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WO2021095729A1 - Composé hétérocyclique à teneur en azote possédant un groupe perfluoroalkyle, et application de celui-ci - Google Patents

Composé hétérocyclique à teneur en azote possédant un groupe perfluoroalkyle, et application de celui-ci Download PDF

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WO2021095729A1
WO2021095729A1 PCT/JP2020/041917 JP2020041917W WO2021095729A1 WO 2021095729 A1 WO2021095729 A1 WO 2021095729A1 JP 2020041917 W JP2020041917 W JP 2020041917W WO 2021095729 A1 WO2021095729 A1 WO 2021095729A1
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group
ring
compound
rings
perfluoroalkyl
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WO2021095729A9 (fr
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横山　正幸
夏輝 伊藤
大地 東山
芳裕 内田
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Toyobo Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • a nitrogen-containing heterocyclic compound having a perfluoroalkyl group and a technique related to its utilization are disclosed.
  • OLEDs organic light emitting diodes
  • As the light emitting material it is required that various characteristics such as light emitting color (light emitting maximum wavelength), light emitting efficiency (light emitting quantum yield), and excited state stability (durability) are preferable.
  • TADF Thermally Activated Delayed Fluorescence
  • next-generation light emitting materials because they show high luminous efficiency even though they are pure organic substances.
  • Patent Document 1 describes that a compound having a carbazole ring represented by the following formula has high luminous efficiency.
  • Patent Document 2 describes that a compound having a carbazole ring having a perfluoroalkyl group represented by the following formula has high luminous efficiency.
  • the present inventors have substituted compounds having a trifluoromethyl group in all carbazole rings (compounds described in Patent Document 2) and compounds having the same skeleton in which trifluoromethyl groups have not been substituted in carbazole rings (Patent Documents). It has been found that the compound described in 1) has a problem that the emission wavelength sometimes reaches the ultraviolet region and includes light emission that adversely affects the human body known as blue light.
  • one object of the present invention is to provide a nitrogen-containing heterocyclic compound having a perfluoroalkyl group having a suitable emission wavelength, and a technique relating to its use.
  • N is an integer of 2 or more
  • Q is a single bond or -CH 2- .
  • N is an integer of 2 or more
  • two adjacent rings X are linked by either (A) direct linking, (B) linking via a ⁇ -conjugated linking group, or (C) condensation linking. If the total number of perfluoroalkyl groups substituted with N rings X is 1 or more and less than 2N, the total number of perfluoroalkyl groups substituted with N rings X is 0. Alternatively, it has been found that the emission wavelength is longer than that of the compound having the same structure except that the number is 2N, and the compound has a suitable emission wavelength. The present invention has been further studied and completed based on this finding.
  • the present invention includes the following aspects.
  • Item 1 Expression (X) of N (N is an integer of 2 or more): (In the equation, Q is a single bond or -CH 2- .) A compound having a ring X represented by, in which two adjacent rings X are linked by either (A) direct linking, (B) linking via a ⁇ -conjugated linking group, or (C) condensation linking. Compounds in which the total number of perfluoroalkyl groups that are linked and substituted with N rings X is 1 or more and less than 2N [However, the following compounds: (In the formula, Y is a cyano group or a perfluoromethyl group.) except for].
  • Q 11 ⁇ Q 13 are each independently a single bond or -CH 2 -
  • R 21 and R 22 are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
  • R 23 to R 26 are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (provided that the total number of perfluoroalkyl groups substituted with ring X substituted with m Ls). Is 1 or more and less than 2 mn)
  • Q 21 is a single bond or -CH 2- L is a linking group composed of one aromatic ring.
  • m is an integer greater than or equal to 1 and n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
  • R 31 , R 35 , and R 39 are independently monovalent aromatic ring groups, respectively.
  • R 32 to R 34 , R 36 to R 38 , and R 40 to R 48 are independently hydrogen atoms, perfluoroalkyl groups, or electron donating groups (provided that they are replaced with 6 rings X).
  • the total number of perfluoroalkyl groups to be produced is 1 to 8), Item 2.
  • the compound according to Item 1, wherein Q 31 to Q 33 and Q 41 to Q 43 are each independently represented by either a single bond or -CH 2-].
  • Item 11 A delayed fluorescent material containing the compound according to any one of Items 1 to 10.
  • Item 12 An organic light emitting device containing the compound according to any one of Items 1 to 10.
  • Item 13 The organic light emitting element according to claim 12, which is an organic EL element.
  • R 1a is a monovalent aromatic ring group and R 1c and R 1h are perfluoroalkyl groups, and one or two of R 1b , R 1d , R 1e , R 1f , R 1g , and R 1i are bromine atoms, and the rest are hydrogen atoms or An electron donating group, or R 1d and R 1g are perfluoroalkyl groups, and one or two of R 1b , R 1c , R 1e , R 1f , R 1h , and R 1i are bromine. It is an atom, the rest is a hydrogen atom or an electron donating group, and Q 1a is a single bond or -CH 2- ].
  • R 21 and R 22 are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
  • R 23 to R 26 are independently hydrogen atoms or perfluoroalkyl groups (provided that at least one of the m rings substituted with L has at least one of R 23 to R 26 .
  • the individual is a perfluoroalkyl group, and not all of R 23 to R 26 are perfluoroalkyl groups),
  • Q 21 is a single bond or -CH 2-
  • L is a linking group composed of one aromatic ring.
  • X is a halogen atom
  • m is an integer greater than or equal to 1
  • n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
  • p and q are the maximum numbers that can be independently replaced with 0 or L, respectively.
  • a is an integer greater than or equal to 1 and less than n] The compound represented by.
  • a nitrogen-containing heterocyclic compound having a perfluoroalkyl group having a suitable emission wavelength and a technique relating to its use are provided.
  • FIG. 1A is a diagram showing a 1 H NMR spectrum of the learning compound S5.
  • FIG. 1B is a partially enlarged view of FIG. 1A.
  • FIG. 2 is a diagram showing a 1 H NMR spectrum of the learning compound S6.
  • FIG. 3A is a diagram showing a 1 H NMR spectrum of the learning compound S7.
  • FIG. 3B is a partially enlarged view of FIG. 3A.
  • FIG. 3C is a diagram showing a 19 F NMR spectrum of the learning compound S7.
  • FIG. 4A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T1.
  • FIG. 4B is a diagram showing a 19 F NMR spectrum of an intermediate of the test compound T1.
  • FIG. 4A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T1.
  • FIG. 4B is a diagram showing a 19 F NMR spectrum of an intermediate of the test compound T1.
  • FIG. 4A is a diagram showing
  • FIG. 4C is a diagram showing an IR spectrum of an intermediate of the test compound T1.
  • FIG. 5A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T4.
  • FIG. 5B is a partially enlarged view of FIG. 5A.
  • FIG. 5C is a diagram showing an IR spectrum of an intermediate of the test compound T4.
  • FIG. 6A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T19.
  • FIG. 6B is a partially enlarged view of FIG. 6A.
  • FIG. 6C is a diagram showing an IR spectrum of an intermediate of the test compound T19.
  • FIG. 7A is a diagram showing a 1 H NMR spectrum of the test compound T19.
  • FIG. 7B is a partially enlarged view of FIG. 7A.
  • FIG. 7C is a diagram showing an IR spectrum of the test compound T19.
  • FIG. 8A is a diagram showing a 1 H NMR spectrum of the test compound T19-2.
  • FIG. 8B is a partially enlarged view of FIG. 8A.
  • FIG. 8C is a diagram showing a 19 F NMR spectrum of the test compound T19-2.
  • FIG. 8D is a diagram showing an IR spectrum of the test compound T19-2.
  • FIG. 9 is a diagram showing a 1 H NMR spectrum of the test compound T21.
  • FIG. 10A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T22.
  • FIG. 10B is a partially enlarged view of FIG. 10A.
  • FIG. 10C is a diagram showing a 19 F NMR spectrum of an intermediate of the test compound T22.
  • FIG. 11A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T25.
  • FIG. 11B is a partially enlarged view of FIG. 11A.
  • FIG. 11C is a diagram showing a 19 F NMR spectrum of an intermediate of the test compound T25.
  • FIG. 12A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T28. 12B is a partially enlarged view of FIG. 12A.
  • FIG. 12C is a diagram showing a 19 F NMR spectrum of an intermediate of the test compound T28.
  • FIG. 13A is a diagram showing a 1 H NMR spectrum of the test compound T28.
  • FIG. 13B is a diagram showing a 19 F NMR spectrum of the test compound T28.
  • FIG. 13C is a diagram showing an IR spectrum of the test compound T28.
  • FIG. 14A is a diagram showing a 1 H NMR spectrum of an intermediate of the test compound T31.
  • 14B is a partially enlarged view of FIG. 14A.
  • FIG. 14C is a diagram showing a 19 F NMR spectrum of an intermediate of the test compound T31.
  • FIG. 14D is a diagram showing an IR spectrum of an intermediate of the test compound T31.
  • FIG. 15A is a diagram showing a 1 H NMR spectrum of the test compound T34.
  • FIG. 15B is a partially enlarged view of FIG. 15A.
  • FIG. 15C is a diagram showing a 19 F NMR spectrum of the test compound T34.
  • FIG. 15D is a diagram showing an IR spectrum of the test compound T34.
  • halogen atom is used in the sense of including a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
  • alkyl group means a chain saturated hydrocarbon group, and specifically, for example, a methyl group, an ethyl group, or a propyl group (n-propyl group, isopropyl). Groups), butyl groups (n-butyl group, isobutyl group, sec-butyl group, tert-butyl group), pentyl group, hexyl and other linear or branched C 1-20 alkyl groups.
  • the "perfluoroalkyl group” means a group in which all hydrogen atoms of the alkyl group are substituted with fluorine atoms, and specifically, for example, a trifluoromethyl group.
  • alkoxy group means a group in which an oxygen atom is bonded to the terminal of the alkyl group, and specifically, for example, a methoxy group, an ethoxy group, or a propoxy group (n).
  • -Propoxy group isopropoxy group
  • butoxy group n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group
  • other linear or branched C 1-12 alkoxy groups can be mentioned.
  • aromatic ring is used in the sense of including an aromatic hydrocarbon ring and an aromatic heterocycle.
  • the number of carbon atoms in the aromatic hydrocarbon ring is not particularly limited, but is, for example, 6 to 40.
  • the aromatic hydrocarbon ring is preferably a benzene ring or a condensed ring having a structure in which a plurality of benzene rings are condensed.
  • aromatic hydrocarbon ring examples include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an anthracene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a tetracene ring, a benzopyrene ring, a perylene ring, a coronene ring, a phenanthrene ring, and a phenalene ring. Rings, triphenylene rings, etc. can be mentioned.
  • the aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring.
  • the number of ring-constituting atoms in the aromatic heterocycle is not particularly limited, but is, for example, 5 to 40 members.
  • the aromatic heterocycle is preferably an aromatic heterocycle containing at least one heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom as a ring-constituting atom.
  • the aromatic heterocycle include an oxygen-containing aromatic heterocycle (eg, furan ring, benzofuran ring, dibenzo [b, d] furan ring), and a sulfur-containing aromatic heterocycle (eg, thiophene ring, benzothiophene ring, etc.).
  • Dibenzo [b, d] thiophene ring dibenzo [b, d] thiophene ring
  • nitrogen-containing aromatic heterocycle eg, pyrrol ring, pyrazole ring, imidazole ring, 1,2,3-triazole ring, 1,2,4-triazole ring, pyridine ring, pyridazine
  • Ring pyrimidine ring, pyrazine ring, 1,3,5-triazine ring, indole ring, indazole ring, benzoimidazole ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phthalazine ring, naphthylidine ring, purine ring, acrydin ring , Phenazine ring, phenanthroline ring), oxygen-containing and nitrogen-aromatic heterocycle (eg, oxazole ring, isooxazole ring,
  • the aromatic heterocycle is usually other than a carbazole ring, preferably a 5- or 6-membered aromatic heterocycle, more preferably a 5- or 6-membered nitrogen-containing aromatic heterocycle, and pyridine. More preferably, it is a ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a 1,3,5-triazine ring.
  • the "aromatic ring” also includes an aromatic ring having one or more substituents.
  • substituents include an alkyl group, a perfluoroalkyl group, an alkoxy group, a cyano group, an aryl group, a heteroaryl group and the like, and these may be further substituted.
  • the number of substituents is selected from a range of 0 or more and not more than the maximum number substitutable for aromatic rings, and may be, for example, 1, 2, 3, or 4.
  • monovalent aromatic ring group means a group obtained by removing one hydrogen atom from the aromatic ring.
  • the monovalent aromatic ring group includes a group obtained by removing one hydrogen atom from the aromatic hydrocarbon ring (aryl group) and a group obtained by removing one hydrogen atom from the aromatic heterocycle (heteroaryl group).
  • aryl group examples include a C 6-18 aryl group such as a phenyl group and a naphthyl group.
  • heteroaryl group examples include a fryl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazil group, a pyridyl group, a pyridadyl group, a pyrimidyl group, a pyrazil group, a triazinyl group, an oxazolyl group, an isooxazolyl group and a thiazolyl group. Examples thereof include an isothiazolyl group.
  • the "electron donating group (donor group)" represents a group in which Hammett's ⁇ p is negative. Hansch, C.et.al., Chem.Rev., 91,165-195 (1991) can be referred to for a description of Hammett's ⁇ p and the numerical values of each group.
  • Preferred electron donating groups include, for example, an alkyl group such as a methyl group, an aryl group such as a phenyl group, an alkoxyl group such as a methoxy group, an alkylsulfanyl group such as a methionyl group, and a ring X such as an N-phenylcarbazolyl group. Examples include groups having.
  • the compound of the present invention is a compound having N rings (N is an integer of 2 or more) in which two adjacent rings X are (A) directly linked, (B). )
  • the total number of perfluoroalkyl groups substituted by N ring X, which is linked by either ⁇ -conjugated linking group or (C) condensation linking, is 1 or more and less than 2N. It is preferably a compound. It is preferable that one or more rings X are carbazole rings (Q is a single bond).
  • the N rings X are preferably only carbazole rings, and preferably a combination of carbazole rings and acridine rings (Q is ⁇ CH 2-).
  • Ring X may have one or more substituents (perfluoroalkyl group, electron donating group, etc.). At least one (preferably two) benzene rings contained in each of one or more and less than N rings X are in the meta-position or para-position (preferably the meta-position) with respect to the nitrogen atom bonded to the benzene ring. It is preferable to have a perfluoroalkyl group in. Further, at least one (preferably two) benzene rings contained in each of one or more and less than N rings X have a perfluoroalkyl group at the meta position with respect to the nitrogen atom bonded to the benzene ring. However, it is also preferable to have an electron donating group at the para position.
  • any atom of one ring X and any atom of the other ring X can be linked by a single bond.
  • the nitrogen atom of one ring X and the carbon atom in the meta position or the para position (preferably the meta position) with respect to the nitrogen atom bonded to the benzene ring contained in the other ring X are connected by a single bond. It is preferable to do so.
  • the nitrogen atom at the 9-position of one carbazole ring and an arbitrary atom of the other carbazole ring are linked by a single bond, and the nitrogen atom at the 9-position of one carbazole ring is linked.
  • the carbon atoms at the 2-position, 3-position, 6-position, or 7-position of the other carbazole ring are linked by a single bond, and the nitrogen atom at the 9-position of one carbazole ring and the 3-position of the other carbazole ring are further preferable.
  • the carbon atom at the 6-position is connected by a single bond.
  • the type of the ⁇ -conjugated connecting group is not particularly limited as long as it can form a ⁇ -electron conjugated system, and the electrons of the ⁇ orbital interact with the ⁇ * orbital or the empty p-orbital located at spatially close positions. By doing so, it may be possible to form hyperconjugation.
  • the ⁇ -conjugated linking group may be a non-aromatic ⁇ -conjugated linking group or an aromatic ⁇ -conjugated linking group.
  • non-aromatic ⁇ -conjugated linking group examples include hyperconjugated methylene (CH 2 ) group, CF 2 group, C (CF 3 ) 2 group and the like.
  • the aromatic ⁇ -conjugated linking group may be a linking group composed of one aromatic ring, or may be a linking group composed of two or more aromatic rings directly bonded to each other.
  • the aromatic ring is a benzene ring, a naphthalene ring, a 5- or 6-membered aromatic heterocycle, a dibenzo [b, d] furan ring, or a dibenzo [b, d].
  • a thiophene ring is preferable, and a benzene ring or a 5- or 6-membered nitrogen-containing aromatic heterocycle is more preferable, and a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or 1, It is more preferably a 3,5-triazine ring.
  • a linking group composed of two or more aromatic rings directly bonded to each other is, for example, the following formula: (In the equation, Ar 1 to Ar 6 are independently aromatic rings, and a2, a3, a4, and a6 are independently integers of 0 or more.) Based on the structure represented by.
  • the aromatic ring represented by Ar 1 to Ar 6 is preferably a benzene ring or a 5- or 6-membered nitrogen-containing aromatic heterocycle, and is preferably a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring. Alternatively, it is more preferably a 1,3,5-triazine ring.
  • A2 and a6 are preferably 0, 1, 2, 3, or 4, more preferably 0, 1, 2, or 3, and even more preferably 0, 1, or 2.
  • A3 is preferably 0 or 1.
  • a4 is preferably 0, 1, or 2, and more preferably 0 or 1.
  • a3 and a4 are preferably 0.
  • Ar 1 , Ar 2 , and Ar 6 are benzene rings
  • Ar 5 is a benzene ring or a 1,3,5-triazine ring.
  • a3 is 1 and a4 is 0.
  • a2 and a6 are 0, and Ar 1 , Ar 3 , and Ar 5 are benzene rings.
  • a linking group composed of two or more aromatic rings directly bonded to each other preferably has the following formula: (During the ceremony, X 1 to X 5 are independently CR 6 or N, respectively. R 1 to R 6 are independently hydrogen atoms, alkyl groups, perfluoroalkyl groups, cyano groups, or aryl groups. The dashed line indicates aromaticity. ) Structure represented by, or (During the ceremony, R 1 ', R 2', R 4 ', and R 5' are each independently a hydrogen atom, an alkyl group, a perfluoroalkyl group, a cyano group, or an aryl group, X 1 to X 5 , R 1 to R 5 , and the broken line are the same as described above. ) Based on the structure represented by.
  • R 1 to R 5 A combination in which R 1 , R 2 , R 4 , and R 5 are hydrogen atoms and R 3 is an alkyl group, a perfluoroalkyl group, a cyano group, or an aryl group is preferable.
  • condensation connection the condensation form of two adjacent rings X is not particularly limited. Both rings X are condensed, and the formula: (In the equation, Q 1 and Q 2 are independently single-bonded or -CH 2- .) It is preferable to connect by forming a ring represented by the formula: It is more preferable to connect by forming a ring represented by. These fused rings may be further connected to adjacent rings X. In this case, the number of rings X is counted as three.
  • both carbazole rings are fused to indro [3,2-a] carbazole ring, indro [3,2-b] carbazole ring, indro [2,3-a] carbazole ring.
  • Indro [2,3-b] carbazole ring, or indro [2,3-c] carbazole ring may be linked.
  • both carbazole rings are condensed to form an indro [3,2-a] carbazole ring to form a link.
  • fused rings are further linked to adjacent carbazole rings to form a diindro [2,3-a: 2', 3'-c] carbazole ring or diindro [3,2-a: 3', 2'-c. ] It may be linked by forming a carbazole ring.
  • N is not particularly limited as long as it is 2 or more, but is preferably 12 or less, 10 or less, or 8 or less.
  • the number of perfluoroalkyl groups that can be substituted with one ring X is preferably 4 or less, more preferably 3 or less, still more preferably 2 or less.
  • the total number of perfluoroalkyl groups substituted with N rings X may be even or odd. When the number is odd, a plurality of stereoisomers exist and each structure contributes to TADF, so that the inverse intersystem crossing speed can be improved and the durability of the light emitting material can be improved.
  • the total number of perfluoroalkyl groups substituted on N rings X is 1 or more and less than 2N, and when the total number of perfluoroalkyl groups substituted on N rings X is 0 or 2N.
  • the emission wavelength tends to be longer than that of the above, and the emission wavelength tends to become longer as the total number of perfluoroalkyl groups substituted with N rings X increases.
  • the ring X substituted by the perfluoroalkyl group is preferably substituted with two perfluoroalkyl groups, and the two substitution positions are not particularly limited, but the ring X is substituted. It is preferably in the meta-position or the para-position with respect to the nitrogen atom bonded to the contained benzene ring. That is, when the ring X is an acridine ring or a carbazole ring, the two substitution positions are preferably 2-positions and 7-positions, or 3-positions and 6-positions.
  • the perfluoroalkyl group is substituted at the 2-position and 7-position, or the 3-position and 6-position of one or more and less than N carbazole rings, and 2 of the carbazole ring having 1 or more and less than N It is more preferable that the perfluoroalkyl group is substituted at the position and the 7-position.
  • Compounds in which the perfluoroalkyl group is substituted at the 2- and 7-positions of the carbazole ring are compounds in which the perfluoroalkyl group is not substituted in the carbazole ring, and the perfluoroalkyl group is substituted in the 3- and 6-positions of the carbazole ring.
  • the excitation triplet state (T1) energy is lower than that of the compound. Therefore, the TADF material having this as a partial structure has a small energy difference between the excited triplet CT state and the excited triplet state of the carbazole portion, and mixing between orbitals is likely to occur. Therefore, the inverse intersystem crossing from the excited triplet state to the excited singlet state is promoted, and the delayed fluorescence lifetime tends to be shortened.
  • perfluoroalkyl group a perfluoroC 1-6 alkyl group is preferable, and a perfluoroC 1-4 alkyl group is more preferable.
  • the compound of the present invention has the following formulas (1) to (3): [During the ceremony, R 10 is a monovalent aromatic ring group and R 11 to R 20 are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (however, the total number of perfluoroalkyl groups substituted with three rings X is one. ⁇ 5), Q 11 ⁇ Q 13 are each independently a single bond or -CH 2 -, R 21 and R 22 are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
  • R 23 to R 26 are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (provided that the total number of perfluoroalkyl groups substituted with ring X substituted with m Ls).
  • Q 21 is a single bond or -CH 2-
  • L is a linking group composed of one aromatic ring.
  • m is an integer greater than or equal to 1 and n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
  • p and q are independently the maximum number (existence) that can be replaced with 0 (absence) or L, respectively.
  • R 31 , R 35 , and R 39 are independently monovalent aromatic ring groups, respectively.
  • R 32 to R 34 , R 36 to R 38 , and R 40 to R 48 are independently hydrogen atoms, perfluoroalkyl groups, or electron donating groups (provided that they are replaced with 6 rings X).
  • the total number of perfluoroalkyl groups to be produced is 1 to 8
  • Q 31 ⁇ Q 33 and Q 41 ⁇ Q 43 are each independently a single bond or -CH 2 - is preferably a compound represented by any one of a.
  • the R 10 is preferably an aryl group, more preferably a phenyl group or a naphthyl group, and even more preferably a phenyl group. These may have one or more substituents, and examples of the substituent include an alkyl group, a perfluoroalkyl group, and a cyano group.
  • R 11 and R 12 are perfluoroalkyl groups and R 13 , R 14 , R 17 and R 18 are hydrogen atoms, perfluoroalkyl groups, or electron donating groups.
  • R 15 , R 16 , R 19 and R 20 are hydrogen atoms or electron donating groups is preferable.
  • R 11 and R 12 are perfluoroalkyl groups and A combination in which R 13 to R 20 are hydrogen atoms, or R 11 , R 12 , R 13 and R 14 are perfluoroalkyl groups.
  • a combination in which R 15 to R 20 are hydrogen atoms is more preferable.
  • the total number of perfluoroalkyl groups substituted with 3 rings X is preferably 2-4.
  • a C 1-4 alkyl group is preferable, a C 1-3 alkyl group is more preferable, and a methyl group or an ethyl group is further preferable.
  • Examples of the monovalent aromatic ring group represented by R 21 and R 22 include the same group as R 10, and an aryl group or a heteroaryl group which may have one or more phenyl groups. Is preferable, or a pyridyl group, a pyridazil group, a pyrimidyl group, a pyrazil group, or a triazil group which may have one or more phenyl groups is more preferable.
  • R 21 and R 22 are particularly preferably hydrogen atoms, methyl groups, phenyl groups, or 4,6-diphenyl-1,3,5-triazine-2-yl groups.
  • R 23 and R 24 are hydrogen atoms or electron donating groups
  • R 25 and R 26 are perfluoroalkyl groups
  • R 23 and R 24 are perfluoroalkyl groups
  • a combination in which R 25 and R 26 are hydrogen atoms or electron donating groups is more preferable. It is preferable that all of R 23 to R 26 are not perfluoroalkyl groups.
  • L examples include a group exemplified as a linking group composed of one aromatic ring in the description of the ⁇ -conjugated linking group.
  • L is preferably a linking group composed of a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a 1,3,5-triazine ring.
  • N is preferably 2, 3, 4, or 5 depending on the type of L.
  • M is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, and even more preferably 1 or 2.
  • the maximum number that can be replaced with 0 or L can be selected depending on L, n, and m.
  • Example 1 When m is 1, L is a pyridine ring, and n is 5, p and q are 0.
  • Example 2 When m is 1, L is a benzene ring, and n is 5, the sum of p and q is 1.
  • Example 3 When m is 1, L is a benzene ring, and n is 4, the sum of p and q is 2.
  • Example 4 When m is 1, L is a benzene ring, and n is 3, the sum of p and q is 3.
  • each L is a benzene ring, the number n of rings X substituted with L to which R 21 is bonded is 4, and the number of rings X substituted with L to which R 22 is bonded.
  • n 2, p is 1 and q is 3.
  • m 2, L to which R 21 is bonded is a benzene ring, L to which R 22 is bonded is a 1,3,5-triazine ring, and a ring substituted with L to which R 21 is bonded.
  • p is 1 and q is 0.
  • examples of the monovalent aromatic ring group represented by R 31 , R 35 , and R 39 include the same group as R 10 , preferably an aryl group, and a phenyl group or a naphthyl group. Is more preferable, and a phenyl group is further preferable.
  • R 32 to R 34 , R 36 to R 38 , and R 40 to R 48 are perfluoroalkyl groups
  • R 32 , R 33 , R 36 , and R 37 are perfluoroalkyl groups
  • Combinations in which R 34 , R 38 , and R 40 to R 48 are hydrogen atoms are also preferred
  • a combination in which R 32 , R 33 , R 36 , R 37 , R 40 , and R 41 are perfluoroalkyl groups and R 34 , R 38 , and R 42 to R 48 are hydrogen atoms is more preferred.
  • the compound of the present invention is preferably a compound selected from the compound group shown in Table 1 below.
  • the compound of the present invention preferably satisfies the following formula (a).
  • the descriptor "SMR_VSA9" is the total surface area (unit: ⁇ 2 ) of the carbon having a triple bond and the aromatic carbon bonded to the oxygen atom and the aromatic ring. More specifically, SMR_VSA9 is one of the VSA-type descriptors created by LABUTE to predict the physicochemical properties of molecules such as free dissolution energy and boiling point (LABUTE, Paul. A widely applicable set of). descriptors. Journal of Molecular Graphics and Modeling, 2000, 18.4-5: 464-477).
  • VSA type descriptor is defined as the sum of the surface areas having the property P within a certain range, assuming that each atom in the molecule has an arbitrary property (numerical value) P i. It is represented by.
  • V i is the van der Waals surface area (VS A) of each atom, which is a value approximately calculated from the van der Waals radius of the atom and the standard bond length.
  • ⁇ (A) is a function that returns 1 when the conditional expression A is true and 0 when it is false.
  • the VSA type descriptor "P_VSAk” is the sum of V i ⁇ (A) for all atoms except the hydrogen atom.
  • SMR_VSAk When the P i of the conditional expression A is MR (described later), this VSA type descriptor is called SMR_VSAk.
  • SMR_VSAk mainly describes the polarizability.
  • the range boundary ⁇ a k ⁇ for SMR_VS Ak is given by the following equation (S2): It is represented by.
  • MR is an atomic contribution method (the following formula (S3)): It is the coefficient P i of each atom in predicting by, those determined from the experimental data of 3412 molecules by Crippen et al. MR values are defined for each of the 68 atomic types.
  • SMR_VSA9 can be said to be the sum of the van der Waals surface areas of atoms belonging to the atomic type in the corresponding range [3.80, 4.00].
  • the descriptor "fr_para_hydroxylation” indicates the number of reaction sites on the aromatic ring that can undergo para-hydroxylation.
  • the definition of the reaction site on the aromatic ring that can undergo hydroxylation in the descriptor satisfies both (b1) and (b2) below.
  • (B1) An oxygen atom or a nitrogen atom is bonded to an aromatic ring composed of 6 carbon atoms.
  • the aromatic ring may be a partial structure of a polycyclic aromatic compound, and the oxygen atom and the nitrogen atom may be a part constituting another ring structure condensed with the aromatic ring.
  • the nitrogen atom must be covalently bonded to three arbitrary atoms or covalently bonded to two hydrogen or carbon atoms.
  • the descriptor "HOMO-LUMO Gap” is a value obtained by calculating the HOMO and LUMO energy levels of the compound by quantum chemistry calculation and subtracting the HOMO level from the calculated LUMO level.
  • the quantum chemistry calculation was performed by the density functional theory, and B3LYP was used for the functional and 6-31g (d, p) was used for the basis set.
  • the energy level the value calculated when the structure was optimized by the functional and the basis function was used as a representative value.
  • the software for quantum chemistry calculation is not particularly limited and can be obtained in the same manner by using any of them, but Gaussian 09 Rev. D is used in the present invention.
  • Equation (b) is preferably a prediction equation (or regression equation) for the maximum emission wavelength, which is created by machine learning.
  • Step (i) The learning compound is not particularly limited as long as the emission maximum wavelength is known or the compound is measured by the following method. (Measurement method of maximum emission wavelength) Excitation light of 280 nm was applied to a thin film (thickness 50 nm) adjusted so that the learning compound was 10% by mass with respect to the host material (2,8-Bis (diphenylphosphoryl) dibenzo [b, d] thiophene (PPT)). The peak top of the emission spectrum when irradiated is measured.
  • the learning compound preferably includes both a compound having a measured maximum emission wavelength of 400 nm or less and a compound having a maximum emission wavelength of 500 nm or more.
  • the learning compounds include a compound in which two perfluoroalkyl groups are substituted on all rings X and a perfluoroalkyl group on all rings X. It preferably contains both compounds in which the alkyl group has not been substituted at all.
  • the learning compound preferably comprises a compound selected from the compound group shown in Table 3 below.
  • the lower limit of the number of learning compounds is not particularly limited, but from the viewpoint of improving prediction accuracy, 5 or more is preferable, 10 or more is more preferable, 15 or more is further preferable, and 20 or more is particularly preferable.
  • the upper limit of the learning compound is not particularly limited, but from the viewpoint of data collectability, 50 or less is preferable, 40 or less is more preferable, and 30 or less is further preferable.
  • the type of descriptor related to the maximum emission wavelength is not particularly limited.
  • the descriptor associated with the emission maximum wavelength is preferably at least one selected from 0-4D descriptors.
  • Examples of the 0-dimensional descriptor include the number of atoms such as C, H, O, N, and halogen, the number of bonds, and the molecular weight.
  • the one-dimensional descriptor includes, for example, the number of functional groups such as an alkyl group, an aryl group, an arylalkyl group, a hydroxy group, an ester group, and an amino group, the number of aromatic rings, and on an aromatic ring capable of undergoing para-hydroxylation. The number of reaction points and the like can be mentioned.
  • Examples of the two-dimensional descriptor include those characterized by structural formulas such as SMR_VSA1 to 10, PEOE_VSA1 to 14, SlogP_VSA1 to 12, Estate_VSA1 to 11.
  • Examples of the three-dimensional descriptor include geometrically characterized ones such as 3D-MoRSE, WHIM, and GETAWAY, and HOMO-LUMO Gap and the like.
  • Examples of the four-dimensional descriptor include those calculated by GRID, CoMFA, Volsurf, etc. and characterized by the interaction energy.
  • the descriptors related to the emission maximum wavelength include, for example, 80% or more, preferably 90% or more, more preferably 95% or more, and particularly preferably 100% of the total number of learning compounds. Preferably do not contain descriptors that have the same value in common.
  • the number of descriptors related to the maximum emission wavelength is not particularly limited. From the viewpoint of overfitting, the number of descriptors related to the emission maximum wavelength is preferably smaller than the number of learning compounds. Also, the number of descriptors associated with the emission maximum wavelength may be adjusted using regularization to control the coefficients of the descriptors.
  • the method for extracting the descriptor related to the emission maximum wavelength from the structure of the learning compound is not particularly limited, but (i-1) a step of generating a group of descriptor values from the structure of the learning compound, and (i). -2) It is preferable that the method includes a step of extracting a descriptor related to the emission maximum wavelength from the group.
  • the method further preferably includes a step of normalizing and transforming the values of the set of descriptors generated in step (i-1). Examples of the normalization conversion method include standardization conversion and Yeo-Johnson conversion. In one embodiment, it is more preferred to perform the normalization transformation using Scikit-learn, a Python library for machine learning.
  • Examples of the extraction method in step (i-2) include a method of extracting by sparse modeling, a method of selecting by the correlation coefficient with the prediction target, and a method of recursively adding or deleting descriptors based on the prediction accuracy. Be done. Of these, the method of extraction by sparse modeling is preferable.
  • Examples of sparse modeling include greedy method, convex relaxation method, and stochastic reasoning.
  • Examples of the greedy algorithm include orthogonal matching tracking (OMP), matching tracking (MP), weak matching tracking (Weak MP), and threshold algorithm.
  • Examples of the convex relaxation method include a basis tracking method, an iterative reweighting least squares method (IRLS), and a homotopy method.
  • Probabilistic inference includes approximate message propagation method (AMP).
  • the sparse modeling is preferably orthogonal matching tracking.
  • Step (ii) it is preferable to create a prediction formula by machine learning.
  • Machine learning includes, for example, multiple regression, Ridge regression, LASSO regression, Elastic Net, support vector regression, random forest regression, neural network and the like. These may be used alone or in combination of two or more. When the number of data is small, it is preferable to adopt the method of adopting a linear model from the viewpoint of prevention of overfitting and high interpretability.
  • machine learning is preferably Ridge regression, Lasso regression, Elastic Net.
  • machine learning includes LibSVM, TensorFlowTM, Chainer TM, Jubatus TM, Caffe, Theano, Torch, neonTM, MXNet, The Microsoft Cognitive Toolkit, R (C), MATLAB TM, Using computer software such as Mathematica TM, SAS TM, RapidMiner TM, KNIME TM, WeKa, shogun-toolbox / shogun, Orange, Apache MahoutTM, scikit-learn, mlpy, XGBoost, Deeplearning4j It is preferable to carry out.
  • the compound of the present invention preferably satisfies the following formula (c): W 1 > W 2 (c) [W 1 in equation (c) is the same as W 1 in equation (a), W 2 of the formula (c) has the total number of perfluoroalkyl groups substituted with N rings X, where N is the total number of rings X contained in the compound in the formula (b). W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the comparative compound having the same structure as the compound except that the number is 0].
  • the compound of the present invention is useful as a delayed fluorescent material. Further, the compound of the present invention is useful as a light emitting material for an organic light emitting device, and can be suitably used as a material for a light emitting layer of an organic light emitting device.
  • the emission maximum wavelength ( ⁇ max) of the compound of the present invention is preferably 450 nm or more or 455 nm or more, or 520 nm or less or 510 nm or less.
  • ⁇ max the maximum emission wavelength
  • the peak top of the emission spectrum when a thin film (thickness 50 nm) adjusted so that the compound of the present invention is 10% by mass with respect to the host material (PPT) is irradiated with excitation light of 280 nm is measured. It is required by doing.
  • the HOMO level of the compound of the present invention may preferably be -5.0 eV or less or -5.5 eV or less, and is -7.0 eV or more, -6.5 eV or more, or -6.4 eV or more. You may. As the total number of perfluoroalkyl groups substituted with N rings X increases, the HOMO level tends to decrease. Due to such a HOMO level, compatibility with peripheral materials such as host materials is excellent.
  • the HOMO level can be measured using an atmospheric photoelectron spectrometer (for example, AC-3 manufactured by RIKEN Keiki Co., Ltd.).
  • the absolute value of the difference between the lowest excited singlet energy (S 1) and the lowest excited triplet energy of the compound of the present invention (T 1) is preferably not more than 0.3eV or less, or 0.2 eV, Usually, it is 0.001 eV or more.
  • ⁇ E ST can be measured by the same method as the method for measuring ⁇ max, and the fluorescence spectrum (room temperature) and the phosphorescence spectrum (77K) can be measured and calculated from the difference between the rising wavelengths of the respective rising wavelengths.
  • the compound of the present invention is characterized in that the total number of perfluoroalkyl groups substituted with N carbazole rings is 0 or 2N (particularly, each carbazole ring is substituted with 2 perfluoroalkyl groups). Except for this, it is preferable that the emission intensity is higher than that of a compound having the same structure as the compound of the present invention (comparative compound).
  • the emission intensity of the compound of the present invention is preferably 110 or more or 120 or more when the emission intensity of the comparative compound is 100. When the light emission intensity is in such a range, the light emission efficiency is high and the power consumption of the device can be reduced.
  • the emission intensity is determined by the following formula from the ratio of peak emission intensity when a thin film (thickness 50 nm) adjusted so that the light emitting material is 10% by mass with respect to the host material (PPT) is irradiated with excitation light of 280 nm. I asked.
  • Emission intensity (Peak emission intensity of the compound of the invention) / (Peak emission intensity of the compound having a carbazole ring in which the perfluoroalkyl group is not substituted) ⁇ 100
  • the peak emission intensity can be measured by a conventional device (for example, "PMA12" manufactured by Hamamatsu Photonics Co., Ltd.).
  • the delayed fluorescence lifetime of the compound of the present invention is preferably 10 ⁇ s or less or 5 ⁇ s or less, and usually 10 ns or more.
  • the delayed fluorescence lifetime can be measured by a conventional device (for example, "Quantaurus-Tau” manufactured by Hamamatsu Photonics Co., Ltd.).
  • the excited state stability of the compound of the present invention is preferably 0.5 hours or more or 1 hour or more. When the excited state stability is in such a range, the durability of the device can be improved.
  • a toluene solution (concentration 1.0 x 10-5 M) of the compound of the present invention was used, degassed by argon bubbling, and then excited light (Xenon light source MAX-303 manufactured by Asahi Spectroscopy Co., Ltd.) with stirring. It is obtained by irradiating a wavelength of 300 to 400 nm, 5 mW / cm 2 ) and measuring the time from the initial emission to the reduction of the emission intensity by half.
  • the compound of the present invention is a reaction in which, for example, two rings X are linked by either (A) direct linking, (B) linking via a ⁇ -conjugated linking group, or (C) condensation linking. Can be repeatedly manufactured.
  • reaction linked by direct linking is not particularly limited as long as it is a reaction in which a direct bond is formed between an arbitrary atom of one ring X and an arbitrary atom of the other ring X.
  • reaction A may be a reaction between a halogen atom substituting for one ring X and an NH site of the other ring X (hereinafter referred to as reaction A).
  • One reaction component of the reaction A is preferably compound A1 having a ring X substituted with one or more halogen atoms, and the other reaction component is a compound A2 having a ring X in which the halogen atom is not substituted. Is preferable.
  • the halogen atom substituted for ring X is preferably a fluorine atom, a chlorine atom, or a bromine atom.
  • the number of halogen atoms substituted on the ring X is, for example, one or two, preferably two. Further, the substitution position of the halogen atom may be the 2-position, 3-position, 6-position, 7-position or the like of the acridine ring or the carbazole ring.
  • one or more (preferably two) perfluoroalkyl groups are substituted on the ring X of either one of the compound A1 and the compound A2, and one or more (preferably) the ring X of the compound A1 is substituted. It is more preferable that (2) perfluoroalkyl groups are substituted.
  • the substitution position of the perfluoroalkyl group may be the 2-position, 3-position, 6-position, 7-position or the like of the acridine ring or the carbazole ring.
  • the compound A1 has the following formula (4): [During the ceremony, R 1a is a monovalent aromatic ring group and R 1c and R 1h are perfluoroalkyl groups, and one or two of R 1b , R 1d , R 1e , R 1f , R 1g , and R 1i are bromine atoms, and the rest are hydrogen atoms or An electron donating group, or R 1d and R 1g are perfluoroalkyl groups, and one or two of R 1b , R 1c , R 1e , R 1f , R 1h , and R 1i are bromine. It is an atom, the rest is a hydrogen atom or an electron donating group, and Q 1a is a single bond or -CH 2- ].
  • the compound represented by is preferable.
  • the total number of moles of halogen atoms substituted for the ring X of the compound A1 is 0.5 mol or more, 0.6 mol or more, 0.7 mol with respect to 1 mol of the NH site of the ring X of the compound A2. It is preferable to use the above or 0.8 mol or more, and it is also preferable to use it so as to be 2.5 mol or less, 2 mol or less, 1.5 mol or less, or 1.2 mol or less.
  • Reaction A is preferably carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction component can be dissolved, and is, for example, an amine (eg, a chain amine such as triethylamine, a cyclic amine such as N-methylpyrrolidone), an amide (eg, dimethylformamide), a sulfoxide. (Example: dimethyl sulfoxide) and the like.
  • an amine eg, a chain amine such as triethylamine, a cyclic amine such as N-methylpyrrolidone
  • an amide eg, dimethylformamide
  • sulfoxide e.g, dimethyl sulfoxide
  • Reaction A is preferably carried out in the presence of a base.
  • the base include n-butyllithium, NaH, K 2 CO 3 , Cs 2 CO 3 , t-butoxy sodium, t-butoxy potassium, and a combination of two or more of these.
  • n-butyllithium refer to International Publication No. 2008/1178226, Chemistry of Materials, 2010, 22 (7), 2403-2410, etc.
  • NaH Korean Patent Application Publication No. 2018-063708 You can refer to the publications and the like.
  • Reaction A is preferably carried out in the presence of a catalyst.
  • the catalyst include a palladium catalyst and the like.
  • a palladium catalyst When a palladium catalyst is used, International Publication No. 2011/08902, International Publication No. 2015/137472, and the like can be referred to.
  • reaction B In the case of connection via a ⁇ -conjugated linking group, as long as the reaction is such that a bond is formed between an arbitrary atom of one ring X and an arbitrary atom of the other ring X via a ⁇ -conjugated linking group. There are no particular restrictions. For example, it may be a reaction (hereinafter, referred to as reaction B) between each halogen atom of the ⁇ -conjugated compound having two or more halogen atoms and the NH site of the ring X.
  • reaction B is preferably a ⁇ -conjugated compound B1 having two or more halogen atoms.
  • the ⁇ -conjugated compound B1 is not particularly limited as long as it is a compound that reacts with two or more rings X to form a ⁇ -conjugated linking group.
  • the halogen atom is preferably a fluorine atom, a chlorine atom, or a bromine atom, and the number of halogen atoms is 2, 3, 4, 5, or 6. preferable.
  • the ⁇ -conjugated compound B1 is preferably an aromatic compound having two or more halogen atoms.
  • the aromatic ring constituting the aromatic compound for example, in the description of the ⁇ -conjugated linking group, a linking group composed of one aromatic ring or a linking group composed of two or more aromatic rings directly bonded to each other. In the above, a ring exemplified as an aromatic ring can be mentioned.
  • the ⁇ -conjugated compound B1 has the following formula (5): [During the ceremony, X is a halogen atom, a is an integer of 1 or more and less than n, R 21 to R 26 , Q 21 , L, m, n, p, and q are the same as above]
  • the compound represented by is preferable.
  • a fluorine atom, a chlorine atom, or a bromine atom is preferable.
  • At least one of R 23 to R 26 is preferably a perfluoroalkyl group, and R 23 and R 24 , or R 25. And R 26 are more preferably perfluoroalkyl groups, and R 23 and R 24 are even more preferably perfluoroalkyl groups.
  • the other reaction component of reaction B is preferably compound B2 having a ring X in which the halogen atom is not substituted.
  • the total number of moles of halogen atoms in the compound is 0.5 mol or more, 0.6 mol or more, 0.7 mol or more, with respect to 1 mol of the NH site of the ring X of the compound B2.
  • it is preferably used so as to be 0.8 mol or more, and it is also preferable to use it so as to be 2.5 mol or less, 2 mol or less, 1.5 mol or less, or 1.2 mol or less.
  • Reaction B is preferably carried out in the presence of a solvent, a base, a catalyst, etc., as in Reaction A, and the same components as those exemplified in Reaction A can be used.
  • a condensate of two or more rings X can be used, for example, an indolo [3,2-a] carbazole ring, an indolo [3,2-b] carbazole ring, an indolo [ 2,3-a] carbazole ring, indolo [2,3-b] carbazole ring, indolo [2,3-c] carbazole ring, diindro [2,3-a: 2', 3'-c] carbazole ring, The diindro [3,2-a: 3', 2'-c] carbazole ring can be utilized.
  • the organic light emitting device of the present invention preferably contains the compound of the present invention, and more preferably contains the compound of the present invention as a light emitting material or an assist dopant compound.
  • organic light emitting element examples include an organic photoluminescence element (organic PL element) and an organic electroluminescence element (organic EL element).
  • organic light emitting element is preferably an organic EL element.
  • the organic EL element preferably has an anode, a cathode, and an organic layer formed between the anode and the cathode.
  • the organic layer preferably contains at least a light emitting layer, and may be composed of only a light emitting layer, or may include one or more other organic layers in addition to the light emitting layer.
  • Other organic layers include, for example, an injection layer (eg, a hole injection layer, an electron injection layer), a blocking layer (eg, an electron blocking layer, a hole blocking layer, an exciton blocking layer), a hole transport layer, and an electron.
  • the transportation layer and the like can be mentioned.
  • the hole transport layer may be a hole injection transport layer having a hole injection function
  • the electron transport layer may be an electron injection transport layer having an electron injection function.
  • the organic EL element may be a bottom emission type that extracts the light generated in the light emitting layer from the substrate side, or may be a top emission type that extracts the light generated in the light emitting layer from the opposite side of the substrate.
  • the electrode formed on the substrate side may be an anode or a cathode.
  • the electrode on the side that extracts light is preferably transparent, and the electrode on the opposite side may or may not be transparent.
  • the organic EL element is preferably supported by a substrate.
  • the substrate is not particularly limited as long as it is conventionally used for organic EL elements, and for example, a substrate made of glass, transparent plastic, quartz, silicon, or the like can be used.
  • anode in the organic EL element a metal having a large work function (for example, 4 eV or more), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material are preferably used.
  • electrode materials include metals such as Au and transparent conductive materials such as CuI, indium tin oxide (ITO), SnO 2, and ZnO.
  • a material such as IDIXO (In 2 O 3- ZnO) capable of producing an amorphous transparent conductive film may be used.
  • a thin film may be formed by a method such as vapor deposition or sputtering of the electrode material to form a pattern having a desired shape by a photolithography method, or a pattern may be formed through a mask having a desired shape during vapor deposition or sputtering of the electrode material. May be formed.
  • a coatable material such as an organic conductive compound
  • a wet film forming method such as a printing method or a coating method can also be used.
  • the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, but is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • a metal having a small work function for example, 4 eV or less
  • electron-injectable metal an alloy, an electrically conductive compound, or a mixture thereof as an electrode material
  • Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O). 3 ) A mixture, lithium / aluminum mixture, aluminum, etc. are suitable.
  • the cathode can be produced by forming a thin film of an electrode material by a method such as vapor deposition or sputtering.
  • the sheet resistance as a cathode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the cathode is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm. It is preferable that either the anode or the cathode of the organic EL element is transparent or translucent because the emission brightness is improved. Further, by using the transparent conductive material mentioned in the description of the anode for the cathode, a transparent or translucent cathode can be produced, and an element in which both the anode and the cathode have transparency can be produced.
  • the light emitting layer is a layer that emits light (eg, fluorescent light emission, delayed fluorescent light emission, or both) after excitons are generated by recombination of holes and electrons injected from each of the anode and cathode. Is preferable.
  • the light emitting layer may be a layer containing a light emitting material alone, but is preferably a layer containing a light emitting material and a host material.
  • the luminescent material the compound of the present invention (one type or two or more types) can be used.
  • the host material is not particularly limited, but it is preferable to use an organic compound in which at least one of the excitation singlet energy and the excitation triplet energy has a value higher than that of the compound of the present invention. Further, the host material is preferably an organic compound having a hole transporting ability and an electron transporting ability, preventing a long wavelength of light emission, and having a high glass transition temperature.
  • a compound exhibiting TADF properties is included in the light emitting layer as a third component (assist dopant compound) in the light emitting layer containing the host compound and the light emitting compound, it is effective in developing high luminous efficiency (H. Nakan Albany, et al). ., Nature Compound, 2014, 5, 4016-4022).
  • the triplet excitons generate singlet excitons with inverse intersystem crossing (RISC). can do.
  • RISC inverse intersystem crossing
  • the content of the compound of the present invention in the light emitting layer is preferably 0.1% by mass or more, more preferably 1% by mass or more, and preferably 50% by mass or less, preferably 20% by mass. It is more preferably 10% by mass or less, and further preferably 10% by mass or less.
  • the injection layer is preferably a layer provided between the electrode and the organic layer in order to reduce the driving voltage or improve the emission brightness.
  • the injection layer includes a hole injection layer and an electron injection layer.
  • the injection layer may be provided between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.
  • the blocking layer is preferably a layer capable of blocking the diffusion of charges (electrons or holes) and / or excitons existing in the light emitting layer to the outside of the light emitting layer.
  • the electron blocking layer can be arranged between the light emitting layer and the hole transporting layer, and can prevent electrons from passing through the light emitting layer toward the hole transporting layer.
  • the hole blocking layer can be placed between the light emitting layer and the electron transporting layer to prevent holes from passing through the light emitting layer towards the electron transporting layer.
  • the electron blocking layer and the hole blocking layer can also function as exciton blocking layers, respectively.
  • the electron blocking layer or exciton blocking layer referred to in the present specification is used in the sense that one layer includes a layer having the functions of an electron blocking layer and an exciton blocking layer.
  • the hole blocking layer has the function of an electron transport layer in a broad sense.
  • the hole blocking layer has a role of blocking the holes from reaching the electron transporting layer while transporting electrons, which can improve the recombination probability of electrons and holes in the light emitting layer.
  • As the material of the hole blocking layer a material of the electron transport layer described later can be used as needed.
  • the electron blocking layer has a function of transporting holes in a broad sense.
  • the electron blocking layer has a role of blocking electrons from reaching the hole transporting layer while transporting holes, which can improve the probability that electrons and holes are recombined in the light emitting layer. ..
  • the exciton blocking layer is preferably a layer for blocking excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer.
  • the exciton blocking layer can be inserted into either the anode side or the cathode side adjacent to the light emitting layer, and both can be inserted at the same time.
  • the layer when the exciton blocking layer is provided on the anode side, the layer can be inserted between the hole transport layer and the light emitting layer adjacent to the light emitting layer, and when inserted on the cathode side, the light emitting layer and the light emitting layer can be inserted.
  • the layer can be inserted adjacent to the light emitting layer between the cathode and the light emitting layer.
  • a hole injection layer, an electron blocking layer and the like can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer.
  • An electron injection layer, an electron transport layer, a hole blocking layer, and the like can be provided between the cathode and the exciton blocking layer adjacent to the cathode side of the light emitting layer.
  • the blocking layer it is preferable that at least one of the excited singlet energy and the excited triplet energy of the material used as the blocking layer is higher than the excited singlet energy and the excited triplet energy of the light emitting material.
  • the hole transport layer is preferably made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
  • a hole transporting material a material having either injection or transport of holes or an electron barrier property is preferable, and it may be either an organic substance or an inorganic substance.
  • the hole transporting material that can be used include triazole derivative, oxadiazole derivative, imidazole derivative, carbazole derivative, indolocarbazole derivative, polyarylalkane derivative, pyrazoline derivative and pyrazolone derivative, phenylenediamine derivative, arylamine derivative, and amino.
  • Examples thereof include substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilben derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • As the hole transport material it is preferable to use a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound, and it is more preferable to use an aromatic tertiary amine compound.
  • Inorganic semiconductors such as molybdenum oxide can also be used as the hole transport material.
  • the electron transport layer is preferably made of a material having a function of transporting electrons, and the electron transport layer can be provided with a single layer or a plurality of layers.
  • the electron transporting material (which may also serve as a hole blocking material) preferably has a function of transferring electrons injected from the cathode to the light emitting layer.
  • Examples of the electron transporting layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, freolenidenemethane derivatives, anthracinodimethane and anthrone derivatives, and oxadiazole derivatives.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is replaced with a sulfur atom, and a quinoxalin derivative having a quinoxalin ring known as an electron attractant can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • an inorganic semiconductor such as zinc oxide can also be used as an electron transport material.
  • the compound of the present invention may be used not only for the light emitting layer but also for a layer other than the light emitting layer.
  • the compound of the present invention used for the light emitting layer and the compound of the present invention used for the layer other than the light emitting layer may be the same or different.
  • the compound of the present invention may be used for the above-mentioned injection layer, blocking layer (eg, hole blocking layer, electron blocking layer, exciton blocking layer), hole transport layer, electron transport layer and the like.
  • the film forming method for these layers is not particularly limited, and may be formed by either a dry process or a wet process.
  • R, R', and R 1 to R 10 in the structural formulas of the following exemplified compounds independently represent hydrogen atoms or substituents.
  • X represents a carbon atom or a complex atom forming a ring skeleton
  • n represents an integer of 3 to 5
  • Y represents a substituent
  • m represents an integer of 0 or more.
  • the HOMO / LUMO level of the host material can be adjusted by appropriately introducing a substituent into the basic skeleton of the following exemplified compound. For example, by introducing a cyano group or a perfluoroalkyl group into the basic skeleton of the following exemplified compound, a compound having a deepened HOMO / LUMO level can be obtained, and this can be used as a host material or a peripheral compound.
  • the host material it is also a bipolar character (flow good both holes and electrons) may be a unipolar resistance, but high excited triplet energy level E T1 than the light emitting material Is preferable.
  • a more preferred host material has bipolarity and has a higher excited triplet energy level E T1 than the light emitting material.
  • preferable compounds as materials that can be further added are given.
  • it can be added as a stabilizing material.
  • the organic EL element of the present invention can be applied to any of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix.
  • the organic light emitting device such as the organic EL device of the present invention can be further applied to various applications.
  • Organic EL device of the present invention can also be applied to organic electroluminescence lighting and backlight, which are in great demand.
  • the organic light emitting device of the present invention can be applied to an organic light emitting diode.
  • the learning compounds S1 to S4 were synthesized according to the following documents. S1: Nature, 2012, 482, 234 S2: Materials Horizons, 2016, 3 (2), 145 S3: Nature, 2012, 492, 234 S4: International Publication No. 2018/047948
  • the learning compounds S5 to S7 were synthesized as follows. For each of S1 to S7, the maximum emission wavelength (emission maximum wavelength) due to the peak top of the emission spectrum when a thin film (thickness 50 nm) adjusted to be 10% by mass with respect to the host material (PPT) is irradiated with excitation light of 280 nm. ⁇ max) was measured.
  • the precipitated yellow-white crystals were collected by filtration and further washed with chloroform to obtain learning compound S7 (3.23 g, yield 99%).
  • the 1 H NMR spectrum and the 19 F NMR spectrum of the learning compound S7 are shown in FIGS. 3A and 3C, respectively.
  • the prediction model of the emission maximum wavelength was created by two steps of (1) extraction of the descriptor related to the emission maximum wavelength and (2) creation of the regression equation using the learning data.
  • descriptors are created using Rdkit (Open-source cheminformatics; http://www.rdkit.org), 200 types of descriptor values are used for each compound of the training data based on the chemical structural formula. Was calculated and converted into a 200-dimensional vector.
  • the 200 types of descriptors include descriptors representing the number of functional groups, topology, polarity, and the like.
  • the descriptor also includes HOMO-LUMO Gap.
  • HOMO-LUMO Gap is the value obtained by calculating the energy levels of HOMO and LUMO of the compound of the training data by quantum chemistry calculation using Gaussian 09 Rev.D, and subtracting the HOMO level from the calculated LUMO level. is there.
  • Quantum chemistry calculations are performed by the density functional theory, B3LYP is used for the functionals, 6-31g (d, p) is used for the basis functions, and the structure is based on the functionals and basis functions for the calculation of energy levels. The molecular structure that was optimized for was used. In addition, since the basic and highly versatile descriptor is preferentially used, the 3D descriptor is excluded. In addition, descriptors with the same value in more than 80% of the compounds of the training data were excluded because they are not suitable for creating normalization and regression equations.
  • x ij is the pre-conversion descriptor j of compound i
  • x'ij is the post-conversion descriptor j of compound i
  • ⁇ j is the mean of the entire descriptor j
  • ⁇ j is the standard deviation of the entire descriptor j.
  • V8 and V9 were synthesized according to the following documents.
  • V8 Materials, Horizons, 2016, 3 (2), 145 V9: Nature, 2012, 492, 234
  • ⁇ Verification of prediction model> The accuracy of the prediction model was evaluated using the verification data.
  • the prediction accuracy of the emission maximum wavelength of the verification compound was 14.3 nm when evaluated by RMSE.
  • the prediction accuracy of the verification compounds V8 and V9 was 15.4 nm when evaluated by RMSE.
  • RMSE is defined by the following formula. Note that n is the number of samples, y obs is the observed value, and y pred is the predicted value.
  • test compounds T1, T4, T10, T13, T19, T19-2, T21, T22, T25, T28, T31, and T34 were synthesized as follows.
  • the aromatic nucleophilic substitution reaction of the obtained fluoroaryl and carbazole analog is carried out in the presence of a base based on the following literature. Science Advances, 2018, 4 (6), eaao6910. Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399. Nature 2012, 492, 234. Organic letters, 2014, 16 (11), 3130. Tetrahedron letters, 2013, 54 (35), 4649.
  • FIGS. 10A and 10C The 1 H-NMR spectrum and the 19 F-NMR spectrum of the intermediate are shown in FIGS. 10A and 10C, respectively.
  • the method described in the following document may be used for the first step of the reaction. Chem. Rev. 2016, 116, 6837. Org. Lett. 2015, 17, 1042.
  • the NH portion of carbazole is phenylated based on the following literature. RSC advances 2015, 5 (77), 63130-63134. Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116 (15), 8699-8706. Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater .
  • FIGS. 11A and 11C The 1 H-NMR spectrum and the 19 F-NMR spectrum of the intermediate are shown in FIGS. 11A and 11C, respectively.
  • the method described in the following document may be used for the first step of the reaction. Chem. Rev. 2016, 116, 6837. Org. Lett. 2015, 17, 1042.
  • the NH portion of carbazole is phenylated based on the following literature. RSC advances 2015, 5 (77), 63130-63134. Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116 (15), 8699-8706. Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater .
  • test compound T28 (93 mg, yield 53%).
  • the 1 H-NMR spectrum, 19 F-NMR spectrum, and IR spectrum of the test compound T28 are shown in FIGS. 13A, 13B, and 13C, respectively.
  • the positions and intensities of the main peaks in the IR spectrum are as follows.
  • the 1 H-NMR spectrum, 19 F-NMR spectrum, and IR spectrum of the intermediate are shown in FIGS. 14A, 14C, and 14D, respectively.
  • the positions and intensities of the main peaks in the IR spectrum are as follows.
  • an intermediate 29 mg
  • carbazole 50 mg
  • cesium carbonate 390 mg
  • water 15 mL was added to the reaction solution, and the mixture was allowed to stand for 40 minutes.
  • HOMO HOMO
  • ⁇ E ST The ⁇ E ST of the test compounds T19, T19-2, T21, and T37 to T39 can be measured by the same method as the measurement method of ⁇ max (actual measurement), and the fluorescence spectrum (room temperature) and the phosphorescence spectrum (77K) can be measured. It was measured and calculated from the difference in wavelength at each rising edge.
  • the relative emission intensities of the test compounds T37 to T39 were measured by a conventional device (for example, "PMA12” manufactured by Hamamatsu Photonics Co., Ltd.).
  • the delayed fluorescence lifetimes of the test compounds T19, T19-2, T21, and T37 to T39 were measured by a conventional device (for example, "PMA12” manufactured by Hamamatsu Photonics Co., Ltd.).
  • the excited state stability of the test compounds T37 and T38 was determined by using a toluene solution of the compound (concentration 1.0 ⁇ 10 -5 M), degassing by argon bubbling, and then stirring with excitation light (wavelength 300 to 400 nm,). It was evaluated by irradiating with 5 mW / cm 2 ) and measuring the time from the initial emission to the reduction of the emission intensity by half.
  • the maximum emission wavelength was actually measured, and the measured values showed the same tendency as the predicted values.
  • the test compound T19 has a lower HOMO, a smaller ⁇ E ST , and a shorter delayed fluorescence lifetime than T20 or T21, and is therefore excellent in compatibility with peripheral materials and durability.
  • the test compounds T37 and T38 have a lower HOMO, a smaller ⁇ E ST , a larger emission intensity, and a shorter delayed fluorescence lifetime than T39, and thus are excellent in compatibility with peripheral materials and durability.

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Abstract

L'invention fournit un composé hétérocyclique à teneur en azote possédant un groupe perfluoroalkyle et une application de celui-ci, lequel composé possède une longueur d'onde d'émission adéquate. Le composé hétérocyclique à teneur en azote possédant un groupe perfluoroalkyle de l'invention possède N cycles carbazole (N étant un nombre entier supérieur ou égal à 2). Deux cycles carbazole adjacents sont liés par (A) une liaison directe, (B) une liaison via un groupe de liaison π conjugué, ou (C) une liaison condensée. Le nombre total de groupes perfluoroalkyle substitué par N cycles carbazole, est supérieur ou égal à 1 et inférieur à 2N.
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