Thermally activated delayed fluorescent material based on 9,10-dihydro-9,9-dimethylacridine analogues for prolonging device longevity
Thermally activated delayed fluorescent compounds and uses thereof are described. The thermally activated delayed fluorescent compounds are an analogs of 9,10-dihydro-9,9-dimethylacridine compounds.
1. A thermally activated delayed fluorescent compound represented by Formula I:
wherein:
represents n acceptor moieties A,
where A is a nitrogen-containing heteroaryl group, and n=2 or 3, such that Formula I includes 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 optionally substituted with one or more R;
L 1 represents —C(R) 2 — or —CO—;
R m , R n , R p , and R q each independently represents a mono-, di-, tri, or tetra-substitution, valency permitting; and
each R, R m , R n , R p , and R q independently represents 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 compound of claim 1 , wherein
represents one of the following structures:
3. The compound of claim 2 , wherein each A n present comprises 1, 2, or 3 nitrogen atoms.
4. The compound of claim 1 , wherein
represents:
wherein U, U 1 , and U 2 each independently represents N or C.
5. The compound of claim 4 , wherein
represents:
6. The compound of claim 1 , wherein n=2 and the compound is represented by Formula V:
7. The compound of claim 1 , wherein n=3, and the compound is represented by Formula VIII:
8. A thermally activated delayed fluorescent compound represented by Formula XV:
wherein:
represents an acceptor moiety A 1 ,
where A 1 is a nitrogen-containing heteroaryl group, wherein A 1 is substituted with R q ;
L 1 represents —C(R) 2 — or —CO—;
R m , R n , R p , and R q each independently represents a mono-, di-, tri, or tetra-substitution, valency permitting; and
each R, R m , R n , R p , and R q independently represents 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.
9. A thermally activated delayed fluorescent compound represented by Formula XIX:
wherein:
represents an acceptor moiety A 1 ,
where A 1 is a nitrogen-containing heteroaryl group;
L 1 represents —C(R) 2 — or —CO—;
R m , R n , and R p each independently represents a mono-, di-, tri, or tetra-substitution, valency permitting; and
each R, R m , R n , and R p independently represents 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.
10. A light emitting device comprising the thermally activated delayed fluorescent compound of claim 1 .
11. The light emitting device of claim 10 , wherein the light emitting device is an organic light emitting diode.
12. The light emitting device of claim 10 , wherein the device comprises a full color display, a photovoltaic device, a luminescent display device, or a phosphorescent display device.
13. The compound of claim 10 , wherein the compound is:
14. A light emitting device comprising the thermally activated delayed fluorescent compound of claim 10 .
15. The light emitting device of claim 14 , wherein the light emitting device is an organic light emitting diode.
16. The light emitting device of claim 14 , wherein the device comprises a full color display, a photovoltaic device, a luminescent display device, or a phosphorescent display device.
17. A light emitting device comprising the thermally activated delayed fluorescent compound of claim 9 .
18. The light emitting device of claim 17 , wherein the light emitting device is an organic light emitting diode.
19. The light emitting device of claim 17 , wherein the device comprises a full color display, a photovoltaic device, a luminescent display device, or a phosphorescent display device.