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US 11,600,780 B1Granted
Organic electroluminescence device and electronic apparatus
AssigneeIdemitsu Kosan Co., Ltd.
InventorsSatomi Tasaki, Taro Yamaki, Hiroaki Itoi, Yuki Nakano, Yuichiro Kawamura
Life of this patent
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Abstract
An organic electroluminescence device including: an anode, a cathode, and at least one emitting layer between the cathode and the anode, wherein the emitting layer contains a first host material, a second host material, and a dopant material, the first host material is a compound having at least one deuterium atom, and the emitting layer contains the first host material in the proportion of 1% by mass or more.
Claims24
An organic electroluminescence device comprising:
- an anode, a cathode, and a first fluorescent emitting layer between the cathode and the anode, wherein
- the first fluorescent emitting layer comprises a first host material, a second host material, and a fluorescent dopant material,
- the first host material is a compound represented by the following formula (1) having at least one deuterium atom, and
- the second host material is a compound represented by the following formula (1′):
- wherein in the formula (1),
- R1 to R8 are independently
- a hydrogen atom,
- 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(R901)(R902)(R903),
- —O—(R904),
- —S—(R905),
- —N(R906)(R907),
- 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,
- R901 to R907 are independently
- a hydrogen atom,
- an unsubstituted alkyl group including 1 to 50 carbon atoms,
- an unsubstituted cycloalkyl group including 3 to 50 ring 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 R901 to R907 are present, the two or more of each of R901 to R907 are the same as or different from each other,
- adjacent two or more of R1 to R4, and adjacent two or more of R5 to R8 do not form a ring by bonding with each other,
- L1 and L2 are independently
- a single bond,
- an unsubstituted arylene group including 6 to 30 ring carbon atoms, or
- an unsubstituted divalent heterocyclic group including 5 to 30 ring atoms,
- Ar1 and Ar2 are independently
- an unsubstituted phenyl group,
- an unsubstituted biphenyl group,
- an unsubstituted naphthyl group, or
- an unsubstituted dibenzofuranyl group,
- and
- at least one hydrogen atom selected from the following is a deuterium atom:
- hydrogen atoms of R1 to R8 in the case where they are hydrogen atoms, and
- hydrogen atoms possessed by one or more groups selected from R1 to R8 which are not hydrogen atoms, L1 which is not a single bond, L2 which is not a single bond, and Ar1 and Ar2;
- and
- wherein in the formula (1′),
- R1 to R8 are independently
- a hydrogen atom,
- 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(R901)(R902)(R903),
- —O—(R904),
- —S—(R905),
- —N(R906)(R907),
- 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,
- R901 to R907 are independently
- a hydrogen atom,
- an unsubstituted alkyl group including 1 to 50 carbon atoms,
- an unsubstituted cycloalkyl group including 3 to 50 ring 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 R901 to R907 are present, the two or more of each of R901 to R907 are the same as or different from each other;
- adjacent two or more of R1 to R4, and adjacent two or more of R5 to R8 do not form a ring by bonding with each other;
- L1 and L2 are independently
- a single bond,
- an unsubstituted arylene group including 6 to 30 ring carbon atoms, or
- an unsubstituted divalent heterocyclic group including 5 to 30 ring atoms;
- Ar1 and Ar2 are independently
- an unsubstituted phenyl group,
- an unsubstituted biphenyl group,
- an unsubstituted naphthyl group, or
- an unsubstituted dibenzofuranyl group,
- wherein the second host material is a compound that does not substantially comprise a deuterium atom,
- -L1-Ar1 in the first host material represented by the formula (1) has the same chemical structure as -L1-Ar1 in the second host material represented by the formula (1′) except that when -L1-Ar1 in the first host material comprises at least one deuterium atom, each of such at least one deuterium atom in -L1-Ar1 of the first host material is replaced by a protium atom in -L1-Ar1 of the second host material, and
- the chemical structure when all of the deuterium atoms of the first host material is replaced with protium atom is different from the chemical structure of the second host material.
71 more elements
A composition for an emitting layer of an organic electroluminescence device, comprising:
- a first host material, and
- a second host material, wherein,
- the first host material is a compound represented by the following formula (1) having at least one deuterium atom, and
- the second host material is a compound represented by the following formula (1′):
- wherein in the formula (1),
- R1 to R8 are independently
- a hydrogen atom,
- 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(R901)(R902)(R903),
- —O—(R904),
- —S—(R905),
- —N(R906)(R907),
- 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,
- R901 to R907 are independently
- a hydrogen atom,
- an unsubstituted alkyl group including 1 to 50 carbon atoms,
- an unsubstituted cycloalkyl group including 3 to 50 ring 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 R901 to R907 are present, the two or more of each of R901 to R907 are the same as or different from each other,
- adjacent two or more of R1 to R4, and adjacent two or more of R5 to R8 do not form a ring by bonding with each other,
- L1 and L2 are independently
- a single bond,
- an unsubstituted arylene group including 6 to 30 ring carbon atoms, or
- an unsubstituted divalent heterocyclic group including 5 to 30 ring atoms,
- Ar1 and Ar2 are independently
- an unsubstituted phenyl group,
- an unsubstituted biphenyl group,
- an unsubstituted naphthyl group, or
- an unsubstituted dibenzofuranyl group,
- and
- at least one hydrogen atom selected from the following is a deuterium atom:
- hydrogen atoms of R1 to R8 in the case where they are hydrogen atoms, and
- hydrogen atoms possessed by one or more groups selected from R1 to R8 which are not hydrogen atoms, L1 which is not a single bond, L2 which is not a single bond, and Ar1 and Ar2;
- and
- wherein in the formula (1′),
- R1 to R8 are independently
- a hydrogen atom,
- 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(R901)(R902)(R903),
- —O—(R904),
- —S—(R905),
- —N(R906)(R907),
- 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,
- R901 to R907 are independently
- a hydrogen atom,
- an unsubstituted alkyl group including 1 to 50 carbon atoms,
- an unsubstituted cycloalkyl group including 3 to 50 ring 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 R901 to R907 are present, the two or more of each of R901 to R907 are the same as or different from each other,
- adjacent two or more of R1 to R4, and adjacent two or more of R5 to R8 do not form a ring by bonding with each other,
- L1 and L2 are independently
- a single bond,
- an unsubstituted arylene group including 6 to 30 ring carbon atoms, or
- an unsubstituted divalent heterocyclic group including 5 to 30 ring atoms, and
- Ar1 and Ar2 are independently
- an unsubstituted phenyl group,
- an unsubstituted biphenyl group,
- an unsubstituted naphthyl group, or
- an unsubstituted dibenzofuranyl group,
- wherein the second host material is a compound that does not substantially comprise a deuterium atom,
- -L1-Ar1 in the first host material represented by the formula (1) has the same chemical structure as -L1-Ar1 in the second host material represented by the formula (1′) except that when -L1-Ar1 in the first host material comprises at least one deuterium atom, each of such at least one deuterium atom in -L1-Ar1 of the first host material is replaced by a protium atom in -L1-Ar1 of the second host material and the chemical structure when all of the deuterium atoms of the first host material is replaced with protium atom is different from the chemical structure of the second host material.
70 more elements
Dependencies are inferred from the claim text.