Organic electroluminescent device configured to emit light with high luminous efficiency
Abstract
An organic electroluminescence device includes an anode, a cathode, a first emitting layer and a second emitting layer that are interposed between the anode and the cathode and are in a direct contact with each other, and a first electron transporting layer between the cathode and the first emitting layer and the second emitting layer being in a direct contact with each other. The first emitting layer contains a first compound represented by a formula (1) as a first host material, the first compound having at least one group represented by a formula (11). The second emitting layer contains a second compound represented by a formula (2) as a second host material. The first electron transporting layer contains a third compound represented by a formula (3).
Claims
exact text as granted — not AI-modified1 . An organic electroluminescence device comprising:
an anode; a cathode; a first emitting layer and a second emitting layer interposed between the anode and the cathode; and a first electron transporting layer between the first and second emitting layers and the cathode, wherein the first emitting layer comprises a first compound as a first host material, the second emitting layer comprises a second compound as a second host material, the first host material and the second host material are different from each other, only one of the first emitting layer and the second emitting layer at least comprises a compound that emits light having a maximum peak wavelength of 500 nm or less, a triplet energy T 1 (H1) of the first host material and a triplet energy T 1 (H2) of the second host material satisfy a numerical formula below (Numerical Formula 1A), and the first electron transporting layer comprises a third compound represented by a formula (3) below,
T 1 ( H 1)> T 1 ( H 2) (Numerical Formula 1A)
where: A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
L is a single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (n+1)-valent group having a structure in which two or three different groups selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms are bonded to each other;
C is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms;
n is 1, 2 or 3;
when n is 2 or more, L is not a single bond; and
when n is 2 or more, a plurality of C are mutually the same or different.
2 . The organic electroluminescence device according to claim 1 , wherein
the first emitting layer and the second emitting layer are in a direct contact with each other.
3 . The organic electroluminescence device according to claim 1 , wherein
the first host material comprises, in a molecule, a linking structure comprising a benzene ring and a naphthalene ring linked to each other with a single bond, the benzene ring and the naphthalene ring in the linking structure are each independently fused or not fused with a further monocyclic ring or fused ring, and the benzene ring and the naphthalene ring in the linking structure are further linked to each other by cross-linking at at least one site other than the single bond.
4 . The organic electroluminescence device according to claim 3 , wherein
the cross-linking comprises a double bond.
5 . The organic electroluminescence device according to claim 1 , wherein
the first host material comprises, in a molecule, a biphenyl structure in which a first benzene ring and a second benzene ring are linked to each other with a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at at least one site other than the single bond.
6 . The organic electroluminescence device according to claim 5 , wherein
the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at one site other than the single bond.
7 . The organic electroluminescence device according to claim 5 , wherein
the cross-linking comprises a double bond.
8 . The organic electroluminescence device according to claim 5 , wherein
the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at two sites other than the single bond, and the cross-linking does not comprise a double bond.
9 . The organic electroluminescence device according to claim 1 , wherein
the first compound is a compound represented by a formula (1) below,
where: in the formula (1):
R 101 to R 110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a group represented by —S—(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R 801 , a group represented by —COOR 802 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or the group represented by a formula (11) above;
at least one of R 101 to R 110 is the group represented by the formula (11);
when a plurality of groups represented by the formula (11) are present, the plurality of groups represented by the formula (11) are mutually the same or different;
L 101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
mx is 0, 1, 2, 3, 4 or 5;
when two or more L 101 are present, two or more L 101 are mutually the same or different;
when two or more Ar 101 are present, two or more Ar 101 are mutually the same or different;
* in the formula (11) represents a bonding position to a pyrene ring in the formula (1);
in the first compound represented by the formula (1), R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;
when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;
when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different;
when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different;
when a plurality of R 905 are present, the plurality of R 905 are mutually the same or different;
when a plurality of R 801 are present, the plurality of R 801 are mutually the same or different; and
when a plurality of R 802 are present, the plurality of R 802 are mutually the same or different.
10 . The organic electroluminescence device according to claim 1 , wherein
the second compound is a compound represented by a formula (2) below,
where: R 201 to R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a group represented by —S—(R 905 ), a group represented by —N(R 906 )(R 907 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R 801 , a group represented by —COOR 802 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L 201 and L 202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
Ar 201 and Ar 202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
in the second compound represented by the formula (2), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;
when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;
when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different;
when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different;
when a plurality of R 905 are present, the plurality of R 905 are mutually the same or different;
when a plurality of R 906 are present, the plurality of R 906 are mutually the same or different;
when a plurality of R 907 are present, the plurality of R 907 are mutually the same or different;
when a plurality of R 801 are present, the plurality of R 801 are mutually the same or different; and
when a plurality of R 802 are present, the plurality of R 802 are mutually the same or different.
11 . The organic electroluminescence device according to claim 1 , wherein
the third compound is a compound represented by a formula (31) or a formula (310),
where: in the formula (31):
A, B and C represent the same as A, B and C defined in the formula (3);
at least one combination of adjacent two or more of R 31 to R 34 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
R 31 to R 34 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
where: in the formula (310):
A and B represent the same as A and B defined in the formula (3);
X 30 is CR 51 R 52 , NR 53 , an oxygen atom, or a sulfur atom;
when X 30 is CR 51 R 52 , a combination of R 51 and R 52 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R 300 to R 304 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R 53 , and R 51 , R 52 , and R 300 to R 304 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
na is 3; and three R 300 are mutually the same or different;
in the third compound, R 901 , R 902 , R 903 , and R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;
when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;
when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and
when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different.
12 . The organic electroluminescence device according to claim 1 , wherein
the third compound is a compound represented by a formula (37) below,
where: in the formula (37):
A, B and L represent the same as A, B and L defined in the formula (3);
Cz is a group represented by a formula (Cz1), (Cz2), or (Cz3);
n is 1, 2 or 3; and
when n is 2 or 3, a plurality of Cz are mutually the same or different,
where: in the formulae (Cz1), (Cz2), and (Cz3):
at least one combination of adjacent two or more of R 311 to R 318 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R 320 to R 324 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R 330 to R 334 and Rx are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R 340 to R 344 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R 351 to R 358 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R 311 to R 318 , R 320 to R 324 , R 330 to R 334 , R X , R 340 to R 344 and R 351 to R 358 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
n1, n2 and n3 are 3;
three R 320 are mutually the same or different;
three R 330 are mutually the same or different;
three R 340 are mutually the same or different; and
* in the formulae (Cz1), (Cz2), and (Cz3) is bonded to L,
in the third compound, R 901 , R 902 , R 903 , and R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;
when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;
when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and
when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different.
13 . The organic electroluminescence device according to claim 1 , wherein
the compound represented by the formula (3) is a compound represented by a formula (38) below,
where: in the formula (38):
A and B represent the same as A and B defined in the formula (3);
La is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms; and
Ac is a group represented by one of formulae (Ac1), (Ac2), and (Ac3) below,
where: in the formula (Ac1):
X 31 to X 36 are each independently a nitrogen atom, a carbon atom bonded to La, or a carbon atom bonded to Ry;
at least one of X 31 to X 36 is a nitrogen atom;
one of X 31 to X 36 is a carbon atom bonded to La;
Ry is a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
when a plurality of Ry are present, the plurality of Ry are mutually the same or different;
in the formula (Ac2):
X 21 to X 28 are each independently a nitrogen atom, a carbon atom bonded to La, or a carbon atom bonded to Rz;
at least one of X 21 to X 28 is a nitrogen atom;
one of X 21 to X 28 is a carbon atom bonded to La;
when a plurality of Rz are present, at least one combination of adjacent two or more of the plurality of Rz are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
Rz neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring is each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
in the formula (Ac3):
n4 is 1, 2, 3, 4, 5, 6, 7, 8 or 9;
D is an aryl group having a cyano group whose number is n4 and having 6 to 18 ring carbon atoms, or a heterocyclic group having a cyano group whose number is n4 and having 5 to 13 ring atoms;
D has a substituent other than a cyano group or does not have a substituent other than a cyano group; and
* in the formula (Ac3) is bonded to La;
in the third compound, R 901 , R 902 , R 903 , and R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;
when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;
when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and
when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different.
14 . The organic electroluminescence device according to claim 1 , further comprising:
a second electron transporting layer between the first electron transporting layer and the cathode.
15 . The organic electroluminescence device according to claim 14 , wherein
the first electron transporting layer and the second electron transporting layer are in direct contact with each other.
16 . The organic electroluminescence device according to claim 1 , wherein
the first emitting layer is interposed between the anode and the second emitting layer.
17 . The organic electroluminescence device according to claim 1 , wherein
the second emitting layer is interposed between the anode and the first emitting layer.
18 . The organic electroluminescence device according to claim 1 , further comprising:
a hole transporting layer between the anode and the first and second emitting layers, wherein the hole transporting layer comprises a compound represented by a formula (C1) or a formula (D1),
where: in the formula (C1):
L A , L B , and L C are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms;
A A , B B , and C C are each independently 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 represented by —Si(R′ 901 )(R′ 902 )(R′ 903 );
R′ 901 to R′ 903 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
when a plurality of R′ 901 are present, the plurality of R′ 901 are mutually the same or different;
when a plurality of R′ 902 are present, the plurality of R′ 902 are mutually the same or different; and
when a plurality of R′ 903 are present, the plurality of R′ 903 are mutually the same or different,
where: in the formula (D 1 ):
A 41 and A 42 are each independently 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;
L 41 and L 42 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;
at least one combination of adjacent two or more of Ra 410 to Ra 414 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of Ra 420 to Ra 424 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
Ra 410 to Ra 414 and Ra 420 to Ra 424 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R 901 )(R 902 )(R 903 ), a group represented by —O—(R 904 ), a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
m1 and m2 are 3;
three Ra 410 are mutually the same or different; and
three Ra 420 are mutually the same or different,
in the compound represented by the formula (D1), R 901 , R 902 , R 903 , and R 904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R 901 are present, the plurality of R 901 are mutually the same or different;
when a plurality of R 902 are present, the plurality of R 902 are mutually the same or different;
when a plurality of R 903 are present, the plurality of R 903 are mutually the same or different; and
when a plurality of R 904 are present, the plurality of R 904 are mutually the same or different.
19 . An organic electroluminescence device comprising:
an anode; a cathode; a first emitting layer and a second emitting layer interposed between the anode and the cathode; and a first electron transporting layer between the first and second emitting layers and the cathode, wherein the first emitting layer comprises a first compound as a first host material, the second emitting layer comprises a second compound as a second host material, the first host material and the second host material are different from each other, only one of the first emitting layer and the second emitting layer at least comprises a compound that emits light having a maximum peak wavelength of 500 nm or less, a triplet energy T 1 (H1) of the first host material and a triplet energy T 1 (H2) of the second host material satisfy a numerical formula below (Numerical Formula 1A), and the first electron transporting layer comprises an azine derivative,
T 1 ( H 1)> T 1 ( H 2) (Numerical Formula 1A).
20 . An electronic device comprising the organic electroluminescence device according to claim 1 .Join the waitlist — get patent alerts
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