WO2020116562A1 - Organic electroluminescence element and electronic device - Google Patents

Organic electroluminescence element and electronic device Download PDF

Info

Publication number
WO2020116562A1
WO2020116562A1 PCT/JP2019/047626 JP2019047626W WO2020116562A1 WO 2020116562 A1 WO2020116562 A1 WO 2020116562A1 JP 2019047626 W JP2019047626 W JP 2019047626W WO 2020116562 A1 WO2020116562 A1 WO 2020116562A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
ring
substituted
unsubstituted
carbon atoms
Prior art date
Application number
PCT/JP2019/047626
Other languages
French (fr)
Japanese (ja)
Inventor
聡美 田崎
太郎 八巻
竜志 前田
裕基 中野
裕亮 糸井
良多 高橋
Original Assignee
出光興産株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 出光興産株式会社 filed Critical 出光興産株式会社
Publication of WO2020116562A1 publication Critical patent/WO2020116562A1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to an organic electroluminescence element and electronic equipment.
  • an organic electroluminescence element hereinafter, sometimes 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 that a compound having a specific condensed ring structure is used as a material of a light emitting layer of an organic EL element.
  • An object of the present invention is to provide an organic EL element which is driven at a low voltage and has a long life, and an electronic device using the organic EL element.
  • the following organic EL element and electronic device are provided.
  • At least one of R 1 to R 8 is —L 13 —Ar 13 .
  • L 11 to L 13 are each independently Single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms. When two or more L 13's are present, the two or more L 13 's may be the same as or different from each other.
  • Ar 11 to Ar 13 are each independently It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • R 1 to R 8 which are not —L 13 —Ar 13 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • Ring A is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms, or a benzene ring represented by the following formula (X).
  • X benzene ring represented by the following formula (X).
  • One of the two ring-forming carbon atoms represented by * is bonded to * extending from the benzene ring B of the formula (11-1) or (11-2), and the other benzene of the formula (11-3). Bond with a single bond extending from ring C.
  • the two * in the formula (11-1) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
  • the three *'s in the formula (11-2) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
  • R 101 to R 116 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
  • R 101 to R 116 and R 117 that do not form a ring are each independently Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S-
  • R 901 to R 909 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • n is an integer of 1 or 2.
  • n is 2, the two R 117 may be the same or different.
  • An electronic device comprising the organic electroluminescence element according to 1 above.
  • an organic EL element that is driven at a low voltage and has a long life, and an electronic device using the organic EL element.
  • the hydrogen atom includes isotopes having different neutron numbers, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a deuterium atom, a deuterium atom, or a hydrogen atom is present at a bondable position where a symbol such as “R” or “D” that represents a deuterium atom is not specified. It is assumed that tritium atoms are bonded.
  • the ring-forming carbon number constitutes the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridge compound, a carbocyclic compound, a heterocyclic compound). Represents the number of carbon atoms in an atom.
  • a substituent When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number. The same applies to the “ring carbon number” described below unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring 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 number of ring-forming atoms means a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic ring, a condensed ring, a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle Represents the number of atoms constituting the ring itself of the ring compound).
  • An atom that does not form a ring for example, a hydrogen atom that terminates the bond of atoms that form a ring
  • an atom included in a substituent when the ring is substituted with a substituent is not included in the number of ring-forming atoms.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • Hydrogen atoms bonded to carbon atoms of the pyridine ring or quinazoline ring or atoms constituting a substituent are not included in the number of ring-forming atoms.
  • the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” means the number of carbon atoms when the ZZ group is unsubstituted. If present, the carbon number of the substituent is not included.
  • “YY” is larger than “XX”, and "XX” and “YY” each mean an integer of 1 or more.
  • atom number XX to YY in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms when the ZZ group is unsubstituted. The number of atoms of the substituent when it is included is not included.
  • YY is larger than “XX”
  • XX and YY each mean an integer of 1 or more.
  • “substituted” in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with substituents.
  • 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 groups.
  • the substituents described in the present specification will be described below.
  • the number of ring-forming carbon atoms of the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. ..
  • the number of ring-forming atoms of the “unsubstituted heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification. is there.
  • the "unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20, and more preferably 1 to 6 unless otherwise specified in the present specification.
  • the carbon number of the “unsubstituted alkenyl group” described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
  • the "unsubstituted alkynyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in the present specification.
  • the number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in the present specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in the present specification. is there.
  • the number of ring-forming carbon atoms of the “unsubstituted arylene group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. ..
  • the number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 unless otherwise specified in the present specification. ⁇ 18.
  • the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in the present specification.
  • substituted or unsubstituted aryl group examples include the following unsubstituted aryl groups and substituted aryl groups.
  • the unsubstituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group”, and the substituted aryl group is the “substituted or unsubstituted aryl group”.
  • substituted aryl group is used below.
  • aryl group includes both "unsubstituted aryl group” and "substituted aryl group”.
  • the “substituted aryl group” is a case where the “unsubstituted aryl group” has a substituent, and examples thereof include a group in which the “unsubstituted aryl group” has a substituent and a substituted aryl group. ..
  • the examples of the “unsubstituted aryl group” and the “substituted aryl group” listed here are merely examples, and the “substituted aryl group” described in the present specification includes “unsubstituted aryl group”.
  • a group in which the "group” has a substituent further has a substituent, a group in which the "substituted aryl group” further has a substituent, and the like are also included.
  • aryl group Phenyl group, p-biphenyl group, m-biphenyl group, an 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, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, Anthryl group, A benzoanthryl group, Phenanthryl group, A benzophenanthryl group, Phenalenyl group, A pyrenyl group, A chrysenyl group, A benzochrysenyl group, A
  • Substituted aryl group o-tolyl group, m-tolyl group, p-tolyl group, Para-xylyl group, Meta-xylyl group, Ortho-xylyl 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-di(4-methylphenyl)fluorenyl group, 9,9-di(4-isopropylphenyl)fluorenyl group, 9,9-di(4-tbutylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Tri
  • heterocyclic group is a cyclic group containing at least one hetero atom as a 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 in the present specification may be a monocyclic group or a condensed ring group.
  • the “heterocyclic group” described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.
  • substituted or unsubstituted heterocyclic group examples include the following unsubstituted heterocyclic groups and substituted heterocyclic groups.
  • unsubstituted heterocyclic group refers to the case where the “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”
  • substituted heterocyclic group refers to a “substituted or unsubstituted heterocyclic group”.
  • heterocyclic group means a "substituted heterocyclic group”.
  • heterocyclic group when simply referred to as “heterocyclic group”, it means both "unsubstituted heterocyclic group” and "substituted heterocyclic group”. Including.
  • the “substituted heterocyclic group” is a case where the “unsubstituted heterocyclic group” has a substituent, and the following “unsubstituted heterocyclic group” is a group having a substituent or an example of a substituted heterocyclic group. Etc.
  • the “unsubstituted heterocyclic group” and the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in the present specification includes “none A group in which the "substituted heterocyclic group” has a substituent further has a substituent, a group in which the "substituted heterocyclic group” further has a substituent, and the like are also included.
  • An unsubstituted heterocyclic group containing a nitrogen atom A pyrrolyl group, An imidazolyl group, A pyrazolyl group, Triazolyl group, A tetrazolyl group, An oxazolyl group, An isoxazolyl group, Oxadiazolyl group, Thiazolyl group, An isothiazolyl group, Thiadiazolyl group, A pyridyl group, A pyridazinyl group, A pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl group, Isoindolyl group, An indolizinyl group, A quinolidinyl group, Quinolyl group, An isoquinolyl group, Cinnolyl group, Phthalazinyl group, A quinazolinyl group, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthroliny
  • An unsubstituted heterocyclic group containing an oxygen atom Frill group, An oxazolyl group, An isoxazolyl group, Oxadiazolyl group, A xanthenyl group, A benzofuranyl group, An isobenzofuranyl group, A dibenzofuranyl group, Naphthobenzofuranyl group, A benzoxazolyl group, A benzisoxazolyl group, A phenoxazinyl group, Morpholino group, Dinaphthofuranyl group, An azadibenzofuranyl group, A diazadibenzofuranyl group, An azanaphthobenzofuranyl group, Diazanaphthobenzofuranyl group
  • Substituted heterocyclic group containing a nitrogen atom (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, A diphenylcarbazol-9-yl group, Phenylcarbazol-9-yl group, A methylbenzimidazolyl group, An ethylbenzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, A diphenyltriazinyl group, Phenylquinazolinyl group, Biphenylylquinazolinyl group
  • Substituted heterocyclic group containing a sulfur atom Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, Monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene]
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the heterocycles represented by the above formulas (XY-1) to (XY-18) have a bond at any position to become a monovalent heterocyclic group.
  • a monovalent group derived from an unsubstituted heterocycle represented by any of the above formulas (XY-1) to (XY-18) has a substituent means that the carbon atoms constituting the skeleton in these formulas have when bonded hydrogen atoms is replaced by a substituent, or, X a and Y a is NH or CH 2, hydrogen atoms in these NH or CH 2 may refer to a state in which is replaced by a substituent.
  • substituted or unsubstituted alkyl group examples include the following unsubstituted alkyl groups and substituted alkyl groups.
  • the unsubstituted alkyl group refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”, and the substituted alkyl group is the “substituted or unsubstituted alkyl group”.
  • substituted alkyl group is used below.
  • alkyl group includes both "unsubstituted alkyl group” and "substituted alkyl group”.
  • the “substituted alkyl group” is a case where the “unsubstituted alkyl group” has a substituent, and examples thereof include a group in which the “unsubstituted alkyl group” has a substituent and a substituted alkyl group. ..
  • the examples of the “unsubstituted alkyl group” and the “substituted alkyl group” listed here are merely examples, and the “substituted alkyl group” described in the present specification includes “unsubstituted alkyl group”.
  • the group in which the "group” has a substituent further has a substituent
  • the group in which the "substituted alkyl group” further has a substituent, and the like are also included.
  • Unsubstituted alkyl group Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, Isobutyl group, s-butyl group, t-butyl group
  • Substituted alkyl group Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, Trifluoromethyl group
  • substituted or unsubstituted alkenyl group (specific example group G4) described in the present specification include the following unsubstituted alkenyl groups and substituted alkenyl groups.
  • 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 the “substituted or unsubstituted alkenyl group”.
  • alkenyl group when simply referred to as “alkenyl group”, it includes both “unsubstituted alkenyl group” and “substituted alkenyl group”.
  • alkenyl group when simply referred to as “alkenyl group”, it includes both “unsubstituted alkenyl group” and “substituted alkenyl group”.
  • the “substituted alkenyl group” is a case where the “unsubstituted alkenyl group” has a substituent, and examples thereof include a group in which the “unsubstituted alkenyl group” has a substituent and a substituted alkenyl group. ..
  • Unsubstituted alkenyl group and substituted alkenyl group Vinyl group, Allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methyl vinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1,2-dimethylallyl group
  • substituted or unsubstituted alkynyl group examples include the following unsubstituted alkynyl groups.
  • the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group” is an "unsubstituted alkynyl group.”
  • alkynyl group when simply referred to as “alkynyl group”, "unsubstituted” And “substituted alkynyl group”.
  • the “substituted alkynyl group” is a case where the “unsubstituted alkynyl group” has a substituent, and examples thereof include a group in which the “unsubstituted alkynyl group” has a substituent.
  • substituted or unsubstituted cycloalkyl group (specific group G6) described in the present specification include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups.
  • the unsubstituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group is the “substituted or unsubstituted cycloalkyl group”.
  • cycloalkyl group means a "substituted cycloalkyl group”.
  • cycloalkyl group both "unsubstituted cycloalkyl group” and “substituted cycloalkyl group” are referred to.
  • Including The “substituted cycloalkyl group” is a case where the “unsubstituted cycloalkyl group” has a substituent, and the following “unsubstituted cycloalkyl group” is a group having a substituent or an example of a substituted cycloalkyl group Etc.
  • Unsubstituted aliphatic ring group Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group
  • Specific examples (specific example group G7) of the group 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)(G3), -Si(G5)(G5)(G5), -Si(G6)(G6)(G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is a "heterocyclic group” described in Specific Example Group G2.
  • G3 is an "alkyl group” described in Specific Example Group G3.
  • G5 is an "alkynyl group” described in Specific Example Group G5.
  • G6 is a "cycloalkyl group” described in Specific Example Group G6.
  • Specific examples of the group represented by —O—(R 904 ) described in the present specification include: -O (G1), -O (G2), -O (G3), -O (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is a "heterocyclic group” described in Specific Example Group G2.
  • G3 is an "alkyl group” described in Specific Example Group G3.
  • G6 is a "cycloalkyl group” described in Specific Example Group G6.
  • Specific examples of the group represented by -S-(R 905 ) described in the present specification include: -S (G1), -S (G2), -S (G3), -S (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is a "heterocyclic group” described in Specific Example Group G2.
  • G3 is an "alkyl group” described in Specific Example Group G3.
  • G6 is a "cycloalkyl group” described in Specific Example Group G6.
  • Specific examples of the group represented by —N(R 906 )(R 907 ) described in the present specification include: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), -N (G6) (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is a "heterocyclic group” described in Specific Example Group G2.
  • G3 is an "alkyl group” described in Specific Example Group G3.
  • G6 is a "cycloalkyl group” described in Specific Example Group G6.
  • halogen atom specifically example group G11
  • halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
  • a specific example of the "alkoxy group” described in the present specification is a group represented by -O(G3), wherein G3 is an "alkyl group” described in the specific example group G3.
  • the carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18 unless otherwise specified in the present specification.
  • a specific example of the “alkylthio group” described in the present specification is a group represented by —S(G3), wherein G3 is the “alkyl group” described in the specific example group G3.
  • the carbon number of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18 unless otherwise specified in the present specification.
  • a specific example of the "aryloxy group” described in the present specification is a group represented by -O(G1), wherein G1 is the “aryl group” described in the specific example group G1.
  • the number of ring-forming carbon atoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.
  • a specific example of the “arylthio group” described in the present specification is a group represented by —S(G1), wherein G1 is the “aryl group” described in the specific example group G1.
  • the ring-forming carbon number of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
  • Specific examples of the "aralkyl group” described in the present specification are groups represented by -(G3)-(G1), wherein G3 is an "alkyl group” described in specific example group G3.
  • G1 are “aryl groups” described in Specific Example Group G1.
  • an "aralkyl group” is an embodiment of a “substituted alkyl group,” substituted with an “aryl group.”
  • the number of carbon atoms of the “unsubstituted aralkyl group” which is the “unsubstituted alkyl group” substituted with the “unsubstituted aryl group” is 7 to 50, preferably 7 unless otherwise specified in the present specification. -30, more preferably 7-18.
  • aralkyl group examples include, for example, benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ -naphthylmethyl group.
  • the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl- group.
  • substituted or unsubstituted heterocyclic group described in the present specification preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenyl group.
  • Nantrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 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)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole- 4-yl group), (9-biphen
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups.
  • X B is an oxygen atom or a sulfur atom.
  • the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group. Group etc.
  • the “substituted or unsubstituted arylene group” described in the present specification means a divalent group of the above “aryl group”.
  • Specific examples of the “substituted or unsubstituted arylene group” include a divalent group of the “aryl group” described in specific example group G1. That is, as a specific example of the “substituted or unsubstituted arylene group” (specific example group G12), a group excluding one hydrogen bonded to the ring-forming carbon of the “aryl group” described in specific example group G1. Is.
  • Specific examples of the “substituted or unsubstituted divalent heterocyclic group” described in the present specification are groups in which the “heterocyclic group” described in specific example group G2 is divalent. Is mentioned. That is, as a specific example of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13), one bonded to the ring-forming atom of the “heterocyclic group” described in specific example group G2 It is a group excluding hydrogen.
  • substituted or unsubstituted alkylene group examples include groups in which the “alkyl group” described in specific group G3 is divalent. That is, as a specific example of the “substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen bonded to carbon forming the alkane structure of the “alkyl group” described in specific example group G3 is It is the removed group.
  • substituted or unsubstituted arylene group described in the present specification is preferably any of the following groups unless otherwise specified in the present specification.
  • R 908 is a substituent.
  • m901 is an integer of 0 to 4, and when m901 is 2 or more, a plurality of R 908 s may be the same as or different from each other.
  • each R 909 independently represents a hydrogen atom or a substituent. Two R 909 may be bonded to each other via a single bond to form a ring.
  • R 910 is a substituent.
  • m902 is an integer of 0 to 6.
  • a plurality of R 910s may be the same as or different from each other.
  • the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any of the following groups, unless otherwise specified in the present specification.
  • R 911 is a hydrogen atom or a substituent.
  • X B is an oxygen atom or a sulfur atom.
  • R 921 to R 930 two adjacent groups that form a pair when “two or more groups adjacent to each other are bonded to each other to form a ring” are R 921 and R 922 , R 922 and R 923 , R 923 and R 924 , R 924 and R 930 , R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R. 929 and R 921 .
  • one or more pairs means that two adjacent two or more pairs may simultaneously form a ring.
  • R 921 and R 922 are bonded to each other to form ring A and at the same time R 925 and R 926 are bonded to each other to form ring B, they are represented by the following formula (XY-81). ..
  • R 921 and R 922 are bonded to each other to form a ring A
  • R 922 and R 923 are bonded to each other to form a ring C.
  • the ring A and the ring C sharing R 922 which are fused to the anthracene mother skeleton by three adjacent R 921 to R 923 , are represented by the following formula (XY-82).
  • Rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.
  • “Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle.
  • the “saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocycle.
  • the ring A formed by combining R 921 and R 922 with each other in the above formula (XY-81) is a carbon atom of the anthracene skeleton to which R 921 binds and a carbon atom of the anthracene skeleton to which R 922 binds. It means a ring formed by an atom and one or more arbitrary elements.
  • R 921 and R 922 form a ring A
  • a carbon atom of the anthracene skeleton to which R 921 binds a carbon atom of the anthracene skeleton to which R 922 binds
  • four carbon atoms When forming a saturated ring, the ring formed by R 921 and R 922 is a benzene ring. Moreover, when forming a saturated ring, it becomes a cyclohexane ring.
  • the "arbitrary element” is preferably a C element, an N element, an O element, or an S element.
  • a bond that does not participate in ring formation may be terminated with a hydrogen atom or the like, or may be substituted with any substituent.
  • the ring formed is a heterocycle.
  • the “one or more arbitrary elements” forming the saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less. ..
  • aromatic hydrocarbon ring examples include structures in which the aryl group mentioned as a specific example in the specific example group G1 is terminated by a hydrogen atom.
  • aromatic heterocycle examples include a structure in which the aromatic heterocyclic group mentioned as a specific example in the specific example group G2 is terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the cycloalkyl group mentioned as a specific example in the specific example group G6 is terminated by a hydrogen atom.
  • the substituent is, for example, an “arbitrary substituent” described later.
  • specific examples of the substituent are the substituents described in the above-mentioned “Substituents”.
  • the substituent in the case of “substituted or unsubstituted” (hereinafter, may be referred to as “optional substituent”) is An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ) (here, R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50
  • each of the two or more R 901 to R 907 may be the same or different.
  • Halogen atom cyano group, nitro group
  • It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the substituent in the case of “substituted or unsubstituted” is An alkyl group having 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the case of “substituted or unsubstituted” is An alkyl group having 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5-membered ring or 6-membered ring, and Preferably, a benzene ring) may be formed.
  • any substituent may further have a substituent. Examples of the substituent which the optional substituent further has are the same as the above-mentioned optional substituents.
  • the organic EL element of the first aspect of the present invention is a cathode, an anode, an organic electroluminescence element having an organic layer between the cathode and the anode,
  • the organic layer is a compound represented by the following formula (1) and a compound represented by the following formulas (11-1) and (11-3), or the following formulas (11-2) and (11-3)
  • a compound A hereinafter, sometimes referred to as a compound represented by the formula (11)
  • a compound represented by the formula (11) which is a compound represented by.
  • the organic EL device 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, a light emitting layer 5 and a cathode 10. And an organic layer 6 between them.
  • the compound represented by the above formula (1) and the compound A are contained in the organic layers 4 to 6 between the anode 3 and the cathode 10, and preferably in the light emitting layer 5.
  • the compound represented by the above formula (1) and the compound A contained in the above organic layer may each be one kind alone or two or more kinds.
  • R 1 to R 8 is —L 13 —Ar 13 . That is, the anthracene compound of the formula (1) has a structure in which three or more groups -L X -Ar X (X is 11, 12 or 13) are substituted.
  • the compound represented by the formula (1) may be referred to as “3-substituted anthracene compound (1)” or “3-substituted anthracene-based host material (1)”.
  • Conventional anthracene-based host materials having two substituents corresponding to the above group -L X -Ar X are known.
  • disubstituted anthracene compound (Hereinafter, this may be referred to as a "disubstituted anthracene compound”.)
  • the present inventors have found that when the 3-substituted anthracene compound (1) is used as the host material of the light emitting layer and the compound A is used as the dopant material, the driving voltage is lowered and the device life is improved.
  • the present inventors also examined a combination with a tri-substituted anthracene-based host material (1) and a material forming a layer adjacent to the light emitting layer containing the compound A.
  • the compound represented by the formula (20) or the formula (21) described below hereinafter may be referred to as an azine-based hole blocking layer material (21)) or the formula ( It was found that the use of the compound represented by 31) (hereinafter sometimes referred to as the fluoranthene-based hole blocking layer material (31)) provides a more excellent effect of improving the device life.
  • the compound represented by the formula (41) (hereinafter, may be referred to as “monoamine-based electron blocking layer material (41)”) or the formula (51). It was also found that an organic EL device having a longer life can be obtained by using the compound described above, and the present invention has been completed.
  • the organic EL element of the second aspect of the present invention is an organic EL element in which the compound represented by the formula (1) and the compound A are contained in the light emitting layer, which is one embodiment of the organic EL element of the first aspect.
  • the organic layer further comprises a hole blocking layer adjacent to the light emitting layer,
  • the hole blocking layer is characterized by containing one or more compounds selected from compounds represented by the following formulas (20), (21) and (31).
  • the organic EL element 1a 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, a light emitting layer 5 and a cathode 10. And a hole blocking layer 6a adjacent to the light emitting layer 5 among the organic layers 6 between the light emitting layer 5 and the cathode 10.
  • the compounds represented by the formulas (20), (21) and (31) contained in the hole blocking layer may be one kind alone, or two or more kinds.
  • the organic EL device of the third aspect of the present invention is an organic EL device in which the compound represented by the above formula (1) and the compound A are contained in the light emitting layer, which is one embodiment of the organic EL device of the first aspect.
  • the organic layer further includes an electron blocking layer adjacent to the light emitting layer,
  • the electron blocking layer contains a compound represented by the following formula (41) or a compound represented by the following formula (51).
  • the organic EL element 1b 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, a light emitting layer 5 and a cathode 10.
  • 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, a light emitting layer 5 and a cathode 10.
  • an electron blocking layer 4b adjacent to the light emitting layer 5 among the organic layers 4 between the anode 3 and the light emitting layer 5.
  • the compound represented by the formula (41) and the compound represented by the formula (51) contained in the electron blocking layer may each be a single type or may be two or more types. ..
  • the organic EL device according to the first aspect is an organic EL device in which the compound represented by the formula (1) and the compound A are contained in the light emitting layer.
  • the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, The hole blocking layer contains one or more compounds selected from the compounds represented by the above formulas (20), (21) and (31),
  • the organic layer further includes an electron blocking layer adjacent to the light emitting layer, The electron blocking layer contains a compound represented by the above formula (41) or a compound represented by the above formula (51).
  • An organic EL element 1c of a fourth aspect which is one embodiment of the organic EL elements of the first to third aspects, has a substrate 2, an anode 3, a light emitting layer 5, a cathode 10, an anode 3 and a light emitting layer.
  • the organic layer includes the light emitting layer 5, the hole blocking layer 6a, and the electron blocking layer 4b, and when each layer contains a specific compound, the effect of improving the device life can be obtained.
  • the organic EL element according to the fifth aspect of the present invention has a so-called tandem type structure having two or more light emitting layers. By having such a tandem structure, a white light emitting element having a simple structure can be manufactured.
  • the organic EL element according to one aspect of the present invention may be, for example, a fluorescent or phosphorescent type monochromatic light emitting element, or a fluorescent/phosphorescent hybrid type white light emitting element. Further, it may be a simple type having a single light emitting unit or a tandem type having a plurality of light emitting units.
  • the “light emitting unit” refers to a minimum unit that includes an organic layer, at least one of the organic layers is a light emitting layer, and emits light by recombination of injected holes and electrons.
  • the “light emitting layer” described in the present specification is an organic layer having a light emitting function.
  • the light emitting layer is, for example, a phosphorescent light emitting layer, a fluorescent light emitting layer, or the like, and may be a single layer or a plurality of layers.
  • the light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers or fluorescent light emitting layers. In this case, for example, a space layer for preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. May be provided between each light emitting layer.
  • Examples of the simple type organic EL element include element configurations such as anode/light emitting unit/cathode. A typical layer structure of the light emitting unit is shown below. Layers in parentheses are optional.
  • A (hole injection layer/) hole transport layer/fluorescent emission layer (/electron transport layer/electron injection layer)
  • B (hole injection layer/) hole transport layer/phosphorescence emitting layer (/electron transport layer/electron injection layer)
  • C) hole injection layer/) hole transport layer/first fluorescent light emitting layer/second fluorescent light emitting layer (/electron transport layer/electron injection layer)
  • D (hole injection layer/) hole transport layer/first phosphorescent light emitting layer/second phosphorescent light emitting layer (/electron transport layer/electron injection layer)
  • e (hole injection layer/)hole transport layer /Phosphorescent layer/Space layer/Fluorescent layer (/Electron transport layer/Electron injection layer)
  • F (hole injection layer
  • the layer structure of the organic EL element according to one embodiment of the present invention is not limited to these.
  • the hole injection layer is provided between the hole transport layer and the anode.
  • the organic EL element has an electron injection layer and an electron transport layer, it is preferable that the electron injection layer is provided between the electron transport layer and the cathode.
  • each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer or may be composed of a plurality of layers.
  • the plurality of phosphorescent light emitting layers, and the phosphorescent light emitting layer and the fluorescent light emitting layer may be light emitting layers of mutually different colors.
  • the light emitting unit (f) includes a hole transport layer/first phosphorescent light emitting layer (red light emission)/second phosphorescent light emitting layer (green light emission)/space layer/fluorescent light emitting layer (blue light emission)/electron transport layer. You can also do it.
  • An electron blocking layer may be provided between each light emitting layer and the hole transport layer or the space layer. Further, a hole blocking layer may be provided between each light emitting layer and the electron transport layer.
  • an element structure such as anode/first light emitting unit/intermediate layer/second light emitting unit/cathode can be mentioned.
  • the first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units, for example.
  • the intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, a connector layer, or an intermediate insulation layer.
  • the intermediate layer is a layer that supplies electrons to the first light emitting unit and holes to the second light emitting unit, and can be formed of a known material.
  • the organic EL element 1d according to the fifth aspect of the present invention shown in FIG. 5 has a substrate 2, an anode 3, a cathode 10, and an organic layer between the anode 3 and the cathode 10.
  • the organic layer includes a first light emitting unit 5A, a second light emitting unit 5B between the first light emitting unit 5A and the cathode 10, and an organic layer between the anode 3 and the first light emitting unit 5A. It has a layer 4a and an organic layer 6b between the second light emitting unit 5B and the cathode 10.
  • the charge generation layer 8 is provided between the first light emitting unit 5A and the second light emitting unit 5B.
  • the compounds represented by formulas (1), (11), (20), (21), (31), (41) and (51) will be described.
  • the compound represented by the following formula (1) is contained in the organic layer. It is preferably contained in the light emitting layer.
  • R 1 to R 8 is —L 13 —Ar 13 .
  • L 11 to L 13 are each independently Single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms. When two or more L 13's are present, the two or more L 13 's may be the same as or different from each other.
  • Ar 11 to Ar 13 are each independently It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • R 1 to R 8 which are not —L 13 —Ar 13 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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 1 to R 8 that are not —L 13 —Ar 13 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), It is a halogen atom, a cyano group, or a nitro group.
  • R 1 to R 8 which are not -L 11 -Ar 11 , -L 12 -Ar 12 , -L 13 -Ar 13 and -L 13 -Ar 13 are bonded to each other to form an anthracene ring. Does not form.
  • L 11 to L 13 in formula (1) are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  • L 11 to L 13 in the formula (1) are each independently a single bond, or a substituted or unsubstituted phenylene group, A substituted or unsubstituted biphenylene group, A substituted or unsubstituted terphenylene group, It is a group selected from the group consisting of a substituted or unsubstituted quarter phenylene group and a substituted or unsubstituted naphthylene group.
  • Ar 11 to Ar 13 in the formula (1) are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • Ar 11 to Ar 13 in the formula (1) are each independently A substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group, A substituted or unsubstituted fluorenyl group, A substituted or unsubstituted 9,9′-spirobifluorenyl group, A substituted or unsubstituted benzofluorenyl group, A group consisting of a substituted or unsubstituted phenanthryl group and a substituted or unsubstituted benzophenanthryl group is further selected.
  • At least one of Ar 11 to Ar 13 in the above formula (1) is independently a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms. ..
  • the group represented by -L 13 -Ar 13 in the above formula (1) is A substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group, A substituted or unsubstituted biphenyl group, A substituted or unsubstituted phenanthrenyl group, A substituted or unsubstituted benzophenanthrenyl group, A substituted or unsubstituted fluorenyl group, A substituted or unsubstituted benzofluorenyl group, A substituted or unsubstituted dibenzofuranyl group, A substituted or unsubstituted naphthobenzofuranyl group, It is selected from the group consisting of a substituted or unsubstituted dibenzothiophenyl group and a substituted or unsubstituted carbazolyl group.
  • the compound represented by the formula (1) is a compound represented by the following formula (1-1).
  • the compound represented by the formula (1) is a compound represented by the following formula (1-1H).
  • the compound represented by the above formula (1) is selected from the group consisting of compounds represented by the following formulas (1-2) to (1-4).
  • L 11 , L 12 , Ar 11 , Ar 12 , R 1 and R 3 to R 8 are as defined in the formula (1).
  • R 1 to R 8 other than —L 13 —Ar 13 in the above formula (1) are hydrogen atoms.
  • Compound represented by Formula (11) (Compound A)
  • the compound A is a compound represented by the following formulas (11-1) and (11-3), or a compound represented by the following formulas (11-2) and (11-3).
  • Compound A is contained in the organic layer. It is preferably contained in the light emitting layer.
  • Ring A is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms, or a benzene ring represented by the following formula (X).
  • X a benzene ring represented by the following formula (X).
  • One of the two ring-forming carbon atoms represented by * is bonded to * extending from the benzene ring B of the formula (11-1) or (11-2), and the other benzene of the formula (11-3). Bond with a single bond extending from ring C.
  • the two * in the formula (11-1) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
  • the three *'s in the formula (11-2) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
  • R 101 to R 116 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
  • R 101 to R 116 and R 117 that do not form a ring are each independently Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S-
  • R 901 to R 909 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • n is an integer of 1 or 2.
  • n is 2, the two R 117 may be the same or different.
  • the fused aryl ring is a ring in which a plurality of aromatic rings are fused.
  • the condensed heterocycle is a ring in which a plurality of heterocycles are condensed or a ring in which a heterocycle and an aromatic ring are condensed. ..
  • the “fused aryl ring” of ring A has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned “aryl group”. Specific examples include compounds in which a hydrogen atom is introduced into the "aryl group” described in Specific Example Group G1.
  • the “fused heterocycle” of ring A has the same structure as the above-mentioned “heterocyclic group” having a condensed ring structure and a hydrogen atom introduced therein. Specific examples thereof include compounds in which a hydrogen atom has been introduced into those having a condensed ring structure among the “heterocyclic groups” described in Specific Example Group G2.
  • “*” (asterisk) in the formula (11-1) is bonded to the ring A in the formula (11-3).
  • formula (11-1) there are two “*”, and each of the two “*” is a ring-forming carbon atom of the condensed aryl ring of ring A, a ring-forming atom of the condensed heterocycle, or the formula ( The compound is bonded to the ring-forming carbon atom of the benzene ring represented by 2).
  • the “*” (asterisk) in formula (11-2) is also bonded to ring A in formula (11-3).
  • each of the three “*” is a ring-forming carbon atom of the condensed aryl ring of ring A, a ring-forming atom of the condensed heterocycle, or the formula ( The compound is bonded to the ring-forming carbon atom of the benzene ring represented by X).
  • "*" (asterisk) in the formula (X) indicates a bonding position.
  • * extending from the benzene ring B of the formula (11-1) or (11-2) is bonded, and on the other side, extending from the benzene ring C of the formula (11-3). Combine with a single bond.
  • a haloalkyl group is a group in which one or more hydrogens of the “alkyl group” described in specific example group G3 are substituted with a halogen atom.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is a "heterocyclic group” described in Specific Example Group G2.
  • G3 is an "alkyl group” described in Specific Example Group G3.
  • G6 is a "cycloalkyl group” described in Specific Example Group G6.
  • —COO(R 909 ) Specific examples include: -COO (G1) -COO (G2) -COO (G3) -COO (G6) Is mentioned.
  • the compounds represented by the formulas (11-1) and (11-3) or the compounds represented by the formulas (11-2) and (11-3) are represented by the following formula (13), It is a compound represented by formula (14) or formula (15).
  • Ring A′ is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms.
  • R 101 to R 107 and R 110 to R 117 are as defined in the formula (11-1), the formula (11-2), the formula (11-3) and the formula (X). )
  • the substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms of the ring A of the formula (11-3) and the ring A′ of the formula (15) is a substituted or unsubstituted naphthalene ring. Or a substituted or unsubstituted fluorene ring.
  • the substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms of the ring A of the formula (11-3) and the ring A′ of the formula (15) is a substituted or unsubstituted dibenzofuran ring.
  • the compounds represented by the formulas (11-1) and (11-3) or the compounds represented by the formulas (11-2) and (11-3) have the following formula (16-1): ) To a compound represented by the formula (16-5).
  • R 101 to R 117 are as defined in the formula (11-1), the formula (11-2), the formula (11-3) and the formula (X).
  • X is O, NR 125 , or C(R 126 )(R 127 ).
  • R 121 to R 127 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
  • the compound A is a compound represented by the formula (13).
  • R 105 and R 114 in the formula (13) are each independently —N(R 906 )(R 907 )(R 901 to R 907 are as defined in the above formula (1)). ..
  • the organic layer comprises a light emitting layer
  • the light emitting layer contains the compound represented by the formula (1) and the compound A.
  • the compound represented by the formula (1) functions as a host material of the light emitting layer
  • the compound A functions as a dopant material of the light emitting layer.
  • Compound A can be synthesized, for example, by following known reactions in Examples described later and using known alternative reactions or starting materials according to the intended product.
  • the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, the hole blocking layer selected from compounds represented by formulas (20), (21) and (31). Or more than one compound.
  • the “hole blocking layer” is a layer provided between the light emitting layer and the electron transporting layer for the purpose of preventing holes from leaking from the light emitting layer to the electron transporting layer.
  • the layer also has a function as an electron transport layer that transports injected electrons to the light emitting layer.
  • X 21 represents an oxygen atom, a sulfur atom or a selenium atom.
  • L 21 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 21 , Ar 22 and Ar 23 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. Is. Ar 21 and Ar 22 may combine with each other to form a ring.
  • n21 is an integer of 1 to 3.
  • examples of the structure represented by the formula (20) include the following structures.
  • the compound represented by formula (20) is a compound represented by formula (20-1) below.
  • L 21 , X 21 , Ar 21 , Ar 22 and Ar 23 are as defined in the formula (20).
  • the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, the hole blocking layer selected from compounds represented by formulas (20), (21) and (31). Or more than one compound.
  • X 1 to X 3 are each independently N or CR b . However, at least one of X 1 to X 3 is N.
  • R b is Hydrogen atom, Halogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • R b does not form a ring by combining with R 21 to R 23 which are adjacent to each other.
  • R 21 to R 23 are each independently -(L 2 ) m -(Ar 2 ) n , Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • L 2 is A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • m is an integer of 0 to 2. When m is 0, L 2 is a single bond. When m is 2, two L 2's may be the same or different.
  • Ar 2 is It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • n is an integer of 1 or 2 and when n is 2, two Ar 2 may be the same or different from each other. However, when n is 2, m is 1 or more. ]
  • two of X 1 to X 3 in the above formula (21) are N. That is, the central skeleton is a pyrimidine ring.
  • R 21 to R 23 in the formula (21) are each independently A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • the compound represented by the above formula (21) is a compound represented by the following formula (21-1).
  • R 21 , R 22 and X 3 are as defined in the formula (21). Two or more adjacent groups of R 51 to R 55 are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or Do not form.
  • R 51 to R 55 which do not form a ring are each independently Hydrogen atom, An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  • the compound represented by the formula (21-1) is a compound represented by the following formula (21-2).
  • R 22 , X 3 and R 51 to R 55 are as defined in the above formula (21-1).
  • R 56 to R 60 are each independently Hydrogen atom, An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  • the compound represented by the formula (21-2) is a compound represented by the following formula (21-3).
  • R 22 , X 3 and R 56 to R 60 are as defined in the formula (21-2).
  • Y 1a to Y 8a are each independently CR 61a or N.
  • Y 1b to Y 8b are each independently CR 61b or N.
  • X 4a is O, S or NR 61a .
  • X 4b is O, S or NR 61b .
  • Two or more sets of two or more R 61a substituting adjacent atoms are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring-forming atoms, or Does not form a ring.
  • R 61a is a single bond which is bonded to *1, or two or more one or more groups of R 61a substituting the adjacent atoms are bonded to each other to form a ring-forming atom.
  • R 61b is a single bond that is bonded to *2, or one of the atoms constituting the ring formed by two or more sets of two or more R 61b substituting the adjacent atoms is bonded to each other; , And to *2 via a single bond.
  • R 61a and R 61b which do not form the ring and which are not a single bond that binds to *1 or *2 are each independently, Hydrogen atom, An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • R 61a there are a plurality a plurality of R 61a may be the same or may be different from one another. If R 61b there are a plurality, the plurality of R 61b may be the same or may be different from one another. ]
  • “one of the atoms constituting the ring formed by bonding two or more sets of two or more R 61a substituting to the adjacent atoms to each other is bonded to a carbon atom of a benzene ring through a single bond.
  • specific examples of the group composed of X 4a and Y 1a to Y 8a include the followings.
  • the compound represented by the formula (21) is a compound represented by the following formula (21-4).
  • X 1 to X 3 , R 21 , R 22 , L 2 , m and n are as defined in the formula (21).
  • Y 1 to Y 8 are each independently CR 61e or N.
  • X 4 is O, S or NR 61e .
  • R 61e is each independently Hydrogen atom, An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • each of the two or more R 901 to R 907 may be the same or different. If R 61e there are a plurality, the plurality of R 61e may be the same or may be different from one another.
  • R 61e Two or more sets of two or more R 61e substituting adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or a ring. Does not form. However, one of R 61e is a single bond that is bonded to *3, or one or more groups of two or more of R 61e substituting the adjacent atoms are bonded to each other to form a ring. One binds to *3 via a single bond. ]
  • the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, the hole blocking layer selected from compounds represented by formulas (20), (21) and (31). Or more than one compound.
  • At least one of R 31 to R 40 is —(L 3 ) p —Ar 3 .
  • L 3 is A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • p is an integer of 0 to 3. When p is 0, L 3 is a single bond. When p is 2 or more, the plurality of L 3 may be the same as or different from each other.
  • Ar 3 is It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • - (L 3) p R 31 ⁇ R 36 is not a -Ar 3
  • - (L 3) p -Ar 3 1 or more sets of two or more adjacent to each other of R 37 ⁇ R 40 are not in each other They combine to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or no ring.
  • R 31 to R 40 not involved in the ring formation are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  • p in the above formula (31) is preferably 0 or 1.
  • the compound represented by the formula (31) is a compound represented by the following formula (31-1).
  • the compound represented by the above formula (31) is a compound represented by the following formula (31-1H).
  • the organic layer further includes an electron blocking layer adjacent to the light emitting layer, and the electron blocking layer contains a compound represented by the following formula (41).
  • the “electron blocking layer” is a layer provided between the light emitting layer and the hole transporting layer for the purpose of preventing electrons from leaking from the light emitting layer to the hole transporting layer.
  • the layer also has a function as a hole transport layer that transports the injected holes to the light emitting layer.
  • L 41 to L 43 are each independently Single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 41 to Ar 43 are each independently A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the compound represented by the formula (41) is a compound represented by the following formula (41-1).
  • Ar 41 to Ar 43 and L 41 are as defined in the formula (41).
  • Ar 42 and Ar 43 are bonded to any carbon atom constituting the phenyl group which they respectively substitute.
  • the compound represented by the above formula (41) is a compound represented by the following formula (41-2).
  • Ar 41 and L 41 are as defined in the above formula (41).
  • X 5 and X 6 are each independently O, S or N(R 906 ).
  • R 906 is Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two R 906 are present, the two R 906 may be the same or different.
  • One of the carbon atoms constituting the benzene ring of one of the monovalent heterocyclic groups containing X 5 or X 6 is bonded to any of the carbon atoms constituting the phenyl group substituted on the central nitrogen atom.
  • the compound represented by the formula (41) is a compound represented by the following formula (41-3).
  • Ar 41 , Ar 42, and L 41 to L 43 are as defined in the formula (41).
  • X 7 is O, S or NR 89 .
  • Two or more sets of two or more of R 81 to R 89 which substitute the adjacent atom are bonded to each other to form a substituted or unsubstituted ring-forming saturated or unsaturated ring having 3 to 30 ring-forming atoms. Or does not form the ring.
  • one of R 81 to R 89 is a single bond that bonds to *6, or two or more sets of R 81 to R 89 which substitute the adjacent atoms are bonded to each other.
  • One of the atoms constituting the ring formed is bonded to *6 via a single bond.
  • R 81 to R 89 which do not form a ring and are not a single bond that binds to *6, are each independently Hydrogen atom, An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  • the organic layer further includes an electron blocking layer adjacent to the light emitting layer, and the electron blocking layer contains a compound represented by the following formula (51).
  • At least one pair of two or more of R 62 to R 70 substituting adjacent atoms is bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring-forming atoms; , Or does not form the ring.
  • Two or more sets of two or more of R 71 to R 79 which are substituted on adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms. , Or does not form the ring.
  • R 62 to R 70 is a single bond that bonds to *4, or two or more pairs of R 62 to R 70 which substitute the adjacent atom are bonded to each other.
  • One of the atoms constituting the ring formed is bonded to *4 via a single bond.
  • One of R 71 to R 79 is a single bond that binds to *5, or two or more pairs of R 71 to R 79 which substitute the adjacent atom are formed by bonding to each other;
  • One of the atoms constituting the ring is bonded to *5 via a single bond.
  • R 71 to R 79 that does not bond to *5 is a single bond that bonds to L 52 , or one or more pairs of two or more of R 71 to R 79 that substitute for the adjacent atom are Another one of the atoms constituting the ring formed by bonding to each other is bonded to L 52 via a single bond.
  • R 62 to R 79 which do not form a ring and which are not a single bond to bond with *4 or *5 are each independently Hydrogen atom, An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • L 51 is, independently of each other, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • q is an integer of 0 to 3. When q is 2 or more, R 62 to R 70 existing in two or more may be the same or different from each other. However, when q is 0, it is a hydrogen atom terminating L 51 .
  • r is an integer of 0 to 2. When r is 0, L 51 is a single bond. When r is 2, two L 51 's may be the same or different from each other. However, when q is 2 or more, r is 1 or 2.
  • L 52 is Single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • Ar 52 is It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the compound represented by the formula (51) is a compound represented by the following formula (51-1).
  • R 62 to R 70 , R 72 to R 79 , *4, *5, q, L 51 , r, L 52, and Ar 52 are as defined in the formula (51). Is. ]
  • q in the above formula (51) is 1.
  • the compound represented by the above formula (51) is a compound represented by the following formula (51-2).
  • R 62 , L 51 , r, L 52, and Ar 52 are as defined in the formula (51). ]
  • the compound represented by the above formula (51) is selected from the group consisting of compounds represented by the following formulas (51-3a) to (51-3c).
  • R 62 , L 51 , r, L 52, and Ar 52 are as defined in the formula (51). ]
  • the "substituted or unsubstituted" In that case, the substituent is An unsubstituted alkyl group having 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, An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ) (here, R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloal
  • each of the two or more R 901 to R 907 may be the same or different.
  • Halogen atom cyano group, nitro group
  • It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • the "substituted or unsubstituted" In that case, the substituent is An alkyl group having 1 to 50 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
  • the "substituted or unsubstituted" In that case, the substituent is An alkyl group having 1 to 18 carbon atoms, It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
  • the organic EL element of the first aspect has a cathode, an anode, and an organic layer between the cathode and the anode, and the organic layer is represented by the formula (1).
  • the organic EL device of the second aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer includes a light emitting layer, and the light emitting layer is the 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 compound represented by 21) and one or more compounds represented by the formula (31) are included.
  • the organic EL device of the third aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer includes a light emitting layer, and the light emitting layer is the A compound containing a compound represented by the formula (1) and a compound represented by the formula (11), wherein the electron blocking layer adjacent to the light emitting layer is represented by the formula (41), or a compound represented by the following formula (41) Other than the compound represented by 51), conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.
  • the organic EL element of the fourth aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer includes a light emitting layer, and the light emitting layer is the 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 compound represented by the formula (1) is included.
  • the organic EL element of the fifth aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including two or more light emitting layers, and As long as one or more of the above light emitting layers contains a compound represented by the formula (1) and a compound represented by the formula (11), it is a conventionally known substance unless the effects of the present invention are impaired.
  • the materials and element configurations of can be applied.
  • the substrate is used as a support for the light emitting device.
  • the substrate for example, glass, quartz, plastic or the like can be used.
  • a flexible substrate may be used.
  • the flexible substrate is a flexible (flexible) substrate, and examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
  • a metal for example, indium oxide-tin oxide (ITO: indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide.
  • ITO indium oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide tungsten oxide
  • indium oxide containing zinc oxide Graphene and the like.
  • gold (Au), platinum (Pt), or a nitride of a metal material for example, titanium nitride
  • the hole-injection layer is a layer containing a substance having a high hole-injection property.
  • a substance having a high hole injecting property molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, an aromatic amine compound, or a high molecular compound (oligomer, dendrimer, polymer, etc.) can also be used.
  • the hole-transporting layer is a layer containing a substance having a high hole-transporting property.
  • An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer.
  • a high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • a substance other than these substances may be used as long as it has a property of transporting more holes than electrons.
  • the layer containing a substance having a high hole-transporting property is not limited to a single layer and may be a stack of two or more layers containing any of the above substances.
  • the light emitting layer is a layer containing a substance having a high light emitting property, and various materials can be used.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the substance having a high light emitting property.
  • 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.
  • blue fluorescent material that can be used in the light emitting layer
  • pyrene derivative, styrylamine derivative, chrysene derivative, fluoranthene derivative, fluorene derivative, diamine derivative, triarylamine derivative and the like can be used.
  • An aromatic amine derivative or the like can be used as a green fluorescent material that can be used in the light emitting layer.
  • a tetracene derivative, a diamine derivative, or the like can be used as a red fluorescent light emitting material that can be used in the light emitting layer.
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used as a blue phosphorescent material that can be used for the light emitting layer.
  • An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used as a red phosphorescent light emitting material that can be used for the light emitting layer.
  • the light-emitting layer may have a structure in which the above-described substance having a high light-emitting property (guest material) is dispersed in another substance (host material).
  • guest material substance having a high light-emitting property
  • host material another substance having a high light emitting property
  • various substances can be used, the lowest unoccupied orbital level (LUMO level) is higher than that of a substance having a high light emitting property, and the highest occupied orbital level ( It is preferable to use a substance having a low HOMO level).
  • a substance (host material) for dispersing a substance having a high light-emitting property 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, etc.
  • the electron-transporting layer is a layer containing a substance having a high electron-transporting property.
  • a metal complex such as an aluminum complex, a beryllium complex or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative or a phenanthroline derivative
  • 3) a polymer compound can be used.
  • the compound represented by the formula (61) is preferable.
  • X 61 to X 68 are each independently a carbon atom bonded to the group represented by formula (B), N or CR 61 . At least one of X 61 to X 68 is a carbon atom bonded to the group represented by formula (B).
  • R 61 is Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-( R904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • R 901 to R 907 are each independently Hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • each of the two or more R 901 to R 907 may be the same or different.
  • L 61 is A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
  • c is an integer of 0-8. When c is 0, L 61 is a single bond. When c is 2 or more, the two or more L 61 may be the same as or different from each other.
  • B 61 is It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
  • b is an integer of 1 to 5, and when b is 2 or more, B 61 of 2 or more may be the same as or different from each other.
  • the electron-injection layer is a layer containing a substance having a high electron-injection property.
  • the electron injection layer lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc.
  • the metal complex compound, alkali metal such as lithium oxide (LiO x ), alkaline earth metal, or a compound thereof can be used.
  • cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less).
  • 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), and magnesium (Mg), calcium ( Ca), alkaline earth metals such as strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
  • each layer is not particularly limited.
  • a conventionally known forming method such as a vacuum vapor deposition method and 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) or a solvent-dissolved solution dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like.
  • MBE method molecular beam vapor deposition method
  • solvent-dissolved solution dipping method a spin coating method
  • a casting method a bar coating method, a roll coating method, or the like.
  • the film thickness of each layer is not particularly limited, but in general, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and improve the luminous efficiency, it is usually several nm to 1 ⁇ m. A range is preferred.
  • An electronic apparatus is characterized by including the organic electroluminescence element according to any of the first to fifth aspects.
  • the electronic device include a display component such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, and a light-emitting device such as lighting or a vehicle lamp.
  • the compound ET-2 is a compound represented by the formula (61).
  • Example 1 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm. The glass substrate with a transparent electrode after cleaning was mounted on a substrate holder of a vacuum vapor deposition apparatus, and compound HI-1 was vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, and the film thickness was 5 nm. HI-1 film was formed. This HI-1 film functions as a hole injection layer.
  • compound HT-2 was vapor-deposited to form an HT-2 film having a film thickness of 80 nm on the HI-1 film.
  • This HT-2 film functions as a hole transport layer (first hole transport layer).
  • the compound EBL-2 was vapor-deposited to form an EBL-2 film having a film thickness of 10 nm on the HT-2 film.
  • This EBL-2 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH-4 (host material) and compound BD-1 (dopant material) were co-evaporated on the EBL-2 film so that the ratio of compound BD-1 was 2% by mass, and BH-1 having a film thickness of 25 nm: A BD-1 film was formed.
  • This BH-4:BD-1 film functions as a light emitting layer.
  • Compound HBL-1 was vapor-deposited on this light emitting layer to form a 10 nm thick HBL-1 film.
  • This HBL-1 film functions as a first electron transport layer.
  • Compounds ET-2 and Li were co-evaporated on the HBL-1 film so that the ratio of Li was 4% by mass to form an ET-2:Li film having a film thickness of 15 nm.
  • This ET-2:Li film functions as a second electron transport layer.
  • LiF was vapor-deposited on this ET-1 film to form a LiF film having a film thickness of 1 nm.
  • Metal Al was vapor-deposited on this ET-2:Li film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.
  • the layer structure of the obtained organic EL device is as follows. ITO(130)/HI-1(5)/HT-2(80)/EBL-2(10)/BH-4:BD-1(25:2% by mass)/HBL-1(10)/ET- 2: Li(15:4%)/Al(80)
  • the numbers in parentheses represent the film thickness (unit: nm).
  • Examples 2-5 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in Table 1 were used in the dopant material, the host material and the first electron transport layer. The results are shown in Table 1.
  • Example 6 (Production of organic EL element) The process up to the HI-1 film was the same as in Example 1. Following formation of this HI-1 film, compound HT-1 was vapor-deposited to form an HT-1 film having a film thickness of 80 nm on the HI-1 film. This HT-1 film functions as a hole transport layer (first hole transport layer). Following formation of the HT-1 film, the compound EBL-1 was vapor-deposited to form an EBL-1 film having a film thickness of 10 nm on the HT-1 film. This EBL-1 film functions as an electron blocking layer (second hole transport layer).
  • Compound BH-1 (host material) and compound BD-2 (dopant material) were co-evaporated on the EBL-1 film so that the ratio of compound BD-2 was 2% by mass, and BH-1 having a film thickness of 25 nm: A BD-2 film was formed.
  • This BH-1:BD-2 film functions as a light emitting layer.
  • a compound HBL-3 was vapor-deposited on this light emitting layer to form an HBL-3 film having a film thickness of 10 nm.
  • This HBL-3 film functions as a first electron transport layer.
  • Compound ET-1 was vapor-deposited on this HBL-3 film to form an ET-1 film having a film thickness of 15 nm.
  • This ET-1 film functions as a second electron transport layer.
  • LiF was vapor-deposited on this ET-1 film to form a LiF film having a film thickness of 1 nm.
  • Metal Al was vapor-deposited on this LiF film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.
  • the layer structure of the obtained organic EL device is as follows. ITO(130)/HI-1(5)/HT-1(80)/EBL-1(10)/BH-1:BD-2(25:2% by mass)/HBL-3(10)/ET- 1(15)/LiF(1)/Al(80) The numbers in parentheses represent the film thickness (unit: nm).
  • the obtained organic EL device was evaluated by the same method as in Example 1. The results are shown in Table 2.
  • Examples 7, 8 and Comparative Example 1 An organic EL device was prepared and evaluated in the same manner as in Example 6 except that the compounds shown in Table 2 were used instead of the compound BH-1. The results are shown in Table 2.
  • Example 9 An organic EL device was produced in the same manner as in Example 6 except that the compound HBL-1 used in Example 6 was used instead of the compound HBL-3 used in Example 6 using the dopant materials and host materials shown in Table 3 below.
  • the layer structure of the obtained organic EL device is as follows. ITO(130)/HI-1(5)/HT-1(80)/EBL-1(10)/BH-7:BD-1(25:2% by mass)/HBL-1(10)/ET- 1(15)/LiF(1)/Al(80)
  • the numbers in parentheses represent the film thickness (unit: nm).
  • the obtained organic EL device was evaluated by the same method as in Example 6. The results are shown in Table 3.
  • Example 10 An organic EL device was prepared and evaluated in the same manner as in Example 9 except that the compounds shown in Table 3 were used instead of the compound BH-7. The results are shown in Table 3.
  • Example 11 An organic EL device was prepared and evaluated in the same manner as in Example 9 except that BD-3 was used instead of the dopant material BD-1 and the host materials shown in Table 4 below were used. The results are shown in Table 4.
  • Examples 12 to 15 An organic EL device was prepared and evaluated in the same manner as in Example 11 except that the host materials shown in Table 4 were used. The results are shown in Table 4.
  • Example 16 Using the dopant materials and host materials shown in Table 5, except that the compound HT-2 used in Example 6 was replaced with the compound HT-2, and the compound EBL-2 was replaced with the compound HT-2.
  • An organic EL device was produced in the same manner as in Example 6.
  • the layer structure of the obtained organic EL device is as follows. ITO(130)/HI-1(5)/HT-1(10)/EBL-1(10)/BH-4:BD-4(25:2% by mass)/HBL-1(10)/ET- 1(15)/LiF(1)/Al(80)
  • the numbers in parentheses represent the film thickness (unit: nm).
  • the obtained organic EL device was evaluated by the same method as in Example 6. The results are shown in Table 5.
  • Comparative example 2 An organic EL device was prepared and evaluated in the same manner as in Example 16 except that the host materials shown in Table 5 were used. The results are shown in Table 5.
  • Example 17 and Comparative Example 3 An organic EL device was prepared and evaluated in the same manner as in Example 16 except that the dopant materials and host materials shown in Table 6 were used. The results are shown in Table 6.
  • Example 18 and Comparative Example 4 An organic EL device was prepared and evaluated in the same manner as in Example 16 except that the dopant materials and host materials shown in Table 7 were used. The results are shown in Table 7.
  • Example 19 (Production of tandem type organic EL device> Example 19 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 1 minute. The film thickness of ITO was 130 nm. -Formation of the first light-emitting unit The glass substrate with the transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and a compound is prepared by first covering the transparent electrode on the surface where the transparent electrode line is formed.
  • HT-3 and compound HI-2 were co-evaporated to form a hole injection layer having a film thickness of 10 nm.
  • the concentration of the compound HT-3 in the hole injection layer was 97% by mass, and the concentration of the compound HI-2 was 3% by mass.
  • the compound HT-3 was vapor-deposited on the hole injection layer to form a 70-nm-thick first hole transport layer.
  • the compound EBL-3 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.
  • compound BH-4 and compound BD-1 were co-evaporated to form a blue fluorescent light emitting layer as a first light emitting layer having a film thickness of 25 nm.
  • the concentration of the compound BH-4 and the concentration of the compound BD-1 in the blue fluorescent light emitting layer were 98% by mass and 2% by mass, respectively.
  • the compound HBL-1 was vapor-deposited on the blue fluorescent emitting layer to form an electron transporting layer having a film thickness of 10 nm.
  • the compound ET-2 and lithium (Li) were co-evaporated on the electron transport layer to form a first N layer having a thickness of 10 nm.
  • the concentration of the compound ET-2 in the first N layer was 96% by mass, and the concentration of Li was 4% by mass.
  • the compound HT-3 and the compound HI-2 were co-evaporated on the first N layer to form a first P layer having a film thickness of 10 nm.
  • the concentration of the compound HT-3 in the first P layer was 90% by mass, and the concentration of the compound HI-2 was 10% by mass.
  • a compound EBL-3 was vapor-deposited on the first P layer to form a first hole transport layer having a film thickness of 10 nm.
  • the compound PGH-1 and the compound PGD-1 were co-evaporated to form a yellow phosphorescent light emitting layer as a second light emitting layer having a film thickness of 48 nm.
  • the concentration of the compound PGH-1 in the yellow phosphorescent-emitting layer was 80% by mass, and the concentration of the compound PGD-1 was 20% by mass.
  • the compound ET-1 was vapor-deposited on the yellow phosphorescent-emitting layer to form an electron-transporting layer having a thickness of 10 nm.
  • Second Charge Generation Layer the compound ET-2 and lithium (Li) were co-evaporated on the electron transport layer to form a second N layer having a thickness of 35 nm.
  • the concentration of the compound ET-2 in the second N layer was 96% by mass, and the concentration of Li was 4% by mass.
  • compound HT-3 and compound HI-2 were co-evaporated to form a second P layer having a film thickness of 10 nm.
  • the concentration of the compound HT-3 in the second P layer was 90% by mass, and the concentration of the compound HI-2 was 10% by mass.
  • a compound HT-3 was vapor-deposited on the second P layer to form a first hole-transporting layer having a film thickness of 70 nm.
  • the compound EBL-3 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.
  • compound BH-4 and compound BD-1 were co-evaporated to form a blue fluorescent light emitting layer as a third light emitting layer having a film thickness of 25 nm.
  • the concentration of the compound BH-4 and the concentration of the compound BD-1 in the blue fluorescent light emitting layer were 98% by mass and 2% by mass, respectively.
  • the compound HBL-1 was vapor-deposited on the blue fluorescent emitting layer to form a first electron transporting layer having a film thickness of 10 nm.
  • the compound ET-1 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a film thickness of 10 nm.
  • lithium fluoride (LiF) was vapor-deposited on the second electron transport layer to form an electron injection layer having a film thickness of 1 nm.
  • metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode having a film thickness of 80 nm.
  • a bottom emission type organic EL element was produced.
  • the layer structure of the obtained organic EL device is as follows. ITO(130)/HT-3:HI-2(10,97%:3%)/HT-3(70)/EBL-3(10)/BH-4:BD-1(25,98%:2) %)/HBL-1(10)/ET-2:Li(10,96%:4%)/HT-3:HI-2(10,90%:10%)/EBL-3(10)/PGH -1: PGD-1 (48, 80%: 20%)/ET-1 (10)/ET-2: Li (35, 96%: 4%)/HT-3: HI-2 (10, 90%) : 10%)/HT-3(70)/EBL-3(10)/BH-4: BD-1(25,98%:2%)/HBL-1(10)/ET-1(10)/ LiF(1)/Al(80)
  • the numbers in parentheses represent the film thickness (unit: nm).
  • Example 20 and Comparative Example 5 An organic EL device was produced in the same manner as in Example 19 except that the host material and the dopant material shown in Table 8 below were used in the first light emitting layer and the third light emitting layer, and evaluated in the same manner as in Example 19. The results are shown in Table 8.
  • Synthesis Example 2 Synthesis of Compound BD-2 BD-2 was synthesized by the following synthetic route.
  • the obtained solid was purified by column chromatography to obtain a white solid (5.0 g, yield 77%).
  • the obtained solid was the target compound, Compound 1-3.
  • m/e was 790 with respect to a molecular weight of 790.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

This organic electroluminescence element has a negative electrode, a positive electrode, and an organic layer between the negative electrode and the positive electrode. The organic layer contains: a compound represented by formula (1); and a compound A which is a compound represented by formulas (11-1) and (11-3) or a compound represented by formulas (11-2) and (11-3).

Description

有機エレクトロルミネッセンス素子及び電子機器Organic electroluminescence device and electronic device
　本発明は、有機エレクトロルミネッセンス素子及び電子機器に関する。 The present invention relates to an organic electroluminescence element and electronic equipment.
　有機エレクトロルミネッセンス素子（以下、有機ＥＬ素子ということがある）に電圧を印加すると、陽極から正孔が、また陰極から電子が、それぞれ発光層に注入される。そして、発光層において、注入された正孔と電子とが再結合し、励起子が形成される。 When a voltage is applied to an organic electroluminescence element (hereinafter, sometimes 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.
　特許文献１には、有機ＥＬ素子の発光層の材料として、特定の縮環構造を有する化合物を用いることが開示されている。 Patent Document 1 discloses that a compound having a specific condensed ring structure is used as a material of a light emitting layer of an organic EL element.
国際公開第２０１８／１５１０６５号International Publication No. 2018/151065
　本発明の目的は、低電圧で駆動し、長寿命な有機ＥＬ素子、及び当該有機ＥＬ素子を用いた電子機器を提供することである。 An object of the present invention is to provide an organic EL element which is driven at a low voltage and has a long life, and an electronic device using the organic EL element.
　本発明によれば、以下の有機ＥＬ素子及び電子機器が提供される。
１．陰極と、陽極と、前記陰極と前記陽極との間に有機層を有する有機エレクトロルミネッセンス素子であって、
　前記有機層が、下記式（１）で表される化合物と、
　下記式（１１－１）及び（１１－３）で表される化合物、又は下記式（１１－２）及び（１１－３）で表される化合物である、化合物Ａと、を含む、有機エレクトロルミネッセンス素子。
Figure JPOXMLDOC01-appb-C000022
 ［式（１）中、
　Ｒ１～Ｒ８のうちの１個以上は、－Ｌ１３－Ａｒ１３である。
　Ｌ１１～Ｌ１３は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　Ｌ１３が２個以上存在する場合、２個以上のＬ１３は、互いに同一であってもよいし、異なっていてもよい。
　Ａｒ１１～Ａｒ１３は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ａｒ１３が２個以上存在する場合、２個以上のＡｒ１３は、互いに同一であってもよいし、異なっていてもよい。
　－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］
Figure JPOXMLDOC01-appb-C000023
 [（式（１１－１）、式（１１－２）及び式（１１－３）中、
　環Ａは、置換もしくは無置換の環形成炭素数１０～５０の縮合アリール環、置換もしくは無置換の環形成原子数８～５０の縮合複素環、又は下記式（Ｘ）で表されるベンゼン環である。）
Figure JPOXMLDOC01-appb-C000024
 （式（Ｘ）中、
　２つの＊で示す環形成炭素原子の一方で、前記式（１１－１）又は前記式（１１－２）のベンゼン環Ｂから延びる＊と結合し、他方で前記式（１１－３）のベンゼン環Ｃから延びる単結合と結合する。
　前記式（１１－１）の２つの＊は、それぞれ、前記環Ａの前記縮合アリール環の環形成炭素原子、前記縮合複素環の環形成原子、又は前記式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合する。
　前記式（１１－２）の３つの＊は、それぞれ、前記環Ａの前記縮合アリール環の環形成炭素原子、前記縮合複素環の環形成原子、又は前記式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合する。）
　Ｒ１０１～Ｒ１１６のうち隣接する２つ以上の１組以上は、置換もしくは無置換の飽和又は不飽和の環を形成するか、あるいは前記環を形成しない。
　前記環を形成しないＲ１０１～Ｒ１１６、及びＲ１１７は、それぞれ独立に、
水素原子、ハロゲン原子、シアノ基、ニトロ基、ハロアルキル基、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
－Ｃ（＝Ｏ）（Ｒ９０８）、
－ＣＯＯ（Ｒ９０９）、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０９は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０９が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０９のそれぞれは同一でもよく、異なっていてもよい。
　ｎは１又は２の整数である。ｎが２である場合、２つのＲ１１７は同じであってもよく、また、異なってもよい。]
２．上記１に記載の有機エレクトロルミネッセンス素子を備える電子機器。 According to the present invention, the following organic EL element and electronic device are provided.
1. A cathode, an anode, an organic electroluminescent element having an organic layer between the cathode and the anode,
The organic layer is a compound represented by the following formula (1),
An organic electroluminescent device containing a compound represented by the following formulas (11-1) and (11-3) or a compound A represented by the following formulas (11-2) and (11-3): Luminescence element.
Figure JPOXMLDOC01-appb-C000022
 [In Formula (1),
At least one of R 1 to R 8 is —L 13 —Ar 13 .
L 11 to L 13 are each independently
Single bond,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
When two or more L 13's are present, the two or more L 13 's may be the same as or different from each other.
Ar 11 to Ar 13 are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
When two or more Ar 13's are present, the two or more Ar 13 's may be the same or different from each other.
R 1 to R 8 which are not —L 13 —Ar 13 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
Figure JPOXMLDOC01-appb-C000023
 [(In Formula (11-1), Formula (11-2) and Formula (11-3),
Ring A is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms, or a benzene ring represented by the following formula (X). Is. )
Figure JPOXMLDOC01-appb-C000024
 (In formula (X),
One of the two ring-forming carbon atoms represented by * is bonded to * extending from the benzene ring B of the formula (11-1) or (11-2), and the other benzene of the formula (11-3). Bond with a single bond extending from ring C.
The two * in the formula (11-1) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
The three *'s in the formula (11-2) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of. )
One or more adjacent two or more sets of R 101 to R 116 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
R 101 to R 116 and R 117 that do not form a ring are each independently
Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
-C(=O)(R 908 ),
-COO (R 909 ),
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 909 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two or more R 901 to R 909 are present, each of the two or more R 901 to R 909 may be the same or different.
n is an integer of 1 or 2. When n is 2, the two R 117 may be the same or different. ]
2. An electronic device comprising the organic electroluminescence element according to 1 above.
　本発明によれば、低電圧で駆動し、長寿命である有機ＥＬ素子、及び当該有機ＥＬ素子を用いた電子機器が提供できる。 According to the present invention, it is possible to provide an organic EL element that is driven at a low voltage and has a long life, and an electronic device using the organic EL element.
本発明の第１の態様の有機ＥＬ素子の概略構成を示す図である。It is a figure which shows schematic structure of the organic EL element of the 1st aspect of this invention. 本発明の第２の態様の有機ＥＬ素子の概略構成を示す図である。It is a figure which shows schematic structure of the organic EL element of the 2nd aspect of this invention. 本発明の第３の態様の有機ＥＬ素子の概略構成を示す図である。It is a figure which shows schematic structure of the organic EL element of the 3rd aspect of this invention. 本発明の第４の態様の有機ＥＬ素子の概略構成を示す図である。It is a figure which shows schematic structure of the organic EL element of the 4th aspect of this invention. 本発明の第５の態様の有機ＥＬ素子の概略構成を示す図である。It is a figure which shows schematic structure of the organic EL element of the 5th aspect of this invention.
［定義］
　本明細書において、水素原子とは、中性子数が異なる同位体、即ち、軽水素（protium）、重水素（deuterium）、三重水素（tritium）を包含する。 [Definition]
In the present specification, the hydrogen atom includes isotopes having different neutron numbers, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
　本明細書において、化学構造式中、「Ｒ」等の記号や重水素原子を表す「Ｄ」が明示されていない結合可能位置には、水素原子、即ち、軽水素原子、重水素原子、又は三重水素原子が結合しているものとする。 In the present specification, in the chemical structural formulas, a hydrogen atom, that is, a deuterium atom, a deuterium atom, or a hydrogen atom is present at a bondable position where a symbol such as “R” or “D” that represents a deuterium atom is not specified. It is assumed that tritium atoms are bonded.
　本明細書において、環形成炭素数とは、原子が環状に結合した構造の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、複素環化合物）の当該環自体を構成する原子のうちの炭素原子の数を表す。当該環が置換基によって置換される場合、置換基に含まれる炭素は環形成炭素数には含まない。以下で記される「環形成炭素数」については、特筆しない限り同様とする。例えば、ベンゼン環は環形成炭素数が６であり、ナフタレン環は環形成炭素数が１０であり、ピリジン環は環形成炭素数５であり、フラン環は環形成炭素数４である。また例えば、９，９－ジフェニルフルオレニル基の環形成炭素数は１３であり、９，９’－スピロビフルオレニル基の環形成炭素数は２５である。
　また、ベンゼン環やナフタレン環に置換基として例えばアルキル基が置換している場合、当該アルキル基の炭素数は、環形成炭素数の数に含めない。 In the present specification, the ring-forming carbon number constitutes the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridge compound, a carbocyclic compound, a heterocyclic compound). Represents the number of carbon atoms in an atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number. The same applies to the “ring carbon number” described below unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for example, the ring-forming carbon number of the 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of the 9,9′-spirobifluorenyl group is 25.
When the benzene ring or naphthalene ring is substituted with, for example, an alkyl group, the carbon number of the alkyl group is not included in the number of ring-forming carbon atoms.
　本明細書において、環形成原子数とは、原子が環状に結合した構造（例えば単環、縮合環、環集合）の化合物（例えば単環化合物、縮合環化合物、架橋化合物、炭素環化合物、複素環化合物）の当該環自体を構成する原子の数を表す。環を構成しない原子（例えば環を構成する原子の結合を終端する水素原子）や、当該環が置換基によって置換される場合の置換基に含まれる原子は環形成原子数には含まない。以下で記される「環形成原子数」については、特筆しない限り同様とする。例えば、ピリジン環の環形成原子数は６であり、キナゾリン環の環形成原子数は１０であり、フラン環の環形成原子数は５である。ピリジン環やキナゾリン環の炭素原子にそれぞれ結合している水素原子や置換基を構成する原子については、環形成原子数の数に含めない。 In the present specification, the number of ring-forming atoms means a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic ring, a condensed ring, a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle Represents the number of atoms constituting the ring itself of the ring compound). An atom that does not form a ring (for example, a hydrogen atom that terminates the bond of atoms that form a ring) or an atom included in a substituent when the ring is substituted with a substituent is not included in the number of ring-forming atoms. The same applies to the “number of ring-forming atoms” described below unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. Hydrogen atoms bonded to carbon atoms of the pyridine ring or quinazoline ring or atoms constituting a substituent are not included in the number of ring-forming atoms.
　本明細書において、「置換もしくは無置換の炭素数ＸＸ～ＹＹのＺＺ基」という表現における「炭素数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の炭素数を表すものであり、置換されている場合の置換基の炭素数は含めない。ここで、「ＹＹ」は「ＸＸ」よりも大きく、「ＸＸ」と「ＹＹ」はそれぞれ１以上の整数を意味する。 In the present specification, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” means the number of carbon atoms when the ZZ group is unsubstituted. If present, the carbon number of the substituent is not included. Here, "YY" is larger than "XX", and "XX" and "YY" each mean an integer of 1 or more.
　本明細書において、「置換もしくは無置換の原子数ＸＸ～ＹＹのＺＺ基」という表現における「原子数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の原子数を表すものであり、置換されている場合の置換基の原子数は含めない。ここで、「ＹＹ」は「ＸＸ」よりも大きく、「ＸＸ」と「ＹＹ」はそれぞれ１以上の整数を意味する。 In the present specification, “atom number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms when the ZZ group is unsubstituted. The number of atoms of the substituent when it is included is not included. Here, "YY" is larger than "XX", and "XX" and "YY" each mean an integer of 1 or more.
　「置換もしくは無置換のＺＺ基」という場合における「無置換」とはＺＺ基が置換基で置換されておらず、水素原子が結合していることを意味する。あるいは、「置換もしくは無置換のＺＺ基」という場合における「置換」とはＺＺ基における１つ以上の水素原子が、置換基と置き換わっていることを意味する。「ＡＡ基で置換されたＢＢ基」という場合における「置換」も同様に、ＢＢ基における１つ以上の水素原子が、ＡＡ基と置き換わっていることを意味する。 “In the case of “substituted or unsubstituted ZZ group”, “unsubstituted” means that the ZZ group is not substituted with a substituent and a hydrogen atom is bonded. Alternatively, “substituted” in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with substituents. Similarly, "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 groups.
　以下、本明細書に記載の置換基について説明する。
　本明細書に記載の「無置換のアリール基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「無置換の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
　本明細書に記載の「無置換のアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。
　本明細書に記載の「無置換のアルケニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
　本明細書に記載の「無置換のアルキニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
　本明細書に記載の「無置換のシクロアルキル基」の環形成炭素数は、本明細書に別途記載のない限り、３～５０であり、好ましくは３～２０、より好ましくは３～６である。
　本明細書に記載の「無置換のアリーレン基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「無置換の２価の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
　本明細書に記載の「無置換のアルキレン基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。 The substituents described in the present specification will be described below.
The number of ring-forming carbon atoms of the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. ..
The number of ring-forming atoms of the “unsubstituted heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification. is there.
The "unsubstituted alkyl group" described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20, and more preferably 1 to 6 unless otherwise specified in the present specification.
The carbon number of the “unsubstituted alkenyl group” described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
The "unsubstituted alkynyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in the present specification.
The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in the present specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in the present specification. is there.
The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. ..
The number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 unless otherwise specified in the present specification. ~18.
The “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in the present specification.
　本明細書に記載の「置換もしくは無置換のアリール基」の具体例（具体例群Ｇ１）としては、以下の無置換のアリール基及び置換のアリール基等が挙げられる。（ここで、無置換のアリール基とは「置換もしくは無置換のアリール基」が「無置換のアリール基」である場合を指し、置換のアリール基とは「置換もしくは無置換のアリール基」が「置換のアリール基」である場合を指す。）以下、単に「アリール基」という場合は、「無置換のアリール基」と「置換のアリール基」の両方を含む。
　「置換のアリール基」は「無置換のアリール基」が置換基を有する場合であり、下記の「無置換のアリール基」が置換基を有する基や、置換のアリール基の例等が挙げられる。尚、ここに列挙した「無置換のアリール基」の例や「置換のアリール基」の例は一例に過ぎず、本明細書に記載の「置換のアリール基」には、「無置換のアリール基」が置換基を有する基がさらに置換基を有する基や、「置換のアリール基」がさらに置換基を有する基等も含まれる。 Specific examples of the “substituted or unsubstituted aryl group” (specific example group G1) described in the present specification include the following unsubstituted aryl groups and substituted aryl groups. (Here, the unsubstituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group”, and the substituted aryl group is the “substituted or unsubstituted aryl group”. The term "substituted aryl group" is used below.) Hereinafter, the term "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".
The “substituted aryl group” is a case where the “unsubstituted aryl group” has a substituent, and examples thereof include a group in which the “unsubstituted aryl group” has a substituent and a substituted aryl group. .. The examples of the “unsubstituted aryl group” and the “substituted aryl group” listed here are merely examples, and the “substituted aryl group” described in the present specification includes “unsubstituted aryl group”. A group in which the "group" has a substituent further has a substituent, a group in which the "substituted aryl group" further has a substituent, and the like are also included.
　無置換のアリール基：
フェニル基、
ｐ－ビフェニル基、
ｍ－ビフェニル基、
ｏ－ビフェニル基、
ｐ－ターフェニル－４－イル基、
ｐ－ターフェニル－３－イル基、
ｐ－ターフェニル－２－イル基、
ｍ－ターフェニル－４－イル基、
ｍ－ターフェニル－３－イル基、
ｍ－ターフェニル－２－イル基、
ｏ－ターフェニル－４－イル基、
ｏ－ターフェニル－３－イル基、
ｏ－ターフェニル－２－イル基、
１－ナフチル基、
２－ナフチル基、
アントリル基、
ベンゾアントリル基、
フェナントリル基、
ベンゾフェナントリル基、
フェナレニル基、
ピレニル基、
クリセニル基、
ベンゾクリセニル基、
トリフェニレニル基、
ベンゾトリフェニレニル基、
テトラセニル基、
ペンタセニル基、
フルオレニル基、
９，９’－スピロビフルオレニル基、
ベンゾフルオレニル基、
ジベンゾフルオレニル基、
フルオランテニル基、
ベンゾフルオランテニル基、
ペリレニル基 Unsubstituted aryl group:
Phenyl group,
p-biphenyl group,
m-biphenyl group,
an 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,
an o-terphenyl-4-yl group,
an o-terphenyl-3-yl group,
an o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
Anthryl group,
A benzoanthryl group,
Phenanthryl group,
A benzophenanthryl group,
Phenalenyl group,
A pyrenyl group,
A chrysenyl group,
A benzochrysenyl group,
A triphenylenyl group,
A benzotriphenylenyl group,
A tetracenyl group,
Pentacenyl group,
Fluorenyl group,
9,9'-spirobifluorenyl group,
A benzofluorenyl group,
A dibenzofluorenyl group,
A fluoranthenyl group,
A benzofluoranthenyl group,
Perenyl group
　置換のアリール基：
ｏ－トリル基、
ｍ－トリル基、
ｐ－トリル基、
パラ－キシリル基、
メタ－キシリル基、
オルト－キシリル基、
パラ－イソプロピルフェニル基、
メタ－イソプロピルフェニル基、
オルト－イソプロピルフェニル基、
パラ－ｔ－ブチルフェニル基、
メタ－ｔ－ブチルフェニル基、
オルト－ｔ－ブチルフェニル基、
３，４，５－トリメチルフェニル基、
９，９－ジメチルフルオレニル基、
９，９－ジフェニルフルオレニル基、
９，９－ジ（４－メチルフェニル）フルオレニル基、
９，９－ジ（４－イソプロピルフェニル）フルオレニル基、
９，９－ジ（４－ｔブチルフェニル）フルオレニル基、
シアノフェニル基、
トリフェニルシリルフェニル基、
トリメチルシリルフェニル基、
フェニルナフチル基、
ナフチルフェニル基 Substituted aryl group:
o-tolyl group,
m-tolyl group,
p-tolyl group,
Para-xylyl group,
Meta-xylyl group,
Ortho-xylyl 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-di(4-methylphenyl)fluorenyl group,
9,9-di(4-isopropylphenyl)fluorenyl group,
9,9-di(4-tbutylphenyl)fluorenyl group,
Cyanophenyl group,
Triphenylsilylphenyl group,
Trimethylsilylphenyl group,
Phenylnaphthyl group,
Naphthylphenyl group
　本明細書に記載の「複素環基」は、環形成原子にヘテロ原子を少なくとも１つ含む環状の基である。ヘテロ原子の具体例としては、窒素原子、酸素原子、硫黄原子、ケイ素原子、リン原子、及びホウ素原子が挙げられる。
　本明細書に記載の「複素環基」は、単環の基であっても縮合環の基であってもよい。
　本明細書に記載の「複素環基」は、芳香族複素環基であっても脂肪族複素環基であってもよい。
　本明細書に記載の「置換もしくは無置換の複素環基」の具体例（具体例群Ｇ２）としては、以下の無置換の複素環基及び置換の複素環基等が挙げられる。（ここで、無置換の複素環基とは「置換もしくは無置換の複素環基」が「無置換の複素環基」である場合を指し、置換の複素環基とは「置換もしくは無置換の複素環基」が「置換の複素環基」である場合を指す。）以下、単に「複素環基」という場合は、「無置換の複素環基」と「置換の複素環基」の両方を含む。
　「置換の複素環基」は「無置換の複素環基」が置換基を有する場合であり、下記の「無置換の複素環基」が置換基を有する基や、置換の複素環基の例等が挙げられる。尚、ここに列挙した「無置換の複素環基」の例や「置換の複素環基」の例は一例に過ぎず、本明細書に記載の「置換の複素環基」には、「無置換の複素環基」が置換基を有する基がさらに置換基を有する基や、「置換の複素環基」がさらに置換基を有する基等も含まれる。 The "heterocyclic group" described in the present specification is a cyclic group containing at least one hetero atom as a ring forming atom. Specific examples of 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 in the present specification may be a monocyclic group or a condensed ring group.
The "heterocyclic group" described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.
Specific examples of the “substituted or unsubstituted heterocyclic group” (specific group G2) described in the present specification include the following unsubstituted heterocyclic groups and substituted heterocyclic groups. (Here, the term “unsubstituted heterocyclic group” refers to the case where the “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”, and the term “substituted heterocyclic group” refers to a “substituted or unsubstituted heterocyclic group”. The term "heterocyclic group" means a "substituted heterocyclic group".) In the following, when simply referred to as "heterocyclic group", it means both "unsubstituted heterocyclic group" and "substituted heterocyclic group". Including.
The “substituted heterocyclic group” is a case where the “unsubstituted heterocyclic group” has a substituent, and the following “unsubstituted heterocyclic group” is a group having a substituent or an example of a substituted heterocyclic group. Etc. The examples of the “unsubstituted heterocyclic group” and the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in the present specification includes “none A group in which the "substituted heterocyclic group" has a substituent further has a substituent, a group in which the "substituted heterocyclic group" further has a substituent, and the like are also included.
　窒素原子を含む無置換の複素環基：
ピロリル基、
イミダゾリル基、
ピラゾリル基、
トリアゾリル基、
テトラゾリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ピリジル基、
ピリダジニル基、
ピリミジニル基、
ピラジニル基、
トリアジニル基、
インドリル基、
イソインドリル基、
インドリジニル基、
キノリジニル基、
キノリル基、
イソキノリル基、
シンノリル基、
フタラジニル基、
キナゾリニル基、
キノキサリニル基、
ベンゾイミダゾリル基、
インダゾリル基、
フェナントロリニル基、
フェナントリジニル基、
アクリジニル基、
フェナジニル基、
カルバゾリル基、
ベンゾカルバゾリル基、
モルホリノ基、
フェノキサジニル基、
フェノチアジニル基、
アザカルバゾリル基、
ジアザカルバゾリル基 An unsubstituted heterocyclic group containing a nitrogen atom:
A pyrrolyl group,
An imidazolyl group,
A pyrazolyl group,
Triazolyl group,
A tetrazolyl group,
An oxazolyl group,
An isoxazolyl group,
Oxadiazolyl group,
Thiazolyl group,
An isothiazolyl group,
Thiadiazolyl group,
A pyridyl group,
A pyridazinyl group,
A pyrimidinyl group,
A pyrazinyl group,
Triazinyl group,
Indolyl group,
Isoindolyl group,
An indolizinyl group,
A quinolidinyl group,
Quinolyl group,
An isoquinolyl group,
Cinnolyl group,
Phthalazinyl group,
A quinazolinyl group,
A quinoxalinyl group,
Benzimidazolyl group,
Indazolyl group,
Phenanthrolinyl group,
A phenanthridinyl group,
An acridinyl group,
Phenazinyl group,
Carbazolyl group,
A benzocarbazolyl group,
Morpholino group,
A phenoxazinyl group,
Phenothiazinyl group,
An azacarbazolyl group,
Diazacarbazolyl group
　酸素原子を含む無置換の複素環基：
フリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
キサンテニル基、
ベンゾフラニル基、
イソベンゾフラニル基、
ジベンゾフラニル基、
ナフトベンゾフラニル基、
ベンゾオキサゾリル基、
ベンゾイソキサゾリル基、
フェノキサジニル基、
モルホリノ基、
ジナフトフラニル基、
アザジベンゾフラニル基、
ジアザジベンゾフラニル基、
アザナフトベンゾフラニル基、
ジアザナフトベンゾフラニル基 An unsubstituted heterocyclic group containing an oxygen atom:
Frill group,
An oxazolyl group,
An isoxazolyl group,
Oxadiazolyl group,
A xanthenyl group,
A benzofuranyl group,
An isobenzofuranyl group,
A dibenzofuranyl group,
Naphthobenzofuranyl group,
A benzoxazolyl group,
A benzisoxazolyl group,
A phenoxazinyl group,
Morpholino group,
Dinaphthofuranyl group,
An azadibenzofuranyl group,
A diazadibenzofuranyl group,
An azanaphthobenzofuranyl group,
Diazanaphthobenzofuranyl group
　硫黄原子を含む無置換の複素環基：
チエニル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ベンゾチオフェニル基、
イソベンゾチオフェニル基、
ジベンゾチオフェニル基、
ナフトベンゾチオフェニル基、
ベンゾチアゾリル基、
ベンゾイソチアゾリル基、
フェノチアジニル基、
ジナフトチオフェニル基、
アザジベンゾチオフェニル基、
ジアザジベンゾチオフェニル基、
アザナフトベンゾチオフェニル基、
ジアザナフトベンゾチオフェニル基 Unsubstituted heterocyclic group containing a sulfur atom:
A thienyl group,
Thiazolyl group,
An isothiazolyl group,
Thiadiazolyl group,
A benzothiophenyl group,
An isobenzothiophenyl group,
A dibenzothiophenyl group,
Naphthobenzothiophenyl group,
A benzothiazolyl group,
Benzoisothiazolyl group,
Phenothiazinyl group,
Dinaphthothiophenyl group,
An azadibenzothiophenyl group,
Diazadibenzothiophenyl group,
Azanaphthobenzothiophenyl group,
Diazanaphthobenzothiophenyl group
　窒素原子を含む置換の複素環基：
（９－フェニル）カルバゾリル基、
（９－ビフェニリル）カルバゾリル基、
（９－フェニル）フェニルカルバゾリル基、
（９－ナフチル）カルバゾリル基、
ジフェニルカルバゾール－９－イル基、
フェニルカルバゾール－９－イル基、
メチルベンゾイミダゾリル基、
エチルベンゾイミダゾリル基、
フェニルトリアジニル基、
ビフェニリルトリアジニル基、
ジフェニルトリアジニル基、
フェニルキナゾリニル基、
ビフェニリルキナゾリニル基 Substituted heterocyclic group containing a nitrogen atom:
(9-phenyl)carbazolyl group,
(9-biphenylyl)carbazolyl group,
(9-phenyl)phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
A diphenylcarbazol-9-yl group,
Phenylcarbazol-9-yl group,
A methylbenzimidazolyl group,
An ethylbenzimidazolyl group,
Phenyltriazinyl group,
Biphenylyltriazinyl group,
A diphenyltriazinyl group,
Phenylquinazolinyl group,
Biphenylylquinazolinyl group
　酸素原子を含む置換の複素環基：
フェニルジベンゾフラニル基、
メチルジベンゾフラニル基、
ｔ－ブチルジベンゾフラニル基、
スピロ［９Ｈ－キサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基 Substituted heterocyclic group containing an oxygen atom:
Phenyldibenzofuranyl group,
A methyldibenzofuranyl group,
t-butyldibenzofuranyl group,
Monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene]
　硫黄原子を含む置換の複素環基：
フェニルジベンゾチオフェニル基、
メチルジベンゾチオフェニル基、
ｔ－ブチルジベンゾチオフェニル基、
スピロ［９Ｈ－チオキサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基 Substituted heterocyclic group containing a sulfur atom:
Phenyldibenzothiophenyl group,
Methyldibenzothiophenyl group,
t-butyldibenzothiophenyl group,
Monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene]
　窒素原子、酸素原子、及び硫黄原子のうち少なくとも１つを含む下記無置換の複素環の環形成原子に結合した１つの水素原子を除くことにより誘導される１価の基、及び下記無置換の複素環の環形成原子に結合した１つの水素原子を除くことにより誘導される１価の基が置換基を有する基：  A monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocycle containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and the following unsubstituted A group in which a monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of a heterocycle has a substituent:
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
　式（ＸＹ－１）～（ＸＹ－１８）において、ＸＡ及びＹＡは、それぞれ独立に、酸素原子、硫黄原子、ＮＨ、ＣＨ２である。ただし、ＸＡ及びＹＡのうち少なくとも１つは酸素原子、硫黄原子、又はＮＨである。
　上記式（ＸＹ－１）～（ＸＹ－１８）で表される複素環は、任意の位置で結合を有して１価の複素環基となる。
　上記式（ＸＹ－１）～（ＸＹ－１８）で表される無置換の複素環から誘導される１価の基が置換基を有するとは、これらの式中の骨格を構成する炭素原子に結合した水素原子が置換基に置き換わっている場合、あるいは、ＸＡやＹＡがＮＨもしくはＣＨ２であり、これらＮＨもしくはＣＨ２における水素原子が、置換基と置き換わっている状態を指す。 In formulas (XY-1) to (XY-18), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
The heterocycles represented by the above formulas (XY-1) to (XY-18) have a bond at any position to become a monovalent heterocyclic group.
A monovalent group derived from an unsubstituted heterocycle represented by any of the above formulas (XY-1) to (XY-18) has a substituent means that the carbon atoms constituting the skeleton in these formulas have when bonded hydrogen atoms is replaced by a substituent, or, X a and Y a is NH or CH 2, hydrogen atoms in these NH or CH 2 may refer to a state in which is replaced by a substituent.
　本明細書に記載の「置換もしくは無置換のアルキル基」の具体例（具体例群Ｇ３）としては、以下の無置換のアルキル基及び置換のアルキル基が挙げられる。（ここで、無置換のアルキル基とは「置換もしくは無置換のアルキル基」が「無置換のアルキル基」である場合を指し、置換のアルキル基とは「置換もしくは無置換のアルキル基」が「置換のアルキル基」である場合を指す。）以下、単に「アルキル基」という場合は、「無置換のアルキル基」と「置換のアルキル基」の両方を含む。
　「置換のアルキル基」は「無置換のアルキル基」が置換基を有する場合であり、下記の「無置換のアルキル基」が置換基を有する基や、置換のアルキル基の例等が挙げられる。尚、ここに列挙した「無置換のアルキル基」の例や「置換のアルキル基」の例は一例に過ぎず、本明細書に記載の「置換のアルキル基」には、「無置換のアルキル基」が置換基を有する基がさらに置換基を有する基や、「置換のアルキル基」がさらに置換基を有する基等も含まれる。 Specific examples of the “substituted or unsubstituted alkyl group” (specific group G3) described in the present specification include the following unsubstituted alkyl groups and substituted alkyl groups. (Here, the unsubstituted alkyl group refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”, and the substituted alkyl group is the “substituted or unsubstituted alkyl group”. The term "substituted alkyl group" is used below.) Hereinafter, the term "alkyl group" includes both "unsubstituted alkyl group" and "substituted alkyl group".
The “substituted alkyl group” is a case where the “unsubstituted alkyl group” has a substituent, and examples thereof include a group in which the “unsubstituted alkyl group” has a substituent and a substituted alkyl group. .. The examples of the “unsubstituted alkyl group” and the “substituted alkyl group” listed here are merely examples, and the “substituted alkyl group” described in the present specification includes “unsubstituted alkyl group”. The group in which the "group" has a substituent further has a substituent, the group in which the "substituted alkyl group" further has a substituent, and the like are also included.
　無置換のアルキル基：
メチル基、
エチル基、
ｎ－プロピル基、
イソプロピル基、
ｎ－ブチル基、
イソブチル基、
ｓ－ブチル基、
ｔ－ブチル基 Unsubstituted alkyl group:
Methyl group,
Ethyl group,
n-propyl group,
Isopropyl group,
n-butyl group,
Isobutyl group,
s-butyl group,
t-butyl group
　置換のアルキル基：
ヘプタフルオロプロピル基（異性体を含む）、
ペンタフルオロエチル基、
２,２,２－トリフルオロエチル基、
トリフルオロメチル基 Substituted alkyl group:
Heptafluoropropyl group (including isomers),
Pentafluoroethyl group,
2,2,2-trifluoroethyl group,
Trifluoromethyl group
　本明細書に記載の「置換もしくは無置換のアルケニル基」の具体例（具体例群Ｇ４）としては、以下の無置換のアルケニル基及び置換のアルケニル基等が挙げられる。（ここで、無置換のアルケニル基とは「置換もしくは無置換のアルケニル基」が「無置換のアルケニル基」である場合を指し、「置換のアルケニル基」とは「置換もしくは無置換のアルケニル基」が「置換のアルケニル基」である場合を指す。）以下、単に「アルケニル基」という場合は、「無置換のアルケニル基」と「置換のアルケニル基」の両方を含む。
　「置換のアルケニル基」は「無置換のアルケニル基」が置換基を有する場合であり、下記の「無置換のアルケニル基」が置換基を有する基や、置換のアルケニル基の例等が挙げられる。尚、ここに列挙した「無置換のアルケニル基」の例や「置換のアルケニル基」の例は一例に過ぎず、本明細書に記載の「置換のアルケニル基」には、「無置換のアルケニル基」が置換基を有する基がさらに置換基を有する基や、「置換のアルケニル基」がさらに置換基を有する基等も含まれる。 Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in the present specification include the following unsubstituted alkenyl groups and substituted alkenyl groups. (Here, 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 the “substituted or unsubstituted alkenyl group”. Is a "substituted alkenyl group".) Hereinafter, when simply referred to as "alkenyl group", it includes both "unsubstituted alkenyl group" and "substituted alkenyl group".
The “substituted alkenyl group” is a case where the “unsubstituted alkenyl group” has a substituent, and examples thereof include a group in which the “unsubstituted alkenyl group” has a substituent and a substituted alkenyl group. .. The examples of the “unsubstituted alkenyl group” and the “substituted alkenyl group” listed here are merely examples, and the “substituted alkenyl group” described in the present specification means “unsubstituted alkenyl group”. A group in which the "group" has a substituent further has a substituent, a group in which the "substituted alkenyl group" further has a substituent, and the like are also included.
　無置換のアルケニル基及び置換のアルケニル基：
ビニル基、
アリル基、
１－ブテニル基、
２－ブテニル基、
３－ブテニル基、
１，３－ブタンジエニル基、
１－メチルビニル基、
１－メチルアリル基、
１，１－ジメチルアリル基、
２－メチルアリル基、
１，２－ジメチルアリル基 Unsubstituted alkenyl group and substituted alkenyl group:
Vinyl group,
Allyl group,
1-butenyl group,
2-butenyl group,
3-butenyl group,
1,3-butanedienyl group,
1-methyl vinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group,
1,2-dimethylallyl group
　本明細書に記載の「置換もしくは無置換のアルキニル基」の具体例（具体例群Ｇ５）としては、以下の無置換のアルキニル基等が挙げられる。（ここで、無置換のアルキニル基とは、「置換もしくは無置換のアルキニル基」が「無置換のアルキニル基」である場合を指す。）以下、単に「アルキニル基」という場合は、「無置換のアルキニル基」と「置換のアルキニル基」の両方を含む。
　「置換のアルキニル基」は「無置換のアルキニル基」が置換基を有する場合であり、下記の「無置換のアルキニル基」が置換基を有する基等が挙げられる。 Specific examples of the “substituted or unsubstituted alkynyl group” (specific example group G5) described in the present specification include the following unsubstituted alkynyl groups. (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group." Hereinafter, when simply referred to as "alkynyl group", "unsubstituted" And “substituted alkynyl group”.
The “substituted alkynyl group” is a case where the “unsubstituted alkynyl group” has a substituent, and examples thereof include a group in which the “unsubstituted alkynyl group” has a substituent.
　無置換のアルキニル基：
エチニル基 Unsubstituted alkynyl group:
Ethynyl group
　本明細書に記載の「置換もしくは無置換のシクロアルキル基」の具体例（具体例群Ｇ６）としては、以下の無置換のシクロアルキル基及び置換のシクロアルキル基等が挙げられる。（ここで、無置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「無置換のシクロアルキル基」である場合を指し、置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「置換のシクロアルキル基」である場合を指す。）以下、単に「シクロアルキル基」という場合は、「無置換のシクロアルキル基」と「置換のシクロアルキル基」の両方を含む。
　「置換のシクロアルキル基」は「無置換のシクロアルキル基」が置換基を有する場合であり、下記の「無置換のシクロアルキル基」が置換基を有する基や、置換のシクロアルキル基の例等が挙げられる。尚、ここに列挙した「無置換のシクロアルキル基」の例や「置換のシクロアルキル基」の例は一例に過ぎず、本明細書に記載の「置換のシクロアルキル基」には、「無置換のシクロアルキル基」が置換基を有する基がさらに置換基を有する基や、「置換のシクロアルキル基」がさらに置換基を有する基等も含まれる。 Specific examples of the “substituted or unsubstituted cycloalkyl group” (specific group G6) described in the present specification include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups. (Here, the unsubstituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group is the “substituted or unsubstituted cycloalkyl group”. The term "cycloalkyl group" means a "substituted cycloalkyl group".) Hereinafter, when simply referred to as "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are referred to. Including.
The “substituted cycloalkyl group” is a case where the “unsubstituted cycloalkyl group” has a substituent, and the following “unsubstituted cycloalkyl group” is a group having a substituent or an example of a substituted cycloalkyl group Etc. The examples of the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group” listed here are merely examples, and the “substituted cycloalkyl group” described in the present specification includes A group in which the "substituted cycloalkyl group" has a substituent further includes a group, a group in which the "substituted cycloalkyl group" further has a substituent, and the like are also included.
　無置換の脂肪族環基：
シクロプロピル基、
シクロブチル基、
シクロペンチル基、
シクロヘキシル基、
１－アダマンチル基、
２－アダマンチル基、
１－ノルボルニル基、
２－ノルボルニル基 Unsubstituted aliphatic ring group:
Cyclopropyl group,
Cyclobutyl group,
Cyclopentyl group,
Cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group,
2-norbornyl group
　置換のシクロアルキル基：
４－メチルシクロヘキシル基 Substituted cycloalkyl group:
4-methylcyclohexyl group
　本明細書に記載の－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基の具体例（具体例群Ｇ７）としては、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）、
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）、
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）、
－Ｓｉ（Ｇ５）（Ｇ５）（Ｇ５）、
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は具体例群Ｇ１に記載の「アリール基」である。
　Ｇ２は具体例群Ｇ２に記載の「複素環基」である。
　Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。
　Ｇ５は具体例群Ｇ５に記載の「アルキニル基」である。
　Ｇ６は具体例群Ｇ６に記載の「シクロアルキル基」である。 Specific examples (specific example group G7) of the group 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)(G3),
-Si(G5)(G5)(G5),
-Si(G6)(G6)(G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is a "heterocyclic group" described in Specific Example Group G2.
G3 is an "alkyl group" described in Specific Example Group G3.
G5 is an "alkynyl group" described in Specific Example Group G5.
G6 is a "cycloalkyl group" described in Specific Example Group G6.
　本明細書に記載の－Ｏ－（Ｒ９０４）で表される基の具体例（具体例群Ｇ８）としては、
－Ｏ（Ｇ１）、
－Ｏ（Ｇ２）、
－Ｏ（Ｇ３）、
－Ｏ（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は具体例群Ｇ１に記載の「アリール基」である。
　Ｇ２は具体例群Ｇ２に記載の「複素環基」である。
　Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。
　Ｇ６は具体例群Ｇ６に記載の「シクロアルキル基」である。 Specific examples of the group represented by —O—(R 904 ) described in the present specification (specific example group G8) include:
-O (G1),
-O (G2),
-O (G3),
-O (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is a "heterocyclic group" described in Specific Example Group G2.
G3 is an "alkyl group" described in Specific Example Group G3.
G6 is a "cycloalkyl group" described in Specific Example Group G6.
　本明細書に記載の－Ｓ－（Ｒ９０５）で表される基の具体例（具体例群Ｇ９）としては、
－Ｓ（Ｇ１）、
－Ｓ（Ｇ２）、
－Ｓ（Ｇ３）、
－Ｓ（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は具体例群Ｇ１に記載の「アリール基」である。
　Ｇ２は具体例群Ｇ２に記載の「複素環基」である。
　Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。
　Ｇ６は具体例群Ｇ６に記載の「シクロアルキル基」である。 Specific examples of the group represented by -S-(R 905 ) described in the present specification (specific example group G9) include:
-S (G1),
-S (G2),
-S (G3),
-S (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is a "heterocyclic group" described in Specific Example Group G2.
G3 is an "alkyl group" described in Specific Example Group G3.
G6 is a "cycloalkyl group" described in Specific Example Group G6.
　本明細書に記載の－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基の具体例（具体例群Ｇ１０）としては、
－Ｎ（Ｇ１）（Ｇ１）、
－Ｎ（Ｇ２）（Ｇ２）、
－Ｎ（Ｇ１）（Ｇ２）、
－Ｎ（Ｇ３）（Ｇ３）、
－Ｎ（Ｇ６）（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は具体例群Ｇ１に記載の「アリール基」である。
　Ｇ２は具体例群Ｇ２に記載の「複素環基」である。
　Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。
　Ｇ６は具体例群Ｇ６に記載の「シクロアルキル基」である。 Specific examples of the group represented by —N(R 906 )(R 907 ) described in the present specification (specific example group G10) include:
-N(G1)(G1),
-N(G2)(G2),
-N(G1)(G2),
-N(G3)(G3),
-N (G6) (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is a "heterocyclic group" described in Specific Example Group G2.
G3 is an "alkyl group" described in Specific Example Group G3.
G6 is a "cycloalkyl group" described in Specific Example Group G6.
　本明細書に記載の「ハロゲン原子」の具体例（具体例群Ｇ１１）としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられる。 Specific examples of the “halogen atom” (specific example group G11) described in the present specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
　本明細書に記載の「アルコキシ基」の具体例としては、－Ｏ（Ｇ３）で表される基であり、ここで、Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。「無置換のアルコキシ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０、より好ましくは１～１８である。
　本明細書に記載の「アルキルチオ基」の具体例としては、－Ｓ（Ｇ３）で表される基であり、ここで、Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。「無置換のアルキルチオ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０、より好ましくは１～１８である。
　本明細書に記載の「アリールオキシ基」の具体例としては、－Ｏ（Ｇ１）で表される基であり、ここで、Ｇ１は具体例群Ｇ１に記載の「アリール基」である。「無置換のアリールオキシ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「アリールチオ基」の具体例としては、－Ｓ（Ｇ１）で表される基であり、ここで、Ｇ１は具体例群Ｇ１に記載の「アリール基」である。「無置換のアリールチオ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「アラルキル基」の具体例としては、－（Ｇ３）－（Ｇ１）で表される基であり、ここで、Ｇ３は具体例群Ｇ３に記載の「アルキル基」であり、Ｇ１は具体例群Ｇ１に記載の「アリール基」である。従って、「アラルキル基」は、「アリール基」が置換した、「置換のアルキル基」の一実施形態である。「無置換のアリール基」が置換した「無置換のアルキル基」である「無置換のアラルキル基」の炭素数は、本明細書に別途記載のない限り、７～５０であり、好ましくは７～３０、より好ましくは７～１８である。
　「アラルキル基」の具体例としては、例えば、ベンジル基、１－フェニルエチル基、２－フェニルエチル基、１－フェニルイソプロピル基、２－フェニルイソプロピル基、フェニル－ｔ－ブチル基、α－ナフチルメチル基、１－α－ナフチルエチル基、２－α－ナフチルエチル基、１－α－ナフチルイソプロピル基、２－α－ナフチルイソプロピル基、β－ナフチルメチル基、１－β－ナフチルエチル基、２－β－ナフチルエチル基、１－β－ナフチルイソプロピル基、２－β－ナフチルイソプロピル基等が挙げられる。 A specific example of the "alkoxy group" described in the present specification is a group represented by -O(G3), wherein G3 is an "alkyl group" described in the specific example group G3. The carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18 unless otherwise specified in the present specification.
A specific example of the “alkylthio group” described in the present specification is a group represented by —S(G3), wherein G3 is the “alkyl group” described in the specific example group G3. The carbon number of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18 unless otherwise specified in the present specification.
A specific example of the "aryloxy group" described in the present specification is a group represented by -O(G1), wherein G1 is the "aryl group" described in the specific example group G1. The number of ring-forming carbon atoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.
A specific example of the “arylthio group” described in the present specification is a group represented by —S(G1), wherein G1 is the “aryl group” described in the specific example group G1. Unless otherwise specified, the ring-forming carbon number of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.
Specific examples of the "aralkyl group" described in the present specification are groups represented by -(G3)-(G1), wherein G3 is an "alkyl group" described in specific example group G3. , G1 are “aryl groups” described in Specific Example Group G1. Thus, an "aralkyl group" is an embodiment of a "substituted alkyl group," substituted with an "aryl group." The number of carbon atoms of the “unsubstituted aralkyl group” which is the “unsubstituted alkyl group” substituted with the “unsubstituted aryl group” is 7 to 50, preferably 7 unless otherwise specified in the present specification. -30, more preferably 7-18.
Specific examples of the “aralkyl group” include, for example, benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group. Group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2- Examples thereof include β-naphthylethyl group, 1-β-naphthylisopropyl group and 2-β-naphthylisopropyl group.
　本明細書に記載の置換もしくは無置換のアリール基は、本明細書に別途記載のない限り、好ましくはフェニル基、ｐ－ビフェニル基、ｍ－ビフェニル基、ｏ－ビフェニル基、ｐ－ターフェニル－４－イル基、ｐ－ターフェニル－３－イル基、ｐ－ターフェニル－２－イル基、ｍ－ターフェニル－４－イル基、ｍ－ターフェニル－３－イル基、ｍ－ターフェニル－２－イル基、ｏ－ターフェニル－４－イル基、ｏ－ターフェニル－３－イル基、ｏ－ターフェニル－２－イル基、１－ナフチル基、２－ナフチル基、アントリル基、フェナントリル基、ピレニル基、クリセニル基、トリフェニレニル基、フルオレニル基、９，９’－スピロビフルオレニル基、９，９－ジフェニルフルオレニル基等である。 Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl- group. 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, anthryl group, phenanthryl group , Pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, 9,9-diphenylfluorenyl group and the like.
　本明細書に記載の置換もしくは無置換の複素環基は、本明細書に別途記載のない限り、好ましくはピリジル基、ピリミジニル基、トリアジニル基、キノリル基、イソキノリル基、キナゾリニル基、ベンゾイミダゾリル基、フェナントロリニル基、カルバゾリル基（１－カルバゾリル基、２－カルバゾリル基、３－カルバゾリル基、４－カルバゾリル基、９－カルバゾリル基）、ベンゾカルバゾリル基、アザカルバゾリル基、ジアザカルバゾリル基、ジベンゾフラニル基、ナフトベンゾフラニル基、アザジベンゾフラニル基、ジアザジベンゾフラニル基、ジベンゾチオフェニル基、ナフトベンゾチオフェニル基、アザジベンゾチオフェニル基、ジアザジベンゾチオフェニル基、（９－フェニル）カルバゾリル基（（９－フェニル）カルバゾール－１－イル基、（９－フェニル）カルバゾール－２－イル基、（９－フェニル）カルバゾール－３－イル基、又は（９－フェニル）カルバゾール－４－イル基）、（９－ビフェニリル）カルバゾリル基、（９－フェニル）フェニルカルバゾリル基、ジフェニルカルバゾール－９－イル基、フェニルカルバゾール－９－イル基、フェニルトリアジニル基、ビフェニリルトリアジニル基、ジフェニルトリアジニル基、フェニルジベンゾフラニル基、フェニルジベンゾチオフェニル基、インドロカルバゾリル基、ピラジニル基、ピリダジニル基、キナゾリニル基、シンノリニル基、フタラジニル基、キノキサリニル基、ピロリル基、インドリル基、ピロロ［３，２，１－ｊｋ］カルバゾリル基、フラニル基、ベンゾフラニル基、チオフェニル基、ベンゾチオフェニル基、ピラゾリル基、イミダゾリル基、ベンズイミダゾリル基、トリアゾリル基、オキサゾリル基、ベンズオキサゾリル基、チアゾリル基、ベンゾチアゾリル基、イソチアゾリル基、ベンズイソチアゾリル基、チアジアゾリル基、イソオキサゾリル基、ベンズイソオキサゾリル基、ピロリジニル基、ピぺリジニル基、ピぺラジニル基、イミダゾリジニル基、インドロ［３，２，１－ｊｋ］カルバゾリル基、ジベンゾチオフェニル基等である。 The substituted or unsubstituted heterocyclic group described in the present specification, unless otherwise specified in the present specification, preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenyl group. Nantrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 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)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole- 4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazide Nyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, phenyldibenzothiophenyl group, indolocarbazolyl group, pyrazinyl group, pyridazinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group Group, pyrrolo[3,2,1-jk]carbazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group , Thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group, benzisoxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, indolo[3,2 , 1-jk]carbazolyl group, dibenzothiophenyl group and the like.
　上記ジベンゾフラニル基及びジベンゾチオフェニル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 Unless otherwise specified in this specification, the above-mentioned dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups.
Figure JPOXMLDOC01-appb-C000026
Figure JPOXMLDOC01-appb-C000026
　式（ＸＹ－７６）～（ＸＹ－７９）中、ＸＢは、酸素原子又は硫黄原子である。 In formulas (XY-76) to (XY-79), X B is an oxygen atom or a sulfur atom.
　本明細書に記載の置換もしくは無置換のアルキル基は、本明細書に別途記載のない限り、好ましくはメチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、ｔ－ブチル基等である。 Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group. Group etc.
　本明細書に記載の「置換もしくは無置換のアリーレン基」は、別途記載のない限り、上記「アリール基」を２価にした基をいう。「置換もしくは無置換のアリーレン基」の具体例（具体例群Ｇ１２）としては、具体例群Ｇ１に記載の「アリール基」を２価にした基等が挙げられる。すなわち、「置換もしくは無置換のアリーレン基」の具体例（具体例群Ｇ１２）としては、具体例群Ｇ１に記載の「アリール基」の環形成炭素に結合している１つの水素を除いた基である。 Unless otherwise specified, the “substituted or unsubstituted arylene group” described in the present specification means a divalent group of the above “aryl group”. Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include a divalent group of the “aryl group” described in specific example group G1. That is, as a specific example of the “substituted or unsubstituted arylene group” (specific example group G12), a group excluding one hydrogen bonded to the ring-forming carbon of the “aryl group” described in specific example group G1. Is.
　本明細書に記載の「置換もしくは無置換の２価の複素環基」の具体例（具体例群Ｇ１３）としては、具体例群Ｇ２に記載の「複素環基」を２価にした基等が挙げられる。すなわち、「置換もしくは無置換の２価の複素環基」の具体例（具体例群Ｇ１３）としては、具体例群Ｇ２に記載の「複素環基」の環形成原子に結合している１つの水素を除いた基である。 Specific examples of the “substituted or unsubstituted divalent heterocyclic group” described in the present specification (specific example group G13) are groups in which the “heterocyclic group” described in specific example group G2 is divalent. Is mentioned. That is, as a specific example of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13), one bonded to the ring-forming atom of the “heterocyclic group” described in specific example group G2 It is a group excluding hydrogen.
　本明細書に記載の「置換もしくは無置換のアルキレン基」の具体例（具体例群Ｇ１４）としては、具体例群Ｇ３に記載の「アルキル基」を２価にした基等が挙げられる。すなわち、「置換もしくは無置換のアルキレン基」の具体例（具体例群Ｇ１４）としては、具体例群Ｇ３に記載の「アルキル基」のアルカン構造を形成する炭素に結合している１つの水素を除いた基である。 Specific examples of the “substituted or unsubstituted alkylene group” (specific group G14) described in the present specification include groups in which the “alkyl group” described in specific group G3 is divalent. That is, as a specific example of the “substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen bonded to carbon forming the alkane structure of the “alkyl group” described in specific example group G3 is It is the removed group.
　本明細書に記載の置換もしくは無置換のアリーレン基は、本明細書に別途記載のない限り、好ましくは以下いずれかの基である。 The substituted or unsubstituted arylene group described in the present specification is preferably any of the following groups unless otherwise specified in the present specification.
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
　式（ＸＹ－２０）～（ＸＹ－２９）、（ＸＹ－８３）及び（ＸＹ－８４）中、Ｒ９０８は、置換基である。
　ｍ９０１は、０～４の整数であり、ｍ９０１が２以上のとき、複数存在するＲ９０８は互いに同一であってもよいし、異なっていてもよい。 In formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R 908 is a substituent.
m901 is an integer of 0 to 4, and when m901 is 2 or more, a plurality of R 908 s may be the same as or different from each other.
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028
　式（ＸＹ－３０）～（ＸＹ－４０）中、Ｒ９０９は、それぞれ独立に、水素原子、又は置換基である。２個のＲ９０９は、単結合を介して互いに結合して環を形成してもよい。 In formulas (XY-30) to (XY-40), each R 909 independently represents a hydrogen atom or a substituent. Two R 909 may be bonded to each other via a single bond to form a ring.
Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029
　式（ＸＹ－４１）～（ＸＹ－４６）中、Ｒ９１０は、置換基である。
　ｍ９０２は０～６の整数である。ｍ９０２が２以上のとき、複数存在するＲ９１０は互いに同一であってもよいし、異なっていてもよい。 In formulas (XY-41) to (XY-46), R 910 is a substituent.
m902 is an integer of 0 to 6. When m902 is 2 or more, a plurality of R 910s may be the same as or different from each other.
　本明細書に記載の置換もしくは無置換の２価の複素環基は、本明細書に別途記載のない限り、好ましくは以下いずれかの基である。 The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any of the following groups, unless otherwise specified in the present specification.
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
　式（ＸＹ－５０）～（ＸＹ－６０）中、Ｒ９１１は、水素原子、又は置換基である。 In formulas (XY-50) to (XY-60), R 911 is a hydrogen atom or a substituent.
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
　上記式（ＸＹ－６５）～（ＸＹ－７５）中、ＸＢは、酸素原子又は硫黄原子である。 In the above formulas (XY-65) to (XY-75), X B is an oxygen atom or a sulfur atom.
　本明細書において、「隣接する２つ以上の１組以上が、互いに結合して、置換もしくは無置換の飽和又は不飽和の環を形成する」場合について、母骨格がアントラセン環である下記式（ＸＹ－８０）で表されるアントラセン化合物の場合を例として説明する。 In the present specification, in the case where “two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring”, the following formula (wherein the mother skeleton is an anthracene ring) The case of an anthracene compound represented by XY-80) will be described as an example.
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
　例えば、Ｒ９２１～Ｒ９３０のうちの「隣接する２つ以上の１組以上が、互いに結合して、環を形成する」場合の１組となる隣接する２つとは、Ｒ９２１とＲ９２２、Ｒ９２２とＲ９２３、Ｒ９２３とＲ９２４、Ｒ９２４とＲ９３０、Ｒ９３０とＲ９２５、Ｒ９２５とＲ９２６、Ｒ９２６とＲ９２７、Ｒ９２７とＲ９２８、Ｒ９２８とＲ９２９、及びＲ９２９とＲ９２１である。 For example, in R 921 to R 930 , two adjacent groups that form a pair when “two or more groups adjacent to each other are bonded to each other to form a ring” are R 921 and R 922 , R 922 and R 923 , R 923 and R 924 , R 924 and R 930 , R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R. 929 and R 921 .
　上記「１組以上」とは、上記隣接する２つの２組以上が同時に環を形成してもよいことを意味する。例えば、Ｒ９２１とＲ９２２とが互いに結合して環Ａを形成し、同時にＲ９２５とＲ９２６とが互いに結合して環Ｂを形成した場合は、下記式（ＸＹ－８１）で表される。 The above-mentioned "one or more pairs" means that two adjacent two or more pairs may simultaneously form a ring. For example, when R 921 and R 922 are bonded to each other to form ring A and at the same time R 925 and R 926 are bonded to each other to form ring B, they are represented by the following formula (XY-81). ..
Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000033
　「隣接する２つ以上」が環を形成する場合とは、例えば、Ｒ９２１とＲ９２２とが互いに結合して環Ａを形成し、Ｒ９２２とＲ９２３とが互いに結合して環Ｃを形成し、Ｒ９２１～Ｒ９２３の互いに隣接する３つでアントラセン母骨格に縮合する、Ｒ９２２を共有する環Ａ及び環Ｃを形成した場合は、下記式（ＸＹ－８２）で表される。 When "two or more adjacent to each other" form a ring, for example, R 921 and R 922 are bonded to each other to form a ring A, and R 922 and R 923 are bonded to each other to form a ring C. In the case where the ring A and the ring C sharing R 922, which are fused to the anthracene mother skeleton by three adjacent R 921 to R 923 , are represented by the following formula (XY-82).
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-C000034
　上記式（ＸＹ－８１）及び（ＸＹ－８２）において形成された環Ａ～Ｃは、飽和又は不飽和の環である。
　「不飽和の環」とは、芳香族炭化水素環又は芳香族複素環を意味する。「飽和の環」とは、脂肪族炭化水素環又は脂肪族複素環を意味する。
　例えば、上記式（ＸＹ－８１）に示す、Ｒ９２１とＲ９２２が互いに結合して形成された環Ａは、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２が結合するアントラセン骨格の炭素原子と、１以上の任意の元素とで形成する環を意味する。具体例としては、Ｒ９２１とＲ９２２で環Ａを形成する場合において、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２が結合するアントラセン骨格の炭素原子と、４つの炭素原子とで不飽和の環を形成する場合、Ｒ９２１とＲ９２２とで形成する環はベンゼン環となる。また、飽和の環を形成する場合には、シクロヘキサン環となる。 Rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.
“Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocycle. The “saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocycle.
For example, the ring A formed by combining R 921 and R 922 with each other in the above formula (XY-81) is a carbon atom of the anthracene skeleton to which R 921 binds and a carbon atom of the anthracene skeleton to which R 922 binds. It means a ring formed by an atom and one or more arbitrary elements. As a specific example, when R 921 and R 922 form a ring A, a carbon atom of the anthracene skeleton to which R 921 binds, a carbon atom of the anthracene skeleton to which R 922 binds, and four carbon atoms When forming a saturated ring, the ring formed by R 921 and R 922 is a benzene ring. Moreover, when forming a saturated ring, it becomes a cyclohexane ring.
　ここで、「任意の元素」は、好ましくは、Ｃ元素、Ｎ元素、Ｏ元素、Ｓ元素である。任意の元素において（例えばＣ元素又はＮ元素の場合）、環形成に関与しない結合は、水素原子等で終端されてもよいし、任意の置換基で置換されてもよい。Ｃ元素以外の任意の元素を含む場合、形成される環は複素環となる。
　飽和又は不飽和の環を構成する「１以上の任意の元素」は、好ましくは２個以上１５個以下、より好ましくは３個以上１２個以下、さらに好ましくは、３個以上５個以下である。 Here, the "arbitrary element" is preferably a C element, an N element, an O element, or an S element. In any element (for example, in the case of C element or N element), a bond that does not participate in ring formation may be terminated with a hydrogen atom or the like, or may be substituted with any substituent. When it contains any element other than the C element, the ring formed is a heterocycle.
The “one or more arbitrary elements” forming the saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less. ..
　芳香族炭化水素環の具体例としては、具体例群Ｇ１において具体例として挙げられたアリール基が、水素原子で終端された構造が挙げられる。
　芳香族複素環の具体例としては、具体例群Ｇ２において具体例として挙げられた芳香族複素環基が、水素原子で終端された構造が挙げられる。
　脂肪族炭化水素環の具体例としては、具体例群Ｇ６において具体例として挙げられたシクロアルキル基が、水素原子で終端された構造が挙げられる。
　上記の「飽和又は不飽和の環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「飽和又は不飽和の環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。 Specific examples of the aromatic hydrocarbon ring include structures in which the aryl group mentioned as a specific example in the specific example group G1 is terminated by a hydrogen atom.
Specific examples of the aromatic heterocycle include a structure in which the aromatic heterocyclic group mentioned as a specific example in the specific example group G2 is terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the cycloalkyl group mentioned as a specific example in the specific example group G6 is terminated by a hydrogen atom.
When the above “saturated or unsaturated ring” has a substituent, the substituent is, for example, an “arbitrary substituent” described later. When the above “saturated or unsaturated ring” has a substituent, specific examples of the substituent are the substituents described in the above-mentioned “Substituents”.
　本明細書における一実施形態においては、前記「置換もしくは無置換の」という場合の置換基（以下、「任意の置換基」と呼ぶことがある。）は、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）
（ここで、
Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の１価の複素環基
からなる群から選択される基である。 In one embodiment of the present specification, the substituent in the case of “substituted or unsubstituted” (hereinafter, may be referred to as “optional substituent”) is
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 )
(here,
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ),
Halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
　一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the case of “substituted or unsubstituted” is
An alkyl group having 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
　一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の１価の複素環基
からなる群から選択される基である。 In one embodiment, the substituent in the case of “substituted or unsubstituted” is
An alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
　上記任意の置換基の各基の具体例は、上述した通りである。 Specific examples of each group of the above arbitrary substituents are as described above.
　本明細書において、特にことわらない限り、隣接する任意の置換基同士で、飽和又は不飽和の環（好ましくは、置換もしくは無置換の飽和もしくは不飽和の、５員環又は６員環、より好ましくは、ベンゼン環）を形成してもよい。
　本明細書において、特にことわらない限り、任意の置換基は、さらに置換基を有してもよい。任意の置換基がさらに有する置換基としては、上記任意の置換基と同様のものが挙げられる。 In the present specification, unless otherwise specified, a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5-membered ring or 6-membered ring, and Preferably, a benzene ring) may be formed.
In the present specification, unless otherwise specified, any substituent may further have a substituent. Examples of the substituent which the optional substituent further has are the same as the above-mentioned optional substituents.
［有機ＥＬ素子］
　本発明の第１の態様の有機ＥＬ素子は、陰極と、陽極と、前記陰極と前記陽極との間に有機層を有する有機エレクトロルミネッセンス素子であって、
　前記有機層が、下記式（１）で表される化合物と、下記式（１１－１）及び（１１－３）で表される化合物、又は下記式（１１－２）及び（１１－３）で表される化合物である、化合物Ａ（以下、式（１１）で表される化合物ということがある。）と、を含むことを特徴とする。 [Organic EL device]
The organic EL element of the first aspect of the present invention is a cathode, an anode, an organic electroluminescence element having an organic layer between the cathode and the anode,
The organic layer is a compound represented by the following formula (1) and a compound represented by the following formulas (11-1) and (11-3), or the following formulas (11-2) and (11-3) And a compound A (hereinafter, sometimes referred to as a compound represented by the formula (11)), which is a compound represented by.
Figure JPOXMLDOC01-appb-C000035
Figure JPOXMLDOC01-appb-C000035
　上記式（１）及び（１１－１）～（１１－３）中の各置換基については後述する。 Each substituent in the above formulas (1) and (11-1) to (11-3) will be described later.
　第１の態様の有機ＥＬ素子の概略構成を、図１を参照して説明する。
　第１の態様の有機ＥＬ素子１は、基板２と、陽極３と、発光層５と、陰極１０と、陽極３と発光層５との間にある有機層４と、発光層５と陰極１０との間にある有機層６とを有する。
　上記式（１）で表される化合物及び化合物Ａは、陽極３と陰極１０との間にある有機層４～６に含まれ、好ましくは発光層５に含まれる。
　上記有機層に含まれる、上記式（１）で表される化合物及び化合物Ａは、それぞれ１種単独であってもよいし、２種以上であってもよい。 A schematic configuration of the organic EL element of the first aspect will be described with reference to FIG.
The organic EL device 1 according to the first aspect 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, a light emitting layer 5 and a cathode 10. And an organic layer 6 between them.
The compound represented by the above formula (1) and the compound A are contained in the organic layers 4 to 6 between the anode 3 and the cathode 10, and preferably in the light emitting layer 5.
The compound represented by the above formula (1) and the compound A contained in the above organic layer may each be one kind alone or two or more kinds.
　式（１）中、Ｒ１～Ｒ８のうちの１個以上は、－Ｌ１３－Ａｒ１３である。即ち、式（１）のアントラセン化合物は、基－ＬＸ－ＡｒＸ（Ｘは１１、１２又は１３）が３個以上置換した構造を有している。（以下、式（１）で表される化合物を「３置換アントラセン化合物（１）」又は「３置換アントラセン系ホスト材料（１）」と呼ぶことがある。）
　上記基－ＬＸ－ＡｒＸに相当する置換基を２個有する従来のアントラセン系ホスト材料が知られている。（以下、これを「２置換アントラセン化合物」と呼ぶことがある。）
　本発明者らは、３置換アントラセン化合物（１）を発光層のホスト材料として用い、化合物Ａをドーパント材料として用いたところ、駆動電圧が低くなり、かつ、素子寿命が向上することを見出した。 In the formula (1), at least one of R 1 to R 8 is —L 13 —Ar 13 . That is, the anthracene compound of the formula (1) has a structure in which three or more groups -L X -Ar X (X is 11, 12 or 13) are substituted. (Hereinafter, the compound represented by the formula (1) may be referred to as “3-substituted anthracene compound (1)” or “3-substituted anthracene-based host material (1)”.)
Conventional anthracene-based host materials having two substituents corresponding to the above group -L X -Ar X are known. (Hereinafter, this may be referred to as a "disubstituted anthracene compound".)
The present inventors have found that when the 3-substituted anthracene compound (1) is used as the host material of the light emitting layer and the compound A is used as the dopant material, the driving voltage is lowered and the device life is improved.
　さらに、本発明者らは、３置換アントラセン系ホスト材料（１）及び化合物Ａを含む発光層に隣接する層を構成する材料との組合せも検討した。発光層に隣接する正孔阻止層に、後述する式（２０）、式（２１）で表される化合物（以下、アジン系正孔阻止層材料（２１）と呼ぶことがある。）又は式（３１）で表される化合物（以下、フルオランテン系正孔阻止層材料（３１）と呼ぶことがある。）を用いると、より優れた素子寿命の向上効果が得られることを見出した。
　また、上記発光層に隣接する電子阻止層に、式（４１）で表される化合物（以下、「モノアミン系電子阻止層材料（４１）」と呼ぶことがある。）又は式（５１）で表される化合物を用いると、さらに長寿命の有機ＥＬ素子が得られことも見出し、本発明を完成させた。 Furthermore, the present inventors also examined a combination with a tri-substituted anthracene-based host material (1) and a material forming a layer adjacent to the light emitting layer containing the compound A. In the hole blocking layer adjacent to the light emitting layer, the compound represented by the formula (20) or the formula (21) described below (hereinafter may be referred to as an azine-based hole blocking layer material (21)) or the formula ( It was found that the use of the compound represented by 31) (hereinafter sometimes referred to as the fluoranthene-based hole blocking layer material (31)) provides a more excellent effect of improving the device life.
In the electron blocking layer adjacent to the light emitting layer, the compound represented by the formula (41) (hereinafter, may be referred to as “monoamine-based electron blocking layer material (41)”) or the formula (51). It was also found that an organic EL device having a longer life can be obtained by using the compound described above, and the present invention has been completed.
　本発明の第２の態様の有機ＥＬ素子は、上記第１の態様の有機ＥＬ素子の一実施形態である、上記式（１）で表される化合物及び化合物Ａが発光層に含まれる有機ＥＬ素子において、
　前記有機層が、さらに、前記発光層に隣接する正孔阻止層を含み、
　前記正孔阻止層が、下記式（２０）、（２１）及び（３１）で表される化合物から選択される１以上の化合物を含むことを特徴とする。 The organic EL element of the second aspect of the present invention is an organic EL element in which the compound represented by the formula (1) and the compound A are contained in the light emitting layer, which is one embodiment of the organic EL element of the first aspect. In the element,
The organic layer further comprises a hole blocking layer adjacent to the light emitting layer,
The hole blocking layer is characterized by containing one or more compounds selected from compounds represented by the following formulas (20), (21) and (31).
Figure JPOXMLDOC01-appb-C000036
Figure JPOXMLDOC01-appb-C000036
　上記式（２０）、（２１）及び（３１）中の各置換基については後述する。 Each substituent in the above formulas (20), (21) and (31) will be described later.
　第２の態様の有機ＥＬ素子の概略構成を図２を参照して説明する。
　第２の態様の有機ＥＬ素子１ａは、基板２と、陽極３と、発光層５と、陰極１０と、陽極３と発光層５との間にある有機層４と、発光層５と陰極１０との間にある有機層６とを有し、発光層５と陰極１０との間にある有機層６のうち、発光層５に隣接する正孔阻止層６ａを有する。
　上記正孔阻止層に含まれる、上記式（２０）、（２１）及び（３１）で表される化合物は、それぞれ１種単独であってもよいし、２種以上であってもよい。 A schematic configuration of the organic EL element of the second aspect will be described with reference to FIG.
The organic EL element 1a according to the second aspect 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, a light emitting layer 5 and a cathode 10. And a hole blocking layer 6a adjacent to the light emitting layer 5 among the organic layers 6 between the light emitting layer 5 and the cathode 10.
The compounds represented by the formulas (20), (21) and (31) contained in the hole blocking layer may be one kind alone, or two or more kinds.
　本発明の第３の態様の有機ＥＬ素子は、上記第１の態様の有機ＥＬ素子の一実施形態である、上記式（１）で表される化合物及び化合物Ａが発光層に含まれる有機ＥＬ素子において、
　前記有機層が、さらに前記発光層に隣接する電子阻止層を含み、
　前記電子阻止層が、下記式（４１）で表される化合物、又は下記式（５１）で表される化合物を含むことを特徴とする。 The organic EL device of the third aspect of the present invention is an organic EL device in which the compound represented by the above formula (1) and the compound A are contained in the light emitting layer, which is one embodiment of the organic EL device of the first aspect. In the element,
The organic layer further includes an electron blocking layer adjacent to the light emitting layer,
The electron blocking layer contains a compound represented by the following formula (41) or a compound represented by the following formula (51).
Figure JPOXMLDOC01-appb-C000037
Figure JPOXMLDOC01-appb-C000037
　上記式（４１）及び（５１）中の各置換基については後述する。 Each substituent in the above formulas (41) and (51) will be described later.
　第３の態様の有機ＥＬ素子の概略構成を図３を参照して説明する。
　第３の態様の有機ＥＬ素子１ｂは、基板２と、陽極３と、発光層５と、陰極１０と、陽極３と発光層５との間にある有機層４と、発光層５と陰極１０との間にある有機層６とを有し、陽極３と発光層５との間にある有機層４のうち、発光層５に隣接する電子阻止層４ｂを有する。
　上記電子阻止層に含まれる、上記式（４１）で表される化合物及び上記式（５１）で表される化合物は、それぞれ１種単独であってもよいし、２種以上であってもよい。 A schematic configuration of the organic EL element of the third aspect will be described with reference to FIG.
The organic EL element 1b according to the third aspect 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, a light emitting layer 5 and a cathode 10. Of the organic layer 4 between the anode 3 and the light emitting layer 5, and an electron blocking layer 4b adjacent to the light emitting layer 5 among the organic layers 4 between the anode 3 and the light emitting layer 5.
The compound represented by the formula (41) and the compound represented by the formula (51) contained in the electron blocking layer may each be a single type or may be two or more types. ..
　本発明の第４の態様の有機ＥＬ素子においては、上記第１の態様の有機ＥＬ素子の一実施形態である、上記式（１）で表される化合物及び化合物Ａが発光層に含まれる有機ＥＬ素子において、
　前記有機層が、さらに、前記発光層に隣接する正孔阻止層を含み、
　前記正孔阻止層が、上記式（２０）、式（２１）及び式（３１）で表される化合物から選択される１以上の化合物を含み、
　前記有機層が、さらに前記発光層に隣接する電子阻止層を含み、
　前記電子阻止層が、上記式（４１）で表される化合物、又は上記式（５１）で表される化合物を含むことを特徴とする。 In the organic EL device according to the fourth aspect of the present invention, the organic EL device according to the first aspect is an organic EL device in which the compound represented by the formula (1) and the compound A are contained in the light emitting layer. In EL element,
The organic layer further comprises a hole blocking layer adjacent to the light emitting layer,
The hole blocking layer contains one or more compounds selected from the compounds represented by the above formulas (20), (21) and (31),
The organic layer further includes an electron blocking layer adjacent to the light emitting layer,
The electron blocking layer contains a compound represented by the above formula (41) or a compound represented by the above formula (51).
　本発明の第４の態様の有機ＥＬ素子を、図４を参照して説明する。
　第１～第３の態様の有機ＥＬ素子の一実施形態である第４の態様の有機ＥＬ素子１ｃは、基板２と、陽極３と、発光層５と、陰極１０と、陽極３と発光層５との間にある有機層４と、発光層５と陰極１０との間にある有機層６とを有し、発光層５と陰極１０との間にある有機層６のうち、発光層５に隣接する正孔阻止層６ａ、及び陽極３と発光層５との間にある有機層４のうち、発光層５に隣接する電子阻止層４ｂを有する。 The organic EL element of the fourth aspect of the present invention will be described with reference to FIG.
An organic EL element 1c of a fourth aspect, which is one embodiment of the organic EL elements of the first to third aspects, has a substrate 2, an anode 3, a light emitting layer 5, a cathode 10, an anode 3 and a light emitting layer. The organic layer 4 between the light emitting layer 5 and the cathode 10 and the organic layer 6 between the light emitting layer 5 and the cathode 10. Of the organic layer 4 between the anode 3 and the light emitting layer 5 and the electron blocking layer 4b adjacent to the light emitting layer 5.
　有機層が、発光層５、正孔阻止層６ａ及び電子阻止層４ｂを含み、各層に特定の化合物を含むことによって、素子寿命の向上効果が得られる。 The organic layer includes the light emitting layer 5, the hole blocking layer 6a, and the electron blocking layer 4b, and when each layer contains a specific compound, the effect of improving the device life can be obtained.
　本発明の第５の態様に係る有機ＥＬ素子は、２以上の発光層を有する、いわゆるタンデム型の構成を有する。このようなタンデム型構造を有することにより、簡素な構造の白色発光素子を製造することができる。 The organic EL element according to the fifth aspect of the present invention has a so-called tandem type structure having two or more light emitting layers. By having such a tandem structure, a white light emitting element having a simple structure can be manufactured.
　本発明の一態様に係る有機ＥＬ素子は、例えば、蛍光又は燐光発光型の単色発光素子であってもよく、蛍光／燐光ハイブリッド型の白色発光素子であってもよい。また、単独の発光ユニットを有するシンプル型であってもよく、複数の発光ユニットを有するタンデム型であってもよい。
　ここで、「発光ユニット」とは、有機層を含み、該有機層のうちの少なくとも１層が発光層であり、注入された正孔と電子が再結合することにより発光する最小単位を言う。
　また、本明細書に記載の「発光層」とは、発光機能を有する有機層である。発光層は、例えば、燐光発光層、蛍光発光層等であり、また、１層でも複数層でもよい。
　発光ユニットは、燐光発光層や蛍光発光層を複数有する積層型であってもよく、この場合、例えば、燐光発光層で生成された励起子が蛍光発光層に拡散することを防ぐためのスペース層を各発光層の間に有していてもよい。 The organic EL element according to one aspect of the present invention may be, for example, a fluorescent or phosphorescent type monochromatic light emitting element, or a fluorescent/phosphorescent hybrid type white light emitting element. Further, it may be a simple type having a single light emitting unit or a tandem type having a plurality of light emitting units.
Here, the “light emitting unit” refers to a minimum unit that includes an organic layer, at least one of the organic layers is a light emitting layer, and emits light by recombination of injected holes and electrons.
Further, the “light emitting layer” described in the present specification is an organic layer having a light emitting function. The light emitting layer is, for example, a phosphorescent light emitting layer, a fluorescent light emitting layer, or the like, and may be a single layer or a plurality of layers.
The light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers or fluorescent light emitting layers. In this case, for example, a space layer for preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. May be provided between each light emitting layer.
　シンプル型有機ＥＬ素子としては、例えば、陽極／発光ユニット／陰極のような素子構成が挙げられる。
　発光ユニットの代表的な層構成を以下に示す。カッコ内の層は任意である。
（ａ）（正孔注入層／）正孔輸送層／蛍光発光層（／電子輸送層／電子注入層）
（ｂ）（正孔注入層／）正孔輸送層／燐光発光層（／電子輸送層／電子注入層）
（ｃ）（正孔注入層／）正孔輸送層／第１蛍光発光層／第２蛍光発光層（／電子輸送層／電子注入層）
（ｄ）（正孔注入層／）正孔輸送層／第１燐光発光層／第２燐光発光層（／電子輸送層／電子注入層）（ｅ）（正孔注入層／）正孔輸送層／燐光発光層／スペース層／蛍光発光層（／電子輸送層／電子注入層）
（ｆ）（正孔注入層／）正孔輸送層／第１燐光発光層／第２燐光発光層／スペース層／蛍光発光層（／電子輸送層／電子注入層）
（ｇ）（正孔注入層／）正孔輸送層／第１燐光発光層／スペース層／第２燐光発光層／スペース層／蛍光発光層（／電子輸送層／電子注入層）
（ｈ）（正孔注入層／）正孔輸送層／燐光発光層／スペース層／第１蛍光発光層／第２蛍光発光層（／電子輸送層／電子注入層）
（ｉ）（正孔注入層／）正孔輸送層／電子阻止層／蛍光発光層（／電子輸送層／電子注入層）
（ｊ）（正孔注入層／）正孔輸送層／電子阻止層／燐光発光層（／電子輸送層／電子注入層）
（ｋ）（正孔注入層／）正孔輸送層／励起子阻止層／蛍光発光層（／電子輸送層／電子注入層）
（ｌ）（正孔注入層／）正孔輸送層／励起子阻止層／燐光発光層（／電子輸送層／電子注入層）
（ｍ）（正孔注入層／）第１正孔輸送層／第２正孔輸送層／蛍光発光層（／電子輸送層／電子注入層）
（ｎ）（正孔注入層／）第１正孔輸送層／第２正孔輸送層／蛍光発光層（／第１電子輸送層／第２電子輸送層／電子注入層）
（ｏ）（正孔注入層／）第１正孔輸送層／第２正孔輸送層／燐光発光層（／電子輸送層／電子注入層）
（ｐ）（正孔注入層／）第１正孔輸送層／第２正孔輸送層／燐光発光層（／第１電子輸送層／第２電子輸送層／電子注入層）
（ｑ）（正孔注入層／）正孔輸送層／蛍光発光層／正孔阻止層（／電子輸送層／電子注入層）
（ｒ）（正孔注入層／）正孔輸送層／燐光発光層／正孔阻止層（／電子輸送層／電子注入層）
（ｓ）（正孔注入層／）正孔輸送層／蛍光発光層／励起子阻止層（／電子輸送層／電子注入層）
（ｔ）（正孔注入層／）正孔輸送層／燐光発光層／励起子阻止層（／電子輸送層／電子注入層） Examples of the simple type organic EL element include element configurations such as anode/light emitting unit/cathode.
A typical layer structure of the light emitting unit is shown below. Layers in parentheses are optional.
(A) (hole injection layer/) hole transport layer/fluorescent emission layer (/electron transport layer/electron injection layer)
(B) (hole injection layer/) hole transport layer/phosphorescence emitting layer (/electron transport layer/electron injection layer)
(C) (hole injection layer/) hole transport layer/first fluorescent light emitting layer/second fluorescent light emitting layer (/electron transport layer/electron injection layer)
(D) (hole injection layer/) hole transport layer/first phosphorescent light emitting layer/second phosphorescent light emitting layer (/electron transport layer/electron injection layer) (e) (hole injection layer/)hole transport layer /Phosphorescent layer/Space layer/Fluorescent layer (/Electron transport layer/Electron injection layer)
(F) (hole injection layer/) hole transport layer/first phosphorescent light emitting layer/second phosphorescent light emitting layer/space layer/fluorescent light emitting layer (/electron transport layer/electron injection layer)
(G) (hole injection layer/) hole transport layer/first phosphorescent light emitting layer/space layer/second phosphorescent light emitting layer/space layer/fluorescent light emitting layer (/electron transport layer/electron injection layer)
(H) (hole injecting layer/) hole transporting layer/phosphorescent emitting layer/space layer/first fluorescent emitting layer/second fluorescent emitting layer (/electron transporting layer/electron injecting layer)
(I) (Hole injection layer/) Hole transport layer/Electron blocking layer/Fluorescent emission layer (/Electron transport layer/Electron injection layer)
(J) (Hole injection layer/) Hole transport layer/Electron blocking layer/Phosphorescent layer (/Electron transport layer/Electron injection layer)
(K) (hole injection layer/) hole transport layer/exciton block layer/fluorescent emission layer (/electron transport layer/electron injection layer)
(L) (hole injecting layer/) hole transporting layer/exciton blocking layer/phosphorescent emitting layer (/electron transporting layer/electron injecting layer)
(M) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent light emitting layer (/electron transport layer/electron injection layer)
(N) (hole injection layer/)first hole transport layer/second hole transport layer/fluorescent emission layer (/first electron transport layer/second electron transport layer/electron injection layer)
(O) (hole injection layer/) first hole transport layer/second hole transport layer/phosphorescent emitting layer (/electron transport layer/electron injection layer)
(P) (Hole injection layer/) First hole transport layer/Second hole transport layer/Phosphorescent layer (/First electron transport layer/Second electron transport layer/Electron injection layer)
(Q) (hole injection layer/) hole transport layer/fluorescent emission layer/hole blocking layer (/electron transport layer/electron injection layer)
(R) (hole injection layer/) hole transport layer/phosphorescence emitting layer/hole blocking layer (/electron transport layer/electron injection layer)
(S) (hole injection layer/) hole transport layer/fluorescent emission layer/exciton blocking layer (/electron transport layer/electron injection layer)
(T) (hole injection layer/) hole transport layer/phosphorescence emitting layer/exciton blocking layer (/electron transport layer/electron injection layer)
　ただし、本発明の一態様に係る有機ＥＬ素子の層構成は、これらに限定されるものではない。例えば、有機ＥＬ素子が、正孔注入層及び正孔輸送層を有する場合には、正孔輸送層と陽極との間に正孔注入層が設けられていることが好ましい。また、有機ＥＬ素子が、電子注入層及び電子輸送層を有する場合には、電子輸送層と陰極との間に電子注入層が設けられていることが好ましい。また、正孔注入層、正孔輸送層、電子輸送層、及び電子注入層のそれぞれは、１層で構成されていてもよく、複数の層で構成されていてもよい。 However, the layer structure of the organic EL element according to one embodiment of the present invention is not limited to these. For example, when the organic EL element has a hole injection layer and a hole transport layer, it is preferable that the hole injection layer is provided between the hole transport layer and the anode. Further, when the organic EL element has an electron injection layer and an electron transport layer, it is preferable that the electron injection layer is provided between the electron transport layer and the cathode. Moreover, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer or may be composed of a plurality of layers.
　複数の燐光発光層、及び、燐光発光層と蛍光発光層は、それぞれ互いに異なる色の発光層であってもよい。例えば、前記発光ユニット（ｆ）は、正孔輸送層／第１燐光発光層（赤色発光）／第２燐光発光層（緑色発光）／スペース層／蛍光発光層（青色発光）／電子輸送層とすることもできる。
　尚、各発光層と、正孔輸送層又はスペース層との間に、電子阻止層を設けてもよい。また、各発光層と電子輸送層との間に、正孔阻止層を設けてもよい。電子阻止層や正孔阻止層を設けることにより、電子又は正孔を発光層内に閉じ込めて、発光層における電荷の再結合確率を高め、発光効率を向上させることができる。 The plurality of phosphorescent light emitting layers, and the phosphorescent light emitting layer and the fluorescent light emitting layer may be light emitting layers of mutually different colors. For example, the light emitting unit (f) includes a hole transport layer/first phosphorescent light emitting layer (red light emission)/second phosphorescent light emitting layer (green light emission)/space layer/fluorescent light emitting layer (blue light emission)/electron transport layer. You can also do it.
An electron blocking layer may be provided between each light emitting layer and the hole transport layer or the space layer. Further, a hole blocking layer may be provided between each light emitting layer and the electron transport layer. By providing the electron blocking layer or the hole blocking layer, electrons or holes can be confined in the light emitting layer, the probability of recombination of charges in the light emitting layer can be increased, and the light emission efficiency can be improved.
　タンデム型有機ＥＬ素子の代表的な素子構成としては、例えば、陽極／第１発光ユニット／中間層／第２発光ユニット／陰極のような素子構成が挙げられる。
　第１発光ユニット及び第２発光ユニットは、例えば、それぞれ独立に、上述した発光ユニットから選択することができる。
　中間層は、一般的に、中間電極、中間導電層、電荷発生層、電子引抜層、接続層、コネクター層、又は中間絶縁層とも呼ばれる。中間層は、第１発光ユニットに電子を、第２発光ユニットに正孔を供給する層であり、公知の材料により形成することができる。 As a typical element structure of the tandem type organic EL element, for example, an element structure such as anode/first light emitting unit/intermediate layer/second light emitting unit/cathode can be mentioned.
The first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units, for example.
The intermediate layer is also generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, a connector layer, or an intermediate insulation layer. The intermediate layer is a layer that supplies electrons to the first light emitting unit and holes to the second light emitting unit, and can be formed of a known material.
　本発明の第５の態様に係る有機ＥＬ素子の一実施形態の概略構成を、図５を参照して説明する。
　図５に示す、本発明の第５の態様に係る有機ＥＬ素子１ｄは、基板２と、陽極３と、陰極１０と、陽極３と陰極１０との間に有機層を有する。該有機層は、第１の発光ユニット５Ａと、第１の発光ユニット５Ａと陰極１０との間にある第２の発光ユニット５Ｂと、陽極３と第１の発光ユニット５Ａとの間にある有機層４ａと、第２の発光ユニット５Ｂと陰極１０との間にある有機層６ｂとを有する。第１の発光ユニット５Ａと第２の発光ユニット５Ｂの間に電荷発生層８を有する。
　以下、式（１）、（１１）、（２０）、（２１）、（３１）、（４１）及び（５１）で表される化合物について説明する。 A schematic configuration of an embodiment of the organic EL element according to the fifth aspect of the present invention will be described with reference to FIG.
The organic EL element 1d according to the fifth aspect of the present invention shown in FIG. 5 has a substrate 2, an anode 3, a cathode 10, and an organic layer between the anode 3 and the cathode 10. The organic layer includes a first light emitting unit 5A, a second light emitting unit 5B between the first light emitting unit 5A and the cathode 10, and an organic layer between the anode 3 and the first light emitting unit 5A. It has a layer 4a and an organic layer 6b between the second light emitting unit 5B and the cathode 10. The charge generation layer 8 is provided between the first light emitting unit 5A and the second light emitting unit 5B.
Hereinafter, the compounds represented by formulas (1), (11), (20), (21), (31), (41) and (51) will be described.
（式（１）で表される化合物）
　下記式（１）で表される化合物は、有機層に含まれる。好ましくは発光層に含まれる。
Figure JPOXMLDOC01-appb-C000038
 (Compound represented by Formula (1))
The compound represented by the following formula (1) is contained in the organic layer. It is preferably contained in the light emitting layer.
Figure JPOXMLDOC01-appb-C000038
［式（１）中、
　Ｒ１～Ｒ８のうちの１個以上は、－Ｌ１３－Ａｒ１３である。
　Ｌ１１～Ｌ１３は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　Ｌ１３が２個以上存在する場合、２個以上のＬ１３は、互いに同一であってもよいし、異なっていてもよい。
　Ａｒ１１～Ａｒ１３は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ａｒ１３が２個以上存在する場合、２個以上のＡｒ１３は、互いに同一であってもよいし、異なっていてもよい。
　－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］ [In Formula (1),
At least one of R 1 to R 8 is —L 13 —Ar 13 .
L 11 to L 13 are each independently
Single bond,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
When two or more L 13's are present, the two or more L 13 's may be the same as or different from each other.
Ar 11 to Ar 13 are each independently
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
When two or more Ar 13's are present, the two or more Ar 13 's may be the same or different from each other.
R 1 to R 8 which are not —L 13 —Ar 13 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
　一実施形態においては、－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、又はニトロ基である。 In one embodiment, R 1 to R 8 that are not —L 13 —Ar 13 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
It is a halogen atom, a cyano group, or a nitro group.
　尚、－Ｌ１１－Ａｒ１１、－Ｌ１２－Ａｒ１２、－Ｌ１３－Ａｒ１３、及び－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８は、互いに結合して、アントラセン環に縮合する環を形成しない。 R 1 to R 8 which are not -L 11 -Ar 11 , -L 12 -Ar 12 , -L 13 -Ar 13 and -L 13 -Ar 13 are bonded to each other to form an anthracene ring. Does not form.
　一実施形態においては、前記式（１）におけるＬ１１～Ｌ１３が、それぞれ独立に、単結合、又は
置換もしくは無置換の環形成炭素数６～５０のアリーレン基である。 In one embodiment, L 11 to L 13 in formula (1) are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
　一実施形態においては、前記式（１）におけるＬ１１～Ｌ１３が、それぞれ独立に、単結合、又は
置換もしくは無置換のフェニレン基、
置換もしくは無置換のビフェニレン基、
置換もしくは無置換のターフェニレン基、
置換もしくは無置換のクオーターフェニレン基、及び
置換もしくは無置換のナフチレン基からなる群から選択される基である。 In one embodiment, L 11 to L 13 in the formula (1) are each independently a single bond, or a substituted or unsubstituted phenylene group,
A substituted or unsubstituted biphenylene group,
A substituted or unsubstituted terphenylene group,
It is a group selected from the group consisting of a substituted or unsubstituted quarter phenylene group and a substituted or unsubstituted naphthylene group.
　一実施形態においては、前記式（１）におけるＡｒ１１～Ａｒ１３が、それぞれ独立に、置換もしくは無置換の環形成炭素数６～３０のアリール基である。 In one embodiment, Ar 11 to Ar 13 in the formula (1) are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
　一実施形態においては、前記式（１）におけるＡｒ１１～Ａｒ１３が、それぞれ独立に、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換の９，９’－スピロビフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のフェナントリル基、及び
置換もしくは無置換のベンゾフェナントリル基からなる群さら選択される。 In one embodiment, Ar 11 to Ar 13 in the formula (1) are each independently
A substituted or unsubstituted phenyl group,
A substituted or unsubstituted naphthyl group,
A substituted or unsubstituted fluorenyl group,
A substituted or unsubstituted 9,9′-spirobifluorenyl group,
A substituted or unsubstituted benzofluorenyl group,
A group consisting of a substituted or unsubstituted phenanthryl group and a substituted or unsubstituted benzophenanthryl group is further selected.
　一実施形態においては、前記式（１）におけるＡｒ１１～Ａｒ１３のうちの１個以上が、それぞれ独立に、置換もしくは無置換の環形成原子数５～３０の１価の複素環基である。 In one embodiment, at least one of Ar 11 to Ar 13 in the above formula (1) is independently a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms. ..
　一実施形態においては、前記式（１）における－Ｌ１３－Ａｒ１３で表される基が、
置換もしくは無置換のフェニル基、
置換もしくは無置換のナフチル基、
置換もしくは無置換のビフェニル基、
置換もしくは無置換のフェナントレニル基、
置換もしくは無置換のベンゾフェナントレニル基、
置換もしくは無置換のフルオレニル基、
置換もしくは無置換のベンゾフルオレニル基、
置換もしくは無置換のジベンゾフラニル基、
置換もしくは無置換のナフトベンゾフラニル基、
置換もしくは無置換のジベンゾチオフェニル基、及び
置換もしくは無置換のカルバゾリル基からなる群から選択される。 In one embodiment, the group represented by -L 13 -Ar 13 in the above formula (1) is
A substituted or unsubstituted phenyl group,
A substituted or unsubstituted naphthyl group,
A substituted or unsubstituted biphenyl group,
A substituted or unsubstituted phenanthrenyl group,
A substituted or unsubstituted benzophenanthrenyl group,
A substituted or unsubstituted fluorenyl group,
A substituted or unsubstituted benzofluorenyl group,
A substituted or unsubstituted dibenzofuranyl group,
A substituted or unsubstituted naphthobenzofuranyl group,
It is selected from the group consisting of a substituted or unsubstituted dibenzothiophenyl group and a substituted or unsubstituted carbazolyl group.
　一実施形態においては、前記式（１）で表される化合物が、下記式（１－１）で表される化合物である。 In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-1).
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-C000039
［式（１－１）中、Ｌ１１～Ｌ１３、Ａｒ１１～Ａｒ１３、Ｒ１、Ｒ３～Ｒ８は、前記式（１）で定義したとおりである。］ [In the formula (1-1), L 11 to L 13 , Ar 11 to Ar 13 , R 1 , and R 3 to R 8 are as defined in the above formula (1). ]
　一実施形態においては、前記式（１）で表される化合物が、下記式（１－１Ｈ）で表される化合物である。 In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-1H).
Figure JPOXMLDOC01-appb-C000040
Figure JPOXMLDOC01-appb-C000040
［式（１－１Ｈ）中、Ｌ１１～Ｌ１３及びＡｒ１１～Ａｒ１３は、前記式（１）で定義したとおりである。］ [In the formula (1-1H), L 11 to L 13 and Ar 11 to Ar 13 are as defined in the formula (1). ]
　一実施形態においては、前記式（１）で表される化合物が、下記式（１－２）～は（１－４）で表される化合物からなる群から選択される。 In one embodiment, the compound represented by the above formula (1) is selected from the group consisting of compounds represented by the following formulas (1-2) to (1-4).
Figure JPOXMLDOC01-appb-C000041
Figure JPOXMLDOC01-appb-C000041
［式（１－２）～（１－４）中、Ｌ１１、Ｌ１２、Ａｒ１１、Ａｒ１２、Ｒ１、Ｒ３～Ｒ８は、前記式（１）で定義したとおりである。］ [In the formulas (1-2) to (1-4), L 11 , L 12 , Ar 11 , Ar 12 , R 1 and R 3 to R 8 are as defined in the formula (1). ]
　一実施形態においては、前記式（１）における－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８が、水素原子である。 In one embodiment, R 1 to R 8 other than —L 13 —Ar 13 in the above formula (1) are hydrogen atoms.
　上記式（１）における各置換基の詳細は、本明細書の［定義］の欄に記載のとおりである。以下、上記式（１１）、（２０）、（２１）、（３１）、（４１）及び（５１）における各置換基についても同様である。 Details of each substituent in the above formula (1) are as described in the [Definition] column of this specification. The same applies to each substituent in the above formulas (11), (20), (21), (31), (41) and (51).
　以下に、式（１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（１）で表される化合物は下記具体例に限定されるものではない。 Specific examples of the compound represented by the formula (1) will be described below, but these are merely examples, and the compound represented by the formula (1) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000042
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000043
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000044
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000045
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000047
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000048
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000049
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000050
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000062
Figure JPOXMLDOC01-appb-C000062
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000064
Figure JPOXMLDOC01-appb-C000064
Figure JPOXMLDOC01-appb-C000065
Figure JPOXMLDOC01-appb-C000065
Figure JPOXMLDOC01-appb-C000066
Figure JPOXMLDOC01-appb-C000066
Figure JPOXMLDOC01-appb-C000067
Figure JPOXMLDOC01-appb-C000067
Figure JPOXMLDOC01-appb-C000068
Figure JPOXMLDOC01-appb-C000068
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-C000072
Figure JPOXMLDOC01-appb-C000072
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000075
Figure JPOXMLDOC01-appb-C000075
Figure JPOXMLDOC01-appb-C000076
Figure JPOXMLDOC01-appb-C000076
Figure JPOXMLDOC01-appb-C000077
Figure JPOXMLDOC01-appb-C000077
Figure JPOXMLDOC01-appb-C000078
Figure JPOXMLDOC01-appb-C000078
Figure JPOXMLDOC01-appb-C000079
Figure JPOXMLDOC01-appb-C000079
Figure JPOXMLDOC01-appb-C000080
Figure JPOXMLDOC01-appb-C000080
Figure JPOXMLDOC01-appb-C000081
Figure JPOXMLDOC01-appb-C000081
Figure JPOXMLDOC01-appb-C000082
Figure JPOXMLDOC01-appb-C000082
Figure JPOXMLDOC01-appb-C000083
Figure JPOXMLDOC01-appb-C000083
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-C000085
Figure JPOXMLDOC01-appb-C000085
Figure JPOXMLDOC01-appb-C000086
Figure JPOXMLDOC01-appb-C000086
Figure JPOXMLDOC01-appb-C000087
Figure JPOXMLDOC01-appb-C000087
Figure JPOXMLDOC01-appb-C000088
Figure JPOXMLDOC01-appb-C000088
Figure JPOXMLDOC01-appb-C000089
Figure JPOXMLDOC01-appb-C000089
Figure JPOXMLDOC01-appb-C000090
Figure JPOXMLDOC01-appb-C000090
Figure JPOXMLDOC01-appb-C000091
Figure JPOXMLDOC01-appb-C000091
Figure JPOXMLDOC01-appb-C000092
Figure JPOXMLDOC01-appb-C000092
Figure JPOXMLDOC01-appb-C000093
Figure JPOXMLDOC01-appb-C000093
Figure JPOXMLDOC01-appb-C000094
Figure JPOXMLDOC01-appb-C000094
Figure JPOXMLDOC01-appb-C000095
Figure JPOXMLDOC01-appb-C000095
Figure JPOXMLDOC01-appb-C000096
Figure JPOXMLDOC01-appb-C000096
Figure JPOXMLDOC01-appb-C000097
Figure JPOXMLDOC01-appb-C000097
Figure JPOXMLDOC01-appb-C000098
Figure JPOXMLDOC01-appb-C000098
Figure JPOXMLDOC01-appb-C000099
Figure JPOXMLDOC01-appb-C000099
Figure JPOXMLDOC01-appb-C000100
Figure JPOXMLDOC01-appb-C000100
Figure JPOXMLDOC01-appb-C000101
Figure JPOXMLDOC01-appb-C000101
Figure JPOXMLDOC01-appb-C000102
Figure JPOXMLDOC01-appb-C000102
Figure JPOXMLDOC01-appb-C000103
Figure JPOXMLDOC01-appb-C000103
Figure JPOXMLDOC01-appb-C000104
Figure JPOXMLDOC01-appb-C000104
Figure JPOXMLDOC01-appb-C000105
Figure JPOXMLDOC01-appb-C000105
Figure JPOXMLDOC01-appb-C000106
Figure JPOXMLDOC01-appb-C000106
Figure JPOXMLDOC01-appb-C000107
Figure JPOXMLDOC01-appb-C000107
Figure JPOXMLDOC01-appb-C000108
Figure JPOXMLDOC01-appb-C000108
Figure JPOXMLDOC01-appb-C000109
Figure JPOXMLDOC01-appb-C000109
Figure JPOXMLDOC01-appb-C000110
Figure JPOXMLDOC01-appb-C000110
Figure JPOXMLDOC01-appb-C000111
Figure JPOXMLDOC01-appb-C000111
Figure JPOXMLDOC01-appb-C000112
Figure JPOXMLDOC01-appb-C000112
Figure JPOXMLDOC01-appb-C000113
Figure JPOXMLDOC01-appb-C000113
Figure JPOXMLDOC01-appb-C000114
Figure JPOXMLDOC01-appb-C000114
Figure JPOXMLDOC01-appb-C000115
Figure JPOXMLDOC01-appb-C000115
Figure JPOXMLDOC01-appb-C000116
Figure JPOXMLDOC01-appb-C000116
Figure JPOXMLDOC01-appb-C000117
Figure JPOXMLDOC01-appb-C000117
Figure JPOXMLDOC01-appb-C000118
Figure JPOXMLDOC01-appb-C000118
Figure JPOXMLDOC01-appb-C000119
Figure JPOXMLDOC01-appb-C000119
Figure JPOXMLDOC01-appb-C000120
Figure JPOXMLDOC01-appb-C000120
Figure JPOXMLDOC01-appb-C000121
Figure JPOXMLDOC01-appb-C000121
Figure JPOXMLDOC01-appb-C000122
Figure JPOXMLDOC01-appb-C000122
Figure JPOXMLDOC01-appb-C000123
Figure JPOXMLDOC01-appb-C000123
Figure JPOXMLDOC01-appb-C000124
Figure JPOXMLDOC01-appb-C000124
Figure JPOXMLDOC01-appb-C000125
Figure JPOXMLDOC01-appb-C000125
Figure JPOXMLDOC01-appb-C000126
Figure JPOXMLDOC01-appb-C000126
Figure JPOXMLDOC01-appb-C000127
Figure JPOXMLDOC01-appb-C000127
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-C000129
Figure JPOXMLDOC01-appb-C000129
Figure JPOXMLDOC01-appb-C000130
Figure JPOXMLDOC01-appb-C000130
Figure JPOXMLDOC01-appb-C000131
Figure JPOXMLDOC01-appb-C000131
Figure JPOXMLDOC01-appb-C000132
Figure JPOXMLDOC01-appb-C000132
Figure JPOXMLDOC01-appb-C000133
Figure JPOXMLDOC01-appb-C000133
Figure JPOXMLDOC01-appb-C000134
Figure JPOXMLDOC01-appb-C000134
Figure JPOXMLDOC01-appb-C000135
Figure JPOXMLDOC01-appb-C000135
Figure JPOXMLDOC01-appb-C000136
Figure JPOXMLDOC01-appb-C000136
Figure JPOXMLDOC01-appb-C000137
Figure JPOXMLDOC01-appb-C000137
Figure JPOXMLDOC01-appb-C000138
Figure JPOXMLDOC01-appb-C000138
Figure JPOXMLDOC01-appb-C000139
Figure JPOXMLDOC01-appb-C000139
Figure JPOXMLDOC01-appb-C000140
Figure JPOXMLDOC01-appb-C000140
Figure JPOXMLDOC01-appb-C000141
Figure JPOXMLDOC01-appb-C000141
Figure JPOXMLDOC01-appb-C000142
Figure JPOXMLDOC01-appb-C000142
Figure JPOXMLDOC01-appb-C000143
Figure JPOXMLDOC01-appb-C000143
Figure JPOXMLDOC01-appb-C000144
Figure JPOXMLDOC01-appb-C000144
Figure JPOXMLDOC01-appb-C000145
Figure JPOXMLDOC01-appb-C000145
Figure JPOXMLDOC01-appb-C000146
Figure JPOXMLDOC01-appb-C000146
Figure JPOXMLDOC01-appb-C000147
Figure JPOXMLDOC01-appb-C000147
Figure JPOXMLDOC01-appb-C000148
Figure JPOXMLDOC01-appb-C000148
Figure JPOXMLDOC01-appb-C000149
Figure JPOXMLDOC01-appb-C000149
Figure JPOXMLDOC01-appb-C000150
Figure JPOXMLDOC01-appb-C000150
Figure JPOXMLDOC01-appb-C000151
Figure JPOXMLDOC01-appb-C000151
Figure JPOXMLDOC01-appb-C000152
Figure JPOXMLDOC01-appb-C000152
Figure JPOXMLDOC01-appb-C000153
Figure JPOXMLDOC01-appb-C000153
Figure JPOXMLDOC01-appb-C000154
Figure JPOXMLDOC01-appb-C000154
Figure JPOXMLDOC01-appb-C000155
Figure JPOXMLDOC01-appb-C000155
Figure JPOXMLDOC01-appb-C000156
Figure JPOXMLDOC01-appb-C000156
Figure JPOXMLDOC01-appb-C000157
Figure JPOXMLDOC01-appb-C000157
Figure JPOXMLDOC01-appb-C000158
Figure JPOXMLDOC01-appb-C000158
Figure JPOXMLDOC01-appb-C000159
Figure JPOXMLDOC01-appb-C000159
Figure JPOXMLDOC01-appb-C000160
Figure JPOXMLDOC01-appb-C000160
Figure JPOXMLDOC01-appb-C000161
Figure JPOXMLDOC01-appb-C000161
Figure JPOXMLDOC01-appb-C000162
Figure JPOXMLDOC01-appb-C000162
Figure JPOXMLDOC01-appb-C000163
Figure JPOXMLDOC01-appb-C000163
Figure JPOXMLDOC01-appb-C000164
Figure JPOXMLDOC01-appb-C000164
Figure JPOXMLDOC01-appb-C000165
Figure JPOXMLDOC01-appb-C000165
（式（１１）で表される化合物（化合物Ａ））
　化合物Ａは、下記式（１１－１）及び（１１－３）で表される化合物、又は下記式（１１－２）及び（１１－３）で表される化合物である。化合物Ａは、有機層に含まれる。好ましくは発光層に含まれる。
Figure JPOXMLDOC01-appb-C000166
 (Compound represented by Formula (11) (Compound A))
The compound A is a compound represented by the following formulas (11-1) and (11-3), or a compound represented by the following formulas (11-2) and (11-3). Compound A is contained in the organic layer. It is preferably contained in the light emitting layer.
Figure JPOXMLDOC01-appb-C000166
　式（１１－１）、式（１１－２）及び式（１１－３）中、
　環Ａは、置換もしくは無置換の環形成炭素数１０～５０の縮合アリール環、置換もしくは無置換の環形成原子数８～５０の縮合複素環、又は下記式（Ｘ）で表されるベンゼン環である。）
Figure JPOXMLDOC01-appb-C000167
 （式（Ｘ）中、
　２つの＊で示す環形成炭素原子の一方で、前記式（１１－１）又は前記式（１１－２）のベンゼン環Ｂから延びる＊と結合し、他方で前記式（１１－３）のベンゼン環Ｃから延びる単結合と結合する。
　前記式（１１－１）の２つの＊は、それぞれ、前記環Ａの前記縮合アリール環の環形成炭素原子、前記縮合複素環の環形成原子、又は前記式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合する。
　前記式（１１－２）の３つの＊は、それぞれ、前記環Ａの前記縮合アリール環の環形成炭素原子、前記縮合複素環の環形成原子、又は前記式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合する。）
　Ｒ１０１～Ｒ１１６のうち隣接する２つ以上の１組以上は、置換もしくは無置換の飽和又は不飽和の環を形成するか、あるいは前記環を形成しない。
　前記環を形成しないＲ１０１～Ｒ１１６、及びＲ１１７は、それぞれ独立に、
水素原子、ハロゲン原子、シアノ基、ニトロ基、ハロアルキル基、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
－Ｃ（＝Ｏ）（Ｒ９０８）、
－ＣＯＯ（Ｒ９０９）、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０９は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０９が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０９のそれぞれは同一でもよく、異なっていてもよい。
　ｎは１又は２の整数である。ｎが２である場合、２つのＲ１１７は同じであってもよく、また、異なってもよい。 In formula (11-1), formula (11-2) and formula (11-3),
Ring A is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms, or a benzene ring represented by the following formula (X). Is. )
Figure JPOXMLDOC01-appb-C000167
 (In formula (X),
One of the two ring-forming carbon atoms represented by * is bonded to * extending from the benzene ring B of the formula (11-1) or (11-2), and the other benzene of the formula (11-3). Bond with a single bond extending from ring C.
The two * in the formula (11-1) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
The three *'s in the formula (11-2) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of. )
One or more adjacent two or more sets of R 101 to R 116 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
R 101 to R 116 and R 117 that do not form a ring are each independently
Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
-C(=O)(R 908 ),
-COO (R 909 ),
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 909 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two or more R 901 to R 909 are present, each of the two or more R 901 to R 909 may be the same or different.
n is an integer of 1 or 2. When n is 2, the two R 117 may be the same or different.
　式（１１－１）、式（１１－２）及び式（１１－３）において、縮合アリール環とは、複数の芳香族環が縮合した環である。従って、例えば、２つの芳香族環が単結合で結合したビフェニルは縮合アリール環に含まれない。
　式（１１－１）、式（１１－２）及び式（１１－３）において、縮合複素環とは、複数の複素環が縮合した環、又は複素環と芳香族環が縮合した環である。 In Formula (11-1), Formula (11-2) and Formula (11-3), the fused aryl ring is a ring in which a plurality of aromatic rings are fused. Thus, for example, biphenyl in which two aromatic rings are linked by a single bond is not included in the fused aryl ring.
In Formula (11-1), Formula (11-2) and Formula (11-3), the condensed heterocycle is a ring in which a plurality of heterocycles are condensed or a ring in which a heterocycle and an aromatic ring are condensed. ..
　環Ａの「縮合アリール環」は、上述した「アリール基」に水素原子を導入した化合物と同じ構造である。具体例としては、具体例群Ｇ１に記載の「アリール基」に水素原子を導入した化合物等が挙げられる。
　環Ａの「縮合複素環」は、上述した「複素環基」のうち、縮合環構造を有するものに水素原子を導入した化合物と同じ構造である。具体例としては、具体例群Ｇ２に記載の「複素環基」のうち縮合環構造を有するものに水素原子を導入した化合物等が挙げられる。 The “fused aryl ring” of ring A has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned “aryl group”. Specific examples include compounds in which a hydrogen atom is introduced into the "aryl group" described in Specific Example Group G1.
The “fused heterocycle” of ring A has the same structure as the above-mentioned “heterocyclic group” having a condensed ring structure and a hydrogen atom introduced therein. Specific examples thereof include compounds in which a hydrogen atom has been introduced into those having a condensed ring structure among the “heterocyclic groups” described in Specific Example Group G2.
　式（１１－１）中の「＊」（アスタリスク）は、式（１１－３）の環Ａと結合する。式（１１－１）には、２つの「＊」があるが、２つの「＊」は、それぞれ、環Ａの縮合アリール環の環形成炭素原子、縮合複素環の環形成原子、又は式（２）で表されるベンゼン環の環形成炭素原子と結合して、化合物を構成する。
　式（１１－２）中の「＊」（アスタリスク）も、式（１１－３）の環Ａと結合する。式（１１－２）には、３つの「＊」があるが、３つの「＊」は、それぞれ、環Ａの縮合アリール環の環形成炭素原子、縮合複素環の環形成原子、又は式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合して、化合物を構成する。
　式（Ｘ）中の「＊」（アスタリスク）は、結合位置を示す。２つの＊の環形成炭素原子の一方で、式（１１－１）又は式（１１－２）のベンゼン環Ｂから延びる＊が結合し、他方で式（１１－３）のベンゼン環Ｃから延びる単結合と結合する。 "*" (asterisk) in the formula (11-1) is bonded to the ring A in the formula (11-3). In formula (11-1), there are two “*”, and each of the two “*” is a ring-forming carbon atom of the condensed aryl ring of ring A, a ring-forming atom of the condensed heterocycle, or the formula ( The compound is bonded to the ring-forming carbon atom of the benzene ring represented by 2).
The “*” (asterisk) in formula (11-2) is also bonded to ring A in formula (11-3). In formula (11-2), there are three “*”, and each of the three “*” is a ring-forming carbon atom of the condensed aryl ring of ring A, a ring-forming atom of the condensed heterocycle, or the formula ( The compound is bonded to the ring-forming carbon atom of the benzene ring represented by X).
"*" (asterisk) in the formula (X) indicates a bonding position. On one of the two * ring-forming carbon atoms, * extending from the benzene ring B of the formula (11-1) or (11-2) is bonded, and on the other side, extending from the benzene ring C of the formula (11-3). Combine with a single bond.
　定義に記載していない基について、ハロアルキル基は、具体例群Ｇ３に記載の「アルキル基」の１つ以上の水素がハロゲン原子で置換された基である。
　－Ｃ（＝Ｏ）（Ｒ９０８）で表される基の具体例としては、
－Ｃ（＝Ｏ）（Ｇ１）
－Ｃ（＝Ｏ）（Ｇ２）
－Ｃ（＝Ｏ）（Ｇ３）
－Ｃ（＝Ｏ）（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は具体例群Ｇ１に記載の「アリール基」である。
　Ｇ２は具体例群Ｇ２に記載の「複素環基」である。
　Ｇ３は具体例群Ｇ３に記載の「アルキル基」である。
　Ｇ６は具体例群Ｇ６に記載の「シクロアルキル基」である。 For groups not mentioned in the definitions, a haloalkyl group is a group in which one or more hydrogens of the “alkyl group” described in specific example group G3 are substituted with a halogen atom.
Specific examples of the group represented by —C(═O)(R 908 ) include the following:
-C(=O)(G1)
-C(=O)(G2)
-C(=O)(G3)
-C(=O)(G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is a "heterocyclic group" described in Specific Example Group G2.
G3 is an "alkyl group" described in Specific Example Group G3.
G6 is a "cycloalkyl group" described in Specific Example Group G6.
　－ＣＯＯ（Ｒ９０９）で表される基の具体例としては、
－ＣＯＯ（Ｇ１）
－ＣＯＯ（Ｇ２）
－ＣＯＯ（Ｇ３）
－ＣＯＯ（Ｇ６）
が挙げられる。
　ここで、Ｇ１、Ｇ２、Ｇ３及びＧ６は、上記－Ｃ（＝Ｏ）（Ｒ９０８）の例と同様である。 Specific examples of the group represented by —COO(R 909 ) include:
-COO (G1)
-COO (G2)
-COO (G3)
-COO (G6)
Is mentioned.
Here, G1, G2, G3, and G6 are the same as in the example of -C(=O)(R 908 ).
　一実施形態においては、式（１１－１）及び（１１－３）で表される化合物、又は式（１１－２）及び（１１－３）で表される化合物は、下記式（１３）、式（１４）又は式（１５）で表される化合物である。
Figure JPOXMLDOC01-appb-C000168
 In one embodiment, the compounds represented by the formulas (11-1) and (11-3) or the compounds represented by the formulas (11-2) and (11-3) are represented by the following formula (13), It is a compound represented by formula (14) or formula (15).
Figure JPOXMLDOC01-appb-C000168
（前記式（１３）、前記式（１４）及び前記式（１５）中、
　環Ａ’は、置換もしくは無置換の環形成炭素数１０～５０の縮合アリール環、又は置換もしくは無置換の環形成原子数８～５０の縮合複素環である。
　Ｒ１０１～Ｒ１０７及びＲ１１０～Ｒ１１７は、前記式（１１－１）、前記式（１１－２）、前記式（１１－３）及び前記式（Ｘ）で定義したとおりである。） (In the formula (13), the formula (14) and the formula (15),
Ring A′ is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms.
R 101 to R 107 and R 110 to R 117 are as defined in the formula (11-1), the formula (11-2), the formula (11-3) and the formula (X). )
　一実施形態においては、式（１１－３）の環Ａ及び式（１５）の環Ａ’の置換もしくは無置換の環形成炭素数１０～５０の縮合アリール環は、置換もしくは無置換のナフタレン環、又は置換もしくは無置換のフルオレン環である。 In one embodiment, the substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms of the ring A of the formula (11-3) and the ring A′ of the formula (15) is a substituted or unsubstituted naphthalene ring. Or a substituted or unsubstituted fluorene ring.
　一実施形態においては、式（１１－３）の環Ａ及び式（１５）の環Ａ’の置換もしくは無置換の環形成原子数８～５０の縮合複素環は、置換もしくは無置換のジベンゾフラン環、置換もしくは無置換のカルバゾール環、又は置換もしくは無置換のジベンゾチオフェン環である。 In one embodiment, the substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms of the ring A of the formula (11-3) and the ring A′ of the formula (15) is a substituted or unsubstituted dibenzofuran ring. , A substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
　一実施形態においては、式（１１－１）及び（１１－３）で表される化合物、又は式（１１－２）及び（１１－３）で表される化合物は、下記式（１６－１）～式（１６－５）で表される化合物からなる群から選択される。
Figure JPOXMLDOC01-appb-C000169
 In one embodiment, the compounds represented by the formulas (11-1) and (11-3) or the compounds represented by the formulas (11-2) and (11-3) have the following formula (16-1): ) To a compound represented by the formula (16-5).
Figure JPOXMLDOC01-appb-C000169
（前記式（１６－１）～（１６－５）中、
　Ｒ１０１～Ｒ１１７は、前記式（１１－１）、前記式（１１－２）、前記式（１１－３）及び前記式（Ｘ）で定義したとおりである。
　Ｘは、Ｏ、ＮＲ１２５、又はＣ（Ｒ１２６）（Ｒ１２７）である。
　Ｒ１２１～Ｒ１２７のうち隣接する２つ以上の１組以上は、置換もしくは無置換の飽和又は不飽和の環を形成するか、あるいは前記環を形成しない。
　前記環を形成しないＲ１２１～Ｒ１２７は、それぞれ独立に、
水素原子、ハロゲン原子、シアノ基、ニトロ基、ハロアルキル基、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の炭素数７～５０のアラルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
－Ｃ（＝Ｏ）（Ｒ９０８）、
－ＣＯＯ（Ｒ９０９）、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０９は、前記式前記式（１１－１）～（１１－３）で定義したとおりである。） (In the above formulas (16-1) to (16-5),
R 101 to R 117 are as defined in the formula (11-1), the formula (11-2), the formula (11-3) and the formula (X).
X is O, NR 125 , or C(R 126 )(R 127 ).
One or more adjacent two or more sets of R 121 to R 127 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
R 121 to R 127 which do not form a ring are each independently
Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
-C(=O)(R 908 ),
-COO (R 909 ),
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 909 are as defined in the above formulas (11-1) to (11-3). )
　一実施形態においては、前記化合物Ａが、前記式（１３）で表される化合物である。また、式（１３）のＲ１０５及びＲ１１４はそれぞれ独立に、－Ｎ（Ｒ９０６）（Ｒ９０７）（Ｒ９０１～Ｒ９０７は、前記式（１）で定義したとおりである。）である。 In one embodiment, the compound A is a compound represented by the formula (13). Further, R 105 and R 114 in the formula (13) are each independently —N(R 906 )(R 907 )(R 901 to R 907 are as defined in the above formula (1)). ..
　一実施形態においては、前記有機層が、発光層を含み、
　前記発光層が、前記式（１）で表される化合物、及び化合物Ａを含む。このとき、前記式（１）で表される化合物は、発光層のホスト材料として機能し、化合物Ａは、発光層のドーパント材料として機能する。 In one embodiment, the organic layer comprises a light emitting layer,
The light emitting layer contains the compound represented by the formula (1) and the compound A. At this time, the compound represented by the formula (1) functions as a host material of the light emitting layer, and the compound A functions as a dopant material of the light emitting layer.
　式（１１）で表される化合物（化合物Ａ）の具体例としては、例えば、以下に示す化合物が挙げられる。下記具体例中、Ｍｅはメチル基を示す。
Figure JPOXMLDOC01-appb-C000170
Figure JPOXMLDOC01-appb-C000171
Figure JPOXMLDOC01-appb-C000172
Figure JPOXMLDOC01-appb-C000173
Figure JPOXMLDOC01-appb-C000174
Figure JPOXMLDOC01-appb-C000175
Figure JPOXMLDOC01-appb-C000176
Figure JPOXMLDOC01-appb-C000177
Figure JPOXMLDOC01-appb-C000178
Figure JPOXMLDOC01-appb-C000179
Figure JPOXMLDOC01-appb-C000180
Figure JPOXMLDOC01-appb-C000181
 Specific examples of the compound represented by Formula (11) (Compound A) include the compounds shown below. In the following specific examples, Me represents a methyl group.
Figure JPOXMLDOC01-appb-C000170
Figure JPOXMLDOC01-appb-C000171
Figure JPOXMLDOC01-appb-C000172
Figure JPOXMLDOC01-appb-C000173
Figure JPOXMLDOC01-appb-C000174
Figure JPOXMLDOC01-appb-C000175
Figure JPOXMLDOC01-appb-C000176
Figure JPOXMLDOC01-appb-C000177
Figure JPOXMLDOC01-appb-C000178
Figure JPOXMLDOC01-appb-C000179
Figure JPOXMLDOC01-appb-C000180
Figure JPOXMLDOC01-appb-C000181
Figure JPOXMLDOC01-appb-C000182
Figure JPOXMLDOC01-appb-C000182
　化合物Ａは、例えば、後述する実施例の反応に倣い、目的物に合わせた既知の代替反応や原料を用いて合成することができる。 Compound A can be synthesized, for example, by following known reactions in Examples described later and using known alternative reactions or starting materials according to the intended product.
（式（２０）で表される化合物）
　一実施形態においては、有機層が、さらに、発光層に隣接する正孔阻止層を含み、正孔阻止層が、式（２０）、（２１）及び（３１）で表される化合物から選択される１以上の化合物を含む。
　ここで、「正孔阻止層」とは、発光層から電子輸送層へ正孔が漏れることを防ぐという機能を目的として、発光層と電子輸送層との間に設けられる層であり、陰極から注入された電子を発光層へ輸送する電子輸送層としての機能も有する層である。
Figure JPOXMLDOC01-appb-C000183
 (Compound represented by Formula (20))
In one embodiment, the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, the hole blocking layer selected from compounds represented by formulas (20), (21) and (31). Or more than one compound.
Here, the “hole blocking layer” is a layer provided between the light emitting layer and the electron transporting layer for the purpose of preventing holes from leaking from the light emitting layer to the electron transporting layer. The layer also has a function as an electron transport layer that transports injected electrons to the light emitting layer.
Figure JPOXMLDOC01-appb-C000183
［式（２０）中、Ｘ２１は酸素原子、硫黄原子又はセレン原子を表す。
　Ｌ２１は、置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　Ａｒ２１、Ａｒ２２及びＡｒ２３は、それぞれ独立に、置換もしくは無置換の環形成炭素数６～５０のアリール基、又は置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ａｒ２１とＡｒ２２は結合して環を形成していてもよい。
　ｎ２１は、１～３の整数である。］ [In the formula (20), X 21 represents an oxygen atom, a sulfur atom or a selenium atom.
L 21 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
Ar 21 , Ar 22 and Ar 23 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. Is. Ar 21 and Ar 22 may combine with each other to form a ring.
n21 is an integer of 1 to 3. ]
　Ａｒ２１とＡｒ２２は結合して環を形成する場合、式（２０）で表される構造としては例えば下記構造が挙げられる。
Figure JPOXMLDOC01-appb-C000184
 When Ar 21 and Ar 22 are combined to form a ring, examples of the structure represented by the formula (20) include the following structures.
Figure JPOXMLDOC01-appb-C000184
　一実施形態において、式（２０）で表される化合物は、下記式（２０－１）で表される化合物である。
Figure JPOXMLDOC01-appb-C000185
 In one embodiment, the compound represented by formula (20) is a compound represented by formula (20-1) below.
Figure JPOXMLDOC01-appb-C000185
　式（２０－１）において、Ｌ２１、Ｘ２１、Ａｒ２１、Ａｒ２２及びＡｒ２３は、前記式（２０）で定義したとおりである。 In the formula (20-1), L 21 , X 21 , Ar 21 , Ar 22 and Ar 23 are as defined in the formula (20).
　式（２０）で表される化合物の具体例としては、例えば、以下に示す化合物が挙げられる。
Figure JPOXMLDOC01-appb-C000186
 Specific examples of the compound represented by the formula (20) include the compounds shown below.
Figure JPOXMLDOC01-appb-C000186
（式（２１）で表される化合物）
　一実施形態においては、有機層が、さらに、発光層に隣接する正孔阻止層を含み、正孔阻止層が、式（２０）、（２１）及び（３１）で表される化合物から選択される１以上の化合物を含む。
Figure JPOXMLDOC01-appb-C000187
 (Compound represented by Formula (21))
In one embodiment, the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, the hole blocking layer selected from compounds represented by formulas (20), (21) and (31). Or more than one compound.
Figure JPOXMLDOC01-appb-C000187
［式（２１）中、
　Ｘ１～Ｘ３は、それぞれ独立に、Ｎ又はＣＲｂである。但し、Ｘ１～Ｘ３のうちの１個以上はＮである。
　Ｒｂは、
水素原子、
ハロゲン原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒｂが２個存在する場合、２個のＲｂは、互いに同一であってもよいし、異なっていてもよい。Ｒｂは、隣接するＲ２１～Ｒ２３と結合して環を形成しない。
　Ｒ２１～Ｒ２３は、それぞれ独立に、
－（Ｌ２）ｍ－（Ａｒ２）ｎ、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
　Ｌ２は、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　ｍは、０～２の整数である。ｍが０のとき、Ｌ２は単結合である。ｍが２のとき、２個のＬ２は互いに同一であってもよいし、異なっていてもよい。
　Ａｒ２は、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　ｎは、１又は２の整数であり、ｎが２のとき、２個のＡｒ２は、互いに同一であってもよいし、異なっていてもよい。但し、ｎが２のとき、ｍは１以上である。］ [In Formula (21),
X 1 to X 3 are each independently N or CR b . However, at least one of X 1 to X 3 is N.
R b is
Hydrogen atom,
Halogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
When two R b 's are present, the two R b 's may be the same or different from each other. R b does not form a ring by combining with R 21 to R 23 which are adjacent to each other.
R 21 to R 23 are each independently
-(L 2 ) m -(Ar 2 ) n ,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
L 2 is
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
m is an integer of 0 to 2. When m is 0, L 2 is a single bond. When m is 2, two L 2's may be the same or different.
Ar 2 is
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
n is an integer of 1 or 2, and when n is 2, two Ar 2 may be the same or different from each other. However, when n is 2, m is 1 or more. ]
　一実施形態においては、前記式（２１）におけるＸ１～Ｘ３のうちの２個が、Ｎである。即ち、中心骨格はピリミジン環となる。 In one embodiment, two of X 1 to X 3 in the above formula (21) are N. That is, the central skeleton is a pyrimidine ring.
　一実施形態においては、前記式（２１）におけるＲ２１～Ｒ２３が、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基である。 In one embodiment, R 21 to R 23 in the formula (21) are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
　一実施形態においては、前記式（２１）で表される化合物が、下記式（２１－１）で表される化合物である。 In one embodiment, the compound represented by the above formula (21) is a compound represented by the following formula (21-1).
Figure JPOXMLDOC01-appb-C000188
Figure JPOXMLDOC01-appb-C000188
［式（２１－１）中、Ｒ２１、Ｒ２２及びＸ３は、前記式（２１）で定義したとおりである。
　隣接するＲ５１～Ｒ５５の２個以上の１組以上が互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
　前記環を形成しないＲ５１～Ｒ５５は、それぞれ独立に、
水素原子、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、又は
無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］ [In the formula (21-1), R 21 , R 22 and X 3 are as defined in the formula (21).
Two or more adjacent groups of R 51 to R 55 are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or Do not form.
R 51 to R 55 which do not form a ring are each independently
Hydrogen atom,
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
　一実施形態においては、前記式（２１－１）で表される化合物が、下記式（２１－２）で表される化合物である。 In one embodiment, the compound represented by the formula (21-1) is a compound represented by the following formula (21-2).
Figure JPOXMLDOC01-appb-C000189
Figure JPOXMLDOC01-appb-C000189
［式（２１－２）中、Ｒ２２、Ｘ３及びＲ５１～Ｒ５５は、前記式（２１－１）で定義したとおりである。
　Ｒ５６～Ｒ６０は、それぞれ独立に、
水素原子、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、又は
無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］ [In the formula (21-2), R 22 , X 3 and R 51 to R 55 are as defined in the above formula (21-1).
R 56 to R 60 are each independently
Hydrogen atom,
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
　一実施形態においては、前記式（２１－２）で表される化合物が、下記式（２１－３）で表される化合物である。 In one embodiment, the compound represented by the formula (21-2) is a compound represented by the following formula (21-3).
Figure JPOXMLDOC01-appb-C000190
Figure JPOXMLDOC01-appb-C000190
［式（２１－３）中、Ｒ２２、Ｘ３及びＲ５６～Ｒ６０は、前記式（２１－２）で定義したとおりである。
　Ｙ１ａ～Ｙ８ａは、それぞれ独立に、ＣＲ６１ａ又はＮである。
　Ｙ１ｂ～Ｙ８ｂは、それぞれ独立に、ＣＲ６１ｂ又はＮである。
　Ｘ４ａは、Ｏ、Ｓ又はＮＲ６１ａである。
　Ｘ４ｂは、Ｏ、Ｓ又はＮＲ６１ｂである。
　隣接する原子に置換するＲ６１ａの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
　隣接する原子に置換するＲ６１ｂの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
　但し、Ｒ６１ａの１つが＊１と結合する単結合であるか、又は前記隣接する原子に置換するＲ６１ａの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介して＊１と結合する。
　Ｒ６１ｂの１つが＊２と結合する単結合であるか、又は前記隣接する原子に置換するＲ６１ｂの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介して＊２と結合する。
　前記環を形成せず、かつ、＊１又は＊２と結合する単結合ではないＲ６１ａ及びＲ６１ｂは、それぞれ独立に、
水素原子、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、又は
無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
　Ｒ６１ａが複数存在する場合、複数のＲ６１ａは、互いに同一であってもよいし、異なっていてもよい。
　Ｒ６１ｂが複数存在する場合、複数のＲ６１ｂは、互いに同一であってもよいし、異なっていてもよい。］ [In the formula (21-3), R 22 , X 3 and R 56 to R 60 are as defined in the formula (21-2).
Y 1a to Y 8a are each independently CR 61a or N.
Y 1b to Y 8b are each independently CR 61b or N.
X 4a is O, S or NR 61a .
X 4b is O, S or NR 61b .
Two or more sets of two or more R 61a substituting adjacent atoms are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring-forming atoms, or Does not form a ring.
Two or more sets of two or more R 61b substituting adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or Does not form a ring.
However, one of R 61a is a single bond which is bonded to *1, or two or more one or more groups of R 61a substituting the adjacent atoms are bonded to each other to form a ring-forming atom. One binds to *1 via a single bond.
One of R 61b is a single bond that is bonded to *2, or one of the atoms constituting the ring formed by two or more sets of two or more R 61b substituting the adjacent atoms is bonded to each other; , And to *2 via a single bond.
R 61a and R 61b which do not form the ring and which are not a single bond that binds to *1 or *2 are each independently,
Hydrogen atom,
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
If R 61a there are a plurality, a plurality of R 61a may be the same or may be different from one another.
If R 61b there are a plurality, the plurality of R 61b may be the same or may be different from one another. ]
　ここで、「Ｒ６１ａの１つがベンゼン環と結合する単結合であるか、Ｒ６１ｃが＊１と結合する単結合である」場合のＸ４ａ及びＹ１ａ～Ｙ８ａで構成される基の具体例としては、例えば、下記のものが挙げられる。 Here, a specific example of the group composed of X 4a and Y 1a to Y 8a in the case where “one of R 61a is a single bond that bonds to a benzene ring or R 61c is a single bond that bonds to *1” Examples include, for example:
Figure JPOXMLDOC01-appb-C000191
Figure JPOXMLDOC01-appb-C000191
　また、「前記隣接する原子に置換するＲ６１ａの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介してベンゼン環の炭素原子と結合する」場合のＸ４ａ及びＹ１ａ～Ｙ８ａで構成される基の具体例としては、例えば、下記のものが挙げられる。 In addition, “one of the atoms constituting the ring formed by bonding two or more sets of two or more R 61a substituting to the adjacent atoms to each other is bonded to a carbon atom of a benzene ring through a single bond. In this case, specific examples of the group composed of X 4a and Y 1a to Y 8a include the followings.
Figure JPOXMLDOC01-appb-C000192
Figure JPOXMLDOC01-appb-C000192
　一実施形態においては、前記式（２１）で表される化合物が、下記式（２１－４）で表される化合物である。 In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (21-4).
Figure JPOXMLDOC01-appb-C000193
Figure JPOXMLDOC01-appb-C000193
［式（２１－４）中、Ｘ１～Ｘ３、Ｒ２１、Ｒ２２、Ｌ２、ｍ及びｎは、前記式（２１）で定義したとおりである。
　Ｙ１～Ｙ８は、それぞれ独立に、ＣＲ６１ｅ又はＮである。
　Ｘ４は、Ｏ、Ｓ又はＮＲ６１ｅである。
　Ｒ６１ｅは、それぞれ独立に、
水素原子、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、又は
無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
　Ｒ６１ｅが複数存在する場合、複数のＲ６１ｅは、互いに同一であってもよいし、異なっていてもよい。
　隣接する原子に置換するＲ６１ｅの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは環を形成しない。
　但し、Ｒ６１ｅの１つが＊３と結合する単結合であるか、又は前記隣接する原子に置換するＲ６１ｅの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介して＊３と結合する。］ [In the formula (21-4), X 1 to X 3 , R 21 , R 22 , L 2 , m and n are as defined in the formula (21).
Y 1 to Y 8 are each independently CR 61e or N.
X 4 is O, S or NR 61e .
R 61e is each independently
Hydrogen atom,
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
If R 61e there are a plurality, the plurality of R 61e may be the same or may be different from one another.
Two or more sets of two or more R 61e substituting adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or a ring. Does not form.
However, one of R 61e is a single bond that is bonded to *3, or one or more groups of two or more of R 61e substituting the adjacent atoms are bonded to each other to form a ring. One binds to *3 via a single bond. ]
　以下に、式（２１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（２１）で表される化合物は下記具体例に限定されるものではない。 Specific examples of the compound represented by the formula (21) are described below, but these are merely examples, and the compound represented by the formula (21) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000194
Figure JPOXMLDOC01-appb-C000194
（式（３１）で表される化合物）
　一実施形態においては、有機層が、さらに、発光層に隣接する正孔阻止層を含み、正孔阻止層が、式（２０）、（２１）及び（３１）で表される化合物から選択される１以上の化合物を含む。 (Compound represented by Formula (31))
In one embodiment, the organic layer further comprises a hole blocking layer adjacent to the light emitting layer, the hole blocking layer selected from compounds represented by formulas (20), (21) and (31). Or more than one compound.
Figure JPOXMLDOC01-appb-C000195
Figure JPOXMLDOC01-appb-C000195
［式（３１）中、
　Ｒ３１～Ｒ４０のうちの１個以上は、－（Ｌ３）ｐ－Ａｒ３である。－（Ｌ３）ｐ－Ａｒ３が２個以上存在する場合、２個以上の－（Ｌ３）ｐ－Ａｒ３は互いに同一であってもよいし、異なっていてもよい。
　Ｌ３は、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　ｐは０～３の整数である。ｐが０のとき、Ｌ３は単結合である。ｐが２以上のとき、複数のＬ３は、互いに同一であってもよいし、異なっていてもよい。
　Ａｒ３は、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　－（Ｌ３）ｐ－Ａｒ３ではないＲ３１～Ｒ３６、及び－（Ｌ３）ｐ－Ａｒ３ではないＲ３７～Ｒ４０のうちの互いに隣接する２個以上の１組以上は、互いに結合して置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは環を形成しない。
　該環形成に関与しないＲ３１～Ｒ４０は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］ [In formula (31),
At least one of R 31 to R 40 is —(L 3 ) p —Ar 3 . When two or more -(L 3 ) p -Ar 3 are present, the two or more -(L 3 ) p -Ar 3 may be the same or different from each other.
L 3 is
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
p is an integer of 0 to 3. When p is 0, L 3 is a single bond. When p is 2 or more, the plurality of L 3 may be the same as or different from each other.
Ar 3 is
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
- (L 3) p R 31 ~ R 36 is not a -Ar 3, and - (L 3) p -Ar 3 1 or more sets of two or more adjacent to each other of R 37 ~ R 40 are not in each other They combine to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or no ring.
R 31 to R 40 not involved in the ring formation are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
　一実施形態においては、前記式（３１）におけるｐは０又は１であることが好ましい。 In one embodiment, p in the above formula (31) is preferably 0 or 1.
　一実施形態においては、前記式（３１）で表される化合物が、下記式（３１－１）で表される化合物である。 In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (31-1).
Figure JPOXMLDOC01-appb-C000196
Figure JPOXMLDOC01-appb-C000196
［式（３１－１）中、Ｌ３、ｐ、Ａｒ３、Ｒ３１、Ｒ３２、及びＲ３４～Ｒ４０は、前記式（３１）で定義したとおりである。］ [In the formula (31-1), L 3 , p, Ar 3 , R 31 , R 32 , and R 34 to R 40 are as defined in the formula (31). ]
　一実施形態においては、前記式（３１）で表される化合物が、下記式（３１－１Ｈ）で表される化合物である。 In one embodiment, the compound represented by the above formula (31) is a compound represented by the following formula (31-1H).
Figure JPOXMLDOC01-appb-C000197
Figure JPOXMLDOC01-appb-C000197
［式（３１－１Ｈ）中、Ｌ３、ｐ及びＡｒ３は、前記式（３１）で定義したとおりである。］ [In the formula (31-1H), L 3 , p and Ar 3 are as defined in the formula (31). ]
　以下に、式（３１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（３１）で表される化合物は下記具体例に限定されるものではない。 Specific examples of the compound represented by the formula (31) will be described below, but these are merely examples, and the compound represented by the formula (31) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000198
Figure JPOXMLDOC01-appb-C000198
（式（４１）で表される化合物）
　一実施形態においては、有機層が、さらに発光層に隣接する電子阻止層を含み、電子阻止層が、下記式（４１）で表される化合物で表される化合物を含む。
　ここで、「電子阻止層」とは、発光層から正孔輸送層へ電子が漏れることを防ぐという機能を目的として、発光層と正孔輸送層との間に設けられる層であり、陽極から注入された正孔を発光層へ輸送する正孔輸送層としての機能も有する層である。 (Compound represented by Formula (41))
In one embodiment, the organic layer further includes an electron blocking layer adjacent to the light emitting layer, and the electron blocking layer contains a compound represented by the following formula (41).
Here, the “electron blocking layer” is a layer provided between the light emitting layer and the hole transporting layer for the purpose of preventing electrons from leaking from the light emitting layer to the hole transporting layer. The layer also has a function as a hole transport layer that transports the injected holes to the light emitting layer.
Figure JPOXMLDOC01-appb-C000199
Figure JPOXMLDOC01-appb-C000199
［式（４１）中、
　Ｌ４１～Ｌ４３は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　Ａｒ４１～Ａｒ４３は、それぞれ独立に、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。］ [In Formula (41),
L 41 to L 43 are each independently
Single bond,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
Ar 41 to Ar 43 are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. ]
　一実施形態においては、前記式（４１）で表される化合物が、下記式（４１－１）で表される化合物である。 In one embodiment, the compound represented by the formula (41) is a compound represented by the following formula (41-1).
Figure JPOXMLDOC01-appb-C000200
Figure JPOXMLDOC01-appb-C000200
［式（４１－１）中、Ａｒ４１～Ａｒ４３及びＬ４１は、前記式（４１）で定義したとおりである。］
　Ａｒ４２及びＡｒ４３は、それぞれが置換するフェニル基を構成するいずれかの炭素原子と結合する。 [In the formula (41-1), Ar 41 to Ar 43 and L 41 are as defined in the formula (41). ]
Ar 42 and Ar 43 are bonded to any carbon atom constituting the phenyl group which they respectively substitute.
　一実施形態においては、前記式（４１）で表される化合物が、下記式（４１－２）で表される化合物である。 In one embodiment, the compound represented by the above formula (41) is a compound represented by the following formula (41-2).
Figure JPOXMLDOC01-appb-C000201
Figure JPOXMLDOC01-appb-C000201
［式（４１－２）中、Ａｒ４１及びＬ４１は、前記式（４１）で定義したとおりである。
　Ｘ５及びＸ６は、それぞれ独立に、Ｏ、Ｓ又はＮ（Ｒ９０６）である。
　Ｒ９０６は、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０６が２個存在する場合、２個のＲ９０６はそれぞれは同一でもよく、異なっていてもよい。］
　Ｘ５又はＸ６を含む１価の複素環基の一方のベンゼン環を構成する炭素原子のいずれかと、中心の窒素原子に置換しているフェニル基を構成する炭素原子のいずれかとが結合する。 [In the formula (41-2), Ar 41 and L 41 are as defined in the above formula (41).
X 5 and X 6 are each independently O, S or N(R 906 ).
R 906 is
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two R 906 are present, the two R 906 may be the same or different. ]
One of the carbon atoms constituting the benzene ring of one of the monovalent heterocyclic groups containing X 5 or X 6 is bonded to any of the carbon atoms constituting the phenyl group substituted on the central nitrogen atom.
　一実施形態においては、前記式（４１）で表される化合物が、下記式（４１－３）で表される化合物である。 In one embodiment, the compound represented by the formula (41) is a compound represented by the following formula (41-3).
Figure JPOXMLDOC01-appb-C000202
Figure JPOXMLDOC01-appb-C000202
［式（４１－３）中、Ａｒ４１、Ａｒ４２及びＬ４１～Ｌ４３は、前記式（４１）で定義したとおりである。
　Ｘ７は、Ｏ、Ｓ又はＮＲ８９である。
　隣接する原子に置換するＲ８１～Ｒ８９のうちの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
　但し、Ｒ８１～Ｒ８９の１つが＊６と結合する単結合であるか、又は前記隣接する原子に置換するＲ８１～Ｒ８９のうちの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、＊６と単結合を介して結合する。
　前記環を形成せず、かつ、＊６と結合する単結合ではないＲ８１～Ｒ８９は、それぞれ独立に、
水素原子、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、又は
無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］ [In the formula (41-3), Ar 41 , Ar 42, and L 41 to L 43 are as defined in the formula (41).
X 7 is O, S or NR 89 .
Two or more sets of two or more of R 81 to R 89 which substitute the adjacent atom are bonded to each other to form a substituted or unsubstituted ring-forming saturated or unsaturated ring having 3 to 30 ring-forming atoms. Or does not form the ring.
Provided that one of R 81 to R 89 is a single bond that bonds to *6, or two or more sets of R 81 to R 89 which substitute the adjacent atoms are bonded to each other. One of the atoms constituting the ring formed is bonded to *6 via a single bond.
R 81 to R 89 , which do not form a ring and are not a single bond that binds to *6, are each independently
Hydrogen atom,
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
　以下に、式（４１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（４１）で表される化合物は下記具体例に限定されるものではない。 Specific examples of the compound represented by the formula (41) will be described below, but these are merely examples, and the compound represented by the formula (41) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000203
Figure JPOXMLDOC01-appb-C000203
Figure JPOXMLDOC01-appb-C000204
Figure JPOXMLDOC01-appb-C000204
（式（５１）で表される化合物）
　一実施形態においては、有機層が、さらに発光層に隣接する電子阻止層を含み、電子阻止層が、下記式（５１）で表される化合物で表される化合物を含む。
Figure JPOXMLDOC01-appb-C000205
 (Compound represented by Formula (51))
In one embodiment, the organic layer further includes an electron blocking layer adjacent to the light emitting layer, and the electron blocking layer contains a compound represented by the following formula (51).
Figure JPOXMLDOC01-appb-C000205
［式（５１）中、
　隣接する原子に置換するＲ６２～Ｒ７０の２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
　隣接する原子に置換するＲ７１～Ｒ７９の２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
　但し、Ｒ６２～Ｒ７０のうちの１つが＊４と結合する単結合であるか、又は前記隣接する原子に置換するＲ６２～Ｒ７０の２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、＊４と単結合を介して結合する。
　Ｒ７１～Ｒ７９のうちの１つが＊５と結合する単結合であるか、又は前記隣接する原子に置換するＲ７１～Ｒ７９の２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、＊５と単結合を介して結合する。また、＊５と結合しないＲ７１～Ｒ７９のうちの１つがＬ５２と結合する単結合であるか、又は前記隣接する原子に置換するＲ７１～Ｒ７９の２個以上の１組以上が互いに結合して形成された環を構成する原子のうちの他の１つが、Ｌ５２と単結合を介して結合する。
　前記環を形成せず、かつ、＊４又は＊５と結合する単結合ではないＲ６２～Ｒ７９は、それぞれ独立に、
水素原子、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、又は
無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
　Ｌ５１は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　ｑは、０～３の整数である。ｑが２以上のとき、２以上存在するＲ６２～Ｒ７０は互いに同一であってもよいし、異なっていてもよい。但し、ｑが０のときはＬ５１を終端する水素原子である。
　ｒは０～２の整数である。ｒが０のとき、Ｌ５１は単結合である。ｒが２のとき、２個のＬ５１は、互いに同一であってもよいし、異なっていてもよい。但し、ｑが２以上のとき、ｒは１又は２である。
　Ｌ５２は、
単結合、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　Ａｒ５２は、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。］ [In formula (51),
At least one pair of two or more of R 62 to R 70 substituting adjacent atoms is bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring-forming atoms; , Or does not form the ring.
Two or more sets of two or more of R 71 to R 79 which are substituted on adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms. , Or does not form the ring.
Provided that one of R 62 to R 70 is a single bond that bonds to *4, or two or more pairs of R 62 to R 70 which substitute the adjacent atom are bonded to each other. One of the atoms constituting the ring formed is bonded to *4 via a single bond.
One of R 71 to R 79 is a single bond that binds to *5, or two or more pairs of R 71 to R 79 which substitute the adjacent atom are formed by bonding to each other; One of the atoms constituting the ring is bonded to *5 via a single bond. In addition, one of R 71 to R 79 that does not bond to *5 is a single bond that bonds to L 52 , or one or more pairs of two or more of R 71 to R 79 that substitute for the adjacent atom are Another one of the atoms constituting the ring formed by bonding to each other is bonded to L 52 via a single bond.
R 62 to R 79 which do not form a ring and which are not a single bond to bond with *4 or *5 are each independently
Hydrogen atom,
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
L 51 is, independently of each other,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
q is an integer of 0 to 3. When q is 2 or more, R 62 to R 70 existing in two or more may be the same or different from each other. However, when q is 0, it is a hydrogen atom terminating L 51 .
r is an integer of 0 to 2. When r is 0, L 51 is a single bond. When r is 2, two L 51 's may be the same or different from each other. However, when q is 2 or more, r is 1 or 2.
L 52 is
Single bond,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
Ar 52 is
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. ]
　一実施形態においては、前記式（５１）で表される化合物が、下記式（５１－１）で表される化合物である。 In one embodiment, the compound represented by the formula (51) is a compound represented by the following formula (51-1).
Figure JPOXMLDOC01-appb-C000206
Figure JPOXMLDOC01-appb-C000206
［式（５１－１）中、Ｒ６２～Ｒ７０、Ｒ７２～Ｒ７９、＊４、＊５、ｑ、Ｌ５１、ｒ、Ｌ５２及びＡｒ５２は、前記式（５１）で定義したとおりである。］ [In the formula (51-1), R 62 to R 70 , R 72 to R 79 , *4, *5, q, L 51 , r, L 52, and Ar 52 are as defined in the formula (51). Is. ]
　一実施形態においては、前記式（５１）におけるｑが１である。 In one embodiment, q in the above formula (51) is 1.
　一実施形態においては、前記式（５１）で表される化合物が、下記式（５１－２）で表される化合物である。 In one embodiment, the compound represented by the above formula (51) is a compound represented by the following formula (51-2).
Figure JPOXMLDOC01-appb-C000207
Figure JPOXMLDOC01-appb-C000207
［式（５１－２）中、Ｒ６２、Ｌ５１、ｒ、Ｌ５２及びＡｒ５２は、前記式（５１）で定義したとおりである。］ [In the formula (51-2), R 62 , L 51 , r, L 52, and Ar 52 are as defined in the formula (51). ]
　一実施形態においては、前記式（５１）で表される化合物が、下記式（５１－３ａ）～（５１－３ｃ）で表される化合物からなる群から選択される。 In one embodiment, the compound represented by the above formula (51) is selected from the group consisting of compounds represented by the following formulas (51-3a) to (51-3c).
Figure JPOXMLDOC01-appb-C000208
Figure JPOXMLDOC01-appb-C000208
［式（５１－３ａ）～（５１－３ｃ）中、Ｒ６２、Ｌ５１、ｒ、Ｌ５２及びＡｒ５２は、前記式（５１）で定義したとおりである。］ [In the formulas (51-3a) to (51-3c), R 62 , L 51 , r, L 52, and Ar 52 are as defined in the formula (51). ]
　以下に、式（５１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（５１）で表される化合物は下記具体例に限定されるものではない。 Specific examples of the compound represented by the formula (51) will be described below, but these are merely examples, and the compound represented by the formula (51) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000209
Figure JPOXMLDOC01-appb-C000209
　一実施形態においては、前記式（１）、（１１）、（２０）、（２１）、（３１）、（４１）及び（５１）で表される化合物における、前記「置換もしくは無置換の」という場合の置換基が、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）
（ここで、
Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の１価の複素環基
からなる群から選択される基である。 In one embodiment, in the compounds represented by the formulas (1), (11), (20), (21), (31), (41) and (51), the "substituted or unsubstituted" In that case, the substituent is
An unsubstituted alkyl group having 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,
An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 )
(here,
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ),
Halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
　一実施形態においては、前記式（１）、（１１）、（２０）、（２１）、（３１）、（４１）及び（５１）で表される化合物における、前記「置換もしくは無置換の」という場合の置換基が、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の１価の複素環基
からなる群から選択される基である。 In one embodiment, in the compounds represented by the formulas (1), (11), (20), (21), (31), (41) and (51), the "substituted or unsubstituted" In that case, the substituent is
An alkyl group having 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
　一実施形態においては、前記式（１）、（１１）、（２０）、（２１）、（３１）、（４１）及び（５１）で表される化合物における、前記「置換もしくは無置換の」という場合の置換基が、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の１価の複素環基
からなる群から選択される基である。 In one embodiment, in the compounds represented by the formulas (1), (11), (20), (21), (31), (41) and (51), the "substituted or unsubstituted" In that case, the substituent is
An alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
　上記各基の具体例は、本明細書の［定義］の欄に記載のとおりである。 Specific examples of each of the above groups are as described in the [Definition] column of this specification.
　第１の態様の有機ＥＬ素子は、前述したように、陰極と、陽極と、前記陰極と前記陽極との間に有機層を有し、前記有機層が、前記式（１）で表される化合物と、前記式（１１）で表される化合物と、を含む以外は、本発明の効果を損なわない限りにおいて、従来公知の材料、素子構成を適用することができる。
　第２の態様の有機ＥＬ素子は、前述したように、陰極と、陽極と、前記陰極と前記陽極との間に有機層を有し、前記有機層が発光層を含み、前記発光層が前記式（１）で表される化合物と、前記式（１１）で表される化合物とを含み、前記発光層に隣接する正孔阻止層が前記式（２０）で表される化合物、前記式（２１）で表される化合物及び前記式（３１）で表される化合物の1以上を含む以外は、本発明の効果を損なわない限りにおいて、従来公知の材料、素子構成を適用することができる。
　第３の態様の有機ＥＬ素子は、前述したように、陰極と、陽極と、前記陰極と前記陽極との間に有機層を有し、前記有機層が発光層を含み、前記発光層が前記式（１）で表される化合物と、前記式（１１）で表される化合物とを含み、前記発光層に隣接する電子阻止層が前記式（４１）で表される化合物、又は下記式（５１）で表される化合物を含む以外は、本発明の効果を損なわない限りにおいて、従来公知の材料、素子構成を適用することができる。
　第４の態様の有機ＥＬ素子は、前述したように、陰極と、陽極と、前記陰極と前記陽極との間に有機層を有し、前記有機層が発光層を含み、前記発光層が前記式（１）で表される化合物と、前記式（１１）で表される化合物とを含み、前記発光層に隣接する正孔阻止層が前記式（２０）で表される化合物、前記式（２１）で表される化合物及び前記式（３１）で表される化合物の1以上を含み、前記発光層に隣接する電子阻止層が前記式（４１）で表される化合物、又は下記式（５１）で表される化合物を含む以外は、本発明の効果を損なわない限りにおいて、従来公知の材料、素子構成を適用することができる。 As described above, the organic EL element of the first aspect has a cathode, an anode, and an organic layer between the cathode and the anode, and the organic layer is represented by the formula (1). Other than including the compound and the compound represented by the formula (11), conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.
As described above, the organic EL device of the second aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer includes a light emitting layer, and the light emitting layer is the light emitting layer. A compound represented by the formula (1) and a compound represented by the formula (11), wherein the hole blocking layer adjacent to the light emitting layer is represented by the formula (20); Conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired, except that the compound represented by 21) and one or more compounds represented by the formula (31) are included.
As described above, the organic EL device of the third aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer includes a light emitting layer, and the light emitting layer is the A compound containing a compound represented by the formula (1) and a compound represented by the formula (11), wherein the electron blocking layer adjacent to the light emitting layer is represented by the formula (41), or a compound represented by the following formula (41) Other than the compound represented by 51), conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.
As described above, the organic EL element of the fourth aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer includes a light emitting layer, and the light emitting layer is the light emitting layer. A compound represented by the formula (1) and a compound represented by the formula (11), wherein the hole blocking layer adjacent to the light emitting layer is represented by the formula (20); 21) and one or more compounds represented by the formula (31), wherein the electron blocking layer adjacent to the light emitting layer is represented by the formula (41), or a compound represented by the following formula (51) Conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired, except that the compound represented by the formula (1) is included.
　第５の態様の有機ＥＬ素子は、前述したように、陰極と、陽極と、前記陰極と前記陽極との間に有機層を有し、前記有機層が２以上の発光層を含み、前記２以上の発光層のうちの１以上が前記式（１）で表される化合物と、前記式（１１）で表される化合物とを含む以外は、本発明の効果を損なわない限りにおいて、従来公知の材料、素子構成を適用することができる。
　以下、第１～第５の態様の有機ＥＬ素子の一実施形態で用いることができる部材、及び各層を構成する、前記式（１）、（１１）、（２０）、（２１）、（３１）、（４１）及び（５１）で表される化合物以外の材料等について説明する。 As described above, the organic EL element of the fifth aspect has a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including two or more light emitting layers, and As long as one or more of the above light emitting layers contains a compound represented by the formula (1) and a compound represented by the formula (11), it is a conventionally known substance unless the effects of the present invention are impaired. The materials and element configurations of can be applied.
Hereinafter, members that can be used in one embodiment of the organic EL device of the first to fifth aspects, and the above formulas (1), (11), (20), (21), and (31) that form each layer. ), (41) and (51) other than the compounds represented by the following.
（基板）
　基板は、発光素子の支持体として用いられる。基板としては、例えば、ガラス、石英、プラスチック等を用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる（フレキシブル）基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。 (substrate)
The substrate is used as a support for the light emitting device. As the substrate, for example, glass, quartz, plastic or the like can be used. Alternatively, a flexible substrate may be used. The flexible substrate is a flexible (flexible) substrate, and examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.
（陽極）
　基板上に形成される陽極には、仕事関数の大きい（具体的には４．０ｅＶ以上）金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。具体的には、例えば、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ　Ｔｉｎ　Ｏｘｉｄｅ）、珪素若しくは酸化珪素を含有した酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステン、及び酸化亜鉛を含有した酸化インジウム、グラフェン等が挙げられる。この他、金（Ａｕ）、白金（Ｐｔ）、又は金属材料の窒化物（例えば、窒化チタン）等が挙げられる。 (anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , Graphene and the like. In addition, gold (Au), platinum (Pt), or a nitride of a metal material (for example, titanium nitride) or the like can be used.
（正孔注入層）
　正孔注入層は、正孔注入性の高い物質を含む層である。正孔注入性の高い物質としては、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物、芳香族アミン化合物、又は高分子化合物（オリゴマー、デンドリマー、ポリマー等）等も使用できる。 (Hole injection layer)
The hole-injection layer is a layer containing a substance having a high hole-injection property. As the substance having a high hole injecting property, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, an aromatic amine compound, or a high molecular compound (oligomer, dendrimer, polymer, etc.) can also be used.
（正孔輸送層）
　正孔輸送層は、正孔輸送性の高い物質を含む層である。正孔輸送層には、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体等を使用する事ができる。ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）やポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）等の高分子化合物を用いることもできる。但し、電子よりも正孔の輸送性の高い物質であれば、これら以外のものを用いてもよい。尚、正孔輸送性の高い物質を含む層は、単層のものだけでなく、上記物質からなる層が二層以上積層したものとしてもよい。 (Hole transport layer)
The hole-transporting layer is a layer containing a substance having a high hole-transporting property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. A high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, a substance other than these substances may be used as long as it has a property of transporting more holes than electrons. Note that the layer containing a substance having a high hole-transporting property is not limited to a single layer and may be a stack of two or more layers containing any of the above substances.
（発光層のゲスト材料）
　発光層は、発光性の高い物質を含む層であり、種々の材料を用いることができる。例えば、発光性の高い物質としては、蛍光を発光する蛍光性化合物や燐光を発光する燐光性化合物を用いることができる。蛍光性化合物は一重項励起状態から発光可能な化合物であり、燐光性化合物は三重項励起状態から発光可能な化合物である。
　発光層に用いることができる青色系の蛍光発光材料として、ピレン誘導体、スチリルアミン誘導体、クリセン誘導体、フルオランテン誘導体、フルオレン誘導体、ジアミン誘導体、トリアリールアミン誘導体等が使用できる。発光層に用いることができる緑色系の蛍光発光材料として、芳香族アミン誘導体等を使用できる。発光層に用いることができる赤色系の蛍光発光材料として、テトラセン誘導体、ジアミン誘導体等が使用できる。
　発光層に用いることができる青色系の燐光発光材料として、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体が使用される。発光層に用いることができる緑色系の燐光発光材料としてイリジウム錯体等が使用される。発光層に用いることができる赤色系の燐光発光材料として、イリジウム錯体、白金錯体、テルビウム錯体、ユーロピウム錯体等の金属錯体が使用される。 (Guest material of the light emitting layer)
The light emitting layer is a layer containing a substance having a high light emitting property, and various materials can be used. For example, as the substance having a high light emitting property, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound capable of emitting light from a singlet excited state, and a phosphorescent compound is a compound capable of emitting light from a triplet excited state.
As the blue fluorescent material that can be used in the light emitting layer, pyrene derivative, styrylamine derivative, chrysene derivative, fluoranthene derivative, fluorene derivative, diamine derivative, triarylamine derivative and the like can be used. An aromatic amine derivative or the like can be used as a green fluorescent material that can be used in the light emitting layer. A tetracene derivative, a diamine derivative, or the like can be used as a red fluorescent light emitting material that can be used in the light emitting layer.
A metal complex such as an iridium complex, an osmium complex, or a platinum complex is used as a blue phosphorescent material that can be used for the light emitting layer. An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer. A metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used as a red phosphorescent light emitting material that can be used for the light emitting layer.
（発光層のホスト材料）
　発光層としては、上述した発光性の高い物質（ゲスト材料）を他の物質（ホスト材料）に分散させた構成としてもよい。発光性の高い物質を分散させるための物質としては、各種のものを用いることができ、発光性の高い物質よりも最低空軌道準位（ＬＵＭＯ準位）が高く、最高被占有軌道準位（ＨＯＭＯ準位）が低い物質を用いることが好ましい。
　発光性の高い物質を分散させるための物質（ホスト材料）としては、１）アルミニウム錯体、ベリリウム錯体、若しくは亜鉛錯体等の金属錯体、２）オキサジアゾール誘導体、ベンゾイミダゾール誘導体、若しくはフェナントロリン誘導体等の複素環化合物、３）カルバゾール誘導体、アントラセン誘導体、フェナントレン誘導体、ピレン誘導体、若しくはクリセン誘導体等の縮合芳香族化合物、３）トリアリールアミン誘導体、若しくは縮合多環芳香族アミン誘導体等の芳香族アミン化合物が使用される。 (Host material for light emitting layer)
The light-emitting layer may have a structure in which the above-described substance having a high light-emitting property (guest material) is dispersed in another substance (host material). As a substance for dispersing a substance having a high light emitting property, various substances can be used, the lowest unoccupied orbital level (LUMO level) is higher than that of a substance having a high light emitting property, and the highest occupied orbital level ( It is preferable to use a substance having a low HOMO level).
As a substance (host material) for dispersing a substance having a high light-emitting property, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, etc. A heterocyclic compound, 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative or a chrysene derivative, 3) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, used.
（電子輸送層）
　電子輸送層は、電子輸送性の高い物質を含む層である。電子輸送層には、１）アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体、２）イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物、３）高分子化合物を使用することができる。 (Electron transport layer)
The electron-transporting layer is a layer containing a substance having a high electron-transporting property. In the electron transport layer, 1) a metal complex such as an aluminum complex, a beryllium complex or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative or a phenanthroline derivative, 3) a polymer compound Can be used.
　電子輸送層に含まれるフェナントロリン誘導体としては、式（６１）で表される化合物が好ましい。
Figure JPOXMLDOC01-appb-C000210
 As the phenanthroline derivative contained in the electron transport layer, the compound represented by the formula (61) is preferable.
Figure JPOXMLDOC01-appb-C000210
［式（６１）中、
　Ｘ６１～Ｘ６８は、それぞれ独立に、式（Ｂ）で表される基と結合する炭素原子、Ｎ又はＣＲ６１である。Ｘ６１～Ｘ６８のうち少なくとも１つが式（Ｂ）で表される基と結合する炭素原子である。
　Ｒ６１は、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
　Ｒ６１が２個以上存在する場合、２個以上のＲ６１は、互いに同一であってもよいし、異なっていてもよい。Ｒ６１は、隣接する他のＲ６１と結合して環を形成しない。
　Ｌ６１は、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
　ｃは、０～８の整数である。
ｃが０のとき、Ｌ６１は単結合である。ｃが２以上のとき、２以上のＬ６１は互いに同一であってもよいし、異なっていてもよい。
　Ｂ６１は、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
　ｂは、１～５の整数であり、ｂが２以上のとき、２以上のＢ６１は、互いに同一であってもよいし、異なっていてもよい。］ [In Formula (61),
X 61 to X 68 are each independently a carbon atom bonded to the group represented by formula (B), N or CR 61 . At least one of X 61 to X 68 is a carbon atom bonded to the group represented by formula (B).
R 61 is
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-( R904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
When two or more R 61's are present, the two or more R 61 's may be the same as or different from each other. R 61 does not form a ring by combining with another adjacent R 61 .
L 61 is
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
c is an integer of 0-8.
When c is 0, L 61 is a single bond. When c is 2 or more, the two or more L 61 may be the same as or different from each other.
B 61 is
It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
b is an integer of 1 to 5, and when b is 2 or more, B 61 of 2 or more may be the same as or different from each other. ]
　上記式（６１）における各置換基の詳細は、本明細書の［定義］の欄に記載の通りである。
　以下に、式（６１）で表される化合物の具体例を記載するが、これらは例示に過ぎず、式（６１）で表される化合物は下記具体例に限定されるものではない。 Details of each substituent in the above formula (61) are as described in the section of “Definition” in the present specification.
Hereinafter, specific examples of the compound represented by the formula (61) will be described, but these are merely examples, and the compound represented by the formula (61) is not limited to the following specific examples.
Figure JPOXMLDOC01-appb-C000211
Figure JPOXMLDOC01-appb-C000211
（電子注入層）
　電子注入層は、電子注入性の高い物質を含む層である。電子注入層には、リチウム（Ｌｉ）、イッテルビウム（Ｙｂ）、フッ化リチウム（ＬｉＦ）、フッ化セシウム（ＣｓＦ）、フッ化カルシウム（ＣａＦ２）、８－ヒドロキシキノリノラト－リチウム（Ｌｉｑ）等の金属錯体化合物、リチウム酸化物（ＬｉＯｘ）等のアルカリ金属、アルカリ土類金属、又はそれらの化合物を用いることができる。 (Electron injection layer)
The electron-injection layer is a layer containing a substance having a high electron-injection property. For the electron injection layer, lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), 8-hydroxyquinolinolato-lithium (Liq), etc. The metal complex compound, alkali metal such as lithium oxide (LiO x ), alkaline earth metal, or a compound thereof can be used.
（陰極）
　陰極には、仕事関数の小さい（具体的には３．８ｅＶ以下）金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第１族又は第２族に属する元素、即ち、リチウム（Ｌｉ）やセシウム（Ｃｓ）等のアルカリ金属、及びマグネシウム（Ｍｇ）、カルシウム（Ｃａ）、ストロンチウム（Ｓｒ）等のアルカリ土類金属、及びこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）、イッテルビウム（Ｙｂ）等の希土類金属及びこれらを含む合金等が挙げられる。 (cathode)
For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less). Specific examples of such 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), and magnesium (Mg), calcium ( Ca), alkaline earth metals such as strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
　第１の態様の有機ＥＬ素子において、各層の形成方法は特に限定されない。従来公知の真空蒸着法、スピンコーティング法等による形成方法を用いることができる。発光層等の各層は、真空蒸着法、分子線蒸着法（ＭＢＥ法）あるいは溶媒に解かした溶液のディッピング法、スピンコーティング法、キャスティング法、バーコート法、ロールコート法等の塗布法による公知の方法で形成することができる。 In the organic EL element of the first aspect, the method of forming each layer is not particularly limited. A conventionally known forming method such as a vacuum vapor deposition method and 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) or a solvent-dissolved solution dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like. Can be formed by a method.
　第１の態様の有機ＥＬ素子において、各層の膜厚は特に制限されないが、一般にピンホール等の欠陥を抑制し、印加電圧を低く抑え、発光効率をよくするため、通常は数ｎｍから１μｍの範囲が好ましい。 In the organic EL device of the first aspect, the film thickness of each layer is not particularly limited, but in general, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and improve the luminous efficiency, it is usually several nm to 1 μm. A range is preferred.
［電子機器］
　本発明の第６の態様である電子機器は、上記第１～第５の態様の有機エレクトロルミネッセンス素子を備えることを特徴とする。
　電子機器の具体例としては、有機ＥＬパネルモジュール等の表示部品、テレビ、携帯電話、又はパーソナルコンピュータ等の表示装置、及び、照明、又は車両用灯具等の発光装置等が挙げられる。 [Electronics]
An electronic apparatus according to a sixth aspect of the present invention is characterized by including the organic electroluminescence element according to any of the first to fifth aspects.
Specific examples of the electronic device include a display component such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, and a light-emitting device such as lighting or a vehicle lamp.
　次に、実施例及び比較例を挙げて本発明をさらに詳しく説明するが、本発明はこれらの実施例の記載内容に何ら制限されるものではない。 Next, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the description of these Examples.
＜化合物＞
　実施例１～２０の有機ＥＬ素子の製造に用いた、式（１）で表される化合物を以下に示す。
Figure JPOXMLDOC01-appb-C000212
 <Compound>
The compounds represented by the formula (1) used for producing the organic EL devices of Examples 1 to 20 are shown below.
Figure JPOXMLDOC01-appb-C000212
　実施例１～２０の有機ＥＬ素子の製造に用いた化合物Ａを以下に示す。
Figure JPOXMLDOC01-appb-C000213
 Compound A used in the production of the organic EL devices of Examples 1 to 20 is shown below.
Figure JPOXMLDOC01-appb-C000213
　実施例１～２０の有機ＥＬ素子の製造に用いた、式（２１）で表される化合物を以下に示す。
Figure JPOXMLDOC01-appb-C000214
 The compounds represented by the formula (21) used for producing the organic EL devices of Examples 1 to 20 are shown below.
Figure JPOXMLDOC01-appb-C000214
　実施例１～２０の有機ＥＬ素子の製造に用いた、式（４１）で表される化合物を以下に示す。
Figure JPOXMLDOC01-appb-C000215
 The compounds represented by the formula (41) used for producing the organic EL devices of Examples 1 to 20 are shown below.
Figure JPOXMLDOC01-appb-C000215
　実施例１～２０及び比較例１～５の有機ＥＬ素子の製造に用いた、他の化合物の構造を以下に示す。尚、化合物ＥＴ－２は式（６１）で表される化合物である。
Figure JPOXMLDOC01-appb-C000216
 The structures of other compounds used in the production of the organic EL devices of Examples 1 to 20 and Comparative Examples 1 to 5 are shown below. The compound ET-2 is a compound represented by the formula (61).
Figure JPOXMLDOC01-appb-C000216
　比較例１～５の有機ＥＬ素子の製造に用いた化合物を以下に示す。
Figure JPOXMLDOC01-appb-C000217
 The compounds used for producing the organic EL devices of Comparative Examples 1 to 5 are shown below.
Figure JPOXMLDOC01-appb-C000217
＜有機ＥＬ素子の作製＞
　有機ＥＬ素子を以下のように作製し、評価した。
実施例１
（有機ＥＬ素子の作製）
　２５ｍｍ×７５ｍｍ×１．１ｍｍ厚のＩＴＯ透明電極（陽極）付きガラス基板（ジオマティック株式会社製）をイソプロピルアルコール中で超音波洗浄を５分間行なった後、ＵＶオゾン洗浄を３０分間行なった。ＩＴＯの膜厚は、１３０ｎｍとした。
　洗浄後の透明電極付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極が形成されている側の面上に透明電極を覆うようにして化合物ＨＩ－１を蒸着し、膜厚５ｎｍのＨＩ－１膜を形成した。このＨＩ－１膜は、正孔注入層として機能する。 <Production of organic EL device>
An organic EL device was manufactured and evaluated as follows.
Example 1
(Production of organic EL element)
A 25 mm×75 mm×1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm.
The glass substrate with a transparent electrode after cleaning was mounted on a substrate holder of a vacuum vapor deposition apparatus, and compound HI-1 was vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, and the film thickness was 5 nm. HI-1 film was formed. This HI-1 film functions as a hole injection layer.
　このＨＩ－１膜の成膜に続けて化合物ＨＴ－２を蒸着し、ＨＩ－１膜上に膜厚８０ｎｍのＨＴ－２膜を成膜した。このＨＴ－２膜は正孔輸送層（第１正孔輸送層）として機能する。
　ＨＴ－２膜の成膜に続けて化合物ＥＢＬ－２を蒸着し、ＨＴ－２膜上に膜厚１０ｎｍのＥＢＬ－２膜を成膜した。このＥＢＬ－２膜は電子阻止層（第２正孔輸送層）として機能する。
　ＥＢＬ－２膜上に化合物ＢＨ－４（ホスト材料）及び化合物ＢＤ－１（ドーパント材料）を化合物ＢＤ－１の割合が２質量％となるように共蒸着し、膜厚２５ｎｍのＢＨ－１：ＢＤ－１膜を成膜した。このＢＨ－４：ＢＤ－１膜は発光層として機能する。 Following formation of this HI-1 film, compound HT-2 was vapor-deposited to form an HT-2 film having a film thickness of 80 nm on the HI-1 film. This HT-2 film functions as a hole transport layer (first hole transport layer).
Following the formation of the HT-2 film, the compound EBL-2 was vapor-deposited to form an EBL-2 film having a film thickness of 10 nm on the HT-2 film. This EBL-2 film functions as an electron blocking layer (second hole transport layer).
Compound BH-4 (host material) and compound BD-1 (dopant material) were co-evaporated on the EBL-2 film so that the ratio of compound BD-1 was 2% by mass, and BH-1 having a film thickness of 25 nm: A BD-1 film was formed. This BH-4:BD-1 film functions as a light emitting layer.
　この発光層上に化合物ＨＢＬ－１を蒸着して、膜厚１０ｎｍのＨＢＬ－１膜を形成した。このＨＢＬ－１膜は第１電子輸送層として機能する。
　このＨＢＬ－１膜上に化合物ＥＴ－２及びＬｉを、Ｌｉの割合が４質量％となるように共蒸着して、膜厚１５ｎｍのＥＴ－２：Ｌｉ膜を成膜した。このＥＴ－２：Ｌｉ膜は第２電子輸送層として機能する。このＥＴ－１膜上にＬｉＦを蒸着して、膜厚１ｎｍのＬｉＦ膜を形成した。このＥＴ－２：Ｌｉ膜上に金属Ａｌを蒸着して、膜厚８０ｎｍの金属陰極を形成し、有機ＥＬ素子を作製した。 Compound HBL-1 was vapor-deposited on this light emitting layer to form a 10 nm thick HBL-1 film. This HBL-1 film functions as a first electron transport layer.
Compounds ET-2 and Li were co-evaporated on the HBL-1 film so that the ratio of Li was 4% by mass to form an ET-2:Li film having a film thickness of 15 nm. This ET-2:Li film functions as a second electron transport layer. LiF was vapor-deposited on this ET-1 film to form a LiF film having a film thickness of 1 nm. Metal Al was vapor-deposited on this ET-2:Li film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.
　得られた有機ＥＬ素子の層構成は下記のとおりである。
　ＩＴＯ（１３０）／ＨＩ－１（５）／ＨＴ－２（８０）／ＥＢＬ－２（１０）／ＢＨ－４：ＢＤ－１（２５：２質量％）／ＨＢＬ－１（１０）／ＥＴ－２：Ｌｉ（１５：４％）／Ａｌ（８０）
　尚、括弧内の数字は膜厚（単位：ｎｍ）を表す。 The layer structure of the obtained organic EL device is as follows.
ITO(130)/HI-1(5)/HT-2(80)/EBL-2(10)/BH-4:BD-1(25:2% by mass)/HBL-1(10)/ET- 2: Li(15:4%)/Al(80)
The numbers in parentheses represent the film thickness (unit: nm).
（有機ＥＬ素子の評価）
　電流密度が５０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加し、初期輝度に対して輝度が９０％となるまでの時間（ＬＴ９０＠５０ｍＡ／ｃｍ２）を測定した寿命ＬＴ９０（ｈｒ）の結果を表１に示す。 (Evaluation of organic EL element)
Life time LT90 (hr) measured by applying a voltage to the organic EL element so that the current density becomes 50 mA/cm 2 and measuring the time (LT90 @ 50 mA/cm 2 ) until the brightness becomes 90% of the initial brightness. The results are shown in Table 1.
実施例２～５
　ドーパント材料、ホスト材料及び第１電子輸送層において、表１に示す化合物を用いた以外は、実施例１と同じ方法で有機ＥＬ素子を作製し、評価した。結果を表１に示す。 Examples 2-5
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in Table 1 were used in the dopant material, the host material and the first electron transport layer. The results are shown in Table 1.
Figure JPOXMLDOC01-appb-T000218
Figure JPOXMLDOC01-appb-T000218
実施例６
（有機ＥＬ素子の作製）
　ＨＩ－１膜までは、実施例１と同様にした。
　このＨＩ－１膜の成膜に続けて化合物ＨＴ－１を蒸着し、ＨＩ－１膜上に膜厚８０ｎｍのＨＴ－１膜を成膜した。このＨＴ－１膜は正孔輸送層（第１正孔輸送層）として機能する。
　ＨＴ－１膜の成膜に続けて化合物ＥＢＬ－１を蒸着し、ＨＴ－１膜上に膜厚１０ｎｍのＥＢＬ－１膜を成膜した。このＥＢＬ－１膜は電子阻止層（第２正孔輸送層）として機能する。
　ＥＢＬ－１膜上に化合物ＢＨ－１（ホスト材料）及び化合物ＢＤ－２（ドーパント材料）を化合物ＢＤ－２の割合が２質量％となるように共蒸着し、膜厚２５ｎｍのＢＨ－１：ＢＤ－２膜を成膜した。このＢＨ－１：ＢＤ－２膜は発光層として機能する。 Example 6
(Production of organic EL element)
The process up to the HI-1 film was the same as in Example 1.
Following formation of this HI-1 film, compound HT-1 was vapor-deposited to form an HT-1 film having a film thickness of 80 nm on the HI-1 film. This HT-1 film functions as a hole transport layer (first hole transport layer).
Following formation of the HT-1 film, the compound EBL-1 was vapor-deposited to form an EBL-1 film having a film thickness of 10 nm on the HT-1 film. This EBL-1 film functions as an electron blocking layer (second hole transport layer).
Compound BH-1 (host material) and compound BD-2 (dopant material) were co-evaporated on the EBL-1 film so that the ratio of compound BD-2 was 2% by mass, and BH-1 having a film thickness of 25 nm: A BD-2 film was formed. This BH-1:BD-2 film functions as a light emitting layer.
　この発光層上に化合物ＨＢＬ－３を蒸着して、膜厚１０ｎｍのＨＢＬ－３膜を形成した。このＨＢＬ－３膜は第１電子輸送層として機能する。
　このＨＢＬ－３膜上に化合物ＥＴ－１を蒸着して、膜厚１５ｎｍのＥＴ－１膜を成膜した。このＥＴ－１膜は第２電子輸送層として機能する。このＥＴ－１膜上にＬｉＦを蒸着して、膜厚１ｎｍのＬｉＦ膜を形成した。このＬｉＦ膜上に金属Ａｌを蒸着して、膜厚８０ｎｍの金属陰極を形成し、有機ＥＬ素子を作製した。 A compound HBL-3 was vapor-deposited on this light emitting layer to form an HBL-3 film having a film thickness of 10 nm. This HBL-3 film functions as a first electron transport layer.
Compound ET-1 was vapor-deposited on this HBL-3 film to form an ET-1 film having a film thickness of 15 nm. This ET-1 film functions as a second electron transport layer. LiF was vapor-deposited on this ET-1 film to form a LiF film having a film thickness of 1 nm. Metal Al was vapor-deposited on this LiF film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.
　得られた有機ＥＬ素子の層構成は下記のとおりである。
　ＩＴＯ（１３０）／ＨＩ－１（５）／ＨＴ－１（８０）／ＥＢＬ－１（１０）／ＢＨ－１：ＢＤ－２（２５：２質量％）／ＨＢＬ－３（１０）／ＥＴ－１（１５）／ＬｉＦ（１）／Ａｌ（８０）
　尚、括弧内の数字は膜厚（単位：ｎｍ）を表す。
　得られた有機ＥＬ素子を、実施例１と同じ方法で評価した。結果を表２に示す。 The layer structure of the obtained organic EL device is as follows.
ITO(130)/HI-1(5)/HT-1(80)/EBL-1(10)/BH-1:BD-2(25:2% by mass)/HBL-3(10)/ET- 1(15)/LiF(1)/Al(80)
The numbers in parentheses represent the film thickness (unit: nm).
The obtained organic EL device was evaluated by the same method as in Example 1. The results are shown in Table 2.
実施例７，８、比較例１
　化合物ＢＨ－１に代えて、表２に示す化合物を用いたこと以外は、実施例６と同じ方法で有機ＥＬ素子を作製し、評価した。結果を表２に示す。 Examples 7, 8 and Comparative Example 1
An organic EL device was prepared and evaluated in the same manner as in Example 6 except that the compounds shown in Table 2 were used instead of the compound BH-1. The results are shown in Table 2.
Figure JPOXMLDOC01-appb-T000219
Figure JPOXMLDOC01-appb-T000219
　表２の結果から、２置換のアントラセン化合物を用いた比較例に比べて、３置換のアントラセン化合物を用いた実施例は、駆動電圧が低く、かつ、素子寿命が大きく向上していることがわかる。 From the results in Table 2, it can be seen that, as compared with the comparative example using the 2-substituted anthracene compound, the example using the 3-substituted anthracene compound has a lower driving voltage and a greatly improved device life. ..
実施例９
　下記表３に示すドーパント材料及びホスト材料を用い、実施例６で用いた化合物ＨＢＬ－３の代わりに化合物ＨＢＬ－１を用いた以外は実施例６と同様にして有機ＥＬ素子を作製した。
　得られた有機ＥＬ素子の層構成は下記のとおりである。
　ＩＴＯ（１３０）／ＨＩ－１（５）／ＨＴ－１（８０）／ＥＢＬ－１（１０）／ＢＨ－７：ＢＤ－１（２５：２質量％）／ＨＢＬ－１（１０）／ＥＴ－１（１５）／ＬｉＦ（１）／Ａｌ（８０）
　尚、括弧内の数字は膜厚（単位：ｎｍ）を表す。
　得られた有機ＥＬ素子を、実施例６と同じ方法で評価した。結果を表３に示す。 Example 9
An organic EL device was produced in the same manner as in Example 6 except that the compound HBL-1 used in Example 6 was used instead of the compound HBL-3 used in Example 6 using the dopant materials and host materials shown in Table 3 below.
The layer structure of the obtained organic EL device is as follows.
ITO(130)/HI-1(5)/HT-1(80)/EBL-1(10)/BH-7:BD-1(25:2% by mass)/HBL-1(10)/ET- 1(15)/LiF(1)/Al(80)
The numbers in parentheses represent the film thickness (unit: nm).
The obtained organic EL device was evaluated by the same method as in Example 6. The results are shown in Table 3.
実施例１０
　化合物ＢＨ－７に代えて、表３に示す化合物を用いた以外は、実施例９と同じ方法で有機ＥＬ素子を作製し、評価した。結果を表３に示す。 Example 10
An organic EL device was prepared and evaluated in the same manner as in Example 9 except that the compounds shown in Table 3 were used instead of the compound BH-7. The results are shown in Table 3.
Figure JPOXMLDOC01-appb-T000220
Figure JPOXMLDOC01-appb-T000220
実施例１１
　ドーパント材料ＢＤ－１の代わりにＢＤ－３を用い、下記表４に示すホスト材料を用いた以外は実施例９と同様にして有機ＥＬ素子を作製し、評価した。結果を表４に示す。 Example 11
An organic EL device was prepared and evaluated in the same manner as in Example 9 except that BD-3 was used instead of the dopant material BD-1 and the host materials shown in Table 4 below were used. The results are shown in Table 4.
実施例１２～１５
　表４に示すホスト材料を用いた以外は実施例１１と同様にして有機ＥＬ素子を作製し、評価した。結果を表４に示す。 Examples 12 to 15
An organic EL device was prepared and evaluated in the same manner as in Example 11 except that the host materials shown in Table 4 were used. The results are shown in Table 4.
Figure JPOXMLDOC01-appb-T000221
Figure JPOXMLDOC01-appb-T000221
実施例１６
　表５に示すドーパント材料及びホスト材料を用い、実施例６で用いた化合物ＨＴ－１の代わりに化合物ＨＴ－２を、化合物ＥＢＬ－２の代わりに化合物ＨＴ－２を、を用いた以外は実施例６と同様にして有機ＥＬ素子を作製した。
　得られた有機ＥＬ素子の層構成は下記のとおりである。
　ＩＴＯ（１３０）／ＨＩ－１（５）／ＨＴ－１（１０）／ＥＢＬ－１（１０）／ＢＨ－４：ＢＤ－４（２５：２質量％）／ＨＢＬ－１（１０）／ＥＴ－１（１５）／ＬｉＦ（１）／Ａｌ（８０）
　尚、括弧内の数字は膜厚（単位：ｎｍ）を表す。
　得られた有機ＥＬ素子を、実施例６と同じ方法で評価した。結果を表５に示す。 Example 16
Using the dopant materials and host materials shown in Table 5, except that the compound HT-2 used in Example 6 was replaced with the compound HT-2, and the compound EBL-2 was replaced with the compound HT-2. An organic EL device was produced in the same manner as in Example 6.
The layer structure of the obtained organic EL device is as follows.
ITO(130)/HI-1(5)/HT-1(10)/EBL-1(10)/BH-4:BD-4(25:2% by mass)/HBL-1(10)/ET- 1(15)/LiF(1)/Al(80)
The numbers in parentheses represent the film thickness (unit: nm).
The obtained organic EL device was evaluated by the same method as in Example 6. The results are shown in Table 5.
比較例２
　表５に示すホスト材料を用いた以外は実施例１６と同様にして有機ＥＬ素子を作製し、評価した。結果を表５に示す。 Comparative example 2
An organic EL device was prepared and evaluated in the same manner as in Example 16 except that the host materials shown in Table 5 were used. The results are shown in Table 5.
Figure JPOXMLDOC01-appb-T000222
Figure JPOXMLDOC01-appb-T000222
実施例１７及び比較例３
　表６に示すドーパント材料及びホスト材料を用いた以外は実施例１６と同様にして有機ＥＬ素子を作製し、評価した。結果を表６に示す。 Example 17 and Comparative Example 3
An organic EL device was prepared and evaluated in the same manner as in Example 16 except that the dopant materials and host materials shown in Table 6 were used. The results are shown in Table 6.
Figure JPOXMLDOC01-appb-T000223
Figure JPOXMLDOC01-appb-T000223
実施例１８及び比較例４
　表７に示すドーパント材料及びホスト材料を用いた以外は実施例１６と同様にして有機ＥＬ素子を作製し、評価した。結果を表７に示す。 Example 18 and Comparative Example 4
An organic EL device was prepared and evaluated in the same manner as in Example 16 except that the dopant materials and host materials shown in Table 7 were used. The results are shown in Table 7.
Figure JPOXMLDOC01-appb-T000224
Figure JPOXMLDOC01-appb-T000224
　表３～７の結果から、２置換のアントラセン化合物を用いた比較例に比べて、３置換のアントラセン化合物を用いた実施例は、駆動電圧が低く、かつ、素子寿命が大きく向上していることがわかる。 From the results of Tables 3 to 7, in comparison with the comparative example using the 2-substituted anthracene compound, the example using the 3-substituted anthracene compound had a lower driving voltage and greatly improved the device life. I understand.
＜タンデム型有機ＥＬ素子の作製＞
実施例１９
（有機ＥＬ素子の作製）
　２５ｍｍ×７５ｍｍ×１．１ｍｍ厚のＩＴＯ透明電極（陽極）付きガラス基板（ジオマテック株式会社製）を、イソプロピルアルコール中で５分間超音波洗浄を行った後、ＵＶオゾン洗浄を１分間行った。ＩＴＯの膜厚は、１３０ｎｍとした。
・第１発光ユニットの形成
　洗浄後の透明電極ライン付き前記ガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に透明電極を覆うようにして化合物ＨＴ－３と、化合物ＨＩ－２とを共蒸着し、膜厚１０ｎｍの正孔注入層を形成した。正孔注入層における化合物ＨＴ－３の濃度を９７質量％とし、化合物ＨＩ－２の濃度を３質量％とした。
　次に、正孔注入層上に、化合物ＨＴ－３を蒸着し、膜厚７０ｎｍの第１正孔輸送層を形成した。
　次に、この第１正孔輸送層上に、化合物ＥＢＬ－３を蒸着し、膜厚１０ｎｍの第２正孔輸送層を形成した。
　次に、この第２正孔輸送層上に、化合物ＢＨ－４と、化合物ＢＤ－１とを共蒸着し、膜厚２５ｎｍの第１発光層としての青色蛍光発光層を形成した。青色蛍光発光層における化合物ＢＨ－４の濃度を９８質量％とし、化合物ＢＤ－１の濃度を２質量％とした。
　次に、この青色蛍光発光層上に、化合物ＨＢＬ－１を蒸着し、膜厚１０ｎｍの電子輸送層を形成した。 <Production of tandem type organic EL device>
Example 19
(Production of organic EL element)
A 25 mm×75 mm×1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 1 minute. The film thickness of ITO was 130 nm.
-Formation of the first light-emitting unit The glass substrate with the transparent electrode line after cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and a compound is prepared by first covering the transparent electrode on the surface where the transparent electrode line is formed. HT-3 and compound HI-2 were co-evaporated to form a hole injection layer having a film thickness of 10 nm. The concentration of the compound HT-3 in the hole injection layer was 97% by mass, and the concentration of the compound HI-2 was 3% by mass.
Next, the compound HT-3 was vapor-deposited on the hole injection layer to form a 70-nm-thick first hole transport layer.
Next, the compound EBL-3 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.
Next, on this second hole transport layer, compound BH-4 and compound BD-1 were co-evaporated to form a blue fluorescent light emitting layer as a first light emitting layer having a film thickness of 25 nm. The concentration of the compound BH-4 and the concentration of the compound BD-1 in the blue fluorescent light emitting layer were 98% by mass and 2% by mass, respectively.
Next, the compound HBL-1 was vapor-deposited on the blue fluorescent emitting layer to form an electron transporting layer having a film thickness of 10 nm.
・第１電荷発生層の形成
　次に、この電子輸送層上に、化合物ＥＴ－２と、リチウム（Ｌｉ）とを共蒸着し、膜厚１０ｎｍの第１Ｎ層を形成した。第１Ｎ層における化合物ＥＴ－２の濃度を９６質量％とし、Ｌｉの濃度を４質量％とした。
　次に、この第１Ｎ層上に、化合物ＨＴ－３と、化合物ＨＩ－２とを共蒸着し、膜厚１０ｎｍの第１Ｐ層を形成した。第１Ｐ層における化合物ＨＴ－３の濃度を９０質量％とし、化合物ＨＩ－２の濃度を１０質量％とした。 -Formation of First Charge Generation Layer Next, the compound ET-2 and lithium (Li) were co-evaporated on the electron transport layer to form a first N layer having a thickness of 10 nm. The concentration of the compound ET-2 in the first N layer was 96% by mass, and the concentration of Li was 4% by mass.
Next, the compound HT-3 and the compound HI-2 were co-evaporated on the first N layer to form a first P layer having a film thickness of 10 nm. The concentration of the compound HT-3 in the first P layer was 90% by mass, and the concentration of the compound HI-2 was 10% by mass.
・第２発光ユニットの形成
　次に、この第１Ｐ層上に、化合物ＥＢＬ－３を蒸着し、膜厚１０ｎｍの第１正孔輸送層を形成した。
　次に、この第１正孔輸送層上に、化合物ＰＧＨ－１と、化合物ＰＧＤ－１とを共蒸着し、膜厚４８ｎｍの第２発光層としての黄色燐光発光層を形成した。黄色燐光発光層における化合物ＰＧＨ－１の濃度を８０質量％とし、化合物ＰＧＤ－１の濃度を２０質量％とした。
　次に、この黄色燐光発光層上に、化合物ＥＴ－１を蒸着し、膜厚１０ｎｍの電子輸送層を形成した。 -Formation of Second Light Emitting Unit Next, a compound EBL-3 was vapor-deposited on the first P layer to form a first hole transport layer having a film thickness of 10 nm.
Next, on this first hole transport layer, the compound PGH-1 and the compound PGD-1 were co-evaporated to form a yellow phosphorescent light emitting layer as a second light emitting layer having a film thickness of 48 nm. The concentration of the compound PGH-1 in the yellow phosphorescent-emitting layer was 80% by mass, and the concentration of the compound PGD-1 was 20% by mass.
Next, the compound ET-1 was vapor-deposited on the yellow phosphorescent-emitting layer to form an electron-transporting layer having a thickness of 10 nm.
・第２電荷発生層の形成
　次に、この電子輸送層上に、化合物ＥＴ－２と、リチウム（Ｌｉ）とを共蒸着し、膜厚３５ｎｍの第２Ｎ層を形成した。第２Ｎ層における化合物ＥＴ－２の濃度を９６質量％とし、Ｌｉの濃度を４質量％とした。
　次に、この第２Ｎ層上に、化合物ＨＴ－３と、化合物ＨＩ－２とを共蒸着し、膜厚１０ｎｍの第２Ｐ層を形成した。第２Ｐ層における化合物ＨＴ－３の濃度を９０質量％とし、化合物ＨＩ－２の濃度を１０質量％とした。 -Formation of Second Charge Generation Layer Next, the compound ET-2 and lithium (Li) were co-evaporated on the electron transport layer to form a second N layer having a thickness of 35 nm. The concentration of the compound ET-2 in the second N layer was 96% by mass, and the concentration of Li was 4% by mass.
Next, on this second N layer, compound HT-3 and compound HI-2 were co-evaporated to form a second P layer having a film thickness of 10 nm. The concentration of the compound HT-3 in the second P layer was 90% by mass, and the concentration of the compound HI-2 was 10% by mass.
・第３発光ユニットの形成
　次に、この第２Ｐ層上に、化合物ＨＴ－３を蒸着し、膜厚７０ｎｍの第１正孔輸送層を形成した。
　次に、この第１正孔輸送層上に、化合物ＥＢＬ－３を蒸着し、膜厚１０ｎｍの第２正孔輸送層を形成した。
　次に、この第２正孔輸送層上に、化合物ＢＨ－４と、化合物ＢＤ－１とを共蒸着し、膜厚２５ｎｍの第３発光層としての青色蛍光発光層を形成した。青色蛍光発光層における化合物ＢＨ－４の濃度を９８質量％とし、化合物ＢＤ－１の濃度を２質量％とした。
　次に、この青色蛍光発光層上に、化合物ＨＢＬ－１を蒸着し、膜厚１０ｎｍの第１電子輸送層を形成した。
　次に、この第１電子輸送層上に、化合物ＥＴ－１を蒸着し、膜厚１０ｎｍの第２電子輸送層を形成した。
　次に、この第２電子輸送層上に、フッ化リチウム（ＬｉＦ）を蒸着し、膜厚１ｎｍの電子注入層を形成した。
　そして、この電子注入層上に、金属アルミニウム（Ａｌ）を蒸着し、膜厚８０ｎｍの金属Ａｌ陰極を形成した。
　以上のようにして、ボトムエミッション型の有機ＥＬ素子を作製した。 -Formation of Third Light-Emitting Unit Next, a compound HT-3 was vapor-deposited on the second P layer to form a first hole-transporting layer having a film thickness of 70 nm.
Next, the compound EBL-3 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.
Next, on this second hole transport layer, compound BH-4 and compound BD-1 were co-evaporated to form a blue fluorescent light emitting layer as a third light emitting layer having a film thickness of 25 nm. The concentration of the compound BH-4 and the concentration of the compound BD-1 in the blue fluorescent light emitting layer were 98% by mass and 2% by mass, respectively.
Next, the compound HBL-1 was vapor-deposited on the blue fluorescent emitting layer to form a first electron transporting layer having a film thickness of 10 nm.
Next, the compound ET-1 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a film thickness of 10 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the second electron transport layer to form an electron injection layer having a film thickness of 1 nm.
Then, metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode having a film thickness of 80 nm.
As described above, a bottom emission type organic EL element was produced.
　得られた有機ＥＬ素子の層構成は下記の通りである。
　ＩＴＯ（１３０）／ＨＴ－３：ＨＩ－２（１０，９７％：３％）／ＨＴ－３（７０）／ＥＢＬ－３（１０）／ＢＨ－４：ＢＤ－１（２５，９８％：２％）／ＨＢＬ－１（１０）／ＥＴ－２：Ｌｉ（１０，９６％：４％）／ＨＴ－３：ＨＩ－２（１０，９０％：１０％）／ＥＢＬ－３（１０）／ＰＧＨ－１：ＰＧＤ－１（４８，８０％：２０％）／ＥＴ－１（１０）／ＥＴ－２：Ｌｉ（３５，９６％：４％）／ＨＴ－３：ＨＩ－２（１０，９０％：１０％）／ＨＴ－３（７０）／ＥＢＬ－３（１０）／ＢＨ－４：ＢＤ－１（２５，９８％：２％）／ＨＢＬ－１（１０）／ＥＴ－１（１０）／ＬｉＦ（１）／Ａｌ（８０）
　尚、括弧内の数字は膜厚（単位：ｎｍ）を表す。
　同じく括弧内において、パーセント表示された数字は、例えば、ＨＴ－３：ＨＩ－２（１０，９７％：３％）の場合、正孔注入層における化合物ＨＴ－３及び化合物ＨＩ－２の割合（質量％）が、ＨＴ－３：ＨＩ－２＝９７質量％：３質量％であることを示す。 The layer structure of the obtained organic EL device is as follows.
ITO(130)/HT-3:HI-2(10,97%:3%)/HT-3(70)/EBL-3(10)/BH-4:BD-1(25,98%:2) %)/HBL-1(10)/ET-2:Li(10,96%:4%)/HT-3:HI-2(10,90%:10%)/EBL-3(10)/PGH -1: PGD-1 (48, 80%: 20%)/ET-1 (10)/ET-2: Li (35, 96%: 4%)/HT-3: HI-2 (10, 90%) : 10%)/HT-3(70)/EBL-3(10)/BH-4: BD-1(25,98%:2%)/HBL-1(10)/ET-1(10)/ LiF(1)/Al(80)
The numbers in parentheses represent the film thickness (unit: nm).
Similarly, in parentheses, for example, in the case of HT-3:HI-2 (10,97%:3%), the figures expressed as percentages indicate the ratio of compound HT-3 and compound HI-2 in the hole injection layer ( Mass%) is HT-3:HI-2=97 mass%:3 mass %.
（有機ＥＬ素子の評価）
　得られた有機ＥＬ素子の初期の駆動電圧を、室温下、ＤＣ（直流）定電流１０ｍＡ／ｃｍ２駆動で測定した。結果を表８に示す。
　電流密度が５０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加し、初期輝度に対して輝度が９５％となるまでの時間（ＬＴ９５＠５０ｍＡ／ｃｍ２）を測定した寿命ＬＴ９５（ｈｒ）の結果を表８に示す。 (Evaluation of organic EL element)
The initial drive voltage of the obtained organic EL device was measured at room temperature under DC (direct current) constant current drive of 10 mA/cm 2 . The results are shown in Table 8.
Life time LT95 (hr) measured by applying a voltage to the organic EL element so that the current density becomes 50 mA/cm 2 and measuring the time (LT95 @ 50 mA/cm 2 ) until the brightness becomes 95% of the initial brightness. The results are shown in Table 8.
実施例２０及び比較例５
　第１発光層及び第３発光層において、下記表８に示すホスト材料及びドーパント材料を用いた以外は実施例１９と同様にして有機ＥＬ素子を作製し、実施例１９と同様に評価した。結果を表８に示す。 Example 20 and Comparative Example 5
An organic EL device was produced in the same manner as in Example 19 except that the host material and the dopant material shown in Table 8 below were used in the first light emitting layer and the third light emitting layer, and evaluated in the same manner as in Example 19. The results are shown in Table 8.
Figure JPOXMLDOC01-appb-T000225
Figure JPOXMLDOC01-appb-T000225
　表８の結果から、式（１）で表される３置換のアントラセン化合物ＢＨ－４及びＢＨ－５と、化合物ＢＤ－１との組み合わせは、２置換のアントラセン化合物Ｃｏｍｐ　ＢＨ－１と組み合わせた場合に比べて、低電圧駆動できる素子が得られることがわかる。 From the results of Table 8, the combination of the 3-substituted anthracene compounds BH-4 and BH-5 represented by the formula (1) and the compound BD-1 is shown in the case of the combination with the 2-substituted anthracene compound Comp BH-1. It can be seen that an element that can be driven at a low voltage can be obtained as compared with the above.
＜化合物の合成＞
合成例１：化合物ＢＤ－１の合成
　下記合成経路で、ＢＤ－１を合成した。
Figure JPOXMLDOC01-appb-C000226
 <Synthesis of compound>
Synthesis Example 1: Synthesis of Compound BD-1 BD-1 was synthesized by the following synthetic route.
Figure JPOXMLDOC01-appb-C000226
中間体１の合成
　アルゴン雰囲気下、２－ヨードニトロベンゼン（９．７ｇ、３９ｍｍｏｌ）、５－ブロモ－２－メトキシフェニルボロン酸（９．２ｇ、４０ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（Ｐｄ（ＰＰｈ３）４、１．１ｇ、０．９７５ｍｍｏｌ）、Ｋ３ＰＯ４（２１ｇ、９７ｍｍｏｌ）をエタノール（９５ｍＬ）に溶解させ、８時間還流した。反応終了後、溶媒を留去し、残渣をカラムクロマトグラフィで精製して黄色固体（８．８ｇ、収率７３％）を得た。得られた固体は目的物である中間体１であり、マススペクトル分析の結果、分子量３０８に対し、ｍ／ｅ＝３０８であった。 Synthesis of Intermediate 1 Under an argon atmosphere, 2-iodonitrobenzene (9.7 g, 39 mmol), 5-bromo-2-methoxyphenylboronic acid (9.2 g, 40 mmol), tetrakis(triphenylphosphine)palladium(0)( Pd(PPh 3 ) 4 , 1.1 g, 0.975 mmol) and K 3 PO 4 (21 g, 97 mmol) were dissolved in ethanol (95 mL), and the mixture was refluxed for 8 hours. After the reaction was completed, the solvent was distilled off and the residue was purified by column chromatography to obtain a yellow solid (8.8 g, yield 73%). The obtained solid was Intermediate 1, which was the target substance, and as a result of mass spectrum analysis, m/e was 308 with respect to the molecular weight of 308.
中間体２の合成
　中間体１（７．００ｇ、２２．７ｍｍｏｌ）をｏ－ジクロロベンゼン（８０ｍＬ）に溶解させ、トリフェニルホスフィン（１４．９ｇ、５６．８ｍｍｏｌ）を加え、１２時間還流した。反応終了後、溶媒を留去し、残渣をカラムクロマトグラフィで精製して白色固体（５．７ｇ、収率７８％）を得た。得られた固体は目的物である中間体２であり、マススペクトル分析の結果、分子量２７６に対し、ｍ／ｅ＝２７６であった。 Synthesis of Intermediate 2 Intermediate 1 (7.00 g, 22.7 mmol) was dissolved in o-dichlorobenzene (80 mL), triphenylphosphine (14.9 g, 56.8 mmol) was added, and the mixture was refluxed for 12 hours. After the reaction was completed, the solvent was distilled off, and the residue was purified by column chromatography to obtain a white solid (5.7 g, yield 78%). The obtained solid was the intermediate 2 which was the target, and as a result of mass spectrum analysis, it was m/e=276 with respect to the molecular weight of 276.
中間体３の合成
　アルゴン雰囲気下、中間体２（５．７ｇ、２１ｍｍｏｌ）、ピナコールボラン（７．９ｇ、６２ｍｍｏｌ）、ジクロロ［１，１’－ビス（ジフェニルフォスフィノ）フェロセン］パラジウム（ＰｄＣｌ２（ｄｐｐｆ）、１．５ｇ、２．０ｍｍｏｌ）をジオキサン（２５０ｍＬ）に溶解させ、トリエチルアミン（１１．５ｍＬ、８３ｍｍｏｌ）を加え、５時間還流した。反応終了後、溶媒を留去し、残渣をカラムクロマトグラフィで精製して黄色固体（５．０ｇ、収率７５％）を得た。得られた固体は目的物である中間体３であり、マススペクトル分析の結果、分子量３２３に対し、ｍ／ｅ＝３２３であった。 Synthesis of Intermediate 3 Under an argon atmosphere, Intermediate 2 (5.7 g, 21 mmol), pinacol borane (7.9 g, 62 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (PdCl 2 ( dppf), 1.5 g, 2.0 mmol) was dissolved in dioxane (250 mL), triethylamine (11.5 mL, 83 mmol) was added, and the mixture was refluxed for 5 hours. After completion of the reaction, the solvent was distilled off and the residue was purified by column chromatography to obtain a yellow solid (5.0 g, yield 75%). The obtained solid was Intermediate 3, which was the target substance, and the result of mass spectrum analysis was m/e=323 with respect to the molecular weight of 323.
中間体４の合成
　アルゴン雰囲気下、ジブロモジヨードベンゼン（２．５ｇ、５．１ｍｍｏｌ）、中間体３（４．９７ｇ、１５．４ｍｍｏｌ）、Ｐｄ（ＰＰｈ３）４（２３７ｍｇ、０．２０５ｍｍｏｌ）をトルエン（２５０ｍＬ）とジメチルスルホキシド（ＤＭＳＯ、５０ｍＬ）に溶解し、これに２Ｍ　Ｎａ２ＣＯ３水溶液（１３ｍＬ）を加え９０℃で２４時間過熱攪拌した。反応終了後、減圧下トルエンを除去し沈殿した固体をろ別した。この固体をメタノールと酢酸エチルで洗浄し白色固体（２．５ｇ、収率７５％）を得た。得られた固体は目的物である中間体４であり、マススペクトル分析の結果、分子量６２６に対し、ｍ／ｅ＝６２６であった。 Synthesis of Intermediate 4 Dibromodiiodobenzene (2.5 g, 5.1 mmol), Intermediate 3 (4.97 g, 15.4 mmol), Pd(PPh 3 ) 4 (237 mg, 0.205 mmol) were added under an argon atmosphere. It was dissolved in toluene (250 mL) and dimethylsulfoxide (DMSO, 50 mL), 2 M Na 2 CO 3 aqueous solution (13 mL) was added thereto, and the mixture was heated with stirring at 90° C. for 24 hours. After completion of the reaction, toluene was removed under reduced pressure and the precipitated solid was filtered off. This solid was washed with methanol and ethyl acetate to obtain a white solid (2.5 g, yield 75%). The obtained solid was the intermediate 4, which was the target substance, and as a result of mass spectrum analysis, m/e=626 with respect to the molecular weight of 626.
中間体５の合成
　アルゴン雰囲気下、中間体４（２．５ｇ、３．９９ｍｍｏｌ）、ＣｕＩ（７６ｍｇ、０．４０ｍｍｏｌ）、Ｌ－プロリン（９２ｍｇ、０．８０ｍｍｏｌ）、Ｋ２ＣＯ３（１．３８ｇ、１０ｍｍｏｌ）をＤＭＳＯ（８０ｍＬ）に懸濁し、１５０℃で６時間加熱攪拌した。反応終了後、沈殿した固体をろ別した。この固体をメタノールと酢酸エチルで洗浄し茶色固体（１．４ｇ、収率７５％）を得た。得られた固体は目的物である化合物５であり、マススペクトル分析の結果、分子量４６４に対し、ｍ／ｅ＝４６４であった。 Synthesis of Intermediate 5 Under an argon atmosphere, Intermediate 4 (2.5 g, 3.99 mmol), CuI (76 mg, 0.40 mmol), L-proline (92 mg, 0.80 mmol), K 2 CO 3 (1.38 g). 10 mmol) was suspended in DMSO (80 mL), and the mixture was heated with stirring at 150° C. for 6 hours. After the reaction was completed, the precipitated solid was filtered off. This solid was washed with methanol and ethyl acetate to obtain a brown solid (1.4 g, yield 75%). The obtained solid was the objective compound 5, and the result of mass spectrum analysis was m/e=464 with respect to the molecular weight of 464.
中間体６の合成
　中間体５（１．４ｇ、３．０ｍｍｏｌ）をジクロロメタン（１５０ｍＬ）に溶解させ、１ＭのＢＢｒ３のジクロロメタン溶液（１５ｍＬ、１５ｍｍｏｌ）を加え、８時間還流した。反応終了後、氷水（５０ｍＬ）を加え、沈殿をろ別した。この固体をメタノールで洗浄し白色固体（１．４ｇ）を得た。得られた固体は目的物である中間体６であり、マススペクトル分析の結果、分子量４３６に対し、ｍ／ｅ＝４３６であった。 Synthesis of Intermediate 6 Intermediate 5 (1.4 g, 3.0 mmol) was dissolved in dichloromethane (150 mL), 1 M BBr 3 in dichloromethane solution (15 mL, 15 mmol) was added, and the mixture was refluxed for 8 hours. After the reaction was completed, ice water (50 mL) was added, and the precipitate was filtered off. This solid was washed with methanol to obtain a white solid (1.4 g). The obtained solid was the target intermediate 6, and the result of mass spectrum analysis was m/e=436 with respect to the molecular weight of 436.
中間体７の合成
　中間体６（１．４ｇ、３．２ｍｍｏｌ）をジクロロメタン（７５ｍＬ）とピリジン（７５ｍＬ）に懸濁させ、無水トリフラート（３．８ｍＬ、２２．５ｍｍｏｌ）を加え室温で８時間攪拌した。反応終了後、水（５０ｍＬ）を加え、沈殿をろ別した。この固体をメタノールと酢酸エチルで洗浄し白色固体（１．８ｇ、収率７２％）を得た。得られた固体は目的物である中間体７であり、マススペクトル分析の結果、分子量７００に対し、ｍ／ｅ＝７００であった。 Synthesis of Intermediate 7 Intermediate 6 (1.4 g, 3.2 mmol) was suspended in dichloromethane (75 mL) and pyridine (75 mL), anhydrous triflate (3.8 mL, 22.5 mmol) was added, and the mixture was stirred at room temperature for 8 hours. did. After the reaction was completed, water (50 mL) was added and the precipitate was filtered off. This solid was washed with methanol and ethyl acetate to obtain a white solid (1.8 g, yield 72%). The obtained solid was the target intermediate 7, and the result of mass spectrum analysis was m/e=700 for a molecular weight of 700.
ＢＤ－１の合成
　アルゴン雰囲気下、中間体７（１．００ｇ、１．４３ｍｍｏｌ）、４－ｉＰｒ－Ｎ－フェニルアニリン（７５４ｍｇ、３．５７ｍｍｏｌ）、トリス(ジベンジリデンアセトン)ジパラジウム（０）（Ｐｄ２（ｄｂａ）３、２６ｍｇ、０．０２９ｍｍｏｌ）、ジ－ｔｅｒｔ－ブチル（１－メチル－２，２－ジフェニルシクロプロピル）ホスフィン（４０ｍｇ、０．１１ｍｍｏｌ）をキシレン（１２０ｍＬ）に溶解し、１Ｍのリチウムビス（トリメチルシリル）アミドのテトラヒドロフラン溶液（３．６ｍＬ、３．６ｍｍｏｌ）を加え、８時間還流した。反応終了後セライトろ過し、溶媒を留去して得られた固体をカラムクロマトグラフィで精製し黄色固体（３００ｍｇ、収率２６％）を得た。得られた固体は目的物であるＢＤ－１であり、マススペクトル分析の結果、分子量８２３に対し、ｍ／ｅ＝８２３であった。 Synthesis of BD-1 Under an argon atmosphere, Intermediate 7 (1.00 g, 1.43 mmol), 4-iPr-N-phenylaniline (754 mg, 3.57 mmol), tris(dibenzylideneacetone)dipalladium(0)( Pd 2 (dba) 3 , 26 mg, 0.029 mmol) and di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (40 mg, 0.11 mmol) were dissolved in xylene (120 mL) and dissolved in 1M. A tetrahydrofuran solution of lithium bis(trimethylsilyl)amide (3.6 mL, 3.6 mmol) was added, and the mixture was refluxed for 8 hours. After the reaction was completed, the mixture was filtered through Celite, the solvent was distilled off, and the obtained solid was purified by column chromatography to obtain a yellow solid (300 mg, yield 26%). The obtained solid was the target product, BD-1, and the result of mass spectrum analysis was m/e=823 with respect to the molecular weight of 823.
合成例２：化合物ＢＤ－２の合成
　下記合成経路で、ＢＤ－２を合成した。
Figure JPOXMLDOC01-appb-C000227
 Synthesis Example 2: Synthesis of Compound BD-2 BD-2 was synthesized by the following synthetic route.
Figure JPOXMLDOC01-appb-C000227
化合物１－１の合成
　アルゴン雰囲気下、３，６－ジ－ｔｅｒｔ－ブチルカルバゾール（１１．２ｇ、４０ｍｍｏｌ）をクロロホルム（２００ｍＬ）に溶解させ、Ｎ－ブロモスクシンイミド（７．１２ｇ）を加えて、室温で５時間攪拌した。反応終了後、溶媒を留去し、残渣をカラムクロマトグラフィで精製してアモルファス状固体（１４．４ｇ）を得た。得られた固体は目的物である化合物１－１であり、マススペクトル分析の結果、分子量３５８に対し、ｍ／ｅ＝３５８であった。 Synthesis of Compound 1-1 Under argon atmosphere, 3,6-di-tert-butylcarbazole (11.2 g, 40 mmol) was dissolved in chloroform (200 mL), N-bromosuccinimide (7.12 g) was added, and the mixture was stirred at room temperature. And stirred for 5 hours. After completion of the reaction, the solvent was distilled off and the residue was purified by column chromatography to obtain an amorphous solid (14.4 g). The obtained solid was the target compound, Compound 1-1. As a result of mass spectrum analysis, m/e was 358 with respect to a molecular weight of 358.
化合物１－２の合成
　アルゴン雰囲気下、化合物１－１（１４．４ｇ）、ビス（ピナコラト）ジボロン（１５．２ｇ、６０ｍｍｏｌ、１．５ｅｑ．）、ＰｄＣｌ２（ｄｐｐｆ）（１．４６ｇ、２．０ｍｍｏｌ、５％Ｐｄ）、酢酸カリウム（７．８５ｇ、８０ｍｍｏｌ）をジオキサン（２００ｍＬ）に懸濁させ、７時間還流した。反応終了後、ショートパスシリカゲルカラムクロマトグラフィーを通し、溶媒を留去した。得られた固体をヘキサン／酢酸エチル（９：１）で再結晶し白色固体（１２．１ｇ、収率７５％）を得た。得られた固体は目的物である化合物１－２であり、マススペクトル分析の結果、分子量４０５に対し、ｍ／ｅ＝４０５であった。 Synthesis of Compound 1-2 Under an argon atmosphere, compound 1-1 (14.4 g), bis(pinacolato)diboron (15.2 g, 60 mmol, 1.5 eq.), PdCl 2 (dppf) (1.46 g, 2. 0 mmol, 5% Pd) and potassium acetate (7.85 g, 80 mmol) were suspended in dioxane (200 mL), and the mixture was refluxed for 7 hours. After completion of the reaction, the solvent was distilled off by passing through a short-pass silica gel column chromatography. The obtained solid was recrystallized from hexane/ethyl acetate (9:1) to give a white solid (12.1 g, yield 75%). The obtained solid was the target compound, Compound 1-2. As a result of mass spectrum analysis, m/e was 405 with respect to a molecular weight of 405.
化合物１－３の合成
　アルゴン雰囲気下、ジブロモジヨードベンゼン（４．００ｇ、８．２０ｍｍｏｌ）、化合物１－２（６．８１ｇ、１６．８ｍｍｏｌ、１．０５ｅｑ．）、Ｐｄ（ＰＰｈ３）４（４７４ｍｇ、０．４１ｍｍｏｌ、５％Ｐｄ）を１，２－ジメトキシエタン（８００ｍＬ）に溶解し、これにＫ３ＰＯ４（１０．４ｇ、４９．２ｍｍｏｌ）を溶解した水（２００ｍＬ）を加え５０℃で２４時間過熱攪拌した。反応終了後、酢酸エチルを用いて抽出し、溶媒を留去した。得られた固体をカラムクロマトグラフィで精製して白色固体（５．０ｇ、収率７７％）を得た。得られた固体は目的物である化合物１－３であり、マススペクトル分析の結果、分子量７９０に対し、ｍ／ｅ＝７９０であった。 Synthesis of Compound 1-3 Under an argon atmosphere, dibromodiiodobenzene (4.00 g, 8.20 mmol), compound 1-2 (6.81 g, 16.8 mmol, 1.05 eq.), Pd(PPh 3 ) 4 ( 474 mg, 0.41 mmol, 5% Pd) was dissolved in 1,2-dimethoxyethane (800 mL), and water (200 mL) in which K 3 PO 4 (10.4 g, 49.2 mmol) was dissolved was added at 50° C. The mixture was heated and stirred for 24 hours. After completion of the reaction, extraction was performed with ethyl acetate, and the solvent was distilled off. The obtained solid was purified by column chromatography to obtain a white solid (5.0 g, yield 77%). The obtained solid was the target compound, Compound 1-3. As a result of mass spectrum analysis, m/e was 790 with respect to a molecular weight of 790.
ＢＤ－２の合成
　アルゴン雰囲気下、化合物１－３（２．００ｇ）、Ｐｄ２（ｄｂａ）３（２３２ｍｇ）、ＳＰｈｏｓ（４１５ｍｇ）、ＮａＯｔ－Ｂｕ（９７３ｍｇ）をキシレン（２００ｍＬ）に懸濁し、８時間還流した。反応終了後、シリカゲルカラムクロマトグラフィーで精製し、黄色固体（４５０ｍｇ、収率２８％）を得た。得られた固体は目的物である化合物１であり、マススペクトル分析の結果、分子量６２８に対し、ｍ／ｅ＝６２８であった。 Synthesis of BD-2 Compound 1-3 (2.00 g), Pd 2 (dba) 3 (232 mg), SPhos (415 mg), and NaOt-Bu (973 mg) were suspended in xylene (200 mL) under an argon atmosphere, and 8 Reflux for hours. After completion of the reaction, purification by silica gel column chromatography gave a yellow solid (450 mg, yield 28%). The obtained solid was the target compound, Compound 1. As a result of mass spectrum analysis, the molecular weight was 628, and m/e was 628.
　上記に本発明の実施形態及び／又は実施例を幾つか詳細に説明したが、当業者は、本発明の新規な教示及び効果から実質的に離れることなく、これら例示である実施形態及び／又は実施例に多くの変更を加えることが容易である。従って、これらの多くの変更は本発明の範囲に含まれる。
　この明細書に記載の文献、及び本願のパリ条約による優先権の基礎となる出願の内容を全て援用する。 Although some of the embodiments and/or examples of the present invention have been described in detail above, those skilled in the art may substantially without departing from the novel teachings and effects of the present invention. It is easy to make many changes to the embodiment. Therefore, many of these modifications are within the scope of the invention.
The entire contents of the documents described in this specification and the application which is the basis of the priority under the Paris Convention of the present application are incorporated.

Claims (35)

  1. 　陰極と、陽極と、前記陰極と前記陽極との間に有機層を有する有機エレクトロルミネッセンス素子であって、
    　前記有機層が、下記式（１）で表される化合物と、
    　下記式（１１－１）及び（１１－３）で表される化合物、又は下記式（１１－２）及び（１１－３）で表される化合物である、化合物Ａと、を含む、有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000001
     ［式（１）中、
    　Ｒ１～Ｒ８のうちの１個以上は、－Ｌ１３－Ａｒ１３である。
    　Ｌ１１～Ｌ１３は、それぞれ独立に、
    単結合、
    置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
    置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
    　Ｌ１３が２個以上存在する場合、２個以上のＬ１３は、互いに同一であってもよいし、異なっていてもよい。
    　Ａｒ１１～Ａｒ１３は、それぞれ独立に、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　Ａｒ１３が２個以上存在する場合、２個以上のＡｒ１３は、互いに同一であってもよいし、異なっていてもよい。
    　－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の炭素数２～５０のアルケニル基、
    置換もしくは無置換の炭素数２～５０のアルキニル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］
    Figure JPOXMLDOC01-appb-C000002
     [（式（１１－１）、式（１１－２）及び式（１１－３）中、
    　環Ａは、置換もしくは無置換の環形成炭素数１０～５０の縮合アリール環、置換もしくは無置換の環形成原子数８～５０の縮合複素環、又は下記式（Ｘ）で表されるベンゼン環である。）
    Figure JPOXMLDOC01-appb-C000003
     （式（Ｘ）中、
    　２つの＊で示す環形成炭素原子の一方で、前記式（１１－１）又は前記式（１１－２）のベンゼン環Ｂから延びる＊と結合し、他方で前記式（１１－３）のベンゼン環Ｃから延びる単結合と結合する。
    　前記式（１１－１）の２つの＊は、それぞれ、前記環Ａの前記縮合アリール環の環形成炭素原子、前記縮合複素環の環形成原子、又は前記式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合する。
    　前記式（１１－２）の３つの＊は、それぞれ、前記環Ａの前記縮合アリール環の環形成炭素原子、前記縮合複素環の環形成原子、又は前記式（Ｘ）で表されるベンゼン環の環形成炭素原子と結合する。）
    　Ｒ１０１～Ｒ１１６のうち隣接する２つ以上の１組以上は、置換もしくは無置換の飽和又は不飽和の環を形成するか、あるいは前記環を形成しない。
    　前記環を形成しないＲ１０１～Ｒ１１６、及びＲ１１７は、それぞれ独立に、
    水素原子、ハロゲン原子、シアノ基、ニトロ基、ハロアルキル基、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の炭素数２～５０のアルケニル基、
    置換もしくは無置換の炭素数２～５０のアルキニル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の炭素数７～５０のアラルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    －Ｃ（＝Ｏ）（Ｒ９０８）、
    －ＣＯＯ（Ｒ９０９）、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０９は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０９が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０９のそれぞれは同一でもよく、異なっていてもよい。
    　ｎは１又は２の整数である。ｎが２である場合、２つのＲ１１７は同じであってもよく、また、異なってもよい。]     A cathode, an anode, an organic electroluminescent element having an organic layer between the cathode and the anode,
    The organic layer is a compound represented by the following formula (1),
    An organic electroluminescent device containing a compound represented by the following formulas (11-1) and (11-3) or a compound A represented by the following formulas (11-2) and (11-3): Luminescence element.
    Figure JPOXMLDOC01-appb-C000001
     [In Formula (1),
    At least one of R 1 to R 8 is —L 13 —Ar 13 .
    L 11 to L 13 are each independently
    Single bond,
    A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
    When two or more L 13's are present, the two or more L 13 's may be the same as or different from each other.
    Ar 11 to Ar 13 are each independently
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    When two or more Ar 13's are present, the two or more Ar 13 's may be the same or different from each other.
    R 1 to R 8 which are not —L 13 —Ar 13 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
    Figure JPOXMLDOC01-appb-C000002
     [(In Formula (11-1), Formula (11-2) and Formula (11-3),
    Ring A is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms, or a benzene ring represented by the following formula (X). Is. )
    Figure JPOXMLDOC01-appb-C000003
     (In formula (X),
    One of the two ring-forming carbon atoms represented by * is bonded to * extending from the benzene ring B of the formula (11-1) or (11-2), and the other benzene of the formula (11-3). Bond with a single bond extending from ring C.
    The two * in the formula (11-1) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of.
    The three *'s in the formula (11-2) are each a ring-forming carbon atom of the condensed aryl ring of the ring A, a ring-forming atom of the condensed heterocycle, or a benzene ring represented by the formula (X). Bond to the ring-forming carbon atom of. )
    One or more adjacent two or more sets of R 101 to R 116 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
    R 101 to R 116 and R 117 that do not form a ring are each independently
    Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    -C(=O)(R 908 ),
    -COO (R 909 ),
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    R 901 to R 909 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two or more R 901 to R 909 are present, each of the two or more R 901 to R 909 may be the same or different.
    n is an integer of 1 or 2. When n is 2, the two R 117 may be the same or different. ]
  2. 　前記式（１）におけるＬ１１～Ｌ１３が、それぞれ独立に、単結合、又は
    置換もしくは無置換の環形成炭素数６～５０のアリーレン基である、請求項１に記載の有機エレクトロルミネッセンス素子。     The organic electroluminescent device according to claim 1, wherein L 11 to L 13 in the formula (1) are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
  3. 　前記式（１）におけるＬ１１～Ｌ１３が、それぞれ独立に、単結合、又は
    置換もしくは無置換のフェニレン基、
    置換もしくは無置換のビフェニレン基、
    置換もしくは無置換のターフェニレン基、
    置換もしくは無置換のクオーターフェニレン基、及び
    置換もしくは無置換のナフチレン基からなる群から選択される基である、請求項１又は２に記載の有機エレクトロルミネッセンス素子。     L 11 to L 13 in the formula (1) are each independently a single bond, or a substituted or unsubstituted phenylene group,
    A substituted or unsubstituted biphenylene group,
    A substituted or unsubstituted terphenylene group,
    The organic electroluminescence device according to claim 1, which is a group selected from the group consisting of a substituted or unsubstituted quarterphenylene group and a substituted or unsubstituted naphthylene group.
  4. 　前記式（１）におけるＡｒ１１～Ａｒ１３が、それぞれ独立に、置換もしくは無置換の環形成炭素数６～３０のアリール基である、請求項１～３のいずれかに記載の有機エレクトロルミネッセンス素子。 4. The organic electroluminescence device according to claim 1, wherein Ar 11 to Ar 13 in the formula (1) are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. ..
  5. 　前記式（１）におけるＡｒ１１～Ａｒ１３が、それぞれ独立に、
    置換もしくは無置換のフェニル基、
    置換もしくは無置換のナフチル基、
    置換もしくは無置換のフルオレニル基、
    置換もしくは無置換の９，９’－スピロビフルオレニル基、
    置換もしくは無置換のベンゾフルオレニル基、
    置換もしくは無置換のフェナントリル基、及び
    置換もしくは無置換のベンゾフェナントリル基からなる群から選択される、請求項１～４のいずれかに記載の有機エレクトロルミネッセンス素子。     Ar 11 to Ar 13 in the formula (1) are each independently
    A substituted or unsubstituted phenyl group,
    A substituted or unsubstituted naphthyl group,
    A substituted or unsubstituted fluorenyl group,
    A substituted or unsubstituted 9,9′-spirobifluorenyl group,
    A substituted or unsubstituted benzofluorenyl group,
    The organic electroluminescence device according to claim 1, which is selected from the group consisting of a substituted or unsubstituted phenanthryl group and a substituted or unsubstituted benzophenanthryl group.
  6. 　前記式（１）におけるＡｒ１１～Ａｒ１３のうちの１個以上が、それぞれ独立に、置換もしくは無置換の環形成原子数５～３０の１価の複素環基である、請求項１～３のいずれかに記載の有機エレクトロルミネッセンス素子。 The one or more of Ar 11 to Ar 13 in the formula (1) are each independently a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms. 5. The organic electroluminescence device according to any one of 1.
  7. 　前記式（１）で表される化合物が、下記式（１－１）で表される化合物である、請求項１～６のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000004
     ［式（１－１）中、Ｌ１１～Ｌ１３、Ａｒ１１～Ａｒ１３、Ｒ１、Ｒ３～Ｒ８は、前記式（１）で定義したとおりである。］     7. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1).
    Figure JPOXMLDOC01-appb-C000004
     [In the formula (1-1), L 11 to L 13 , Ar 11 to Ar 13 , R 1 , and R 3 to R 8 are as defined in the above formula (1). ]
  8. 　前記式（１）で表される化合物が、下記式（１－１Ｈ）で表される化合物である、請求項１～７のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000005
     ［式（１－１Ｈ）中、Ｌ１１～Ｌ１３及びＡｒ１１～Ａｒ１３は、前記式（１）で定義したとおりである。］     8. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1H).
    Figure JPOXMLDOC01-appb-C000005
     [In the formula (1-1H), L 11 to L 13 and Ar 11 to Ar 13 are as defined in the formula (1). ]
  9. 　前記式（１）における－Ｌ１３－Ａｒ１３で表される基が、
    置換もしくは無置換のフェニル基、
    置換もしくは無置換のナフチル基、
    置換もしくは無置換のビフェニル基、
    置換もしくは無置換のフェナントレニル基、
    置換もしくは無置換のベンゾフェナントレニル基、
    置換もしくは無置換のフルオレニル基、
    置換もしくは無置換のベンゾフルオレニル基、
    置換もしくは無置換のジベンゾフラニル基、
    置換もしくは無置換のナフトベンゾフラニル基、
    置換もしくは無置換のジベンゾチオフェニル基、及び
    置換もしくは無置換のカルバゾリル基からなる群から選択される、請求項１～３、７及び８のいずれかに記載の有機エレクトロルミネッセンス素子。     The group represented by —L 13 —Ar 13 in the above formula (1) is
    A substituted or unsubstituted phenyl group,
    A substituted or unsubstituted naphthyl group,
    A substituted or unsubstituted biphenyl group,
    A substituted or unsubstituted phenanthrenyl group,
    A substituted or unsubstituted benzophenanthrenyl group,
    A substituted or unsubstituted fluorenyl group,
    A substituted or unsubstituted benzofluorenyl group,
    A substituted or unsubstituted dibenzofuranyl group,
    A substituted or unsubstituted naphthobenzofuranyl group,
    The organic electroluminescent device according to any one of claims 1 to 3, 7 and 8, which is selected from the group consisting of a substituted or unsubstituted dibenzothiophenyl group and a substituted or unsubstituted carbazolyl group.
  10. 　前記式（１）で表される化合物が、下記式（１－２）～（１－４）で表される化合物からなる群から選択される、請求項１～７のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000006
     ［式（１－２）～（１－４）中、Ｌ１１、Ｌ１２、Ａｒ１１、Ａｒ１２、Ｒ１、Ｒ３～Ｒ８は、前記式（１）で定義したとおりである。］     8. The organic compound according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (1-2) to (1-4). Electroluminescent device.
    Figure JPOXMLDOC01-appb-C000006
     [In the formulas (1-2) to (1-4), L 11 , L 12 , Ar 11 , Ar 12 , R 1 and R 3 to R 8 are as defined in the formula (1). ]
  11. 　前記式（１）における－Ｌ１３－Ａｒ１３ではないＲ１～Ｒ８が、水素原子である、請求項１～１０のいずれかに記載の有機エレクトロルミネッセンス素子。 11. The organic electroluminescent device according to claim 1, wherein R 1 to R 8 other than —L 13 —Ar 13 in the formula (1) are hydrogen atoms.
  12. 　前記化合物Ａが、下記式（１３）、式（１４）又は式（１５）で表される化合物である請求項１～１１のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000007
     （式（１３）、式（１４）及び式（１５）中、
    　環Ａ’は、置換もしくは無置換の環形成炭素数１０～５０の縮合アリール環、又は置換もしくは無置換の環形成原子数８～５０の縮合複素環である。
    　Ｒ１０１～Ｒ１０７及びＲ１１０～Ｒ１１７は、前記式（１１－１）、前記式（１１－２）、前記式（１１－３）及び前記式（Ｘ）で定義したとおりである。）     The organic electroluminescent device according to any one of claims 1 to 11, wherein the compound A is a compound represented by the following formula (13), formula (14) or formula (15).
    Figure JPOXMLDOC01-appb-C000007
     (In Formula (13), Formula (14), and Formula (15),
    Ring A′ is a substituted or unsubstituted fused aryl ring having 10 to 50 ring-forming carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring-forming atoms.
    R 101 to R 107 and R 110 to R 117 are as defined in the formula (11-1), the formula (11-2), the formula (11-3) and the formula (X). )
  13. 　前記化合物Ａが、下記式（１６－１）～式（１６－５）で表される化合物からなる群から選択される化合物である、請求項１～１１のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000008
     （前記式（１６－１）～（１６－５）中、
    　Ｒ１０１～Ｒ１１７は、前記式（１１－１）、前記式（１１－２）、前記式（１１－３）及び前記式（Ｘ）で定義したとおりである。
    　Ｘは、Ｏ、ＮＲ１２５、又はＣ（Ｒ１２６）（Ｒ１２７）である。
    　Ｒ１２１～Ｒ１２７のうち隣接する２つ以上の１組以上は、置換もしくは無置換の飽和又は不飽和の環を形成するか、あるいは前記環を形成しない。
    　前記環を形成しないＲ１２１～Ｒ１２７は、それぞれ独立に、
    水素原子、ハロゲン原子、シアノ基、ニトロ基、ハロアルキル基、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の炭素数２～５０のアルケニル基、
    置換もしくは無置換の炭素数２～５０のアルキニル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の炭素数７～５０のアラルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    －Ｃ（＝Ｏ）（Ｒ９０８）、
    －ＣＯＯ（Ｒ９０９）、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０９は、前記式前記式（１１－１）～（１１－３）で定義したとおりである。）     12. The organic electroluminescence device according to claim 1, wherein the compound A is a compound selected from the group consisting of compounds represented by the following formulas (16-1) to (16-5). .
    Figure JPOXMLDOC01-appb-C000008
     (In the above formulas (16-1) to (16-5),
    R 101 to R 117 are as defined in the formula (11-1), the formula (11-2), the formula (11-3) and the formula (X).
    X is O, NR 125 , or C(R 126 )(R 127 ).
    One or more adjacent two or more sets of R 121 to R 127 form a substituted or unsubstituted saturated or unsaturated ring, or do not form the ring.
    R 121 to R 127 which do not form a ring are each independently
    Hydrogen atom, halogen atom, cyano group, nitro group, haloalkyl group,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    -C(=O)(R 908 ),
    -COO (R 909 ),
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    R 901 to R 909 are as defined in the above formulas (11-1) to (11-3). )
  14. 　前記化合物Ａが、前記式（１３）で表される化合物である、請求項１２に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 12, wherein the compound A is a compound represented by the formula (13).
  15. 　前記式（１３）のＲ１０５及びＲ１１４はそれぞれ独立に、－Ｎ（Ｒ９０６）（Ｒ９０７）（Ｒ９０６及びＲ９０７は、前記式（１）で定義したとおりである。）である、請求項１４に記載の有機エレクトロルミネッセンス素子。 R 105 and R 114 in the formula (13) are each independently —N(R 906 )(R 907 )(R 906 and R 907 are as defined in the formula (1)). The organic electroluminescent element according to claim 14.
  16. 　前記有機層が、発光層を含み、
    　前記発光層が、前記式（１）で表される化合物、及び前記化合物Ａを含む、請求項１～１５のいずれかに記載の有機エレクトロルミネッセンス素子。     The organic layer includes a light emitting layer,
    The organic electroluminescence device according to claim 1, wherein the light emitting layer contains the compound represented by the formula (1) and the compound A.
  17. 　前記有機層が、さらに、前記発光層に隣接する正孔阻止層を含み、
    　前記正孔阻止層が、下記式（２１）で表される化合物を含む、請求項１６に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000009
     ［式（２１）中、
    　Ｘ１～Ｘ３は、それぞれ独立に、Ｎ又はＣＲｂである。但し、Ｘ１～Ｘ３のうちの１個以上はＮである。
    　Ｒｂは、
    水素原子、
    ハロゲン原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒｂが２個存在する場合、２個のＲｂは、互いに同一であってもよいし、異なっていてもよい。Ｒｂは、隣接するＲ２１～Ｒ２３と結合して環を形成しない。
    　Ｒ２１～Ｒ２３は、それぞれ独立に、
    －（Ｌ２）ｍ－（Ａｒ２）ｎ、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の炭素数２～５０のアルケニル基、
    置換もしくは無置換の炭素数２～５０のアルキニル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
    　Ｌ２は、
    置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
    置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
    　ｍは、０～２の整数である。ｍが０のとき、Ｌ２は単結合である。ｍが２のとき、２個のＬ２は互いに同一であってもよいし、異なっていてもよい。
    　Ａｒ２は、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
    　ｎは、１又は２の整数であり、ｎが２のとき、２個のＡｒ２は、互いに同一であってもよいし、異なっていてもよい。但し、ｎが２のとき、ｍは１以上である。］     The organic layer further comprises a hole blocking layer adjacent to the light emitting layer,
    The organic electroluminescence device according to claim 16, wherein the hole blocking layer contains a compound represented by the following formula (21).
    Figure JPOXMLDOC01-appb-C000009
     [In Formula (21),
    X 1 to X 3 are each independently N or CR b . However, at least one of X 1 to X 3 is N.
    R b is
    Hydrogen atom,
    Halogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    When two R b 's are present, the two R b 's may be the same or different from each other. R b does not form a ring by combining with R 21 to R 23 which are adjacent to each other.
    R 21 to R 23 are each independently
    -(L 2 ) m -(Ar 2 ) n ,
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
    L 2 is
    A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
    m is an integer of 0 to 2. When m is 0, L 2 is a single bond. When m is 2, two L 2's may be the same or different.
    Ar 2 is
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
    n is an integer of 1 or 2, and when n is 2, two Ar 2 may be the same or different from each other. However, when n is 2, m is 1 or more. ]
  18. 　前記式（２１）におけるＸ１～Ｘ３のうちの２個が、Ｎである、請求項１７に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to claim 17, wherein two of X 1 to X 3 in the formula (21) are N.
  19. 　前記式（２１）におけるＲ２１～Ｒ２３が、それぞれ独立に、
    置換もしくは無置換の環形成炭素数６～５０のアリール基である、請求項１７又は１８に記載の有機エレクトロルミネッセンス素子。     R 21 to R 23 in the formula (21) are each independently
    19. The organic electroluminescence device according to claim 17, which is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  20. 　前記式（２１）で表される化合物が、下記式（２１－１）で表される化合物である、請求項１７又は１８に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000010
     ［式（２１－１）中、Ｒ２１、Ｒ２２及びＸ３は、前記式（２１）で定義したとおりである。
    　隣接するＲ５１～Ｒ５５の２個以上の１組以上が互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　前記環を形成しないＲ５１～Ｒ５５は、それぞれ独立に、
    水素原子、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、又は
    無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］     19. The organic electroluminescent device according to claim 17, wherein the compound represented by the formula (21) is a compound represented by the following formula (21-1).
    Figure JPOXMLDOC01-appb-C000010
     [In the formula (21-1), R 21 , R 22 and X 3 are as defined in the formula (21).
    Two or more adjacent groups of R 51 to R 55 are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or Do not form.
    R 51 to R 55 which do not form a ring are each independently
    Hydrogen atom,
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  21. 　前記式（２１－１）で表される化合物が、下記式（２１－２）で表される化合物である、請求項２０に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000011
     ［式（２１－２）中、Ｒ２２、Ｘ３及びＲ５１～Ｒ５５は、前記式（２１－１）で定義したとおりである。
    　Ｒ５６～Ｒ６０は、それぞれ独立に、
    水素原子、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、又は
    無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］     The organic electroluminescence device according to claim 20, wherein the compound represented by the formula (21-1) is a compound represented by the following formula (21-2).
    Figure JPOXMLDOC01-appb-C000011
     [In the formula (21-2), R 22 , X 3 and R 51 to R 55 are as defined in the above formula (21-1).
    R 56 to R 60 are each independently
    Hydrogen atom,
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  22. 　前記式（２１－２）で表される化合物が、下記式（２１－３）で表される化合物である、請求項２１に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000012
     ［式（２１－３）中、Ｒ２２、Ｘ３及びＲ５６～Ｒ６０は、前記式（２１－２）で定義したとおりである。
    　Ｙ１ａ～Ｙ８ａは、それぞれ独立に、ＣＲ６１ａ又はＮである。
    　Ｙ１ｂ～Ｙ８ｂは、それぞれ独立に、ＣＲ６１ｂ又はＮである。
    　Ｘ４ａは、Ｏ、Ｓ又はＮＲ６１ａである。
    　Ｘ４ｂは、Ｏ、Ｓ又はＮＲ６１ｂである。
    　隣接する原子に置換するＲ６１ａの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　隣接する原子に置換するＲ６１ｂの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　但し、Ｒ６１ａの１つが＊１と結合する単結合であるか、又は前記隣接する原子に置換するＲ６１ａの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介して＊１と結合する。
    　Ｒ６１ｂの１つが＊２と結合する単結合であるか、又は前記隣接する原子に置換するＲ６１ｂの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介して＊２と結合する。
    　前記環を形成せず、かつ、＊１又は＊２と結合する単結合ではないＲ６１ａ及びＲ６１ｂは、それぞれ独立に、
    水素原子、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、又は
    無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
    　Ｒ６１ａが複数存在する場合、複数のＲ６１ａは、互いに同一であってもよいし、異なっていてもよい。
    　Ｒ６１ｂが複数存在する場合、複数のＲ６１ｂは、互いに同一であってもよいし、異なっていてもよい。］     22. The organic electroluminescent device according to claim 21, wherein the compound represented by the formula (21-2) is a compound represented by the following formula (21-3).
    Figure JPOXMLDOC01-appb-C000012
     [In the formula (21-3), R 22 , X 3 and R 56 to R 60 are as defined in the formula (21-2).
    Y 1a to Y 8a are each independently CR 61a or N.
    Y 1b to Y 8b are each independently CR 61b or N.
    X 4a is O, S or NR 61a .
    X 4b is O, S or NR 61b .
    Two or more sets of two or more R 61a substituting adjacent atoms are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring-forming atoms, or Does not form a ring.
    Two or more sets of two or more R 61b substituting adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or Does not form a ring.
    However, one of R 61a is a single bond which is bonded to *1, or two or more one or more groups of R 61a substituting the adjacent atoms are bonded to each other to form a ring-forming atom. One binds to *1 via a single bond.
    One of R 61b is a single bond that is bonded to *2, or one of the atoms constituting the ring formed by two or more sets of two or more R 61b substituting the adjacent atoms is bonded to each other; , And to *2 via a single bond.
    R 61a and R 61b which do not form the ring and which are not a single bond that binds to *1 or *2 are each independently,
    Hydrogen atom,
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
    If R 61a there are a plurality, a plurality of R 61a may be the same or may be different from one another.
    If R 61b there are a plurality, the plurality of R 61b may be the same or may be different from one another. ]
  23. 　前記式（２１）で表される化合物が、下記式（２１－４）で表される化合物である、請求項１７に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000013
     ［式（２１－４）中、Ｘ１～Ｘ３、Ｒ２１、Ｒ２２、Ｌ２、ｍ及びｎは、前記式（２１）で定義したとおりである。
    　Ｙ１～Ｙ８は、それぞれ独立に、ＣＲ６１ｅ又はＮである。
    　Ｘ４は、Ｏ、Ｓ又はＮＲ６１ｅである。
    　隣接する原子に置換するＲ６１ｅの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　但し、Ｒ６１ｅの１つが＊３と結合する単結合であるか、又は前記隣接する原子に置換するＲ６１ｅの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、単結合を介して＊３と結合する。
    　前記環を形成せず、かつ、＊３と結合する単結合ではないＲ６１ｅは、それぞれ独立に、
    水素原子、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、又は
    無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
    　Ｒ６１ｅが複数存在する場合、複数のＲ６１ｅは、互いに同一であってもよいし、異なっていてもよい。］     The organic electroluminescence device according to claim 17, wherein the compound represented by the formula (21) is a compound represented by the following formula (21-4).
    Figure JPOXMLDOC01-appb-C000013
     [In the formula (21-4), X 1 to X 3 , R 21 , R 22 , L 2 , m and n are as defined in the formula (21).
    Y 1 to Y 8 are each independently CR 61e or N.
    X 4 is O, S or NR 61e .
    Two or more sets of two or more R 61e substituting adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms, or Does not form a ring.
    However, one of R 61e is a single bond that is bonded to *3, or one or more groups of two or more of R 61e substituting the adjacent atoms are bonded to each other to form a ring. One binds to *3 via a single bond.
    R 61e , which does not form the ring and is not a single bond that binds to *3, independently represents
    Hydrogen atom,
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
    If R 61e there are a plurality, the plurality of R 61e may be the same or may be different from one another. ]
  24. 　前記有機層が、さらに前記発光層に隣接する電子阻止層を含み、
    　前記電子阻止層が、下記式（４１）で表される化合物、又は下記式（５１）で表される化合物を含む、請求項１６～２３のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000014
     ［式（４１）中、
    　Ｌ４１～Ｌ４３は、それぞれ独立に、
    単結合、
    置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
    置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
    　Ａｒ４１～Ａｒ４３は、それぞれ独立に、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。］
    Figure JPOXMLDOC01-appb-C000015
     ［式（５１）中、
    　隣接する原子に置換するＲ６２～Ｒ７０の２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　隣接する原子に置換するＲ７１～Ｒ７９の２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　但し、Ｒ６２～Ｒ７０のうちの１つが＊４と結合する単結合であるか、又は前記隣接する原子に置換するＲ６２～Ｒ７０の２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、＊４と単結合を介して結合する。
    　Ｒ７１～Ｒ７９のうちの１つが＊５と結合する単結合であるか、又は前記隣接する原子に置換するＲ７１～Ｒ７９の２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、＊５と単結合を介して結合する。また、＊５と結合しないＲ７１～Ｒ７９のうちの１つがＬ５２と結合する単結合であるか、又は前記隣接する原子に置換するＲ７１～Ｒ７９の２個以上の１組以上が互いに結合して形成された環を構成する原子のうちの他の１つが、Ｌ５２と単結合を介して結合する。
    　前記環を形成せず、かつ、＊４又は＊５と結合する単結合ではないＲ６２～Ｒ７９は、それぞれ独立に、
    水素原子、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、又は
    無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。
    　Ｌ５１は、それぞれ独立に、
    置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
    置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
    　ｑは、０～３の整数である。ｑが２以上のとき、２以上存在するＲ６２～Ｒ７０は互いに同一であってもよいし、異なっていてもよい。但し、ｑが０のときはＬ５１を終端する水素原子である。
    　ｒは０～２の整数である。ｒが０のとき、Ｌ５１は単結合である。ｒが２のとき、２個のＬ５１は、互いに同一であってもよいし、異なっていてもよい。但し、ｑが２以上のとき、ｒは１又は２である。
    　Ｌ５２は、
    単結合、
    置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
    置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
    　Ａｒ５２は、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。］     The organic layer further includes an electron blocking layer adjacent to the light emitting layer,
    24. The organic electroluminescence device according to claim 16, wherein the electron blocking layer contains a compound represented by the following formula (41) or a compound represented by the following formula (51).
    Figure JPOXMLDOC01-appb-C000014
     [In Formula (41),
    L 41 to L 43 are each independently
    Single bond,
    A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
    Ar 41 to Ar 43 are each independently
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. ]
    Figure JPOXMLDOC01-appb-C000015
     [In formula (51),
    At least one pair of two or more of R 62 to R 70 substituting adjacent atoms is bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring having 3 to 30 ring-forming atoms; , Or does not form the ring.
    Two or more sets of two or more of R 71 to R 79 which are substituted on adjacent atoms are bonded to each other to form a saturated or unsaturated ring having 3 to 30 substituted or unsubstituted ring-forming atoms. , Or does not form the ring.
    Provided that one of R 62 to R 70 is a single bond that bonds to *4, or two or more pairs of R 62 to R 70 which substitute the adjacent atom are bonded to each other. One of the atoms constituting the ring formed is bonded to *4 via a single bond.
    One of R 71 to R 79 is a single bond that binds to *5, or two or more pairs of R 71 to R 79 which substitute the adjacent atom are formed by bonding to each other; One of the atoms constituting the ring is bonded to *5 via a single bond. In addition, one of R 71 to R 79 that does not bond to *5 is a single bond that bonds to L 52 , or one or more pairs of two or more of R 71 to R 79 that substitute for the adjacent atom are Another one of the atoms constituting the ring formed by bonding to each other is bonded to L 52 via a single bond.
    R 62 to R 79 which do not form a ring and which are not a single bond to bond with *4 or *5 are each independently
    Hydrogen atom,
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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.
    L 51 is, independently of each other,
    A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
    q is an integer of 0 to 3. When q is 2 or more, R 62 to R 70 existing in two or more may be the same or different from each other. However, when q is 0, it is a hydrogen atom terminating L 51 .
    r is an integer of 0 to 2. When r is 0, L 51 is a single bond. When r is 2, two L 51 's may be the same or different from each other. However, when q is 2 or more, r is 1 or 2.
    L 52 is
    Single bond,
    A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
    Ar 52 is
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. ]
  25. 　前記式（４１）で表される化合物が、下記式（４１－１）で表される化合物である、請求項２４に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000016
     ［式（４１－１）中、Ａｒ４１～Ａｒ４３及びＬ４１は、前記式（４１）で定義したとおりである。］     The organic electroluminescence device according to claim 24, wherein the compound represented by the formula (41) is a compound represented by the following formula (41-1).
    Figure JPOXMLDOC01-appb-C000016
     [In the formula (41-1), Ar 41 to Ar 43 and L 41 are as defined in the formula (41). ]
  26. 　前記式（４１）で表される化合物が、下記式（４１－２）で表される化合物である、請求項２４又は２５に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000017
     ［式（４１－２）中、Ａｒ４１及びＬ４１は、前記式（４１）で定義したとおりである。
    　Ｘ５及びＸ６は、それぞれ独立に、Ｏ、Ｓ又はＮ（Ｒ９０６）である。
    　Ｒ９０６は、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０６が２個存在する場合、２個のＲ９０６はそれぞれは同一でもよく、異なっていてもよい。］     The organic electroluminescent device according to claim 24 or 25, wherein the compound represented by the formula (41) is a compound represented by the following formula (41-2).
    Figure JPOXMLDOC01-appb-C000017
     [In the formula (41-2), Ar 41 and L 41 are as defined in the above formula (41).
    X 5 and X 6 are each independently O, S or N(R 906 ).
    R 906 is
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms. When two R 906 are present, the two R 906 may be the same or different. ]
  27. 　前記式（４１）で表される化合物が、下記式（４１－３）で表される化合物である、請求項２４に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000018
     ［式（４１－３）中、Ａｒ４１、Ａｒ４２及びＬ４１～Ｌ４３は、前記式（４１）で定義したとおりである。
    　Ｘ７は、Ｏ、Ｓ又はＮＲ８９である。
    　隣接する原子に置換するＲ８１～Ｒ８９のうちの２個以上の１組以上は、互いに結合して、置換もしくは無置換の環形成原子数３～３０の、飽和もしくは不飽和の環を形成するか、あるいは前記環を形成しない。
    　但し、Ｒ８１～Ｒ８９の１つが＊６と結合する単結合であるか、又は前記隣接する原子に置換するＲ８１～Ｒ８９のうちの２個以上の１組以上が互いに結合して形成された環を構成する原子の１つが、＊６と単結合を介して結合する。
    　前記環を形成せず、かつ、＊６と結合する単結合ではないＲ８１～Ｒ８９は、それぞれ独立に、
    水素原子、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、又は
    無置換の環形成原子数５～５０の１価の複素環基である。
    　Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。］     The organic electroluminescence device according to claim 24, wherein the compound represented by the formula (41) is a compound represented by the following formula (41-3).
    Figure JPOXMLDOC01-appb-C000018
     [In the formula (41-3), Ar 41 , Ar 42, and L 41 to L 43 are as defined in the formula (41).
    X 7 is O, S or NR 89 .
    Two or more sets of two or more of R 81 to R 89 which substitute the adjacent atom are bonded to each other to form a substituted or unsubstituted ring-forming saturated or unsaturated ring having 3 to 30 ring-forming atoms. Or does not form the ring.
    Provided that one of R 81 to R 89 is a single bond that bonds to *6, or two or more sets of R 81 to R 89 which substitute the adjacent atoms are bonded to each other. One of the atoms constituting the ring formed is bonded to *6 via a single bond.
    R 81 to R 89 , which do not form a ring and are not a single bond that binds to *6, are each independently
    Hydrogen atom,
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 ),
    Halogen atom, cyano group, nitro group,
    It is an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ]
  28. 　前記式（５１）で表される化合物が、下記式（５１－１）で表される化合物である、請求項２４に記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000019
     ［式（５１－１）中、Ｒ６２～Ｒ７０、Ｒ７２～Ｒ７９、＊４、＊５、ｑ、Ｌ５１、ｒ、Ｌ５２及びＡｒ５２は、前記式（５１）で定義したとおりである。］     The organic electroluminescence device according to claim 24, wherein the compound represented by the formula (51) is a compound represented by the following formula (51-1).
    Figure JPOXMLDOC01-appb-C000019
     [In the formula (51-1), R 62 to R 70 , R 72 to R 79 , *4, *5, q, L 51 , r, L 52, and Ar 52 are as defined in the formula (51). Is. ]
  29. 　前記式（５１）におけるｑが１である、請求項２４又は２８に記載の有機エレクトロルミネッセンス素子。 29. The organic electroluminescent device according to claim 24 or 28, wherein q in the formula (51) is 1.
  30. 　前記式（５１）で表される化合物が、下記式（５１－２）で表される化合物である、請求項２４、２８及び２９のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000020
     ［式（５１－２）中、Ｒ６２、Ｌ５１、ｒ、Ｌ５２及びＡｒ５２は、前記式（５１）で定義したとおりである。］     30. The organic electroluminescent device according to claim 24, wherein the compound represented by the formula (51) is a compound represented by the following formula (51-2).
    Figure JPOXMLDOC01-appb-C000020
     [In the formula (51-2), R 62 , L 51 , r, L 52, and Ar 52 are as defined in the formula (51). ]
  31. 　前記式（５１）で表される化合物が、下記式（５１－３ａ）～（５１－３ｃ）で表される化合物からなる群から選択される、請求項２４、及び２８～３０のいずれかに記載の有機エレクトロルミネッセンス素子。
    Figure JPOXMLDOC01-appb-C000021
     ［式（５１－３ａ）～（５１－３ｃ）中、Ｒ６２、Ｌ５１、ｒ、Ｌ５２及びＡｒ５２は、前記式（５１）で定義したとおりである。］     The compound according to any one of claims 24 and 28 to 30, wherein the compound represented by the formula (51) is selected from the group consisting of compounds represented by the following formulas (51-3a) to (51-3c). The organic electroluminescence device described.
    Figure JPOXMLDOC01-appb-C000021
     [In the formulas (51-3a) to (51-3c), R 62 , L 51 , r, L 52, and Ar 52 are as defined in the formula (51). ]
  32. 　前記「置換もしくは無置換の」という場合の置換基が、
    無置換の炭素数１～５０のアルキル基、
    無置換の炭素数２～５０のアルケニル基、
    無置換の炭素数２～５０のアルキニル基、
    無置換の環形成炭素数３～５０のシクロアルキル基、
    －Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
    －Ｏ－（Ｒ９０４）、
    －Ｓ－（Ｒ９０５）、
    －Ｎ（Ｒ９０６）（Ｒ９０７）
    （ここで、
    Ｒ９０１～Ｒ９０７は、それぞれ独立に、
    水素原子、
    置換もしくは無置換の炭素数１～５０のアルキル基、
    置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
    置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
    置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ９０１～Ｒ９０７が２個以上存在する場合、２個以上のＲ９０１～Ｒ９０７のそれぞれは同一でもよく、異なっていてもよい。）、
    ハロゲン原子、シアノ基、ニトロ基、
    無置換の環形成炭素数６～５０のアリール基、及び
    無置換の環形成原子数５～５０の１価の複素環基
    からなる群から選択される基である、請求項１～３１のいずれかに記載の有機エレクトロルミネッセンス素子。     The substituent in the case of “substituted or unsubstituted” is
    An unsubstituted alkyl group having 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,
    An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    -Si(R 901 )(R 902 )(R 903 ),
    -O-( R904 ),
    -S- (R 905 ),
    -N(R 906 )(R 907 )
    (here,
    R 901 to R 907 are each independently
    Hydrogen atom,
    A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
    A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
    It is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming 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. ),
    Halogen atom, cyano group, nitro group,
    Any of claims 1 to 31, which is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. The organic electroluminescence device according to Crab.
  33. 　前記「置換もしくは無置換の」という場合の置換基が、
    炭素数１～５０のアルキル基、
    環形成炭素数６～５０のアリール基、及び
    環形成原子数５～５０の１価の複素環基
    からなる群から選択される基である、請求項１～３２のいずれかに記載の有機エレクトロルミネッセンス素子。     The substituent in the case of “substituted or unsubstituted” is
    An alkyl group having 1 to 50 carbon atoms,
    33. The organic electro according to claim 1, which is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms. Luminescence element.
  34. 　前記「置換もしくは無置換の」という場合の置換基が、
    炭素数１～１８のアルキル基、
    環形成炭素数６～１８のアリール基、及び
    環形成原子数５～１８の１価の複素環基
    からなる群から選択される基である、請求項１～３３のいずれかに記載の有機エレクトロルミネッセンス素子。     The substituent in the case of “substituted or unsubstituted” is
    An alkyl group having 1 to 18 carbon atoms,
    The organic electro according to any one of claims 1 to 33, which is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms. Luminescence element.
  35. 　請求項１～３４のいずれかに記載の有機エレクトロルミネッセンス素子を備える電子機器。 An electronic device comprising the organic electroluminescent element according to any one of claims 1 to 34.
PCT/JP2019/047626 2018-12-05 2019-12-05 Organic electroluminescence element and electronic device WO2020116562A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2018-228533 2018-12-05
JP2018228533 2018-12-05
JP2019093821 2019-05-17
JP2019-093821 2019-05-17

Publications (1)

Publication Number Publication Date
WO2020116562A1 true WO2020116562A1 (en) 2020-06-11

Family

ID=70974691

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/047626 WO2020116562A1 (en) 2018-12-05 2019-12-05 Organic electroluminescence element and electronic device

Country Status (1)

Country Link
WO (1) WO2020116562A1 (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113372261A (en) * 2021-07-14 2021-09-10 中国科学院兰州化学物理研究所 Method for preparing 1-bromine/chlorocarbazole and derivatives thereof
WO2022097574A1 (en) * 2020-11-06 2022-05-12 保土谷化学工業株式会社 Organic electroluminescent element
WO2022154029A1 (en) * 2021-01-13 2022-07-21 出光興産株式会社 Organic electroluminescent element, organic electroluminescent display device, and electronic device
WO2022154030A1 (en) * 2021-01-13 2022-07-21 出光興産株式会社 Organic electroluminescent element, organic electroluminescent display apparatus, and digital device
US11548877B2 (en) 2018-11-30 2023-01-10 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
US11618740B2 (en) 2019-03-15 2023-04-04 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence devices, organic electroluminescence device, and electronic device
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
WO2024050708A1 (en) * 2022-09-07 2024-03-14 北京大学深圳研究生院 Blue light emitting guest material and use

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170116983A (en) * 2016-04-12 2017-10-20 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same
CN108084197A (en) * 2017-12-26 2018-05-29 长春海谱润斯科技有限公司 A kind of bis-carbazole derivative and its organic luminescent device
CN108084195A (en) * 2017-12-26 2018-05-29 长春海谱润斯科技有限公司 A kind of bis-carbazole fused ring compound and its organic luminescent device
KR20180097955A (en) * 2017-02-24 2018-09-03 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
WO2018186404A1 (en) * 2017-04-03 2018-10-11 出光興産株式会社 Organic electroluminescent element and electronic device
WO2019111971A1 (en) * 2017-12-06 2019-06-13 出光興産株式会社 Organic electroluminescent element and novel compound

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170116983A (en) * 2016-04-12 2017-10-20 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same
KR20180097955A (en) * 2017-02-24 2018-09-03 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
WO2018186404A1 (en) * 2017-04-03 2018-10-11 出光興産株式会社 Organic electroluminescent element and electronic device
WO2019111971A1 (en) * 2017-12-06 2019-06-13 出光興産株式会社 Organic electroluminescent element and novel compound
CN108084197A (en) * 2017-12-26 2018-05-29 长春海谱润斯科技有限公司 A kind of bis-carbazole derivative and its organic luminescent device
CN108084195A (en) * 2017-12-26 2018-05-29 长春海谱润斯科技有限公司 A kind of bis-carbazole fused ring compound and its organic luminescent device

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11548877B2 (en) 2018-11-30 2023-01-10 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
US11618740B2 (en) 2019-03-15 2023-04-04 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence devices, organic electroluminescence device, and electronic device
US11744149B2 (en) 2019-05-31 2023-08-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US12048242B2 (en) 2019-05-31 2024-07-23 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
WO2022097574A1 (en) * 2020-11-06 2022-05-12 保土谷化学工業株式会社 Organic electroluminescent element
WO2022154029A1 (en) * 2021-01-13 2022-07-21 出光興産株式会社 Organic electroluminescent element, organic electroluminescent display device, and electronic device
WO2022154030A1 (en) * 2021-01-13 2022-07-21 出光興産株式会社 Organic electroluminescent element, organic electroluminescent display apparatus, and digital device
CN113372261A (en) * 2021-07-14 2021-09-10 中国科学院兰州化学物理研究所 Method for preparing 1-bromine/chlorocarbazole and derivatives thereof
WO2024050708A1 (en) * 2022-09-07 2024-03-14 北京大学深圳研究生院 Blue light emitting guest material and use

Similar Documents

Publication Publication Date Title
WO2020071478A1 (en) Novel compound and organic electroluminescent element material containing same
WO2020116562A1 (en) Organic electroluminescence element and electronic device
WO2019240251A1 (en) Organic electroluminescent element and electronic equipment using same
WO2020067290A1 (en) Novel compound and organic electroluminescence device
WO2020075784A1 (en) Organic electroluminescent element and electronic device using same
WO2020036197A1 (en) Organic electroluminescent element and electronic device using same
KR20200139684A (en) Organic electroluminescence device and electronic device
WO2020075769A1 (en) Organic electroluminescent element and electronic device using same
WO2021025162A1 (en) Novel compound, organic electroluminescent element including same, and electronic appliance
WO2020250961A1 (en) Organic electroluminescent element and electronic device using same
WO2020096012A1 (en) Organic electroluminescent element and electronic appliance including same
JP7328358B2 (en) Organic electroluminescent elements, compositions, powders, electronic devices, and novel compounds
JP2020188121A (en) Organic electroluminescense device and electronic apparatus
WO2020116561A1 (en) Organic electroluminescence element and electronic apparatus
KR20230116812A (en) Compounds, organic electroluminescent devices and electronic devices
WO2020115933A1 (en) Organic electroluminescent element and electronic device using same
WO2020027323A1 (en) Organic electroluminescent element and electronic device
JP2021172592A (en) Compound and organic electroluminescent device
WO2022264826A1 (en) Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device
JP2023006698A (en) Compound, material for organic electroluminescent device, organic electroluminescent device, and electronic apparatus
WO2022215527A1 (en) Compound and organic electroluminescent element
WO2023112915A1 (en) Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device
WO2023017861A1 (en) Composition, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
US20230145611A1 (en) Compound and organic electroluminescent element
KR20240090597A (en) Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19891988

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19891988

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP