Composition, powder, organic electroluminescence device, method of fabricating organic electroluminescence device, and electronic apparatus
A composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (2), provided that the compound represented by the formula (1) and the compound represented by the formula (2) are different compounds:
1 . A composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (2), provided that the compound represented by the formula (1) and the compound represented by the formula (2) are different compounds:
wherein in the formula (1),
X A1 to X A3 are independently N or CR A1 , provided that at least two of X A1 to X A3 are N's;
R A1 is a hydrogen atom or a substituent R;
Ar A1 and Ar A2 are independently
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L A1 and L A2 are independently
a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
L A3 is a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms,
one of R A11 to R A24 is a single bond bonded with L A3 ;
R A11 to R A24 which are not the single bond bonded with L A3 are independently a hydrogen atom or a substituent R;
the substituent R is selected from the group consisting of
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R 901 )(R 902 )(R 903 ),
—O—(R 904 ),
—S—(R 905 ),
—N(R 906 )(R 907 ),
wherein R 901 to R 907 are independently
a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms and when two or more of each of R 901 to R 907 are present, the two or more of each of R 901 to R 907 may be the same as or different from each other,
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and
when two or more of the substituent R's are present, the two or more of the substituent R's may be the same as or different from each other; and
wherein in the formula (2),
X B1 to X B3 are independently N or CR B1 ; provided that at least one of X B1 to X B3 is N;
R B1 is a hydrogen atom or a substituent R;
Ar B1 , Ar B2 , and Ar B3 are independently
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L B1 , L B2 , and L B3 are independently
a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
the substituent R is as defined in the formula (1); and
when two or more R B1 's are present, the two or more R B1 's may be the same as or different from each other.
2 . The composition according to claim 1 , wherein in the formula (1), Ar A1 and Ar A2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
3 . The composition according to claim 1 , wherein in the formula (1), L A1 and L A2 are single bonds.
4 . The composition according to claim 1 , wherein in the formula (1), all of X A1 to X A3 are N's.
5 . The composition according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1):
wherein in the formula (1-1), X A1 to X A3 , Ar A1 , Ar A2 , L A3 , and R A11 to R A24 are as defined in the formula (1).
6 . The composition according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-2):
wherein in the formula (1-2), Ar A1 , Ar A2 , L A3 , and R A11 to R A24 are as defined in the formula (1).
7 . The composition according to claim 1 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-3):
wherein in the formula (1-3), Ar A1 , Ar A2 , and L A3 are as defined in the formula (1); and L A3 is bonded with one of the carbon atoms constituting the benzotriphenylene structure by a single bond.
8 . The composition according to claim 1 , wherein in the formula (2), Ar B3 is a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
9 . The composition according to claim 1 , wherein in the formula (2), Ar B3 is a substituted monovalent heterocyclic group including 5 to 50 ring atoms.
10 . The composition according to claim 1 , wherein in the formula (2), Ar B3 is a monovalent heterocyclic group comprising two carbazole structures.
11 . The composition according to claim 1 , wherein in the formula (2), Ar B3 is a group represented by the following formula:
wherein in the formula, * is a bonding position with L B3 ; R B11 is a hydrogen atom or a substituent R; and the substituent R is as defined in the formula (1).
12 . The composition according to claim 1 , wherein in the formula (2), L B3 is a single bond or a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
13 . The composition according to claim 1 , wherein in the formula (2), L B3 is a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
14 . The composition according to claim 1 , wherein in the formula (2), Ar B1 and Ar B2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
15 . The composition according to claim 1 , wherein in the formula (2), L B1 and L B2 are single bonds.
16 . The composition according to claim 1 wherein in the formula (2), at least two of X B1 to X B3 are N's.
17 . The composition according to claim 1 , wherein in the formula (2), all of X B1 to X B3 are N's.
18 . The composition according to claim 1 , wherein the compound represented by the formula (2) is a compound represented by the following formula (2-1):
wherein in the formula (2-1), X B1 to X B3 , Ar B1 to Ar B3 , and L B3 are as defined in the formula (2).
19 . The composition according to claim 1 , wherein the compound represented by the formula (2) is a compound represented by the following formula (2-2):
wherein in the formula (2-2), X B1 to X B3 , Ar B1 , Ar B2 , and L B3 are as defined in the formula (2); R B11 is a hydrogen atom or a substituent R; and the substituent R is as defined in the formula (1).
20 . The composition according to claim 1 , wherein the compound represented by the formula (2) is a compound represented by the following formula (2-3):
wherein in the formula (2-3), Ar B1 , Ar B2 , and L B3 are as defined in the formula (2); R B11 is a hydrogen atom or a substituent R; and the substituent R is as defined in the formula (1).
21 . An organic electroluminescence device, comprising the composition according to claim 1 .
22 . A powder, composed of the composition according to claim 1 .
23 . A method of fabricating an organic electroluminescence device, comprising a step of forming an organic layer by depositing the powder according to claim 22 from a single deposition source.
24 . An organic electroluminescence device, comprising
a cathode;
an anode;
an emitting layer disposed between the cathode and the anode; and
an electron-transporting region disposed between the emitting layer and the cathode;
wherein the electron-transporting region comprises a compound represented by the following formula (1) and a compound represented by the following formula (2),
provided that the compound represented by the formula (1) and the compound represented by the formula (2) are different compounds:
wherein in the formula (1),
X A1 to X A3 are independently N or CR A1 , provide that at least two of X A1 to X A3 are N's; R A1 is a hydrogen atom or a substituent R;
Ar A1 and Ar A2 are independently
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L A1 , L A2 , and L A3 are independently
a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
one of R A11 to R A24 is a single bond bonded with L A3 ;
R A11 to R A24 which are not the single bond bonded with L A3 are independently a hydrogen atom or a substituent R;
the substituent R is selected from the group consisting of
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R 901 )(R 902 )(R 903 ),
—O—(R 904 ),
—S—(R 905 ),
—N(R 906 )(R 907 ),
wherein R 901 to R 907 are independently
a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when two or more of each of R 901 to R 907 are present, the two or more of each of R 901 to R 907 may be the same as or different from each other,
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and
when two or more of the substituent R's are present, the two or more of the substituent R's may be the same as or different from each other; and
wherein in the formula (2),
X B1 to X B3 are independently N or CR B1 ; provided that at least one of X B1 to X B3 is N; R B1 is a hydrogen atom or a substituent R;
Ar B1 , Ar B2 , and Ar B3 are independently
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L B1 , L B2 , and L B3 are independently
a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
the substituent R is as defined in the formula (1); and
when two or more R B1 's are present, the two or more R B1 's may be the same as or different from each other.
25 . The organic electroluminescence device according to claim 24 , wherein in the formula (1), Ar A1 and Ar A2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
26 . The organic electroluminescence device according to claim 24 , wherein in the formula (1), L A1 and L A2 are single bonds.
27 . The organic electroluminescence device according to claim 24 , wherein in the formula (1), L A3 is a single bond or a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
28 . The organic electroluminescence device according to claim 24 , wherein in the formula (1), L A3 is a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
29 . The organic electroluminescence device according to claim 24 , wherein in the formula (1), all of X A1 to X A3 are N's.
30 . The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1):
wherein in the formula (1-1), X A1 to X A3 , Ar A1 , Ar A2 , L A3 , and R A11 to R A24 are as defined in the formula (1).
31 . The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-2):
wherein in the formula (1-2), Ar A1 , Ar A2 , L A3 , and R A11 to R A24 are as defined in the formula (1).
32 . The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-3):
wherein in the formula (1-3), Ar A1 , Ar A2 , and L A3 are as defined in the formula (1); and L A3 is bonded with one of the carbon atoms on the benzotriphenylene structure.
33 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), Ar B3 is a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
34 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), Ar B3 is a substituted monovalent heterocyclic group including 5 to 50 ring atoms.
35 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), Ar B3 is a monovalent heterocyclic group comprising two carbazole structures.
36 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), Ar B3 is a group represented by the following formula:
wherein in the formula, * is a bonding position with L B3 ; R B11 is a hydrogen atom or a substituent R; and the substituent R is as defined in the formula (1).
37 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), L B3 is a single bond or a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
38 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), L B3 is a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
39 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), Ar B1 and Ar B2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
40 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), L B1 and L B2 are single bonds.
41 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), at least two of X B1 to X B3 are N's.
42 . The organic electroluminescence device according to claim 24 , wherein in the formula (2), all of X B1 to X B3 are N's.
43 . The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (2) is a compound represented by the following formula (2-1):
wherein in the formula (2-1), X B1 to X B3 , Ar B1 to Ar B3 , and L B3 are as defined in the formula (2).
44 . The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (2) is a compound represented by the following formula (2-2):
wherein in the formula (2-2), X B1 to X B3 , Ar B1 , Ar B2 , and L B3 are as defined in the formula (2); R B11 is a hydrogen atom or a substituent R; and the substituent R is as defined in the formula (1).
45 . The organic electroluminescence device according to claim 24 , wherein the compound represented by the formula (2) is a compound represented by the following formula (2-3):
wherein in the formula (2-3), Ar B1 , Ar B2 , and L B3 are as defined in the formula (2); R B11 is a hydrogen atom or a substituent R; and the substituent R is as defined in the formula (1).
46 . The organic electroluminescence device according to claim 24 , wherein the electron-transporting region comprises a first layer and a second layer in this order from the emitting layer side,
the first layer comprises the compound represented by the formula (1) and the compound represented by the formula (2), and
no other layer is disposed between the emitting layer and the first layer.
47 . An electronic apparatus, equipped with the organic electroluminescence device according to claim 24 .
48 . A powder comprising a compound represented by the following formula (1) and a compound represented by the following formula (2), provided that the compound represented by the formula (1) and the compound represented by the formula (2) are different compounds:
wherein in the formula (1),
X A1 to X A3 are independently N or CR A1 , provided that at least two of X A1 to X A3 are N's;
R A1 is a hydrogen atom or a substituent R;
Ar A1 and Ar A2 are independently
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L A1 , L A2 , and L A3 are independently
a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
one of R A11 to R A24 is a single bond bonded with L A3 ;
R A11 to R A24 which are not the single bond bonded with L A3 are independently a hydrogen atom or a substituent R;
the substituent R is selected from the group consisting of
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R 901 )(R 902 )(R 903 ),
—O—(R 904 ),
—S—(R 905 ),
—N(R 906 )(R 907 ),
wherein R 901 to R 907 are independently
a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when two or more of each of R 901 to R 907 are present, the two or more of each of R 901 to R 907 may be the same as or different from each other,
a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and
when two or more of the substituent R's are present, the two or more the substituent R's may be the same as or different from each other; and
wherein in the formula (2),
X B1 to X B3 are independently N or CR B1 ; provided that at least one of X B1 to X B3 is N;
R B1 is a hydrogen atom or a substituent R;
Ar B1 , Ar B2 , and Ar B3 are independently
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L B1 , L B2 , and L B3 are independently
a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
the substituent R is as defined in the formula (1); and
when two or more R B1 's are present, the two or more R B1 's may be the same as or different from each other.
49 . A method of fabricating an organic electroluminescence device, comprising a step of forming an organic layer by depositing a powder according to claim 48 from a single deposition source.
50 . The powder according to claim 48 , wherein in the formula (1), Ar A1 and Ar A2 are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
51 . The powder according to claim 48 , wherein in the formula (1), L A1 and L A2 are single bonds.
52 . The powder according to claim 48 , wherein in the formula (1), L A3 is a single bond or a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
53 . The powder according to claim 48 , wherein in the formula (1), L A3 is a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms.
54 . The powder according to claim 48 , wherein in the formula (1), all of X A1 to X A3 are N's.
55 . The powder according to claim 48 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1):
wherein in the formula (1-1), X A1 to X A3 , Ar A1 , Ar A2 , L A3 , and R A11 to R A24 are as defined in the formula (1).
56 . The powder according to claim 48 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-2):
wherein in the formula (1-2), Ar A1 , Ar A2 , L A3 , and R A11 to R A24 are as defined in the formula (1).
57 . The powder according to claim 48 , wherein the compound represented by the formula (1) is a compound represented by the following formula (1-3):
wherein in the formula (1-3), Ar A1 , Ar A2 , and L A3 are as defined in the formula (1); and L A3 is bonded with one of the carbon atoms constituting the benzotriphenylene structure by a single bond.