WO2020075758A1 - Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci - Google Patents

Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci Download PDF

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WO2020075758A1
WO2020075758A1 PCT/JP2019/039828 JP2019039828W WO2020075758A1 WO 2020075758 A1 WO2020075758 A1 WO 2020075758A1 JP 2019039828 W JP2019039828 W JP 2019039828W WO 2020075758 A1 WO2020075758 A1 WO 2020075758A1
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group
substituted
unsubstituted
ring
carbon atoms
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裕基 中野
太郎 八巻
聡美 田崎
加藤　朋希
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出光興産株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electroluminescence element and an electronic device using the same.
  • organic electroluminescence element (hereinafter, also referred to as “organic EL element”)
  • organic EL element When a voltage is applied to the organic electroluminescence element (hereinafter, also referred to as “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 a polycyclic aromatic compound in which a plurality of aromatic rings are connected by a boron atom and a nitrogen atom is used as a dopant material for a light emitting layer of an organic EL device, and a specific anthracene-based compound is used as a host material. It is disclosed.
  • An object of the present invention is to provide an organic EL device having excellent luminous efficiency and an electronic device using the organic EL device.
  • the compound (dopant) represented by the formula (1) and the compound (host material) having a specific structure represented by the formula (11) are combined to form a light emitting layer. It was found that an organic EL device exhibiting a high luminous efficiency can be obtained by using it for the above-mentioned, and the present invention has been completed.
  • the following organic EL device and electronic device are provided.
  • Ar 1 is bonded to either or both of R 3 and R 13 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • Ar 2 is bonded to either or both of R 5 and R 6 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • Ar 1 and Ar 2 that do not form a substituted or unsubstituted heterocycle are each independently It is an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
  • One or more adjacent two or more sets of R 1 to R 13 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 1 to R 13 which are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring 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-forming carbon atoms, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocycl
  • R 901 to R 905 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-forming carbon atoms, 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.
  • each of the two or more R 901 to R 905 may be the same or different.
  • 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 carbon atoms for ring formation, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), 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.
  • n and n are each independently R 1 and R, which are Ar 1 and Ar 2 and which can be substituted with an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms. It is a number of two .
  • R 1 's may be the same or different
  • n is 2 or more
  • two or more R 2 's may be the same. And may be different.
  • Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and composed of only a benzene ring.
  • L 101 and L 102 are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and composed only of a benzene ring.
  • the total number of benzene rings forming Ar 101 , L 101, and L 102 is 2 or more.
  • R 911 to R 913 are each independently an alkyl group having 1 to 50 carbon atoms. When two or more R 911 to R 913 are present, each of the two or more R 911 to R 913 may be the same or different.
  • R 101 to R 104 and two or more adjacent ones of R 105 to R 108 do not bond with each other to form a ring.
  • Two or more adjacent R 111 to R 117 do not bond to each other to form a ring.
  • R 101 to R 108 and R 111 to R 117 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-forming carbon atoms, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group,
  • R 901 to R 905 are as defined in the above formula (1).
  • R 906 and 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-forming carbon atoms, 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.
  • each of the two or more R 906 and R 907 may be the same or different.
  • FIG. 1 is a diagram illustrating a schematic configuration of an organic EL element according to one embodiment of the present invention.
  • hydroxide includes isotopes having different neutron numbers, that is, protium, deuterium, and tritium.
  • the number of ring-forming carbon atoms refers to the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). Indicates the number of carbon atoms among the atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring-forming carbons
  • a naphthalene ring has 10 ring-forming carbons
  • a pyridine ring has 5 ring-forming carbons
  • a furan ring has 4 ring-forming carbons.
  • the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms
  • the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
  • the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms.
  • the number of ring-forming atoms means a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a condensed ring, a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, Ring compound) represents the number of atoms constituting the ring itself.
  • the atoms that do not form a ring eg, hydrogen atoms that terminate the bonds of the atoms that make up the ring
  • the atoms that are included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring-forming atoms
  • the quinazoline ring has 10 ring-forming atoms
  • the furan ring has 5 ring-forming atoms.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is 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” represents the number of carbon atoms when the ZZ group is unsubstituted.
  • the carbon number of the substituent in the case where it is performed 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”, and “XX” and “YY” each mean an integer of 1 or more.
  • the ring-forming carbon number 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 herein is from 5 to 50, preferably from 5 to 30, more preferably from 5 to 18, unless otherwise specified herein. is there.
  • the carbon number of the “unsubstituted alkyl group” described in the present specification is 1 to 50, 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, more preferably 2 to 6, unless otherwise specified in the present specification.
  • the carbon number of the “unsubstituted alkynyl 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 number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this 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 carbon number of the “unsubstituted alkylene group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
  • Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described in the present specification 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 following “unsubstituted aryl group” has a substituent and examples of a substituted aryl group. .
  • the examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the “substituted aryl group” described in the present specification includes “unsubstituted aryl group”.
  • the group in which the “group” has a substituent further has a substituent
  • the “substituted aryl group” further has a substituent.
  • aryl group Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, a p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, Anthryl group, Benzoanthryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, A chrysenyl group, Benzochrysenyl group, Triphenylenyl group, Tripheny
  • 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, A cyanophenyl group, Triphenylsilylphenyl group, Trimethyls
  • 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.
  • an unsubstituted heterocyclic group refers to a case where “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”, and a substituted heterocyclic group refers to “substituted or unsubstituted heterocyclic group.”
  • heterocyclic group is a “substituted heterocyclic group”.
  • both “unsubstituted heterocyclic group” and “substituted heterocyclic group” are used.
  • the “substituted heterocyclic group” is a case where the “unsubstituted heterocyclic group” has a substituent, and the following “unsubstituted heterocyclic group” has a substituent or an example of a substituted heterocyclic group. And the like.
  • the examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” are merely examples, and the “substituted heterocyclic group” described in the present specification includes “unsubstituted heterocyclic group”.
  • 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 is also included.
  • Unsubstituted heterocyclic group containing oxygen atom Frill group, An oxazolyl group, Isoxazolyl group, An oxadiazolyl group, Xanthenyl group, Benzofuranyl group, An isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxazinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaphthobenzofuranyl group, Diazanaphthobenzofuranyl group, Diazanaphthobenzofuranyl group
  • Unsubstituted heterocyclic group containing a sulfur atom Thienyl group, Thiazolyl group, An isothiazolyl group, Thiadiazolyl group, Benzothiophenyl group, Isobenzothiophenyl group, Dibenzothiophenyl group, Naphthobenzothiophenyl group, Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, A dinaphthothiophenyl group, Azadibenzothiophenyl group, Diazadibenzothiophenyl group, Azanaphthobenzothiophenyl group, Diazanaphthobenzothiophenyl group
  • a 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, A phenylcarbazol-9-yl group, A methylbenzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, Biphenylylquinazolinyl group
  • a substituted heterocyclic group containing an oxygen atom Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, Monovalent residue of spiro [9H-xanthene-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 heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a bond at an arbitrary position to be a monovalent heterocyclic group.
  • the monovalent group derived from the unsubstituted heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a substituent when the carbon atom constituting the skeleton in these formulas is 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.
  • specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” described in the present specification include the following unsubstituted alkyl groups and substituted alkyl groups.
  • the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”
  • the substituted alkyl group refers to a “substituted or unsubstituted alkyl group”
  • the term “substituted alkyl group” is referred to.
  • the term “alkyl group” includes both “unsubstituted alkyl group” and “substituted alkyl group”.
  • the “substituted alkyl group” is a case where the “unsubstituted alkyl group” has a substituent, and examples thereof include a group in which the following “unsubstituted alkyl group” has a substituent and examples of a substituted alkyl group. .
  • the examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the “substituted alkyl group” described in this specification includes “unsubstituted alkyl group”.
  • the group in which the “group” has a substituent further has a substituent
  • the “substituted alkyl group” further has a substituent.
  • 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
  • specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” described in the present specification include the following unsubstituted alkenyl groups and substituted alkenyl groups.
  • the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group”
  • the “substituted alkenyl group” refers to a “substituted or unsubstituted alkenyl group.” Is a "substituted alkenyl group”.
  • alkenyl group 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 of the following ⁇ unsubstituted alkenyl group '' include a group having a substituent and a substituted alkenyl group. .
  • the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” are merely examples, and the “substituted alkenyl group” described in the present specification includes “unsubstituted alkenyl group”.
  • the group in which the “group” has a substituent further has a substituent
  • the “substituted alkenyl group” further has a substituent.
  • Unsubstituted alkenyl group and substituted alkenyl group Vinyl group, Allyl group, 1-butenyl group, 2-butenyl group, A 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1,2-dimethylallyl group
  • Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” described in the present specification 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 Alkynyl group "and” substituted alkynyl group ".
  • substituted alkynyl group is a case where the “unsubstituted alkynyl group” has a substituent, and examples thereof include the following “unsubstituted alkynyl group” having a substituent.
  • Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” 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 means a "substituted cycloalkyl group”.
  • Substituted cycloalkyl group is a case where "unsubstituted cycloalkyl group” has a substituent, and examples of the following "unsubstituted cycloalkyl group” have a substituent and substituted cycloalkyl groups. And the like. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” are merely examples, and the “substituted cycloalkyl group” described in this specification includes “unsubstituted cycloalkyl group”. A group in which the “substituted cycloalkyl group” further has a substituent, a group in which the “substituted cycloalkyl group” further has a substituent, and the like are also included.
  • Specific examples 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 the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G5 is the “alkynyl group” described in Specific Example Group G5.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • G8 Specific examples of the group represented by —O— (R 904 ) described in the present specification (specific example group G8) include -O (G1), -O (G2), -O (G3), -O (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • G9 Specific examples of the group represented by -S- (R 905 ) described in the present specification (specific example group G9) include -S (G1), -S (G2), -S (G3), -S (G6) Is mentioned.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • G1 is an "aryl group” described in Specific Example Group G1.
  • G2 is the “heterocyclic group” described in Specific Example Group G2.
  • G3 is the “alkyl group” described in Specific Example Group G3.
  • G6 is the “cycloalkyl group” described in Specific Example Group G6.
  • Specific examples (specific example group G11) of the “halogen atom” described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • a specific example of the “alkoxy group” described in the present specification is a group represented by —O (G3), where 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 this specification.
  • a specific example of the “alkylthio group” described in the present specification is a group represented by —S (G3), where 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 this specification.
  • a specific example of the “aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “aryl group” described in the specific example group G1.
  • the ring-forming carbon number of the “unsubstituted aryloxy group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the “arylthio group” described in the present specification is a group represented by —S (G1), where G1 is the “aryl group” described in the specific example group G1.
  • the ring-forming carbon number of the “unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the “aralkyl group” described in the present specification is a group represented by — (G3) — (G1), wherein G3 is an “alkyl group” described in the specific example group G3. , G1 is the “aryl group” described in Specific Example Group G1.
  • an “aralkyl group” is an embodiment of a “substituted alkyl group” substituted with an “aryl group”.
  • the carbon number of the “unsubstituted aralkyl group” which is the “unsubstituted alkyl group” substituted by 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, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group and the like.
  • the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , A pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluor
  • the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, unless otherwise specified in the present specification.
  • Nanthrolinyl 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) carbazolyl -1-yl group, (9-phenyl) carbazol-2-yl group, (9-phenyl) carbazol-3-yl group, or (9-phenyl) carbazol-4-yl group), (9-biphen
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any one of the following groups unless otherwise described in this specification.
  • 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. And the like.
  • 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 (specific group G12) of the "substituted or unsubstituted arylene group", a group excluding one hydrogen bonded to the ring-forming carbon of the "aryl group” described in the specific group G1. Is.
  • Specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” described in the present specification include groups obtained by divalently converting the “heterocyclic group” described in the specific example group G2. Is mentioned. That is, specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” include one of the “heterocyclic groups” bonded to the ring-forming atom of the “heterocyclic group” described in the specific example group G2. It is a group excluding hydrogen.
  • the substituted or unsubstituted arylene group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.
  • R 908 is a substituent.
  • m901 is 0 to a 4 integer, when m901 represents 2 or more, to R 908 of existing in plural numbers may be the same as each other or may be different.
  • R 909 is each independently 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 910 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 one of the following groups unless otherwise described in the present specification.
  • R 911 is a hydrogen atom or a substituent.
  • X B is an oxygen atom or a sulfur atom.
  • adjacent two which form a ring when one or more adjacent two or more are bonded to each other to form a ring includes 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 .
  • the “one or more sets” means that two or more adjacent two sets may form a ring at the same time.
  • R 921 and R 922 combine with each other to form ring A
  • R 925 and R 926 combine with each other to form ring B
  • the compound is represented by the following formula (XY-81) .
  • R 921 and R 922 combine with each other to form ring A
  • R 922 and R 923 combine with each other to form ring C
  • XY-82 In the case where three adjacent R 921 to R 923 are fused to the anthracene mother skeleton to form a ring A and a ring C sharing R 922 , they are represented by the following formula (XY-82).
  • the 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 heterocyclic ring.
  • “Saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.
  • a ring A formed by bonding R 921 and R 922 to each other has a carbon atom of an anthracene skeleton to which R 921 is bonded and a carbon atom of an anthracene skeleton to which R 922 is bonded.
  • a ring formed by atoms and one or more optional elements is meant.
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms are different.
  • the ring formed by R 921 and R 922 is a benzene ring.
  • the ring is 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 an arbitrary substituent.
  • the formed ring is a heterocyclic ring.
  • “One or more optional elements” constituting a saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less. .
  • the aromatic hydrocarbon ring a structure in which the aryl group mentioned as a specific example in the specific example group G1 is terminated with a hydrogen atom is given.
  • the aromatic heterocyclic ring a structure in which the aromatic heterocyclic group described as a specific example in the specific example group G2 is terminated with a hydrogen atom is given.
  • Specific examples of the aliphatic hydrocarbon ring include a structure in which the cycloalkyl group mentioned as a specific example in Specific Example Group G6 is terminated with a hydrogen atom.
  • the substituent is, for example, an “optional substituent” described later.
  • Specific examples of the substituent in the case where the above “saturated or unsaturated ring” has a substituent are the substituents described in the above section of “the substituent described in the present specification”.
  • the substituent in the case of “substituted or unsubstituted” may be: 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 carbon atoms for ring formation, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), -N ( R906 ) ( R907 ) (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
  • 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 substituents when referred to as "substituted or unsubstituted” are: 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 substituents when referred to as "substituted or unsubstituted” are: 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.
  • adjacent substituents may be substituted with a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5- or 6-membered ring, (Preferably, a benzene ring).
  • an optional substituent may further have a substituent unless otherwise specified. Examples of the substituent further included in the optional substituent include those similar to the optional substituent described above.
  • An organic EL device is A cathode, An anode, A light-emitting layer disposed between the cathode and the anode, Have The light emitting layer is A compound represented by the following formula (1): A compound represented by the following formula (11): It is characterized by containing.
  • Ar 1 is bonded to either or both of R 3 and R 13 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • Ar 2 is bonded to either or both of R 5 and R 6 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.
  • Ar 1 and Ar 2 that do not form a substituted or unsubstituted heterocycle are each independently It is an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
  • One or more adjacent two or more sets of R 1 to R 13 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
  • R 1 to R 13 which are not involved in the formation of the substituted or unsubstituted heterocycle and the formation of the substituted or unsubstituted saturated or unsaturated ring 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-forming carbon atoms, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), Halogen atom, cyano group, nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocycl
  • R 901 to R 905 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-forming carbon atoms, 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.
  • each of the two or more R 901 to R 905 may be the same or different.
  • 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 carbon atoms for ring formation, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), 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.
  • n and n are each independently R 1 and R, which are Ar 1 and Ar 2 and which can be substituted with an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms. It is a number of two .
  • R 1 's may be the same or different
  • n is 2 or more
  • two or more R 2 's may be the same. And may be different.
  • Ar 1 is bonded to either or both of R 3 and R 13 to form a substituted or unsubstituted heterocycle
  • Ar 2 is R 5 or R 6 to form a substituted or unsubstituted heterocycle by being bonded to one or both of 6 to form a substituted or unsubstituted heterocycle.
  • Ar 1 is bonded to R 3 to form a heterocycle Ha containing a nitrogen atom
  • ring Ha may have an arbitrary substituent.
  • the optional substituents may be the R 1, it may be a substituent other than R 1.
  • Ar 1 , Ar 2 , R 1 , R 2 , R 4 to R 13 , m and n are as defined in the formula (1).
  • Ha is a ring containing a nitrogen atom as a ring-forming element. Ring Ha may have a substituent.
  • R 1 ⁇ R 13 The "adjacent two of of R 1 ⁇ R 13", specifically, R 2 to each other when together R 1 when R 1 there are a plurality, R 2 there are a plurality, R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10 and R 11 , R 11 and R 12 , and R 12 and R 13 respectively.
  • “One or more adjacent two or more pairs of R 3 to R 13 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring” will be described with reference to specific examples.
  • the following formula (1-2) shows the case where one set of R 7 and R 8 forms an unsubstituted benzene ring.
  • Formula (1-3) below shows the case where one set of R 8 and R 9 forms an unsubstituted benzene ring.
  • Formula (1-4) below shows the case where two sets of R 7 and R 8 and R 11 and R 12 each form an unsubstituted benzene ring.
  • the following formula (1-5) shows the case where two groups of R 8 and R 9 and R 10 and R 11 each form an unsubstituted benzene ring.
  • Ar 1 , Ar 2 , R 1 to R 5 , R 7 , R 9 , R 10 to R 12 , m and n are the same as those in the formula (1). As defined.)
  • Ar 1 and Ar 2 which do not form a substituted or unsubstituted heterocycle are each independently an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
  • ”And“ m and n can be independently substituted with an aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms, which are Ar 1 and Ar 2. The number of R 1 and R 2 ”.
  • Ar 1 and Ar 2 are each a monovalent aromatic hydrocarbon bonded only N Is a group or a monovalent heterocyclic group, and when m and n are 1, Ar 1 and Ar 2 are respectively bonded to 1 R 1 and N, and 1 R 2 and N 2 It is a valence group. Further, for example, when m and n are 2 or more, Ar 1 and Ar 2 are respectively bonded to N and m R 1 and N and n R 2 respectively, and have (m + 1) valence and ( n + 1) valent group.
  • Each group (R 1 to R 13 ) of the compound represented by the formula (1) does not become a substituted or unsubstituted amino group. Furthermore, the optional substituents of the above groups and the optional substituents of the rings when the above groups form a ring do not become substituted or unsubstituted amino groups.
  • both Ar 1 and Ar 2 in the above formula (1) do not form the above-mentioned substituted or unsubstituted heterocycle.
  • the compound represented by the formula (1) is a compound represented by the following formula (2).
  • R 1 to R 13 are as defined in the formula (1).
  • m1 and n1 are each independently an integer of 0 to 5.
  • a plurality of R 1 and R 2 may be the same or different from each other.
  • the compound represented by the formula (1) is a compound represented by the following formula (3).
  • R 4 , R 7 , R 8 , R 11 and R 12 are as defined in the formula (1).
  • R 14 to R 19 are the same as R 1 and R 2 in the formula (1), respectively.
  • the compound represented by the formula (1) is a compound represented by the following formula (5).
  • R 7b , R 8b , R 11b , R 12b and R 14b to R 19b are each independently Hydrogen atom, It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • R 4c 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-forming carbon atoms, 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.
  • R 1 to R 13 in the formula (1) are each independently Hydrogen atom, It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • the compound represented by the above formula (1) is a compound represented by the following formula (6).
  • R 8d , R 11d , R 15d and R 18d are each independently It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • R 4b is Hydrogen atom, It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
  • the compound represented by the formula (1) includes, for example, a group containing three benzene rings and a group containing N-Ar 1- (R 1 ) m and a group containing N-Ar 2- (R 2 ) n.
  • the intermediate product can be produced by binding with (1st reaction), and the final product can be produced by binding the three benzene rings with a linking group (group containing B) (2nd reaction).
  • group containing B 2nd reaction
  • an amination reaction such as a Bhabhurt-Hartwig reaction can be applied.
  • a tandem hetero Friedel-Crafts reaction or the like can be applied.
  • Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and composed of only a benzene ring.
  • L 101 and L 102 are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and composed only of a benzene ring.
  • the total number of benzene rings forming Ar 101 , L 101, and L 102 is 2 or more.
  • R 911 to R 913 are each independently an alkyl group having 1 to 50 carbon atoms. When two or more R 911 to R 913 are present, each of the two or more R 911 to R 913 may be the same or different.
  • R 101 to R 104 and two or more adjacent ones of R 105 to R 108 do not bond with each other to form a ring.
  • Two or more adjacent R 111 to R 117 do not bond to each other to form a ring.
  • R 101 to R 108 and R 111 to R 117 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-forming carbon atoms, —Si (R 901 ) (R 902 ) (R 903 ), —O— (R 904 ), -S- (R 905 ), -N (R 906 ) (R 907 ), Halogen atom, cyano group,
  • R 901 to R 905 are as defined in the above formula (1).
  • R 906 and 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-forming carbon atoms, 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.
  • each of the two or more R 906 and R 907 may be the same or different.
  • the aryl group and arylene group “consisting only of a benzene ring” mean that aryl groups and arylene groups containing rings other than the benzene ring are excluded. Specifically, groups derived from a fluorene ring containing a 5-membered ring in addition to the benzene ring are excluded.
  • An aryl group and an arylene group “consisting only of a benzene ring” are a group consisting of a benzene ring monocycle (that is, a phenyl group and a phenylene group), and a group in which two or more benzene rings are continuously bonded via a single bond.
  • a biphenylyl group, a biphenyldiyl group, etc. and a group composed of a condensed ring of a benzene ring (for example, a naphthyl group, a naphthylene group, etc.).
  • the aryl group and the arylene group composed of only a benzene ring may be substituted with an arbitrary substituent described later.
  • the total number of benzene rings forming Ar 101 , L 101 and L 102 is 2 or more means that both L 101 and L 102 are single bonds ( When the total number of benzene rings is 0), Ar 101 is an aryl group having 2 or more benzene rings. Specific examples of Ar 101 in this case include a biphenylyl group (2 benzene rings), a naphthyl group (2 benzene rings), a phenanthryl group (3 benzene rings), an anthracenyl group (3 benzene rings), and the like.
  • Ar 101 is an aryl group composed of only one or more benzene rings.
  • both L 101 and L 102 are phenylene groups (the total number of benzene rings is 2)
  • Ar 101 is an aryl group composed of only one or more benzene rings, and The sum of the numbers is 3 or more.
  • Substituents in the case where Ar 101 , L 101 and L 102 , which are aryl groups and arylene groups composed only of a benzene ring, are substituted are: An alkyl group having 1 to 50 carbon atoms, An alkenyl group having 2 to 50 carbon atoms, An alkynyl group having 2 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring carbon atoms, -Si (R 911 ) (R 912 ) (R 913 ), It is a halogen atom or a cyano group.
  • R 911 to R 913 are each independently an alkyl group having 1 to 50 carbon atoms, and examples thereof include a trimethylsilyl group and a triethylsilyl group.
  • R 911 to R 913 are present, that is, when two or more optional substituents —Si (R 911 ) (R 912 ) (R 913 ) are present, two or more R 911 to R 913 Each may be the same or different.
  • Ar 101 in the above formula (11) is selected from the groups represented by the following formulas (a1) to (a4).
  • R 120 is An alkyl group having 1 to 50 carbon atoms, An alkenyl group having 2 to 50 carbon atoms, An alkynyl group having 2 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring carbon atoms, An alkylsilyl group having 1 to 50 carbon atoms, It is a halogen atom or a cyano group.
  • the arylene group is Each is independently selected from the groups represented by the following formulas (b1) to (b17).
  • R 120 is An alkyl group having 1 to 50 carbon atoms, An alkenyl group having 2 to 50 carbon atoms, An alkynyl group having 2 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring carbon atoms, -Si (R 911 ) (R 912 ) (R 913 ), It is a halogen atom or a cyano group.
  • R 911 to R 913 are each independently an alkyl group having 1 to 50 carbon atoms.
  • each of the two or more R 911 to R 913 may be the same or different.
  • m4 is an integer of 0 to 4.
  • m5 is an integer of 0 to 6.
  • m4 and m5 are each 2 or more, a plurality of R 120 may be the same as or different from each other.
  • adjacent R 120's are bonded to each other to form a saturated or unsaturated ring, or do not form a saturated or unsaturated ring.
  • Ar 101 in the above formula (11) is A substituted or unsubstituted phenyl group, A substituted or unsubstituted naphthyl group, A substituted or unsubstituted biphenylyl group, A substituted or unsubstituted terphenylyl group, A substituted or unsubstituted anthryl group, A substituted or unsubstituted phenanthryl group, A substituted or unsubstituted benzophenanthryl group, A substituted or unsubstituted pyrenyl group, It is a substituted or unsubstituted chrysenyl group or a substituted or unsubstituted triphenylenyl group.
  • L 101 and L 102 in the formula (11) are each independently Single bond, A substituted or unsubstituted phenylene group, A substituted or unsubstituted naphthylene group, A substituted or unsubstituted biphenyldiyl group, A substituted or unsubstituted terphenyldiyl group, A substituted or unsubstituted anthrylene group, A substituted or unsubstituted phenanthrylene group, A substituted or unsubstituted benzophenanthrylene group, A substituted or unsubstituted pyrenediyl group, A substituted or unsubstituted chrysendiyl group or a substituted or unsubstituted triphenylenediyl group.
  • the total number of benzene rings of Ar 101 , L 101, and L 102 in the formula (11) is 2 or more and 4 or less.
  • R 101 to R 108 in the above formula (11) are hydrogen atoms.
  • R 111 to R 117 in the above formula (11) are hydrogen atoms.
  • the compound represented by the formula (11) is a compound represented by the following formula (12).
  • L 102a is A substituted or unsubstituted phenylene group, A substituted or unsubstituted naphthylene group, A substituted or unsubstituted biphenyldiyl group, A substituted or unsubstituted terphenyldiyl group, A substituted or unsubstituted anthrylene group, A substituted or unsubstituted phenanthrylene group, A substituted or unsubstituted benzophenanthrylene group, A substituted or unsubstituted pyrenediyl group, A substituted or unsubstituted chrysendiyl group or a substituted or unsubstituted triphenylenediyl group.
  • the compound represented by the formula (11) is a compound represented by the following formula (13).
  • Ar 101 is as defined in Formula (11) above.
  • L 102a is A substituted or unsubstituted phenylene group, A substituted or unsubstituted naphthylene group, A substituted or unsubstituted biphenyldiyl group, A substituted or unsubstituted terphenyldiyl group, A substituted or unsubstituted anthrylene group, A substituted or unsubstituted phenanthrylene group, A substituted or unsubstituted benzophenanthrylene group, A substituted or unsubstituted pyrenediyl group, A substituted or unsubstituted chrysendiyl group or a substituted or unsubstituted triphenylenediyl group.
  • the compound represented by the formula (11) is a compound represented by the following formula (14).
  • L 101a is A substituted or unsubstituted phenylene group, A substituted or unsubstituted naphthylene group, A substituted or unsubstituted biphenyldiyl group, A substituted or unsubstituted terphenyldiyl group, A substituted or unsubstituted anthrylene group, A substituted or unsubstituted phenanthrylene group, A substituted or unsubstituted benzophenanthrylene group, A substituted or unsubstituted pyrenediyl group, A substituted or unsubstituted chrysendiyl group or a substituted or unsubstituted triphenylenediyl group.
  • the compound represented by the formula (11) is a compound represented by the following formula (15).
  • Ar 101 is as defined in Formula (11) above.
  • L 101a is A substituted or unsubstituted phenylene group, A substituted or unsubstituted naphthylene group, A substituted or unsubstituted biphenyldiyl group, A substituted or unsubstituted terphenyldiyl group, A substituted or unsubstituted anthrylene group, A substituted or unsubstituted phenanthrylene group, A substituted or unsubstituted benzophenanthrylene group, A substituted or unsubstituted pyrenediyl group, A substituted or unsubstituted chrysendiyl group or a substituted or unsubstituted triphenylenediyl group.
  • the compound represented by the formula (11) is a compound represented by the following formula (16).
  • R 101 to R 108 and R 111 to R 117 are as defined in the formula (11).
  • Ar 101a is A substituted or unsubstituted naphthyl group, A substituted or unsubstituted biphenylyl group, A substituted or unsubstituted terphenylyl group, A substituted or unsubstituted anthryl group, A substituted or unsubstituted phenanthryl group, A substituted or unsubstituted benzophenanthryl group, A substituted or unsubstituted pyrenyl group, It is a substituted or unsubstituted chrysenyl group or a substituted or unsubstituted triphenylenyl group.
  • the compound represented by the formula (11) is a compound represented by the following formula (17).
  • Ar 101a is A substituted or unsubstituted naphthyl group, A substituted or unsubstituted biphenylyl group, A substituted or unsubstituted terphenylyl group, A substituted or unsubstituted anthryl group, A substituted or unsubstituted phenanthryl group, A substituted or unsubstituted benzophenanthryl group, A substituted or unsubstituted pyrenyl group, It is a substituted or unsubstituted chrysenyl group or a substituted or unsubstituted triphenylenyl group.
  • Ar 101 in the above formula (11) is It is a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group.
  • the organic EL device has a cathode, an anode, and a light emitting layer between the cathode and the anode, and the organic layer is represented by the formula (1).
  • the organic layer is represented by the formula (1).
  • conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired.
  • the content of the compound represented by the formula (1) in the light emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light emitting layer. Further, the content of the compound represented by the formula (11) in the light emitting layer is preferably 80% by mass or more and 99% by mass or less with respect to the entire light emitting layer.
  • One aspect of the organic EL device of the present invention preferably has a hole transport layer between the anode and the light emitting layer.
  • One aspect of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the light emitting layer.
  • An organic EL element includes an organic layer between a pair of electrodes including a cathode and an anode.
  • the organic layer includes at least one layer containing an organic compound.
  • the organic layer is formed by stacking a plurality of layers containing an organic compound.
  • the organic layer may have a layer composed of only one or a plurality of organic compounds.
  • the organic layer may have a layer that simultaneously contains an organic compound and an inorganic compound.
  • the organic layer may have a layer composed of only one or more inorganic compounds. At least one of the layers included in the organic layer is a light emitting layer.
  • the organic layer may be configured as, for example, one light emitting layer, or may include other layers that can be adopted in the layer configuration of the organic EL element.
  • the layer that can be adopted in the layer structure of the organic EL element is not particularly limited, but for example, a hole transport zone (hole transport layer, hole injection layer, provided between the anode and the light emitting layer, Electron blocking layer, exciton blocking layer, etc.), light emitting layer, space layer, electron transporting zone (electron transporting layer, electron injecting layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer.
  • the organic EL element according to one aspect of the present invention may be, for example, a fluorescent or phosphorescent light emitting 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 including an organic layer, at least one of the organic layers being a light emitting layer, and emitting light by recombination of injected holes and electrons. Further, the “light emitting layer” described in the present specification is an organic layer having a light emitting function.
  • the light emitting layer is, for example, a phosphorescent light emitting layer, a fluorescent light emitting layer, or the like, and may be a single layer or a plurality of layers.
  • the light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers or fluorescent light emitting layers. In this case, for example, a space layer for preventing excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer. May be provided between each light emitting layer.
  • Examples of the simple organic EL element include element configurations such as an anode / a light emitting unit / a 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 emitting layer / second phosphorescent emitting layer (/ electron transporting layer / electron injecting layer)
  • E (Hole injection layer /) Hole transport layer / Phosphorescence emission layer / Space layer / Fluorescence emission layer (/ Electron transport layer / Electron 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 preferably 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.
  • 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. Only one of the first light emitting unit and the second light emitting unit may be the light emitting layer of one embodiment of the present invention, or both may be the light emitting layer of one embodiment of the present invention.
  • the substrate is used as a support for the organic EL device.
  • the substrate preferably has a light transmittance of 50% or more in the visible light region having a wavelength of 400 to 700 nm, and is preferably a smooth substrate.
  • Examples of the material of the substrate include soda lime glass, aluminosilicate glass, quartz glass, plastic and the like.
  • a flexible substrate can be used as the substrate.
  • the flexible substrate refers to a substrate that can be bent (flexible), and examples thereof include a plastic substrate.
  • Specific examples of the material forming the plastic substrate include polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate and the like.
  • an inorganic vapor deposition film can be used.
  • anode for example, a metal, an alloy, a conductive compound, a mixture thereof, or the like, which has a large work function (specifically, 4.0 eV or more) is preferably used.
  • the material of the anode include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and oxide containing zinc oxide. Examples include indium and graphene.
  • gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (for example, titanium nitride) can be given.
  • the anode is usually formed by depositing these materials on a substrate by a sputtering method.
  • indium oxide-zinc oxide can be formed by a sputtering method using a target in which zinc oxide is added at 1 to 10 mass% with respect to indium oxide.
  • a target in which 0.5 to 5 mass% of tungsten oxide or 0.1 to 1 mass% of zinc oxide is added to indium oxide is used. It can be formed by a sputtering method.
  • Other methods of forming the anode include, for example, a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method and the like. For example, when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.
  • the hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. Therefore, a general electrode material such as a metal, an alloy, a conductive compound, or a mixture thereof can be used for the anode. Specifically, alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (eg magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium. A material having a small work function such as an alloy containing a rare earth metal may be used for the anode.
  • alkali metals such as lithium and cesium
  • magnesium alkaline earth metals such as calcium and strontium
  • alloys containing these metals eg magnesium-silver, aluminum-lithium
  • rare earth metals such as europium and ytterbium.
  • a material having a small work function such as an alloy containing
  • the hole-injection layer is a layer containing a substance having a high hole-injection property and has a function of injecting holes from the anode into the organic layer.
  • the substance having a high hole injecting property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide.
  • aromatic amine compound examples include 4,4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ′′ -tris [N- (3 -Methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4, 4′-bis (N- ⁇ 4- [N ′-(3-methylphenyl) -N′-phenylamino] phenyl ⁇ -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [ N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [
  • a heterocyclic derivative having an electron-withdrawing group for example, a quinone derivative having an electron-withdrawing group, an arylborane derivative, a heteroarylborane derivative and the like are preferable, and specific examples thereof include hexacyanohexaazatriphenylene, 2, 3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (abbreviation: F4TCNQ), 1,2,3-tris [(cyano) (4-cyano-2,3,5,5) 6-tetrafluorophenyl) methylene] cyclopropane and the like.
  • the hole injection layer preferably further contains a matrix material.
  • a material known as a material for an organic EL device can be used, and for example, an electron donating (donor) compound is preferably used.
  • the hole-transporting layer is a layer containing a substance having a high hole-transporting property and has a function of transporting holes from the anode to the organic layer.
  • the substance having a high hole-transporting property is preferably a substance having a hole mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more, and examples thereof include aromatic amine compounds, carbazole derivatives, anthracene derivatives, and Examples thereof include molecular compounds.
  • aromatic amine compound examples include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), N, N′-bis (3-methylphenyl)- N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation) : BAFLP), 4,4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-N-
  • carbazole derivative examples include 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9 -Phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA) and the like can be given.
  • CBP 4,4′-di (9-carbazolyl) biphenyl
  • CzPA 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene
  • PCzPA 9 -Phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole
  • anthracene derivative examples include 2-t-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), Examples thereof include 9,10-diphenylanthracene (abbreviation: DPAnth).
  • polymer compound examples include poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA).
  • the compound has a hole transporting property higher than an electron transporting property
  • a substance other than these may be used in the hole transporting layer.
  • the hole transport layer may be a single layer or a laminate of two or more layers. In this case, it is preferable to dispose a layer containing a substance having a large energy gap among substances having a high hole transporting property on the side closer to the light emitting layer.
  • the light emitting layer is a layer containing a substance having high light emitting property (dopant material).
  • dopant material various materials can be used, and for example, a fluorescent light emitting compound (fluorescent dopant), a phosphorescent light emitting compound (phosphorescent dopant), and the like can be used.
  • the fluorescence emitting compound is a compound capable of emitting light from a singlet excited state, and a light emitting layer containing the compound is called a fluorescence emitting layer.
  • the phosphorescent compound is a compound capable of emitting light from a triplet excited state, and a light emitting layer containing the compound is called a phosphorescent layer.
  • the light emitting layer usually contains a dopant material and a host material for making it emit light efficiently.
  • the dopant material may be referred to as a guest material, an emitter, or a light emitting material depending on the literature.
  • the host material may also be referred to as a matrix material depending on the literature.
  • One light emitting layer may include a plurality of dopant materials and a plurality of host materials. Further, there may be a plurality of light emitting layers.
  • a host material combined with a fluorescent dopant is referred to as a “fluorescent host”, and a host material combined with a phosphorescent dopant is referred to as a “phosphorescent host”.
  • a fluorescent host a host material combined with a phosphorescent dopant
  • a phosphorescent host a host material combined with a phosphorescent dopant
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure.
  • the phosphorescent host is a material forming a phosphorescent emitting layer containing a phosphorescent dopant, but does not mean that it cannot be used as a material forming a fluorescent emitting layer. The same applies to the fluorescent host.
  • the content of the dopant material in the light emitting layer is not particularly limited, but from the viewpoint of sufficient light emission and concentration quenching, it is preferably 0.1 to 70% by mass, and more preferably 0.1% by mass. -30% by mass, more preferably 1-30% by mass, even more preferably 1-20% by mass, particularly preferably 1-10% by mass.
  • fluorescent dopant examples include, for example, fused polycyclic aromatic derivatives, styrylamine derivatives, condensed ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, Examples thereof include carbazole derivatives. Of these, condensed ring amine derivatives, boron-containing compounds and carbazole derivatives are preferable.
  • Examples of the condensed ring amine derivative include a diaminopyrene derivative, a diaminochrysene derivative, a diaminoanthracene derivative, a diaminofluorene derivative, and a diaminofluorene derivative in which one or more benzofuro skeletons are condensed.
  • Examples of the boron-containing compound include a pyrromethene derivative and a triphenylborane derivative.
  • the blue fluorescent dopant that can be used with the fluorescent dopant used in one embodiment of the present invention includes, for example, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, and a triarylamine derivative. Etc.
  • N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S)
  • 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA)
  • 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine abbreviation: PCBAPA
  • Examples of the green fluorescent dopant that can be used with the fluorescent dopant used in one embodiment of the present invention include aromatic amine derivatives. Specifically, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N'-triphenyl-1,4-phenylenediamine (abbrevi
  • a tetracene derivative, a diamine derivative, or the like can be used together with the fluorescent dopant used in one embodiment of the present invention.
  • N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine abbreviation: p-mPhTD
  • 7,14-diphenyl-N N, N ′, N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine
  • p-mPhAFD tetracene derivative, a diamine derivative, or the like
  • Examples of the phosphorescent dopant include a phosphorescent heavy metal complex and a phosphorescent rare earth metal complex.
  • Examples of the heavy metal complex include iridium complex, osmium complex, platinum complex and the like.
  • the heavy metal complex is preferably an orthometallated complex of a metal selected from iridium, osmium, and platinum.
  • Examples of rare earth metal complexes include terbium complexes and europium complexes.
  • These rare earth metal complexes are preferable as phosphorescent dopants because rare earth metal ions emit light due to electronic transition between different multiplicities.
  • blue phosphorescent dopant examples include iridium complex, osmium complex, and platinum complex. Specifically, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6), bis [2- (4 ′ , 6′-Difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ′, 5′-bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium ( III) picolinate (abbreviation: Ir (CF3ppy) 2 (pic)), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III)
  • green phosphorescent dopants include iridium complexes. Specifically, tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) 3 ), bis (2-phenylpyridinato-N, C2 ′) iridium (III ) Acetylacetonate (abbreviation: Ir (ppy) 2 (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) 2 (acac)) , Bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) 2 (acac)), and the like.
  • iridium complexes Specifically, tris (2-phenylpyridinato-N, C2 ′) i
  • red phosphorescent dopants include iridium complexes, platinum complexes, terbium complexes, europium complexes and the like. Specifically, bis [2- (2′-benzo [4,5- ⁇ ] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (btp) 2 (acac)), Bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) 2 (acac)), (acetylacetonato) bis [2,3-bis (4-fluoro) (Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) 2 (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H
  • ⁇ Host material> examples of materials that can be used with the host material used in one embodiment of the present invention include metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; indole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinolines.
  • Heterocyclic compounds such as derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives; naphthalene derivatives, triphenylene derivatives, carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, Condensed aromatic compounds such as chrysene derivatives, naphthacene derivatives and fluoranthene derivatives; aromatic compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives Family amine compounds, and the like.
  • a plurality of types of host materials may be used in combination.
  • metal complex examples include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq3), bis (10-hydroxybenzo).
  • heterocyclic compound examples include 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD) and 1,3-bis [5 -(P-tert-Butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-biphenylyl) -4-phenyl-5- (4- tert-Butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 2,2 ′, 2 ′′-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzimidazole) (Abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and the like can be given.
  • PBD 2- (4-biphenylyl) -5- (4
  • condensed aromatic compound examples include 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA) and 3,6-diphenyl-9- [4- (10- Phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: DPCzPA), 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene ( Abbreviation: DNA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(stilbene- 3,3′-diyl) diphenanthrene (abbreviation: DPNS), 9,9 ′-(stilbene-4
  • aromatic amine compound examples include N, N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10 -Phenyl-9-anthryl) triphenylamine (abbreviation: DPhPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA) ), N, 9-diphenyl-N- ⁇ 4- [4- (10-phenyl-9-anthryl) phenyl] phenyl ⁇ -9H-carbazol-3-amine (abbreviation: PCAPBA), N- (9,10- Diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4′-bis [N- (1-(-
  • the fluorescent host is preferably a compound having a singlet level higher than that of the fluorescent dopant, and examples thereof include a heterocyclic compound and a condensed aromatic compound.
  • the condensed aromatic compound for example, anthracene derivative, pyrene derivative, chrysene derivative, naphthacene derivative and the like are preferable.
  • the phosphorescent host is preferably a compound having a triplet level higher than that of the phosphorescent dopant, and examples thereof include a metal complex, a heterocyclic compound, and a condensed aromatic compound.
  • examples thereof include a metal complex, a heterocyclic compound, and a condensed aromatic compound.
  • indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. preferable.
  • the electron-transporting layer is a layer containing a substance having a high electron-transporting property.
  • the substance having a high electron-transporting property is preferably a substance having an electron mobility of 10 ⁇ 6 cm 2 / Vs or more, and examples thereof include metal complexes, aromatic heterocyclic compounds, aromatic hydrocarbon compounds, and polymer compounds. Etc.
  • Examples of the metal complex include aluminum complex, beryllium complex, zinc complex and the like. Specifically, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato) beryllium (Abbreviation: BeBq2), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), and the like can be given.
  • Alq tris (8-quinolinolato) aluminum (
  • aromatic heterocyclic compound examples include imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives and benzimidazophenanthridine derivatives; azine derivatives such as pyrimidine derivatives and triazine derivatives; quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives and the like.
  • imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives and benzimidazophenanthridine derivatives
  • azine derivatives such as pyrimidine derivatives and triazine derivatives
  • quinoline derivatives isoquinoline derivatives, phenanthroline derivatives and the like.
  • examples thereof include compounds having a nitrogen six-membered ring structure (including those having a phosphine oxide-based substituent on the heterocycle).
  • aromatic hydrocarbon compounds examples include anthracene derivatives and fluoranthene derivatives.
  • polymer compound examples include poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9 , 9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like.
  • the compound has a higher electron transporting property than the hole transporting property, a substance other than these may be used in the electron transporting layer.
  • the electron transport layer may be a single layer or a laminate of two or more layers. In this case, it is preferable to dispose a layer containing a substance having a large energy gap among substances having a high electron transporting property on the side closer to the light emitting layer.
  • a metal such as an alkali metal, magnesium, an alkaline earth metal, an alloy containing two or more of these metals; an alkali metal compound such as 8-quinolinolatolithium (abbreviation: Liq),
  • Liq 8-quinolinolatolithium
  • a metal compound such as an alkaline earth metal compound may be contained.
  • the content thereof is not particularly limited, but 0
  • the amount is preferably 1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.
  • the electron transport layer contains a metal compound such as an alkali metal compound or a metal compound such as an alkaline earth metal compound, the content thereof is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. Is.
  • the layer on the side of the light emitting layer in the case where the electron transport layer has a plurality of layers may be formed of only these metal compounds.
  • the electron injection layer is a layer containing a substance having a high electron injection property, and has a function of efficiently injecting electrons from the cathode to the light emitting layer.
  • the substance having a high electron injecting property include alkali metals, magnesium, alkaline earth metals, and compounds thereof. Specific examples include lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, and lithium oxide.
  • a substance having an electron-transporting property containing an alkali metal, magnesium, an alkaline earth metal, or a compound thereof, for example, a substance containing Alq containing magnesium can be used.
  • a composite material containing an organic compound and a donor compound can be used for the electron-injection layer. Since the organic compound receives an electron from the compound having a donor property, such a composite material has an excellent electron injecting property and an electron transporting property.
  • a substance having an excellent electron-transporting property is preferable, and for example, the above-described substance having a high electron-transporting property such as a metal complex or an aromatic heterocyclic compound can be used.
  • the donor compound may be any substance that can donate an electron to an organic compound, and examples thereof include alkali metals, magnesium, alkaline earth metals, and rare earth metals. Specific examples include lithium, cesium, magnesium, calcium, erbium and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferable, and specific examples thereof include lithium oxide, calcium oxide, and barium oxide. It is also possible to use a Lewis base such as magnesium oxide. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • TTF tetrathiafulvalene
  • the cathode is preferably a metal, an alloy, a conductive compound, or a mixture thereof, which has a low work function (specifically, 3.8 eV or less).
  • materials for the cathode include alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (eg magnesium-silver, aluminum-lithium); europium, ytterbium, etc. Rare earth metals; alloys containing rare earth metals, and the like.
  • the cathode is usually formed by a vacuum vapor deposition method or a sputtering method. When silver paste or the like is used, a coating method, an inkjet method, or the like can be used.
  • the cathode is formed by using various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the work function. Can be formed. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
  • a thin film insulating layer may be inserted between the pair of electrodes.
  • the substance used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and oxide. Examples thereof include silicon, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. A mixture of these materials can be used for the insulating layer, or a stack of a plurality of layers containing these substances can be used.
  • the space layer is provided between the two layers in order to prevent diffusion of excitons generated in the phosphorescent emitting layer into the fluorescent emitting layer and to adjust carrier balance when the fluorescent emitting layer and the phosphorescent emitting layer are stacked, for example. It is provided.
  • the space layer can also be provided between a plurality of phosphorescent emitting layers and the like. Since the space layer is provided between the plurality of light emitting layers, it is preferably formed of a substance having both an electron transporting property and a hole transporting property. Further, the triplet energy is preferably 2.6 eV or more from the viewpoint of preventing diffusion of the triplet energy in the adjacent phosphorescent emitting layer. Examples of the substance used for the space layer include the same substances as those used for the hole transport layer described above.
  • An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc. may be provided adjacent to the light emitting layer.
  • the electron blocking layer is a layer having a function of blocking leakage of electrons from the light emitting layer to the hole transport layer.
  • the hole blocking layer is a layer having a function of blocking leakage of holes from the light emitting layer to the electron transport layer.
  • the exciton blocking layer is a layer having a function of blocking excitons generated in the light emitting layer from diffusing into an adjacent layer and confining the excitons in the light emitting layer.
  • the method for forming each layer of the organic EL element is not particularly limited, unless otherwise specified.
  • a forming method a known method such as a dry film forming method or a wet film forming method can be used.
  • Specific examples of the dry film forming method include a vacuum vapor deposition method, a sputtering method, a plasma method, an ion plating method and the like.
  • Specific examples of the wet film forming method include various coating methods such as a spin coating method, a dipping method, a flow coating method, and an inkjet method.
  • the film thickness of each layer of the organic EL element is not particularly limited, unless otherwise specified. If the film thickness is too small, defects such as pinholes are likely to occur and sufficient emission brightness cannot be obtained. On the other hand, if the film thickness is too large, a high driving voltage is required and the efficiency decreases. From such a viewpoint, the film thickness is usually preferably 1 nm to 10 ⁇ m, more preferably 1 nm to 0.2 ⁇ m.
  • An electronic device includes the above-described organic EL element according to one aspect of the present invention.
  • Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, smartphones, and personal computers; lighting, and light-emitting devices for vehicle lamps.
  • 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 cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and the compound HA-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. HA-1 film was formed. This HA-1 film functions as a hole injection layer.
  • ITO transparent electrode anode
  • UV ozone cleaning for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum vapor deposition apparatus, and the compound HA-1 was
  • the compound HT-1 was vapor-deposited to form an HT-1 film having a film thickness of 80 nm on the HA-1 film.
  • This HT-1 film functions as a hole transport layer (first hole transport layer).
  • a compound HT-2 was deposited, and a 10 nm-thick HT-2 film was formed on the HT-1 film.
  • This HT-2 film functions as an electron blocking layer (second hole transport layer).
  • a compound BH-1 (host material) and a compound BD-1 (dopant material) are co-deposited on the HT-2 film so that the ratio of the compound BD-1 is 2% by mass.
  • a BD-1 film was formed.
  • This BH-1: BD-1 film functions as a light emitting layer.
  • Compound ET-1 was deposited on this light emitting layer to form a 10 nm-thick ET-1 film. This ET-1 film functions as a hole barrier layer.
  • Compound ET-2 was deposited on the ET-1 film to form a 15 nm-thick ET-2 film. This ET-2 film functions as an electron transport layer.
  • LiF was deposited on the ET-2 film to form a 1 nm-thick LiF film.
  • 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) / HA-1 (5) / HT-1 (80) / HT-2 (10) / BH-1: BD-1 (25: 2% by mass) / ET-1 (10) / ET- 2 (15) / LiF (1) / Al (80)
  • the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the number in percent indicates the proportion (mass%) of the dopant material in the light emitting layer.
  • Examples 2 to 15 and Comparative Examples 1 to 6 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 as the host material and the dopant material. The results are shown in Table 1.
  • a dopant material used in Examples and Comparative Examples which is a polycyclic aromatic compound represented by the formula (1) and having a plurality of aromatic rings linked by a boron atom and a nitrogen atom, and having no amino group.
  • BD-1 tends to have a low hole trapping property.
  • the host materials BH-C1 and BH-C2 used in Comparative Example 1 in which the total number of benzene rings forming Ar 101 , L 101 and L 102 in the formula (11) is “1” are The hole injection property is high, and the recombination region tends to diffuse. Therefore, it was found that when the dopant material BD-1 and the host material BH-C1 or BH-C2 were combined, the recombination region was easily affected by diffusion.
  • the host materials BH-1 to BH-4 used in Examples in which the total number of benzene rings forming Ar 101 , L 101 and L 102 in the formula (11) is “2 or more”. Has a high electron transporting property and has an effect of suppressing diffusion in the recombination region. Therefore, it is considered that when the dopant material BD-1 and the host materials BH-1 to BH-4 and BH-5 are combined, the influence of diffusion of the recombination region is less likely to occur, and the external quantum efficiency is increased.

Abstract

Élément électroluminescent organique qui comprend une électrode négative, une électrode positive et une couche lumineuse disposée entre l'électrode négative et l'électrode positive, la couche lumineuse contenant un composé représenté par la formule (1) et un composé représenté par la formule (11) (le nombre total de cycles benzéniques formant Ar101, L101 et L102 est supérieur ou égal à 2).
PCT/JP2019/039828 2018-10-09 2019-10-09 Élément électroluminescent organique et dispositif électronique faisant appel à celui-ci WO2020075758A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113227105A (zh) * 2018-11-29 2021-08-06 默克专利有限公司 电子器件
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

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Publication number Priority date Publication date Assignee Title
WO2017188111A1 (fr) * 2016-04-26 2017-11-02 学校法人関西学院 Élément électroluminescent organique
US20190115538A1 (en) * 2017-10-16 2019-04-18 Samsung Display Co., Ltd. Organic light-emitting device and flat display apparatus including the same
JP2019161218A (ja) * 2018-03-08 2019-09-19 Jnc株式会社 有機電界発光素子
WO2019198699A1 (fr) * 2018-04-12 2019-10-17 学校法人関西学院 Composé aromatique polycyclique substitué par cycloalkyle

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017188111A1 (fr) * 2016-04-26 2017-11-02 学校法人関西学院 Élément électroluminescent organique
US20190115538A1 (en) * 2017-10-16 2019-04-18 Samsung Display Co., Ltd. Organic light-emitting device and flat display apparatus including the same
JP2019161218A (ja) * 2018-03-08 2019-09-19 Jnc株式会社 有機電界発光素子
WO2019198699A1 (fr) * 2018-04-12 2019-10-17 学校法人関西学院 Composé aromatique polycyclique substitué par cycloalkyle

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113227105A (zh) * 2018-11-29 2021-08-06 默克专利有限公司 电子器件
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

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