WO2024147304A1 - Composé, composition, élément organique électroluminescent et dispositif électronique - Google Patents

Composé, composition, élément organique électroluminescent et dispositif électronique Download PDF

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WO2024147304A1
WO2024147304A1 PCT/JP2023/046254 JP2023046254W WO2024147304A1 WO 2024147304 A1 WO2024147304 A1 WO 2024147304A1 JP 2023046254 W JP2023046254 W JP 2023046254W WO 2024147304 A1 WO2024147304 A1 WO 2024147304A1
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substituted
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ファブリス エッケス
ピエール ブフレ
ペーター ムーラー
祐一 西前
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K85/30—Coordination compounds
    • 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

Definitions

  • Patent Documents 1 and 2 disclose fused ring compounds containing nitrogen and boron atoms as compounds that can be used in organic electroluminescence devices.
  • an electronic device is provided that is equipped with an organic electroluminescence element according to one aspect of the present invention.
  • the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
  • the "atomic number XX to YY” in the expression “substituted or unsubstituted ZZ group having atomic number XX to YY” refers to the atomic number when the ZZ group is unsubstituted, and does not include the atomic number of the substituent when the ZZ group is substituted.
  • "YY" is larger than “XX”
  • "XX” means an integer of 1 or more
  • "YY” means an integer of 2 or more.
  • the hydrogen atom in the "unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
  • substitution in the case of "a substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "a BB group substituted with an AA group” means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B).
  • substituted heterocyclic group refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group” in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified.
  • the examples of the "unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” listed here are merely examples, and the “substituted heterocyclic group” described in this specification also includes the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the groups in the "substituted heterocyclic group” in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
  • Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2 , provided that at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or CH2 .
  • substituted fluoroalkyl group as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents include the examples of groups in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with fluorine atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification.
  • substituted haloalkyl group means a group in which one or more hydrogen atoms in the "haloalkyl group” are replaced with a substituent.
  • a specific example of the "substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • the number of carbon atoms in 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 "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • the number of ring carbon atoms of the "unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, a o-terphenyl-4-yl group, a o-terphenyl-3-yl group, a o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a
  • carbazolyl group is specifically any of the following groups:
  • substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
  • the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group".
  • Specific examples of the "substituted or unsubstituted arylene group” include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1.
  • Substituted or unsubstituted divalent heterocyclic group is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group".
  • Specific examples of the "substituted or unsubstituted divalent heterocyclic group” include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • the substituted or unsubstituted arylene group described herein is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents a bonding position.
  • Q 1 to Q 8 each independently represent a hydrogen atom or a substituent.
  • * represents a bonding position.
  • Q 1 to Q 9 each independently represent a hydrogen atom or a substituent.
  • a set of two or more adjacent rings forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded.
  • it means the case where R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , and a set of three adjacent rings (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and are condensed to the anthracene skeleton.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105).
  • ring Q A and ring Q C share R 922 .
  • the "monocyclic ring” or “fused ring” formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even if “one of the pairs of adjacent two" forms a “monocyclic ring” or a “fused ring", the “monocyclic ring” or the “fused ring” can form a saturated ring or an unsaturated ring.
  • the ring Q A and the ring Q B formed in the general formula (TEMP-104) are “monocyclic rings” or “fused rings", respectively.
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are “fused rings”.
  • the "monocyclic ring” and the “condensed ring” are preferred.
  • the "saturated ring” and the “unsaturated ring” are preferred.
  • a “monocyclic ring” is preferably a benzene ring.
  • the "unsaturated ring” is preferably a benzene ring.
  • one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted monocyclic ring” or “combine with each other to form a substituted or unsubstituted fused ring
  • one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring” consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.
  • the substituent in the above "substituted or unsubstituted” is: an alkyl group having 1 to 50 carbon atoms, The group is selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • R 131 to R 137 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
  • the plurality of R 131 are the same or different
  • the plurality of R 132 are present
  • the plurality of R 132 are the same or different
  • the plurality of R 133 are the same or different
  • the plurality of R 134s are present, the plurality of R 134s are the same or different from each other
  • a plurality of R 135 the plurality of R 1
  • the fused ring consisting of five or more rings is not particularly limited as long as it is a ring formed by condensing five or more monocyclic rings.
  • four benzene rings and one furan ring are condensed to form a dinaphtho[2,3-b:2',3'-d]furan ring represented by the following general formula (A2-1).
  • Consing a nitrogen atom, an oxygen atom or a sulfur atom as a part of the skeleton means that at least one of the five or more monocyclic rings constituting the "condensed ring composed of five or more rings" contains at least one nitrogen atom, an oxygen atom or a sulfur atom as a ring-forming atom.
  • the ring-forming atoms may contain atoms other than carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms, and may contain, for example, at least one atom selected from the group consisting of boron atoms and silicon atoms.
  • R 1 to R 11 , R A1 to R A11 , R B1 to R B11 , R C1 to R C16 , R D1 to R D11 , R E1 to R E11 , and R F1 to R F11 are each independently Hydrogen atoms,
  • condition (a1) at least one of R 1 to R 11 is a group represented by the above general formula (10) or a group represented by -L 13 -B 1 .
  • the compound represented by the general formula (12) satisfies the following condition (a3).
  • condition (a4) at least one of R B1 to R B11 is a group represented by the above general formula (10) or a group represented by -L 13 -B 1 .
  • Condition (a5) at least one of Y 1 A and Y 1 B is NL 13 -B 1 .
  • the compound represented by the general formula (14) satisfies the following condition (a6).
  • Condition (a10) at least one of Y 1 A and Y 1 B is NL 13 -B 1 .
  • the compound represented by the general formula (17) satisfies at least one of the following conditions (a11) and (a12).
  • R 1 to R 11 are the same as R 1 to R 11 in formula (11), respectively.
  • L 11 and L 12 each independently represent Single bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms
  • Ar 11 and Ar 12 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • X 1 in the general formula (112) is preferably C(R 129 )(R 130 ).
  • the compound represented by the general formula (1) when the compound represented by the general formula (1) is a compound represented by the general formula (11) and R7 is B1 , the compound represented by the general formula (1) is represented by the following general formula (121).
  • L 12 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms
  • Ar 12 is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • L 12 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms
  • Ar 12 is a group represented by the general formula (112a) above
  • X 1 is an oxygen atom.
  • one or more pairs of adjacent two or more of Ra, Rb, Rc, and AkD are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring.
  • ring D1 and ring D2 each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; provided that one or more of the hydrogen atoms bonded to ring D1 and the hydrogen atoms in the substituent bonded to ring D1 are deuterium atoms; One or more of the hydrogen atoms bonded to ring D2 and the hydrogen atoms in the substituents bonded to ring D2 are deuterium atoms.
  • Ar 1 is also preferably an aryl group having 6 to 50 ring carbon atoms and having one or more substituents selected from the group consisting of an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 13 ring atoms.
  • Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; Rd, Re, Rf and Rg each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -N(R 131 )(R 132 ), A group represented by -Si(R 133 )(R 134 )(R 135 ), a group represented by —O—(R 136 ), A
  • Ar 1 is also preferably a group represented by the following general formula (103) or (104).
  • B 1 is preferably a group represented by the following general formula (102).
  • Ra, Rb, Rc, Rd, Re, Rf, Rg, Ar 101 , and * are respectively defined as Ra, Rb, Rc, Rd, Re, Rf, Rg, Ar 101 , and * in the general formula (101).
  • Ak D is It is preferably an unsubstituted alkyl group having 1 to 50 carbon atoms in which all of the hydrogen atoms are deuterium atoms, or an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms in which all of the hydrogen atoms are deuterium atoms.
  • each AkD is independently A methyl group containing one or more deuterium atoms; an ethyl group containing one or more deuterium atoms; a tert-butyl group containing one or more deuterium atoms; An isopropyl group containing one or more deuterium atoms, or a substituted or unsubstituted cycloalkyl group containing one or more deuterium atoms and having 3 to 50 ring carbon atoms is preferred.
  • Ak D is also preferably an alkyl group having a branched chain.
  • each Ak D is preferably a methyl group containing one or more deuterium atoms.
  • all hydrogen atoms other than the hydrogen atom possessed by AkD in B1 which is the group represented by the general formula (10), are light hydrogen atoms.
  • all hydrogen atoms other than the hydrogen atom possessed by Ak D in the molecule of the compound represented by the general formula (1) are light hydrogen atoms.
  • the compound represented by the general formula (1) is preferably represented by the following general formula (114):
  • R 1 to R 6 and R 8 to R 11 are respectively defined as R 1 to R 6 and R 8 to R 11 in formula (11).
  • L11 is Single bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms
  • Ar 11 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms
  • Ra, Rb, Rc, Rd, Re, Rf and Rg each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or un
  • Ra, Rb and Rc each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, A group represented by -N(R 131 )(R 132 ), It is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ra, Rb and Rc each independently represent Hydrogen atoms, It is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • Ra and Rc are preferably hydrogen atoms, and Rb is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R 1 to R 11 which are not the group represented by the general formula (10) are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, A group represented by -N(R 131 )(R 132 ), It is preferably a substituted or unsubstituted hydrocarbon ring group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • R 1 to R 11 which are not the group represented by the general formula (10) are each independently Hydrogen atoms, It is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted hydrocarbon ring group having 6 to 30 ring carbon atoms.
  • R 1 , R 4 , R 5 , R 8 , R 9 and R 11 are preferably hydrogen atoms.
  • R 121 to R 128 , R 141 to R 144 , and R 151 to R 154 are each independently Hydrogen atoms, It is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the maximum peak wavelength of fluorescent emission may be referred to as the maximum peak wavelength of fluorescent emission.
  • the maximum fluorescence emission peak wavelength of the compound according to this embodiment is preferably 440 nm or more, and more preferably 445 nm or more.
  • the maximum fluorescence emission peak wavelength of the compound according to this embodiment is preferably 480 nm or less, and more preferably 470 nm or less.
  • the maximum fluorescence emission peak wavelength refers to the maximum peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 ⁇ 6 mol/L or more and 10 ⁇ 5 mol/L or less.
  • the measurement device may be a fluorescence spectrum measuring device (device name: FP-8300, manufactured by JASCO Corporation). Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.
  • the compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.
  • Specific examples of the compound according to this embodiment include the following compounds, however, the present invention is not limited to these specific examples.
  • the composition according to this embodiment contains the compound according to the first embodiment as the first compound.
  • the compound according to the first embodiment (first compound) is a deuterium compound containing at least one deuterium atom in the molecule.
  • the composition according to this embodiment contains or does not contain a protium compound Mp in which all hydrogen atoms in the compound (compound according to the first embodiment) represented by the general formula (1) are protium atoms (i.e., all hydrogen atoms present in the molecule are protium atoms, and no deuterium atoms are present in the molecule), and the content ratio D x of the first compound relative to the total of the first compound and the protium compound in the composition according to this embodiment is 0.1 mol % or more.
  • the composition according to the present embodiment may contain two or more compounds having different structures, so long as they are compounds represented by the general formula (1) (i.e., it may contain a plurality of first compounds. In this case, the total number of molecules of the plurality of first compounds is used as Xd in the formula (1D).
  • the composition according to the present embodiment may contain two or more compounds having different positions of deuterium, which are compounds represented by the general formula (1).
  • the compound represented by the general formula (1) "has deuterium atoms as hydrogen atoms”
  • the composition according to the present embodiment may contain two or more compounds having different ratios of deuterium atoms to the total of light hydrogen atoms and deuterium atoms in the hydrogen atoms.
  • composition according to one aspect of this embodiment contains a first compound and a protium compound Mp.
  • composition according to one aspect of this embodiment contains a first compound, a protium compound Mp, and one or more compounds other than the first compound and the protium compound Mp.
  • the content ratio Dx of the first compound relative to the total of the first compound and the protium compound Mp may be less than 100 mol%, 99 mol% or less, 95 mol% or less, 90 mol% or less, 80 mol% or less, 70 mol% or less, 60 mol% or less, 50 mol% or less, or 40 mol% or less.
  • the life span of the organic electroluminescence element can be extended.
  • the organic EL element according to this embodiment may be an organic EL element having a single light-emitting layer as a fourth embodiment.
  • the light-emitting layer preferably contains a second compound represented by the following general formula (H10).
  • the compound represented by the general formula (H10) may have a deuterium atom instead of a hydrogen atom.
  • the substituent in the "substituted or unsubstituted" case in the general formula (H10) is an alkyl group having 1 to 5 carbon atoms.
  • R 101A to R 108A , L 101 and Ar 101 are as defined in the general formula (H30D),
  • Xd is an oxygen atom or a sulfur atom;
  • one of R 121 to R 128 is a single bond bonding to L 101 ;
  • At least one pair of adjacent two or more of R 121 to R 128 which are not single bonds bonded to L 101 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • R 121 to R 128 which are not a single bond bonded to L 101 do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring are each independently a hydrogen atom or a substituent R,
  • the substituent R is as defined in formula (H10).
  • R 101A to R 108A are hydrogen atoms; a hydrogen atom held by R 101A to R 108A which are the substituents R; a hydrogen atom held by L 101 , a hydrogen atom possessed by a substituent of L 101 , A hydrogen atom held by Ar 101 , At least one of the hydrogen atoms possessed by the substituent of Ar 101 , the hydrogen atoms R 121 to R 128 , and the hydrogen atoms possessed by the substituents R R 121 to R 128 is a deuterium atom.
  • R 101A to R 108A are hydrogen atoms; a hydrogen atom held by R 101A to R 108A which are the substituents R; R 125A to R 128A are hydrogen atoms; a hydrogen atom held by R 125A to R 128A which are the substituents R; A hydrogen atom bonded to a carbon atom of a dibenzofuran skeleton in general formula (H32D), a hydrogen atom held by L 101 , a hydrogen atom possessed by a substituent of L 101 , At least one of the hydrogen atoms possessed by Ar 101 and the hydrogen atoms possessed by the substituent of Ar 101 is a deuterium atom.
  • At least one of the hydrogen atoms possessed by the compound represented by the general formula (H40), general formula (H41), general formula (H42-1) to general formula (H42-3), or general formula (H43-1) to general formula (H43-3) is a deuterium atom.
  • At least one of R 101A and R 103A to R 108A in general formula (H40D) is a deuterium atom.
  • the compound represented by the general formula (H40D) is a compound represented by any one of the following general formulas (H42D-1) to (H42D-3).
  • R 101A and R 103A to R 108A which are the substituents R; a hydrogen atom held by L 101 , a hydrogen atom possessed by a substituent of L 101 , A hydrogen atom held by Ar 101 , at least one of the hydrogen atoms of the substituent of Ar 101 and the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in general formula (H42D-1) is a deuterium atom,
  • R 101A and R 103A to R 108A are each a hydrogen atom; a hydrogen atom possessed by R 101A and R 103A to R 108A which are the substituents R; a hydrogen atom held by L 101 , a hydrogen atom possessed by a substituent of L 101 , A hydrogen atom held by Ar 101 , at least one of the hydrogen atoms of the substituent of Ar 101 and the hydrogen atoms bonded to the carbon atoms constituting the nap
  • L 101 and Ar 101 are as defined in the general formula (H40D). however, a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in general formula (H43D-1), a hydrogen atom held by L 101 , a hydrogen atom possessed by a substituent of L 101 , A hydrogen atom held by Ar 101 , at least one of a hydrogen atom possessed by a substituent of Ar 101 and a hydrogen atom bonded to a carbon atom constituting a phenyl group in general formula (H43D-1) is a deuterium atom, a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in general formula (H43D-2), a hydrogen atom held by L 101 , a hydrogen atom possessed by a substituent of L 101 , A hydrogen atom held by Ar 101 , at least one of the hydrogen atoms of the substituent of Ar 101
  • the position of the single bond with L 101 in general formula (H50) is not particularly limited.
  • one of R 151 to R 154 or one of R 155 to R 160 in general formula (H50) is a single bond bonding to L 101 .
  • Ar 101 is a monovalent group represented by the following general formula (H50-R 152 ), general formula (H50-R 153 ), general formula (H50-R 154 ), general formula (H50-R 157 ), or general formula (H50-R 158 ).
  • the organic EL element according to one aspect of the present invention has a cathode, an anode, and a light-emitting layer between the cathode and the anode.
  • a light-emitting layer containing the compound according to the first embodiment conventionally known materials and element configurations can be used as long as they do not impair the effects of the present invention.
  • the organic EL element of this embodiment preferably emits light having a maximum peak wavelength of 445 nm or more and 470 nm or less when the element is driven.
  • the maximum peak wavelength of light emitted from the organic EL element when the element is driven is measured as follows. A voltage is applied to the organic EL element so that the current density is 10 mA/ cm2 , and the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).
  • the light-emitting layer when the light-emitting layer contains the second compound, the light-emitting layer preferably contains the second compound in an amount of 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more of the total mass of the light-emitting layer.
  • the second compound is preferably a host material.
  • the upper limit of the total content of the host material and the dopant material is 100% by mass.
  • the organic EL element according to this embodiment will be described.
  • the organic EL element according to this embodiment may be, as a fifth embodiment, an organic EL element having two or more light-emitting layers.
  • the organic EL element of the fifth embodiment differs from the organic EL element of the fourth embodiment in that it has at least two light-emitting layers, but is otherwise similar to the organic EL element of the fourth embodiment.
  • the same components as those in the fourth embodiment will be omitted or simplified by using the same reference numerals, names, etc.
  • the same materials and compounds as those described in the first, second, third and fourth embodiments can be used.
  • the organic electroluminescent element has an anode, a cathode, and an emission band disposed between the anode and the cathode, the emission band includes a first emission layer and a second emission layer, the first emission layer contains a first host material and a first emission compound, the second emission layer contains a second host material and a second emission compound, the first host material and the second host material are different from each other, and the first emission compound and the second emission compound are the same as or different from each other.
  • the organic EL element according to this embodiment has at least two light-emitting layers (a first light-emitting layer and a second light-emitting layer). The following mainly describes the differences from the fourth embodiment, and redundant descriptions are omitted or simplified.
  • the first light-emitting layer may be disposed between the anode and the second light-emitting layer, and the first light-emitting layer may be disposed between the cathode and the second light-emitting layer. In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer is disposed between the anode and the second light-emitting layer.
  • the emission ratio (TTF ratio) derived from TTF in the total emission intensity will be 15/40, i.e., 37.5%.
  • the 75% triplet excitons initially generated collide with each other to generate singlet excitons one singlet exciton is generated from two triplet excitons
  • triplet excitons generated by recombination of holes and electrons in the first light-emitting layer are considered to be difficult to quench at the interface between the first light-emitting layer and the organic layer even if there are excess carriers at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer.
  • the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching due to excess electrons is considered.
  • the first light-emitting layer and the second light-emitting layer so as to satisfy the relationship of the above formula (Mathematical formula 1), triplet excitons generated in the first light-emitting layer can be transferred to the second light-emitting layer without being quenched by excess carriers, and reverse transfer from the second light-emitting layer to the first light-emitting layer can be suppressed.
  • the TTF mechanism is expressed in the second light-emitting layer, singlet excitons are efficiently generated, and the luminous efficiency is improved.
  • a "host material” is a material that is contained in, for example, "50% by mass or more of a layer.”
  • the first light-emitting layer contains the first host material in an amount of 50% by mass or more of the total mass of the first light-emitting layer.
  • the second light-emitting layer contains, for example, the second host material in an amount of 50% by mass or more of the total mass of the second light-emitting layer.
  • both the first light-emitting compound and the second light-emitting compound are compounds according to the first embodiment.
  • the first light-emitting layer contains a first host material and a first light-emitting compound.
  • the first host material is a compound different from the second host material contained in the second light-emitting layer.
  • the first light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.
  • the first light-emitting layer does not contain a metal complex. It is also preferable that the first light-emitting layer does not contain a boron-containing complex in the organic EL element according to this embodiment.
  • the first light-emitting layer preferably does not contain a phosphorescent material (dopant material).
  • the first light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex, for example, an iridium complex, an osmium complex, or a platinum complex.
  • the triplet energy T1 can be measured by the following method.
  • the first benzene ring and the second benzene ring in the biphenyl structure of the condition (i) are further connected by the bridge of the condition (i) at two portions other than the single bond.
  • the linked structure (fused ring) is represented by the following formula (X13).
  • L 12 is a single bond, a substituted or unsubstituted arylene group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 15 ring atoms.
  • L13 is Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms
  • Ar 13 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms
  • mb is 0, 1, 2, 3, 4 or 5;
  • * indicates the bonding position to the benz[a]anthracene ring in the general formula (H13).
  • the compound represented by the general formula (H13) is a compound represented by the following general formula (H132) or (H133).
  • R 150 to R 159 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by —O—(R 904 ), A group represented by -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, A group represented by —C( ⁇ O)R 801 , A group represented by
  • L151 is, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms
  • Ar 151 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mg is 0, 1, 2, 3, 4 or 5;
  • * indicates the bonding position to the pyrene ring in the general formula (H15).
  • R 153 of the compound represented by general formula (H15) is a group represented by general formula (H150).
  • L 151 is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms
  • Ar 151 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • L 151 is a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms
  • Ar 151 is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms.
  • X 15 is an oxygen atom or a sulfur atom
  • L15 is Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, md is 0, 1, 2, 3, 4 or 5;
  • R 1500 to R 1504 are joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
  • R 1500 to R 1504 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent Hydrogen atoms, a substituted or unsubstituted al
  • R 150 to R 152 and R 154 to R 159 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by —O—(R 904 ), A group represented by -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, A group represented by —C( ⁇ O)R
  • md is 0, 1 or 2.
  • the compound represented by general formula (H152) is represented by the following general formula (H153).
  • the first host material is a compound having only one pyrene ring in the molecule (sometimes referred to as a monopyrene compound).
  • the compound represented by general formula (H15) is a monopyrene compound.
  • R 160 to R 169 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl 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
  • the first host material is a compound represented by the following general formula (H162):
  • R 161 to R 167 and R 1601 to R 1604 each independently represent Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, A group represented by -Si(R 901 )(R 902 )(R 903 ), A group represented by —O—(R 904 ), A group represented by -S-(R 905 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, A group represented by —C( ⁇ O
  • mf is 0, 1, or 2.
  • the first host materials are preferably each independently any one of compounds selected from the group consisting of a compound represented by the general formula (H111), a compound represented by the general formula (H122), a compound represented by the general formula (H132), and a compound represented by the general formula (H133).
  • the first host material does not contain a compound having a bis-carbazole structure or a compound having an amine structure.
  • Specific examples of the first host material include the following compounds, however, the present invention is not limited to these specific examples of the first host material.
  • D represents a deuterium atom
  • Me represents a methyl group
  • tBu represents a tert-butyl group
  • Ph represents a phenyl group.
  • the thickness of the first light-emitting layer is preferably 3 nm or more, and more preferably 5 nm or more. If the thickness of the first light-emitting layer is 3 nm or more, the thickness is sufficient to cause recombination of holes and electrons in the first light-emitting layer. In the organic EL element according to this embodiment, the thickness of the first light-emitting layer is preferably 15 nm or less, and more preferably 10 nm or less. If the thickness of the first light-emitting layer is 15 nm or less, the thickness is thin enough for triplet excitons to move to the second light-emitting layer. In the organic EL element according to this embodiment, the thickness of the first light-emitting layer is more preferably 3 nm or more and 15 nm or less.
  • the second light-emitting layer contains a second host material and a second light-emitting compound.
  • the second host material is a compound different from the first host material contained in the first light-emitting layer.
  • the first light-emitting compound and the second light-emitting compound are the same or different from each other.
  • the second light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.
  • the second light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.
  • the second light-emitting layer does not contain a metal complex. It is also preferable that the second light-emitting layer does not contain a boron-containing complex in the organic EL element according to this embodiment.
  • the second light-emitting layer preferably does not contain a phosphorescent material (dopant material).
  • the second light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex, for example, an iridium complex, an osmium complex, or a platinum complex.
  • the second light-emitting compound is preferably contained in the second light-emitting layer in an amount of 0.5% by mass or more. That is, the second light-emitting layer preferably contains the second light-emitting compound in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer, more preferably contains the second light-emitting compound in an amount of 1.0% by mass or more of the total mass of the second light-emitting layer, further preferably contains the second light-emitting compound in an amount of 1.2% by mass or more of the total mass of the second light-emitting layer, and further preferably contains the second light-emitting compound in an amount of 1.5% by mass or more of the total mass of the second light-emitting layer.
  • the organic EL element according to this embodiment includes a third light-emitting layer
  • the triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (H3) of the third host material satisfy the relationship represented by the following mathematical formula (Mathematical Formula 6D).
  • the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact with each other” may include, for example, any of the following embodiments (LS1), (LS2), and (LS3).
  • (LS1) An embodiment in which a region in which both the first host material and the second host material are mixed is generated during the process of vapor-depositing a compound for the first emitting layer and the process of vapor-depositing a compound for the second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.
  • the intervening layer material may be one or both of the first host material contained in the first light-emitting layer and the second host material contained in the second light-emitting layer.
  • the organic EL element according to this embodiment it is preferable to include a hole transport layer between the emission band and the anode. In the organic EL element according to this embodiment, it is preferable to have a hole transport layer disposed between the anode and the emission layer.
  • the second light-emitting layer 52 is a layer disposed closest to the anode side in the emission zone 50B, and the first light-emitting layer 51 is a layer disposed closest to the cathode side in the emission zone 50B.
  • the present invention is not limited to the configuration of the organic EL element shown in FIG. 2 and FIG.
  • Au gold
  • platinum Pt
  • Ni nickel
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • Fe iron
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • nitrides of metal materials e.g., titanium nitride
  • the hole injection layer formed on the anode which is one of the EL layers formed on the anode, is made of a composite material that allows easy hole injection regardless of the work function of the anode, so any material that can be used as an electrode material (e.g., metals, alloys, electrically conductive compounds, and mixtures of these, including other elements belonging to Groups 1 or 2 of the periodic table) can be used.
  • an electrode material e.g., metals, alloys, electrically conductive compounds, and mixtures of these, including other elements belonging to Groups 1 or 2 of the periodic table
  • Materials with small work functions such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these for example, MgAg, AlLi
  • rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • vacuum deposition and sputtering methods can be used.
  • silver paste coating and inkjet methods can be used.
  • cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less).
  • a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs)
  • alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr)
  • alloys containing these e.g., MgAg, AlLi
  • rare earth metals such as euro
  • a vacuum deposition method or a sputtering method can be used.
  • a coating method or an inkjet method can be used.
  • the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.
  • conductive materials can be deposited using a sputtering method, inkjet method, spin coating method, etc.
  • the hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc.
  • substances with high hole injection properties include the low molecular weight organic compounds 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), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD).
  • TDATA 4,
  • aromatic amine compounds include aromatic amine compounds such as [N-(9-phenylcarbazol-3-yl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), as well as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-
  • a polymeric compound oligomer, dendrimer, polymer, etc.
  • polymeric compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino ⁇ phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • PTPDMA poly[N-(4- ⁇ N'-[4-(4-diphenylamino)phenyl]phenyl-N'
  • polymeric compounds to which an acid has been added such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.
  • PEDOT/PSS poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid)
  • PAni/PSS polyaniline/poly(styrenesulfonic acid)
  • aromatic amine compounds examples include aromatic amine compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB).
  • TDATA 4,4',4''-tris(N,N-diphenylamino)triphenylamine
  • MTDATA 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine
  • BSPB 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyla
  • the hole transport layer may be made of carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth.
  • CBP carbazole derivatives
  • CzPA 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene
  • PCzPA 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole
  • anthracene derivatives such as t-BuDNA, DNA, and DPAnth.
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltri
  • an electron transport layer is included between the light emitting layer and the cathode.
  • the electron transport layer is a layer containing a substance with high electron transport properties.
  • a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
  • a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound can be used.
  • a metal complex such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 ), BAlq, Znq, ZnPBO, or ZnBTZ can be used.
  • a benzimidazole compound can be preferably used.
  • the substances described here are mainly substances having an electron mobility of 10 -6 cm 2 /(V ⁇ s) or more. Note that, as long as the substance has a higher electron transporting property than a hole transporting property, a substance other than the above may be used as the electron transporting layer.
  • the electron transporting layer may be formed of a single layer, or may be formed of two or more layers of the above substances stacked together.
  • the electron transport layer can also be made of a polymer compound.
  • a polymer compound for example, 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), etc. can be used.
  • PF-Py poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)]
  • PF-BPy poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)]
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • alkali metals, alkaline earth metals, or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc.
  • a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq, etc. can be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
  • a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used.
  • the electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of such substances include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • each organic layer of the organic EL element is not limited unless otherwise specified above. In general, if the thickness is too thin, defects such as pinholes are likely to occur, and if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the thickness of each organic layer of the organic EL element is usually preferably in the range of several nm to 1 ⁇ m.
  • the electronic device is equipped with the organic electroluminescence element according to any one of the above-mentioned embodiments.
  • the electronic device include a display device and a light-emitting device.
  • the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer.
  • the light-emitting device include lighting and vehicle lamps.
  • the light-emitting device can be used in a display device, for example, as a backlight for a display device.
  • the light-emitting layer is not limited to one layer, and a plurality of light-emitting layers may be laminated.
  • the organic EL element has a plurality of light-emitting layers, it is sufficient that at least one of the organic layers satisfies the conditions described in the above embodiment, and it is preferable that at least one of the light-emitting layers contains the compound of the first embodiment.
  • the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electronic transition from a triplet excited state directly to a ground state.
  • the organic EL element has a plurality of light-emitting layers
  • these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.
  • the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer.
  • a layer e.g., a hole transport layer
  • the organic EL element includes a hole transport layer
  • a barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.).
  • the light emitting layer and the barrier layer are preferably in contact with each other.
  • the specific structure and shape in implementing the present invention may be other structures, etc., as long as the object of the present invention can be achieved.
  • Example 1 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) measuring 25 mm x 75 mm x 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm.
  • the washed glass substrate with transparent electrode lines was attached to a substrate holder of a vacuum deposition apparatus, and the compounds HT-1 and HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm.
  • the proportion of the compound BH-1 in this light-emitting layer was 98% by mass, and the proportion of the compound BD-1 was 2% by mass.
  • a compound ET-1 was deposited by vapor deposition to form a first electron transport layer (sometimes referred to as a hole blocking layer) having a thickness of 10 nm.
  • the compound ET-2 was evaporated to form a second electron transport layer having a thickness of 15 nm.
  • LiF was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
  • Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 80 nm.
  • an organic EL element according to Example 1 was produced.
  • the device configuration of the organic EL element according to Example 1 is roughly shown as follows. ITO(130)/HT-1:HA(10,97%:3%)/HT-1(80)/HT-2(10)/BH-1:BD-1(25,98%:2%)/ET-1(10)/ET-2(15)/LiF(1)/Al(80)
  • the numbers in parentheses indicate film thickness (unit: nm).
  • the numbers in parentheses expressed as percentages (97%:3%) indicate the ratios (unit: mass%) of the compounds HT-1 and HA in the hole injection layer, and the numbers in percentages (98%:2%) indicate the ratios (unit: mass%) of the second compound (compound BH-1) and the first compound (compound BD-1) in the light-emitting layer.
  • percentages 97%:3% indicate the ratios (unit: mass%) of the compounds HT-1 and HA in the hole injection layer
  • the numbers in percentages (98%:2%) indicate the ratios (unit: mass%) of the second compound (compound BH-1) and the first compound (compound BD-1) in the light-emitting layer.
  • the same notations are used hereinafter.
  • Example 2 The organic EL element of Example 2 was produced in the same manner as the organic EL element of Example 1, except that the first compound (compound BD-1) used in forming the light-emitting layer was changed to the first compound (compound BD-2) shown in Table 1.
  • Comparative Example 1 The organic EL element of Comparative Example 1 was produced in the same manner as the organic EL element of Example 1, except that the first compound (compound BD-1) used in forming the light-emitting layer was changed to a comparative compound (compound Ref-1) shown in Table 1.
  • the organic EL elements according to Examples 1, 2, and 3 had a longer life while maintaining the same performance in terms of EQE, ⁇ EL , and FWHM as the organic EL element according to Comparative Example 1.

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  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé représenté par la formule générale (1). Dans la formule générale (1), A1 représente un groupe cyclique hydrocarboné aromatique substitué ou non substitué qui est composé d'un cycle condensé composé de quatre cycles ou plus, ou d'un groupe cyclique hétérocyclique substitué ou non substitué contenant un atome d'azote, un atome d'oxygène ou un atome de soufre en tant que partie du squelette de celui-ci et qui est composé d'un cycle condensé composé de cinq cycles ou plus ; et B1 représente un groupe représenté par la formule générale (10), dans laquelle, lorsque les AkD forment un cycle monocyclique ou un cycle condensé, le cycle monocyclique ou le cycle condensé formé par les AkD contient au moins un atome de deutérium, et les AkD qui ne forment pas un cycle monocyclique ou un cycle condensé représentent chacun indépendamment un groupe alkyle substitué ou non substitué ayant de 1 à 50 atomes de carbone et contenant au moins un atome de deutérium, ou un groupe cycloalkyle substitué ou non substitué ayant de 3 à 50 atomes de carbone formant un cycle et contenant au moins un atome de deutérium.
PCT/JP2023/046254 2023-01-06 2023-12-22 Composé, composition, élément organique électroluminescent et dispositif électronique WO2024147304A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021049889A1 (fr) * 2019-09-10 2021-03-18 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
WO2021150092A1 (fr) * 2020-01-20 2021-07-29 주식회사 엘지화학 Dispositif électroluminescent organique

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021049889A1 (fr) * 2019-09-10 2021-03-18 주식회사 엘지화학 Composé et dispositif électroluminescent organique le comprenant
WO2021150092A1 (fr) * 2020-01-20 2021-07-29 주식회사 엘지화학 Dispositif électroluminescent organique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YING GAO, QING-QING PAN, LIANG ZHAO, YUN GENG, TAN SU, TING GAO, ZHONG-MIN SU: "Realizing performance improvement of blue thermally activated delayed fluorescence molecule DABNA by introducing substituents on the para-position of boron atom", CHEMICAL PHYSICS LETTERS, ELSEVIER BV, NL, vol. 701, 17 April 2018 (2018-04-17), NL , pages 98 - 102, XP055624209, ISSN: 0009-2614, DOI: 10.1016/j.cplett.2018.04.036 *

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