WO2021132667A1 - 有機エレクトロルミネッセンス素子、組成物、粉体、電子機器、及び新規化合物 - Google Patents

有機エレクトロルミネッセンス素子、組成物、粉体、電子機器、及び新規化合物 Download PDF

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WO2021132667A1
WO2021132667A1 PCT/JP2020/048995 JP2020048995W WO2021132667A1 WO 2021132667 A1 WO2021132667 A1 WO 2021132667A1 JP 2020048995 W JP2020048995 W JP 2020048995W WO 2021132667 A1 WO2021132667 A1 WO 2021132667A1
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unsubstituted
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ring
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English (en)
French (fr)
Japanese (ja)
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ヨングク リー
竜志 前田
裕基 中野
裕亮 糸井
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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Priority to KR1020227004306A priority Critical patent/KR102687912B1/ko
Priority to EP20904724.0A priority patent/EP3998322B1/en
Priority to CN202511216182.0A priority patent/CN121085874A/zh
Priority to US17/633,887 priority patent/US12581850B2/en
Priority to KR1020257004304A priority patent/KR20250024867A/ko
Priority to JP2021567727A priority patent/JP7328358B2/ja
Priority to KR1020247024227A priority patent/KR102855088B1/ko
Priority to CN202080056746.8A priority patent/CN114207862B/zh
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Publication of WO2021132667A1 publication Critical patent/WO2021132667A1/ja
Anticipated expiration legal-status Critical
Priority to JP2023126053A priority patent/JP7618745B2/ja
Priority to JP2025002309A priority patent/JP2025061693A/ja
Priority to US19/220,684 priority patent/US20250295024A1/en
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Definitions

  • the present invention relates to organic electroluminescent devices, compositions, powders, electronic devices, and novel compounds.
  • an organic electroluminescence element hereinafter referred to as an organic EL element
  • holes are injected from the anode and electrons are injected from the cathode into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.
  • Patent Document 1 discloses a technique in which two types of host materials are used in combination in a light emitting layer.
  • An object of the present invention is to provide an organic EL device having a low drive voltage and high external quantum efficiency. Another object of the present invention is to provide a novel compound capable of improving the life of an organic EL device.
  • the present inventors combined two compounds having a specific structure (a first host material and a second host material) in the light emitting layer of the organic EL element.
  • the present invention has been completed by finding that an organic EL device having a low drive voltage and high external quantum efficiency can be obtained by using the above.
  • the following organic EL devices, compositions, powders, electronic devices, and novel compounds are provided.
  • the light emitting layer contains a first host material, a second host material, and a dopant material.
  • the first host material is a compound represented by the following formula (1).
  • the second host material is a compound represented by the following formula (2), and the first host material and the second host material are different compounds.
  • Organic electroluminescence element is a compound represented by the following formula (1).
  • R 1A to R 8A are independent of each other. Hydrogen atom, Substituent R, or a group represented by the following formula (1A).
  • the substituent R is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms,
  • L 1A is independent of each other Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1A is independent of each other A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other.
  • X 11B is an oxygen atom or a sulfur atom.
  • Two or more adjacent pairs of R 14B to R 17B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.
  • Two or more adjacent pairs of R 11B to R 13B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 1B to R 8B and R 11B to R 17B which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • L 1B and L 2B are independent of each other. Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1B is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are as defined by the above equation (1). )
  • a compound represented by the following formula (1), a compound represented by the following formula (2), a compound represented by the following formula (1), and a compound represented by the following formula (2) are included.
  • R 1A to R 8A are independent of each other. Hydrogen atom, Substituent R, or a group represented by the following formula (1A).
  • the substituent R is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms,
  • L 1A is independent of each other Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1A is independent of each other A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other.
  • X 11B is an oxygen atom or a sulfur atom.
  • Two or more adjacent pairs of R 14B to R 17B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.
  • Two or more adjacent pairs of R 11B to R 13B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 11B to R 17B which do not form the substituted or unsaturated saturated or unsaturated ring, are independently of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 1B to R 8B are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic
  • L 1B and L 2B are independent of each other. Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1B is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are as defined by the above equation (1). )
  • a powder comprising the composition according to 2 above. 4. With the cathode With the anode At least one light emitting layer arranged between the cathode and the anode, Have, The light emitting layer is an organic electroluminescence device containing the composition according to 2. 5. An electronic device including the organic electroluminescence device according to 1 or 4 above.
  • X 11C is an oxygen atom or a sulfur atom.
  • L 1C and L 2C are independent of each other. Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • the hydrogen atom possessed by L 1C which is not a single bond, may be a deuterium atom.
  • Two or more adjacent pairs of R 11C to R 13C combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring.
  • R 1C to R 8C , R 14C , R 15C , and R 18C to R 21C , and R 11C to R 13C which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different.
  • R 1C to R 8C , R 14C , R 15C , and R 18C to R 21C , and R 11C to R 13C that do not form the substituted or unsubstituted saturated or unsaturated ring are hydrogen atoms, this is the case.
  • Hydrogen atom is not deuterium atom;
  • the hydrogen atoms contained in R 1C to R 8C, R 14C , R 15C , and R 18C to R 21C , which are not hydrogen atoms , and R 11C to R 13C, which do not form the substituted or unsubstituted saturated or unsaturated ring, are Not a deuterium atom;
  • R 1C to R 8C , R 14C , R 15C , and R 18C to R 21C which are not hydrogen atoms , and R 11C to R 13C, which do not form the substituted or unsubstituted saturated or unsaturated ring, are optional substituents.
  • the hydrogen atom of the optional substituent is not a deuterium atom;
  • Hydrogen atom ring has a R 11C ⁇ R 13C are bonded is formed of the substituted or unsubstituted, saturated or unsaturated with one another is not a deuterium; and wherein the R 11C ⁇ R 13C are bonded is formed to each other
  • the hydrogen atom of the optional substituent is not a deuterium atom.
  • X 11C is an oxygen atom or a sulfur atom.
  • L 1C is Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1C is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • at least one of the hydrogen atoms of the group -L 1C- Ar 1C is a deuterium atom.
  • R 11C to R 13C Two or more adjacent pairs of R 11C to R 13C combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 1C to R 8C , R 14C , and R 17C to R 21C , and R 11C to R 13C , which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different.
  • R 1C to R 8C , R 14C , and R 17C to R 21C , and R 11C to R 13C which do not form the substituted or unsaturated saturated or unsaturated ring are hydrogen atoms
  • the hydrogen atom is the hydrogen atom.
  • R 11C to R 13C which do not form a substituted or unsubstituted saturated or unsaturated ring, are deuterium atoms.
  • R 1C to R 8C , R 14C , and R 17C to R 21C which are not hydrogen atoms
  • R 11C to R 13C which do not form the substituted or unsubstituted saturated or unsaturated ring, have arbitrary substituents.
  • the hydrogen atom of the arbitrary substituent is not a deuterium atom; Hydrogen atom ring has a R 11C ⁇ R 13C are bonded is formed of the substituted or unsubstituted, saturated or unsaturated with one another is not a deuterium; and wherein the R 11C ⁇ R 13C are bonded is formed to each other When the substituted or unsubstituted saturated or unsaturated ring has an arbitrary substituent, the hydrogen atom of the optional substituent is not a deuterium atom.
  • an organic EL device having a low drive voltage and high external quantum efficiency. Furthermore, according to the present invention, it is possible to provide a novel compound capable of improving the life of the organic EL device.
  • a hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a light hydrogen atom, a deuterium atom, or a deuterium atom is located at a bondable position in which a symbol such as "R” or a "D” representing a deuterium atom is not specified in the chemical structural formula. It is assumed that the deuterium atom is bonded.
  • the ring-forming carbon number constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound). Represents the number of carbon atoms among the atoms to be used. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbons forming the ring.
  • the "ring-forming carbon number" described below shall be the same unless otherwise specified.
  • the benzene ring has 6 ring-forming carbon atoms
  • the naphthalene ring has 10 ring-forming carbon atoms
  • the pyridine ring has 5 ring-forming carbon atoms
  • the furan ring has 4 ring-forming carbon atoms.
  • the ring-forming carbon number of the 9,9-diphenylfluorenyl group is 13
  • the ring-forming carbon number of the 9,9'-spirobifluorenyl group is 25.
  • the carbon number of the alkyl group is not included in the ring-forming carbon number of the benzene ring.
  • the ring-forming carbon number of the benzene ring substituted with the alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the carbon number of the alkyl group is not included in the ring-forming carbon number of the naphthalene ring. Therefore, the ring-forming carbon number of the naphthalene ring substituted with the alkyl group is 10.
  • the number of ring-forming atoms is a compound (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocycle) having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, and a ring assembly).
  • a compound for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocycle
  • Atoms that do not form a ring for example, a hydrogen atom that terminates the bond of atoms that form a ring
  • atoms included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms.
  • the "number of ring-forming atoms" described below shall be the same unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6.
  • a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of the quinazoline ring to which the hydrogen atom or the substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression "ZZ group having a substituted or unsubstituted carbon number XX to YY” represents the carbon number when the ZZ group is unsubstituted and is substituted. Does not include the carbon number of the substituent in the case.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • the number of atoms XX to YY in the expression "the ZZ group having the number of atoms XX to YY substituted or unsubstituted” represents the number of atoms when the ZZ group is unsubstituted and is substituted. Does not include the number of atoms of the substituent in the case.
  • "YY” is larger than “XX”
  • "XX” means an integer of 1 or more
  • YY" means an integer of 2 or more.
  • the unsubstituted ZZ group represents the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group", and the substituted ZZ group is the "substituted or unsubstituted ZZ group". Represents the case where is a "substitution ZZ group”.
  • the term "unsubstituted” in the case of "substituent or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with the substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.
  • substitution in the case of “substituent or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with the substituent.
  • substitution in the case of “BB group substituted with AA group” means that one or more hydrogen atoms in the BB group are replaced with AA group.
  • the ring-forming carbon number of the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated herein. ..
  • the number of ring-forming atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise stated herein. is there.
  • the carbon number of the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
  • the carbon number of the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
  • the carbon number of the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
  • the ring-forming carbon number of the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise stated herein. is there.
  • the ring-forming carbon number of the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. ..
  • the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5. ⁇ 18.
  • the carbon number of the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in the present specification include the following unsubstituted aryl group (specific example group G1A) and a substituted aryl group (specific example group G1B). ) Etc. can be mentioned.
  • the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group”
  • the substituted aryl group is the "substituted or unsubstituted aryl group”.
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group”.
  • the "substituted aryl group” means a group in which one or more hydrogen atoms of the "unsubstituted aryl group” are replaced with a substituent.
  • Examples of the “substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” of the following specific example group G1A are replaced with a substituent, and a substituted aryl group of the following specific example group G1B. And the like.
  • aryl group (Specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, Anthril group, Benzoanthril group, Phenantril group, Benzophenanthril group, Fenarenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, Parakisilyl group, Meta-kisilyl group, Ortho-kisilyl group, Para-isopropylphenyl group, Meta-isopropylphenyl group, Ortho-isopropylphenyl group, Para-t-butylphenyl group, Meta-t-butylphenyl group, Ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-Diphenylfluorenyl group 9,9-bis (4-methylphenyl) fluorenyl group, 9,9-Bis (4-isopropylphenyl) fluorenyl group, 9,9-bis (4-t-butylphenyl) fluorenyl group, Cyanophenyl group, Triphenylsilylphen
  • heterocyclic group is a cyclic group containing at least one heteroatom in the ring-forming atom.
  • the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
  • the "heterocyclic group” described herein is a monocyclic group or a condensed ring group.
  • the “heterocyclic group” described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in the present specification include the following unsubstituted heterocyclic group (specific example group G2A) and a substituted heterocyclic group (specific example group G2). Specific example group G2B) and the like can be mentioned.
  • the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is the "unsubstituted heterocyclic group”
  • the substituted heterocyclic group is "substituted or unsubstituted”.
  • heterocyclic group is a “substituted heterocyclic group”.
  • heterocyclic group is simply referred to as “unsubstituted heterocyclic group” and “substituted heterocyclic group”. Including both.
  • substituted heterocyclic group means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group” are replaced with a substituent.
  • substituted heterocyclic group examples include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” of the following specific example group G2A is replaced, an example of the substituted heterocyclic group of the following specific example group G2B, and the like. Can be mentioned.
  • the examples of the "unsubstituted heterocyclic group” and the “substituent heterocyclic group” listed here are merely examples, and the "substituent heterocyclic group” described in the present specification specifically refers to the "substituted heterocyclic group”.
  • the specific example group G2A is, for example, an unsubstituted heterocyclic group containing the following nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), and a non-substituted heterocyclic group containing a sulfur atom. (Specific example group G2A3) and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33). (Specific example group G2A4) is included.
  • the specific example group G2B is, for example, a substituted heterocyclic group containing the following nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), and a substituted heterocycle containing a sulfur atom.
  • One or more hydrogen atoms of the group (specific example group G2B3) and the monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are the substituents. Includes replaced groups (specific example group G2B4).
  • -Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazoleyl group, Oxazolyl group, Isooxazolyl group, Oxaziazolyl group, Thiazolyl group, Isothiazolyl group, Thiasia Zoryl group, Pyridyl group, Pyridadinyl group, Pyrimidinyl group, Pyrazinel group, Triazinyl group, Indrill group, Isoin drill group, Indridinyl group, Kinolidinyl group, Quinoline group, Isoquinolyl group, Synnolyl group, Phtaladinyl group, Kinazolinyl group, Kinoxalinyl group, Benzoimidazolyl group, Indazolyl group, Phenantrolinyl group, Phenantridinyl group, Acridiny
  • -Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): Frill group, Oxazolyl group, Isooxazolyl group, Oxaziazolyl group, Xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naftbenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholine group, Ginaftfuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftbenzofuranyl group and diazanaphthobenzofuranyl group.
  • Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naftbenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiadinyl group, Dinaftthiophenyl group (dinaftthienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaftbenzothiophenyl group
  • the X A and Y A each independently, an oxygen atom, a sulfur atom, NH, or is CH 2. Provided that at least one of X A and Y A represents an oxygen atom, a sulfur atom, or is NH.
  • at least one is NH of X A and Y A, or a CH 2, in the general formula (TEMP-16) ⁇ (TEMP -33)
  • the monovalent heterocyclic group derived from the ring structure represented includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2.
  • -Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl) carbazolyl group, (9-biphenylyl) carbazolyl group, (9-Phenyl) Phenylcarbazolyl group, (9-naphthyl) carbazolyl group, Diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methylbenzoimidazolyl group, Ethylbenzoimidazolyl group, Phenyltriazinyl group, Biphenylyl triazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group and biphenylylquinazolinyl group.
  • the "one or more hydrogen atoms of the monovalent heterocyclic group” means that at least one of hydrogen atoms, XA and YA bonded to the ring-forming carbon atom of the monovalent heterocyclic group is NH. It means one or more hydrogen atoms selected from the hydrogen atom bonded to the nitrogen atom of the case and the hydrogen atom of the methylene group when one of XA and YA is CH2.
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in the present specification include the following unsubstituted alkyl group (specific example group G3A) and a substituted alkyl group (specific example group G3B). ).
  • the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group”
  • the substituted alkyl group is a "substituted or unsubstituted alkyl group”.
  • alkyl group includes both "unsubstituted alkyl group” and "substituted alkyl group”.
  • the "substituted alkyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkyl group” include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group” (specific example group G3A) are replaced with a substituent, and a substituted alkyl group (specific example). Examples of group G3B) can be mentioned.
  • the alkyl group in the "unsubstituted alkyl group” means a chain alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
  • the examples of the "unsubstituted alkyl group” and the “substituted alkyl group” listed here are only examples, and the "substituted alkyl group” described in the present specification includes the specific example group G3B.
  • Unsubstituted alkyl group (specific example group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-Butyl group, Isobutyl group, s-Butyl group and t-Butyl group.
  • Substituent alkyl group (specific example group G3B): Propylfluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.
  • Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in the present specification include the following unsubstituted alkenyl group (specific example group G4A) and a substituted alkenyl group (specific example group). G4B) and the like can be mentioned.
  • the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group” is a "substituted or unsubstituted alkenyl group”. Refers to the case where "is a substituted alkenyl group”.
  • alkenyl group includes both "unsubstituted alkenyl group” and "substituted alkenyl group”.
  • the "substituted alkenyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include a group in which the following "unsubstituted alkenyl group” (specific example group G4A) has a substituent, an example of a substituted alkenyl group (specific example group G4B), and the like. Be done.
  • the examples of the "unsubstituted alkenyl group” and the “substituted alkenyl group” listed here are only examples, and the "substituted alkenyl group” described in the present specification includes the specific example group G4B.
  • Unsubstituted alkenyl group (specific example group G4A): Vinyl group, Allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
  • Substituent alkenyl group (specific example group G4B): 1,3-Butandienyl group, 1-Methyl vinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-Methylallyl group and 1,2-dimethylallyl group.
  • alkynyl groups and “substituted alkynyl groups”.
  • the "substituted alkynyl group” means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include a group in which one or more hydrogen atoms are replaced with a substituent in the following "unsubstituted alkynyl group” (specific example group G5A).
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in the present specification include the following unsubstituted cycloalkyl group (specific example group G6A) and a substituted cycloalkyl group (specific example group G6A). Specific example group G6B) and the like can be mentioned.
  • the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is the “unsubstituted cycloalkyl group", and the substituted cycloalkyl group is the "substituted or unsubstituted cycloalkyl group". Refers to the case where the "cycloalkyl group” is a "substituted cycloalkyl group”.
  • the term “cycloalkyl group” is simply referred to as "unsubstituted cycloalkyl group” and "substituted cycloalkyl group”. Including both.
  • the "substituted cycloalkyl group” means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include a group in which one or more hydrogen atoms are replaced with a substituent in the following "unsubstituted cycloalkyl group” (specific example group G6A), and a substituted cycloalkyl group. Examples of (Specific example group G6B) can be mentioned.
  • cycloalkyl group (Specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • Substituent cycloalkyl group (Specific example group G6B): 4-Methylcyclohexyl group.
  • G7 of the groups represented by ⁇ Si (R 901 ) (R 902 ) (R 903 ) described in the present specification include. -Si (G1) (G1) (G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si (G2) (G2) (G2), -Si (G3) (G3), and -Si (G6) (G6) (G6) (G6) Can be mentioned.
  • G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • -A plurality of G1s in Si (G1) (G1) (G1) are the same as or different from each other.
  • -A plurality of G2s in Si (G1) (G2) (G2) are the same as or different from each other.
  • -A plurality of G1s in Si (G1) (G1) (G2) are the same as or different from each other.
  • -A plurality of G2s in Si (G2) (G2) (G2) are the same as or different from each other.
  • -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
  • -A plurality of G6s in Si (G6) (G6) (G6) are the same as or different from each other.
  • G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • G10 -N (G1) (G1), -N (G2) (G2), -N (G1) (G2), -N (G3) (G3) and -N (G6) (G6)
  • G1 is the "substituted or unsubstituted aryl group” described in the specific example group G1.
  • G2 is the "substituted or unsubstituted heterocyclic group” described in the specific example group G2.
  • G3 is the "substituted or unsubstituted alkyl group” described in the specific example group G3.
  • G6 is the "substituted or unsubstituted cycloalkyl group” described in the specific example group G6.
  • a plurality of G1s in -N (G1) (G1) are the same as or different from each other.
  • -A plurality of G2s in N (G2) (G2) are the same as or different from each other.
  • -A plurality of G3s in N (G3) (G3) are the same as or different from each other.
  • a plurality of G6s in -N (G6) (G6) are the same as or different from each other.
  • Halogen atom Specific examples of the "halogen atom” described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
  • the "unsubstituted fluoroalkyl group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • “Substituent fluoroalkyl group” means a group in which one or more hydrogen atoms of a “fluoroalkyl group” are replaced with a substituent.
  • the “substituted fluoroalkyl group” described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituent fluoroalkyl group” are further replaced with a substituent.
  • groups in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced by the substituent.
  • Specific examples of the "unsubstituted fluoroalkyl group” include an example of a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
  • the "unsubstituted haloalkyl group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • the "substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group” described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted haloalkyl group” are further replaced with a substituent, and a "substituent".
  • haloalkyl group groups in which one or more hydrogen atoms of the substituents in the "haloalkyl group” are further replaced by the substituents.
  • substituents in the "haloalkyl group” include an example of a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • the haloalkyl group may be referred to as an alkyl halide group.
  • a specific example of the "substituted or unsubstituted alkoxy group” described in the present specification is a group represented by —O (G3), where G3 is the “substituted or unsubstituted” group described in the specific example group G3. It is an unsubstituted alkyl group.
  • the "unsubstituted alkoxy group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted alkylthio group” described in the present specification is a group represented by ⁇ S (G3), where G3 is the “substituted or substituted” described in the specific example group G3. It is an unsubstituted alkyl group.
  • the "unsubstituted alkylthio group” has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “substitution” described in the specific example group G1. Alternatively, it is an unsubstituted aryl group.
  • the ring-forming carbon number of the "unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise stated herein.
  • -"Substituted or unsubstituted arylthio group A specific example of the "substituted or unsubstituted arylthio group” described in the present specification is a group represented by -S (G1), where G1 is the "substituted or substituted arylthio group” described in the specific example group G1. It is an unsubstituted aryl group. " The ring-forming carbon number of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise stated herein.
  • -"Substituted or unsubstituted trialkylsilyl group Specific examples of the "trialkylsilyl group” described in the present specification are groups represented by ⁇ Si (G3) (G3) (G3), where G3 is described in the specific example group G3. It is a "substituted or unsubstituted alkyl group”. -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
  • the carbon number of each alkyl group of the "trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.
  • the "unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group” is unless otherwise specified herein. , 7 to 50, preferably 7 to 30, and more preferably 7 to 18.
  • Specific examples of the "substituted or unsubstituted aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, and an ⁇ .
  • -Naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group and the like.
  • substituted or unsubstituted aryl groups described herein are preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-unless otherwise described herein.
  • the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzoimidazolyl group, or a phenyl group, unless otherwise described herein.
  • Nantrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , Dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-Phenyl) Carbazolyl Group ((9-Phenyl) Carbazole-1-yl Group, (9-Phenyl) Carbazole-2-yl Group, (9-Phenyl) Carbazole-3-yl Group, or (9-Phenyl) Carbazole Group,
  • carbazolyl group is specifically one of the following groups unless otherwise described in the present specification.
  • the (9-phenyl) carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.
  • dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise described in the present specification.
  • substituted or unsubstituted alkyl groups described herein are preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-, unless otherwise stated herein. It is a butyl group or the like.
  • the "substituted or unsubstituted arylene group” described herein is derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group” 2 It is the basis of the value.
  • the "substituted or unsubstituted arylene group” (specific example group G12), by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in the specific example group G1. Examples include the induced divalent group.
  • the "substituted or unsubstituted divalent heterocyclic group" described in the present specification shall exclude one hydrogen atom on the heterocycle from the above "substituted or unsubstituted heterocyclic group". It is a divalent group derived by.
  • specific example group G13 of the "substituted or unsubstituted divalent heterocyclic group"
  • Examples thereof include a divalent group derived by removing an atom.
  • the "substituted or unsubstituted alkylene group” described herein is derived by removing one hydrogen atom on the alkyl chain from the above "substituted or unsubstituted alkyl group” 2 It is the basis of the value.
  • the "substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group" described in the specific example group G3. Examples include the induced divalent group.
  • the substituted or unsubstituted arylene group described in the present specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise described in the present specification.
  • Q 1 ⁇ Q 10 are each independently a hydrogen atom or a substituent.
  • the formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a binding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group according to any of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise described herein. Is.
  • Q 1 ⁇ Q 9 are independently a hydrogen atom or a substituent.
  • the set of two adjacent sets is one set. Is a pair of R 921 and R 922 , a pair of R 922 and R 923 , a pair of R 923 and R 924 , a pair of R 924 and R 930 , a pair of R 930 and R 925, and a pair of R 925 .
  • the above-mentioned "one or more sets” means that two or more sets of two or more adjacent sets may form a ring at the same time.
  • R 921 and R 922 are coupled to each other to form ring Q A
  • R 925 and R 926 are coupled to each other to form ring Q B
  • the above general formula (TEMP-103) is used.
  • the anthracene compound represented is represented by the following general formula (TEMP-104).
  • the formed "monocycle” or “condensed ring” may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when “one set of two adjacent sets” forms a “monocycle” or “condensed ring”, the “monocycle” or “condensed ring” is a saturated ring or a saturated ring.
  • An unsaturated ring can be formed.
  • the general formula (TEMP-104) Ring Q A and ring Q B formed in respectively the “monocyclic” or “fused rings”. Further, the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “condensed rings”.
  • the ring Q A and the ring Q C of the general formula (TEMP-105) are condensed rings by condensing the ring Q A and the ring Q C. If the ring Q A of the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. If the ring Q A of the general formula (TMEP-104) is a naphthalene ring, the ring Q A is a fused ring.
  • the "unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle.
  • saturated ring is meant an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
  • aromatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G1 is terminated by a hydrogen atom.
  • aromatic heterocycle include a structure in which the aromatic heterocyclic group given as a specific example in the specific example group G2 is terminated by a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom.
  • Forming a ring means forming a ring with only a plurality of atoms in the mother skeleton, or with a plurality of atoms in the mother skeleton and one or more arbitrary elements.
  • the ring Q A where the R 921 and R 922 are bonded formed with each other, the carbon atoms of the anthracene skeleton R 921 are attached, anthracene R 922 are bonded It means a ring formed by a carbon atom of a skeleton and one or more arbitrary elements.
  • the carbon atom of the anthracene skeleton and R 922 are attached, four carbon atoms
  • the ring formed by R 921 and R 922 is a benzene ring.
  • arbitrary element is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise described in the present specification.
  • the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later.
  • the ring formed is a heterocycle.
  • the number of "one or more arbitrary elements" constituting the monocycle or condensed ring is preferably 2 or more and 15 or less, and more preferably 3 or more and 12 or less. , More preferably 3 or more and 5 or less.
  • the "monocycle” and the “condensed ring” are preferably “monocycles”.
  • the "saturated ring” and the “unsaturated ring” are preferably “unsaturated rings”.
  • the "monocycle” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more pairs of two or more adjacent pairs are bonded to each other to form a plurality of atoms in the mother skeleton and one or more 15 elements. It forms a substituted or unsubstituted "unsaturated ring” consisting of at least one element selected from the group consisting of the following carbon element, nitrogen element, oxygen element, and sulfur element.
  • the substituent is, for example, an "arbitrary substituent” described later.
  • Specific examples of the substituent when the above-mentioned “monocycle” or “condensed ring” has a substituent are the substituents described in the above-mentioned “Substituents described in the present specification” section.
  • the substituent is, for example, an "arbitrary substituent” described later.
  • substituents when the above-mentioned "monocycle” or “condensed ring” has a substituent are the substituents described in the above-mentioned “Substituents described in the present specification” section.
  • the above is the case where "one or more pairs of two or more adjacent pairs are combined with each other to form a substituted or unsubstituted monocycle" and "one or more pairs of two or more adjacent pairs".
  • Unsubstituted alkyl groups with 1 to 50 carbon atoms An unsubstituted alkenyl group having 2 to 50 carbon atoms, An unsubstituted alkynyl group having 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, It is a group selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. If there are two or more R 901s , the two or more R 901s are the same or different from each other. If there are two or more R 902s , the two or more R 902s are the same or different from each other.
  • the two or more R 903s are the same or different from each other. If there are two or more R 904s , the two or more R 904s are the same or different from each other. If there are two or more R 905s , the two or more R 905s are the same or different from each other. If there are two or more R- 906s , the two or more R- 906s are the same or different from each other. When two or more R 907s are present, the two or more R 907s are the same as or different from each other.
  • the substituent in the case of "substituent or unsubstituted" is Alkyl groups with 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring-forming carbon atoms and a heterocyclic group having 5 to 50 ring-forming atoms.
  • the substituent in the case of "substituent or unsubstituted" is Alkyl groups with 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring-forming carbon atoms and a heterocyclic group having 5 to 18 ring-forming atoms.
  • any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5 It forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.
  • any substituent may further have a substituent.
  • the substituent further possessed by the arbitrary substituent is the same as that of the above-mentioned arbitrary substituent.
  • the numerical range represented by using “AA to BB” has the numerical value AA described before “AA to BB” as the lower limit value and the numerical value BB described after “AA to BB”. Means the range including as the upper limit value.
  • the organic EL element is an organic EL element having a cathode, an anode, and a light emitting layer arranged between the cathode and the anode, and the light emitting layer is a first host. It is characterized by including a material, a second host material, and a dopant material.
  • the organic EL device according to one aspect of the present invention exhibits high device performance by having the above configuration. Specifically, it is possible to provide an organic EL device having a low drive voltage and high external quantum efficiency. Details of each material will be described later.
  • the organic EL element 1 includes a substrate 2, an anode 3, a light emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light emitting layer 5, and a light emitting layer 5. It has an organic layer 6 between it and the cathode 10.
  • the first host material, the second host material, and the dopant material are contained in the light emitting layer 5 between the anode 3 and the cathode 10.
  • Each compound contained in the light emitting layer 5 may be one kind alone or two or more kinds.
  • the organic EL element 1 may include a light emitting layer in addition to the light emitting layer 5, but in one aspect of the present invention, usually, a first host material and a first host material are contained in a single light emitting layer (light emitting layer 5). A second host material and a dopant material are included.
  • the first host material is a compound represented by the following formula (1). However, the first host material is a compound different from the second host material described later.
  • R 1A to R 8A are independent of each other. Hydrogen atom, Substituent R, or a group represented by the following formula (1A).
  • the substituent R is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms,
  • L 1A is independent of each other Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1A is independent of each other A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other.
  • Any hydrogen atom contained in the compound represented by the formula (1) may be a deuterium atom.
  • the compound represented by the formula (1) is a compound represented by the following formula (1-1).
  • R 1A , R 3A to R 8A , L 1A and Ar 1A are as defined in the above formula (1).
  • the compound represented by the formula (1) is a compound represented by the following formula (1-11), formula (1-12) or formula (1-13).
  • R 1A , R 3A to R 8A , L 1A and Ar 1A are as defined in the above formula (1). .
  • the compound represented by the formula (1) is a compound represented by the following formula (1-2).
  • the compound represented by the formula (1) is a compound represented by the following formula (1-21), formula (1-22) or formula (1-23).
  • L 1A is a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 14 carbon atoms, respectively.
  • L 1A is a single-bonded, substituted or unsubstituted phenylene group, or substituted or unsubstituted naphthylene group, respectively.
  • Ar 1A is an independently substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • Ar 1A is independently selected from the groups represented by any of the following formulas (a1) to (a4).
  • R 21 is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming mono
  • R 901 to R 907 are as defined by the above equation (1).
  • m1 is an integer from 0 to 4.
  • m2 is an integer from 0 to 5.
  • m3 is an integer from 0 to 7.
  • the plurality of R 21s may be the same as each other or may be different from each other.
  • the plurality of adjacent R 21s are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )
  • R 1A ⁇ R 8A may be a deuterium atom, all of R 1A ⁇ R 8A may be a deuterium atom.
  • the compound having the same structure as the compound represented by the formula (1) in the light emitting layer and the compound represented by the formula (1) except that it contains only a light hydrogen atom as a hydrogen atom ( Hereinafter, the content ratio of the latter to the total with the "light hydrogen compound") is 99 mol% or less. The content ratio of the light hydrogen compound is confirmed by mass spectrometry.
  • the compound represented by the formula (1) can be synthesized by using a known alternative reaction or raw material suitable for the target product.
  • the second host material used in one embodiment of the present invention is a compound represented by the following formula (2).
  • X 11B is an oxygen atom or a sulfur atom.
  • Two or more adjacent pairs of R 14B to R 17B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.
  • Two or more adjacent pairs of R 11B to R 13B combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 11B to R 17B which do not form the substituted or unsaturated saturated or unsaturated ring, are independently of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 1B to R 8B are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic
  • L 1B and L 2B are independent of each other. Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1B is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are as defined by the above equation (1).
  • Any hydrogen atom contained in the compound represented by the formula (2) may be a deuterium atom.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-1), formula (2-2) or formula (2-3).
  • R 1B to R 8B , R 11B to R 13B , L 1B , L 2B , X 11B and Ar 1B are as defined in the above formula (2).
  • R 14B to R 21B are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • L 1B and L 2B are independently single-bonded, substituted or unsubstituted ring-forming arylene groups having 6 to 14 carbon atoms, respectively.
  • L 1B and L 2B are independently single-bonded, substituted or unsubstituted phenylene groups, or substituted or unsubstituted naphthylene groups, respectively.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-11), formula (2-12) or formula (2-13).
  • R 1B to R 8B , R 11B to R 13B , X 11B and Ar 1B are as defined in the above formula (2).
  • R 14B to R 21B are independent of each other.
  • Ar 1B is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • Ar 1B is selected from the groups represented by any of the following formulas (a1) to (a4).
  • R 21 is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming mono
  • R 901 to R 907 are as defined by the above equation (1).
  • m1 is an integer from 0 to 4.
  • m2 is an integer from 0 to 5.
  • m3 is an integer from 0 to 7.
  • the plurality of R 21s may be the same as each other or may be different from each other.
  • the plurality of adjacent R 21s are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )
  • X 11B is an oxygen atom.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-21), formula (2-22) or formula (2-23).
  • Ar 1B is as defined by the above formula (2).
  • the compound represented by the formula (2) can be synthesized by following the synthesis method described in Examples and using a known alternative reaction or raw material suitable for the target product.
  • the compound represented by the following formula (3-1) and the compound represented by the following formula (3-2) are novel compounds.
  • the naphthobenzofuran binds to the anthracene unit at a specific substitution position, so that the hole injection property is improved.
  • the carrier balance is improved and deterioration at the interface of the light emitting layer on the hole transport layer side is suppressed, so that the life of the device is expected to be extended.
  • It can be used as a second host material used in the light emitting layer of the organic EL device of the embodiment. It can also be used as a single host material for the light emitting layer.
  • the life of the organic EL device can be improved.
  • the rate of deuteration may vary.
  • the rate of deuteration is unlikely to vary.
  • the compound represented by the following formula (3-1) and the compound represented by the following formula (3-2) have a higher deuteration rate than the case where a compound in which all hydrogen atoms are deuterated is used. Since it is uniform, the variation in the quality of the device produced by using the compound is reduced, and the yield of device manufacturing can be expected to be improved.
  • X 11C is an oxygen atom or a sulfur atom.
  • L 1C and L 2C are independent of each other. Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • the hydrogen atom possessed by L 1C which is not a single bond, may be a deuterium atom.
  • Two or more adjacent pairs of R 11C to R 13C combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring.
  • R 1C to R 8C , R 14C , R 15C , and R 18C to R 21C , and R 11C to R 13C which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different.
  • R 1C to R 8C , R 14C , R 15C , and R 18C to R 21C , and R 11C to R 13C that do not form the substituted or unsubstituted saturated or unsaturated ring are hydrogen atoms, this is the case.
  • Hydrogen atom is not deuterium atom;
  • the hydrogen atoms contained in R 1C to R 8C, R 14C , R 15C , and R 18C to R 21C , which are not hydrogen atoms , and R 11C to R 13C, which do not form the substituted or unsubstituted saturated or unsaturated ring, are Not a deuterium atom;
  • R 1C to R 8C , R 14C , R 15C , and R 18C to R 21C which are not hydrogen atoms , and R 11C to R 13C, which do not form the substituted or unsubstituted saturated or unsaturated ring, are optional substituents.
  • the hydrogen atom of the optional substituent is not a deuterium atom;
  • Hydrogen atom ring has a R 11C ⁇ R 13C are bonded is formed of the substituted or unsubstituted, saturated or unsaturated with one another is not a deuterium; and wherein the R 11C ⁇ R 13C are bonded is formed to each other
  • the hydrogen atom of the optional substituent is not a deuterium atom.
  • X 11C in the formula (3-1) is an oxygen atom.
  • L 1C and L 2C in the formula (3-1) are each independently a single bond, a phenylene group or a naphthylene group.
  • L 2C in the formula (3-1) is a single bond.
  • R 1C to R 8C in the above formula (3-1) are hydrogen atoms.
  • R 11C to R 15C and R 18C to R 21C in the above formula (3-1) are hydrogen atoms.
  • a novel compound according to another aspect of the present invention is a compound represented by the following formula (3-2).
  • X 11C is an oxygen atom or a sulfur atom.
  • L 1C is Single bond, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • Ar 1C is A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • at least one of the hydrogen atoms of the group -L 1C- Ar 1C is a deuterium atom.
  • R 11C to R 13C Two or more adjacent pairs of R 11C to R 13C combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 1C to R 8C , R 14C , and R 17C to R 21C , and R 11C to R 13C , which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different.
  • R 1C to R 8C , R 14C , and R 17C to R 21C , and R 11C to R 13C which do not form the substituted or unsaturated saturated or unsaturated ring are hydrogen atoms
  • the hydrogen atom is the hydrogen atom.
  • R 11C to R 13C which do not form a substituted or unsubstituted saturated or unsaturated ring, are deuterium atoms.
  • R 1C to R 8C , R 14C , and R 17C to R 21C which are not hydrogen atoms
  • R 11C to R 13C which do not form the substituted or unsubstituted saturated or unsaturated ring, have arbitrary substituents.
  • the hydrogen atom of the arbitrary substituent is not a deuterium atom; Hydrogen atom ring has a R 11C ⁇ R 13C are bonded is formed of the substituted or unsubstituted, saturated or unsaturated with one another is not a deuterium; and wherein the R 11C ⁇ R 13C are bonded is formed to each other When the substituted or unsubstituted saturated or unsaturated ring has an arbitrary substituent, the hydrogen atom of the optional substituent is not a deuterium atom.
  • the compound represented by the above formula (3-2) is a compound represented by the following formula (3-2-1).
  • L1C is a single-bonded or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms. In one embodiment, in the formula (3-2-1), L1C is a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group. In one embodiment, in the above formula (3-2), X 11C is an oxygen atom.
  • the compound represented by the above formula (3-2) is a compound represented by the following formula (3-2-2).
  • Ar 1C is as defined by the above formula (3-2).
  • Ar 1C in the formula (3-2) is -C 6 D 5 group.
  • the compound represented by the formula (3-1) and the compound represented by the formula (3-2) are prepared by following the synthesis method described in the synthesis example and using a known alternative reaction or raw material suitable for the desired product. , Compounds within the scope of the present invention can be synthesized.
  • the dopant material used in the light emitting layer of the organic EL element of one aspect of the present invention is a compound represented by the following formula (11), a compound represented by the following formula (21), and a compound represented by the following formula (31).
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are as defined by the above equation (1).
  • Ar 101 and Ar 102 are independent of each other.
  • L 101 to L 103 are independent of each other. Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms.
  • R 101 to R 110 are groups represented by formula (12).
  • the compound represented by the formula (11) is represented by the following formula (13).
  • R 111 to R 118 are the same as R 101 to R 110 which are not the monovalent groups represented by the formula (12) in the formula (11).
  • Ar 101 , Ar 102. , L 101 , L 102 and L 103 are as defined in the above equation (12).)
  • L 101 is preferably a single bond
  • L 102 and L 103 are preferably a single bond.
  • the compound represented by the formula (11) is represented by the following formula (14) or (15).
  • R 111 to R 118 are as defined by the above formula (13).
  • Ar 101 , Ar 102 , L 102 and L 103 are as defined by the above formula (12). .
  • R 111 to R 118 are as defined by the above formula (13).
  • Ar 101 and Ar 102 are as defined by the above formula (12).)
  • Ar 101 and Ar 102 are a group represented by the following formula (16).
  • X 101 represents an oxygen atom or a sulfur atom.
  • R 121 to R 127 two or more adjacent pairs may combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring of. R 121 to R 127 , which do not form the substituted or unsaturated saturated or unsaturated ring, are independently of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • X 101 is preferably an oxygen atom.
  • At least one of R 121 to R 127 Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, It is preferably an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
  • Ar 101 is a group represented by the formula (16) and Ar 102 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. ..
  • the compound represented by the formula (11) is represented by the following formula (17).
  • R 111 to R 118 are as defined by the above formula (13).
  • R 121 to R 127 are as defined by the above formula (16).
  • R 131 to R 135 are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • n21 and n22 are independently integers from 0 to 4.
  • Ra a to R c which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • the "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group”.
  • the "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains two carbon atoms on the condensed dicyclic structure in the center of the formula (21) as ring-forming atoms.
  • Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms” include a compound in which a hydrogen atom is introduced into the "aryl group” described in the specific example group G1.
  • the "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group”.
  • the "heterocycle” of the A1 ring and the A2 ring contains two carbon atoms on the condensed bicyclic structure in the center of the formula (21) as ring-forming atoms.
  • Specific examples of the "heterocyclic ring having 5 to 50 substituted or unsubstituted ring-forming atoms” include a compound in which a hydrogen atom is introduced into the "heterocyclic group" described in the specific example group G2.
  • R b is attached to either a carbon atom forming an aromatic hydrocarbon ring of the A1 ring or an atom forming a heterocycle of the A1 ring.
  • Rc is attached to either the carbon atom forming the aromatic hydrocarbon ring of the A2 ring or the atom forming the heterocycle of the A2 ring.
  • R a to R c at least one (preferably two) is preferably a group represented by the following formula (21a).
  • -L 201- Ar 201 (21a) (In equation (21a) L 201 is Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms.
  • Ar 201 Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, A substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms, or a group represented by the following formula (21b).
  • L 211 and L 212 are independent of each other. Single bond, It is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms.
  • Ar 211 and Ar 212 combine 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.
  • Ar 211 and Ar 212 which do not form a substituted or unsaturated saturated or unsaturated ring, are independent of each other. Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, A substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms. )
  • the compound represented by the formula (21) is represented by the following formula (22).
  • (In equation (22) Two or more adjacent pairs of R 201 to R 211 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring of. R 201 to R 211 , which do not form the substituted or unsaturated saturated or unsaturated ring, are independently of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • R 201 to R 211 at least one (preferably two) is preferably a group represented by the above formula (21a).
  • R 204 and R 211 are groups represented by the above formula (21a).
  • the compound represented by the formula (21) is a compound in which the structure represented by the following formula (21-1) or (21-2) is bound to the A1 ring.
  • the compound represented by the formula (22) is a compound in which the structure represented by the following formula (21-1) or (21-2) is bonded to the ring to which R 204 to R 207 are bonded.
  • the two bonds * are independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring of the A1 ring of the formula (21) or the ring-forming atom of the heterocycle. Alternatively, it is combined with any of R 204 to R 207 of the formula (22).
  • the three bonds * of the formula (21-2) are independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring of the A1 ring of the formula (21) or the ring-forming atom of the heterocycle, or the formula (21-2).
  • Two or more adjacent pairs of R 221 to R 227 and R 231 to R 239 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or absent. Does not form a saturated or unsaturated ring of substitutions.
  • R 221 to R 227 and R 231 to R 239 which do not form the substituted or unsubstituted saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • the compound represented by the formula (21) is a compound represented by the following formula (21-3), formula (21-4) or formula (21-5).
  • the A1 ring is as defined by the equation (21).
  • R 2401 to R 2407 are the same as R 221 to R 227 of the formulas (21-1) and (21-2).
  • R 2410 to R 2417 are the same as R 201 to R 211 of the equation (22). The two R 2417s may be the same or different from each other. )
  • the substituted or unsubstituted ring-forming ring of the A1 ring of the formula (21-5) is an aromatic hydrocarbon ring having 6 to 50 carbon atoms, which is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene. It is a ring.
  • the substituted or unsubstituted ring-forming heterocycle of the A1 ring of the formula (21-5) has a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted ring. Alternatively, it is an unsubstituted dibenzothiophene ring.
  • the compound represented by the formula (21) or the formula (22) is selected from the group consisting of the compounds represented by the following formulas (21-6-1) to (21-6-7). .. (In equations (21-6-1) to (21-6-7), R 2421 to R 2427 are the same as R 221 to R 227 of the formulas (21-1) and (21-2). R 2430 to R 2437 and R 2441 to R 2444 are the same as R 201 to R 211 of the formula (22). X is O, NR 901 , or C (R 902 ) (R 903 ). R 901 to R 903 are as defined by the above equation (1). )
  • the compound represented by the formula (22) has two or more adjacent pairs of R 201 to R 211 bonded to each other to be substituted or unsubstituted saturated or unsaturated. Form a ring.
  • the embodiment will be described in detail as the following formula (25).
  • the two or more rings formed by R 251 to R 261 may be the same or different.
  • R 251 to R 261 that do not form the substituted or unsaturated saturated or unsaturated ring are independent of each other.
  • R n and R n + 1 (n represents an integer chosen from 251, 252, 254 to 256, and 258 to 260) are coupled to each other, and two rings to which R n and R n + 1 are coupled. Forming Together with carbon atoms, it forms a substituted or unsubstituted saturated or unsaturated ring.
  • the ring is preferably composed of an atom selected from C atom, O atom, S atom and N atom, and the number of atoms is preferably 3 to 7, and more preferably 5 or 6.
  • the number of the above ring structures in the compound represented by the formula (25) is, for example, 2, 3, or 4.
  • the two or more ring structures may be present on the same benzene ring on the matrix of the formula (25), respectively, or may be present on different benzene rings.
  • one ring structure may be present for each of the three benzene rings of the formula (25).
  • Examples of the ring structure in the compound represented by the formula (25) include structures represented by the following formulas (251) to (260). (In equations (251) to (257), * 1 and * 2, * 3 and * 4, * 5 and * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13
  • * 14 represents the two ring-forming carbon atoms to which R n and R n + 1 are bonded, and the ring-forming carbon atoms to which R n is bonded are * 1 and * 2, * 3 and * 4, and * 5. It may be either of the two ring-forming carbon atoms represented by * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13 and * 14.
  • X 2501 is C (R 2512 ) (R 2513 ), NR 2514 , O or S. Two or more adjacent pairs of R 2501 to R 2506 and R 2512 to R 2513 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or absent. Does not form a saturated or unsaturated ring of substitutions.
  • R 2501 to R 2514 which do not form a substituted or unsubstituted saturated or unsaturated ring, are the same as R 251 to R 261 described above. )
  • * 1 and * 2, and * 3 and * 4 represent the two ring-forming carbon atoms to which R n and R n + 1 are bonded, and R n is bonded.
  • the ring-forming carbon atom may be either * 1 and * 2, or the two ring-forming carbon atoms represented by * 3 and * 4.
  • X 2501 is C (R 2512 ) (R 2513 ), NR 2514 , O or S.
  • Two or more adjacent pairs of R 2515 to R 2525 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring of.
  • R 2515 to R 2521 and R 2522 to R 2525 which do not form a substituted or unsubstituted saturated or unsaturated ring, are the same as those of R 251 to R 261.
  • R 252 , R 254 , R 255 , R 260 and R 261 is a ring. It is preferable that the group does not form a structure.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -N (R 906 ) (R 907 ), Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, A substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms, or a group selected from the following group.
  • R d are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group
  • X is C (R 901 ) (R 902 ), NR 903 , O or S.
  • R 901 to R 907 are as defined by the above equation (1).
  • p1 is an integer of 0 to 5 independently, p2 is an integer of 0 to 4, p3 is an integer of 0 to 3, and p4 is an integer of 0 to 7.
  • the compound represented by the formula (25) is represented by any of the following formulas (25-1) to (25-6).
  • rings di to i are independently substituted or unsubstituted saturated or unsaturated rings.
  • R 251 to R 261 are the above-mentioned formulas (25). ) Is the same.
  • the compound represented by the formula (25) is represented by any of the following formulas (25-7) to (25-12).
  • rings d to f, k, and j are independently substituted or unsubstituted saturated or unsaturated rings.
  • R 251 to R 261 are It is the same as the above formula (25).
  • the compound represented by the formula (25) is represented by any of the following formulas (25-13) to (25-21).
  • rings d to k are independently substituted or unsubstituted saturated or unsaturated rings.
  • R 251 to R 261 are the above-mentioned formulas (25). ) Is the same.
  • substituents when the ring g or h further has a substituent include, for example.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or groups represented by the above formulas (261), (263) or (264) can be mentioned.
  • the compound represented by the formula (25) is represented by any of the following formulas (25-22) to (25-25).
  • X 250 are independently C (R 901 ) (R 902 ), NR 903 , O or S.
  • R 251 to R 261 and R 271 to. R 278 is the same as R 251 to R 261 of the above formula (25).
  • R 901 to R 903 are as defined by the above formula (1).
  • the compound represented by the formula (25) is represented by the following formula (25-26).
  • X 250 is C (R 901 ) (R 902 ), NR 903 , O or S.
  • ⁇ R 282 is the same as R 251 ⁇ R 261 of the above formula (25).
  • R 901 ⁇ R 903 are as defined by the above formula (1).
  • the compound represented by the formula (31) will be described.
  • the compound represented by the formula (31) is a compound corresponding to the compound represented by the above-mentioned formula (21-3).
  • (In equation (31) Two or more adjacent pairs of R 301 to R 307 and R 311 to R 317 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or unsubstituted. Does not form a saturated or unsaturated ring of.
  • R 301 to R 307 and R 311 to R 317 which do not form the substituted or unsubstituted saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 321 and R 322 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic
  • One set of two or more adjacent to each other among R 301 to R 307 and R 311 to R 317 is, for example, R 301 and R 302 , R 302 and R 303 , R 303 and R 304 , R 305 and R 306. , R 306 and R 307 , R 301 and R 302 and R 303 and the like.
  • At least one, preferably two , of R 301 to R 307 and R 311 to R 317 are groups represented by -N (R 906 ) (R 907).
  • R 301 to R 307 and R 311 to R 317 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming atom. It is a monovalent heterocyclic group of the number 5 to 50.
  • the compound represented by the formula (31) is a compound represented by the following formula (32).
  • (In equation (32) Two or more adjacent pairs of R 331 to R 334 and R 341 to R 344 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or unsubstituted. Does not form a saturated or unsaturated ring of. R 331 to R 334 , R 341 to R 344 , and R 351 and R 352 , which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 361 to R 364 are independent of each other.
  • the compound represented by the formula (31) is a compound represented by the following formula (33).
  • R 351 and R 352 and R 361 to R 364 are as defined in the above formula (32).
  • the compound represented by the formula (31) is a compound represented by the following formula (34) or (35).
  • R 361 to R 364 are as defined by the above equation (32).
  • Two or more adjacent pairs of R 371 to R 377 and R 380 to R 386 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or unsubstituted. Does not form a saturated or unsaturated ring of.
  • R 371 to R 377 and R 380 to R 386 , and R 387 which do not form the substituted or unsubstituted saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • the two R 387s may be the same or different from each other.
  • the compound represented by the formula (31) is a compound represented by the following formula (34-2) or (35-2).
  • R 361 to R 364 , R 375 to R 377, and R 384 to R 387 are as defined in the formulas (34) and (35).
  • R 361 to R 364 in formulas (32), (33), (34), (35), (34-2), and (35-2) are independently substituted or unsubstituted, respectively. It is an aryl group (preferably a phenyl group) having 6 to 50 carbon atoms.
  • R 387 are independently hydrogen atoms or substituted or unsubstituted aryl groups having 6 to 50 carbon atoms (preferably phenyl groups).
  • the compound represented by the formula (31) is a compound represented by the following formula (32-11), a compound represented by the following formula (34-11), and a compound represented by the following formula (35-11).
  • One or more compounds selected from the group consisting of the represented compounds. (In equations (32-11), (34-11) and (35-11), Two or more adjacent pairs of R 3301 to R 3307 and R 3311 to R 3317 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or unsubstituted. Does not form a saturated or unsaturated ring of.
  • R 3301 to R 3307 and R 3311 to R 3317 , and R 3331 which do not form the substituted or unsubstituted saturated or unsaturated ring, are independently hydrogen atoms and substituted or unsubstituted ring-forming carbon atoms 6 to 3, respectively. It is an aryl group of 20, or a monovalent heterocyclic group having 5 to 20 substituted or unsubstituted ring-forming atoms.
  • the two R 3331s may be the same or different from each other.
  • R 3321 to R 3324 are independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms or monovalent heterocyclic groups having 5 to 20 substituted or unsubstituted ring-forming atoms.
  • the compound is one or more selected from the group consisting of a compound represented by the following formula (32-12), a compound represented by the following formula (34-12), and a compound represented by the following formula (35-12). It is a compound of. (In formulas (32-12), (34-12) and (35-12), R 3321 to R 3324 and R 3331 are the above-mentioned formulas (32-11), (34-11) and (35-11). As defined in.)
  • R 3321 to R 3324 are Each is independently a substituted or unsubstituted phenyl group.
  • the substituent is selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 ring-forming carbon atoms, and a monovalent heterocyclic group having 5 to 20 ring-forming atoms.
  • R 3321 to R 3324 are Each is an independently substituted or unsubstituted phenyl group, and the two R 3331s are hydrogen atoms, respectively.
  • R 3321 to R 3324 are Independently, each is a substituted or unsubstituted phenyl group, the two R 3331s are hydrogen atoms, respectively, and the substituent in the case of "substituent or unsubstituted" is an alkyl group having 1 to 20 carbon atoms and a ring. It is selected from the group consisting of an aryl group having 6 to 20 carbon atoms and a monovalent heterocyclic group having 5 to 20 ring-forming atoms.
  • R 3321 to R 3324 are Each independently is a substituted or unsubstituted phenyl group, the two R 3331s are hydrogen atoms, respectively, and the substituent in the case of "substituent or unsubstituted" is an alkyl group having 1 to 5 carbon atoms. ..
  • two or more adjacent sets of R 301 to R 307 and R 311 to R 317 are bonded to each other and are substituted or unsaturated. Form a saturated or unsaturated ring.
  • the compound represented by the formula (31) is one or more compounds selected from the group consisting of the compounds represented by any of the following formulas (36-1) to (36-6). .. (In equations (36-1) to (36-6), Two or more adjacent pairs of R 3605 to R 3607 , R 3615 to R 3617 and R 3631 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or said above. Does not form a ring. Two or more adjacent pairs of R 3601 to R 3604 , R 3611 to R 3614 and R 3621 to R 3628 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring. Or do not form the ring.
  • R 3601 to R 3607 , R 3611 to R 3617 , R 3621 to R 3628, and R 3631, which do not form the ring, are independent of each other. Hydrogen atom, halogen atom, cyano group, nitro group, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), A substituted or unsubstituted ring-forming aryl group having 6 to 50
  • R 901 to R 907 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. When two or more R 901 to R 907 are present, each of the two or more R 901 to R 907 may be the same or different.
  • X 1 is selected from O, S and N (R 3641), 2 two X 1 may be identical to one another or may be different.
  • R 3641 combines with one or more selected from the group consisting of R 3601 to R 3604 , R 3611 to R 3614 , R 3624 and R 3628 to form a substituted or unsaturated saturated or unsaturated ring. Or do not form the ring.
  • R3641 that does not form the ring is a hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • the compound represented by the formula (31) is a compound represented by the formula (36-1) or the formula (36-2), and in one embodiment, the compound represented by the formula (36-1). It is a compound to be used.
  • the two R 3631s are phenyl groups.
  • X 1 is N (R 3461 ).
  • R3641 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • the compound represented by the formula (31) is a compound represented by the following formula (36-1-1).
  • formula (36-1-1) two or more adjacent ones of R 3001 , R 3002 , R 3005 to R 3007 , R 3010 , R 3011 , R 3014 to R 3016 , and R 3031 to R 3034. Pairs or more combine 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 a is independently selected from O, S and N (R 3035).
  • R 3035 couples with R 3031 to form a substituted or unsubstituted saturated or unsaturated ring, or does not form the ring.
  • R 3001 , R 3002 , R 3005 to R 3007 , R 3010 , R 3011 , R 3014 to R 3016 , and R 3031 to R 3034 , and R 3021 which do not form the substituted or unsaturated saturated or unsaturated ring.
  • R 3022 are independent of each other Hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. )
  • formulas (31)-(35), (34-2), (35-2), (32-11), (34-11), (35-11), (32-12), In (34-12), (35-12), (36-1) to (36-6) and (36-1-1), the substituent in the case of "substituent or unsubstituted” is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • Ring a, ring b and ring c are independent of each other.
  • R 401 and R 402 independently combine with the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle.
  • R 401 and R 402 which do not form the substituted or unsubstituted heterocycle, are independently Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms. )
  • Rings a, b, and c are rings (substituted or unsubstituted ring-forming aromatics having 6 to 50 carbon atoms) that are condensed into a fused bicyclic structure in the center of formula (41) composed of B atoms and two N atoms.
  • the "aromatic hydrocarbon ring" of the a ring, b ring and c ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group”.
  • the "aromatic hydrocarbon ring" of the a ring contains three carbon atoms on the condensed two-ring structure in the center of the formula (41) as ring-forming atoms.
  • the "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms on the condensed bicyclic structure in the center of the formula (41) as ring-forming atoms.
  • the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms” include a compound in which a hydrogen atom is introduced into the "aryl group” described in the specific example group G1.
  • the "heterocycle” of the a ring, b ring and c ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group”.
  • the "heterocycle” of the a ring contains three carbon atoms on the condensed bicyclic structure in the center of the formula (41) as ring-forming atoms.
  • the "heterocycle" of the b ring and the c ring contains two carbon atoms on the condensed bicyclic structure in the center of the formula (41) as ring-forming atoms.
  • Specific examples of the "heterocyclic ring having 5 to 50 substituted or unsubstituted ring-forming atoms” include a compound in which a hydrogen atom is introduced into the "heterocyclic group" described in the specific example group G2.
  • R 401 and R 402 may be independently bonded to the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle.
  • the heterocycle in this case contains a nitrogen atom on the condensed bicyclic structure in the center of the formula (41).
  • the heterocycle in this case may contain a heteroatom other than the nitrogen atom.
  • R 401 may be bonded to ring a to form a nitrogen-containing heterocycle in which a ring containing R 401 and a ring are condensed to form a bicyclic condensation (or tricyclic condensation or more).
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to heterocyclic groups containing nitrogen and having two or more ring condensations in the specific example group G2. The same applies when R 401 binds to the b ring, R 402 binds to the a ring, and R 402 binds to the c ring.
  • the a ring, the b ring, and the c ring in the formula (41) are independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms. In one embodiment, the a-ring, b-ring and c-ring in formula (41) are independently substituted or unsubstituted benzene rings or naphthalene rings, respectively.
  • R 401 and R 402 in formula (41) are independently substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted ring-forming atoms having 5 to 50 atoms, respectively. It is a monovalent heterocyclic group of, preferably an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms.
  • the compound represented by the formula (41) is a compound represented by the following formula (42).
  • R 401A combines with one or more selected from the group consisting of R 411 and R 421 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 402A combines with one or more selected from the group consisting of R 413 and R 414 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 401A and R 402A which do not form the substituted or unsubstituted heterocycle, are independently Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 411 to R 421 Two or more adjacent pairs of R 411 to R 421 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring of. R 411 to R 421 , which do not form the substituted or unsubstituted heterocycle or the substituted or unsubstituted saturated or unsaturated ring, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • R 401A and R 402A of formula (42) are groups corresponding to R 401 and R 402 of formula (41).
  • R 401A and R 411 may be bonded to form a nitrogen-containing heterocycle in which a ring containing these and a benzene ring corresponding to the a ring are condensed to form a bicyclic condensation (or tricyclic condensation or more).
  • Specific examples of the nitrogen-containing heterocycle include compounds corresponding to heterocyclic groups containing nitrogen and having two or more ring condensations in the specific example group G2. The same applies to the case where R 401A and R 412 are combined, the case where R 402A and R 413 are combined, and the case where R 402A and R 414 are combined.
  • R 11 and R 12 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with a 6-membered ring to which they are bonded.
  • the formed fused ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.
  • R 411 to R 421 which do not contribute to ring formation, are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted or unsubstituted ring forming carbon atoms of 6 to 50, respectively.
  • R 411 to R 421 which do not contribute to ring formation, are each independently a hydrogen atom, an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atomic number. It is a monovalent heterocyclic group of 5 to 50.
  • R 411 to R 421 which do not contribute to ring formation, are each independently a hydrogen atom or an substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • R 411 to R 421 which do not contribute to ring formation, are each independently a hydrogen atom or an substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R 411 to R 421.
  • One is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the formula (42) is a compound represented by the following formula (43).
  • R 431 combines with R 446 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 433 combines with R 447 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 434 combines with R 451 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • R 441 combines with R 442 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • Two or more adjacent pairs of R 431 to R 451 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring of.
  • R 431 to R 451 that do not form the substituted or unsubstituted heterocycle or the substituted or unsubstituted saturated or unsaturated ring are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • R 431 may be combined with R 446 to form a substituted or unsubstituted heterocycle.
  • R 431 and R 446 are bonded to form a nitrogen-containing heterocycle having three or more ring condensations in which a benzene ring to which R 46 is bonded, a ring containing N, and a benzene ring corresponding to the a ring are condensed.
  • the nitrogen-containing heterocycle include compounds corresponding to heterocyclic groups containing nitrogen and having three or more ring condensations in the specific example group G2. The same applies when R 433 and R 447 are combined, when R 434 and R 451 are combined, and when R 441 and R 442 are combined.
  • R 431 to R 451 that do not contribute to ring formation are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and substituted or unsubstituted ring forming carbon atoms 6 to 50, respectively.
  • R 431 to R 451 that do not contribute to ring formation are each independently a hydrogen atom, an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atomic number. It is a monovalent heterocyclic group of 5 to 50.
  • R 431 to R 451 that do not contribute to ring formation are independently hydrogen atoms or substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.
  • R 431 to R 451 that do not contribute to ring formation are independently hydrogen atoms or substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, and at least one of R 431 to R 451.
  • One is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43A).
  • R 461 is Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50 carbon atoms.
  • R 462 to R 465 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50 carbon atoms.
  • R 461 to R 465 are independently substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
  • R 461 to R 465 are independently substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43B).
  • R 471 and R 472 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -N (R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • R 473 to R 475 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -N (R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • R 906 and R 907 are as defined by the above equation (1).
  • the compound represented by the formula (43) is a compound represented by the following formula (43B').
  • R 472 to R 475 are as defined in the above formula (43B).
  • R 471 to R 475 is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -N (R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • R 472 is Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, -N (R 906 ) (R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • R 471 and R 473 to R 475 are independent of each other.
  • the compound represented by the formula (43) is a compound represented by the following formula (43C).
  • R 481 and R 482 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50 carbon atoms.
  • R 483 to R 486 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, or an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 50 carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43C').
  • R 483 to R 486 are as defined in the above formula (43C).
  • R 481 to R 486 are independently substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms or substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
  • R 481 to R 486 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
  • the compound represented by the formula (43) is a compound represented by the following formula (43D).
  • R 4611 is a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 10 carbon atoms, -Si (R 911 ) (R 912 ) (R 913 ), or -N (R 914 ) (R 915 ).
  • R 4612 to R 4615 are independently substituted alkyl groups having 1 to 6 carbon atoms, unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms, or -Si (R 911 ) (R 912 ) ( R 913 ).
  • R 911 to R 913 is an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 18 carbon atoms.
  • R 914 to R 915 is an unsubstituted aryl group having 6 to 18 carbon atoms.
  • R 4611 is a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or -N (R 914 ) (R 915 ).
  • R 4612 to R 4615 are independently unsubstituted alkyl groups having 1 to 6 carbon atoms or unsubstituted ring-forming cycloalkyl groups having 3 to 10 carbon atoms, respectively. is there.
  • R 4611 is ⁇ N (R 914 ) (R 915 ), and R 4612 to R 4615 are independently unsubstituted alkyl groups having 1 to 6 carbon atoms. Is.
  • R 4611 is an unsubstituted alkyl group having 1 to 6 carbon atoms
  • R 4612 to R 4615 are independently substituted alkyl having 1 to 6 carbon atoms. Is the basis.
  • R 4611 is a hydrogen atom and R 4612 to R 4615 are independently unsubstituted alkyl groups having 1 to 6 carbon atoms or unsubstituted ring-forming carbon atoms 3 respectively. ⁇ 10 cycloalkyl groups.
  • At least one of the hydrogen atoms of one or more selected from the group consisting of R 914 and R 915 is a deuterium atom.
  • the compound represented by the formula (41) is produced as an intermediate by first binding the a ring, the b ring and the c ring with a linking group ( a group containing N-R 1 and a group containing N-R 2).
  • the final product can be produced by binding (first reaction), a ring, b ring and c ring with a linking group (group containing B) (second reaction).
  • first reaction an amination reaction such as the Buchwald-Hartwig reaction can be applied.
  • a tandem hetero Friedel-Crafts reaction or the like can be applied.
  • the compound represented by the formula (51) will be described.
  • the r ring is a ring represented by the formula (52) or the formula (53) that condenses at an arbitrary position of the adjacent ring.
  • the q-ring and the s-ring are rings represented by the formula (54) that are independently condensed at arbitrary positions of adjacent rings.
  • the p-ring and the t-ring are structures represented by the formula (55) or the formula (56), which are independently condensed at arbitrary positions of adjacent rings.
  • R 501 there are a plurality and do not form a plurality of adjacent R 501 is bonded to either form a ring substituted or unsubstituted, saturated or unsaturated with one another, or a substituted or unsubstituted saturated or unsaturated ring .
  • X 501 is an oxygen atom, a sulfur atom, or an NR 502 .
  • R 501 and R 502 which do not form the substituted or unsaturated saturated or unsaturated ring, Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring
  • R 901 to R 907 are as defined by the above equation (1).
  • Ar 501 and Ar 502 are independent of each other.
  • Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • L 501 is Substituent or unsubstituted alkylene group having 1 to 50 carbon atoms, Substituent or unsubstituted alkenylene group having 2 to 50 carbon atoms, Substituent or unsubstituted alkynylene group having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkylene group having 3 to 50 carbon atoms, It is an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50, or a divalent heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50.
  • m1 is an integer of 0 to 2 independently
  • m2 is an integer of 0 to 4 independently
  • m3 is an integer of 0 to 3 independently
  • m4 is an integer of 0 to 3 independently. It is an integer of 5. If R 501 there are a plurality to plurality of R 501 may be the same as each other or may be different. )
  • each ring from the p ring to the t ring shares two carbon atoms with the adjacent ring and condenses.
  • the position and direction of condensation are not limited, and condensation is possible at any position and direction.
  • R 501 is a hydrogen atom.
  • the compound represented by the formula (51) is represented by any of the following formulas (51-1) to (51-6).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1 and m3 are as defined in the above formula (51).
  • the compound represented by the formula (51) is represented by any of the following formulas (51-11) to (51-13).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1, m3 and m4 are as defined in the above formula (51).
  • the compound represented by the formula (51) is represented by any of the following formulas (51-21) to (51-25).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1 and m4 are as defined in the above formula (51).
  • the compound represented by the formula (51) is represented by any of the following formulas (51-31) to (51-33).
  • R 501 , X 501 , Ar 501 , Ar 502 , L 501 , and m1 to m4 are as defined in the above formula (51).
  • Ar 501 and Ar 502 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.
  • one of Ar 501 and Ar 502 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and the other is a substituted or unsubstituted monovalent heterocyclic ring having 5 to 50 ring-forming atoms. It is a ring group.
  • R 605 to R 608 those that do not form a divalent group represented by the above formula (63), and at least one of R 621 to R 624 are monovalent groups represented by the following formula (64).
  • X 601 is an oxygen atom, a sulfur atom, or an NR 609 .
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are as defined by the above equation (1).
  • Ar 601 and Ar 602 are independent of each other.
  • L 601 to L 603 are independent of each other.
  • the position where the divalent group represented by the formula (62) and the divalent group represented by the formula (63) are formed is not particularly limited, and at the possible positions of R 601 to R 608.
  • the group can be formed.
  • the compound represented by the formula (61) is represented by any of the following formulas (61-1) to (61-6).
  • X 601 is as defined by the formula (61).
  • At least two of R 601 to R 624 are monovalent groups represented by the above formula (64).
  • R601 to R624 which are not monovalent groups represented by the above formula (64), are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • the compound represented by the formula (61) is represented by any of the following formulas (61-7) to (61-18).
  • X 601 is as defined by the formula (61). * Is a single bond to bond to the monovalent group represented by the formula (64) R 601 to R 624 are the same as R 601 to R 624 , which are not monovalent groups represented by the above formula (64).
  • R 601 ⁇ R 608 , and the formula ( R 611 to R 614 and R 621 to R 624 , which are not monovalent groups represented by 64), are preferably independently of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • the monovalent group represented by the formula (64) is preferably represented by the following formula (65) or (66).
  • R 631 to R 640 are independent of each other. Hydrogen atom, Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms
  • HAR 601 has a structure represented by the following formula (67).
  • X 602 is an oxygen atom or a sulfur atom.
  • Any one of R 641 to R 648 is a single bond that binds to L 603.
  • R 641 to R 648 which are not single bonds, are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are
  • a 703 ring is independent of each other Substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, or A substituted or unsubstituted ring-forming heterocycle having 5 to 50 atoms.
  • X 701 is NR 703 , C (R 704 ) (R 705 ), Si (R 706 ) (R 707 ), Ge (R 708 ) (R 709 ), O, S or Se.
  • R 701 and R 702 combine 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 701 and R 702 which do not form a substituted or unsaturated saturated or unsaturated ring, and R 703 to R 709 , respectively, independently.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms
  • a 701 ring and A 702 ring are bonded to a bond * having a structure represented by the formula (72). That is, in one embodiment, the ring-forming carbon atoms of the aromatic hydrocarbon ring A 701 ring, or ring-forming atoms of the heterocycle, binds to bond structure represented by the formula (72) *. Further, in one embodiment, the ring-forming carbon atom of the aromatic hydrocarbon ring of the A 702 ring or the ring-forming atom of the heterocycle is bonded to a bond * having a structure represented by the formula (72).
  • a group represented by the following formula (73) is attached to either or both of the A 701 ring and the A 702 ring.
  • Ar 701 and Ar 702 are independent of each other.
  • L 701 to L 703 are independent of each other.
  • the ring-forming carbon atom of the aromatic hydrocarbon ring of the A 702 ring or the ring-forming atom of the heterocycle is a bond having a structure represented by the formula (72). Combine with *.
  • the structures represented by the formula (72) may be the same or different.
  • R 701 and R 702 are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms. In one embodiment, R 701 and R 702 combine with each other to form a fluorene structure.
  • ring A 701 and ring A 702 are substituted or unsubstituted ring-forming aromatic hydrocarbon rings having 6 to 50 carbon atoms, for example, substituted or unsubstituted benzene rings.
  • ring A 703 is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, for example, a substituted or unsubstituted benzene ring.
  • X 701 is O or S.
  • the compound represented by the formula (81) will be described.
  • the A801 ring is a ring represented by the formula (82) that condenses at an arbitrary position of an adjacent ring.
  • the A 802 ring is a ring represented by the formula (83) that condenses at an arbitrary position of an adjacent ring.
  • X 801 and X 802 are independently C (R 803 ) (R 804 ), Si (R 805 ) (R 806 ), oxygen atom, or sulfur atom.
  • Ring A 803 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
  • Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring forming atoms.
  • R801 to R806 are independent of each other.
  • Hydrogen atom Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atomic atoms.
  • R 901 to R 907 are as defined by the above equation (1).
  • m801 and m802 are each independently an integer of 0 to 2. If m801 is 2, R 801 may be the same or may be different from one another. When m802 is 2, R 802 may be the same as or different from each other.
  • a801 is an integer of 0 to 2. When a801 is 0 or 1, the structures in parentheses indicated by "3-a801" may be the same or different from each other. When a801 is 2, Ar 801 may be the same as or different from each other. )
  • Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
  • ring A 803 is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 50 carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted naphthalene ring. It is a substituted or unsubstituted anthracene ring.
  • R 803 and R 804 are independently substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms.
  • a801 is 1.
  • the organic EL device has a light emitting layer between the cathode, the anode, and the cathode and the anode, and the light emitting layer is the first light emitting layer.
  • Conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired, except that the host material, the second host material, and the dopant material are included.
  • the content of the first host material and the second host material in the light emitting layer is preferably 80% by mass or more and 99% by mass or less with respect to the entire light emitting layer.
  • the content ratio (mass ratio) of the first host material and the second host material in the light emitting layer is usually 1:99 to 99: 1, preferably 10:90 to 90:10, and 40:60 to 40. 60:40 is more preferable.
  • the content of the dopant material in the light emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light emitting layer.
  • One aspect of the organic EL device of the present invention preferably has a hole transport layer between the anode and the light emitting layer.
  • One aspect of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the light emitting layer.
  • anophode / light emitting layer / cathode (2) Anodium / hole injection layer / light emitting layer / cathode (3) Anodium / light emitting layer / electron injection / transport layer / cathode (4) Anodium / hole injection layer / light emitting layer / Electron injection / transport layer / Cathode (5) Anodic / Organic semiconductor layer / Light emitting layer / Cathode (6) Anodic / Organic semiconductor layer / Electronic barrier layer / Light emitting layer / Cathode (7) Anodic / Organic semiconductor layer / Light emitting layer / Adhesion improvement layer / cathode (8) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode (9) anode / insulating layer / light emitting layer / insulating layer / cathode (10) anode
  • hole injection / transport layer means “at least one of a hole injection layer and a hole transport layer”
  • electron injection / transport layer means “electron injection layer and electron”. It means “at least one of the transport layers”.
  • the substrate is used as a support for the light emitting element.
  • the substrate for example, glass, quartz, plastic or the like can be used.
  • the flexible substrate is a bendable (flexible) substrate, and examples thereof include a plastic substrate made of polycarbonate and polyvinyl chloride.
  • anode For the anode formed on the substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound, a mixture thereof, or the like.
  • a metal having a large work function specifically, 4.0 eV or more
  • ITO Indium Tin Oxide
  • indium tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
  • tungsten oxide tungsten oxide
  • indium oxide containing zinc oxide Graphene and the like.
  • gold (Au) platinum (Pt), a nitride of a metallic material (for example, titanium nitride) and the like can be mentioned.
  • the hole injection layer is a layer containing a substance having a high hole injection property.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, renium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, etc.
  • Tungsten oxides, manganese oxides, aromatic amine compounds, polymer compounds (oligoforms, dendrimers, polymers, etc.) and the like can also be used.
  • the hole transport layer is a layer containing a substance having a high hole transport property.
  • An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer.
  • Polymer compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • any substance other than these may be used as long as it is a substance having a higher hole transport property than electrons.
  • the layer containing the substance having a high hole transport property is not limited to a single layer, but may be a layer in which two or more layers made of the above substances are laminated.
  • the light emitting layer is a layer containing a substance having high light emission, and various materials can be used in addition to the materials used in the present invention described above.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as a substance having high luminescence.
  • a fluorescent compound is a compound capable of emitting light from a singlet excited state
  • a phosphorescent compound is a compound capable of emitting light from a triplet excited state.
  • a bluish fluorescent light emitting material that can be used for the light emitting layer
  • a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative and the like can be used.
  • a greenish fluorescent light emitting material that can be used for the light emitting layer an aromatic amine derivative or the like can be used.
  • a red-based fluorescent light emitting material that can be used for the light emitting layer a tetracene derivative, a diamine derivative, or the like can be used.
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used.
  • An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used.
  • the light emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material).
  • the substance for dispersing the highly luminescent substance various materials can be used in addition to the material used in the present invention described above, and the lowest empty orbital level (LUMO level) is higher than that of the highly luminescent substance. It is preferable to use a substance having a high position) and a low maximum occupied orbital level (HOMO level).
  • Examples of the substance (host material) for dispersing a highly luminescent substance include 1) a metal complex such as an aluminum complex, a berylium complex, or a zinc complex, and 2) an oxadiazole derivative, a benzoimidazole derivative, a phenanthroline derivative, or the like. Heterocyclic compounds, 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives. used.
  • the electron transport layer is a layer containing a substance having a high electron transport property.
  • the electron transport layer includes 1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes, 2) heteroarocyclic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives, and 3) polymer compounds. Can be used.
  • the electron injection layer is a layer containing a substance having a high electron injection property.
  • the electron injection layer includes lithium (Li), itterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc.
  • Metal complex compounds, alkali metals such as lithium oxide (LiO x ), alkaline earth metals, or compounds thereof can be used.
  • cathode As the cathode, it is preferable to use a metal having a small work function (specifically, 3.8 eV or less), an alloy, an electrically conductive compound, a mixture thereof, or the like.
  • a cathode material include elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), and calcium (Mg).
  • alkaline earth metals such as Ca) and strontium (Sr)
  • rare earth metals such as alloys containing them (for example, MgAg and AlLi), europium (Eu) and ytterbium (Yb), and alloys containing these.
  • the method of forming each layer is not particularly limited.
  • a conventionally known forming method such as a vacuum vapor deposition method or a spin coating method can be used.
  • Each layer such as a light emitting layer is known by a vacuum vapor deposition method, a molecular beam vapor deposition method (MBE method), a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like. It can be formed by a method.
  • MBE method molecular beam vapor deposition method
  • a first host material, a second host material, and a dopant material are simultaneously vapor-deposited (co-deposited) from different vapor deposition sources to form a single light-emitting layer.
  • a method of forming may be adopted, or a method of premixing some materials (for example, a first host material and a second host material) and then co-depositing with other materials may be adopted.
  • the former method has a problem that the manufacturing process is complicated, there is a concern that the device performance may be deteriorated due to the interaction at the time of premixing because each material is layered without contacting in advance. small.
  • the latter method has problems such as the possibility of interaction of each material due to premixing and the tendency of the material ratio to become unstable during vapor deposition, but has the advantage of simplifying the manufacturing apparatus and manufacturing process.
  • a composition according to one aspect of the present invention described later may be used.
  • the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, suppress the applied voltage low, and improve the luminous efficiency, it is usually from several nm. The range of 1 ⁇ m is preferable.
  • composition includes a compound represented by the above formula (1) and a compound represented by the above formula (2).
  • the compound represented by the above formula (1) and the compound represented by the above formula (2) contained in the composition are different compounds. Details of each material are as described above.
  • the form of the composition in one aspect of the present invention is not particularly limited, and examples thereof include solids, powders, solutions, and membranes. When it is a solid, it may be molded into pellets.
  • the above-mentioned "membrane” includes a film formed by containing a raw material, which comprises a compound represented by the formula (1) and a compound represented by the formula (2). Examples of such a film include a light emitting layer containing a first host material, a second host material, and a dopant material in the organic electroluminescence device according to one aspect of the present invention.
  • Examples of the compound represented by the above formula (1) and the compound represented by the above formula (2) included in the composition include the following compounds, and a composition in which they are combined is preferable.
  • two or more L1A are independently single-bonded or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms.
  • Two or more Ar 1A are independently unsubstituted aryl groups having 6 to 50 carbon atoms.
  • one or more of R 1A to R 8A are independently deuterium atoms.
  • R 1A to R 8A are deuterium atoms.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-11), formula (2-12) or formula (2-13).
  • R 1B to R 8B , R 11B to R 13B , X 11B and Ar 1B are as defined in the above formula (2).
  • R 14B to R 21B are independent of each other.
  • X 11B is an oxygen atom.
  • the compound represented by the formula (2) is a compound represented by the following formula (2-21), formula (2-22) or formula (2-23).
  • Ar 1B is as defined by the above formula (2).
  • Ar 1B is an unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and the aryl group has one or more deuterium atoms. In one embodiment, in Formula (2), Ar 1B has a -C 6 D 5 group.
  • the combination of the compounds described here is a first host material (compound represented by the above formula (1)) used in the organic electroluminescence element according to one aspect of the present invention and a second host material (the above formula (the above formula (1) The combination with the compound) represented by 2) is also a preferable combination.
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1) and one or more compounds.
  • As the compound represented by the formula (2) from the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3). With one or more compounds selected from the group including.
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1) and one or more compounds.
  • As the compound represented by the formula (2) from the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13). With one or more compounds selected from the group including.
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1) and one or more compounds.
  • As the compound represented by the formula (2) from the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23). With one or more compounds selected from the group including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-2) and one or more compounds.
  • As the compound represented by the formula (2) the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-2) and one or more compounds.
  • As the compound represented by the formula (2) the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-2) and one or more compounds.
  • As the compound represented by the formula (2) the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • R 21 is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming mono
  • R 901 to R 907 are as defined by the above equation (1).
  • m1 is an integer from 0 to 4.
  • m2 is an integer from 0 to 5.
  • m3 is an integer from 0 to 7.
  • the plurality of R 21s may be the same as each other or may be different from each other.
  • the plurality of adjacent R 21s are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • the compound represented by the formula (2) the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • the compound represented by the formula (2) the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • the compound represented by the formula (2) the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-2), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-2), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-2), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • the compound represented by the formula (2) the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • the compound represented by the formula (2) the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • the compound represented by the formula (2) the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1) and one or more compounds.
  • As the compound represented by the formula (2) from the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • Ar 1B is one or more compounds selected from the group consisting of groups represented by any of the following formulas (a1) to (a4), and compounds selected from the group consisting of groups. including.
  • R 21 is Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, -Si (R 901 ) (R 902 ) (R 903 ), -O- (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming mono
  • R 901 to R 907 are as defined by the above equation (1).
  • m1 is an integer from 0 to 4.
  • m2 is an integer from 0 to 5.
  • m3 is an integer from 0 to 7.
  • the plurality of R 21s may be the same as each other or may be different from each other.
  • the plurality of adjacent R 21s are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1) and one or more compounds.
  • As the compound represented by the formula (2) from the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • Ar 1B is one or more compounds selected from the group consisting of the groups represented by any of the above formulas (a1) to (a4). including.
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1) and one or more compounds.
  • As the compound represented by the formula (2) from the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • Ar 1B is one or more compounds selected from the group consisting of the groups represented by any of the above formulas (a1) to (a4). including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is as the compound represented by the formula (1), one or more compounds represented by the formula (1-2) and one or more compounds.
  • the compound represented by the formula (2) the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is as the compound represented by the formula (1), one or more compounds represented by the formula (1-2) and one or more compounds.
  • the compound represented by the formula (2) the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is as the compound represented by the formula (1), one or more compounds represented by the formula (1-2) and one or more compounds.
  • the compound represented by the formula (2) the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-1), the compound represented by the formula (2-2), and the compound represented by the formula (2-3).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-11), the compound represented by the formula (2-12), and the compound represented by the formula (2-13).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • One or more compounds selected from the group consisting of compounds As the compound represented by the formula (2), the compound represented by the formula (2-21), the compound represented by the formula (2-22), and the compound represented by the formula (2-23).
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1B is one or more compounds selected from the group consisting of the groups represented by any of the above formulas (a1) to (a4). including.
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1B is one or more compounds selected from the group consisting of the groups represented by any of the above formulas (a1) to (a4). including.
  • the composition is As the compound represented by the formula (1), one or more compounds represented by the formula (1-1), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1B is one or more compounds selected from the group consisting of the groups represented by any of the above formulas (a1) to (a4). including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-11), the compound represented by the formula (1-12), and the compound represented by the formula (1-13).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is as the compound represented by the formula (1), one or more compounds represented by the formula (1-2), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is as the compound represented by the formula (1), one or more compounds represented by the formula (1-2), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is as the compound represented by the formula (1), one or more compounds represented by the formula (1-2), in which Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1A is independently any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition is As the compound represented by the formula (1), the compound represented by the formula (1-21), the compound represented by the formula (1-22), and the compound represented by the formula (1-23).
  • Ar 1A is independently selected from the group consisting of groups represented by any of the above formulas (a1) to (a4).
  • Ar 1B is selected from the group consisting of groups represented by any of the above formulas (a1) to (a4), and including.
  • the composition comprises a combination of a compound represented by the formula (1) described in the table below and a compound represented by the formula (2).
  • 1-1 to 1-216 indicate compound numbers of specific examples of the compound represented by the formula (1)
  • 2-1 to 2-475 are represented by the formula (2).
  • the compound numbers of specific examples of compounds are shown.
  • the combinations of the specific example compounds of the formula (1) and the specific example compounds of the formula (2) are indicated by numbers 1 to 102,600 in the table below.
  • composition As the compound represented by the formula (1), one or more compounds selected from the following group A and one or more compounds As the compound represented by the formula (2), one or more compounds selected from the following group B and including.
  • the compounding ratio of the compound represented by the formula (1) and the compound represented by the formula (2) is not particularly limited.
  • the compounding ratio of the materials may be appropriately determined according to the effect required for the composition.
  • the compounding ratio (mass ratio) of the compound represented by the formula (1) and the compound represented by the formula (2) is usually 1:99 to 99: 1, preferably 10:90 to 90:10. , 40:60 to 60:40 are more preferable.
  • the composition is a powder comprising a compound represented by the formula (1) and a compound represented by the formula (2).
  • the composition according to one aspect of the present invention may be in the form of powder.
  • the powder may contain a compound represented by the formula (1) and a compound represented by the above formula (2) in one particle, or a particle composed of the compound represented by the formula (1).
  • particles composed of the compound represented by the formula (2) may be mixed.
  • the compounding ratio of the compound represented by the formula (1) and the compound represented by the formula (2) is not particularly limited, and the composition is as described above.
  • the powder is sometimes called a premix.
  • composition according to one aspect of the present invention may contain a compound represented by the above formula (1) and a component other than the compound represented by the above formula (2).
  • examples of other components include the above-mentioned dopant materials and the like. The details of the dopant material are as described above.
  • the electronic device is characterized by comprising an organic EL element according to one aspect of the present invention.
  • electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light emitting devices such as lighting or vehicle lamps.
  • the compound (second host material) represented by the formula (2) used in Examples and Comparative Examples is shown below.
  • Example 1 Manufacturing of organic EL element>
  • a glass substrate manufactured by Geomatic Co., Ltd.
  • an ITO transparent electrode anode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the cleaned glass substrate with a transparent electrode is mounted on the substrate holder of the vacuum vapor deposition apparatus, and first, the compound HI-1 and the compound HT-1 are compounded so as to cover the transparent electrode on the surface on the side where the transparent electrode is formed. Co-deposited so that the ratio of HI-1 was 3% by mass to form a hole injection layer having a thickness of 10 nm.
  • the compound HT-1 was deposited on the hole injection layer to form an HT-1 film having a film thickness of 75 nm.
  • This HT-1 membrane functions as a hole transport layer (first hole transport layer).
  • the compound HT-2 was deposited to form an HT-2 film having a film thickness of 15 nm on the HT-1 film.
  • This HT-2 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH1-1 (first host material), compound BH2-1 (second host material), and compound BD-1 (dopant material) are co-deposited on the HT-2 film, and BH1-1: 1 having a film thickness of 20 nm.
  • a BH2-1: BD-1 film was formed.
  • This BH1-1: BH2-1: BD-1 film functions as a light emitting layer.
  • BH1-1 and BH2-1 contained in the light emitting layer have a mass ratio of 1: 1 and the concentration of BD-1 is 2% by mass with respect to the entire light emitting layer.
  • the compound ET-1 was deposited on the light emitting layer to form an ET-1 film having a film thickness of 3 nm.
  • This ET-1 film functions as a hole barrier layer (first electron transport layer).
  • the compound ET-2 and lithium (8-quinolinolato) (hereinafter, also referred to as Liq) were co-deposited to form an ET-2: Liq film having a Liq ratio of 33% by mass and a film thickness of 30 nm.
  • This ET-2 Liq film functions as an electron transport layer (second electron transport layer). LiF and Yb were co-deposited on the ET-2: Liq film to form a LiF: Yb film having a Yb ratio of 50% and a film thickness of 1 nm. A metal Al was vapor-deposited on the LiF: Yb film to form a metal cathode having a film thickness of 50 nm, and an organic EL device was produced.
  • the element configuration of the organic EL element of the first embodiment is shown as follows. ITO (130) / HT-1: HI-1 (10; 3%) / HT-1 (75) / HT-2 (15) / BH1-1: BH2-1: BD-1 (20; 2%) / ET-1 (3) / ET-2: Liq (30; 33%) / LiF: Yb (1; 50%) / Al (50)
  • the first numerical value in parentheses represents the film thickness (unit: nm), and% represents the mass% of the compound described last with respect to the entire layer.
  • Example 2 In Example 1, except that the first host material and the second host material are mixed (premixed) in advance to prepare a composition, and then the composition and the dopant material are co-deposited to form a light emitting layer. Made an organic EL device in the same manner as in Example 1 and evaluated it. The results are shown in Table 1. Two materials (first host material and second host material) could be stably vapor-deposited from one vapor deposition source, and desired device performance could be obtained.
  • Examples 2-2 to 2-4 An organic EL device was prepared and evaluated by the same method (premix) as in Example 2 except that the compounds shown in Table 1 were used as the host material for the light emitting layer. The results are shown in Table 1.
  • Comparative Examples 1-2 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 1 were used as the host material for the light emitting layer. The results are shown in Table 1.
  • Example 3 Manufacturing of organic EL element>
  • a glass substrate manufactured by Geomatic Co., Ltd.
  • an ITO transparent electrode anode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the glass substrate with a transparent electrode after cleaning is mounted on the substrate holder of the vacuum vapor deposition apparatus, and the compound HI-2 is first vapor-deposited on the surface on the side where the transparent electrode is formed so as to cover the transparent electrode, and the film thickness is 5 nm.
  • a hole injection layer was formed.
  • the compound HT-3 was deposited on the hole injection layer, and an HT-3 film having a film thickness of 80 nm was formed on the HI-2 film.
  • This HT-3 membrane functions as a hole transport layer (first hole transport layer).
  • the compound HT-4 was deposited to form an HT-4 film having a thickness of 10 nm on the HT-3 film.
  • This HT-4 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH1-2 (first host material), compound BH2-1 (second host material), and compound BD-1 (dopant material) are co-deposited on the HT-4 film, and BH1-2 having a film thickness of 25 nm: A BH2-1: BD-1 film was formed.
  • This BH1-2: BH2-1: BD-1 film functions as a light emitting layer.
  • BH1-2 and BH2-1 contained in the light emitting layer have a mass ratio of 1: 1 and the concentration of BD-1 is 2% by mass with respect to the entire light emitting layer.
  • the compound ET-3 was deposited on the light emitting layer to form an ET-3 film having a film thickness of 10 nm.
  • This ET-3 film functions as a hole barrier layer (first electron transport layer).
  • ET-4 and Li were co-deposited to form an ET-4: Li film having a Li ratio of 4% by mass and a film thickness of 15 nm.
  • a metal Al was vapor-deposited on the ET-4: Li film to form a metal cathode having a film thickness of 50 nm, and an organic EL device was produced.
  • the element configuration of the organic EL element of Example 3 is shown as follows. ITO (130) / HI-2 (5) / HT-3 (80) / HT-4 (10) / BH1-2: BH2-1: BD-1 (25; 2%) / ET-3 (10) / ET-4: Li (15; 4%) / Al (50)
  • the first numerical value in parentheses represents the film thickness (unit: nm), and% represents the mass% of the compound described at the end with respect to the entire layer.
  • Comparative Examples 3-4 An organic EL device was prepared and evaluated by the same method as in Example 3 except that the compounds shown in Table 2 were used as the host material for the light emitting layer. The results are shown in Table 2.
  • Example 4 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 3 were used as the host material for the light emitting layer. The results are shown in Table 3. The values in parentheses in Table 3 indicate the difference between the voltage and the voltage of Comparative Example 5, and the EQE and LT95 show relative values with the result of Comparative Example 5 as 100%.
  • Comparative Example 5 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 3 were used as the host material for the light emitting layer. The results are shown in Table 3.
  • Examples 2-5 and 2-6 An organic EL device was prepared and evaluated by the same method (premix) as in Example 2 except that the compounds shown in Table 3 were used as the host material for the light emitting layer. The results are shown in Table 3.
  • Example 5 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 4 were used as the host material for the light emitting layer. The results are shown in Table 4. The values in parentheses in Table 4 indicate the difference from the voltage of Comparative Example 6 for the voltage, and indicate the relative values of EQE and LT95 with the result of Comparative Example 6 as 100%.
  • Comparative Examples 6-7 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 4 were used as the host material for the light emitting layer. The results are shown in Table 4.
  • Example 6 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 5 were used as the host material for the light emitting layer. The results are shown in Table 5. The values in parentheses in Table 5 indicate the difference from the voltage of Comparative Example 8 for the voltage, and indicate the relative values of EQE and LT95 with the result of Comparative Example 8 as 100%.
  • Comparative Example 8 An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in Table 5 were used as the host material for the light emitting layer. The results are shown in Table 5.
  • Example 7 Manufacturing of organic EL element>
  • a glass substrate manufactured by Geomatic Co., Ltd.
  • an ITO transparent electrode anode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the cleaned glass substrate with a transparent electrode is mounted on the substrate holder of the vacuum vapor deposition apparatus, and first, the compound HI-1 and the compound HT-5 are compounded so as to cover the transparent electrode on the surface on the side where the transparent electrode is formed. Co-deposited so that the ratio of HI-1 was 3% by mass to form a hole injection layer having a thickness of 10 nm.
  • the compound HT-5 was deposited on the hole injection layer to form an HT-5 film having a film thickness of 75 nm.
  • This HT-5 membrane functions as a hole transport layer (first hole transport layer).
  • the compound HT-2 was deposited to form an HT-2 film having a film thickness of 15 nm on the HT-5 film.
  • This HT-2 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH1-1 (first host material), compound BH2-1 (second host material), and compound BD-1 (dopant material) are co-deposited on the HT-2 film, and BH1-1: 1 having a film thickness of 20 nm.
  • a BH2-1: BD-1 film was formed.
  • This BH1-1: BH2-1: BD-1 film functions as a light emitting layer.
  • concentrations of BH1-1, BH2-1 and BD-1 contained in the light emitting layer are 58.8% by mass, 39.2% by mass and 2% by mass, respectively, with respect to the entire light emitting layer.
  • the mass ratio of BH1-1: BH2-1 contained in the light emitting layer is 6: 4.
  • the light emitting layer uses a composition in which the first host material BH1-1 and the second host material BH2-1 are mixed (premixed) in advance, and the composition and the dopant material BD-1 are co-deposited.
  • a composition in which the first host material BH1-1 and the second host material BH2-1 are mixed (premixed) in advance, and the composition and the dopant material BD-1 are co-deposited.
  • Two materials first host material and second host material) could be stably vapor-deposited from one vapor deposition source.
  • the compound ET-5 was deposited on the light emitting layer to form an ET-5 film having a film thickness of 3 nm.
  • This ET-5 film functions as a hole barrier layer (first electron transport layer).
  • the compound ET-2 and lithium (8-quinolinolato) (hereinafter, also referred to as Liq) were co-deposited to form an ET-2: Liq film having a Liq ratio of 33% by mass and a film thickness of 30 nm.
  • LiF and Yb were co-deposited on the ET-2: Liq film to form a LiF: Yb film having a Yb ratio of 50% and a film thickness of 1 nm.
  • a metal Al was vapor-deposited on the LiF: Yb film to form a metal cathode having a film thickness of 50 nm, and an organic EL device was produced.
  • the element configuration of the organic EL element of Example 7 is shown as follows. ITO (130) / HT-5: HI-1 (10; 3%) / HT-5 (75) / HT-2 (15) / BH1-1: BH2-1: BD-1 (20; 58.8) %: 39.2%: 2%) / ET-5 (3) / ET-2: Liq (30; 33%) / LiF: Yb (1; 50%) / Al (50)
  • the first numerical value in parentheses represents the film thickness (unit: nm), and% represents the mass% of the compound described at the end with respect to the entire layer or the mass% of each compound contained in the layer.
  • Examples 8-10 An organic EL device was prepared and evaluated by the same method as in Example 7 except that the compounds shown in Table 6 were used as the host material for the light emitting layer. The results are shown in Table 6.
  • Examples 11 and 12 An organic EL device was produced by the same method as in Example 7 except that the first host material and the second host material shown in Table 7 were used as the host materials for the light emitting layer in the proportions shown in Table 7. Evaluation was performed in the same manner as in Example 1. The results are shown in Table 7.
  • Examples 13 to 15 An organic EL device was produced by the same method as in Example 7 except that the first host material and the second host material shown in Table 8 were used as the host materials for the light emitting layer in the proportions shown in Table 8. Evaluation was performed in the same manner as in Example 1. The results are shown in Table 8.
  • Example A Manufacture of an organic EL device using the compound represented by the formula (3-2) as a single host material>
  • a glass substrate manufactured by Geomatic Co., Ltd.
  • an ITO transparent electrode anode having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the cleaned glass substrate with a transparent electrode is attached to the substrate holder of the vacuum vapor deposition apparatus, and the compound HI-2 is first vapor-deposited on the surface on the side where the transparent electrode is formed so as to cover the transparent electrode, and the film thickness is 5 nm.
  • a hole injection layer was formed.
  • the compound HT-6 was deposited on the hole injection layer to form an HT-6 film having a film thickness of 80 nm.
  • This HT-6 membrane functions as a hole transport layer (first hole transport layer).
  • the compound HT-7 was deposited to form an HT-7 film having a film thickness of 10 nm on the HT-6 film.
  • This HT-7 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH2-1D (host material) and compound BD-2 (dopant material) were co-deposited on the HT-7 film to form a BH2-1D: BD-2 film having a film thickness of 25 nm.
  • This BH2-1D: BD-2 film functions as a light emitting layer.
  • the concentration of BD-2 contained in the light emitting layer is 4% by mass with respect to the entire light emitting layer.
  • the compound ET-5 was deposited on the light emitting layer to form an ET-5 film having a film thickness of 10 nm. This ET-5 film functions as a hole barrier layer (first electron transport layer).
  • the compound ET-2 was vapor-deposited to form an ET-2 film having a film thickness of 15 nm. This ET-2 film functions as an electron transport layer (second electron transport layer).
  • LiF was vapor-deposited on the ET-2 film to form a LiF film having a film thickness of 1 nm.
  • a metal Al was vapor-deposited on the LiF film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.
  • the element configuration of the organic EL element of Example A is shown as follows. ITO (130) / HI-2 (5) / HT-6 (80) / HT-7 (10) / BH2-1D: BD-2 (25; 4%) / ET-5 (10) / ET-2 (15) / LiF (1) / Al (80)
  • the first numerical value in parentheses represents the film thickness (unit: nm), and% represents the mass% of the compound described at the end with respect to the entire layer.
  • Comparative Example B An organic EL device was prepared and evaluated by the same method as in Example A except that the compounds shown in Table 9 were used as the host material for the light emitting layer. The results are shown in Table 9.
  • Synthesis Example 3 Synthesis of compound BH2-5D
  • Compound BH2-5D (compound represented by the formula (3-1)) was synthesized according to the following synthesis scheme.

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PCT/JP2020/048995 2019-12-26 2020-12-25 有機エレクトロルミネッセンス素子、組成物、粉体、電子機器、及び新規化合物 Ceased WO2021132667A1 (ja)

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CN202511216182.0A CN121085874A (zh) 2019-12-26 2020-12-25 有机电致发光元件、组合物、粉体、电子设备、和新型化合物
US17/633,887 US12581850B2 (en) 2019-12-26 2020-12-25 Organic electroluminescence element, composition, powder, electronic equipment, and novel compound
KR1020257004304A KR20250024867A (ko) 2019-12-26 2020-12-25 유기 일렉트로루미네센스 소자, 조성물, 분체, 전자 기기, 및 신규 화합물
JP2021567727A JP7328358B2 (ja) 2019-12-26 2020-12-25 有機エレクトロルミネッセンス素子、組成物、粉体、電子機器、及び新規化合物
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