WO2022196612A1 - Composé aromatique polycyclique - Google Patents

Composé aromatique polycyclique Download PDF

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WO2022196612A1
WO2022196612A1 PCT/JP2022/011215 JP2022011215W WO2022196612A1 WO 2022196612 A1 WO2022196612 A1 WO 2022196612A1 JP 2022011215 W JP2022011215 W JP 2022011215W WO 2022196612 A1 WO2022196612 A1 WO 2022196612A1
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substituted
unsubstituted
bonded
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compound
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PCT/JP2022/011215
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琢次 畠山
彰英 水谷
健永 前田
大輔 井上
真人 東
凌 南
孝弘 小林
裕之 田中
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学校法人関西学院
エスケーマテリアルズジェイエヌシー株式会社
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Priority to KR1020237032540A priority Critical patent/KR20230156725A/ko
Priority to JP2023507084A priority patent/JPWO2022196612A1/ja
Priority to CN202280020465.6A priority patent/CN116964063A/zh
Publication of WO2022196612A1 publication Critical patent/WO2022196612A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

Definitions

  • the present invention relates to polycyclic aromatic compounds.
  • the invention particularly relates to polycyclic aromatic compounds containing nitrogen and boron.
  • the present invention also relates to an organic device material, an organic electroluminescence device, a display device and a lighting device containing the polycyclic aromatic compound.
  • An organic electroluminescent element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound.
  • Layers containing organic compounds include light-emitting layers and charge transport/injection layers that transport or inject charges such as holes and electrons.
  • Various organic materials suitable for these layers have been developed.
  • Patent Documents 1 to 5 disclose that polycyclic aromatic compounds containing boron are useful as materials for organic electroluminescent devices and the like. An organic electroluminescent device containing this polycyclic aromatic compound is reported to have good external quantum efficiency.
  • Patent Documents 2 and 3 disclose structures in which heterocycles such as benzothiophene are condensed.
  • Patent Documents 4 and 5 disclose structures having cycloalkyl as a substituent.
  • An object of the present invention is to provide novel compounds useful as materials for organic devices such as organic EL elements.
  • the present inventors have made intensive studies to solve the above problems, and have found that by combining specific condensed ring structures and substituents in the structures of the compounds described in Patent Documents 1 to 5, there are many compounds that provide high luminous efficiency and the like. Succeeded in producing cyclic aromatic compounds. Further, the present inventors have found that an excellent organic EL device can be obtained by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes to form an organic EL device, and completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, organic device materials, etc. containing the following polycyclic aromatic compounds.
  • the present invention specifically has the following configurations.
  • the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are single bonds or linked via a linking group, Two adjacent R 11 are bonded to each other to form an aryl ring or heteroaryl ring or not, and at least one hydrogen of the formed aryl ring and heteroaryl ring is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl,
  • Each Z g is independently N or C—R g , and each R g is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, and two aryls of the diarylamino are not bonded to each other or are bonded via a linking group; , two heteroaryls of the diarylamino are not
  • the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are a single bond or a linking group are coupled via provided that any one Z g in each formula is a carbon bonded to N;
  • A is >O, >NR, >Si(-R) 2 , >S, or >Se, and R in the above >NR and above >Si(-R) 2 is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and the two Rs in >Si(—R) 2 are bonded to each other; or not forming a ring; at least one of the aryl or heteroaryl rings in the structure may or may not be fused with at least one cycl
  • the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are single bonds or linked via a linking group, Two adjacent R 11 are bonded to each other to form an aryl ring or heteroaryl ring or not, and at least one hydrogen of the formed aryl ring and heteroaryl ring is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl,
  • ⁇ 3> The polycyclic aromatic compound according to ⁇ 2>, wherein the structural unit represented by formula (1) is represented by formula (1a).
  • L CY is substituted or unsubstituted 1,4-phenylene, substituted or unsubstituted 4,4′-biphenylylene, substituted or unsubstituted 4,4′′-terphenylylene, and R CY is unsubstituted
  • ⁇ 5> The polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 4>, wherein one of X 1 and X 2 is >N-GA.
  • Me is methyl
  • tBu is t-butyl
  • D is deuterium
  • Me is methyl
  • tBu is t-butyl
  • D is deuterium
  • ⁇ 12> The organic electroluminescence device according to ⁇ 11>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.
  • ⁇ 13> A display device or lighting device comprising the organic electroluminescence device according to any one of ⁇ 10> to ⁇ 12>.
  • the present invention provides a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescent elements.
  • the polycyclic aromatic compound of the present invention can be used for producing organic devices such as organic electroluminescence devices.
  • FIG. 3 is an energy level diagram showing the energy relationship between a host, an assisting dopant and an emitting dopant in a TAF device using a general fluorescent dopant.
  • FIG. 2 is an energy level diagram showing an example of the energy relationship among a host, an assisting dopant, and an emitting dopant in an organic electroluminescence device of one embodiment of the present invention.
  • substituted with substituent A means that “substituent B having Y carbon atoms” is substituted with “substituent A (with no carbon number limitation)”.
  • the carbon number Y is not the total carbon number of the substituents A and B.
  • adjacent in this specification refers to the same rings that are adjacent.
  • a substituent may be substituted with a further substituent.
  • Substituents are sometimes described as “substituted or unsubstituted”). This is whether at least one hydrogen of a substituent (“first substituent” or “first substituent”) is replaced with a further substituent (“second substituent” or “second substituent”) , or means not replaced.
  • first substituent first substituent
  • second substituent second substituent
  • the polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1).
  • the polycyclic aromatic compound of the present invention has a high emission quantum yield (PLQY), a narrow emission half width, and excellent color purity.
  • the two R's in 2 may or may not be linked together to form a ring.
  • aryl, heteroaryl, alkyl and cycloalkyl are referred to as first substituents. Although these groups are described as "substituted or unsubstituted,” aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl are preferred if at least one hydrogen is substituted. These aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl are referred to as second substituents.
  • Each R 11 of C—R 11 is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl.
  • aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, and substituted silyl are referred to as first substituents.
  • these groups are described as "substituted or unsubstituted," aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl are preferred if at least one hydrogen is substituted.
  • secondary substituents aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl groups are referred to as secondary substituents.
  • R 11 is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted silyl. preferable.
  • each Z independently represents C—R 11 .
  • the R 11 at the para-position of Y 1 on the benzene ring is hydrogen or a substituent other than hydrogen, and the other R 11 is hydrogen.
  • ring B it is more preferable that R 11 at the para-position of Y 1 on the benzene ring is a substituent other than hydrogen, and other R 11 are hydrogen.
  • substituent at this time examples include the preferred substituents described later as the first substituent, such as tertiary-alkyl represented by formula (tR) (t-butyl or t-amyl, etc.), cycloalkyl, formula ( Examples include tertiary-alkyl represented by tR) or diarylamino or arylheteroarylamino optionally substituted with alkyl.
  • tR tertiary-alkyl represented by formula (tR) (t-butyl or t-amyl, etc.)
  • cycloalkyl formula
  • Examples include tertiary-alkyl represented by tR) or diarylamino or arylheteroarylamino optionally substituted with alkyl.
  • the R 11 at the para-position of Y 1 on the benzene ring is hydrogen or alkyl (such as methyl or t-butyl) and the other R 11 is hydrogen.
  • Two adjacent R 11 may combine with each other to form an aryl ring or heteroaryl ring.
  • At least one hydrogen of the formed aryl ring and heteroaryl ring is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, or unsubstituted.
  • the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl , or substituted silyl.
  • these groups are described as "substituted or unsubstituted," aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl are preferred if at least one hydrogen is substituted.
  • the aryl ring to be formed is preferably a benzene ring, naphthalene ring, indene ring or cyclopentadiene ring
  • the heteroaryl ring to be formed is preferably a thiophene ring, a pyrrole ring, a furan ring, a benzothiophene ring, a benzofuran ring or an indole ring.
  • a ring is preferred.
  • ring C is a ring structure represented by formula (C).
  • formula ( C ) any two consecutive ZCs are carbons, one of which is bonded to Y1, and the other is the carbon bonded to X2. .
  • This means that any two consecutive Z C 's in the c1 ring may be bonded to either Y 1 and X 2
  • any two consecutive Z C 's in the c2 ring may be bonded to Y 1 and X 2, as described below. It means that it may be combined with any of X2 . Its preferred form is shown below.
  • Z c is independently all C -R 11 is preferred, and in formula (1c), formula (1d), formula (1e), formula (1f), formula (1g) and formula (1h), each Z c of the c2 ring is independently and are all C—R c , and as described later, a form in which adjacent R c are bonded to each other to form an aryl ring (preferably a benzene ring) is also preferred.
  • formula (1a), formula (1b), formula (1c), formula (1d), formula (1e), formula (1f), formula (1g) and formula (1h), formula (1a), formula (1b) is preferred and formula (1a) is most preferred. Note that the descriptions of this specification, which will be described later, can be referred to for the description of each symbol and phrase.
  • X c is >O, >NR, >C(-R) 2 , >Si(-R) 2 , >S, or >Se;
  • R in C(-R) 2 and >Si(-R) 2 is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted and the two R's of >C(-R) 2 and >Si(-R) 2 are bonded to each other to form a ring or not.
  • Two R's in the above >C(-R) 2 and the above >Si(-R) 2 are bonded to each other to form a ring or not.
  • each Z C is independently N or C—R C , and each R C is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl.
  • Two adjacent R 4 C may be bonded together to form an aryl ring or heteroaryl ring.
  • At least one hydrogen of the formed aryl ring and heteroaryl ring is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, or unsubstituted.
  • the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl , or substituted silyl.
  • these groups are described as "substituted or unsubstituted," aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl are preferred if at least one hydrogen is substituted.
  • the aryl ring to be formed is preferably a benzene ring, naphthalene ring, indene ring or cyclopentadiene ring
  • the heteroaryl ring to be formed is preferably a thiophene ring, a pyrrole ring, a furan ring, a benzothiophene ring, a benzofuran ring or an indole ring.
  • a ring is preferred, and a benzene ring is most preferred.
  • Z C of the c2 ring are each independently N or C—R C and adjacent C—R C bonds are preferably formed to form an aryl ring or a heteroaryl ring (preferably an aryl ring, more preferably a benzene ring). This preferred form is shown below. Definition of each sign of formula (1c-2), formula (1d-2), formula (1e-2), formula (1f-2), formula (1g-2) and formula (1h-2), and their preferred Regarding the ranges, reference can be made to the explanations of formula (1c), formula (1d), formula (1e), formula (1f), formula (1g) and formula (1h).
  • R in the above Si—R and Ge—R is aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms.
  • R of Si--R and Ge--R in Y 1 of Formula (1) is aryl, alkyl or cycloalkyl, and examples of aryl, alkyl or cycloalkyl include the groups described above.
  • aryl having 6 to 10 carbon atoms eg, phenyl, naphthyl, etc.
  • alkyl having 1 to 5 carbon atoms eg, methyl, ethyl, etc.
  • cycloalkyl having 5 to 10 carbon atoms preferably cyclohexyl and adamantyl.
  • one of X 1 and X 2 is >NL CY -R CY and the other is >N-GA or >N-GB.
  • CY in NL CY -R CY is substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene, and substituted or unsubstituted or substituted or unsubstituted heteroarylene, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylylene, substituted or unsubstituted terphenylylene, substituted or unsubstituted more preferably fluorenylene or substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted 1,4-phenylene, substituted or unsubstituted 4,4'-biphenylylene, substituted or unsubstituted 4,4''-Terphenylylene is more preferred.
  • a group in which any one phenylene in these divalent groups is replaced with naphthylene is also preferred. Although these groups are described as "substituted or unsubstituted,” aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl are preferred if at least one hydrogen is substituted. Aryl and alkyl (particularly methyl, or tR described later) are more preferred. They may be further substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Reference can be made to the descriptions in the specification for the first substituent and the second substituent, as well as the terms used herein and their preferred ranges. The substituents referred to as "substituted or unsubstituted” are particularly preferably alkyl or aryl optionally substituted with alkyl, more preferably methyl or phenyl optionally substituted with methyl.
  • R CY is substituted or unsubstituted cycloalkyl, preferably substituted or unsubstituted adamantyl, most preferably unsubstituted adamantyl.
  • Adamantyl is preferably 1-adamantyl in any case.
  • >N-L CY -R CY is represented by the following formulas (CY-1) to (CY-13). In formulas (CY-1) to (CY-13), at least one hydrogen in the moiety corresponding to L CY is substituted or unsubstituted as described above. Among formulas (CY-1) to (CY-10), formula (CY-1), formula (CY-7), formula (CY-8) or formula (CY-9) is preferable, and formula (CY-1 ) or formula (CY-7) is more preferred.
  • GA is a group represented by formula (GA)
  • GB is a group represented by formula (GB).
  • An example of the formula (GB) is the following formula (GB').
  • each Z g is independently N or C—R g
  • each R g of C—R g is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl.
  • Rg is preferably aryl or alkyl (especially tR described later), and most preferably alkyl (especially tR described later).
  • Rg is preferably aryl or alkyl (especially tR described later), and most preferably alkyl (especially tR described later).
  • Rg is preferably aryl or alkyl (especially tR described later), and most preferably alkyl (especially tR described later).
  • 0 to 3 R a are substituents other than hydrogen
  • other R a are preferably hydrogen
  • 0 to 2 R a are other than hydrogen
  • the other R a is hydrogen, more preferably 0 to 1 R a is a substituent other than hydrogen and the other R a is hydrogen.
  • Two adjacent R g in each formula may be bonded together to form an aryl ring or heteroaryl ring, and at least one hydrogen in the formed aryl ring and heteroaryl ring is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted substituted or unsubstituted with substituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted arylthio not Although these groups are described as "substituted or unsub
  • any one Z g is a carbon bonded to N, which is X 1 or X 2 .
  • the bond exists on the g1 ring or the g2 ring.
  • A is >O, >NR, >Si(-R) 2 , >S, or >Se
  • R in the above >NR and above >Si(-R) 2 is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two Rs in >Si(—R) 2 are bonded to each other; may or may not form a ring.
  • formula (GA) examples include, for example, forms represented by any one of the following formulas (GA-1) to (GA-52). However, it is not limited to these examples.
  • * represents the bonding position with N of >N - GA, which is X1 or X2. At least one hydrogen in Formulas (GA-1) through (GA-52) is substituted or unsubstituted as described above.
  • formulas (GA-1) to (GA-52), formula (GA-1), formula (GA-4), formula (GA-5), formula (GA-6), formula (GA-7), Formula (GA-8), formula (GA-9), formula (GA-10), formula (GA-11), formula (GA-12), or formula (GA-13) is preferred, and formula (GA-1 ), formula (GA-5), formula (GA-10) or formula (GA-11) is more preferred, and formula (GA-1) or formula (GA-5) is most preferred.
  • formulas (GB-1) to (GB-14) formula (GB-1), formula (GB-2), formula (GB-3), formula (GB-6), formula (GB-7), Formula (GB-8), formula (GB-9), formula (GB-10), formula (GB-12), formula (GB-13), or formula (GB-14) is preferred, and formula (GB-1 ), formula (GB-3), formula (GB-5), formula (GB-6), formula (GB-7), formula (GB-10), formula (GB-13) or formula (GB-14) is more preferred, and formula (GB-1), formula (GB-3), formula (GB-6), formula (GB-13) or formula (GB-14) is most preferred.
  • the polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) and its preferred forms.
  • Examples of the polycyclic aromatic compound having a structure composed of one of the above structural units include the polycyclic aromatic compound represented by the formula explained above as the structural unit represented by formula (1).
  • polycyclic aromatic compound having a structure consisting of two or more structural units represented by formula (1) polycyclic aromatic compounds represented by the above-described formulas as structural units represented by formula (1) compounds corresponding to multimers of group compounds.
  • the multimer is preferably a 2- to 6-mer, more preferably a 2- to 3-mer, and particularly preferably a dimer.
  • the multimer may be in a form having a plurality of the above unit structures in one compound, and any ring (A ring, B ring or C ring) contained in the above structural unit may be shared by a plurality of unit structures. It may be in a form in which any rings (A ring, B ring or C ring) included in the unit structure are condensed and bonded.
  • the above unit structure may be in a form in which a plurality of units are bonded by a single bond, a linking group such as alkylene having 1 to 3 carbon atoms, phenylene, naphthylene, or the like. Among these, preferred is a form in which the ring is shared.
  • a cycloalkane having 3 to 24 carbon atoms may be used as the cycloalkane. At least one hydrogen in the cycloalkane at this time is substituted with aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. and at least one —CH 2 — in the cycloalkane may be replaced with —O—, but cycloalkanes in which all —CH 2 — are preferred.
  • At least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms.
  • at least one hydrogen in the cycloalkane is substituted with aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 22 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms; is preferably a cycloalkane having a higher
  • Cycloalkane includes cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, Examples include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, cycloalkanes having 6 carbon atoms, and the like.
  • cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, Adamantane, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (especially methyl)-substituted, halogen (especially fluorine)-substituted and deuterium-substituted products thereof having 1 to 5 carbon atoms are mentioned.
  • the carbon adjacent to the carbon of the condensation site, corresponding to the benzyl position is shown in the structural formula below.
  • ) is preferably a structure in which at least one hydrogen is substituted, more preferably a structure in which two hydrogens at the ⁇ -position carbon are substituted, and a structure in which a total of four hydrogens at two ⁇ -position carbons are substituted is even more preferable. . This is to protect the chemically active sites and improve the durability of the compound.
  • substituents examples include alkyl (especially methyl)-substituted ones having 1 to 5 carbon atoms, halogen (especially fluorine)-substituted ones and deuterium-substituted ones.
  • alkyl (especially methyl)-substituted ones having 1 to 5 carbon atoms examples include alkyl (especially methyl)-substituted ones having 1 to 5 carbon atoms, halogen (especially fluorine)-substituted ones and deuterium-substituted ones.
  • a structure in which a partial structure represented by the following formula (Z-11) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring is preferred.
  • Me represents methyl and * represents the bonding position.
  • the number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
  • examples in which one benzene ring (phenyl) is condensed with one or more cycloalkanes are shown below. * indicates a bonding position, which may be any carbon that constitutes a benzene ring and does not constitute a cycloalkane.
  • the condensed cycloalkanes of formula (Cy-1-4) and formula (Cy-2-4) may be condensed.
  • ring (group) to be condensed is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, is also the same.
  • At least one —CH 2 — in the cycloalkane may be replaced with —O—.
  • examples in which one or more —CH 2 — in a cycloalkane condensed to one benzene ring (phenyl) are replaced with —O— are shown below. Even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even if there is, it is the same.
  • At least one hydrogen in the cycloalkane may be substituted, such as aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy. , aryloxy, substituted silyl, deuterium, cyano or halogen, the details of which can be referred to the description of the first substituent herein.
  • alkyl eg, alkyl having 1 to 6 carbon atoms
  • cycloalkyl eg, cycloalkyl having 3 to 14 carbon atoms
  • halogen eg, fluorine
  • deuterium are preferred.
  • cycloalkyl when cycloalkyl is substituted, it may be in a form of substitution forming a spiro structure, an example of which is shown below.
  • rings A, B and C in a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) are cycloalkanes. Condensed forms are mentioned.
  • cycloalkane condensation include polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), and preferred forms thereof, X 1 or X 2 A form containing a ring fused to L CY with a cycloalkane in which either one is >NL CY -R CY , or >N-GA in which either one of X 1 or X 2 is GA or > A form containing a cycloalkane-fused ring to GB of N-GB, a cycloalkane-fused diarylamino, a cycloalkane-fused carbazolyl (fused to this benzene ring portion) or a cycloalkane-fused benzo Examples are given with carbazolyl (fused to this benzene ring moiety).
  • diarylamino the groups explained as the above-mentioned "first substituent" can be mentioned.
  • a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1), a preferred form thereof, and the above cycloalkane condensation are in the A ring, B ring, or C ring
  • a condensed form is preferred, and a condensed form on the B ring or C ring is more preferred.
  • a form in which both the B ring and the C ring are condensed is also preferred.
  • hydrogen in the structure consisting of one or more of the structural units represented by formula (1) and preferred forms thereof is wholly or partially substituted with deuterium, cyano, or halogen; or not replaced.
  • a ring, B ring, C ring, a substituent for A to C rings, Y 1 R ( alkyl, cycloalkyl, aryl) when is Si—R or Ge—R, and L CY or R CY of >NL CY —R CY of one of X 1 and X 2 ,
  • the hydrogens in GA of >N-GA or GB of >N-GB of one of X 1 and X 2 may be replaced with deuterium, cyano or halogen, among which all or one in aryl or heteroaryl
  • An embodiment in which partial hydrogen is replaced with deuterium, cyano, or halogen is exemplified.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, even more preferably fluorine.
  • a form in which hydrogen is replaced with deuterium is preferable because it improves the stability of the compound.
  • one hydrogen is replaced by deuterium, more preferably multiple hydrogens are replaced by deuterium, more preferably all hydrogens in the aromatic moiety are replaced by deuterium, all hydrogens are replaced by deuterium. is most preferred.
  • aryl ring examples include an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and an aryl ring having 6 to 10 carbon atoms.
  • Aryl rings are particularly preferred.
  • aryl rings include monocyclic benzene ring, bicyclic biphenyl ring, condensed bicyclic naphthalene ring and indene ring, tricyclic terphenyl ring (m-ter phenyl, o-terphenyl, p-terphenyl), condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, condensed tetracyclic triphenylene ring, pyrene ring, naphthacene ring, Examples include a chrysene ring, a condensed pentacyclic perylene ring, and a pentacene ring.
  • the fluorene ring, benzofluorene ring, and indene ring also include structures in which fluorene rings, benzofluorene rings, cyclopentane rings, and the like are spiro-bonded, respectively.
  • fluorene ring, the benzofluorene ring and the indene ring two of the two hydrogen atoms of methylene are respectively substituted with alkyl such as methyl as the first substituent described later to form a dimethylfluorene ring and a dimethylbenzofluorene ring. and those with a dimethylindene ring and the like are also included.
  • heteroaryl ring examples include a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, more preferably a heteroaryl ring having 2 to 20 carbon atoms, Heteroaryl rings with 2 to 15 carbon atoms are more preferred, and heteroaryl rings with 2 to 10 carbon atoms are particularly preferred.
  • heteroaryl ring examples include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • heteroaryl rings include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring , cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine
  • dihydroacridine ring, xanthene ring, and thioxanthene ring two of the two hydrogens in methylene are respectively substituted with alkyl such as methyl as the first substituent described below, resulting in a dimethyldihydroacridine ring, dimethyl Those having a xanthene ring, a dimethylthioxanthene ring, or the like are also preferable.
  • Bipyridine ring phenylpyridine ring and pyridylphenyl ring which are bicyclic ring systems, and terpyridyl ring, bispyridylphenyl ring and pyridylbiphenyl ring which are tricyclic systems are also mentioned as “heteroaryl ring”.
  • a pyran ring shall also be contained in a "heteroaryl ring.”
  • At least one hydrogen in the above “aryl ring” or “heteroaryl ring” is the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted “heteroaryl”, substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "alkenyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or "substituted silyl” may be substituted with
  • the "aryl” is a monovalent group obtained by removing one hydrogen from the above-mentioned "aryl ring".
  • Examples include aryl having 6 to 30 carbon atoms, and aryl having 6 to 24 carbon atoms.
  • Aryl having 6 to 20 carbon atoms is more preferable, aryl having 6 to 16 carbon atoms is more preferable, aryl having 6 to 12 carbon atoms is particularly preferable, and aryl having 6 to 10 carbon atoms is most preferable.
  • heteroaryl is a monovalent group in which one hydrogen is removed from the above-mentioned "heteroaryl ring”, examples thereof include heteroaryl having 2 to 30 carbon atoms, Heteroaryl is preferred, heteroaryl having 2 to 20 carbon atoms is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred.
  • Heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • aryl and heteroaryl in each of "substituted or unsubstituted diarylamino", “substituted or unsubstituted diheteroarylamino", and “substituted or unsubstituted arylheteroarylamino" as the first substituent are Those described as “aryl” and “heteroaryl” can be cited along with their preferred ranges.
  • diarylamino two aryls are not bonded to each other or are bonded via a linking group.
  • a diheteroarylamino two heteroaryls are either not attached to each other or are attached through a linking group.
  • arylheteroarylamino the aryl and heteroaryl are either not attached to each other or are attached through a linking group.
  • linking groups include >O, >N—R X , >C(—R X ) 2 , >Si(—R X ) 2 , >S, >CO, >CS, >SO, >SO 2 and >Se, and each R X is independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl, and >C Two R X in each of (-R X ) 2 and >Si(-R X ) 2 may be bonded to each other via a single bond or a linking group X Y to form a ring.
  • X Y is >O, >N-R Y , >C(-R Y ) 2 , >Si(-R Y ) 2 , >S, >CO, >CS, >SO, >SO 2 , and >Se and each R Y is independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl.
  • X Y is >C(-R Y ) 2 and >Si(-R Y ) 2
  • the two R Y are not combined to form a further ring.
  • Further examples of linking groups include alkenylene.
  • Any hydrogen of said alkenylene may each independently be substituted with R 2X , each R 2X independently being alkyl, cycloalkyl, substituted silyl, aryl and heteroaryl, which are alkyl, cycloalkyl, It may be substituted with substituted silyl or aryl.
  • Alkyl as the first substituent may be either straight-chain or branched-chain, for example, straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms.
  • Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 8 carbon atoms (Branched chain alkyl having 3 to 8 carbon atoms) is more preferable, alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is particularly preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is more preferable. branched chain alkyl) are most preferred.
  • alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3 -tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-dec
  • tertiary-alkyl represented by the following formula (tR) is one of the particularly preferable substituents for the aryl ring or heteroaryl ring in rings A, B and C. is one. This is because such a bulky substituent increases the intermolecular distance, thereby improving the light emission quantum yield (PLQY). Further, a substituent in which a tertiary-alkyl represented by formula (tR) substitutes another substituent as a second substituent is also preferable.
  • tertiary-alkyl-substituted diarylamino represented by (tR) tertiary-alkyl-substituted carbazolyl (preferably N-carbazolyl) represented by (tR) or (tR) and benzocarbazolyl (preferably N-benzocarbazolyl) substituted with tertiary-alkyl represented.
  • “Diarylamino” includes the groups described as the "first substituent” below.
  • Substitution forms of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl include substitution of a group of formula (tR) for some or all hydrogens of the aryl ring or benzene ring in these groups.
  • substitution forms of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl include substitution of a group of formula (tR) for some or all hydrogens of the aryl ring or benzene ring in these
  • R a , R b , and R c are each independently alkyl having 1 to 24 carbon atoms, and any —CH 2 — in the alkyl may be substituted with —O—.
  • the group represented by formula (tR) replaces at least one hydrogen in the structure containing the structural unit represented by formula (1) in *.
  • C1-C24 alkyl of R a , R b and R c may be either linear or branched chain, for example, C 1-24 linear alkyl or C 3-24 branched Chain Alkyl, C1-C18 Alkyl (C3-C18 Branched Alkyl), C1-C12 Alkyl (C3-C12 Branched Alkyl), C1-C6 Alkyl (Cb branched chain alkyl having 3 to 6 carbon atoms) and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).
  • the total number of carbon atoms of R a , R b , and R c in formula (tR) of formula (1) is preferably 3 to 20 carbon atoms, particularly preferably 3 to 10 carbon atoms.
  • R a , R b , and R c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t -pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1- methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl,
  • Examples of groups represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1- methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1- dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1- methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylprop
  • cycloalkyl as the first substituent includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. , cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like.
  • cyclohexyl includes monocyclic cyclohexyl and the like as well as polycyclic cyclohexyl such as adamantyl, as enumerated later.
  • cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo [2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl , diamantyl, decahydronaphthalenyl, decahydroazulenyl, and alkyl (especially methyl)-substituted products thereof having 1 to 5 carbon atoms.
  • Alkenyl as the first substituent includes straight chain alkenyl having 2 to 24 carbon atoms or branched chain alkenyl having 4 to 24 carbon atoms. Alkenyl having 2 to 18 carbon atoms is preferred, alkenyl having 2 to 12 carbon atoms is more preferred, alkenyl having 2 to 6 carbon atoms is even more preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred. Specific examples of “alkenyl” include vinyl, allyl, butadienyl and the like.
  • Alkoxy as the first substituent includes, for example, straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and 1 to 6 carbon atoms. (branched alkoxy having 3 to 6 carbon atoms) is more preferred, and alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.
  • alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.
  • Aryloxy as the first substituent is a group in which the hydrogen of the --OH group is substituted with aryl, and the aryl and its preferred range can be cited from those described above.
  • Arylthio as the first substituent is a group in which the hydrogen of the --SH group is substituted with aryl, and the aryl and its preferred range can be cited from those described above.
  • Substituted silyl as the first substituent includes, for example, silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl and aryl. Examples include trialkylsilyls, tricycloalkylsilyls, dialkylcycloalkylsilyls, alkyldicycloalkylsilyls, triarylsilyls, dialkylarylsilyls, and alkyldiarylsilyls.
  • Examples of “trialkylsilyl” include groups in which three hydrogen atoms in silyl are each independently substituted with alkyl. can be quoted.
  • Preferred alkyl for substitution is alkyl having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, t-amyl and the like.
  • trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethyl Silyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethyl Silyl, t-amyldiethylsilyl, methyldi
  • tricycloalkylsilyl include groups in which three hydrogen atoms in a silyl group are each independently substituted with cycloalkyl.
  • the group described as "" can be cited.
  • Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[ 2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.
  • tricycloalkylsilyls include tricyclopentylsilyl and tricyclohexylsilyl.
  • dialkylcycloalkylsilyl substituted by 2 alkyl and 1 cycloalkyl and alkyldicycloalkylsilyl substituted by 1 alkyl and 2 cycloalkyl are selected from the above specific alkyl and cycloalkyl and silyl substituted with a group such as
  • dialkylarylsilyl substituted by 2 alkyl and 1 aryl alkyldiarylsilyl substituted by 1 alkyl and 2 aryl
  • triarylsilyl substituted by 3 aryl include the specific alkyl and silyl substituted with a group selected from aryl.
  • triarylsilyls include, in particular, triphenylsilyl.
  • aryl in the first substituent “diarylboryl” and its preferred range, the above description of aryl can be cited. Also, these two aryls may be bonded via a single bond or a linking group. Linking groups include, for example, >C(--R) 2 , >O, >S, and >NR.
  • R in >C(--R) 2 and >N--R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents);
  • the substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (these are the second substituents), and specific examples of these groups include the above-mentioned aryl as the first substituent, hetero References may be made to aryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy.
  • diarylboryl when simply referred to as “diarylboryl", unless otherwise specified, "the two aryls of said diarylboryl are not bonded to each other or via a single bond or a linking group" respectively. Suppose that the explanation "is connected” is added.
  • first substituent substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “diarylamino”, substituted or unsubstituted “di heteroarylamino”, substituted or unsubstituted “arylheteroarylamino", substituted or unsubstituted "diarylboryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkenyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy”, substituted or unsubstituted "arylthio", or substituted "silyl” are described as substituted or unsubstituted As such, at least one hydrogen in them may be replaced with a second substituent (second substituent).
  • the second substituent preferably includes aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl.
  • aryl preferably includes aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl.
  • aryl preferably includes aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl.
  • a structure substituted with cycloalkyl such as cyclohexyl is also included in the aryl or heteroaryl as the second substituent.
  • the second substituent is carbazolyl
  • carbazolyl in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also a second substituent.
  • heteroaryl as a substituent. This description can also be applied to the description of other first substituents and second substituents in this specification.
  • the emission wavelength can be adjusted by the steric hindrance, electron donating and electron withdrawing properties of the structure of the first substituent.
  • Groups represented by the following structural formulas are preferable, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4- xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6- dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl,
  • t-butyl t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl , 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6- Dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.
  • a polycyclic aromatic compound having a structure consisting of a structural unit represented by formula (1) and one or more of its preferred forms is a tertiary-alkyl (t- butyl, t-amyl, etc.), neopentyl or adamantyl, and preferably contains a tertiary-alkyl represented by formula (tR) (t-butyl, t-amyl, etc.).
  • tR tertiary-alkyl
  • tR tertiary-alkyl
  • PLQY light emission quantum yield
  • diarylamino is also preferable.
  • diarylamino substituted with a group of formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a group of formula (tR) or benzocarbazolyl substituted with a group of formula (tR) ( N-benzocarbazolyl) is also preferred.
  • Substitution forms of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl include substitution of a group of formula (tR) for some or all hydrogens of the aryl ring or benzene ring in these groups.
  • substitution forms of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl include substitution of a group of formula (tR) for some or all hydrogens of the aryl ring or benzene ring in these groups.
  • substitution forms of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl include substitution of a group of formula (tR
  • polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds.
  • “Me” represents methyl
  • “tBu” represents t-butyl
  • “tAm” represents t-amyl
  • “D” represents deuterium.
  • the following structure is an example.
  • the polycyclic aromatic compound of the present invention can be produced by the following procedure.
  • Method for producing polycyclic aromatic compound> Having a structure consisting of one or more structural units represented by formula (1) or formula (2) is basically first composed of A ring (a ring) and B ring (b ring) and C A ring (c ring) is bonded with a bonding group (a group containing X 1 or X 2 ) to produce an intermediate (first reaction), and then A ring (a ring), B ring (b ring ) and the C ring (c ring) with a linking group ( a group containing Y1) to produce the final product (second reaction).
  • the first reaction for example, general reactions such as nucleophilic substitution reaction and Ullmann reaction can be used for the etherification reaction, and general reactions such as the Buchwald-Hartwig reaction can be used for the amination reaction.
  • a tandem hetero Friedel-Crafts reaction continuous aromatic electrophilic substitution reaction, hereinafter the same
  • at least one ring selected from the group consisting of A ring, B ring and C ring is is a condensed ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.
  • the polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each step below, reference can be made to the description of International Publication No. 2015/102118.
  • the reaction including the reaction step of connecting the B ring and the C ring in 1 is described below.
  • Metallation reagents used in the halogen-metal exchange reaction in the schemes described so far include alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, t-butyllithium, isopropylmagnesium chloride, bromide
  • alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, t-butyllithium
  • isopropylmagnesium chloride bromide
  • the metalating reagents used in the orthometal exchange reaction in the schemes explained so far include lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexa Organic alkali compounds such as methyldisilazide, lithium tetramethylpiperidinylmagnesium chloride/lithium chloride complex, and lithium tri-n-butylmagnesate can be mentioned.
  • additives that promote the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, Examples include N,N-dimethylpropylene urea.
  • Lewis acids used in the schemes described so far include AlCl 3 , AlBr 3 , AlF 3 , BF 3 OEt 2 , BCl 3 , BBr 3 , GaCl 3 , GaBr 3 , InCl 3 , InBr 3 , In (OTf) 3 , SnCl4, SnBr4 , AgOTf, ScCl3 , Sc(OTf) 3 , ZnCl2 , ZnBr2 , Zn(OTf) 2 , MgCl2, MgBr2 , Mg(OTf) 2 , LiOTf , NaOTf, KOTf, Me3SiOTf , Cu(OTf) 2 , CuCl2 , YCl3, Y(OTf) 3 , TiCl4 , TiBr4 , ZrCl4 , ZrBr4 , FeCl3, FeBr3 , CoCl3 , CoBr3 and the like. be done
  • Bronsted acids used in the schemes described so far include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboronic acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride and the like.
  • solid Bronsted acids include Amberlyst (trade name: Dow Chemical), Nafion (trade name: DuPont), Zeolite, and Teikacure (trade name: Tayca Co., Ltd.).
  • amines that may be added in the schemes explained so far include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N , N-dimethylaniline, pyridine, 2,6-lutidine, 2,6-di-t-butylamine and the like.
  • Solvents used in the schemes described so far include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4 -trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-t-butyl ether and the like.
  • Bronsted bases or Lewis acids may be used in the above schemes to facilitate the tandem hetero Friedel-Crafts reaction.
  • a Y 1 halide such as Y 1 trifluoride, Y 1 trichloride , Y 1 tribromide, Y 1 triiodide, etc.
  • hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, so the use of a Bronsted base that scavenges the acid is effective.
  • the polycyclic aromatic compound of the present invention also includes compounds in which at least some of the hydrogen atoms are substituted with deuterium or cyano, and compounds in which halogens such as fluorine and chlorine are substituted.
  • halogens such as fluorine and chlorine are substituted.
  • Such compounds can be synthesized in the same manner as described above by using starting materials deuterated, cyanated, fluorinated or chlorinated at desired positions.
  • Organic device The polycyclic aromatic compound of the present invention can be used as an organic device material.
  • Organic devices include, for example, organic electroluminescence devices, organic field effect transistors, organic thin film solar cells, and the like.
  • the polycyclic aromatic compound and polymer thereof according to the present invention can be used as materials for organic devices.
  • Organic devices include, for example, organic electroluminescence elements, organic field effect transistors, organic thin-film solar cells, and the like, and organic electroluminescence elements are preferred.
  • the polycyclic aromatic compound and multimer thereof according to the present invention are preferably organic electroluminescent device materials, more preferably light emitting layer materials (light emitting materials), and dopant materials for light emitting layers. Most preferred.
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.
  • the organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a The hole-transport layer 104 provided, the light-emitting layer 105 provided over the hole-transport layer 104, the electron-transport layer 106 provided over the light-emitting layer 105, and the electron-transport layer 106 provided and a cathode 108 provided on the electron injection layer 107 .
  • the organic EL element 100 is fabricated in reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer 107 an electron transport layer 106 provided on the electron transport layer 106; a light emitting layer 105 provided on the electron transport layer 106; a hole transport layer 104 provided on the light emitting layer 105; A structure having a hole-injection layer 103 provided at the bottom and an anode 102 provided on the hole-injection layer 103 may be employed.
  • All of the above layers are not indispensable, and the minimum structural unit is composed of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection Layer 107 is an optional layer.
  • each of the above layers may be composed of a single layer, or may be composed of a plurality of layers.
  • the layers constituting the organic EL element may include " substrate/anode/hole-transporting layer/luminescent layer/electron-transporting layer/electron-injecting layer/cathode”, “substrate/anode/hole-injecting layer/luminescent layer/electron-transporting layer/electron-injecting layer/cathode”, “substrate/ Anode/Hole Injection Layer/Hole Transport Layer/Light Emitting Layer/Electron Injection Layer/Cathode", "Substrate/Anode/Hole Injection Layer/Hole Transport Layer/Light Emitting Layer/Electron Transport Layer/Cathode", "Substrate/ Anode/light emitting layer/electron transport layer/electron injection layer/electron injection layer/
  • the polycyclic aromatic compound of the present invention is preferably used as a material forming one or more organic layers in an organic electroluminescent device, and more preferably used as a material forming a light-emitting layer.
  • the light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied.
  • any compound (light-emitting compound) that emits light when excited by recombination of holes and electrons can be used.
  • the polycyclic aromatic compound of the present invention can be used as a light-emitting layer material, and may be used as a dopant material or as a host material, but is preferably used as a light-emitting layer material. It is more preferable to use as
  • dopant there is an example in which an assisting dopant and an emitting dopant are used in combination, but in the present specification, when simply described as “dopant", it refers to a light-emitting dopant used alone. .
  • the light-emitting layer may be either a single layer or multiple layers, each of which is formed of a light-emitting layer material (host material, dopant material).
  • the host material and the dopant material may be of one kind, or may be a combination of a plurality of them.
  • the dopant material may be included entirely or partially in the host material.
  • As a doping method it can be formed by a co-evaporation method with a host material, but it may be mixed with the host material in advance and then vapor-deposited simultaneously.
  • the polycyclic aromatic compound of the present invention can be preferably used as a dopant material.
  • Examples of dopant materials other than the polycyclic aromatic compounds of the present invention are shown below. It is also preferred to use the following dopant materials in combination with the polycyclic aromatic compounds of the present invention.
  • "Me” represents methyl
  • "tBu” represents t-butyl
  • "D" represents deuterium.
  • the amount of host material used varies depending on the type of host material, and should be determined according to the properties of the host material.
  • a guideline for the amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and still more preferably 90 to 99.9% by mass of the total material for the light-emitting layer. is.
  • the amount of dopant material used varies depending on the type of dopant material, and should be determined according to the characteristics of the dopant material.
  • a guideline for the amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass of the total light-emitting layer material. be.
  • the above range is preferable in that, for example, the phenomenon of concentration quenching can be prevented.
  • Host materials include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene, and fluorene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives, which have long been known as luminescent materials. , fluorene derivatives, and benzofluorene derivatives.
  • L 1 is arylene having 6 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms, heteroarylene arylene having 6 to 24 carbon atoms and Arylene heteroarylene arylene, preferably arylene having 6 to 16 carbon atoms, more preferably arylene having 6 to 12 carbon atoms, and particularly preferably arylene having 6 to 10 carbon atoms, specifically, benzene ring, biphenyl ring, Bivalent groups such as terphenyl rings and fluorene rings are included.
  • heteroarylene having 2 to 24 carbon atoms is preferable, heteroarylene having 2 to 20 carbon atoms is more preferable, heteroarylene having 2 to 15 carbon atoms is further preferable, and heteroarylene having 2 to 10 carbon atoms is particularly preferable.
  • Preferred specific examples include compounds represented by any of the structural formulas listed below.
  • at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (eg methyl or t-butyl), phenyl or naphthyl.
  • anthracene compound examples include compounds represented by formula (3-H) and compounds represented by formula (3-H2).
  • X and Ar 4 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, optionally substituted diheteroarylamino, substituted or unsubstituted substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, optionally substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted Arylthio or substituted silyl and not all X and Ar 4 are hydrogen at the same time. At least one hydrogen in the compound represented by formula (3-H) is substituted with halogen, cyano, deuterium or optionally substituted heteroaryl, or is unsubstituted.
  • a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure.
  • the unit structures represented by the formula (3-H) may be bonded through X, where X is a single bond, arylene (phenylene, biphenylene, naphthylene, etc.) and heteroarylene (pyridine a group having a divalent bond valence such as a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).
  • X is a single bond
  • arylene phenylene, biphenylene, naphthylene, etc.
  • heteroarylene pyridine a group having a divalent bond valence such as a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole
  • X is each independently a group represented by formula (3-X1), formula (3-X2) or formula (3-X3), and formula (3-X1), formula The group represented by (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3-H) at *.
  • two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two X's are not simultaneously a group represented by formula (3-X2).
  • a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure.
  • the unit structures represented by the formula (3-H) may be bonded through X, where X is a single bond, arylene (phenylene, biphenylene, naphthylene, etc.) and heteroarylene (pyridine a group having a divalent bond valence such as a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).
  • X is a single bond
  • arylene phenylene, biphenylene, naphthylene, etc.
  • heteroarylene pyridine a group having a divalent bond valence such as a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole
  • the naphthylene moiety in formulas (3-X1) and (3-X2) may be fused with one benzene ring.
  • the structure fused in this way is as follows.
  • Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or represented by formula (A) (including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl).
  • Ar 1 or Ar 2 is a group represented by formula (A)
  • the group represented by formula (A) is represented by * in formula (3-X1) or formula (3-X2). Bonds with the naphthalene ring.
  • Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyls).
  • Ar 3 is a group represented by formula (A)
  • the group represented by formula (A) is bonded to the single bond represented by the straight line in formula (3-X3) at *. . That is, the anthracene ring of formula (3-H) and the group represented by formula (A) are directly bonded.
  • Ar 3 may have a substituent, and at least one hydrogen in Ar 3 is further alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl , fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl).
  • the substituent of Ar 3 is a group represented by formula (A)
  • the group represented by formula (A) is bonded to Ar 3 in formula (3-X3) at *.
  • Ar 4 is each independently substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and/or cycloalkyl having 5 to 10 carbon atoms It is Cyril who is
  • alkyl having 1 to 4 carbon atoms to be substituted on silyl examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc.
  • Three hydrogen atoms in silyl are each independently is substituted with an alkyl of
  • sil substituted with alkyl having 1 to 4 carbon atoms include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl , propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyl diethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyld
  • Cycloalkyl having 5 to 10 carbon atoms substituted on silyl is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydro azulenyl and the like, and three hydrogens in silyl are each independently substituted with these cycloalkyls.
  • sil substituted with cycloalkyl having 5 to 10 carbon atoms include tricyclopentylsilyl and tricyclohexylsilyl.
  • Substituted silyl also includes dialkylcycloalkylsilyl substituted by 2 alkyl and 1 cycloalkyl and alkyldicycloalkylsilyl substituted by 1 alkyl and 2 cycloalkyl, substituted alkyl and cycloalkyl Specific examples of are the groups described above.
  • hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with a group represented by formula (A).
  • the group of formula (A) replaces at least one hydrogen in the compound of formula (3-H) at *.
  • the group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have.
  • Y is —O—, —S— or >N—R 29
  • R 21 to R 28 are each independently hydrogen, optionally substituted alkyl, or optionally substituted Cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tri cycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, wherein adjacent groups among R 21 to R 28 are bonded to each other to form a hydrocarbon ring; An aryl ring or heteroaryl ring may be formed, and R 29 is hydrogen or optionally substituted aryl.
  • Y in formula (A) is preferably -O-.
  • Alkyl of “optionally substituted alkyl” for R 21 to R 28 may be either straight chain or branched chain, for example, straight chain alkyl having 1 to 24 carbon atoms or alkyl having 3 to 24 carbon atoms. Branched chain alkyl can be mentioned.
  • Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 6 carbon atoms (Branched-chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms) is particularly preferable.
  • alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldec
  • Cycloalkyl of “optionally substituted cycloalkyl” for R 21 to R 28 includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms. , cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.
  • cycloalkyl examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (especially methyl)-substituted products thereof having 1 to 4 carbon atoms, norbornenyl, bicyclo [1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo [2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.
  • aryl of “optionally substituted aryl” for R 21 to R 28 includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, and aryl having 6 to 12 carbon atoms. is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred.
  • aryl includes monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, and tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl). , condensed tricyclic acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, condensed tetracyclic triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic ring perylenyl, pentacenyl, and the like.
  • heteroaryl of “optionally substituted heteroaryl” for R 21 to R 28 includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms. Heteroaryl having 2 to 20 carbon atoms is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • heteroaryl examples include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H- indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, pyrazo
  • alkoxy of “optionally substituted alkoxy” for R 21 to R 28 includes, for example, straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms.
  • Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and 1 to 6 carbon atoms. is more preferred (branched alkoxy having 3 to 6 carbon atoms), and particularly preferred is alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms).
  • alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.
  • aryloxy of “optionally substituted aryloxy” for R 21 to R 28 is a group in which the hydrogen of —OH group is substituted with aryl, and this aryl is the above-mentioned R 21 to R 28 Reference may be made to groups described as "aryl”.
  • arylthio of “ optionally substituted arylthio” for R 21 to R 28 is a group in which the hydrogen of —SH group is substituted with aryl, and this aryl is the same as the “aryl The group described as "" can be cited.
  • Examples of “trialkylsilyl” for R 21 to R 28 include groups in which three hydrogen atoms in a silyl group are each independently substituted with alkyl, and this alkyl is the same as the “alkyl” for R 21 to R 28 described above.
  • the groups mentioned can be cited.
  • Preferred alkyl for substitution is alkyl having 1 to 4 carbon atoms, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, cyclobutyl and the like.
  • trialkylsilyl includes trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyl dimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldi Propylsilyl, butyldipropylsilyl, sec-butyl
  • tricycloalkylsilyl for R 21 to R 28 include groups in which three hydrogen atoms in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl is the above- mentioned " Reference may be made to groups described as "cycloalkyl”.
  • Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[ 2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.
  • tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.
  • dialkylcycloalkylsilyl substituted by 2 alkyl and 1 cycloalkyl and alkyldicycloalkylsilyl substituted by 1 alkyl and 2 cycloalkyl are selected from the above specific alkyl and cycloalkyl and silyl substituted with a group such as
  • substituted amino of "optionally substituted amino” for R 21 to R 28 include amino in which two hydrogen atoms are substituted with aryl or heteroaryl.
  • Amino with 2 hydrogens replaced by aryl is diaryl (the two aryls may be unbonded or may be linked via a linking group) substituted amino and 2 hydrogens are replaced with heteroaryl
  • An amino is a diheteroaryl-substituted amino, and an amino in which two hydrogens are replaced with an aryl and a heteroaryl is an arylheteroaryl-substituted amino.
  • the groups explained as “aryl” and “heteroaryl” for R 21 to R 28 above can be cited.
  • substituted amino include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.
  • Halogen for R 21 to R 28 includes fluorine, chlorine, bromine and iodine.
  • R 21 -R 28 may be substituted as described above, where substituents include alkyl, cycloalkyl, aryl or heteroaryl.
  • This alkyl, cycloalkyl, aryl or heteroaryl can refer to the groups described as “alkyl”, “cycloalkyl”, “aryl” or “heteroaryl” for R 21 to R 28 above.
  • R 29 in “>N—R 29 ” as Y is hydrogen or optionally substituted aryl, and as this aryl, the groups described as “aryl” for R 21 to R 28 above can be cited. Also, as the substituent, the groups described as the substituents for R 21 to R 28 can be cited.
  • Adjacent groups among R 21 to R 28 may be bonded to each other to form a hydrocarbon ring, aryl ring or heteroaryl ring.
  • a group represented by the following formula (A-1) does not form a ring, and a group represented by the following formulas (A-2) to (A-14) is an example of a ring formed group. be done.
  • At least one hydrogen in the group represented by any one of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (two aryls may be unbonded or bonded via a linking group) substituted amino, diheteroaryl substituted amino, aryl Optionally substituted with heteroaryl-substituted amino, halogen, hydroxy or cyano.
  • Examples of the ring formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring. , and these rings are formed so as to be fused with one or two benzene rings in formula (A-1).
  • the group represented by formula (A) is a group obtained by removing one hydrogen at any position in formula (A), and * indicates the position. That is, the group represented by Formula (A) may have any position as the bonding position. For example, any carbon atom on two benzene rings in the structure of formula (A), or any one of R 21 to R 28 in the structure of formula (A) formed by combining adjacent groups with each other or any position in R 29 in “>N—R 29 ” as Y in the structure of formula (A), or N in “>N—R 29 ” (where R 29 is It can be a group that directly binds to ). The same applies to groups represented by any one of formulas (A-1) to (A-14).
  • Examples of the group represented by the formula (A) include groups represented by any one of the formulas (A-1) to (A-14), and the groups represented by the formulas (A-1) to (A-5) ) and a group represented by any one of formulas (A-12) to (A-14) is preferred, and a group represented by any one of formulas (A-1) to (A-4) is more preferred.
  • Formula (A-1), Formula (A-3) and Formula (A-4) are more preferable, and the group represented by Formula (A-1) is particularly preferable.
  • Examples of the group represented by formula (A) include the following groups. Y and * in the formula have the same definitions as above.
  • the group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), in formula (3-X3) and any one of Ar 3 in formula (3-X3).
  • all or part of hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may be deuterium.
  • the anthracene compound as a host may be, for example, a compound represented by the following formula (3-H2).
  • Ar c is optionally substituted aryl or optionally substituted heteroaryl
  • R c is hydrogen, alkyl, or cycloalkyl
  • Ar 11 , Ar 12 , Ar 13 , Ar 14 , Ar 15 , Ar 16 , Ar 17 and Ar 18 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl , optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, and at least one in the compound represented by formula (1) Hydrogen may be substituted with halogen, cyano, or deuterium.
  • the "optionally substituted aryl” is also preferably a group represented by any one of the following formulas (3-H2-X1) to (3-H2-X8).
  • Ar 21 , Ar 22 and Ar 23 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A).
  • the group represented by formula (A) is the same as that described for the anthracene compound represented by formula (3-H).
  • Ar 24 , Ar 25 , Ar 26 , Ar 27 , Ar 28 , Ar 29 and Ar 30 are each independently hydrogen, phenyl , biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A).
  • any one or two or more hydrogen atoms in each of the groups represented by formulas (3-H2-X1) to (3-H2-X8) are alkyl having 1 to 6 carbon atoms (preferably methyl or t-butyl).
  • optionally substituted aryl are selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and groups represented by formula (A). and terphenylyl (especially m-terphenyl-5'-yl) optionally substituted with one or more substituents.
  • Optionally substituted heteroaryl also includes a group represented by formula (A).
  • specific examples of “optionally substituted aryl” and “optionally substituted heteroaryl” include dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl and the like.
  • At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.
  • Halogen in this context includes fluorine, chlorine, bromine, and iodine.
  • Particularly preferred is a compound represented by the formula (3-H2) in which all hydrogen atoms are replaced with deuterium.
  • R c is hydrogen, alkyl or cycloalkyl, preferably hydrogen, methyl or t-butyl, more preferably hydrogen.
  • at least two of Ar 11 to Ar 18 are preferably optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) has at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl attached to the anthracene ring. It is preferable to have a structure that
  • anthracene compound represented by formula (3-H2) two of Ar 11 to Ar 18 are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, substituted It is more preferably optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, in the anthracene compound represented by formula (3-H2), three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring. Having a structure is more preferable.
  • any two of Ar 11 to Ar 18 are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl , or t-butyl.
  • R c is hydrogen and any six of Ar 11 to Ar 18 are hydrogen.
  • the anthracene compound represented by formula (3-H2) has the following formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3 -H2-E) is preferably an anthracene compound.
  • Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ' and Ar 18 ' are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl , chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), wherein at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluoro It may be substituted with orenyl, chrysenyl, triphenylenyl, pyrenyl, or
  • Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 ' are each substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl In some cases, it is preferably a group represented by any one of the above formulas (3-H2-X1) to (3-H2-X7).
  • Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ' and Ar 18 ' are each independently phenyl, biphenylyl (especially biphenyl-2-yl or biphenyl -4-yl), terphenylyl (especially m-terphenyl-5′-yl), naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4)
  • at least one hydrogen in these groups is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or the above formulas (A-1) to (A-4) It may be substituted with a group represented by any one.
  • At least One hydrogen may be substituted with halogen, cyano, or deuterium.
  • a deuterated form is also preferred, and a form in which all anthracene rings are deuterated or all hydrogen atoms are deuterated is preferred.
  • anthracene compound represented by the formula (3-H2) an anthracene compound represented by the following formula (3-H2-Aa) can be mentioned.
  • Ar c ', Ar 14 ', and Ar 15 ' are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl , or a group represented by any one of the above formulas (A-1) to (A-11), wherein at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzo It may be substituted with fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-11).
  • Ar c ', Ar 14 ', and Ar 15 ' are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or the above formulas (A-1) to ( A-4), wherein at least one hydrogen in these groups is preferably phenyl, naphthyl, phenanthryl, fluorenyl, or formulas (A-1) to (A-4) may be substituted with a group represented by any one of
  • the compound represented by the formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab).
  • D is deuterium
  • Ar c ', Ar 14 ', and Ar 15 ' are the same as defined in formula (3-H2-Aa).
  • D in the formula (3-H2-Ab) indicates that at least this position is deuterium, any one or more other hydrogen in the formula (3-H2-Ab) may be deuterium at the same time , and (3-H2-Ab) are both deuterium.
  • anthracene compound examples include compounds represented by formulas (3-131-Y) to (3-182-Y), formula (3-183-N), formula (3- 184-Y) to formula (3-284-Y), and formula (3-500) to formula (3-557), and formula (3-600) to formula (3-605), and formula (3-606 -Y) to compounds represented by formula (3-626-Y).
  • formulas (3-131-Y) to (3-182-Y) formula (3-183-N), formula (3- 184-Y) to formula (3-284-Y), and formula (3-500) to formula (3-557), and formula (3-600) to formula (3-605), and formula (3-606 -Y) to compounds represented by formula (3-626-Y).
  • Y in the formula is —O—, —S—, >N—R 29 (R 29 has the same definition as above) or >C(—R 30 ) 2 (R 30 is optionally linked aryl or alkyl ), R 29 is, for example, phenyl, and R 30 is, for example, methyl.
  • formula (3-131-Y) becomes formula (3-131-O)
  • formula (3- 131-S) or formula (3-131-N) formula (3-131-N).
  • D is deuterium
  • the above anthracene compounds are composed of a compound having a reactive group at a desired position of the anthracene skeleton and, in the case of the anthracene compound represented by the formula (3-H), a moiety such as X, Ar 4 and the structure of the formula (A). It can be produced by using a compound having a reactive group in its structure as a starting material and applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups of these reactive compounds include halogen and boronic acid. As a specific production method, for example, reference can be made to the synthesis method in paragraphs [0089] to [0175] of WO2014/141725.
  • R 1 to R 10 are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) via a linking group), diarylamino, di heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl; 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 are each independently bonded to form a condensed ring Alternatively, a spiro ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diaryl amino), diheteroarylamino
  • alkenyl for R 1 to R 10 examples include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and 2 to 6 carbon atoms. Alkenyl is more preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred.
  • Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.
  • any one of the compounds represented by the following formulas (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4) or (4-Ar5) Also included are monovalent groups represented by omitting one hydrogen atom.
  • Y 1 is each independently O, S or NR; R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.
  • heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton in formula (4-H) and the heteroaryl may not only be directly bonded to each other, but may also be bonded to each other via a linking group.
  • the linking group includes phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O-, or -OCH 2 CH 2 O-.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 in formula (4-H) are each independently They may combine to form a condensed ring, and R9 and R10 may combine to form a spiro ring.
  • the condensed ring formed by R 1 to R 8 is a ring condensed to the benzene ring in formula (4-H) and is an aliphatic or aromatic ring.
  • An aromatic ring is preferred, and structures including a benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring.
  • the spiro ring formed by R 9 and R 10 is a ring spiro-bonded to the 5-membered ring in formula (4-H) and is an aliphatic or aromatic ring.
  • An aromatic ring such as a fluorene ring is preferred.
  • the compound represented by formula (4-H) is preferably a compound represented by formula (4-H-1), formula (4-H-2) or formula (4-H-3) below. , a compound in which the benzene rings formed by combining R 1 and R 2 in formula (4-H) are condensed, and a benzene ring formed by combining R 3 and R 4 in formula (4-H) is a compound in which is condensed, a compound in which none of R 1 to R 8 is bonded in formula (4-H).
  • R 1 to R 10 in formula (4-H-1), formula (4-H-2) and formula (4-H-3) are the same as the corresponding R 1 to R 10 in formula (4-H).
  • R 11 to R 14 in formulas (4-H-1) and (4-H-2) is the same as that of R 1 to R 10 in formula (4-H).
  • the compound represented by formula (4-H) is more preferably a compound represented by formula (4-H-1A), formula (4-H-2A) or formula (4-H-3A) below. is a compound in which R 9 and R 10 are bonded to form a spiro-fluorene ring in formula (4-H-1), formula (4-H-1) or formula (4-H-3), respectively be.
  • R 2 to R 7 in formula (4-H-1A), formula (4-H-2A) and formula (4-H-3A) are defined in formula (4-1), formula (4-2) and formula The same as the corresponding R 2 to R 7 in (4-3), and the definitions of R 11 to R 14 in formulas (4-H-1A) and (4-H-2A) are also and the same as R 11 to R 14 in formula (4-2).
  • fluorene compound as the host of the present invention include compounds represented by the following structural formulas.
  • Me shows methyl.
  • a dibenzochrysene compound as a host is, for example, a compound represented by the following formula (5-H).
  • R 1 to R 16 are each independently hydrogen, aryl, or heteroaryl (the heteroaryl is bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. ), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy wherein at least one hydrogen is substituted with aryl, heteroaryl, alkyl or cycloalkyl
  • adjacent groups among R 1 to R 16 may combine to form a condensed ring, and at least one hydrogen in the formed ring is aryl, heteroaryl (the heteroaryl aryl may be attached to the formed ring through a linking group), substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy at least one hydrogen in these
  • Alkenyl in the definition of formula (5-H) includes, for example, alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and 2 carbon atoms. Alkenyls having ⁇ 6 are more preferred, and alkenyls having 2 to 4 carbon atoms are particularly preferred.
  • Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.
  • any one of the compounds represented by the following formulas (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) Also included are monovalent groups represented by omitting one hydrogen atom.
  • Y 1 is each independently O, S or NR; R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.
  • heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton in formula (5-H) and the heteroaryl may not only be directly bonded to each other, but may also be bonded to each other via a linking group.
  • the linking group includes phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O-, or -OCH 2 CH 2 O-.
  • R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 are hydrogen.
  • R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 in formula (5-H) are each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl , phenanthrenyl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (having the structure A monovalent group is represented by the formula ( 5- (which may be bonded to the dibenzochrysene skeleton in H)), preferably methyl, ethyl, propyl, or butyl.
  • Compounds represented by formula (5-H) are more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R16 is hydrogen.
  • at least one (preferably one or two, more preferably one) of R 3 , R 6 , R 11 and R 14 in formula (5-H) is a single bond, phenylene, biphenylene, through naphthylene, anthracenylene, methylene, ethylene, —OCH 2 CH 2 —, —CH 2 CH 2 O—, or —OCH 2 CH 2 O—, formula (5-Ar1), formula (5-Ar2), A monovalent group having a structure of formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5), other than the at least one (i.e., a monovalent group having the structure substituted position) is hydrogen, phenyl, biphenylyl, naphthyl,
  • R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 in formula (5-H) are represented by formulas (5-Ar1) to (5-Ar5). is selected, at least one hydrogen in the structure is bonded to any one of R 1 to R 16 in formula (5-H) to form a single bond may
  • dibenzochrysene compound as the host of the present invention include compounds represented by the following structural formulas. "tBu” indicates t-butyl.
  • the light-emitting layer material (host material and dopant material) described above is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a polymer crosslinked product thereof, or a main chain
  • a pendant-type polymer compound obtained by reacting a type polymer with the reactive compound or a pendant-type polymer crosslinked product thereof can also be used as a material for a light-emitting layer.
  • the reactive substituent in this case, the description of the polycyclic aromatic compound represented by formula (1) can be cited.
  • the light-emitting layer in the organic electroluminescent device may contain a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. It is also preferable to use the polycyclic aromatic compound of the present invention as an emitting dopant. A thermally activated delayed phosphor can be used as the assisting dopant (compound).
  • an organic electroluminescence device using a thermally activated delayed phosphor as an assisting dopant is sometimes referred to as a "TAF device” (TADF Assisting Fluorescence device).
  • TAF device TADF Assisting Fluorescence device.
  • the “host compound” in the TAF element means that the lowest excited singlet energy level obtained from the shoulder on the short wavelength side of the peak of the fluorescence spectrum is a thermally activated delayed phosphor as the second component, and It means a compound higher than the emitting dopant.
  • Thermal activated delayed phosphor absorbs thermal energy to cause reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and radiatively deactivates from the lowest excited singlet state to delay It means a compound capable of emitting fluorescence.
  • thermalally activated delayed fluorescence also includes those that pass through a higher triplet in the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, Durham University paper by Monkman et al. (NATURE COMMUNICATIONS, 7:13680, DOI: 10.1038/ncomms13680), National Institute of Advanced Industrial Science and Technology paper by Hosokai et al. (Hosokai et al., Sci. Adv.
  • the target compound when the fluorescence lifetime is measured at 300 K for a sample containing the target compound, the target compound is determined to be a "thermally activated delayed phosphor" based on the fact that a slow fluorescent component is observed.
  • slow fluorescence component refers to a component having a fluorescence lifetime of 0.1 ⁇ sec or more.
  • the fluorescence lifetime can be measured using, for example, a fluorescence lifetime measurement device (C11367-01, manufactured by Hamamatsu Photonics K.K.).
  • the polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermally activated delayed phosphor" can function as an assisting dopant that assists the emission of the polycyclic aromatic compound of the present invention. can be done.
  • FIG. 2 shows an energy level diagram of the light-emitting layer of a TAF element using a general fluorescent dopant as the emitting dopant (ED).
  • E (1, G) is the ground state energy level of the host
  • E (1, S, Sh) is the lowest excited singlet energy level obtained from the shoulder on the short wavelength side of the host fluorescence spectrum
  • E (1, S, Sh) is the host
  • E (1, T, Sh) is the lowest excited triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum
  • E (2, G) the lowest excited singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the assisting dopant, which is the second component
  • E (2, S, Sh) is the lowest excited triplet energy level obtained from the shoulder on the short wavelength side of the optical spectrum
  • E (3, G) is the ground state energy level of the emitting dopant, which is the third
  • the lowest excited singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the emitting dopant, which is the third component, is E (3, S, Sh)
  • the phosphorescence spectrum of the emitting dopant, which is the third component Let E (3, T, Sh) be the lowest excited triplet energy level obtained from the shoulder on the short wavelength side, h + be holes, e - be electrons, and FRET (Fluorescence Resonance Energy Transfer) be fluorescence resonance energy transfer.
  • FRET Fluorescence Resonance Energy Transfer
  • the energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, thereby achieving high luminous efficiency. This is presumed to be due to the following light emission mechanism.
  • FIG. 3 shows a preferable energy relationship in the organic electroluminescence device of this embodiment.
  • the compound having a boron atom as the emitting dopant has a high lowest excited triplet energy level E(3, T, Sh). Therefore, even if the excited singlet energy upconverted at the assisting dopant intersystem-crosses to the lowest excited triplet energy level E(3,T,Sh) at the emitting dopant, or recovered to the lowest excited triplet energy level E(2, T, Sh) on the assisting dopant (thermally activated delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. It is also expected that the separation of the upconversion and luminescence functions into two separate molecules will reduce the high energy residence time and reduce the burden on the compound.
  • known host compounds can be used, for example, compounds having at least one of a carbazole ring and a furan ring. It is preferable to use a compound in which at least one of is bound. Specific examples include mCP and mCBP.
  • the lowest excited triplet energy level E(1, T, Sh) obtained from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum of the host compound is from the viewpoint of promoting the generation of TADF in the light-emitting layer without hindering it.
  • a TADF-active compound may also be used as the host compound.
  • a compound represented by any one of the above formulas (H1), (H2) and (H3) can be used.
  • the thermally activated delayed fluorescent substance (TADF compound) used in the TAF element uses an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to perform intramolecular HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital), designed to cause efficient reverse intersystem crossing, donor-acceptor thermally activated delayed phosphor (DA type TADF compound ) is preferred.
  • DA type TADF compound donor-acceptor thermally activated delayed phosphor
  • the term "electron-donating substituent” (donor) as used herein means a substituent and a partial structure in which a HOMO orbital is localized in a thermally activated delayed phosphor molecule.
  • acceptable substituent (acceptor) means a substituent and a partial structure in which a LUMO orbital is localized in a thermally activated delayed phosphor molecule.
  • thermally activated delayed phosphors using donors and acceptors have a large spin-orbit coupling (SOC) due to their structure, and a small exchange interaction between HOMO and LUMO, ⁇ E (ST ) gives very fast inverse intersystem crossing velocities.
  • thermally activated delayed fluorophores using donors and acceptors exhibit greater structural relaxation in the excited state (for some molecules, the stable structure differs between the ground state and the excited state, so external stimuli can cause excitation from the ground state). When the conversion occurs, the structure then changes to the stable structure in the excited state), giving a broad emission spectrum, which can reduce color purity when used as a light-emitting material.
  • thermally activated delayed phosphor in the TAF element for example, a compound in which a donor and an acceptor are bound directly or via a spacer can be used.
  • electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention for example, Chemistry of Materials, 2017, 29, 1946-1963 The structures described can be used.
  • Donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, and tercarbazole.
  • diphenylcarbazolylamine diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4, N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine and diphenyl-dihydrodibenzazacillin.
  • Acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, and thiadiazole.
  • the compound having thermally activated delayed fluorescence in the TAF element has, as a partial structure, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole,
  • a compound containing at least one selected from oxadiazole, thiadiazole and benzophenone is preferred.
  • the compound used as the second component of the light-emitting layer in the TAF element is preferably a thermally activated delayed phosphor whose emission spectrum at least partially overlaps with the absorption peak of the emitting dopant.
  • Compounds that can be used as the second component (thermally activated delayed phosphor) of the light-emitting layer in the TAF device are exemplified below.
  • compounds that can be used as thermally activated delayed phosphors in the TAF element are not limited to the following exemplary compounds. In the formula below, Me represents methyl, tBu represents t-butyl, and the wavy line represents the bonding position.
  • M is each independently a single bond, -O-, >N-Ar or > CAr2 , and the HOMO depth of the partial structure to be formed And from the viewpoint of the height of the lowest excited singlet energy level and the lowest excited triplet energy level, it is preferably a single bond, —O— or >N—Ar.
  • J is a spacer structure that separates the donor partial structure and the acceptor partial structure, each independently being an arylene having 6 to 18 carbon atoms, and a conjugation exuding from the donor partial structure and the acceptor partial structure. From the viewpoint of size, arylene having 6 to 12 carbon atoms is preferred.
  • More specific examples include phenylene, methylphenylene and dimethylphenylene.
  • Each Ar is independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 18 carbon atoms, and forming a partial structure From the viewpoint of the HOMO depth and the height of the lowest excited singlet energy level and the lowest excited triplet energy level, preferably hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms or cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert -butylcarbazolyl, benzimidazole or phenylbenzimidazole, more preferably hydrogen, phenyl or carbazo
  • n is 1 or 2; n is an integer of (6-m) or less, preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen in the compounds represented by the above formulas may be substituted with halogen or deuterium.
  • the compounds used as the second component of this embodiment are 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz.
  • the compound used as the second component of this embodiment may be a donor-acceptor type TADF compound represented by DA in which one donor D and one acceptor A are bonded directly or via a linking group, Having a structure represented by the following formula (DAD1) in which a plurality of donors D are bonded to one acceptor A directly or via a linking group, the characteristics of the organic electroluminescent device are more excellent. It is preferable because it becomes a thing.
  • DAD1 includes compounds represented by the following formula (DAD2).
  • D 1 , D 2 and D 3 each independently represent a donor group.
  • the donor group the above-described donor structure can be employed.
  • a 1 and A 2 each independently represent an acceptor group.
  • the acceptor group the above acceptor structure can be employed.
  • L 1 , L 2 and L 3 each independently represent a single bond or a conjugated linking group.
  • the conjugate linking group is a spacer structure that separates the donor group and the acceptor group, and is preferably arylene having 6 to 18 carbon atoms, more preferably arylene having 6 to 12 carbon atoms.
  • L 1 , L 2 and L 3 are each independently phenylene, methylphenylene or dimethylphenylene.
  • n in the formula (DAD1) represents an integer of 2 or more and less than the maximum number with which A1 can be substituted. n may be selected, for example, within the range of 2-10, or within the range of 2-6. When n is 2, it becomes a compound represented by the formula (DAD2).
  • the n D 1 's may be the same or different, and the n L 1 's may be the same or different.
  • Preferred specific examples of the compounds represented by the formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, and the second component that can be employed in the present invention is these compounds. Not limited.
  • the luminescent layer may be either a single layer or multiple layers.
  • the host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one component each may be contained in multiple layers.
  • the host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may be of one type or a combination of two or more of them. Assisting dopants and emitting dopants may be wholly or partially contained in the host compound as the matrix.
  • a light-emitting layer doped with an assisting dopant and an emitting dopant can be formed by a method of forming a film by ternary co-evaporation of a host compound, an assisting dopant and an emitting dopant, or by mixing a host compound, an assisting dopant and an emitting dopant in advance. It can be formed by a wet film-forming method such as a method of simultaneously vapor-depositing a host compound, an assisting dopant and an emitting dopant in an organic solvent and applying a light-emitting layer forming composition (coating) prepared by dissolving the host compound, an assisting dopant and an emitting dopant in an organic solvent. can.
  • the amount of host compound used varies depending on the type of host compound, and should be determined according to the properties of the host compound.
  • a guideline for the amount of the host compound used is preferably 40 to 99.999% by mass, more preferably 50 to 99.99% by mass, and still more preferably 60 to 99.9% by mass of the total light-emitting layer material. is. The above range is preferable in terms of, for example, efficient charge transport and efficient energy transfer to the dopant.
  • the amount of assisting dopant (thermally activated delayed phosphor) used varies depending on the type of assisting dopant, and should be determined according to the characteristics of the assisting dopant.
  • a guideline for the amount of the assisting dopant used is preferably 1 to 60% by mass, more preferably 2 to 50% by mass, still more preferably 5 to 30% by mass, based on the total light-emitting layer material. The above range is preferable in that, for example, energy can be efficiently transferred to the emitting dopant.
  • the amount of emitting dopant (compound having a boron atom) to be used varies depending on the type of emitting dopant, and may be determined according to the characteristics of the emitting dopant.
  • a guideline for the amount of the emitting dopant to be used is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, and still more preferably 0.1 to 10% by mass of the total light-emitting layer material. %.
  • the above range is preferable in that, for example, the phenomenon of concentration quenching can be prevented.
  • a lower concentration of the emitting dopant is preferable in that concentration quenching phenomenon can be prevented.
  • a higher concentration of the assisting dopant is preferable from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the concentration of the emitting dopant used is lower than that of the assisting dopant.
  • a substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like.
  • the substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used.
  • glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate and polysulfone are preferred. If it is a glass substrate, soda-lime glass, alkali-free glass, or the like is used, and the thickness should be sufficient to maintain the mechanical strength.
  • the upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less.
  • the material of the glass it is preferable to use non-alkali glass because the fewer ions eluted from the glass, the better.
  • soda-lime glass with a barrier coating such as SiO 2 is also available on the market and can be used. can.
  • the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side thereof in order to enhance gas barrier properties. When used, it is preferable to provide a gas barrier film.
  • Anode in Organic Electroluminescent Device serves to inject holes into light-emitting layer 105 . Note that when either one of the hole injection layer 103 and the transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .
  • Materials for forming the anode 102 include inorganic compounds and organic compounds.
  • inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide metal (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, and the like.
  • Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be used by appropriately selecting from materials used as anodes of organic EL elements.
  • the resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but a low resistance is desirable from the viewpoint of power consumption of the light emitting element.
  • an ITO substrate of 300 ⁇ / ⁇ or less functions as an element electrode, but it is now possible to supply a substrate of about 10 ⁇ / ⁇ . It is particularly desirable to use a low resistance product of / ⁇ .
  • the thickness of ITO can be arbitrarily selected according to the resistance value, it is usually used in the range of 50 to 300 nm.
  • the hole-injecting layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light-emitting layer 105 or the hole-transporting layer 104 .
  • the hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105 .
  • the hole injection layer 103 and the hole transport layer 104 are each formed by stacking and mixing one or more kinds of hole injection/transport materials, or by a mixture of a hole injection/transport material and a polymer binder. be done. Also, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form the layer.
  • the ionization potential is low, the hole mobility is high, the stability is excellent, and impurities that become traps are less likely to occur during manufacture and use.
  • Materials for forming the hole injection layer 103 and the hole transport layer 104 include compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and hole injection layers of organic EL devices. Any compound can be selected and used from known compounds used for the hole transport layer.
  • carbazole derivatives N-phenylcarbazole, polyvinylcarbazole, etc.
  • biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole)
  • triarylamine derivatives (4,4', 4′′-tris(N-carbazolyl)triphenylamine, polymer with aromatic tertiary amino in main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N '-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N '-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1
  • Polycarbonate, styrene derivatives, polyvinylcarbazole, polysilane and the like having the above-mentioned monomers in side chains are preferable for polymer systems. is not particularly limited as long as it is a compound capable of transporting
  • organic semiconductors It is also known that the conductivity of organic semiconductors is strongly affected by their doping.
  • Such an organic semiconductor matrix material is composed of a compound with good electron-donating property or a compound with good electron-accepting property.
  • Strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known for doping electron donors.
  • TCNQ tetracyanoquinonedimethane
  • F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane
  • the conductivity of the base material varies considerably depending on the number and mobility of holes.
  • matrix materials with hole-transport properties for example, benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known ( Japanese Patent Laid-Open No. 2005-167175).
  • the polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.
  • An electron blocking layer may be provided between the hole injection/transport layer and the light emitting layer to prevent diffusion of electrons from the light emitting layer.
  • a compound represented by any of the above formulas (H1), (H2) and (H3) can be used to form the electron blocking layer.
  • the polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.
  • the electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106 .
  • the electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105 .
  • the electron transport layer 106 and the electron injection layer 107 are formed by stacking and mixing one or more electron transport/injection materials, or by a mixture of an electron transport/injection material and a polymer binder.
  • the electron injection/transport layer is a layer in which electrons are injected from the cathode and is responsible for transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For this purpose, it is preferable to use a substance that has high electron affinity, high electron mobility, excellent stability, and does not easily generate trapping impurities during production and use. However, when considering the transport balance of holes and electrons, if the function mainly plays the role of efficiently preventing holes from the anode from flowing to the cathode side without recombination, the electron transport capacity is not so high. Even if it is not high, the effect of improving the luminous efficiency is equivalent to that of a material with a high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also have the function of a layer capable of efficiently blocking the movement of holes.
  • Materials (electron transport materials) forming the electron transport layer 106 or the electron injection layer 107 include compounds conventionally used as electron transport compounds in photoconductive materials, and those used in the electron injection layer and electron transport layer of organic EL elements. It can be used by arbitrarily selecting from among the known compounds that are known.
  • Materials used for the electron transport layer or electron injection layer include compounds composed of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, It preferably contains at least one selected from pyrrole derivatives, condensed ring derivatives thereof, and metal complexes having electron-accepting nitrogen.
  • condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives.
  • quinone derivatives such as anthraquinone and diphenoquinone
  • phosphine oxide derivatives arylnitrile derivatives
  • indole derivatives examples include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes. These materials may be used alone, but may be used in combination with different materials.
  • electron transfer compounds include pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, and diphenylquinone derivatives.
  • perylene derivatives perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl -1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazines derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (
  • Metal complexes having electron-accepting nitrogen can also be used, for example, quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, benzoquinoline metal complexes, and the like. can give.
  • the above materials can be used alone, but they can be used by mixing with different materials.
  • borane derivatives pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metals Complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives are preferred.
  • the polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or a material for forming an electron transport layer.
  • the electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer.
  • a substance capable of reducing the material forming the electron transport layer or electron injection layer Various substances are used as the reducing substance as long as they have a certain reducing property. from the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one selected can be preferably used.
  • Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2.95 eV). 9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and materials with a work function of 2.9 eV or less are particularly preferred.
  • more preferred reducing substances are alkali metals of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs.
  • alkali metals have a particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, it is possible to improve the emission luminance and extend the life of the organic EL device.
  • a combination of two or more of these alkali metals is also preferable, particularly a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
  • Cs such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
  • the cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .
  • the material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used.
  • Metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloys, magnesium - indium alloys, aluminum-lithium alloys such as lithium fluoride/aluminum, etc.). Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective in increasing the electron injection efficiency and improving the device characteristics.
  • these low work function metals are generally unstable in the atmosphere.
  • a method of doping an organic layer with a small amount of lithium, cesium, or magnesium to use a highly stable electrode is known.
  • Other dopants can also be inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide. However, it is not limited to these.
  • metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride
  • a preferable example is lamination of a hydrocarbon-based polymer compound or the like.
  • the method of manufacturing these electrodes is not particularly limited, either by resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like, as long as it can provide electrical continuity.
  • Binder that may be used in each layer> The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer described above can form each layer alone.
  • Each layer constituting the organic EL element is formed by applying a material to constitute each layer by vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, inkjet method, spin coating method or casting method, coating method, and the like. It can be formed by forming a thin film by a method.
  • the thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation film thickness measuring device or the like.
  • the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, and the like.
  • the vapor deposition conditions are generally boat heating temperature +50 to +400° C., degree of vacuum 10 ⁇ 6 to 10 ⁇ 3 Pa, vapor deposition rate 0.01 to 50 nm/sec, substrate temperature ⁇ 150 to +300° C., film thickness 2 nm to 5 ⁇ m. It is preferable to set appropriately within the range.
  • an organic EL device comprising an anode/hole injection layer/hole transport layer/light-emitting layer comprising a host material and a dopant material/electron transport layer/electron injection layer/cathode.
  • the manufacturing method of is explained.
  • a thin film of an anode material is formed on a suitable substrate by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode.
  • a host material and a dopant material are co-deposited thereon to form a thin film to form a light-emitting layer, an electron-transporting layer and an electron-injecting layer are formed on the light-emitting layer, and a thin film of a cathode material is formed by vapor deposition or the like.
  • a target organic EL element is obtained by forming the material and using it as a cathode. In the production of the organic EL element described above, the order of production can be reversed to produce the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode in this order. is.
  • the organic EL device When a DC voltage is applied to the organic EL device thus obtained, it is sufficient to apply the positive polarity to the positive electrode and the negative polarity to the negative electrode. Light emission can be observed from the side (anode or cathode, and both). Further, this organic EL element emits light even when a pulse current or an alternating current is applied. Note that the AC waveform to be applied may be arbitrary.
  • Organic EL elements can also be applied to display devices, lighting devices, and the like.
  • a display device or a lighting device equipped with an organic EL element can be manufactured by a known method such as connecting the organic EL element and a known driving device, and a known driving method such as DC driving, pulse driving, or AC driving can be used. It can be driven by using it appropriately.
  • Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (for example, JP-A-10-335066, JP-A-2003-321546). Japanese Patent Laid-Open No. 2004-281086, etc.).
  • panel displays such as color flat panel displays
  • flexible displays such as flexible color organic electroluminescence (EL) displays (for example, JP-A-10-335066, JP-A-2003-321546). Japanese Patent Laid-Open No. 2004-281086, etc.).
  • EL organic electroluminescence
  • the display method of the display for example, either one of a matrix method and a segment method can be used. Note that matrix display and segment display may coexist in the same panel.
  • pixels for display are arranged two-dimensionally, such as in a lattice or mosaic pattern, and characters and images are displayed as a set of pixels.
  • the shape and size of the pixels are determined by the application. For example, in the image and character display of personal computers, monitors, and televisions, square pixels with a side of 300 ⁇ m or less are usually used, and in the case of a large display such as a display panel, a pixel with a side of mm order is used. become.
  • monochrome display pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are displayed side by side. In this case, there are typically delta type and stripe type.
  • a line-sequential driving method or an active matrix method may be used as a method for driving this matrix.
  • the line-sequential drive has the advantage of being simpler in structure, but considering the operating characteristics, the active matrix may be superior.
  • a pattern is formed to display predetermined information, and the determined area is illuminated.
  • Examples include time and temperature displays in digital clocks and thermometers, operating state displays in audio equipment and electromagnetic cookers, and panel displays in automobiles.
  • Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, etc. etc.).
  • Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light by themselves, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, and the like.
  • a backlight for liquid crystal display devices especially for personal computers, where thinning is an issue, it is difficult to reduce the thickness of conventional backlights because they consist of fluorescent lamps and light guide plates.
  • the backlight using is characterized by its thinness and light weight.
  • the polycyclic aromatic compound according to the present invention can be used for producing organic field effect transistors, organic thin-film solar cells, etc., in addition to the organic electroluminescence devices described above.
  • An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. It is a transistor that can control current by arbitrarily blocking the flow of electrons (or holes) flowing between a source electrode and a drain electrode by generating an electric field when a voltage is applied to the gate electrode.
  • a field effect transistor is easier to miniaturize than a simple transistor (bipolar transistor), and is often used as an element constituting an integrated circuit or the like.
  • the structure of an organic field effect transistor is generally such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and furthermore, a source electrode and a drain electrode are provided in contact with the organic semiconductor active layer. It suffices that the gate electrode is provided with an insulating layer (dielectric layer) interposed therebetween. Examples of the device structure include the following structure.
  • Substrate/gate electrode/insulator layer/source electrode/drain electrode/organic semiconductor active layer (2) Substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode/drain electrode (3) Substrate/organic Semiconductor active layer/source electrode/drain electrode/insulator layer/gate electrode (4) Substrate/source electrode/drain electrode/organic semiconductor active layer/insulator layer/gate electrode It can be applied as a pixel driving switching element of an active matrix driving liquid crystal display or an organic electroluminescence display.
  • An organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass.
  • the photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side.
  • the polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties.
  • the polycyclic aromatic compound according to the present invention can function as a hole-transporting material or an electron-transporting material in an organic thin-film solar cell.
  • the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like.
  • a hole blocking layer for the organic thin-film solar cell, known materials used for organic thin-film solar cells can be appropriately selected and used in combination.
  • Wavelength conversion material The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.
  • Color conversion means wavelength conversion of light emitted from a light-emitting body into light of a longer wavelength, for example, conversion of ultraviolet light or blue light into green light or red light emission.
  • a full-color display can be produced by combining such a white light source, which is a combination of a blue light source and a wavelength conversion film having a color conversion function, as a light source unit, a liquid crystal driving portion, and a color filter. Moreover, if there is no liquid crystal drive part, it can be used as a white light source as it is, and can be applied as a white light source such as LED illumination.
  • a blue organic EL device as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it is possible to produce a full-color organic EL display without using a metal mask.
  • a blue micro-LED as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it is possible to fabricate a low-cost full-color micro-LED display.
  • the polycyclic aromatic compound of the present invention can be used as this wavelength conversion material.
  • the light from a light source or light emitting element that generates ultraviolet light or shorter wavelength blue light can be converted to a display device (a display device using an organic EL device or a liquid crystal). It can be converted into blue light or green light with high color purity suitable for use in display devices.
  • the color to be converted can be adjusted by appropriately selecting the substituents of the polycyclic aromatic compound of the present invention, the binder resin used in the composition for wavelength conversion described below, and the like.
  • a wavelength converting material can be prepared as a wavelength converting composition containing the polycyclic aromatic compound of the present invention. Moreover, you may form a wavelength conversion film using this composition for wavelength conversion.
  • the wavelength conversion composition may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention.
  • a binder resin for example, those described in paragraphs 0173 to 0176 of WO2016/190283 can be used.
  • other additives compounds described in paragraphs 0177 to 0181 of International Effects 2016/190283 can be used.
  • the solvent the description of the solvent contained in the composition for forming the light-emitting layer can be referred to.
  • a wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition.
  • a method for producing a wavelength conversion layer from a wavelength conversion composition known film forming methods can be referred to.
  • the wavelength conversion film may consist of only the wavelength conversion layer formed from the composition containing the polycyclic aromatic compound of the present invention, and other wavelength conversion layers (for example, the A wavelength conversion layer, a wavelength conversion layer that converts blue light or green light into red light) may be included.
  • the wavelength conversion film may contain a substrate layer and a barrier layer for preventing deterioration of the color conversion layer due to oxygen, moisture, or heat.
  • intermediate (X-1) (47.0 g), 1-t-butyl-3,4,5-trichlorobenzene (23.8 g), dichlorobis[di-t-butyl (4- Dimethylaminophenyl)phosphino]palladium (II) (Pd-132) (0.909 g), sodium-t-butoxide (NaOtBu, 14.4 g) and toluene (500 ml) were placed in a flask and heated at 120°C for 5 hours. . After completion of the reaction, water and ethyl acetate were added to the reaction mixture and the mixture was stirred, and then the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified with a silica gel short pass column (eluent: heptane) to obtain 48.2 g of intermediate (X-2).
  • reaction solution was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath and then ethyl acetate were added to separate the layers. After concentrating the organic layer, it was purified with a silica gel short pass column (eluent: chlorobenzene). The resulting crude product was recrystallized from toluene to obtain 6.90 g of compound (1-1).
  • Synthesis Example (5) Synthesis of Compound (1-155)
  • Compound (1-155) was obtained in the same manner as in Synthesis Example 1 except that Compound (X-4) was changed to Compound (X-4-155). rice field.
  • the target compound (1-252) with m/z (M+H) 1111.71 was confirmed by MS.
  • Synthesis Example (30): Synthesis of Compound (1-282) Compound (1-282) was obtained in the same manner as in Synthesis Example 1 except that Compound (X-4) was changed to Compound (X-4-282). rice field. The target compound (1-282) with m/z (M+H) 1059.73 was confirmed by MS.
  • Synthesis Example (60): Synthesis of Compound (1-412) Compound (1-412) was obtained in the same manner as in Synthesis Example 1 except that Compound (X-4) was changed to Compound (X-4-412). rice field. MS confirmed the target compound (1-412) with m/z (M+H) 1097.69.
  • Synthesis Example (70): Synthesis of Compound (1-455) Compound (1-455) was obtained in the same manner as in Synthesis Example 1 except that Compound (X-4) was changed to Compound (X-4-455). rice field. The target compound (1-455) with m/z (M+H) 1226.81 was confirmed by MS.
  • Synthesis Example (79): Synthesis of Compound (1-522) Compound (1-522) was obtained in the same manner as in Synthesis Example 1 except that Compound (X-4) was changed to Compound (X-4-522). rice field. MS confirmed the target compound (1-522) with m/z (M+H) 1133.66.
  • Synthesis Example (80): Synthesis of Compound (1-527) Compound (1-527) was obtained in the same manner as in Synthesis Example 1 except that Compound (X-4) was changed to Compound (X-4-527). rice field. The target compound (1-527) with m/z (M+H) 1186.59 was confirmed by MS.
  • the compound to be evaluated may be dissolved in a solvent and evaluated in the solvent, or may be evaluated in a thin film state. Furthermore, when evaluating in a thin film state, depending on the mode of use of the compound to be evaluated in the organic EL device, it is possible to evaluate only the compound to be evaluated as a thin film or to disperse the compound to be evaluated in an appropriate matrix material. In some cases, the film is thinned and evaluated.
  • a thin film obtained by vapor-depositing only the compound to be evaluated is referred to as a "single film”
  • a thin film obtained by coating and drying a coating solution containing the compound to be evaluated and a matrix material is referred to as a "coating film”.
  • PMMA polymethyl methacrylate
  • a compound to be evaluated are dissolved in toluene, and then a thin film is formed on a quartz transparent support substrate (10 mm ⁇ 10 mm) by spin coating to prepare a sample.
  • a thin film sample in which the matrix material is a host compound is prepared as follows.
  • a transparent support substrate made of quartz (10 mm ⁇ 10 mm ⁇ 1.0 mm) was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum vapor deposition boat containing a host compound and a dopant material were added. After installing a molybdenum deposition boat, the vacuum chamber is evacuated to 5 ⁇ 10 ⁇ 4 Pa.
  • the vapor deposition boat containing the host compound and the vapor deposition boat containing the dopant material are heated at the same time, and the host compound and the dopant material are co-deposited so as to form an appropriate film thickness.
  • a mixed thin film (sample) was formed.
  • the deposition rate is controlled according to the set mass ratio of the host compound and the dopant material.
  • the absorption spectrum of the sample is measured using an ultraviolet-visible-near-infrared spectrophotometer (Shimadzu Corporation, UV-2600).
  • the fluorescence spectrum or phosphorescence spectrum of the sample is measured using a spectrofluorophotometer (F-7000, manufactured by Hitachi High-Tech Co., Ltd.).
  • the photoluminescence is measured by exciting with an appropriate excitation wavelength at room temperature.
  • the sample is immersed in liquid nitrogen (temperature 77K) using an attached cooling unit.
  • an optical chopper was used to adjust the delay time from irradiation of excitation light to the start of measurement.
  • the sample is excited with an appropriate excitation wavelength and photoluminescence is measured.
  • the fluorescence quantum yield (PLQY) is measured using an absolute PL quantum yield measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C9920-02G).
  • the fluorescence lifetime was measured at 300K using a fluorescence lifetime measurement device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, at the maximum emission wavelength measured at an appropriate excitation wavelength, an emission component with a fast fluorescence lifetime and an emission component with a slow fluorescence lifetime were observed. In the fluorescence lifetime measurement at room temperature of general organic EL materials that emit fluorescence, it is almost impossible to observe a slow emission component associated with a triplet component derived from phosphorescence due to deactivation of the triplet component by heat. do not have. When a slow emission component is observed in the compound to be evaluated, it indicates that triplet energy with a long excitation life is transferred to singlet energy by thermal activation and observed as delayed fluorescence.
  • Ip ionization potential
  • the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries Co., Ltd. PYS-201).
  • the electron affinity can be estimated from the difference between the ionization potential measured by the method described above and the energy gap calculated by the method described above.
  • the compounds of the present invention are characterized by an appropriate energy gap (Eg), a high lowest excited triplet energy (E T ) and a small ⁇ EST. In particular, it can be expected to be applied to a light-emitting layer.
  • Eg energy gap
  • E T high lowest excited triplet energy
  • ⁇ EST small ⁇ EST
  • Example 1 A 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing an ITO film having a thickness of 180 nm by sputtering to a thickness of 150 nm is used as a transparent support substrate.
  • This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Shinku Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), and ET-1 were obtained.
  • a molybdenum deposition boat containing ET-2 and ET-2, and an aluminum nitride deposition boat containing Liq, LiF and aluminum were mounted.
  • the following layers are sequentially formed on the ITO film of the transparent support substrate.
  • the vacuum chamber was evacuated to 5 ⁇ 10 ⁇ 4 Pa, first, HI was heated to deposit a film thickness of 40 nm, then HAT-CN was heated to deposit a film thickness of 5 nm, Next, HT-1 is heated and vapor-deposited to a thickness of 45 nm, and then HT-2 is heated and vapor-deposited to a thickness of 10 nm to form a hole layer consisting of four layers. did.
  • BH and the compound (1-1) were simultaneously heated and evaporated to a thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of BH to compound (1-1) was approximately 97:3.
  • ET-1 is heated to vapor-deposit to a thickness of 5 nm, and then ET-2 and Liq are heated simultaneously to vapor-deposit to a thickness of 25 nm, forming an electronic layer consisting of two layers. formed.
  • the deposition rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 50:50.
  • the deposition rate of each layer was 0.01-1 nm/sec.
  • LiF is heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness becomes 1 nm, and then aluminum is heated and vapor-deposited so that the film thickness becomes 100 nm to form a cathode. Then, an organic EL device was obtained.
  • Examples 2 to 99, Comparative Examples 1 to 5 Organic EL devices of Examples 2 to 99 and Comparative Examples 1 to 5 were obtained in the same manner as in Example 1, except that the compounds listed in Table 2 were used instead of compound (1-1).
  • Evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and half width (nm) of emission spectrum, and the like. .
  • V driving voltage
  • emission wavelength nm
  • CIE chromaticity x, y
  • external quantum efficiency %
  • maximum wavelength nm
  • half width nm
  • the quantum efficiency of a light-emitting device includes internal quantum efficiency and external quantum efficiency.
  • the internal quantum efficiency is purely converted from external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting device into photons. indicates the percentage of
  • the external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting device, and some of the photons generated in the light-emitting layer continue to be absorbed or reflected inside the light-emitting device. Therefore, the external quantum efficiency is lower than the internal quantum efficiency because the light is not emitted to the outside of the light emitting device.
  • the methods for measuring spectral radiance (luminescence spectrum) and external quantum efficiency are as follows.
  • a voltage/current generator R6144 manufactured by Advantest Corporation is used to apply a voltage at which the luminance of the device becomes 1000 cd/m 2 to cause the device to emit light.
  • Spectral radiance in the visible light region is measured from a direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light-emitting surface is a perfect diffusion surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance of each wavelength component by the wavelength energy and multiplying by ⁇ .
  • the number of photons in the entire observed wavelength region is integrated to obtain the total number of photons emitted from the device.
  • the external quantum efficiency is obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device, with the value obtained by dividing the applied current value by the elementary charge as the number of carriers injected into the device.
  • the half width of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity becomes 50% with respect to the maximum emission wavelength.
  • a DC voltage was applied to the organic EL devices of Examples 1 to 7 using the ITO electrode as the anode and the LiF/aluminum electrode as the cathode, and the characteristics at the time of light emission of 1000 cd/m 2 were measured. Table 2 shows the results.
  • the polycyclic aromatic compound of the present invention is useful as an organic device material, particularly as a light-emitting layer material for forming the light-emitting layer of an organic electroluminescent element.
  • an organic electroluminescent device with low voltage and high efficiency light emission can be obtained.
  • REFERENCE SIGNS LIST 100 organic electroluminescent element 101 substrate 102 anode 103 hole injection layer 104 hole transport layer 105 light emitting layer 106 electron transport layer 107 electron injection layer 108 cathode

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Abstract

La présente invention concerne un composé aromatique polycyclique qui a une structure composée d'un ou de plusieurs motifs structuraux représentés par la formule (1) qui est utile en tant que matériau de dispositif organique pour des éléments EL organiques et similaires. Dans la formule, Z représente N ou C-R11 (R11 représentant un atome d'hydrogène ou un substituant) ; le cycle C représente un cycle qui est représenté par la formule (C) ; ZC représente N ou C-RC (RC représentant un atome d'hydrogène ou un substituant) ; Xc représente >S ; Y1 représente B ; un des X1 et X2 représente >N-LCY-RCY, et l'autre représente >N-GA ou >N-GB ; LCY représente un groupe arylène substitué ou non substitué ; RCY représente un groupe cycloalkyle substitué ou non substitué ; GA et GB représentent respectivement un groupe représenté par la formule (GA) et un groupe représenté par la formule (GB) ; Zg représente N ou C-Rg (Rg représentant un atome d'hydrogène ou un substituant) ; A représente >O ; les cycles aryle ou les cycles hétéroaryle dans la structure peuvent être fusionnés par un cycloalcane ; et au moins un atome d'hydrogène dans la structure peut être substitué par un groupe cyano, un atome d'halogène ou un atome de deutérium.
PCT/JP2022/011215 2021-03-15 2022-03-14 Composé aromatique polycyclique WO2022196612A1 (fr)

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KR20240113603A (ko) 2018-04-12 2024-07-22 가꼬우 호징 관세이 가쿠잉 시클로알킬 치환 다환 방향족 화합물
WO2020111830A1 (fr) 2018-11-30 2020-06-04 에스에프씨 주식회사 Élément électroluminescent organique utilisant un composé dérivé aromatique polycyclique

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CN113135945A (zh) * 2020-01-19 2021-07-20 冠能光电材料(深圳)有限责任公司 一种有机硼半导体材料及oled器件应用

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