Organic electroluminescent element and electronic device using same
An organic electroluminescence device comprising: a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises a compound represented by the following formula (1), and a compound A having a Stokes shift of 20 nm or smaller and an emission peak wavelength of 440 nm to 465 nm (at least one of Ar 1 and Ar 2 is a monovalent group having a structure represented by the following formula (2)).
1 . An organic electroluminescence device comprising:
a cathode;
an anode; and
an organic layer disposed between the cathode and the anode, wherein
the organic layer comprises a compound represented by the following formula (1-1) or the following formula (1-2), and
a compound A having a Stokes shift of 20 nm or smaller and an emission peak wavelength of 440 nm to 465 nm
wherein in the formula (1-1) or (1-2),
one or more sets of adjacent two or more of R 1 to R 8 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
R 1 to R 8 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom or a substituent R;
the substituent R is
a halogen atom,
a cyano group,
a nitro group,
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 ),
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;
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 are the same as or different from each other;
L 1 and L 2 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;
X 1 is O;
one or more sets of adjacent two or more of R 11 to R 14 and adjacent two or more of R 15 to R 20 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsaturated, saturated or unsaturated ring;
R 11 to R 20 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom or a substituent R;
the substituent R is as defined in the formula (1-1) or (1-2);
Ar 2 is
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.
2 . The organic electroluminescence device according to claim 1 , wherein L 1 and L 2 are independently
a single bond, or
a substituted or unsubstituted arylene group including 6 to 14 ring carbon atoms.
3 . The organic electroluminescence device according to according to claim 1 , wherein L 1 and L 2 are independently
a single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted fluorenylene group,
a substituted or unsubstituted phenanthrylene group, or
a substituted or unsubstituted biphenyldiyl group.
4 . The organic electroluminescence device according to claim 1 , wherein either or both of L 1 and L 2 are single bonds.
5 . The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (1-1) or (1-2) is a compound represented by the following formula (1-1-1):
wherein in the formula (1-1-1), R 1 to R 8 , L 2 , Ar 2 , X 1 , R 11 to R 17 , R 19 , and R 20 are as defined in the formula (1-1) or (1-2).
6 . The organic electroluminescence device according to claim 1 , wherein L 2 is a single bond.
7 . The organic electroluminescence device according to claim 1 , wherein Ar 2 is
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted chrysenyl group,
a substituted or unsubstituted benzophenanthrenyl group,
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted dibenzofuranyl group,
a substituted or unsubstituted naphthobenzofuranyl group,
a substituted or unsubstituted carbazolyl group, or
a substituted or unsubstituted benzo[def]carbazolyl group.
8 . The organic electroluminescence device according to claim 1 , wherein Ar 2 is a group represented by any of the following formulas (Ar 2 -11) to (Ar 2 -14):
wherein in the formulas (Ar 2 -11) to (Ar 2 -14),
* is bonded with L 2 ;
R a is a substituent;
the substituent R a is
a halogen atom,
a cyano group,
a nitro group,
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 ),
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;
R 901 to R 907 are as defined in the formula (1-1) or (1-2);
m1 is an integer of 0 to 4;
m2 is an integer of 0 to 5;
m3 is an integer of 0 to 7;
when each of m1 to m3 is 2 or more, a plurality of R a 's may be the same as or different from each other;
when m1 to m3 are each 2 or more, a plurality of adjacent R a 's form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring.
9 . The organic electroluminescence device according to claim 1 , wherein Ar 2 -L 2 -,
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenylnaphthyl group,
a substituted or unsubstituted biphenyl group,
a substituted or unsubstituted naphthylphenyl group,
a substituted or unsubstituted fluorenyl group,
a substituted or unsubstituted phenanthryl group,
a substituted or unsubstituted phenylphenanthryl group,
Substituted or unsubstituted benzophenanthryl groups
a substituted or unsubstituted benzotriphenylenyl group,
a substituted or unsubstituted chrysenyl group,
a substituted or unsubstituted dibenzofuranyl group,
a substituted or unsubstituted phenyldibenzofuranyl group,
a substituted or unsubstituted naphthobenzofuranyl group,
a substituted or unsubstituted carbazolyl group,
a substituted or unsubstituted carbazolyl-phenyl group, or
a substituted or unsubstituted benzo[def]carbazolyl-phenyl group.
10 . The organic electroluminescence device according to claim 1 , wherein one or more of
R 1 to R 8 that are hydrogen atoms,
R 11 to R 20 that are hydrogen atoms,
hydrogen atoms possessed by the substituted or unsubstituted, saturated or unsaturated ring formed by bonding one or more sets of adjacent two or more of R 1 to R 8 with each other,
hydrogen atoms possessed by R 1 to R 8 that are the substituents R,
hydrogen atoms possessed by the substituted or unsubstituted, saturated or unsaturated ring formed by bonding one or more sets of adjacent two or more of R 11 to R 20 with each other,
hydrogen atoms possessed by R 11 to R 20 that are the substituents R,
hydrogen atoms possessed by L 1 ,
hydrogen atoms possessed by L 2 , and
hydrogen atoms possessed by Ar 2 are deuterium atoms.
11 . The organic electroluminescence device according to claim 1 , wherein the compound A is one or more selected from the group consisting of a compound represented by the following formula (11), a compound represented by the following formula (21), a compound represented by the following formula (31), and a compound represented by the following formula (41):
wherein in the formula (11),
one or more sets of adjacent two or more of R 101 to R 107 and R 111 to R 117 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
R 121 and R 122 , and R 101 to R 107 and R 111 to R 117 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom or a substituent R; and
the substituent R is as defined in the formula (1-1) or (1-2);
wherein in the formula (21),
a ring a, a ring b, and a ring c are independently
a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted heterocycle including 5 to 50 ring atoms;
R 201 forms a substituted or unsubstituted heterocycle by bonding with either or both of the ring a and the ring b, or do not form a substituted or unsubstituted heterocycle;
R 202 forms a substituted or unsubstituted heterocycle by bonding with either or both of the ring a and the ring c, or do not form a substituted or unsubstituted heterocycle;
R 201 and R 202 that do not form the substituted or unsubstituted heterocycle are independently
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 ),
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
R 901 to R 903 are as defined in the formula (1-1) or (1-2);
wherein in the formula (31),
any one or more sets among one or more sets of adjacent two or more of R 311 to R 320 , one or more sets of adjacent two or more of R 301 to R 305 , and one or more sets of adjacent two or more of R 306 to R 310 form a substituted or unsubstituted, saturated or unsaturated ring including 3 to 30 ring atoms by bonding with each other;
R 311 to R 320 , R 301 to R 305 , and R 306 to R 310 that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom or a substituent R b ;
the substituent R b is
a halogen atom, a cyano group, a nitro group, a carboxy group,
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 ),
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms,
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms,
a substituted or unsubstituted phosphanyl group,
a substituted or unsubstituted phosphoryl group, or
a substituted or unsubstituted arylcarbonyl group including 6 to 50 ring carbon atoms; and
R 901 to R 907 are as defined in the formula (1-1) or (1-2); and
wherein in the formula (41),
a ring d is a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted heterocycle including 5 to 50 ring atoms;
L 401 to L 404 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;
Ar 401 to Ar 404 are independently
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
provided that, when the ring d is a substituted or unsubstituted aromatic hydrocarbon ring including 10 to 50 ring carbon atoms, two or more of Ar 401 to Ar 404 are independently
an aryl group including 6 to 50 carbon atoms substituted by an alkyl group including 1 to 50 carbon atoms, or
a monovalent heterocyclic group including 5 to 50 ring atoms substituted by an alkyl group including 1 to 50 carbon atoms.
12 . The organic electroluminescence device according to claim 11 , wherein the compound represented by the formula (11) is a compound represented by the following formula (12):
wherein in the formula (12), R 101 to R 104 , R 111 to R 114 , R 121 , and R 122 are as defined in the formula (11); and
R 131 to R 134 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.
13 . The organic electroluminescence device according to claim 11 , wherein the compound represented by the formula (11) is a compound represented by the following formula (13):
wherein in the formula (13), R 121 and R 122 are as defined in the formula (1-1) or (1-2), and R 131 to R 134 are as defined in the formula (12).
14 . The organic electroluminescence device according to claim 11 , wherein
the ring a, the ring b, or the ring c in the formula (21) is the substituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or the substituted heterocycle including 5 to 50 ring atoms, and
the substituent is one or more selected from the group consisting of:
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
—Si(R 901 )(R 902 )(R 903 ),
—N(R 906 )(R 907 ) (where R 901 to R 903 , R 906 , and R 907 are as defined in the formula (1-1) or (1-2),
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, and
a substituted or unsubstituted monovalent heterocyclic group including 5 to 60 ring atoms.
15 . The organic electroluminescence device according to claim 11 , wherein the compound represented by the formula (21) is a compound represented by the following formula (22):
wherein in the formula (22),
R 201A forms a substituted or unsubstituted heterocycle by bonding with one or more selected from the group consisting of R 211 and R 221 , or do not form a substituted or unsubstituted heterocycle;
R 202A forms a substituted or unsubstituted heterocycle by bonding with one or more selected from the group consisting of R 213 and R 214 , or do not form a substituted or unsubstituted heterocycle;
R 201A and R 202A that do not form the substituted or unsubstituted heterocycle are independently
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,
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;
one or more sets of adjacent two or more of R 211 to R 221 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
R 211 to R 221 that do not form the substituted or unsubstituted heterocycle, or the substituted or unsubstituted, saturated or unsaturated ring are independently
a hydrogen atom,
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 ),
a halogen atom, a cyano group, a nitro group,
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
R 901 to R 907 are as defined in the formula (1-1) or (1-2).
16 . The organic electroluminescence device according to claim 11 , wherein the compound represented by the formula (21) is a compound represented by the following formula (23A):
wherein in the formula (23A),
R 261 to R 265 are
a hydrogen atom,
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,
—N(R 906 )(R 907 ),
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, or
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms;
R 906 and R 907 are as defined in the formula (1-1) or (1-2); and when two or more of each of R 906 and R 907 are present, the two or more of each of R 906 and R 907 are the same as or different from each other.
17 . The organic electroluminescence device according to claim 11 , wherein the ring d in the formula (41) is a substituted or unsubstituted divalent group having a structure selected from the group consisting of structures represented by the following formulas.
18 . The organic electroluminescence device according to claim 11 , wherein the ring d in the formula (41) is a substituted or unsubstituted pyrene ring.
19 . The organic electroluminescence device according to claim 1 , wherein
the organic layer comprises an emitting layer, and
the emitting layer comprises the compound represented by the formula (1-1) or (1-2) and the compound A.
20 . An electronic apparatus equipped with the organic electroluminescence device according to claim 1 .