WO2020116562A1 - Élément électroluminescent organique et dispositif électronique - Google Patents

Élément électroluminescent organique et dispositif électronique Download PDF

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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
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group
ring
substituted
unsubstituted
carbon atoms
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Japanese (ja)
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聡美 田崎
太郎 八巻
竜志 前田
裕基 中野
裕亮 糸井
良多 高橋
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出光興産株式会社
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    • 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.

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

Abstract

L'invention concerne un élément électroluminescent organique présentant une électrode négative, une électrode positive et une couche organique entre l'électrode négative et l'électrode positive. La couche organique contient : un composé représenté par la formule (1) ; et un composé A qui est un composé représenté par les formules (11-1) et (11-3) ou un composé représenté par les formules (11-2) et (11-3).
PCT/JP2019/047626 2018-12-05 2019-12-05 Élément électroluminescent organique et dispositif électronique WO2020116562A1 (fr)

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Cited By (8)

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CN113372261A (zh) * 2021-07-14 2021-09-10 中国科学院兰州化学物理研究所 一种制备1-溴/氯咔唑及其衍生物的方法
WO2022097574A1 (fr) * 2020-11-06 2022-05-12 保土谷化学工業株式会社 Élément électroluminescent organique
WO2022154029A1 (fr) * 2021-01-13 2022-07-21 出光興産株式会社 Élément électroluminescent organique, dispositif d'affichage électroluminescent organique et dispositif électronique
WO2022154030A1 (fr) * 2021-01-13 2022-07-21 出光興産株式会社 Élément électroluminescent organique, appareil d'affichage électroluminescent organique et dispositif numérique
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 (fr) * 2022-09-07 2024-03-14 北京大学深圳研究生院 Matériau invité émettant de la lumière bleue et utilisation

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Cited By (8)

* 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
WO2022097574A1 (fr) * 2020-11-06 2022-05-12 保土谷化学工業株式会社 Élément électroluminescent organique
WO2022154029A1 (fr) * 2021-01-13 2022-07-21 出光興産株式会社 Élément électroluminescent organique, dispositif d'affichage électroluminescent organique et dispositif électronique
WO2022154030A1 (fr) * 2021-01-13 2022-07-21 出光興産株式会社 Élément électroluminescent organique, appareil d'affichage électroluminescent organique et dispositif numérique
CN113372261A (zh) * 2021-07-14 2021-09-10 中国科学院兰州化学物理研究所 一种制备1-溴/氯咔唑及其衍生物的方法
WO2024050708A1 (fr) * 2022-09-07 2024-03-14 北京大学深圳研究生院 Matériau invité émettant de la lumière bleue et utilisation

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