Organic electroluminescence device
An organic electroluminescence device includes: a cathode; an anode; and an organic thin-film layer disposed between the cathode and the anode, the organic thin-film layer having one or more layers including an emitting layer, in which the emitting layer includes a first material represented by the following formula (1) and a second material in a form of a fluorescent dopant material.
1. An organic electroluminescence device comprising:
a cathode;
an anode; and
an organic thin-film layer disposed between the cathode and the anode, the organic thin-film layer having one or more layers comprising an emitting layer,
the emitting layer comprising a first material represented by a formula (1) below and a second material in a form of a fluorescent dopant material,
where, in the formula (1):
A is a group having a partial structure selected from formulae (a-1) to (a-7) below;
B is a group having a partial structure selected from formulae (b-1) to (b-6) below;
L represents a single bond or a linking group;
the linking group is:
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a group derived from a group formed by mutually bonding two to five of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and/or the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
the mutually bonded groups being the same or different;
a is an integer in a range from 1 to 5 representing the number of a substituent(s) of A directly bonded to L;
a plurality of A being mutually the same or different when a is 2 or more,
b is an integer in a range from 1 to 5 representing the number of a substituent(s) of B directly bonded to L,
a plurality of B being mutually the same or different when b is 2 or more;
where
R is: a hydrogen atom;
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and
when a plurality of R are present, the plurality of R being mutually the same or different.
2. The organic electroluminescence device according to claim 1 , wherein B in the formula (1) is represented by one of formulae (2), (3), (4), (5) and (6) below,
where: R 1 and R 9 each independently represent:
a hydrogen atom;
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms;
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms;
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms;
a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms;
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms; or
a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, at least one of the combinations of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 and R 9 and R 1 optionally forming a saturated or unsaturated ring structure;
L 1 is a linking group selected from formulae (21) to (27) below,
n1 represents an integer in a range from 1 to 3, and, when n1 is 2 or 3, plural L 1 are mutually the same or different, and
X 1 is a linking group selected from formulae (41) to (45) below,
where, in the formulae (23) to (27), R 101 is the same as R 1 to R 9 in the formula (2),
with a proviso that, in the formula (2), one of R 1 to R 9 or one of R 101 is a single bond to be bonded to L, and
when a plurality of R 101 are present, the plurality of R 101 are mutually the same or different,
where, in the formulae (43) to (45), R x represents:
a hydrogen atom;
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and
when a plurality of R x are present, the plurality of R x are mutually the same or different,
where, in the above formula (3), R 21 to R 24 are the same as R 1 to R 9 in the formula (2), one of the combinations of R 21 and R 22 , R 22 and R 23 , and R 23 and R 24 optionally forming a saturated or unsaturated cyclic structure; and
X 1 is a linking group selected from the formulae (41) to (45), with a proviso that, in the above formula (3), one of R 21 to R 24 and R x is a single bond to be bonded to L,
where, in the formula (4):
R 25 to R 30 represent the same as R 1 to R 9 in the formula (2), one of the combinations of R 25 and R 26 , R 27 and R 28 , R 28 and R 29 , and R 29 and R 30 optionally forming a saturated or unsaturated cyclic structure; and
X 1 is a linking group selected from the formulae (41) to (45), with a proviso that, in the above formula (4), one of R 25 to R 30 and R x is a single bond to be bonded to L,
where, in the formula (5):
R 31 to R 38 are the same as R 1 to R 9 in the formula (2), one of the combinations of R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , and R 35 and R 36 , R 36 and R 37 , and R 37 and R 38 optionally forming a saturated or unsaturated cyclic structure; and
X 1 is a linking group selected from the formulae (41) to (45), with a proviso that, in the above formula (5), one of R 31 to R 38 and R x is a single bond to be bonded to L,
(Z b ) r —Ar b — (6)
where, in the formula (6):
Ar b represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
Zb represents:
a substituted or unsubstituted tertiary alkyl group having 4 to 30 carbon atoms;
a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms;
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms;
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylamino group having 2 to 60 carbon atoms;
a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms;
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms; or
a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
r is an integer in a range from 1 to 5 representing the number of a substituent(s) of Z b directly bonded to A b , and
a plurality of Z b being mutually the same or different when r is 2 or more.
3. The organic electroluminescence device according to claim 2 , wherein
the formula (2) is represented by a formula (2a) below,
where, R 10 is the same as R 1 to R 9 in the formula (2),
m1 and m3 represent an integer in a range from 0 to 4, m2 represents an integer in a range from 0 to 2,
plural R 10 being mutually the same or different, and
X 1 is a linking group selected from the formulae (41) to (45), plural X 1 being mutually the same or different, with a proviso that, in the formula (2a), one of R 10 and R x in the formulae (43) to (45) is a single bond to be bonded to L.
4. The organic electroluminescence device according to claim 2 , wherein
at least one of R 31 to R 38 in the formula (5) is represented by a formula (51) below,
where: R 39 represents the same as R 1 to R 9 in the formula (2),
r represents an integer in a range from 0 to 3 and S represents an integer in a range from 0 to 4,
plural R 39 being mutually the same or different;
X 1 is a linking group selected from the formulae (41) to (45),
L 61 represents a single bond or a linking group, and
the linking group is:
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a group derived from a group formed by mutually bonding two to five of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and/or the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
the mutually bonded groups being mutually the same or different.
5. The organic electroluminescence device according to claim 1 , wherein
A in the formula (1) is represented by one of formulae (8), (9), (10), (11), (12), (13) and (14) below,
where, in the formula (8): two to four of Y 1 are a nitrogen atom, one of Y 1 is a carbon atom bonded to L and the rest of Y 1 is CR y ;
when the formula (8) includes a plurality of R y , the plurality of R y independently represent: a hydrogen atom;
a fluorine atom;
a cyano group;
a nitro group;
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms;
a substituted or unsubstituted alkylcarbonyl group having 1 to 30 carbon atoms;
a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms;
a substituted or unsubstituted arylsulfinyl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylphosphinyl group having 2 to 60 carbon atoms;
a substituted or unsubstituted arylphosphinyl group having 6 to 60 ring carbon atoms;
a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms;
a substituted or unsubstituted arylsulfonyl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylsilyl group having 3 to 60 carbon atoms;
a substituted or unsubstituted arylsilyl group having 8 to 60 ring carbon atoms;
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; or
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms; and
adjacent two Y 1 optionally form a saturated or unsaturated cyclic structure when the adjacent two Y 1 are CR y ,
where, in the formula (9), Y 2 is the same as the other Y 1 in the formula (8),
where, in the formulae (10), (11) and (12):
Y 3 represents the same as Y 1 in the formula (8); and
X 3 is a linking group selected from formulae (41) to (45) below,
where, in the above formulae (43) to (45):
R x independently represents:
a hydrogen atom;
a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and
when a plurality of R x are present, the plurality of R x are mutually the same or different,
where, in the formula (13):
one of R 41 to R 48 is a single bond to be bonded to L;
the rest of R 41 to R 48 represent the same as R y in the formula (8);
L 4 is a linking group selected from formulae (131) to (136) below; and
p represents an integer in a range from 1 to 3, a plurality of L 4 being mutually the same or different when p is 2 or 3,
where, in the above formulae (133) to (136):
each of R 301 independently represents:
a hydrogen atom;
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and
when a plurality of R 301 are present, the plurality of R 301 are mutually the same or different,
—Ar a —(Z a ) q (14)
where, in the formula (14):
Ar a represents:
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Zr a represents:
a fluorine atom;
a cyano group;
a nitro group;
a substituted or unsubstituted alkylcarbonyl group having 1 to 20 carbon atoms;
a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylsulfinyl group having 1 to 20 carbon atoms;
a substituted or unsubstituted arylsulfinyl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted alkylphosphinyl group having 2 to 60 carbon atoms;
a substituted or unsubstituted arylphosphinyl group having 6 to 60 ring carbon atoms;
a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms; or
a substituted or unsubstituted arylsulfonyl group having 6 to 30 ring carbon atoms;
q is an integer in a range from 1 to 5 representing the number of a substituent(s) of Z a directly bonded to Ar a ; and
a plurality of Z a are mutually the same or different when q is 2 or more.
6. The organic electroluminescence device according to claim 1 , wherein
the second material in the form of the fluorescent dopant material is represented by a formula (20) below,
where, in the formula (20):
Ar 0 is a substituted or unsubstituted divalent fused aromatic hydrocarbon group having 10 to 50 ring carbon atoms; and
Ar 1 to Ar 4 each independently represent:
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
a substituted or unsubstituted alkyl group having 6 to 30 carbon atoms; or
a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms.
7. The organic electroluminescence device according to claim 1 , wherein
the organic electroluminescence device exhibits a delayed fluorescence ratio larger than 37.5%.
8. The organic electroluminescence device according to claim 1 , wherein
the organic electroluminescence device exhibits a residual strength ratio larger than 36.0% after an elapse of 1 μs after voltage removal in a transitional EL measurement.
9. The organic electroluminescence device according to claim 1 , wherein
a half bandwidth of a photoluminescence spectrum of the first material is 50 nm or more.
10. An organic electroluminescence device comprising:
a cathode;
an anode; and
an organic thin-film layer disposed between the cathode and the anode, the organic thin-film layer having one or more layers comprising an emitting layer,
the emitting layer comprising a first material represented by a formula (1) below and a second material in a form of a dopant material,
with a proviso that the dopant material is not a heavy metal complex,
where, in the formula (1):
A is a group having a partial structure selected from formulae (a-1) to (a-7) below;
B is a group having a partial structure selected from formulae (b-1) to (b-6) below;
L represents a single bond or a linking group;
the linking group is:
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a group derived from a group formed by mutually bonding two to five of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and/or the substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, the mutually bonded groups being mutually the same or different;
a is an integer in a range from 1 to 5 representing the number of a substituent(s) of A directly bonded to L;
a plurality of A being mutually the same or different when a is 2 or more; and
b is an integer in a range from 1 to 5 representing the number of a substituent(s) of B directly bonded to L,
a plurality of B being mutually the same or different when b is 2 or more,
where, in the formulae (b-1) to (b-6):
R is:
a hydrogen atom;
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; or
a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; and
when a plurality of R are present, the plurality of R are mutually the same or different.