Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity

1. A thermally activated delayed fluorescent composition having the general formula of:

wherein:

independently represents one or more acceptor moieties of the compound that contributes to LUMO level of the compound, where A n is nitrogen-containing heteroaryl group, a R q MO group, where M is C, S, P, or As, or a R q SO 2 group, or any combination thereof; and n=1, 2, or 3, such that the compound includes a single acceptor moiety (A 1 ), two acceptor moieties (A 1 and A 2 ), or three acceptor moieties (A 1 , A 2 , and A 3 ), and wherein each acceptor moiety is substituted with R q :

L 1 , L 2 , and L 3 are each independently linkage groups comprising an oxygen (O) containing group, a sulfur (S) containing group, a nitrogen (N) containing group, a carbon (C) containing group, a phosphorous (P) containing group, a silicon (Si) containing group, or a boron (B) containing group; wherein at least one of L 1 , L 2 , and L 3 comprises a boron containing group; and

R m , R n , R p R q , and R q′ each independently represent mono-, di-, tri, or tetra-substitution, and each independently are one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

2. The composition of claim 1 , wherein L 1 , L 2 , and L 3 are each independently

wherein at least one of L 1 , L 2 , and L 3 is represented by

wherein R, R 1 and R 2 each independently represents a hydrogen atom, deuterium, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, an amino group, a mono- or dialkylamino group, a mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, a substituted or unsubstituted heterocyclic group, a carbene group, or a N-heterocyclic carbene, or a combination thereof.

3. The composition of claim 2 , wherein L 1 is represented by

4. The composition of claim 2 , wherein two of L 1 , L 2 , and L 3 are represented by

5. The composition of claim 2 , wherein each of L 1 , L 2 , and L 3 is represented by

6. The composition of claim 2 , wherein in the group

R is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

7. The composition of claim 1 , wherein A n is:

wherein R q′ has the same definition as R q .

8. The composition of claim 1 , wherein A n is a nitrogen-containing heteroaryl group comprising 1 to 3 nitrogen atoms.

9. The composition of claim 1 , wherein A n is

where U, U 1 , and U 2 each independently represents N or C;

with the proviso that at least one of U 1 and U 2 is N.

10. The composition of claim 1 , wherein A n is

11. The composition of claim 1 , wherein n is 2 and the composition has the general structure of:

wherein:

independently represents a second acceptor moiety of the compound that contributes to LUMO level of the compound, where A 2 is nitrogen-containing heteroaryl group, a R u MO group, where M is C, S, P, or As, or a R u SO 2 group, or any combination thereof; and

R u is a mono-, di-, tri, or tetra-substitution, and each substitution is one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxy carbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

12. The composition of claim 1 , wherein n=3, and the composition has the general structure of:

where:

independently represents a second acceptor moiety of the compound that contributes to LUMO level of the compound, where A 2 is nitrogen-containing heteroaryl group, a R u MO group, where M is C, S, P, or As, or a R u SO 2 group, or any combination thereof;

independently represents a third acceptor moiety of the compound, contributes to LUMO level of the compound, where A 3 is nitrogen-containing heteroaryl group, a R v MO group, where M is C, S, P, or As, or a R v SO 2 group, or any combination thereof; and

R u and R v are each independently a mono-, di-, tri, or tetra-substitution, and each substitution is one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

13. The composition of claim 1 , having the general structure of:

where:

L 3 and L 4 are each independently linkage groups comprising an oxygen (O) containing group, a sulfur (S) containing group, a nitrogen (N) containing group, a carbon (C) containing group, a phosphorous (P) containing group, a silicon (Si) containing group, or a boron (B) containing group; and

R m , R n , R s , R t , each independently represents mono-, di-, tri, or tetra-substitution, and each independently represents one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

14. The composition of claim 13 , having the general structure:

where L 5 and L 6 are each independently linkage groups comprising an oxygen (O) containing group, a sulfur (S) containing group, a nitrogen (N) containing group, a carbon (C) containing group, a phosphorous (P) containing group, a silicon (Si) containing group, or a boron (B) containing group; and

R a , R b , R c , R d , R e , R f , R g , R h , and R i each independently represents mono-, di-, tri, or tetra-substitution, and each independently represents one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxy carbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

15. A thermally activated delayed fluorescent composition having a general structure of:

where:

independently represents one or more acceptor moieties of the compound that contributes to LUMO level of the compound, where A n is nitrogen-containing heteroaryl group, a R q MO group, where M is C, S, P, or As, or a R q SO 2 group, or any combination thereof; and n=1, 2, or 3, such that the compound includes a single acceptor moiety (A 1 ), two acceptor moieties (A 1 and A 2 ), or three acceptor moieties (A 1 , A 2 , and A 3 ), and wherein each acceptor moiety is substituted with R q ; and

L 1 and L 2 are each independently linkage groups comprising an oxygen (O) containing group, a sulfur (S) containing group, a nitrogen (N) containing group, a carbon (C) containing group, a phosphorous (P) containing group, a silicon (Si) containing group, or a boron (B) containing group; wherein at least one of L 1 and L 2 comprises a boron containing group; and

ring B and ring B 2 are each independently a substituted electron-deficient aromatic group,

R m , R n , R p , R s , and R t each independently represents mono-, di-, tri, or tetra-substitution, and each independently represents one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

16. The composition of claim 15 , wherein n=2, and the composition has the general structure of:

wherein

independently represents a second acceptor moiety of the compound that contributes to LUMO level of the compound, where A 2 is nitrogen-containing heteroaryl group, a R u MO group, where M is C, S, P, or As, or a R u SO 2 group, or any combination thereof; and

R u is a mono-, di-, tri, or tetra-substitution, and each substitution is one or more of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted mono- or dialkylamino group, a substituted or unsubstituted mono- or diarylamino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxy carbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a ureido group, a phosphoramide group, a mercapto group, a sulfo group, a carboxyl group, a hydrazino group, a substituted silyl group, a polymeric group, or a combination thereof.

17. The composition of claim 15 , wherein ring B is an aryl group.

18. A light emitting device comprising the thermally activated delayed fluorescent composition of claim 1 .

19. The light emitting device of claim 18 , wherein the light emitting device is an organic light emitting diode.

20. The light emitting device of claim 18 , wherein the device comprises a full color display, a photovoltaic device, a luminescent display device or a phosphorescent display device.