Organic electroluminescence device and electronic apparatus provided with the same
An organic electroluminescence device containing a cathode, an anode, and an emitting layer disposed between the cathode and the anode, wherein the emitting layer contains a compound represented by the following formula (1) and one or more compounds selected from the group consisting of a compound represented by the specific formulas (11), (21), (31), (41), (51), (61), (71), and (81).
1 . An organic electroluminescence device comprising
a cathode,
an anode, and
an emitting layer disposed between the cathode and the anode, wherein
the emitting layer comprises a compound represented by the following formula (1) and
one or more compounds selected from the group consisting of a compound represented by the formula following (21), a compound represented by the formula following (31), a compound represented by the formula following (41), and a compound represented by the formula following (51):
wherein in the formula (1),
X 1 is an oxygen atom or a sulfur atom;
Ar 1 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;
L 1 is 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;
R 1 to R 8 and R 11 to R 19 are independently
a hydrogen atom, 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 or different;
wherein in the formula (21),
Zs are independently CR a or N;
A1 ring and A2 ring are independently a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms;
when plural R a s exist, one or more sets of two or more adjacent groups of R a are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
when plural R b s exist, one or more sets of two or more adjacent groups of R b are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
when plural R c s exist, one or more sets of two or more adjacent groups of R c are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
n21 and n22 are independently an integer of 0 to 4;
R a to R c that do not form the substituted or unsubstituted, saturated or unsaturated ring 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 ),
—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);
wherein in the formula (31),
one or more sets of two or more adjacent groups of R 301 to R 307 and R 311 to R 317 form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
R 301 to R 307 and R 311 to R 317 that do not form 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;
R 321 and R 322 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);
wherein in the formula (41),
a ring, b ring and c ring are independently
a substituted or unsubstituted aromatic hydrocarbon ring including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted heterocyclic ring including 5 to 50 ring atoms;
R 401 and R 402 are independently bonded to the a ring, the b ring or the c ring to form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring;
R 401 and R 402 that do not form the substituted or unsubstituted heterocyclic ring 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;
wherein in the formula (51),
r ring is a ring represented by the formula (52) or formula (53) which is fused to an adjacent ring at an arbitrary position;
q ring and s ring are independently a ring represented by the formula (54) which is fused to an adjacent ring at an arbitrary position;
p ring and t ring are independently a ring represented by the formula (55) or the formula (56) which is fused to an adjacent ring at an arbitrary position;
when plural R 501 's exist, adjacent plural R 501 's are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
X 501 is an oxygen atom, a sulfur atom, or NR 502 ;
R 501 and R 502 that do not form the substituted or unsubstituted saturated or unsaturated ring are
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;
R 901 to R 907 are as defined in the formula (1);
Ar 501 and Ar 502 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;
L 501 is
a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenylene group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynylene group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkylene group including 3 to 50 ring carbon atoms,
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;
m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3 is independently an integer of 0 to 3, and m4 is independently an integer of 0 to 5; when plural R 501 's exist, the plural R 501 's may be the same or different.
2 . The organic electroluminescence device according to claim 1 , wherein
L 1 is
a single bond, or
a substituted or unsubstituted arylene group including 6 to 14 ring carbon atoms.
3 . The organic electroluminescence device 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 1 , Ar 1 , R 1 to R 8 , and R 11 to R 19 are as defined in the formula (1).
4 . The organic electroluminescence device according to claim 1 , wherein
Ar 1 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms.
5 . The organic electroluminescence device according to claim 1 , wherein
Ar 1 is selected from the group represented by the following formulas (a1) to (a4):
wherein in the formulas (a1) to (a4), “*” is bonded to a carbon atom of the anthracene skeleton;
R 21 is
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;
R 901 to R 907 are as defined in the formula (1);
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 21 's may be the same as or different from each other;
when each of m1 to m3 are 2 or more, a plurality of adjacent R 21 '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.
6 . The organic electroluminescence device according to claim 1 , wherein
R 1 to R 8 and R 11 to R 19 are hydrogen atoms,
L 1 is a single bond, an unsubstituted arylene group including 6 to 50 ring carbon atoms, or an unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
Ar 1 is an unsubstituted aryl group including 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms.
7 . The organic electroluminescence device according to claim 1 , wherein X 1 is an oxygen atom.
8 . The organic electroluminescence device according to claim 1 , wherein
the emitting layer comprises
the compound represented by the formula (1) and,
one or more compounds selected from the group consisting of the compound represented by the formula (21), the compound represented by the formula (31), the compound represented by the formula (51), and a compound represented by the following formula (43a):
wherein in the formula (43a),
R 431 forms a substituted or unsubstituted heterocyclic ring by bonding with R 446 , or does not form a substituted or unsubstituted heterocyclic ring; R 433 forms a substituted or unsubstituted heterocyclic ring by bonding with R 447 , or does not form a substituted or unsubstituted heterocyclic ring; R 434 forms a substituted or unsubstituted heterocyclic ring by bonding with R 451 , or does not form a substituted or unsubstituted heterocyclic ring; R 441 forms a substituted or unsubstituted heterocyclic ring by bonding with R 442 , or does not form a substituted or unsubstituted heterocyclic ring;
one or more sets of adjacent two or more among R 431 to R 451 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 431 to R 451 which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted, saturated or unsaturated ring are independently
a hydrogen atom, 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);
provided that at least one of R 431 to R 451 which does not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted, saturated or unsaturated ring 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.
9 . The organic electroluminescence device according to claim 1 , wherein the compound represented by the formula (21) is a compound represented by the following formula (21-3), (21-4), or (21-5):
wherein in the formulas (21-3), (21-4), and (21-5),
A1a ring is a substituted or unsubstituted fused aromatic hydrocarbon ring including 10 to 50 ring carbon atoms, or a substituted or unsubstituted fused heterocyclic ring including 8 to 50 ring atoms;
one or more sets of two or more adjacent groups of R 2401 to R 2407 and R 2410 to R 2416 are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;
R 2417 and R 2401 to R 2407 and R 2410 to R 2416 that do not form 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).
10 . The organic electroluminescence device according to claim 9 , wherein the compound represented by the formula (21-3) is a compound represented by the following formula (21-3-1):
wherein in the formula (21-3-1), R 2403 , R 2405 , R 2406 , R 2412 , R 2414 and R 2415 are as defined in the formula (21-3).
11 . The organic electroluminescence device according to claim 9 , wherein the compound represented by the formula (21-3) is a compound represented by the following formula (21-3-3):
wherein in the formula (21-3-3), R 2401 to R 2404 , R 2410 to R 2413 and R 2417 are as defined in the formula (21-3);
R A , R B , R C and R D are independently
a substituted or unsubstituted or aryl group including 6 to 18 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 18 ring atoms.
12 . The organic electroluminescence device according to claim 1 , wherein
the substituent in the case of “substituted or unsubstituted” is
an unsubstituted alkyl group including 1 to 50 carbon atoms,
an unsubstituted alkenyl group including 2 to 50 carbon atoms,
an unsubstituted alkynyl group including 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R 901a )(R 902a )(R 903a ),
—O—(R 904a ),
—S—(R 905a ),
—N(R 906a )(R 907a ),
a halogen atom, a cyano group, a nitro group,
an unsubstituted aryl group including 6 to 50 ring carbon atoms, or
an unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms, wherein
R 901a to R 907a are independently
a hydrogen atom,
an unsubstituted alkyl group including 1 to 50 carbon atoms,
an unsubstituted aryl group including 6 to 50 ring carbon atoms, or
an unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when two or more of each of R 901a to R 907a are present, the two or more of each of R 901a to R 907a are the same or different.
13 . The organic electroluminescence device according to claim 1 , further comprising a hole-transporting layer between the anode and the emitting layer.
14 . The organic electroluminescence device according to claim 1 , further comprising an electron-transporting layer between the cathode and the emitting layer.
15 . An electronic apparatus, wherein the organic electroluminescence device according to claim 1 is provided.