emitter emits simultaneously from the lowest triplet state and the singlet excited state(s) at room temperature or elevated temperature.

26. The light emitting device of claim 25 , wherein the donor harvests electrogenerated singlet and triplet excitons.

27. The light emitting device of claim 24 , wherein each of Fl 1 , Fl 2 , Fl 3 , Fl 4 , if present, has one of the following structures:

1. Aromatic Hydrocarbons and Their Derivatives

2. Arylethylene, Arylacetylene and Their Derivatives

3. Heterocyclic Compounds and Their Derivatives

4. Other fluorescent luminophors

wherein:

each of R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 and R 81 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof, and

each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o and Y p is independently C, N or B; and

each of U a , U b and U c is independently CH 2 , CRR, C═O, SiRR, GeH 2 , GeRR 2 , NH, NR, PH, PR, RP═O, AsR, RAs═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR, RBi═O, BiH, or BiR, wherein each R is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryl oxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof.

28. The light emitting device of claim 1 , wherein the acceptor comprises one of the following compounds:

3. Heterocyclic Compounds and Their Derivatives

4. Other fluorescent luminophors

wherein:

each of R 11 , R 21 , R 31 , R 41 , R 51 , R 61 , R 71 and R 81 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof, and

each of Y a , Y b , Y c , Y d , Y e , Y f , Y g , Y h , Y i , Y j , Y k , Y l , Y m , Y n , Y o and Y p is independently C, N or B; and

each of U a , U b and U c is independently CH 2 , CRR, C═O, SiRR, GeH 2 , GeRR, NH, NR, PH, PR, RP═O, AsR, RAs═O, O, S, S═O, SO 2 , Se, Se═O, SeO 2 , BH, BR, RBi═O, BiH, or BiR, wherein each R is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryl oxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric, or any conjugate or combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2018
From: LI, JIAN
To: ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY
Reel/Frame 047132/0200 →
Continuity (3)
Continuation 15505544
Provisional Application 62040727 · Aug 22, 2014
Related Publication 20180312750A1 · Nov 1, 2018
Cited By (12)
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