WO2024147321A1 - Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique Download PDF

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WO2024147321A1
WO2024147321A1 PCT/JP2023/046823 JP2023046823W WO2024147321A1 WO 2024147321 A1 WO2024147321 A1 WO 2024147321A1 JP 2023046823 W JP2023046823 W JP 2023046823W WO 2024147321 A1 WO2024147321 A1 WO 2024147321A1
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substituted
group
unsubstituted
ring
bonded
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裕基 中野
良多 高橋
慎太郎 伴
士雄磨 橋本
潔 池田
亮 永田
祐一郎 河村
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出光興産株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H10K85/60—Organic compounds having low molecular weight

Definitions

  • Patent Document 5 discloses an organic EL element that utilizes the triplet-triplet fusion (TTF) mechanism, which is one of the mechanisms of delayed fluorescence.
  • TTF triplet-triplet fusion
  • the TTF mechanism utilizes the phenomenon in which a singlet exciton is generated by the collision of two triplet excitons.
  • an organic electroluminescence element including an anode, a cathode, and an emitting layer disposed between the anode and the cathode, the emitting layer containing a sensitizing material and a fluorescent material, the sensitizing material being a compound according to one aspect of the present invention, and the sensitizing material and the fluorescent material being different compounds.
  • an organic electroluminescence element According to one aspect of the present invention, it is possible to provide a novel compound that can be used in an organic electroluminescence element. According to one aspect of the present invention, it is possible to provide a compound that can cause an organic electroluminescence element to emit light with high efficiency.According to one aspect of the present invention, it is possible to provide a material for an organic electroluminescence element that contains the compound. Accordinging to one aspect of the present invention, it is possible to provide an organic electroluminescence element that emits light with high efficiency, and to provide an electronic device equipped with the organic electroluminescence element.
  • FIG. 1 is a schematic diagram of an apparatus for measuring transient PL.
  • FIG. 13 is a diagram showing an example of a decay curve of a transient PL.
  • FIG. 4 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention.
  • FIG. 11 is a diagram showing the energy levels of a sensitizing material and a fluorescent material in an emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, and the relationship of energy transfer.
  • FIG. 13 is a diagram showing the energy levels of a host material, a sensitizing material, and a fluorescent material in an emitting layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention, and the relationship between energy transfer.
  • FIG. 2 is a diagram showing the energy levels and energy transfer relationship of a host material, a sensitizing material, and a fluorescent material in an example of an emitting layer of an organic electroluminescence device according to another embodiment of the present invention.
  • FIG. 2 is a diagram showing the energy levels and energy transfer relationship of a first host material, a second host material, a sensitizing material, and a fluorescent material in an emitting layer of an example of an organic electroluminescence element according to another embodiment of the present invention.
  • hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.
  • any possible bonding position that is not explicitly indicated with a symbol such as "R” or "D” representing a deuterium atom is assumed to have a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, bonded to it.
  • the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound).
  • a compound having a structure in which atoms are bonded in a ring for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound.
  • the carbon contained in the substituent is not included in the number of ring carbon atoms.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • a 9,9-diphenylfluorenyl group has 13 ring carbon atoms
  • a 9,9'-spirobifluorenyl group has 25 ring carbon atoms.
  • the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring.
  • 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 refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) with a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly).
  • the number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent.
  • the "number of ring atoms" described below is the same unless otherwise specified.
  • the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5.
  • the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6.
  • the number of ring atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
  • the "carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon numbers XX to YY” refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms 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.
  • unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is an "unsubstituted ZZ group”
  • substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group” is a "substituted ZZ group”.
  • unsubstituted in the case of "a substituted or unsubstituted ZZ group” means that a hydrogen atom in the ZZ group is not replaced with a substituent.
  • 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.
  • the "unsubstituted aryl group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted heterocyclic group” described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
  • the "unsubstituted alkyl group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
  • the "unsubstituted cycloalkyl group” described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
  • the "unsubstituted arylene group” described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
  • the number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
  • the "unsubstituted alkylene group” described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B).
  • unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group”
  • substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is a "substituted aryl group”.
  • aryl group simply refers to both an "unsubstituted aryl group” and a "substituted aryl 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).
  • the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group"
  • the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group”.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • the multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
  • the multiple G2s in —Si(G1)(G2)(G2) are the same as or different from each other.
  • the multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
  • G9 A group represented by -S-(R 905 )
  • Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S(G3) and -S(G6)
  • Examples include: here, G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • 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.
  • zadibenzothiophenyl group diazadibenzothiophenyl group
  • (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group)
  • (9-biphenylyl)carbazolyl group (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
  • the (9-phenyl)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.
  • the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group".
  • Specific examples of the "substituted or unsubstituted alkylene group” include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group” described in specific example group G3.
  • Q 1 to Q 10 each independently represent a hydrogen atom or a substituent.
  • * represents a bonding position.
  • 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.
  • the pair of adjacent two that constitutes one group includes the pair of R 921 and R 922 , the pair of R 922 and R 923 , the pair of R 923 and R 924 , the pair of R 924 and R 930 , the pair of R 930 and R 925 , the pair of R 925 and R 926 , the pair of R 926 and R 927 , the pair of R 927 and R 928 , the pair of R 928 and R 929 , and the pair of R 929 and R 921 .
  • one or more pairs means that two or more pairs of the adjacent two or more pairs may simultaneously form a ring.
  • the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).
  • 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, which is 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 ring Q A and the ring Q C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q A and the ring Q C. If the ring Q A in the general formula (TMEP-104) is a benzene ring, the ring Q A is a monocyclic ring. When ring Q 1 A in the above general formula (TMEP-104) is a naphthalene ring, ring Q 1 A is a 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 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 is, for example, the “optional substituent” described later.
  • specific examples of the substituent are the substituents described in the above-mentioned section “Substituents described in this specification”.
  • the substituent is, for example, the “optional substituent” described later.
  • a numerical range expressed using "AA-BB” refers to a range that includes the number AA written before “AA-BB” as the lower limit and the number BB written after "AA-BB” as the upper limit.
  • R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 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, When a plurality of R 901 are present, the plurality of R 901 are the same or different, When a plurality of R 902 are present, the plurality of R 902 are the same or different from each other, When a plurality of
  • a novel compound that can be used in an organic electroluminescence device can be provided. According to one aspect of this embodiment, it is possible to provide a compound that can cause an organic EL device to emit light with high efficiency.
  • n is 2 and m is 2, or n is 1 and m is 3.
  • m, n, D 1 , R 1 , and R 111 to R 114 each independently have the same definition as m, n, D 1 , R 1 , and R 111 to R 114 in formula (1);
  • One or more pairs of adjacent two or more of R 116 to R 119 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 116 to R 119 which do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted fused ring each independently have the same meaning as R 115 in formula (1).
  • any pair of adjacent two or more of R 11A to R 15A are not bonded to each other, any pair of adjacent two or more of R 11 to R 14 is not bonded to each other; any pair of adjacent R 101 is not bonded to each other; The pair consisting of R 15B and R 15C are not bonded to each other; any pair of adjacent two or more of R 21 to R 24 are not bonded to each other; It is preferred that any pair of adjacent two or more R29s among the plurality of R29s are not bonded to each other.
  • the group represented by the general formula (1A) is preferably a group represented by any one of the general formulas (13) to (18).
  • X 1 is preferably a single bond.
  • R 11 to R 14 , R 21 to R 24 , R 29 , R 101 , R 11A to R 15A , R 15B , R 15C , R D1 , R D2 , R D3 , R D4 , R D5 , R D6 , R D12 , R D13 , R D14 and R D15 are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 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, and more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted
  • the compound represented by the general formula (1) is preferably a compound represented by any one of the following general formulas (H21) to (H27).
  • R 904 when R 904 is a hydrogen atom, the group represented by —O—(R 904 ) is a hydroxy group.
  • the group represented by -S-(R 905 ) is a thiol group when R 905 is a hydrogen atom.
  • the group represented by --Ge(R 933 )(R 934 )(R 935 ) is a substituted germanium group when R 933 , R 934 and R 935 are substituents.
  • R 936 and R 937 when R 936 and R 937 are substituents, the group represented by -B(R 936 )(R 937 ) is a substituted boryl group.
  • Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it, and measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped.
  • the PL emission of a TADF compound is as follows: The emission is classified into two types: emission from singlet excitons generated by the first PL excitation, and emission from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from the singlet excitons decays quickly after irradiation with a pulsed laser.
  • the transient PL measurement device 100 in FIG. 1 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image.
  • a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength
  • a sample chamber 102 for accommodating a measurement sample
  • a spectroscope 103 for dispersing the light emitted from the measurement sample
  • a streak camera 104 for forming a two-dimensional image
  • a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG. 1.
  • the sample contained in the sample chamber 102 is obtained by forming a thin film of a matrix material doped with a doping material at a concentration of 12% by mass on a quartz substrate.
  • transient PL measurement it is possible to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, it is possible to estimate the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state.
  • the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly is relatively large.
  • Prompt emission is emission that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength that the delayed fluorescent material absorbs.
  • Delay emission is emission that is not observed immediately after excitation by the pulsed light, but is observed at a later time.
  • the amount and ratio of Prompt and Delay luminescence can be calculated by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of Prompt and Delay luminescence is not limited to the device described in Reference 1 or the device shown in Figure 1.
  • the compound according to the present embodiment is a delayed fluorescent compound
  • a sample prepared by the following method is used to measure the delayed fluorescence of the delayed fluorescent compound.
  • the delayed fluorescent compound according to the present embodiment is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption.
  • the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
  • the amount of prompt luminescence (immediate luminescence) of the compound to be measured is designated as XP and the amount of delay luminescence (delayed luminescence) is designated as XD
  • the value of XD / XP is 0.05 or more.
  • the amounts and ratio of prompt luminescence and delay luminescence of compounds other than the delayed fluorescent compound in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delay luminescence of the delayed fluorescent compound according to this embodiment.
  • the difference ⁇ ST(GT2) between the lowest excited singlet energy S 1 (GT2) of the delayed fluorescent compound and the energy gap T 77K (GT2) at 77 [K] of the delayed fluorescent compound is preferably less than 0.5 eV, more preferably less than 0.3 eV, even more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, it is preferable that ⁇ ST(GT2) satisfies the following formula (Math 2), (Math 2A), (Math 2B), (Math 2C) or (Math 2D).
  • the energy gap at 77 K differs from the triplet energy that is usually defined.
  • the triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube.
  • the spectrum measured in the same manner as above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish which state the light emission is from, but the triplet energy value is basically considered to be dominant. Therefore, in this embodiment, the measurement method is the same as that of the normal triplet energy T, but in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T 77K .
  • a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the energy amount calculated from the following conversion formula (F1) based on the wavelength value ⁇ edge [nm] of the intersection point between the tangent and the horizontal axis is defined as the energy gap T 77K at 77 [K].
  • Conversion formula (F1): T 77K [eV] 1239.85 / ⁇ edge
  • the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows.
  • the slope of this tangent increases as the curve rises (i.e., as the vertical axis increases).
  • the tangent drawn at the point where this slope is at its maximum is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and a tangent drawn at a point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as a tangent to the rising edge on the short wavelength side of the phosphorescence spectrum.
  • Phosphorescence can be measured using a spectrofluorophotometer body, Model F-4500, manufactured by Hitachi High-Technologies Corp.
  • the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.
  • the tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows.
  • the slope of this tangent decreases and then increases repeatedly.
  • the tangent drawn at the point where the slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values of 0.2 or less are not included in the maximum values on the longest wavelength side.
  • the compound according to this embodiment (the compound represented by the general formula (1)) can be produced by a known method.
  • the compound according to this embodiment can be produced according to the synthesis method described in the examples described later, or by following the synthesis method and using known alternative reactions and raw materials suited to the target product.
  • 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 light-emitting layer contains a sensitizing material and a fluorescent material.
  • the sensitizing material is the compound according to the first embodiment.
  • recombination of holes and electrons is likely to occur on the molecules of the sensitizing material, not on the fluorescent material, and when the sensitizing material is a delayed fluorescent compound, it is considered that reverse intersystem crossing occurs from the lowest excited triplet state to the lowest excited singlet state. In this way, after the transition of the energy state to the lowest excited singlet state occurs in the sensitizing material, energy transfer occurs from the sensitizing material to the fluorescent material, and fluorescent emission occurs from the lowest excited singlet state of the fluorescent material.
  • a hole transport layer may be disposed between the anode and the light-emitting layer.
  • the sensitizing material and the fluorescent material are contained in a single layer.
  • the sensitizing material and the fluorescent material are contained in the single light-emitting layer, and when the organic EL element has multiple light-emitting layers, the sensitizing material and the fluorescent material are contained in any one of the multiple light-emitting layers.
  • the fluorescent material is preferably a compound that does not exhibit thermally activated delayed fluorescence.
  • the fluorescent material is not a phosphorescent metal complex.
  • the fluorescent material is preferably not a metal complex.
  • the compound used as the fluorescent material may be referred to as a third compound.
  • examples of the third compound include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivative
  • the fluorescent material is preferably one or more compounds selected from the group consisting of third compounds represented by the following general formula (41):
  • the compound represented by the general formula (41) is preferably a compound represented by the following general formula (410):
  • the compound represented by the general formula (41) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (41-1) to (41-6):
  • Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 ; a pair of R 401 and R 421 , a pair of two or more adjacent ones of R 421 to R 423 , one or more pairs selected from the group consisting of a pair of R 423 and R 402 , a pair of R 402 and R 424 , a pair of two or more adjacent ones of R 424 to R 427 , a pair of R 427 and R 412 , and a pair of R 412 and R 411 , 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 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent
  • Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 424 , a pair of two or more adjacent pairs of R 424 to R 427 , a pair of R 413 and R 414 , and a pair of R 414 and R 401 , 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 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent
  • Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 415 and R 416 , a pair of R 416 and R 412 , and a pair of R 412 and R 411 , 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 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent a substituted or unsubstituted alkyl
  • Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 418 , a pair of R 418 and R 417 , and a pair of R 412 and R 411 , 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 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring are each independently a substituted or unsubstituted alkyl
  • Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ), or NR 405 ; one or more pairs selected from the group consisting of a pair of R 401 and R 421 , a pair of two or more adjacent pairs of R 421 to R 423 , a pair of R 423 and R 402 , a pair of R 402 and R 418 , a pair of R 418 and R 417 , a pair of R 413 and R 414 , and a pair of R 414 and R 401 , 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 401 and R 402 which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted fused ring each independently represent
  • one or more pairs selected from the group consisting of a pair of R 412 and R 411 , a pair of R 413 and R 414 , a pair of R 415 and R 416 , and a pair of R 417 and R 418 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring.
  • the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-1):
  • R 421 to R 431 are the same as R 421 to R 431 in the general formula (41-6), respectively.
  • One or more pairs of adjacent two or more of R 451 to R 455 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.
  • One or more pairs of adjacent two or more of R 456 to R 460 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 451 to R 455 and R 456 to R 460 which do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted condensed ring, are each independently a hydrogen atom or a substituent R X , and the substitution of R
  • Specific examples of compounds represented by formula (41) include the compounds shown below. In the specific examples, Me represents a methyl group, tBu represents a tertiary butyl group, and Ph represents a phenyl group.
  • the fluorescent material is preferably one or more compounds selected from the group consisting of third compounds represented by the following general formula (31) or (32).
  • the third compound as the fluorescent material may be a compound represented by the following general formula (31) or a compound represented by the following general formula (32).
  • the C1 ring and the D1 ring are either bonded to each other by a single bond, bonded to each other via O, S, NR 33 , Si(R 34 )(R 35 ), or C(R 37 )(R 38 ), or not bonded to each other;
  • the substituents of R E or R E are bonding with at least one of the A1 ring, the substituent of the A1 ring, the B1 ring and
  • Ring A2 , ring B2 and ring C2 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms
  • Ring D2 is a substituted or unsubstituted monocyclic ring having 5 to 7 ring atoms which may be condensed with at least one substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms, the C2 ring and the D2 ring are condensed to each other via a single bond or a double bond;
  • Ring A2 and ring D2 are either bonded to each other by a single bond, bonded to each other via O, S, NR 33 , Si(R 34 )(R 35 ), or C(R 37 )(R 38 ), or not bonded to each other;
  • the substituents of R F or R F are or forming
  • R E which is not bonded to the A1 ring, the substituent of the A1 ring, the B1 ring, and the substituent of the B1 ring, and R F which is not bonded to the A2 ring, the substituent of the A2 ring, the B2 ring, and the substituent of the B2 ring each independently represent: Hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring 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 substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, an iminyl group represented by -CR 39 ⁇ N, or a substituted or
  • the compound represented by the general formula (31) is also preferably a compound represented by the following general formula (35):
  • one or more of a group consisting of two or more adjacent groups among R 1 to R 3 , a group consisting of two or more adjacent groups among R 4 to R 6 , a group consisting of two or more adjacent groups among R 12 to R 15 , and a group consisting of two or more adjacent groups among R 16 to R 19 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,
  • One or more pairs of adjacent two or more of R 7 to R 11 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
  • the pair of R 7 and R 6 is joined together to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a
  • the compound represented by the general formula (31) is any compound selected from the group consisting of compounds represented by the following general formulae (351), (352), and (353).
  • one or more of a group consisting of two or more adjacent members of R 1 to R 3 , a group consisting of R 4 and R 5 , a group consisting of two or more adjacent members of R 8 to R 11 , a group consisting of two or more adjacent members of R 12 to R 15 , and a group consisting of two or more adjacent members of R 16 to R 19 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 1 to R 5 and R 8 to R 19 which do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring each independently have the same meaning as R 1 to R 5 and R 8 to R 19 in formula (35).
  • one or more of a group consisting of two or more adjacent groups among R 1 to R 3 , a group consisting of two or more adjacent groups among R 4 to R 6 , a group consisting of two or more adjacent groups among R 7 to R 10 , a group consisting of two or more adjacent groups among R 13 to R 15 , and a group consisting of two or more adjacent groups among R 16 to R 19 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 1 to R 10 and R 13 to R 19 which do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring each independently have the same meaning as R 1 to R 10 and R 13 to R 19 in formula (35).
  • the compound represented by the general formula (31) can be produced by a known method.
  • the compound represented by the general formula (31) can also be produced by following a known method and using known alternative reactions and raw materials suited to the target product.
  • Specific examples of compounds represented by formula (31) include the compounds shown below.
  • the substituent in the "substituted or unsubstituted" case in the third compound is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901a )(R 902a )(R 903a ), -O-(R 904a ), -S-(R 905a ), -N(R 906a )(R 907a ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms; R 901a to R 907a
  • the substituent in the "substituted or unsubstituted" third compound is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the "substituted or unsubstituted" third compound is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.
  • the maximum peak wavelength of the third compound as the fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less.
  • the maximum peak wavelength of the third compound as the fluorescent material is preferably 430 nm or more, and more preferably 440 nm or more.
  • the maximum peak wavelength of fluorescent emission may be referred to as the maximum peak wavelength of fluorescent emission.
  • the third compound preferably emits blue light.
  • blue light emission refers to light emission having a maximum peak wavelength in the fluorescent spectrum in the range of 430 nm to 480 nm.
  • the emission spectrum half width FWHM of the third compound as the fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less.
  • the maximum fluorescence emission peak wavelength refers to the maximum peak wavelength of the fluorescence spectrum at which the emission intensity in the measured fluorescence spectrum is maximum 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 emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the fluorescence spectrum.
  • a fluorescence spectrum measuring device can be used as a device for measuring the fluorescence spectrum.
  • a fluorescence spectrum measuring device (device name: FP-8300) manufactured by JASCO Corporation can be used. Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.
  • the Stokes shift of the third compound as the fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less.
  • the Stokes shift of the third compound as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more.
  • the excitation energy can be reduced.
  • the third compound has a Stokes shift of 10 nm or more, self-absorption can be suppressed and loss of efficiency can be reduced.
  • the Stokes shift can be measured by the following method. The compound to be measured is dissolved in toluene at a concentration of 2.0 ⁇ 10 ⁇ 5 mol/L to prepare a measurement sample.
  • the measurement sample placed in a quartz cell is irradiated with continuous light in the ultraviolet-visible region at room temperature (300K) to measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength).
  • a spectrophotometer can be used to measure the absorption spectrum, for example, a spectrophotometer U-3900/3900H model from Hitachi High-Tech Science Corporation can be used.
  • the compound to be measured is dissolved in toluene at a concentration of 4.9 ⁇ 10 ⁇ 6 mol/L to prepare a measurement sample.
  • the measurement sample placed in a quartz cell is irradiated with excitation light at room temperature (300K) to measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength).
  • a spectrophotometer can be used to measure the fluorescence spectrum, for example, a spectrofluorometer F-7000 model from Hitachi High-Tech Science Corporation can be used. From these absorption and fluorescence spectra, the difference between the maximum absorption wavelength and the maximum fluorescence wavelength is calculated to determine the Stokes shift (SS), which is expressed in nm.
  • SS Stokes shift
  • the sensitizing material (the compound according to the first embodiment) is the delayed fluorescent compound.
  • the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, and may not contain a phosphorescent metal complex.
  • FIG. 4 is a diagram showing an example of the relationship between the energy levels of a sensitizing material and a fluorescent material when the light-emitting layer contains a delayed fluorescent compound (second compound) as a sensitizing material and a fluorescent material (third compound).
  • S0 represents the ground state.
  • S1 (M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1 (M2) represents the lowest excited triplet state of the delayed fluorescent compound.
  • S1 (M3) represents the lowest excited singlet state of the fluorescent material, and T1 (M3) represents the lowest excited triplet state of the fluorescent material.
  • 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
  • the organic EL element according to this embodiment may be a bottom-emission type organic EL element, or a top-emission type organic EL element.
  • the organic EL element is of a bottom emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection.
  • the organic EL element is of a top emission type, it is preferable that the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmittance.
  • the organic EL device When the organic EL device is of a top-emission type, the organic EL device usually includes a capping layer on the top of the cathode.
  • the capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide).
  • the capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives.
  • a laminate in which layers containing these substances are laminated can also be used as the capping layer.
  • 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 a carbazole derivative such as CBP, CzPA, or PCzPA, or an anthracene derivative such as t-BuDNA, DNA, or DPAnth.
  • a carbazole derivative such as CBP, CzPA, or PCzPA
  • an anthracene derivative such as t-BuDNA, DNA, or DPAnth.
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) or poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly(4-vinyltriphenylamine)
  • other substances may be used as long as they have a higher hole transporting property than an electron transporting property.
  • the layer containing the substance having a high hole transporting property may be a single layer or a layer in which two or more layers made of the above-menti
  • 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.
  • the host material, the sensitizing material, and the fluorescent material are contained in a single layer.
  • the host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer
  • the organic EL element has multiple light-emitting layers
  • the host material, the sensitizing material, and the fluorescent material are contained in any one of the multiple light-emitting layers.
  • R 13 to R 19 in X 10 and R 13 to R 19 in X 9 are each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms.
  • R 13 to R 19 in X 10 and R 13 to R 19 in X 9 are each independently an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.
  • R 110 and R 112 to R 114 each independently have the same meaning as R 11 in the general formula (101), provided that at least one of R 110 and R 112 to R 114 is a single bond bonding to another atom or another structure in the molecule of the first compound, and a plurality of R 110 are the same or different from each other.
  • a pair of two or more adjacent R 110s among the plurality of R 110s, and one or more pairs of R 112 and R 113 are bonded to each other to form a substituted or unsubstituted monocycle, or a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 110 each independently has the same meaning as R 11 in the general formula (101), provided that at least one of R 110 is a single bond bonding to another atom or another structure in the molecule of the first compound, and a plurality of R 110 are the same or different from each other.
  • one or more pairs of adjacent two or more of the plurality of R 110 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 114 and R 121 to R 131 each independently have the same meaning as R 12 in the general formula (102), provided that at least one of R 114 and R 121 to R 131 is a single bond bonding to another atom or another structure in the molecule of the first compound.
  • one or more pairs of R 122 and R 123 , R 123 and R 114 , and R 114 and R 121 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • one or more pairs of R 124 and R 125 , R 125 and R 126 , R 126 and R 127 , R 127 and R 128 , and R 128 and R 129 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • one or more of a pair of R 124 and R 125 , a pair of R 125 and R 126 , a pair of R 126 and R 127 , a pair of R 127 and R 128 , a pair of R 128 and R 129 , a pair of R 129 and R 114 , and a pair of R 114 and R 124 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • one or more pairs of R 124 and R 125 , R 125 and R 126 , R 130 and R 131 , and R 131 and R 129 are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • a pair of two or more adjacent R 110s among the plurality of R 110s, and one or more pairs of R 132 and R 133 are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 110 is each independently the same as R 12 in the general formula (102), Xa and Xb are each independently the same as X 10 in the general formula (102), with the proviso that at least one of R 110 is a single bond bonding to another atom or another structure in the molecule of the first compound, or at least one of the nitrogen atom, carbon atom and silicon atom in Xa and Xb is bonded to another atom or another structure in the molecule of the first compound, and a plurality of R 110 are the same or different from each other.
  • R 110 is each independently the same as R 12 in the general formula (102), and Xa, Xb, and Xc are each independently the same as X 10 in the general formula (102), with the proviso that at least one of R 110 is a single bond bonding to another atom or another structure in the molecule of the first compound, or at least one of the nitrogen atom, carbon atom, and silicon atom in Xa, Xb, and Xc is bonded to another atom or another structure in the molecule of the first compound, and a plurality of R 110 are the same or different from each other.
  • a pair of two or more adjacent R 110s , a pair of R 14 and R 15 in Xa, Xb, and Xc (same meaning as the pair of R 14 and R 15 in X10 ), and one or more pairs of R 16 and R 17 in Xa, Xb, and Xc (same meaning as the pair of R 16 and R 17 in X10 ) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.
  • R 110 , R 101 to R 106 , R 112 to R 114 , R 121 to R 131 and R 132 to R 135 each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon
  • R 13 to R 19 (same definition as R 13 to R 19 in X 10 ) in Xa, Xb, Xc and X 110 each preferably independently represents a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atom
  • the first compound preferably has at least one of (I) a cyano group, an amino group, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, or (II) at least one monovalent or higher residue derived from any of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubsti
  • the first compound (III) has at least one cyano group, or (IV) has at least one monovalent or higher residue derived from any of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.
  • the first compound has at least one monovalent or higher residue derived from any one of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, and substituted or unsubstituted pyrimidine.
  • the first compound preferably has at least one monovalent or higher residue derived from a substituted or unsubstituted carbazole.
  • the first compound has at least one partial structure represented by the following general formula (15).
  • R 150 to R 158 is a single bond bonding to another atom or another structure in the molecule of the first compound, R 150 to R 158 which are not single bonds each independently represent a hydrogen atom; 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 group represented by -N(R
  • R 150 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and even more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the first compound is also preferably a compound represented by the following general formula (161) or the following general formula (162).
  • Ar 161 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, m1 is 1, 2, 3, 4, 5 or 6; R 161 is an electron donating group, and R 161 is bonded to an element constituting Ar 161 , When m1 is 2 or more, each of R 161 is the same or different, However, Ar 161 is not an electron-accepting aromatic hydrocarbon ring or heterocycle, and when Ar 161 has a substituent, the substituent is not an electron-accepting group, In the general formula (162), Ar 162 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, n1 is 1, 2, 3, 4, 5 or 6; R 162 is an electron accepting group, and
  • Ar 161 and Ar 162 are each independently a monovalent or higher residue derived from any of the compounds represented by the following general formulae (A61), (A62) and (A63).
  • R 1 D when R 1 D is a substituent, examples of the substituent include the same groups as R 11 in the formula (101).
  • R 161 in the general formula (161) is preferably each independently a monovalent or higher residue derived from any of the compounds represented by the following general formulae (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following general formula (DN7).
  • R 162 in the general formula (162) is preferably each independently a monovalent or higher residue derived from any of the compounds represented by the following general formulae (AC4) to (AC18), and (AC22) to (AC23), or any of the groups represented by the following general formulae (AC1) to (AC3), (AC19) to (AC21), and (AC24).
  • nA is 1, 2 or 3
  • X 1 to X 8 are each independently CR 163 or a carbon atom bonded to another atom or another structure in the molecule of the first compound, provided that at least one of the carbon atoms in X 1 to X 8 is bonded to an element constituting Ar 162
  • X 1 to X 8 each independently represent a nitrogen atom or CR 163 , or a carbon atom bonded to an element constituting Ar 162
  • the plurality of R 163 when a plurality of R 163 are present, the plurality of R 163 are the same or different from each other, and one or more pairs of adjacent two or more of the plurality of R 163 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,
  • X13 is an oxygen atom, a sulfur atom, or a group represented by N-Rb;
  • Z 1 to Z 12 each independently represent a nitrogen atom or a group represented by C—Rc;
  • Ar 14 and Ar 15 each independently represent 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,
  • L 14 and L 15 each independently represent 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
  • Rb and Rc 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 unsub
  • Ar 11 and Ar 12 each independently represent 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
  • L 11 and L 12 each independently represent 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
  • L13 is a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring atoms
  • m is 0, 1, 2, or 3
  • L 13 are the same or different
  • X 1 to X 8 and Y 1 to Y 8 each independently represent N or CRa; provided that one of X 5 to X 8 and one of Y 1 to Y 4 are
  • At least one of X 1 to X 4 and Y 5 to Y 8 is CRa, and at least one of Ra in X 1 to X 4 and Y 5 to Y 8 is an aryl group having 6 to 50 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted with a cyano group.
  • Ar 11 , Ar 12 , L 11 , L 12 , L 13 , m, X 1 to X 5 , X 7 to X 8 , Y 1 to Y 2 and Y 4 to Y 8 each represent a group represented by the general formula (12).
  • Ar 11 , Ar 12 , L 11 , L 12 , L 13 , m, X 1 to X 5 , X 7 to X 8 , Y 1 to Y 2 and Y 4 to Y 8 are the same as those in the above formula (121), and the compound represented by the general formula (121) satisfies at least one of the conditions (i) and (ii).
  • the group represented by -Ar 11 -L 11 and the group represented by -Ar 12 -L 12 are different from each other.
  • the light-emitting layer may contain two or more first compounds having different molecular structures.
  • first compounds having different molecular structures.
  • the charge balance in the light-emitting layer is improved, and it is expected that the light-emitting efficiency will be improved.
  • the excitation energy is reduced, and it becomes possible to drive the device at a lower voltage than when a single host material is contained in the light-emitting layer.
  • FIG. 5 is a diagram showing an example of the relationship between the energy levels of the host material, the sensitizing material, and the fluorescent material when the light-emitting layer contains a host material (first compound), a delayed fluorescent compound (second compound) as a sensitizing material, and a fluorescent material (third compound).
  • S0 represents the ground state.
  • S1 (M1) represents the lowest excited singlet state of the host material
  • T1 (M1) represents the lowest excited triplet state of the host material.
  • S1 (M2) represents the lowest excited singlet state of the delayed fluorescent compound
  • T1 (M2) represents the lowest excited triplet state of the delayed fluorescent compound.
  • the energy gap T 77K (H1) at 77 [K] of the host material and the energy gap T 77K (G2) at 77 [K] of the sensitizing material satisfy the relationship of the following mathematical formula (Mathematical Formula 1). T 77K (H1)>T 77K (G2) ... (Equation 1)
  • the minimum excited singlet energy S 1 (H1) of the host material and the minimum excited singlet energy S 1 (GT2) of the sensitizing material satisfy the relationship of the following mathematical formula (Mathematical Formula 4A). S1 (H1)> S1 (GT2) ... (Equation 4A)
  • the minimum excited singlet energy S 1 of the host material, the sensitizing material, and the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical Formula 4B).
  • the energy gaps T 77K at 77 [K] of the host material, the sensitizing material, and the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical Formula 6B).
  • the contents of the host material (first compound), the sensitizing material (second compound), and the fluorescent material (third compound) contained in the light-emitting layer are preferably within the following ranges, for example.
  • the content of the host material (first compound) in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more.
  • the content of the host material (first compound) in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.
  • the content of the sensitizing material (second compound) is preferably 5% by mass or more, and more preferably 10% by mass or more.
  • the content of the sensitizing material (second compound) is preferably 50% by mass or less, and more preferably 30% by mass or less.
  • the light-emitting layer contains the compound according to the first embodiment (second compound), and therefore, according to the third embodiment, high efficiency of the organic EL element can be achieved.
  • the organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • the electronic device according to the fifth embodiment is equipped with the organic EL element according to any of the above-mentioned embodiments.
  • the electronic device according to the fifth embodiment may be equipped with the organic EL element according to any of the other embodiments described below.
  • Examples of the electronic device include a display device and a light-emitting device.
  • Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer.
  • Examples of the light-emitting device include lighting and vehicle lamps.
  • the light-emitting device can be used in a display device, and can also be used as a backlight for a display device, for example.
  • An organic EL element includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode.
  • the emitting layer may include the compound according to the first embodiment (the compound represented by the general formula (1)) as a host material, and a phosphorescent metal complex as a dopant material.
  • FIG. 7 is a diagram showing an example of the relationship between the energy levels of a first host material (first compound), a second host material (fourth compound), a phosphorescent metal complex (second compound) as a sensitizing material, and a fluorescent material (third compound) in an emitting layer.
  • S0 represents the ground state.
  • S1(M1) represents the lowest excited singlet state of the first host material
  • T1(M1) represents the lowest excited triplet state of the first host material.
  • S1(M4) represents the lowest excited singlet state of the second host material
  • T1(M4) represents the lowest excited triplet state of the second host material.
  • the lowest excited singlet state S1 (M2) of the phosphorescent metal complex can undergo intersystem crossing to the lowest excited triplet state T1 (M2) due to spin-orbit interaction and heavy atom effect. Then, dipole-type energy transfer occurs from the lowest excited triplet state T1 (M2) of the phosphorescent metal complex to the fluorescent material, generating the lowest excited singlet state S1 (M3). As a result, fluorescence from the lowest excited singlet state S1 (M3) of the fluorescent material can be observed. It is believed that the internal quantum efficiency can be theoretically increased to 100% by utilizing this mechanism as well.
  • the magnitude relationship between the energy levels of S1 (M1) and S1 (M4) and the magnitude relationship between the energy levels of T1 (M1) and T1 (M4) are not limited to those shown in FIG.
  • the phosphorescent metal complex preferably comprises a heavy metal atom.
  • the phosphorescent metal complex preferably contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).
  • the phosphorescent metal complex is preferably a compound represented by the following general formula (21). M( L1 ) n1 ( L2 ) n2 ... (21)
  • M is a transition metal selected from the group consisting of first transition metals, second transition metals, and tertiary transition metals;
  • L1 is at least one ligand selected from the group consisting of a ligand represented by the general formula (211), a ligand represented by the general formula (212), and a ligand represented by the general formula (213),
  • n1 is 1, 2 or 3;
  • L2 is at least one ligand selected from the group consisting of monodentate ligands, bidentate ligands and tridentate ligands;
  • n2 is 0, 1, 2, 3 or 4;
  • ring CY1 , ring CY2 , ring CY3 and ring CY4 are each independently selected from the group consisting of a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms;
  • Y 1 to Y 4 each independently represent Single bond, Double bonds,
  • a carbocyclic group having 5 to 30 ring carbon atoms means a monocyclic or polycyclic group having 5 to 30 carbon atoms that contains only carbon as a ring atom.
  • the carbocyclic group having 5 to 30 ring carbon atoms may be an aromatic carbocyclic group or a non-aromatic carbocyclic group.
  • the carbocyclic group having 5 to 30 ring carbon atoms may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group.
  • the carbocyclic group having 5 to 30 ring carbon atoms being a trivalent group or a tetravalent group.
  • a heterocyclic group having 1 to 30 ring carbon atoms means a group that has the same structure as a carbocyclic group having 5 to 30 ring carbon atoms, but contains at least one heteroatom selected from N (carbon atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom) and S (sulfur atom) as a ring-forming atom in addition to carbon (which may have a carbon number of 1 to 30).
  • a heterocycloalkyl group having 3 to 50 ring atoms means a monovalent monocyclic group having 3 to 50 ring atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and specific examples include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.
  • a heterocycloalkylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkyl group having 3 to 50 ring atoms.
  • a heterocycloalkenyl group having 3 to 50 ring atoms is a monovalent monocyclic group having 3 to 50 ring atoms that contains at least one heteroatom selected from N, O, Si, P, and S as a ring atom and has at least one double bond within the ring.
  • Specific examples of heterocycloalkenyl groups having 3 to 50 ring atoms include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothiophenyl groups.
  • a heterocycloalkenylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring atoms.
  • the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms
  • the substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms
  • the substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms
  • the substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms.
  • a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed together, the ring atoms are carbon only, and the entire molecule has non-aromaticity.
  • a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.
  • a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed together and which contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom other than carbon, and in which the entire molecule is non-aromatic.
  • a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
  • terphenylyl group means a "phenyl group substituted with a biphenylyl group.”
  • the “terphenylyl group” belongs to the "substituted phenyl group” whose substituent is an "aryl group having 6 to 50 ring carbon atoms substituted with an aryl group having 6 to 50 ring carbon atoms.”
  • M is preferably one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm), and is more preferably platinum (Pt) or iridium (Ir).
  • Y 1 to Y 4 in general formulae (211) to (213) may each independently be at least one selected from the group consisting of a single bond, a double bond, *a-O-*b, *a-S-*b, *a-C(R 5 )(R 6 )-*b, and *a-N(R 5 )-*b.
  • the electron donating group may be an iso-propyl group, a tert-butyl group, or a substituent selected from the group consisting of the following general formulae (10-1) to (10-61):
  • deuterium atoms are represented as D in chemical formulas, and protium atoms are represented as H or are omitted.
  • methyl groups may be represented as Me, phenyl groups as Ph, isopropyl groups as i-Pr, and t-butyl groups as t-Bu in chemical formulas.
  • At least one of R 1 to R 4 in the general formula (213) is a substituent other than hydrogen, and/or at least one of Y 1 to Y 4 is *a-N(R 5 )-*b, and R 5 may be a substituted aryl group having 6 to 50 ring carbon atoms.
  • Example 6 An organic EL element according to Example 6 was produced.
  • the device configuration of the organic EL element according to Example 6 is roughly shown as follows. ITO(130)/HT-3:HA(10,97%:3%)/HT-3(60)/EBL-2(5)/STZ-1:h-host-1:PD-1:BD-2(30,43.9%:43.9%:11%:1.2%)/STZ-1(5)/ET-2:Liq(30,50%,50%)/LiF(1)/Al(50)
  • the numbers in parentheses indicate the film thickness (unit: nm).

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Abstract

Ce composé est représenté par la formule générale (1) et comprend au moins deux groupes donneurs d'électrons par molécule. Dans la formule générale (1), CN est un groupe cyano, n est 1, 2 ou 3, m est 1, 2 ou 3, n + m = 4, et D1 est un groupe représenté par la formule générale (1A), où lorsque n est 1, le groupe représenté par la formule générale (1A) a deux groupes donneurs d'électrons ou plus dans le groupe. Dans la formule générale (1A), LD est une liaison simple ou un groupe de liaison, et D1A est un groupe donneur d'électrons.
PCT/JP2023/046823 2023-01-06 2023-12-26 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique WO2024147321A1 (fr)

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