WO2020251049A1 - Composé aromatique polycyclique - Google Patents

Composé aromatique polycyclique Download PDF

Info

Publication number
WO2020251049A1
WO2020251049A1 PCT/JP2020/023312 JP2020023312W WO2020251049A1 WO 2020251049 A1 WO2020251049 A1 WO 2020251049A1 JP 2020023312 W JP2020023312 W JP 2020023312W WO 2020251049 A1 WO2020251049 A1 WO 2020251049A1
Authority
WO
WIPO (PCT)
Prior art keywords
ring
substituted
carbon atoms
aryl
alkyl
Prior art date
Application number
PCT/JP2020/023312
Other languages
English (en)
Japanese (ja)
Inventor
琢次 畠山
馬場　大輔
亮介 川角
笹田　康幸
詠希 町田
田中　裕之
一雄 奥村
靖宏 近藤
Original Assignee
学校法人関西学院
Jnc株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 学校法人関西学院, Jnc株式会社 filed Critical 学校法人関西学院
Priority to KR1020227000819A priority Critical patent/KR20220024468A/ko
Priority to JP2021526175A priority patent/JPWO2020251049A1/ja
Priority to CN202080043697.4A priority patent/CN114026147A/zh
Publication of WO2020251049A1 publication Critical patent/WO2020251049A1/fr

Links

Images

Classifications

    • 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 System
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • 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 System
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/55—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/22—Luminous paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/122—Copolymers statistical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1414—Unsaturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/312—Non-condensed aromatic systems, e.g. benzene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
    • C08G2261/3162—Arylamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1491—Heterocyclic containing other combinations of heteroatoms

Definitions

  • the present invention relates to polycyclic aromatic compounds.
  • the present invention also relates to an organic electroluminescent device, an organic field effect transistor and an organic thin-film solar cell using the polycyclic aromatic compound, and a display device and a lighting device.
  • organic electroluminescent devices made of organic materials (“organic EL devices” in the present specification. "Or simply referred to as” element ".) has been actively studied because it is easy to reduce the weight and size.
  • organic materials having light emitting characteristics such as blue, which is one of the three primary colors of light
  • organic materials having charge transporting ability such as holes and electrons (which have the potential to become semiconductors and superconductors).
  • both high molecular weight compounds and low molecular weight compounds have been actively studied so far.
  • the organic EL element has a structure composed of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers containing an organic compound, which are arranged between the pair of electrodes.
  • Layers containing organic compounds include light emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons, and various organic materials suitable for these layers have been developed.
  • Patent Document 1 As a material for a light emitting layer, for example, a benzofluorene compound or the like has been developed (Patent Document 1). Further, as a hole transport material, for example, a triphenylamine compound or the like has been developed (Patent Document 2). Further, as an electron transport material, for example, an anthracene-based compound and the like have been developed (Patent Document 3).
  • triphenylamine derivative a material used for an organic EL element or an organic thin-film solar cell
  • This material is based on N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD), which has already been put into practical use. It is a material characterized in that its flatness is improved by connecting aromatic rings constituting triphenylamine.
  • a NO-linking compound (Compound 1 on page 63) is evaluated, but a method for producing a material other than the NO-linking compound is not described, and the element to be linked is not described. Since the electronic state of the entire compound is different if they are different, the properties obtained from materials other than the NO-linking compound are not yet known. Other examples of such compounds can be found (Patent Document 5).
  • a compound having a conjugated structure having a large triplet exciton energy (T1) is useful as a material for a blue light emitting layer because it can emit phosphorescence having a shorter wavelength.
  • an electron transport material or a hole transport material that sandwiches the light emitting layer a compound having a novel conjugated structure having a large T1 is required.
  • the host material of the organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene and carbazole are linked by a single bond or a phosphorus atom or a silicon atom. This is because the large HOMO-LUMO gap (bandgap Eg in the thin film) required for the host material is secured by connecting a large number of relatively small aromatic rings of the conjugated system.
  • the host material of the organic EL element using a phosphorescent material or a heat activated delayed fluorescent material high triplet excitation energy (E T) is also required, the donor or acceptor properties of the aromatic ring and substituents in the molecule by connecting, to localize the SOMO1 and SOMO2 triplet excited state (T1), by reducing the exchange interaction between the two trajectories, it is possible to improve the triplet excitation energy (E T) It becomes.
  • the small aromatic ring of the conjugated system does not have sufficient redox stability, and the device using the molecule connecting the existing aromatic ring as the host material does not have a sufficient life.
  • polycyclic aromatic compounds having an extended ⁇ conjugated system generally, but the redox stability is excellent, because HOMO-LUMO gap and triplet excitation energy (band gap Eg of the thin film) (E T) is low, It has been considered unsuitable for host materials.
  • Patent Document 6 reports a polycyclic aromatic compound containing boron and an organic EL device using the same, but in order to further improve the device characteristics, light emission efficiency and device life can be improved. There is a demand for layer materials, especially dopant materials.
  • the present inventors have used a polycyclic aromatic compound having a structure in which a fused ring is further introduced as a material for a light emitting layer in the polycyclic aromatic compound described in Patent Document 6. It has been found that the light emission efficiency and the device life can be improved by configuring the organic EL element.
  • the present invention is a completion of the present invention based on this finding. Specifically, the present invention has the following configuration.
  • Rings A, B, and C are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted, provided that rings A, B, and C are substituted.
  • At least one ring selected from the group consisting of is a fused 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. At least one hydrogen in this fused ring may be substituted.
  • Rings B and C may be attached via a single bond or a linking group.
  • X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R.
  • R is hydrogen, optionally substituted aryl (except amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.
  • the R of> Si (-R) 2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted.
  • the R of> C (-R) 2 may be an independently hydrogen, an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, and the like.
  • a cycloalkyl which may be substituted, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above> N R in at least one of -R,> Si (-R) 2 , and> C (-R) 2 is bonded to at least one ring of the A ring, B ring, and C ring by a linking group or a single bond.
  • May be At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane.
  • Hydrogen may be substituted and at least one -CH 2- in the cycloalkane may be substituted with -O-. At least one hydrogen in the compound or structure represented by the formula (1) may be substituted with deuterium, cyano, or halogen. )
  • At least one ring selected from the group consisting of A ring, B ring and C ring is a fused ring which is a heteroaryl ring containing a sulfur atom or an oxygen atom, and at least one hydrogen in this fused ring is May be replaced,
  • ⁇ 3> The polycyclic aromatic compound according to ⁇ 1> or ⁇ 2>, wherein at least one ring selected from the group consisting of A ring, B ring and C ring is a ring represented by the formula (BHet) or That multimer.
  • R a1 to R a6 are hydrogens or substituents, except that any two or three of R a1 to R a6 adjacent to each other are Y 1 and Y 1 in the formula (1). It becomes a bond with X 1 and / or X 2, and X is>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above>
  • the Rs of NR,> Si (-R) 2 , or> C (-R) 2 are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted, respectively.
  • alkyl which may be an alkyl or a cycloalkyl which may be substituted, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring. Good.
  • At least one ring selected from the group consisting of the B ring and the C ring is a ring represented by the formula (BHet).
  • a ring represented by the formula (BHet) any two adjacent R a1 to R a6 serve as a bond with Y 1 and X 1 or X 2 in the formula (1).
  • Others Ra1 to Ra6 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl hetero.
  • Arylamino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted.
  • the substituents in which the hydrogen of the aryl ring or the heteroaryl ring may be substituted are substituted or unsubstituted aryl, substituted or unsubstituted hetero.
  • Rings A, B, and C all include a 5- or 6-membered ring that shares a bond with the central condensed 2-ring structure of formula (1) composed of Y 1 , X 1 , and X 2 .
  • Rings B and C may be bonded via a single bond,>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S or> Se, as described above.
  • > N-R and> Si (-R) 2 R may be independently substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, alkyl or cycloalkyl, respectively.
  • Alkyl or cycloalkyl wherein the> C (-R) 2 R may be substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, alkyl or cycloalkyl. It is cycloalkyl, and the R in at least one of>N-R,> Si (-R) 2 and> C (-R) 2 is -O-, -S-, -C (-R). It may be bonded to at least one ring of the B ring and the C ring by a 2- or a single bond, and the R of the -C (-R) 2- is hydrogen, alkyl, or cycloalkyl, and the said.
  • the two Rs> Si (-R) 2 and> C (-R) 2 may be combined with each other to form a ring.
  • X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R.
  • Si (-R) 2 R may be independently substituted with an aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl, alkyl, or cyclo, respectively.
  • the R of> C (-R) 2 is alkyl, optionally substituted with hydrogen, alkyl or cycloalkyl, and optionally substituted with aryl, alkyl or cycloalkyl, heteroaryl, alkyl, or cycloalkyl.
  • the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above-mentioned> N-R and> Si (-R) may be formed.
  • ) 2 and> R in at least one of C (-R) 2 are -O-, -S-, -C (-R) 2- , or by a single bond, the A ring, B ring, and C.
  • the -C (-R) 2- R is hydrogen, alkyl, or cycloalkyl.
  • a multimer it is a dimer or trimer having two or three structures represented by the formula (1).
  • X 1 and X 2 are both a> N-R, at least one R of> N-R in which X 1 and X 2 may be the have also be 2-biphenylyl or substituted with substituted
  • ⁇ 7> At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) is condensed with at least one cycloalkane, and at least one in the cycloalkane.
  • polycyclic aromatic according to any one of ⁇ 3> to ⁇ 6>, wherein one hydrogen may be substituted, and at least one -CH 2- in the cycloalkane may be substituted with -O-.
  • ⁇ 8> In ⁇ 1> or ⁇ 2> represented by the following formulas (2), (3), (4), (5), (6), (7), (8), or (9).
  • R 1 to R 17 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 44 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino, respectively.
  • Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen is aryl, heteroaryl may be substituted by alkyl or cycloalkyl, or together with a ring adjacent groups are bonded to one of R 1 ⁇ R 3, is adjacent groups of R 8 ⁇ R 11 Adjacent groups of R 4 to R 7 are bonded to each other together with the b ring to bond with the c ring, and adjacent groups of R 12 to R 14 are bonded to each other with the a12 ring to form R 15 to.
  • Adjacent groups of R 17 are bonded to each other with the b15 ring, and adjacent groups of R 21 to R 24 are bonded to each other with the c21 ring, and adjacent groups of R 31 to R 34 are bonded to each other. They may be combined to form an aryl ring or a heteroaryl ring, respectively, with the b31 ring and with the adjacent groups of R 41 to R 44 bonded together with the b41 ring, at least in the formed ring.
  • One hydrogen can be aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl. , Alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen in these is aryl, heteroaryl, alkyl, or.
  • R b1 and R b2 are hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group).
  • Can be alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, where * is.
  • Represents the bond position X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2, or> C (-R) 2 of R each independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, wherein> Si (-R) 2, and> C (-R )
  • the two Rs of 2 may be combined with each other to form a ring.
  • R 7 and R 8 in formula (2), R 8 and R 24 in formula (3), or R 34 and R 24 in formula (5) are combined to form a single bond,>O,>NR,>.
  • Si (-R) 2 ,> C (-R) 2 ,> S, or> Se may be set, and the R of> N-R and> Si (-R) 2 may be independent of each other.
  • the two Rs of> C (-R) 2 may be combined with each other to form a ring, and at least one of the above-mentioned>N-R,> Si (-R) 2 and> C (-R) 2 .
  • R in one is bonded to at least one of the b ring, b31 ring, c ring, and c21 ring by an -O-, -S-, -C (-R) 2- , or a single bond.
  • X 1 , X 2 , X 3 , and X 4 are independent of>O,>NR,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, respectively.
  • the R of> N-R and> Si (-R) 2 are independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and 2 to 2 carbon atoms which may be substituted. 15 heteroaryl, optionally substituted alkyl having 1 to 6 carbon atoms, or optionally substituted cycloalkyl having 3 to 14 carbon atoms, wherein R of> C (-R) 2 is hydrogen. , An aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl which may have 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or an alkyl having 1 to 6 carbon atoms which may be substituted.
  • At least one of them may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms and 2 to 30 carbon atoms. Heteroaryl, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms may be substituted, and at least one -CH 2- in the cycloalkane may be substituted with -O-. Often, At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano,. Alternatively, it may be replaced with halogen. )
  • R 1 to R 17 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 44 are independently hydrogen, aryl with 6 to 30 carbon atoms, and 2 to 30 carbon atoms, respectively.
  • the groups are bonded to each other together with the a ring, the adjacent groups of R 8 to R 11 are bonded to each other to form the b ring, and the adjacent groups of R 4 to R 7 are bonded to each other together with the c ring.
  • R 12 to R 14 adjacent groups are bonded to the a12 ring, and R 15 to R 17 adjacent groups are bonded to the b15 ring, and R 21 to R 24 are adjacent to each other.
  • the groups are bonded together with the c21 ring, the adjacent groups of R 31 to R 34 are bonded together with the b31 ring, and the adjacent groups of R 41 to R 44 are bonded together with the b41 ring.
  • Each may form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring is an aryl ring having 6 to 10 carbon atoms and having 6 to 10 carbon atoms, respectively. It may be substituted with an alkyl of 1 to 12, a cycloalkyl of 3 to 16 carbon atoms or a trialkylsilyl (where alkyl is an alkyl having 1 to 4 carbon atoms).
  • R b1 and R b2 are hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diallylamino (where aryl is an aryl having 6 to 12 carbon atoms), and a diallylboryl (whereever Aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or It is a trialkylsilyl (although alkyl is an alkyl having 1 to 6 carbon atoms).
  • X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2
  • R is an aryl with 6 to 30 carbon atoms, a heteroaryl with 2 to 30 carbon atoms, an alkyl with 1 to 24 carbon atoms, or a cycloalkyl with 3 to 24 carbon atoms.
  • R 7 and R 8 or R 15 and R 16 may be combined to form>O,>N-R,> C (-R) 2 , or> S, as described above> N-R.
  • X 1 , X 2 , X 3 and X 4 are independently>O,>N-R,> C (-R) 2 , or> S, and R in> N-R is replaced.
  • Aryl having 6 to 10 carbon atoms which may be substituted, alkyl having 1 to 4 carbon atoms which may be substituted, or cycloalkyl having 5 to 10 carbon atoms which may be substituted, and the above-mentioned> C (-. R) 2 R is a hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
  • At least one of the compounds may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms and 2 to 22 carbon atoms. Heteroaryl, alkyl having 1-12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms may be substituted.
  • At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano,.
  • the polycyclic aromatic compound according to ⁇ 8> which may be substituted with halogen, or a multimer thereof.
  • ⁇ 12> Consists of an aryl ring and a heteroaryl ring in the compound represented by the formula (2), (3), (4), (5), (6), (7), (8), or (9). At least one selected from the group is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2- in the cycloalkane is-.
  • the polycyclic aromatic compound according to any one of ⁇ 8> to ⁇ 11>, which may be substituted with O ⁇ , or a multimer thereof.
  • R a11 to R a18 are hydrogens or substituents, except that any two or three of R a11 to R a18 adjacent to each other are Y 1 and Y 1 in the formula (1). It becomes a bond with X 1 and / or X 2, and X is>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above> R of NR,> Si (-R) 2 , or> C (-R) 2 is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, Alternatively, it is a cycloalkyl which may be substituted, and the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring.
  • At least one ring selected from ring B and the group consisting of C ring is a ring represented by the formula (DBHet), one of R a11 ⁇ R a18, two or adjacent the formula ( 1) Becomes a bond with Y 1 and X 1 or X 2 in In formula (DBHet), other R a11 ⁇ R a18 is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted di-heteroarylamino, Substituent or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted.
  • DBHet formula (DBHet)
  • Cycloalkyl substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl.
  • the substituents of the aryl ring or the heteroaryl ring in the ring A and the rings B and C which are not the fused rings may be substituted or unsubstituted aryl, substituted or unsubstituted hetero.
  • Rings A, B, and C all include a 5- or 6-membered ring that shares a bond with the central condensed 2-ring structure of formula (1) composed of Y 1 , X 1 , and X 2 .
  • Rings B and C may be bonded via a single bond,>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se.
  • The> N-R and> Si (-R) 2 R may be independently substituted with aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, respectively. , Alkyl, or cycloalkyl, wherein R of> C (-R) 2 is aryl, which may be substituted with hydrogen, alkyl or cycloalkyl, or heteroaryl, which may be substituted with alkyl or cycloalkyl.
  • the R in at least one of> Si (-R) 2 and> C (-R) 2 is -O-, -S-, -C (-R) 2- , or the B ring and C by a single bond. It may be attached to at least one ring of the ring, wherein the -C (-R) 2- R is hydrogen, alkyl, or cycloalkyl.
  • X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R.
  • Si (-R) 2 R may be independently substituted with an aryl, alkyl or cycloalkyl optionally substituted with hydrogen, alkyl or cycloalkyl, heteroaryl, alkyl, or cyclo, respectively.
  • the R of> C (-R) 2 is alkyl, optionally substituted with hydrogen, alkyl or cycloalkyl, and optionally substituted with aryl, alkyl or cycloalkyl, heteroaryl, alkyl, or cycloalkyl.
  • the two Rs of> Si (-R) 2 and> C (-R) 2 may be bonded to each other to form a ring, and the above-mentioned> N-R and> Si (-R) may be formed.
  • ) 2 and> R in at least one of C (-R) 2 are -O-, -S-, -C (-R) 2- , or by a single bond, the A ring, B ring, and C. It may be attached to at least one ring of the ring, wherein the -C (-R) 2- R is hydrogen, alkyl, or cycloalkyl.
  • a multimer it is a dimer or trimer having two or three structures represented by the formula (1).
  • X 1 and X 2 both are> N-R, X at least one R 1 and at the X 2> N-R may be a not also be 2-biphenylyl or substituted with substituted
  • ⁇ 17> At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by the formula (1) is condensed with at least one cycloalkane, and at least one in the cycloalkane.
  • polycyclic aromatic according to any one of ⁇ 13> to ⁇ 16>, wherein one hydrogen may be substituted, and at least one -CH 2- in the cycloalkane may be substituted with -O-.
  • ⁇ 18> In ⁇ 1> or ⁇ 2> represented by the following formulas (12), (13), (14), (15), (16), (17), (18), or (19). The polycyclic aromatic compound described or a multimer thereof.
  • R 1 ⁇ R 3 and R 8 ⁇ R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru (two aryl is a single bond or a linking group (May be bonded via), alkyl, alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is aryl, heteroaryl, May be substituted with alkyl or cycloalkyl, R 51 to R 58 and R 61 to R 68 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linking groups).
  • Adjacent groups of R 1 to R 3 are bonded to each other to form a ring, and adjacent groups of R 8 to R 11 are bonded to each other to form a ring b, which are adjacent to each other of R 51 to R 54.
  • the groups are bonded together with the c51 ring, the adjacent groups of R 55 to R 58 are bonded together with the c55 ring, and the adjacent groups of R 61 to R 64 are bonded together with the b61 ring.
  • R 65 to R 68 may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b65 ring, respectively, and at least one hydrogen in the formed ring is an aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diallylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or It may be substituted with a substituted silyl, X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2 or> C (-R) 2 R are independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, respectively, and> Si (-R) 2 and>
  • the two Rs of 2 may be combined with each other to form a ring.
  • X 1 and X 2 are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R.
  • R of Si (-R) 2 are independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl having 2 to 15 carbon atoms which may be substituted, respectively. It is an alkyl having 1 to 6 carbon atoms which may be present, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and R of> C ( ⁇ R) 2 may be hydrogen or substituted.
  • At least one selected from the group may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl or carbon having 6 to 30 carbon atoms. It may be substituted with a heteroaryl of number 2 to 30, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH 2- in the cycloalkane is substituted with -O-. May have been At least one hydrogen in the compounds represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20) is deuterium. It may be substituted with hydrogen, cyano, or halogen.
  • R 1 ⁇ R 3 and R 8 - R 11 are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl of 2-30 carbon atoms, diarylamino (where aryl is C 6-30 12 aryls), diarylboryls (where aryls are aryls with 6-12 carbon atoms, and the two aryls may be attached via a single bond or linking group), or alkyls with 1-24 carbon atoms.
  • R 51 to R 58 and R 61 to R 68 are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, and diarylamino (where aryl is aryl with 6 to 12 carbon atoms).
  • Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and 3 to 24 carbon atoms. Twenty-four cycloalkyls, or trialkylsilyls (where alkyls are alkyls with 1-6 carbon atoms). Adjacent groups of R 1 to R 3 are bonded to each other to form a ring, and adjacent groups of R 8 to R 11 are bonded to each other to form a ring b, which are adjacent to each other of R 51 to R 54.
  • the groups are bonded together with the c51 ring, the adjacent groups of R 55 to R 58 are bonded together with the c55 ring, and the adjacent groups of R 61 to R 64 are bonded together with the b61 ring. and adjacent groups together with binding to b65 ring of R 65 ⁇ R 68, respectively, may form a heteroaryl ring of aryl or C 6-15 carbon atoms 9-16, formed At least one hydrogen in the ring is aryl with 6 to 10 carbon atoms, alkyl with 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl with 3 to 16 carbon atoms (where alkyl is alkyl with 1 to 4 carbon atoms).
  • X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above-mentioned>N-R,> Si ( -R) 2 or> C (-R) 2 R is an aryl with 6 to 30 carbon atoms, a heteroaryl with 2 to 30 carbon atoms, an alkyl with 1 to 24 carbon atoms, or a cycloalkyl with 3 to 24 carbon atoms.
  • ⁇ 10 cycloalkyl, X 1 and X 2 are independently>O,>N-R,> C (-R) 2 , or> S, where R in> N-R may be substituted carbon.
  • Aryl of number 6 to 10, alkyl having 1 to 4 carbon atoms which may be substituted, or cycloalkyl having 5 to 10 carbon atoms which may be substituted, and R of> C (-R) 2 is , Hydrogen, aryl with 6 to 10 carbon atoms, alkyl with 1 to 4 carbon atoms, or cycloalkyl with 5 to 10 carbon atoms. From aryl and heteroaryl rings in compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20).
  • At least one selected from the group may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl or carbon having 6 to 16 carbon atoms. It may be substituted with a heteroaryl of number 2 to 22, an alkyl of 1 to 12 carbons, or a cycloalkyl of 3 to 16 carbons. At least one hydrogen in the compound represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19), or (20) is deuterium.
  • the polycyclic aromatic compound or a multimer thereof according to ⁇ 18> which may be substituted with hydrogen, cyano, or halogen.
  • the polycyclic aromatic compound or a multimer thereof according to ⁇ 18> or ⁇ 19> which comprises at least one tertiary alkyl represented by the following formula (tR).
  • tR tertiary alkyl represented by the following formula (tR).
  • Ra , R b, and R c are independently alkyl having 1 to 24 carbon atoms, and any -CH 2- in the alkyl may be substituted with -O-. , * Is the connection position.
  • X 1 and X 2 are both a> N-R, at least one R of> N-R in which X 1 and X 2 may be the have also be 2-biphenylyl or substituted with substituted
  • ⁇ 22> Consists of an aryl ring and a heteroaryl ring in the compound represented by the formula (12), (13), (14), (15), (16), (17), (18), or (19).
  • At least one selected from the group is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2- in the cycloalkane is-.
  • ⁇ 23> The polycyclic aromatic according to any one of ⁇ 1> to ⁇ 7> and ⁇ 13> to ⁇ 17>, wherein the A ring is a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring.
  • Y 1 is B, or a multimer thereof.
  • ⁇ 26> The polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 25>, or a multimer thereof, wherein the halogen is fluorine.
  • ⁇ 30> A reactive compound in which the polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 29> or a multimer thereof is substituted with a reactive substituent.
  • ⁇ 31> A polymer compound obtained by polymerizing the reactive compound according to ⁇ 30> as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound.
  • ⁇ 32> A pendant type polymer compound in which the main chain type polymer is substituted with the reactive compound according to ⁇ 30>, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked.
  • ⁇ 33> A material for an organic device containing the polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 29> or a multimer thereof.
  • ⁇ 34> A material for an organic device containing the reactive compound according to ⁇ 30>.
  • ⁇ 35> A material for an organic device containing the polymer compound or polymer crosslinked product according to ⁇ 34>.
  • ⁇ 36> A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to ⁇ 32>.
  • ⁇ 37> The material for an organic device according to any one of ⁇ 33> to ⁇ 36>, wherein the material for the organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell. ..
  • ⁇ 38> The material for an organic device according to ⁇ 37>, wherein the material for the organic electroluminescent element is a material for a light emitting layer.
  • ⁇ 39> A composition containing the polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 32> or a multimer thereof, and an organic solvent.
  • ⁇ 40> A composition containing the reactive compound according to ⁇ 30> and an organic solvent.
  • ⁇ 41> A composition containing a main chain polymer, the reactive compound according to ⁇ 33>, and an organic solvent.
  • ⁇ 42> A composition containing the polymer compound or polymer crosslinked product according to ⁇ 31> and an organic solvent.
  • ⁇ 43> A composition containing the pendant-type polymer compound or the pendant-type polymer crosslinked product according to ⁇ 32> and an organic solvent.
  • ⁇ 44> The polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 29> or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes, according to ⁇ 30>.
  • Electromagnetic light emitting element Electromagnetic light emitting element.
  • ⁇ 45> The polycyclic aromatic compound according to any one of ⁇ 1> to ⁇ 29> or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes, according to ⁇ 30>.
  • Electrode emitting element Electrode emitting element.
  • the light emitting layer is a host and the polycyclic aromatic compound as a dopant, a multimer thereof, a reactive compound, a polymer compound, a polymer crosslinked product, a pendant type polymer compound or a pendant type polymer crosslinked product.
  • the organic field light emitting element according to ⁇ 45> which comprises.
  • It has an electron transporting layer and / or an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or fluorantene.
  • the electron transporting layer and / or electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline soil. Contains at least one selected from the group consisting of 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. , ⁇ 48>.
  • the present invention provides a novel polycyclic aromatic compound.
  • the polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for a light emitting layer for forming a light emitting layer of an organic electroluminescent element.
  • By using the compound of the present invention in the light emitting layer it is possible to provide an organic EL device having high efficiency and long life.
  • the chemical structure and the substituent may be represented by the number of carbon atoms, but the number of carbon atoms in the case where the substituent is substituted in the chemical structure or the substituent is further substituted in the substituent is the chemical structure or the substitution. It means the carbon number of each group, and does not mean the total carbon number of the chemical structure and the substituent or the total carbon number of the substituent and the substituent.
  • substituent B of carbon number Y substituted with substituent A of carbon number X means that "substituent A of carbon number X" is substituted with "substituent B of carbon number Y".
  • the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B.
  • substituted with a substituent A means that "substituent A having no limitation on the number of carbon atoms” is substituted with "substituent B having a carbon number Y".
  • the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B.
  • the compounds of the present invention are polycyclic aromatic compounds represented by the following formula (1) or polycyclic aromatic compounds having a plurality of structures represented by the following formula (1). It is a multimer.
  • the A ring, B ring, and C ring in the formula (1) are independently aryl rings or heteroaryl rings, respectively, but at least one selected from the group consisting of A ring, B ring, and C ring.
  • the ring is a fused 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. At least one hydrogen in these rings may be substituted with a substituent.
  • the substituents are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino (with aryl).
  • substituted or unsubstituted diarylboryl two aryls may be attached via a single bond or a linking group
  • substituted or unsubstituted alkyl substituted or unsubstituted cycloalkyl
  • substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl is preferable.
  • substituents include aryl, heteroaryl, alkyl or cycloalkyl, and diarylamino.
  • At least one of the A ring, the B ring and the C ring is a ring having at least one substituent, and each of the A ring, the B ring and the C ring is a ring having at least one substituent. More preferably, it is a ring in which each of the A ring, the B ring and the C ring has one substituent.
  • the substituent a substituted or unsubstituted alkyl (particularly neopentyl), a cycloalkyl such as adamantyl is preferable, and a tertiary-alkyl (tR) is preferable. This is because such a bulky substituent increases the intermolecular distance and thus improves the emission quantum yield (PLQY). Further, as the substituent, diarylamino is also preferable.
  • the tertiary alkyl is represented by the following formula (tR).
  • Ra , R b , and R c are independently alkyl having 1 to 24 carbon atoms, and any -CH 2- in the alkyl may be substituted with -O-.
  • the group represented by the formula (tR) is replaced with at least one hydrogen in the compound or structure represented by the formula (1) in *.
  • alkyl having 1 to 24 carbon atoms may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms.
  • the total number of carbon atoms of Ra , R b , and R c in the formula (tR) of the formula (1) is preferably 3 to 20 carbon atoms, and 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, n-undecyl, Examples thereof include 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n
  • Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-.
  • substituents on the A, B, and C rings include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR) (preferably. Examples thereof include benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a group of formula (tR) or N-carbazolyl.
  • diarylamino include groups described below as the "first substituent".
  • substitution of a group of formula (tR) with diarylamino, carbazolyl and benzocarbazolyl a part or all of hydrogen of the aryl ring or benzene ring in these groups was substituted with the group of formula (tR).
  • the above description of the preferred substituents also applies to the polycyclic aromatic compounds represented by the formulas (2) to (9) and (12) to (19) and their multimers.
  • the aryl ring, heteroaryl ring, or condensed ring in the A ring, B ring, and C ring is a five-membered structure that shares a bond with the condensed bicyclic structure in the center of formula (1) composed of Y 1 , X 1, and X 2. It may have a ring or a 6-membered ring.
  • the "condensed bicyclic structure” means a structure in which two saturated hydrocarbon rings including Y 1 , X 1 and X 2 shown in the center of the formula (1) are condensed.
  • the “6-membered ring that shares a bond with the condensed 2-ring structure” means a 6-membered ring (for example, a benzene ring) condensed into the condensed 2-ring structure.
  • the aryl ring (which is the A ring) or the heteroaryl ring has the 6-membered ring” means that the A-ring is formed only by the 6-membered ring or includes the 6-membered ring. This means that another ring or the like is condensed with this 6-membered ring to form an A ring.
  • the "aryl ring or heteroaryl ring having a 6-membered ring (which is an A ring)" as used herein means that a 6-membered ring constituting all or a part of the A ring is condensed into the condensed two-ring structure. It means that you are doing it.
  • the same explanation applies to "B ring”, “C ring”, and "5-membered ring”.
  • At least one ring selected from the group consisting of A ring, B ring and C ring in the formula (1) is two selected from the group consisting of a monocyclic aryl ring, a cyclopentadiene ring and a monocyclic heteroaryl ring.
  • a condensed ring composed of the above rings (hereinafter, may be referred to as "condensed ring F". ".
  • At least one hydrogen in this condensed ring may be substituted.
  • the present inventors may perform such a condensation. It has been found that the light emission efficiency and the device life can be improved by constructing an organic EL element using a polycyclic aromatic compound having a ring as a material for a light emitting layer.
  • one or two rings selected from the group consisting of A ring, B ring and C ring are preferably fused ring F, and 1 selected from the group consisting of B ring and C ring. More preferably, one or two rings are fused rings F.
  • the number of rings constituting the fused ring F is not particularly limited, but is preferably 2 to 5, and more preferably 2 or 3.
  • Examples of the constitution of the fused ring F include a fused ring of one aryl ring which is a monocyclic ring and one heteroaryl ring which is a monocyclic ring, a fused ring of one aryl ring which is a monocyclic ring and one cyclopentadiene ring, and a monocyclic ring.
  • Examples thereof include a fused ring of two aryl rings and one heteroaryl ring which is a monocycle, and a fused ring of two aryl rings which are monocyclic and one cyclopentadiene ring.
  • the aryl ring which is a monocyclic ring at this time, is preferably a benzene ring.
  • Examples of the monocyclic heteroaryl ring include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrimidine ring, and a pyridazine ring.
  • the fused ring F is preferably a combination of a 6-membered ring and a 5-membered ring. At this time, the 6-membered ring may share a bond with the condensed 2-ring structure described above, or the 5-membered ring may share a bond with the condensed 2-ring structure described above.
  • the fused ring F is not composed only of the cyclopentadiene ring.
  • the cyclopentadiene ring is preferably a 1,1-dimethyl-2,4-cyclopentadiene ring.
  • the ring other than the fused ring F is preferably a monocyclic aryl ring or a monocyclic heteroaryl ring, preferably a benzene ring. It is more preferably a pyridine ring or a pyrimidine ring, and even more preferably a benzene ring.
  • the fused ring F is composed of a heteroaryl ring containing a sulfur atom or an oxygen atom.
  • the fused ring F is a ring represented by the formula (BHet), a ring represented by the formula (DBHet), a ring represented by the formula (PBHet), or a ring represented by the formula (PPHet). Is preferable, and a ring represented by the formula (BHet) or a ring represented by the formula (DBHet) is more preferable.
  • the polycyclic aromatic compound represented by the formula (1) and its multimer are a ring represented by the formula (BHet), a ring represented by the formula (DBHet), and a ring represented by the formula (PBHet).
  • the polycyclic aromatic compound represented by the formula (1) and its multimer are represented by a ring represented by the formula (BHet), a ring represented by the formula (DBHet), and a ring represented by the formula (PBHet) as the condensed ring F. It may contain any one kind of fused ring selected from the group consisting of the ring to be formed and the ring represented by the formula (PPHet), or may contain any two or more kinds of fused rings.
  • R a1 to R a6 are hydrogens or substituents, except that any two or three of R a1 to R a6 adjacent to each other are Y 1 and X 1 in the formula (1). And / or a bond with X 2 , where X is>O,>S,>Se,>NR,> Si (-R) 2, or> C (-R) 2 .
  • the R of>N-R,> Si (-R) 2 , or> C (-R) 2 as X is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted. It may be an alkyl which may be substituted or a cycloalkyl which may be substituted, and the two Rs may be bonded to each other to form a ring.
  • R a1 to R a6 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroaryl.
  • R a1 to R a6 are substituents (other than hydrogen) and the others (excluding those which are the above-mentioned binding agents) are hydrogen, and 0 to 0 of R a1 to R a6. It is more preferable that one is a substituent and the other is hydrogen.
  • a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.
  • X is preferably>O,>S,> NR, or> C (-R) 2 , more preferably>O,> S, or> NR. ,> S is even more preferred.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..
  • the two adjacent R a1 to R a6 that form a bond between Y 1 and X 1 and / or X 2 include R a5 and R a6 , R a2 and R a3 , R a1 and R a2 , and R a3 and Ra4 and the like can be mentioned.
  • R a5 and R a6 , R a2 and R a3 , R a1 and R a2 , and R a3 and Ra4 and the like can be mentioned.
  • rings B and C are rings represented by the formula (BHet)
  • R a5 and R a6 , R a2 and R a3 , R a1 and R a2 Alternatively , it is preferable that R a3 and R a4 serve as a bonder, and it is more preferable that R a5 and R a6 serve as a bonder .
  • formula (BHET) binds to Y 1, X 1, and X 2, R a1, R a2 , and R a3 or, R a2 , R a3 , and R a4 serve as a bond.
  • R a11 to R a18 are hydrogens or substituents, except that any two or three of R a11 to R a18 adjacent to each other are Y 1 and X in the formula (1). It becomes a bond with 1 and / or X 2, and X is>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 , and the above> N.
  • the R of -R,> Si (-R) 2 , or> C (-R) 2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted.
  • R a11 to R a18 are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroaryl.
  • Amino, substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted. It is preferably alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. It is preferable that 0 to 2 of R a11 to R a18 are substituents (other than hydrogen) and the others (excluding those that are the above-mentioned binding agents ) are hydrogen, and 0 to 0 to R a18 of R a11 to R a18.
  • one is a substituent and the other is hydrogen.
  • a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.
  • X is preferably>O,>S,> N-R, or> C (-R) 2 , and is>O,> S, or> C (-R) 2. Is more preferable, and> S or> O is even more preferable.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..
  • the two adjacent R a11 to R a18 that form a bond between Y 1 and X 1 and / or X 2 include R a11 and R a12 , R a12 and R a13 , R a13 and R 14 , R a15 and R. 16, R a16 and R 17, and R a17 and R 18 can be mentioned.
  • R a11 and R a12 , R a12 and R a13 , R a13 and R 14 R a15 and R 16 , R a16 and R 17 , or R a17 and R 18 are the binding hands.
  • the formula (DBHet) is combined with Y 1 , X 1 , and X 2 , and R a11 , R a12 , and R a13 , R. a12, R 13, and R 14, R a15, R 16 , and R a16 or R 16, R a17,, and R 18 is a bond.
  • Z is independently C-R z or N, at least one Z is N, R z, R a26 and R a25 is hydrogen or a substituent, provided that, R z , R a26 and R a25 , any two or three adjacent to each other will be a bond with Y 1 and X 1 and / or X 2 in the formula (1), but R a26 and R are preferable.
  • a25 serves as a bonder
  • X is>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2
  • R is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted. It is a cycloalkyl that may be present.
  • one or two of the four Zs in the formula (PBHet) are N, and it is more preferable that one is N.
  • the two are N, it is preferable that the two N are not adjacent to each other.
  • R z , R a26 and R a25 are hydrogen, or substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino , substituted or unsubstituted.
  • R z , R a26 and R a25 are substituents (other than hydrogen) and the others (excluding those which are the above-mentioned bonds) are hydrogen, and R z , R a26 and It is more preferable that 0 to 1 of R a25 is a substituent and the other is hydrogen.
  • a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.
  • X is preferably>O,>S,> N-R, or> C (-R) 2 , more preferably>O,> S, or> N-R. ,> S, or> O.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..
  • Z is independently C-R z or N, at least one Z is N, R z is hydrogen or a substituent, but any of the adjacent R z .
  • Two or three of are the binders for Y 1 and X 1 and / or X 2 in the formula (1), where X is>O,>S,>Se,>NR,> Si ( -R) 2 or> C (-R) 2 , and the R of>N-R,> Si (-R) 2 , or> C (-R) 2 is independently hydrogen-substituted.
  • Aryl may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted.
  • R z is hydrogen, or substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted.
  • unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted.
  • it is preferably an unsubstituted aryloxy or a substituted silyl.
  • 0 to 2 of R z are substituents (other than hydrogen) and the others (excluding those that form the above-mentioned bond) are hydrogen, and 0 to 0 of R z , R a26 and R a25. It is more preferable that one is a substituent and the other is hydrogen.
  • a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl is preferable.
  • X is preferably>O,>S,> N-R, or> C (-R) 2 , more preferably>O,> S, or> N-R. ,> S, or> O.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..
  • P O
  • P S, Si-R, or Ge-R
  • the atom bonded to the A ring, B ring, or C ring is P, Si, or Ge.
  • X 1 and X 2 in the formula (1) are independently>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, respectively. It is preferable that at least one of X 1 and X 2 in the formula (1) is> NR, both of which are> NR, or one of X 1 and X 2 is> NR. It is more preferable that the other is> C ( ⁇ R) 2 .
  • N-R R in X 1 and X 2 is hydrogen, optionally substituted aryl (except amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl or It is a cycloalkyl which may be substituted, and the R of> Si (-R) 2 is independently hydrogen, an aryl which may be substituted, a heteroaryl which may be substituted, and a substituent. It is an alkyl which may be substituted or a cycloalkyl which may be substituted, and the R of> C (-R) 2 is independently hydrogen, an aryl which may be substituted, and a hetero which may be substituted.
  • Aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, the two Rs are preferably identical, and the two Rs may be bonded to form a ring.
  • the R of> N-R in X 1 and X 2 is preferably an aryl that may be substituted or a heteroaryl that may be substituted.
  • the aryl is preferably phenyl, biphenylyl (particularly 2-biphenylyl), and terphenylyl (particularly terphenyl-2'-yl), and the heteroaryl is benzothienyl (2-benzothienyl, 6-benzo).
  • tertiary-alkyl (particularly t-butyl) represented by the above formula (tR) or cycloalkyl (particularly adamantyl) is preferable.
  • the number of substituents in aryl and heteroaryl is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferable that the aryl ring in the above aryl is condensed with cycloalkane as described later.
  • N-R Rs in X 1 and X 2 are condensed with optionally substituted 2-biphenylyl, optionally substituted terphenyl-2'-yl, and cycloalkane.
  • Aryl which may be substituted
  • 2-biphenylyl which may be substituted 2-biphenylyl substituted with 1 to 3 t-butyl is particularly preferable.
  • terphenyl-2'-yl unsubstituted [1,1': 3', 1'''-terphenyl] -2'-yl is particularly preferable.
  • the aryl condensed with cycloalkane is particularly preferably as follows.
  • the compound of the present invention having R> N-R in the above preferable range as X 1 or X 2 as a light emitting material, the luminous efficiency and the device life can be further improved.
  • X 1 and X 2 are> N-R
  • X 1 and only either one of R of> N-R in X 2 may be substituted 2- biphenylyl or X 1 and X
  • the terphenyl-2'-yl is obtained by substituting only one R of> N-R in 2 or the R of> N-R on both sides.
  • the terphenyl-2'-yl [1,1': 3', 1'''-terphenyl] -2'-yl is preferable.
  • Examples of such a compound include the following compounds (1F-25), compounds (1F-90), and compounds such as compound (1F-90').
  • both X 1 and X 2 are> N-R
  • one of R a> N-R in X 1 and X 2 (optionally substituted) aryl fused with cycloalkane Is also preferable.
  • the other R of> N-R is preferably phenyl which may be substituted.
  • one R of> N-R in X1 and X2 is 2 -biphenylyl which may be substituted, and the other> N-R R is an aryl condensed with a cycloalkane (). It may be substituted).
  • the formed fused ring B'(or fused ring C') is, for example, a carbazole ring, a phenothiazine ring, a phenothiazine ring, or an acridine ring.
  • the above specification is a compound having a ring structure in which X 1 and / or X 2 is incorporated into the condensed ring A', which is represented by the following formula (2-3-2) or formula (2-3-3). But it can be expressed. That is, for example, it is a compound having an A'ring formed by condensing other rings so as to incorporate X 1 (and / or X 2 ) into the benzene ring which is the a ring in the formula (2).
  • the formed fused ring A' is, for example, a carbazole ring, a phenothiazine ring, a phenothiazine ring, or an acridine ring.
  • the B ring and the C ring may be bonded via a single bond or a linking group.
  • the linking group include>O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> N-R and> Si.
  • the Rs of (-R) 2 are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, respectively.
  • the R of> C (-R) 2 is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cyclo. It is alkyl.
  • R in at least one of>N-R,> Si (-R) 2 and> C (-R) 2 is bonded to at least one ring of the B ring and C ring by a linking group or a single bond.
  • the linking group -O-, -S-, or -C (-R) 2 -is preferable.
  • the R of the above-mentioned "-C (-R) 2- " is hydrogen, alkyl, or cycloalkyl.
  • R in at least one of>N-R,> Si (-R) 2 and> C (-R) 2 is bonded to at least one ring of the B ring and C ring by a linking group or a single bond.
  • the above linking group directly bonds the aryl ring and the heteroaryl ring in the B ring and the C ring. It is also preferable that the substituents of the aryl ring and the heteroaryl ring in the B ring and the C ring are bonded via a single bond.
  • Examples of the "aryl ring" which is the A ring, the B ring, and the C ring of the formula (1) include an aryl ring having 6 to 30 carbon atoms, and an aryl ring having 6 to 16 carbon atoms is preferable.
  • An aryl ring of 6 to 12 is more preferable, and an aryl ring having 6 to 10 carbon atoms is particularly preferable.
  • aryl rings include a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring which is a fused bicyclic system, an inden ring, and a terphenyl ring (m-tel) which is a tricyclic system.
  • the fluorene ring, the benzofluorene ring, and the indene ring also include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, and the like are spiro-bonded, respectively.
  • a fluorene ring, a benzofluorene ring, a cyclopentane ring, and the like are spiro-bonded, respectively.
  • alkyl such as methyl as the first substituent described later, respectively
  • the dimethylfluorene ring and the dimethylbenzofluorene ring are respectively.
  • those having a dimethylindene ring are also included.
  • heteroaryl ring which is the A ring, the B ring, and the C ring of the formula (1)
  • examples of the "heteroaryl ring” include a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferable.
  • a heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is further preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable.
  • examples of the "heteroaryl ring” include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • this "heteroaryl ring” is a hetero formed by bonding adjacent groups of "R 1 to R 11 " defined by the formula (2) described later together with an a ring, a b ring or a c ring. Since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total carbon number of the fused ring in which a 5-membered ring is condensed is 6 carbon atoms. It is the lower limit of carbon number.
  • heteroaryl rings include, for example, a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothazole ring, an imidazole ring, an oxazole ring, a thiazazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, and the like.
  • dihydroacridine ring, the xanthene ring, and the thioxanthene ring two of the two hydrogens of methylene are substituted with an alkyl such as methyl as the first substituent described later, respectively, and the dimethyldihydroacridine ring and the dimethyl are substituted.
  • alkyl such as methyl as the first substituent described later
  • a bipyridine ring a phenylpyridine ring, a pyridylphenyl ring, a tricyclic terpyridyl ring, a bispyridylphenyl ring, and a pyridylbiphenyl ring are also mentioned as “heteroaryl rings”.
  • the "heteroaryl ring” shall also include a pyran ring.
  • At least one hydrogen in the "aryl ring” or “heteroaryl ring” is the first substituent, a substituted or unsubstituted “aryl”, a substituted or unsubstituted "heteroaryl”, a substituted or unsubstituted.
  • Diarylamino substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino”, substituted or unsubstituted "diarylboryl (two aryls via a single bond or a linking group) (May be bonded) ", substituted or unsubstituted” alkyl ", substituted or unsubstituted” cycloalkyl ", substituted or unsubstituted” alkoxy ", substituted or unsubstituted” aryloxy ", or substituted Although it may be substituted with “silyl” in the above, “aryl” or “heteroaryl” as the first substituent, aryl of "diarylamino", heteroaryl of "diheteroarylamino", “arylhetero” Examples of the aryl and heteroaryl of "arylamino", the aryl of "diarylboryl",
  • aryl examples include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and aryls 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.
  • aryl examples include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused dicyclic aryl.
  • heteroaryl examples include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, and 2 to 20 carbon atoms. Heteroaryl of 15 is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred.
  • heteroaryl examples include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, dibenzofuranyl, benzo [b] thienyl, dibenzothienyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, synnolyl, quinazolyl, Examples thereof include quinox
  • alkyl as the first substituent may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms.
  • An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 8 carbon atoms is more preferable.
  • Branched chain alkyl having 3 to 8 carbon atoms is more preferable, and 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 (3 to 5 carbon atoms) is particularly preferable. Branched chain alkyl) is 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-.
  • the "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.
  • cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, norbornenyl, and bicyclo [1].
  • alkoxy for example, an alkoxy having a straight chain having 1 to 24 carbon atoms or a branched chain having 3 to 24 carbon atoms can be mentioned.
  • Alkoxy having 1 to 18 carbon atoms is preferable, alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is more preferable.
  • Alkoxy (alkoxy of branched chains having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 5 carbon atoms (alkoxy of branched chains having 3 to 5 carbon atoms) is particularly preferable.
  • alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.
  • substituted silyl for example, silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl can be mentioned.
  • Examples of the "trialkylsilyl” include groups in which each of the three hydrogens in the silyl group is independently substituted with an alkyl, and this alkyl cites the group described as "alkyl” in the first substituent described above. be able to.
  • Preferred alkyls for substitution are alkyls having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.
  • trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethyl Cyril, t-butyldipropylsilyl, t-amyldiethylsilyl, methyld
  • tricycloalkylsilyl examples include groups in which the three hydrogens in the silyl group are independently substituted with cycloalkyl, and this cycloalkyl has been described as "cycloalkyl" in the first substituent described above.
  • the group can be quoted.
  • 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 [.
  • tricycloalkylsilyl examples include tricyclopentylsilyl and tricyclohexylsilyl.
  • dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and the alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls are selected from the specific alkyls and cycloalkyls described above. Examples thereof include silyl in which the group to be substituted is substituted.
  • dialkylarylsilyl substituted with two alkyls and one aryl examples include the specific alkyls described above.
  • silyls substituted with groups selected from aryl examples include triphenylsilyl.
  • aryl in the "diarylboryl” of the first substituent, the above-mentioned description of aryl can be cited.
  • the two aryls may be bonded via a single bond or a linking group (for example,> C (-R) 2 ,>O,> S or> NR).
  • R of> C (-R) 2 and> N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (above, the first substituent), and the first is said.
  • the substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (hereinafter, the second substituent), and specific examples of these groups include aryl and hetero as the first substituent described above. Descriptions of aryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy can be cited.
  • At least one hydrogen in the above may be substituted with a second substituent.
  • the second substituent include aryl, heteroaryl, alkyl, and cycloalkyl, and specific examples thereof include the monovalent group of the above-mentioned "aryl ring” or “heteroaryl ring", and also.
  • a description of "alkyl” or "cycloalkyl” as the first substituent can be referred to.
  • at least one hydrogen in them is aryl such as phenyl (specific example is the group described above), methyl, alkyl such as t-butyl (specific example is described above).
  • Aryl or heteroaryl as a second substituent is also included in a structure substituted with a cycloalkyl (specific example is the group described above) such as (group) or cyclohexyl.
  • a cycloalkyl specifically example is the group described above
  • the second substituent is carbazolyl
  • alkyl such as methyl or cycloalkyl such as cyclohexyl
  • heteroaryl as a substituent.
  • the emission wavelength can be adjusted by the steric hindrance, electron donation and electron attraction of the structure of the first substituent. It is preferably a group represented by the following structural formula, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-.
  • a larger steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, and p-tolyl.
  • 2,4-xylyl, 2,5-xsilyl, 2,6-xsilyl, 2,4,6-mesityl, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, 3,6- Dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.
  • R a Si-R and Ge-R in Y 1 in the formula (1) is aryl, is an alkyl or cycloalkyl, the aryl, group described above can be exemplified as alkyl or cycloalkyl.
  • aryls having 6 to 10 carbon atoms for example, phenyl, naphthyl, etc.
  • alkyls having 1 to 5 carbon atoms for example, methyl, ethyl, etc.
  • cycloalkyls having 5 to 10 carbon atoms preferably cyclohexyl, adamantyl, etc.
  • R of> N-R in X 1 and X 2 in the formula (1), and, R in the> N-R as a connecting group bonding B ring and C ring is substituted with a second substituent described above may, aryl, heteroaryl, alkyl or cycloalkyl (where the aryl as R of> N-R in X 1 and X 2 amino no substitution).
  • Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above.
  • alkyl such as methyl, tertiary butyl, amyl, p-terrary butyl phenyl and the like are preferable.
  • the alkyl substitution position is preferably a para position with respect to the N substitution position.
  • R of NR includes an aryl having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.) which may be substituted with a second substituent, and a carbon which may be substituted with a second substituent.
  • Heteroaryls of number 2 to 15 eg, carbazolyl
  • alkyls of 1 to 5 carbons eg, methyl, ethyl, etc.
  • cycloalkyls of 5 to 10 carbons preferably cyclohexyl or adamantyl
  • the R of> N-R in X 1 and X 2 is particularly preferably the above-mentioned range as the R of> N-R in X 1 and X 2 of the formula (1), and the above-mentioned preferable range is the formulas (7) and (7).
  • the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above.
  • aryls having 6 to 10 carbon atoms for example, phenyl, naphthyl, etc.
  • heteroaryls having 2 to 15 carbon atoms for example, carbazolyl
  • alkyls having 1 to 5 carbon atoms for example, methyl, ethyl, etc.
  • Cycloalkyl preferably cyclohexyl or adamantyl is preferred. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14).
  • X 1 and> in X 2 C (-R) 2 of R, and, as a connecting group bonding ring B and ring C> C (-R) 2 of R of formula (1) is hydrogen, the above-described Aryl, heteroaryl, alkyl or cycloalkyl, which may be substituted with a second substituent.
  • Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above.
  • aryls having 6 to 10 carbon atoms for example, phenyl, naphthyl, etc.
  • heteroaryls having 2 to 15 carbon atoms for example, carbazolyl
  • alkyls having 1 to 5 carbon atoms for example, methyl, ethyl, etc.
  • Cycloalkyl preferably cyclohexyl or adamantyl is preferred. This description will be described in the following equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14).
  • Examples of the linking group in the formula (1) when the linking group that binds the X 1 , X 2 , or the B ring and the C ring is bonded to at least one ring of the A ring, the B ring, and the C ring are used.
  • -O-, -S-, -C (-R) 2 -or single bond, etc. can be mentioned, and the R of "-C (-R) 2- " in these is hydrogen, alkyl, or cycloalkyl.
  • examples of this alkyl or cycloalkyl include the groups described above.
  • an alkyl having 1 to 5 carbon atoms for example, methyl, ethyl, etc.
  • a cycloalkyl having 5 to 10 carbon atoms preferably cyclohexyl or adamantyl
  • the present invention is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the formula (1), preferably the formulas (2), (3), (4), (5), which will be described later.
  • (6) (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1) ), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20) It relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by -1).
  • the multimer is preferably a dimer, more preferably a dimer, and particularly preferably a dimer.
  • the multimer may be in a form having a plurality of the above unit structures in one compound.
  • the multimer is a single bond, and a plurality of the unit structures are bonded by a linking group such as alkylene, phenylene, naphthylene and the like having 1 to 3 carbon atoms.
  • any ring (A ring, B ring or C ring, or a ring, b ring or c ring, etc.) included in the unit structure is shared by a plurality of unit structures.
  • ring-shared multimer ring-shared multimer
  • any ring A ring, B ring or C ring, or a ring, b ring or c ring
  • they may be in the form of being bonded in such a way that they are condensed (ring-condensed multimer)
  • a ring-covalent multimer and a ring-condensed multimer are preferable, and a ring-covalent multimer is more preferable.
  • the structure represented by the formula (9) described later can be given.
  • the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the formula (1) and its multimer may be deuterium, cyano, or halogen in whole or in part.
  • Alkyl, cycloalkyl, aryl) hydrogen can be replaced with deuterium, cyano or halogen, of which all or part of the hydrogen in aryl or heteroaryl is replaced with deuterium, cyano, or halogen.
  • the halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. From the viewpoint of durability, it is also preferable that all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the formula (1) and its multimer is deuterium.
  • polycyclic aromatic compound represented by the formula (1) and its multimer the following formulas (2), (3), (4), (5), (6), (7), (8) ) Or (9), polycyclic aromatic compounds and their multimers, and the following formulas (12), (13), (14), (15), (16), (17), (18) ( 19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), ( 9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-) Examples thereof include polycyclic aromatic compounds represented by 1), (18-1), (19-1) and (20-1) and their multimers.
  • R 1 to R 17 , R 21 to R 24 , R 31 to R 34 and R 41 to R 44 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls via a single bond or a linking group). , Alkoxy, cycloalkyl, alkoxy, aryloxy, or substituted silyls, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • adjacent groups of R 1 to R 3 are bonded to each other to form the a ring
  • the adjacent groups of R 8 to R 11 are bonded to each other to form the b ring of R 4 to R 7 .
  • Adjacent groups are bonded to each other to form a ring c
  • adjacent groups of R 12 to R 14 are bonded to each other to form a12 ring
  • adjacent groups of R 15 to R 17 are bonded to each other to form a ring b15.
  • adjacent groups of R 21 to R 24 are bonded to each other with the c21 ring
  • adjacent groups of R 31 to R 34 are bonded to each other with the b31 ring
  • R 41 to R 44 are bonded to each other with the b31 ring
  • Adjacent groups of the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b41 ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, or dihetero.
  • Arylamino, aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, It may be substituted with dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • At least one set of two adjacent groups of R 1 to R 11 are combined to form a divalent group represented by the formula (Het).
  • the R 4 and R 5 and R 6 and R 7 constitute a divalent group represented by the formula (Het) simultaneously, as well as the R 8 and R 9 and R 10 and R 11 simultaneously It is excluded when it constitutes a divalent group represented by the formula (Het). That is, neither the b ring nor the c ring is formed by combining two divalent groups represented by two or more formulas (Het) to form a three-ring condensed ring.
  • at least one set of two adjacent groups of R 1 to R 3 and R 9 to R 17 are combined to form a divalent group represented by the formula (Het). There is.
  • R 1 to R 17 , R 21 to R 24 , R 31 to R 34 and R 41 to R 44 are independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, and diallylamino (where aryl is aryl having 6 to 12 carbon atoms), respectively.
  • Diarylboryl where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group
  • an alkyl having 1 to 24 carbon atoms and an alkyl having 3 to 24 carbon atoms.
  • Cycloalkyl or trialkylsilyl (where alkyl is an alkyl having 1 to 6 carbon atoms) is preferred. Further, adjacent groups of R 1 to R 3 are bonded to each other to form a ring, and adjacent groups of R 8 to R 11 are bonded to each other to form a ring b, of which R 4 to R 7 are formed. Adjacent groups are bonded to each other to form a c ring, adjacent groups of R 12 to R 14 are bonded to each other to form an a12 ring, and adjacent groups of R 15 to R 17 are bonded to each other to form a b15 ring.
  • adjacent groups of R 21 to R 24 are bonded to each other to form a c21 ring, and adjacent groups of R 31 to R 34 are bonded to each other to form a b31 ring, and of R 41 to R 44 .
  • Adjacent groups may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, respectively, together with the b41 ring, and at least one hydrogen in the formed ring may be formed.
  • Aryl with 6 to 10 carbon atoms, alkyl with 1 to 12 carbon atoms, cycloalkyl with 3 to 16 carbon atoms or trialkylsilyl (where alkyl is alkyl with 1 to 4 carbon atoms) may be substituted.
  • R 2 in the formulas (2), (3), (4), (5) and (6) is alkyl (methyl, t-butyl, etc.), substituted phenyl (2,6, dimethylphenyl, etc.), diarylamino ( It is preferably diphenylamino or the like) or carbazolyl (N-carbazolyl or the like). Further, it is preferable that R 1 and R 3 , which are groups other than R 2 in the a ring, are hydrogen, respectively.
  • Equation (2) (Equation (Het)), Equation (3), Equation (4), Equation (5), Equation (6), Equation (7) (Equation (Het)), Equation (8), and Equation ( 9)
  • X is>O,>S,>Se,>NR,> Si (-R) 2 , or> C (-R) 2 .
  • the R of>N-R,> Si (-R) 2 , or> C (-R) 2 as X is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl.
  • Aryl which may be substituted or cycloalkyl which may be substituted an aryl having 6 to 30 carbon atoms which may be substituted, a heteroaryl which may be substituted and having 2 to 30 carbon atoms, substituted. It is preferably an alkyl having 1 to 24 carbon atoms which may be substituted, or a cycloalkyl having 3 to 24 carbon atoms which may be substituted.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. .. Further, X is preferably>O,>S,> N-R, or> C (-R) 2 , more preferably>O,>S,> N-R, and> S, or. > O is even more preferred.
  • R b1 and R b2 are hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group).
  • Can be alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, where * is.
  • R b1 and R b2 are hydrogen, aryls having 6 to 30 carbon atoms, heteroaryls having 2 to 30 carbon atoms, diallylamino (where aryls are aryls having 6 to 12 carbon atoms), and diallylboryls (provided that they are arylboryls).
  • Aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or It is preferably a trialkylsilyl (where alkyl is an alkyl having 1 to 6 carbon atoms).
  • R 7 and R 8 in formula (2), R 8 and R 24 in formula (3), or R 34 and R 24 in formula (5) are combined to form a single bond,>O,>NR,>. Even if Si (-R) 2 ,> C (-R) 2 ,> S, or> Se (preferably>O,>N-R,> C (-R) 2 , or> S) Good.
  • a 6-membered ring is formed from Y 1 , (a part of) c ring, the binding site of R 7 and R 8 and (a part of) b ring.
  • N-R and> Si (-R) 2 R independently have an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a carbon number of carbon atoms.
  • the number 3 to 14 is cycloalkyl, and the R in at least one of>N-R,> Si (-R) 2 , and> C (-R) 2 is -O-, -S-, It may be bonded to at least one ring of the b ring and the c ring by -C (-R) 2- or a single bond.
  • the R of> N-R is preferably an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
  • the R of> C (—R) 2 is preferably hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
  • P S, Al, Ga, As, Si-R, or Ge-R
  • the R of Si-R and Ge-R is an aryl having 6 to 12 carbon atoms and an alkyl having 1 to 6 carbon atoms. Alternatively, it is a cycloalkyl having 3 to 14 carbon atoms.
  • Equation (2), (3), (4), (5), X 1, X 2 in (6), and, (7), (8) X 1 in and (9), X 2, X 3 and X 4 are independently>O,>NR,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the above-mentioned> NR and> Se.
  • R of Si (-R) 2 is independently hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl having 2 to 15 carbon atoms which may be substituted, and substituted.
  • R of> C ( ⁇ R) 2 is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted. It is a heteroaryl having 2 to 15 carbon atoms which may be substituted, an alkyl having 1 to 6 carbon atoms which may be substituted, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted.
  • R in at least one of>N-R,> Si (-R) 2 and> C (-R) 2 is -O-, -S-, -C (-R) 2- , or simply.
  • R in at least one of "the above>N-R,> Si (-R) 2 and> C (-R) 2 in the formula (1) is the A ring, the B ring and the A ring, the B ring and The provision that "it is bonded to at least one ring of C ring" is defined in the formula (2), (3), (4), (5), (6), (7), (8) or (9). Then, "R in at least one of>N-R,> Si (-R) 2 and> C (-R) 2 is -O-, -S-, -C (-R) 2- or a single bond.
  • At least one ring selected from the group consisting of a 5-membered ring that condenses with an a ring, a b ring, a c ring, an a12 ring, a b15 ring, a c21 ring, a 5-membered ring that condenses with a b31 ring, and a b41 ring.
  • a 5-membered ring that condenses with an a ring, a b ring, a c ring, an a12 ring, a b15 ring, a c21 ring, a 5-membered ring that condenses with a b31 ring, and a b41 ring.
  • X 1 , X 2 , X 3 , and X 4 are independently>O,>NR,> C (-R) 2 , or> S, and the R of> NR is It is preferably an aryl having 6 to 10 carbon atoms which may be substituted, an alkyl having 1 to 4 carbon atoms which may be substituted, or a cycloalkyl having 5 to 10 carbon atoms which may be substituted.
  • the R of C (-R) 2 is hydrogen, an aryl having 6 to 10 carbon atoms which may be substituted, an alkyl having 1 to 4 carbon atoms which may be substituted, or 5 carbon atoms which may be substituted. It is preferably about 10 cycloalkyl.
  • At least one (a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, and b41 ring, the formed ring, at least one of the aryl and the heteroaryl) is. It may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane has an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and 1 carbon atom. It may be substituted with an alkyl of ⁇ 24 or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH 2- in the cycloalkane may be substituted with -O-.
  • the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane has 6 to 6 carbon atoms. It is preferably a cycloalkane that may be substituted with 16 aryl, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.
  • At least one hydrogen in the compound represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) is deuterium, cyano or It may be replaced with halogen.
  • the compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), and (9) are each represented by the above formula (tR). It is preferable that the structure contains at least one tertiary alkyl.
  • the substituents of the ring to which R b1 , R b2 , and Formula Het are bonded in each of the formulas (2) and (7), and R 21 to each of the formulas (3) and (4) Any one or more of R 24 , any one or more of R 21 to R 24 and R 31 to R 34 in each of the formulas (5) and (6), and any one of R 41 to R 44 in the formula (8).
  • R 31 to R 34 and R 41 to R 44 in the formula (9) are represented by the above formula (tR), such as tertiary-alkyl (t-butyl or t-amyl). ), Neopentyl or adamantyl-containing substituents are preferred.
  • polycyclic aromatic compounds represented by the formulas (2), (3), (4), (5), (6), (7), (8), or (9) or their multimers the formulas
  • the polycyclic aromatic compound represented by (3), (4), (5), (6), (7), (8), or (9) or a multimer thereof is more preferable, and the formula (3), The polycyclic aromatic compound represented by (4) or a multimer thereof is more preferable.
  • R 1 ⁇ R 3 and R 8 ⁇ R 11 is , Independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl , Alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. ..
  • R 1 ⁇ R 3 and R 8 ⁇ R 11 are each independently hydrogen, aryl of 6 to 30 carbon atoms, heteroaryl of 2-30 carbon atoms, diarylamino (where aryl is an aryl having 6 to 12 carbon atoms ), Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), or an alkyl having 1 to 24 carbon atoms. preferable.
  • R 51 to R 58 and R 61 to R 68 are , Independently, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl , Cycloalkyl, alkoxy, aryloxy, or substituted silyls, wherein at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
  • R 51 to R 58 and R 61 to R 68 are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, and diarylamino (where aryl is aryl with 6 to 12 carbon atoms). ), Diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and 3 to 24 carbon atoms. It is preferably 24 cycloalkyl or trialkylsilyl (where alkyl is an alkyl having 1 to 6 carbon atoms).
  • Equation (12), (13), (14), (15), (16), (17), (18), (19) and (20) in the adjacent groups of R 1 ⁇ R 3 together Are bonded together with the a ring, adjacent groups of R 8 to R 11 are bonded to each other with the b ring, and adjacent groups of R 51 to R 54 are bonded to each other with the c51 ring, and the R 55 Adjacent groups of ⁇ R 58 are bonded together with the c55 ring, adjacent groups of R 61 to R 64 are bonded together with the b61 ring, and adjacent groups of R 65 to R 68 are bonded together.
  • aryl rings or a heteroaryl ring may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b65 ring, respectively, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, aryl.
  • Heteroarylamino, diarylboryl two aryls may be attached via a single bond or a linking group
  • alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyls may be substituted.
  • the aryl ring or heteroaryl ring formed is preferably an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring has 6 to 10 carbon atoms. It may be substituted with aryl, alkyl having 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl having 3 to 16 carbon atoms (where alkyl is alkyl having 1 to 4 carbon atoms).
  • Equation (12), (13), (14), (15), (16), (17), (18), (19) and R 2 is in (20), alkyl (methyl, t- butyl, etc.) , Substituted phenyl (2,6, dimethylphenyl, etc.), diarylamino (diphenylamino, etc.) or carbazolyl (N-carbazolyl, etc.). Further, it is preferable that R 1 and R 3 , which are groups other than R 2 in the a ring, are hydrogen, respectively.
  • X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C (-R) 2 .
  • the R of>N-R,> Si (-R) 2 , or> C (-R) 2 is hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, preferably an 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.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. .. Further, X is preferably>O,>S,> N-R, or> C (-R) 2 , more preferably>O,> S, or> N-R, and> O or. > S is even more preferred.
  • Y 1 is independently B and P, respectively.
  • P O
  • P S, Al, Ga, As, Si-R, or Ge-R
  • R of the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms and 1 to 1 to carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms.
  • B, P, P O
  • X 1 and X 2 are independent of each other. >O,>N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the R of> N-R and> Si (-R) 2 is Independently, hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, a heteroaryl which may have 2 to 15 carbon atoms which may be substituted, and an alkyl having 1 to 6 carbon atoms which may be substituted.
  • R of> C (-R) 2 is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and is substituted. It may be a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms which may be substituted, or a cycloalkyl having 3 to 14 carbon atoms which may be substituted, and the above-mentioned> NR.
  • the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is carbon.
  • a cycloalkane that may be substituted with an aryl of number 6 to 16, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.
  • At least one hydrogen in the compound represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19) or (20) is deuterium.
  • the compounds represented by the formulas (12), (13), (14), (15), (16), (17), (18), (19) or (20) are represented by the above formula (tR). It is preferable that the structure contains at least one tertiary alkyl represented. In particular, in each of the formulas (12), (13), (14), (15), (16), (17), (18), (19) and (20), R 51 to R 58 and R 61 It is preferable that any of 1 to R 68 is a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.) represented by the above formula (tR), neopentyl, or adamantyl.
  • Aryl, Heteroaryl, Diarylamino, Diheteroarylamino, Arylheteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryl It is an oxy, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
  • R z is independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, diarylamino (where aryl is aryl with 6 to 12 carbon atoms), and diallylboryl (where aryl is carbon). It is preferably an aryl of number 6-12, and the two aryls may be bonded via a single bond or a linking group), or an alkyl having 1 to 24 carbon atoms.
  • At least one hydrogen in the formed ring may be aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls bonded via a single bond or a linking group). It may be substituted), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl.
  • the aryl ring or heteroaryl ring formed is preferably an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring has 6 to 10 carbon atoms. It may be substituted with aryl, alkyl having 1 to 12 carbon atoms, or cycloalkyl or trialkylsilyl having 3 to 16 carbon atoms (where alkyl is alkyl having 1 to 4 carbon atoms).
  • the ring (monocycle) containing Z, which is N is preferably a pyridine ring or a pyrimidine ring.
  • a'ring is a ring containing Z which is N
  • a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable.
  • X is independently>O,>S,>Se,>N-R,> Si (-R) 2 , or> C. (-R) 2 .
  • the Rs of>N-R,> Si (-R) 2 or> C (-R) 2 are independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, and the two Rs are bonded to each other.
  • Aryl may have 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.
  • R in NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl.
  • R in C (—R) 2 is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and further preferably an unsubstituted methyl. ..
  • X is preferably>O,>S,> N-R, or> C (-R) 2 , more preferably>O,> S, or> N-R, and> O or. > S is even more preferred.
  • R of the Si—R and Ge—R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
  • Equations (2-1), (3-1), (4-1), (5-1), (6-1), (10-1), (11-1), (12-1), ( X in 13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) 1 and X 2 and X 1 , X 2 , X 3 and X 4 in equations (7-1), (8-1) and (9-1) are independently> O, respectively.
  • >N-R,> Si (-R) 2 ,> C (-R) 2 ,> S, or> Se, and the R of> N-R and> Si (-R) 2 are independent of each other.
  • the aryl may be substituted with 6 to 12 carbon atoms
  • the heteroaryl may be substituted with 2 to 15 carbon atoms
  • the alkyl may be substituted with 1 to 6 carbon atoms, or the moiety is substituted.
  • It is a cycloalkyl having 3 to 14 carbon atoms
  • R of> C (-R) 2 is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted, and 2 carbon atoms which may be substituted.
  • R in at least one of R) 2 and> C (-R) 2 is -O-, -S-, -C (-R) 2- , or by a single bond, a'ring, b'ring, At least one selected from the group consisting of a c'ring, an a12'ring, a b15'ring, a 5-membered ring fused to a c21'ring, a 5-membered ring fused to a b31'ring, a c51'ring, and a b61'ring. It may be bonded to the ring.
  • a'ring, b'ring, c'ring selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by (19-1) or (20-1)
  • At least one) may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane has an aryl having 6 to 30 carbon atoms and 2 to 30 carbon atoms. It may be substituted with heteroaryl, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH 2- in the cycloalkane may be substituted with -O-.
  • At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound represented by (19-1) or (20-1) is condensed with at least one cycloalkane
  • One cycloalkane is a cycloalkane having 3 to 20 carbon atoms
  • at least one hydrogen in the cycloalkane has an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, and 1 to 12 carbon atoms. It is preferably a cycloalkane that may be substituted with an alkyl or a cycloalkyl having 3 to 16 carbon atoms.
  • At least one hydrogen in the compounds represented by (19-1) and (20-1) may be substituted with deuterium, cyano, or halogen.
  • the compound represented by 1), (19-1) or (20-1) is a tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl represented by the above formula (tR).
  • a structure containing at least one is preferable.
  • the compound (1F-86) and the compound (1F-87) of the examples are a ring (pyridine ring) containing Z in which only the a'ring is N in the formulas (4-1) and (13-1), respectively. It corresponds to the compound which is.
  • Examples (Table 2) it can be seen that an organic EL device using these compounds in the light emitting layer has a long time to maintain high brightness and can improve the device life.
  • At least one of the aryl and heteroaryl rings in the chemical structure of the compound and its multimers may be condensed with at least one cycloalkane.
  • Aryl moiety) and heteroaryl (heteroaryl, diheteroarylamino or heteroaryl moiety in aryl heteroarylamino), a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, (as above) aryl (as above) and heteroaryl in the first and second substituent to b65 ring, the Si-R and Ge-R is Y 1 R Aryl as R (similar to above), and aryl as R of>N-R,> Si (-R) 2 and> C (-R) 2 which are X 1 , X 2 , X 3 , X 4 At least one of (similar to above) and heteroaryl (similar to above) may be condensed with at least one cycloalcan.
  • Aryl ring which is a ring, b'ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring.
  • heteroaryl ring aryl (aryl moiety in aryl, diarylamino, diarylboryl or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituent in rings A to C.
  • Aryl unsame as above
  • heteroaryl as the first substituents on rings a to c
  • X 1 , X 2 , X 3 , X 4 > NR. ,> Si (-R) 2 and> C (-R) 2 as R, at least one of aryl (same as above) and heteroaryl (similar to above) is condensed with at least one cycloalcan. You may.
  • X 2 , X 3 , X 4 >N-R,> Si (-R) 2 and> C (-R) 2 at least one of the aryls as R (similar to the above) is at least 1. It may be condensed with one cycloalgecan.
  • cycloalkane examples include 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, and cycloalkanes having 5 to 10 carbon atoms. Examples thereof include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.
  • cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo [1.0.1] butane, bicyclo [1.1.1] pentane, Bicyclo [2.0.1] pentane, bicyclo [1.2.1] hexane, bicyclo [3.0.1] hexane, bicyclo [2.1.2] heptane, bicyclo [2.2.2] octane, Examples thereof include adamantane, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (particularly methyl) substituents, halogen (particularly fluorine) substitutes and dehydrohydrone substitutes having 1 to 5 carbon atoms thereof.
  • At least one hydrogen in the ⁇ -position carbon of cycloalkane (the carbon at the position adjacent to the carbon at the condensation site in the cycloalkyl condensed on the aryl ring or the heteroaryl ring) as shown in the following structural formula, for example.
  • the structure in which is substituted is preferable, the structure in which two hydrogens are substituted in the carbon at the ⁇ -position is more preferable, and the structure in which a total of four hydrogens are substituted in the carbon at the ⁇ -position is further preferable.
  • this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.
  • the number of cycloalkanes condensed on one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
  • a cycloalkanes are condensed on one benzene ring (phenyl) is shown below. * Indicates the bond position and may be any carbon that constitutes a benzene ring and does not constitute a cycloalkane.
  • Cycloalkanes condensed as in the formulas (Cy-1-4) and (Cy-2-4) may be condensed with each other.
  • the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Is the same.
  • At least one -CH 2- in the cycloalkane may be substituted with -O-.
  • a cycloalkane condensed on one benzene ring (phenyl) is shown below. Even if the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the 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, and the substituents include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded). (Or may be attached via a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, dehydrogen, cyano or halogen, the details of which are described above in the first substituent. The explanation can be quoted.
  • alkyl for example, alkyl having 1 to 6 carbon atoms
  • cycloalkyl for example, cycloalkyl having 3 to 14 carbon atoms
  • halogen for example, fluorine
  • deuterium and the like are preferable.
  • cycloalkyl when cycloalkyl is substituted, a substituted form forming a spiro structure may be used, and an example thereof is shown below.
  • Aryl ring and heteroaryl which are (ring, c'ring, c21'ring, b31'ring, b15'ring, a12'ring, b41'ring, c51'ring, c55'ring, b61'ring, b65'ring).
  • Examples thereof include a ring, an aryl ring in a condensed ring, and a heteroaryl ring condensed with cycloalkane.
  • the b-ring of formula (3) particularly as R 9 and R 10 combine to form a ring
  • the c21 ring of formula (3), and the b-ring of formula (4) particularly R 9 and R 10
  • the c21 ring of the formula (4) (particularly so that R 22 and R 23 are bonded to form a ring) is condensed with a cycloalkane (so that they are bonded to form a ring).
  • cycloalkane condensation include formulas (1) or (2), (3), (4), (5), (6), (7), (8), (9), (12). ), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1) ), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), Tables of (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), or (20-1).
  • the polycyclic aromatic compound and its multimer are, for example,> NR in which R is condensed with cycloalkane> NR, diarylamino condensed with cycloalkane (condensed to this aryl moiety), cycloalkane.
  • Examples include condensed carbazolyl (condensed on this benzene ring portion) or benzocarbazolyl condensed with cycloalkane (condensed on this benzene ring portion).
  • Examples of the "diarylamino" include the groups described as the "first substituent" above.
  • family compound and R 2 in the multimers eg a condensed diarylamino with cycloalkane (this condensation to aryl moiety) or fused carbazolyl with cycloalkane (fused to the benzene ring portion) and the like.
  • n is an independently integer of 1 to 3 (preferably 1)
  • At least one of the a ring, the b ring and the c ring is the equation (2), (3), (4), (5), (6), (7), (8). ), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3) -1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1) ), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), Alternatively, it shall be a fused ring according to the provisions of (20-1).
  • Cy in the following formula represents cycloalkane
  • Cy- (1) it means that n cycloalkanes are condensed at an arbitrary position on each benzene ring).
  • each compound may be substituted with the above-mentioned first substituent and second substituent.
  • at least one of the rings bonded to the element corresponding to Y 1 in the formula (1) is the formulas (2), (3), (4), (5), (6), ( 7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2- 1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1) , (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), ( A condensation composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring according to the provisions of 19-1) or (20-1). It shall be a ring.
  • the polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device.
  • the organic device include an organic electroluminescent device, an organic field effect transistor, and an organic thin film solar cell.
  • an organic electroluminescent device as a dopant material for the light emitting layer, a compound in which Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is> NR in any of the above formulas.
  • Y 1 is B
  • X 1 (and X 4 or X 3 ) is> O
  • X 2 (and X 3 or X 4 ) is> NR
  • Y 1 is B
  • Compounds in which X 1 and X 2 (and X 3 and X 4 ) are> O are preferred, with Y 1 being B, X 1 and X 2 (and X 3 and X 4 ) being> O as electron transport materials.
  • Compounds, compounds in which Y 1 is P O, X 1 and X 2 (and X 3 and X 4 ) are> O, are preferably used.
  • a more specific example of the polycyclic aromatic compound of the present invention is a compound represented by the following structural formula.
  • “D” indicates deuterium
  • “Me” indicates methyl
  • “tBu” indicates t-butyl
  • “tAm” indicates t-amyl.
  • the polycyclic aromatic compound represented by the formula (1) and its multimer according to the present invention are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted therein as a monomer (this polymer).
  • the monomer for obtaining a compound has a polymerizable substituent) or a polymer crosslinked product obtained by further cross-linking the polymer compound (the polymer compound for obtaining this polymer crosslinked product has a crosslinkable substituent).
  • a material for an organic device can also be used as a pendant type polymer crosslinked product obtained by further cross-linking the pendant type polymer compound (the pendant type polymer compound for obtaining this pendant type polymer crosslinked product has a crosslinkable substituent).
  • it can be used as a material for an organic field light emitting element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
  • reactive substituent including the polymerizable substituent, the crosslinkable substituent, and the reactive substituent for obtaining a pendant type polymer, hereinafter, also simply referred to as “reactive substituent”).
  • the group is not particularly limited, but alkenyl, alkynyl, an unsaturated compound of cycloalkyl (for example, cyclobutenyl), a group in which at least one -CH 2- in cycloalkyl is substituted with -O- (for example, epoxy) is condensed.
  • examples thereof include an unsaturated compound of cycloalkane (for example, condensed cyclobutene), and substituents having the following structure are preferable. * In each structural formula indicates the bonding position.
  • substituents it is represented by the formula (XLS-1), the formula (XLS-2), the formula (XLS-3), the formula (XLS-9), the formula (XLS-10) or the formula (XLS-17).
  • the group represented by the formula (XLS-1), the formula (XLS-3) or the formula (XLS-17) is more preferable.
  • polymer compounds and polymer crosslinked bodies Details of the uses of such polymer compounds, polymer crosslinked bodies, pendant type polymer compounds and pendant type polymer crosslinked bodies (hereinafter, also simply referred to as “polymer compounds and polymer crosslinked bodies”) will be described later.
  • a reaction for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used.
  • At least one ring selected from the group consisting of A ring, B ring and C ring by using a raw material having a desired fused ring or adding a step of condensing the ring somewhere in the reaction step.
  • the compound can be produced from a fused 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, the description of International Publication No. 2015/102118 can be referred to.
  • reaction step of exchanging said metal and Y 1 using a reagent selected from the group consisting of aryloxy compound of alkoxides and Y 1, wherein the continuous electrophilic aromatic substitution using a Bronsted base method comprising a reaction step of coupling the B ring and C ring Y 1.
  • the polycyclic aromatic compound of the present invention is preferably produced by a production method including a reaction step of reacting the following intermediate-2 with an acid.
  • Z is —B (OH) 2 which may be esterified.
  • Z in Intermediate-2 is —B (OH) 2 , which may be esterified.
  • Preferred Y 1 is an esterified group of —B (OH) 2 .
  • the group in which -B (OH) 2 is esterified (-B (OR) 2 ) is not particularly limited, and examples thereof include groups obtained by the reaction of an alcohol containing a diol or a carboxylic acid with boronic acid. Be done.
  • R of ⁇ B (OR) 2 include alkyls having 1 to 4 carbon atoms (branched chain alkyls having 3 to 4 carbon atoms) which may be substituted, and Rs are bonded to each other to form a ring.
  • the formed ring may contain an aromatic ring such as benzene.
  • the basis of the following structure can be mentioned. In the following structure, "Me” represents methyl, “Et” represents ethyl, "iPr” represents isopropyl, and * represents the binding position.
  • the compound represented by Intermediate-2 (boronic acid or boronic acid ester) is basically a ring A (ring a) and a ring B (b).
  • An intermediate is produced by binding the ring) and the C ring (c ring) with a bonding group (X 1 and X 2 ) (first reaction), and then the Y 1 group is introduced to first obtain boronic acid.
  • An ester can be produced, and the boronic acid can be produced by hydrolyzing the ester.
  • a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction
  • a general reaction such as a Buchwald-Hartwig reaction
  • the symbols in the structural formulas in each scheme shown below are the same as the above definitions.
  • the second reaction is to introduce a boronic acid ester such as shown in the following scheme (1) or (2) is Y 1 to the intermediate obtained in the first reaction Bpin (pinacolato boryl) reaction Is.
  • the hydrogen atom is first orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like to be lithiated.
  • n-butyllithium, sec-butyllithium, t-butyllithium, etc. alone has been shown, but N, N, N', N'-tetramethylethylenediamine, etc. are added in order to improve the reactivity. You may.
  • boronic acid can be produced by hydrolyzing the boronic acid ester produced by the method of the above scheme (1) or (2).
  • the above schemes (1) and (2) show a method for producing a boronic acid ester represented by the formula (1) or (2), but have a structure represented by the formula (1) or (2).
  • a multimeric compound having a plurality of esters can be produced by using an intermediate compound having a plurality of A ring (a ring), B ring (b ring) and C ring (c ring). Details will be described in the following schemes (5) to (7).
  • the target product such as a dimer compound or a trimer compound can be obtained by doubling or tripling the amount of the reagent such as butyllithium to be used.
  • the boronic acid compound can be produced by hydrolysis according to the above scheme (4), and different ester compounds can also be produced. It can be produced through transesterification or re-esterification using alcohol.
  • Boronic acid or boronic acid ester having a substituent at a desired position can be synthesized by appropriately selecting the above-mentioned synthesis method and appropriately selecting the raw material to be used.
  • lithium was introduced to a desired position by orthometalation, but as in the following schemes (8) or (9), a halogen such as a bromine atom is added to the position where lithium is to be introduced. Lithium can also be introduced at the desired position by introducing and halogen-metal exchange. Then, a boronic acid ester can be produced from the obtained lithium product.
  • a halogen such as a bromine atom
  • the halogen atom is first lithiated by performing a halogen-lithium exchange reaction with n-butyllithium, sec-butyllithium, t-butyllithium or the like.
  • a method using n-butyllithium, sec-butyllithium, t-butyllithium, etc. alone has been shown, but N, N, N', N'-tetramethylethylenediamine, etc. are added in order to improve the reactivity. You may.
  • the above schemes (8) and (9) show a method for producing a boronic acid ester represented by the formula (1) or (2), and the boronic acid ester thus obtained is hydrolyzed. By doing so, boronic acid can be produced (see scheme (3) or (4) above). Further, by allowing an appropriate alcohol to act on these boronic acid esters and boronic acids, different boronic acid esters can be produced through transesterification or reesterification. Further, the multimeric compound having a plurality of structures represented by the formula (1) or (2) is also an intermediate having a plurality of A ring (a ring), B ring (b ring) and C ring (c ring). Can be produced by using (see the above schemes (5) to (7)).
  • the bromoated product and bis (pinacolato) diboron or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane and the like are subjected to a palladium catalyst.
  • Boronic acid esters can also be synthesized in the same manner by performing a coupling reaction using and bases.
  • the above schemes (10) and (11) show a method for producing a boronic acid ester represented by the formula (1) or (2), and the boronic acid ester thus obtained is hydrolyzed. By doing so, boronic acid can be produced (see scheme (3) or (4) above). Further, by allowing an appropriate alcohol to act on these boronic acid esters and boronic acids, different boronic acid esters can be produced through transesterification or reesterification. Further, the multimeric compound having a plurality of structures represented by the formula (1) or (2) is also an intermediate having a plurality of A ring (a ring), B ring (b ring) and C ring (c ring). Can be produced by using (see the above schemes (5) to (7)).
  • the metallizing reagents used in the halogen-metal exchange reaction in the schemes described so far include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, isopropylmagnesium chloride, and bromide. Examples thereof include isopropylmagnesium, phenylmagnesium chloride, phenylmagnesium bromide and a lithium chloride complex of isopropylmagnesium chloride known as a turbo Grignard reagent.
  • the metallizing reagents used in the orthometal exchange reaction in the schemes described so far include lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hex.
  • examples thereof include organic alkaline compounds such as methyldisilazide, lithium tetramethylpiperidinylmagnesium chloride / lithium chloride complex, and lithium tri-n-butylmagnate.
  • examples thereof include N and N-dimethylpropylene urea.
  • the boronic acid or boronic acid ester of the present invention includes those in which at least a part of hydrogen atoms are substituted with deuterium and those in which halogens such as fluorine and chlorine are substituted.
  • Compounds and the like can be synthesized in the same manner as described above by using a raw material in which desired portions are deuterated, fluorinated or chlorinated.
  • a polycyclic aromatic compound is produced by reacting a boronic acid or a boronic acid ester represented by an intermediate-2 compound or the like with a Lewis acid such as aluminum chloride. Can be done.
  • Bronsted acids such as p-toluenesulfonic acid can also be used.
  • a base such as diisopropylethylamine may be added in order to improve the selectivity and yield.
  • a polycyclic aromatic multimeric compound can also be produced by using the multimeric compounds having a plurality of structures represented by intermediate-2 by the methods shown in the following schemes (14) to (16). ..
  • the target product such as a dimer compound or a trimer compound can be obtained by doubling or triple the amount of the reagent such as aluminum chloride used according to the structure of the multimer compound. it can.
  • the Lewis acids used in the above schemes (12) to (16) include AlCl 3 , AlBr 3 , AlF 3 , BF 3 , OEt 2 , BCl 3 , BBr 3 , GaCl 3 , GaBr 3 , InCl 3 , InBr 3 , and so on.
  • Examples of the blended acid used in the above schemes (12) to (16) include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, and (trifluoromethanesulfonyl) imide. , Tris (trifluoromethanesulfonyl) methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride and the like.
  • Examples of solid Bronsted acids include Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and TAYCA Cure (trade name: TAYCA Corporation).
  • Examples of the amines that may be added in the above schemes (12) to (16) include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo [2.2.2] octane, N, N-dimethyl-p-toluidine, and the like. Examples thereof include N, N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.
  • the solvents used in the above schemes (12) to (16) 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.
  • Rinsurufido compound Y 1 is able to obtain the compound is a phosphorus oxide by treatment with at m- chloroperbenzoic acid (m-CPBA), Y 1 by treatment with triethyl phosphine phosphorus A compound that is an atom can be obtained.
  • m-CPBA m- chloroperbenzoic acid
  • halogens such as bromine atoms and chlorine atoms are located at the positions where lithium is to be introduced as in the above schemes (6) and (7). Lithium can also be introduced at the desired position by halogen-metal exchange (schedules (20), (21) and (22) below).
  • the multimers in the case where Y 1 is phosphor sulfide and X 1 and X 2 are oxygen atoms thus formed are also m-chloroperbenzoic acid (m-chloroperbenzoic acid (19) as in the above schemes (18) and (19).
  • Treatment with m-CPBA) can give a compound in which Y 1 is a phosphorus oxide
  • treatment with triethylphosphine can give a compound in which Y 1 is a phosphorus atom.
  • Y 1 can be changed to Compounds that are Al, Ga, As, Si-R or Ge-R, and compounds in which X 1 and X 2 are S can also be synthesized.
  • solvent used in the above reaction are t-butylbenzene, xylene and the like.
  • a ring, b aryl or heteroaryl ring adjacent groups is a ring attached, with b ring or c ring of the rings and c ring substituents R 1 ⁇ R 11 At least one hydrogen in the formed ring may be substituted with aryl or heteroaryl. Therefore, the polycyclic aromatic compound represented by the formula (2) has the formulas (2-1) of the following schemes (23) and (24) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring. ) And the formula (2-2), the ring structure constituting the compound changes. These compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (19) to the intermediates shown in the following schemes (23) and (24).
  • Equation (2-1) and ring A ', B' in the formula (2-2) ring and C 'ring, and adjacent groups are bonded of the substituents R 1 ⁇ R 11, respectively a ring ,
  • An aryl ring or a heteroaryl ring formed together with the b ring and the c ring (it can also be said to be a fused ring formed by condensing another ring structure on the a ring, the b ring or the c ring).
  • R in at least one of "the above>N-R,> Si (-R) 2 and> C (-R) 2 in the formula (2) is -O-, -S-, -C (-R). ) 2 -or is bonded to at least one ring of the a ring, b ring and c ring by a single bond "is expressed by the formula (2-3-1) of the following scheme (25).
  • a multimeric compound is synthesized by using an orthometalation reagent such as butyllithium in a molar amount twice or three times the molar amount of intermediate 1. can do. Further, a halogen such as a bromine atom or a chlorine atom is introduced in advance at a position where a metal such as lithium is to be introduced, and the metal can be introduced at a desired position by exchanging the halogen-metal.
  • an orthometalation reagent such as butyllithium in a molar amount twice or three times the molar amount of intermediate 1.
  • a halogen such as a bromine atom or a chlorine atom is introduced in advance at a position where a metal such as lithium is to be introduced, and the metal can be introduced at a desired position by exchanging the halogen-metal.
  • a desired position can be obtained by using a raw material condensed with cycloalkane or adding a step of condensing cycloalkane somewhere in the reaction step in each scheme. Can produce cycloalkane-condensed compounds.
  • a cycloalkane-condensed intermediate is synthesized and the desired position is formed by cyclizing the intermediate as in the following scheme (28).
  • X represents halogen or hydrogen, and the definitions of other codes are the same as the definitions of codes in formula (2).
  • the pre-cyclization intermediate in scheme (28) also has a desired substituent by appropriately combining a Buchwald-Hartwig reaction, a Suzuki coupling reaction, an etherification reaction by a nucleophilic substitution reaction, an Ullmann reaction, or the like. Intermediates can be synthesized. In these reactions, commercially available products can also be used as the raw material to be the precursor of cycloalkane condensation.
  • the compound of formula (2-A) having a cycloalkane-condensed diphenylamino can also be synthesized by, for example, the following method. That is, when diphenylamino which is cycloalkane-condensed bromobenzene and trihalogenated aniline is introduced by an amination reaction such as Buchwald-Hartwig reaction, and then X 1 and X 2 are N-R. Is induced to the intermediate (M-3) by etheration with phenol when X 1 and X 2 are O in an amination reaction such as Buchwald-Hartwig reaction, and then, for example, butyl lithium.
  • Tandem Bora Friedelcrafts by acting a metallizing reagent such as, transmetallating, then a boron halide such as boron tribromide, and then a blended base such as diethylisopropylamine.
  • a metallizing reagent such as, transmetallating
  • a boron halide such as boron tribromide
  • a blended base such as diethylisopropylamine
  • the orthometallation reagents used in the above scheme include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium and t-butyllithium, lithium diisopropylamide, lithium tetramethylpiperidide and lithium hexamethyl.
  • alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium and t-butyllithium, lithium diisopropylamide, lithium tetramethylpiperidide and lithium hexamethyl.
  • organic alkali compounds such as disilamide and potassium hexamethyldisilazide
  • dispersed alkali metals such as organic solvent-dispersed Na.
  • the three fluoride Y 1, trichloride of Y 1, halogen Y 1 such tribromide, triiodide of Y 1 of Y 1 examples thereof include isomers, Y 1 amination halides such as CIPN (NET 2 ) 2 , Y 1 alkoxides, and Y 1 aryl bromides.
  • the blended bases used in the above scheme include N, N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N, N-Dimethylaniline, N, N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar 4 BNa, Ar 4 BK, Ar 3 B, Examples thereof include Ar 4 Si (where Ar is an aryl such as phenyl).
  • Lewis acids used in the above scheme 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 , SnCl.
  • Bronsted bases or Lewis acids may be used to facilitate the tandem hetero-Friedel-Crafts reaction.
  • Y 1 halides such as Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, and Y 1 triiodide are used, as the aromatic electrophobic substitution reaction progresses, Since acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, it is effective to use a blended base that captures the acid.
  • the polycyclic aromatic compound of the present invention and its multimer include a compound in which at least a part of hydrogen atoms are substituted with deuterium or cyano, or a compound in which at least a part of hydrogen atoms is substituted with halogen such as fluorine or chlorine.
  • a compound or the like can be synthesized in the same manner as described above by using a raw material in which the desired position is dehydrogenated, cyanated, fluorinated or chlorinated.
  • the amino-substituted polycyclic aromatic compounds according to the present invention can be used as materials for organic devices.
  • the organic device include an organic electroluminescent device, an organic field effect transistor, and an organic thin film solar cell.
  • FIG. 1 is a schematic cross-sectional view showing an organic EL device according to the present embodiment.
  • the organic EL element 100 shown in FIG. 1 is placed on a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103.
  • the hole transport layer 104 is provided, the light emitting layer 105 is provided on the hole transport layer 104, the electron transport layer 106 is provided on the light emitting layer 105, and the electron transport layer 106 is provided. It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.
  • the organic EL element 100 is manufactured in the 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.
  • the electron transport layer 106 provided on the electron transport layer 106
  • the light emitting layer 105 provided on the electron transport layer 106
  • the hole transport layer 104 provided on the light emitting layer 105
  • the hole transport layer 104 provided on the hole transport layer 104.
  • the hole injection layer 103 provided in the hole injection layer 103 and the anode 102 provided on the hole injection layer 103 may be provided.
  • 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.
  • the layer 107 is an arbitrarily provided layer. Further, each of the above layers may be composed of a single layer or a plurality of layers.
  • the substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used.
  • 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.
  • a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable.
  • soda lime glass, non-alkali glass, or the like is used, and the thickness may be sufficient to maintain the mechanical strength.
  • the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side, and a synthetic resin plate, film or sheet having a particularly low gas barrier property may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.
  • the anode 102 serves to inject holes into the light emitting layer 105.
  • the hole injection layer 103 and / or the hole 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. ..
  • Examples of the material forming the anode 102 include inorganic compounds and organic compounds.
  • Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxidation, etc.). (IZO, etc.), metals halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass, nesa glass, etc.
  • Examples of the organic compound include polythiophene such as poly (3-methylthiophene) and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from the substances used as the anode of the organic EL element.
  • the resistance of the transparent electrode is not limited as long as a sufficient current can be supplied to emit light from the light emitting element, but it is desirable that the resistance is low from the viewpoint of power consumption of the light emitting element.
  • an ITO substrate of 300 ⁇ / ⁇ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10 ⁇ / ⁇ , for example, 100 to 5 ⁇ / ⁇ , preferably 50 to 5 ⁇ . It is especially desirable to use a low resistance product of / ⁇ .
  • the thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm.
  • the hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport 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 via the hole injection layer 103 to the light emitting layer 105.
  • the hole injection layer 103 and the hole transport layer 104 are formed by laminating and mixing one or more of the hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder, respectively. Will be done. Further, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.
  • the substance As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and the hole injection efficiency is high, and the injected holes are efficiently transported. Is desirable. For that purpose, it is preferable that the substance has a small ionization potential, a large hole mobility, excellent stability, and is less likely to generate trap impurities during production and use.
  • a compound conventionally used as a hole charge transport material, a p-type semiconductor, and a hole injection layer of an organic EL element can be selected and used from the known compounds used in the hole transport layer.
  • Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), and triarylamine derivatives (aromatic tertiary).
  • polycarbonate or styrene derivative having the monomer in the side chain, polyvinylcarbazole, polysilane, etc. are preferable, but a thin film necessary for producing a light emitting element can be formed, holes can be injected from the anode, and holes can be further injected. There is no particular limitation as long as it is a compound capable of transporting.
  • the organic semiconductor matrix substance is composed of a compound having a good electron donating property or a compound having a good electron accepting property.
  • Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping electron donors.
  • TCNQ tetracyanoquinone dimethane
  • F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane
  • J J.
  • the above-mentioned materials for the hole injection layer and the material for the hole transport layer are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a polymer crosslinked product thereof.
  • a pendant type polymer compound obtained by reacting a main chain type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for a hole layer.
  • the reactive substituent in this case the description of the polycyclic aromatic compound represented by the formula (1) can be cited. Details of the uses of such polymer compounds and crosslinked polymers will be described later.
  • 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 the electrodes to which an electric field is applied.
  • the material for forming the light emitting layer 105 may be a compound (light emitting compound) that is excited by recombination of holes and electrons to emit light, and can form a stable thin film shape and is in a solid state. It is preferable that the compound exhibits a strong emission (fluorescence) efficiency.
  • a host material and, for example, a polycyclic aromatic compound represented by the formula (1) as a dopant material can be used as the material for the light emitting layer.
  • the light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting layer material (host material, dopant material).
  • the host material and the dopant material may be one kind or a combination of two or more.
  • the dopant material may be included entirely, partially, 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 at the same time.
  • the amount of host material used differs depending on the type of host material, and may be determined according to the characteristics of the host material.
  • the guideline for the amount of the host material used is preferably 50 to 99.99% by mass, more preferably 80 to 99.95% by mass, and further preferably 90 to 99.9% by mass of the entire material for the light emitting layer. Is.
  • the amount of the dopant material used differs depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material.
  • the 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 further preferably 0.1 to 10% by mass of the entire light emitting layer material. is there.
  • the above range is preferable in that, for example, the density quenching phenomenon can be prevented. From the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.
  • Host materials include fused ring derivatives such as anthracene, pyrene, dibenzoglycene or fluorene, which have long been known as luminescent materials, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. , Examples of compounds represented by any of the following formulas (H1), (H2) and (H3).
  • Anthracene compounds, fluorene compounds or dibenzochrysene compounds, compounds represented by any of the following formulas (H1), (H2) and (H3) are preferable, and anthracene compounds or formulas (H1) and (H2) below And the compound represented by any of (H3) is more preferable.
  • a part or all of the hydrogen atoms of the host material are deuterated.
  • a host compound in which some or all deuterated hydrogen atoms are deuterated and a dopant compound in which some or all deuterated hydrogen atoms are deuterated are combined to form a light emitting layer. It is also preferable to do so.
  • L 1 is an arylene having 6 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms, heteroarylene arylene and 6 to 24 carbon atoms having 6 to 24 carbon atoms
  • the arylene is a heteroarylene arylene, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms, specifically, a benzene ring or a biphenyl ring.
  • Divalent groups such as terphenyl ring and fluorene ring.
  • heteroarylene a heteroarylene having 2 to 24 carbon atoms is preferable, a heteroarylene having 2 to 20 carbon atoms is more preferable, a heteroarylene having 2 to 15 carbon atoms is further preferable, and a heteroarylene having 2 to 10 carbon atoms is particularly preferable.
  • a preferable specific example is a compound represented by any of the structural formulas listed below.
  • Me is methyl.
  • at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (for example, methyl or t-butyl), phenyl or naphthyl.
  • the anthracene-based compound as a host is, for example, a compound represented by the following formula (3-H) or the following formula (3-2-H).
  • X and Ar 4 are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, respectively.
  • Aryl heteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, alkoxy which may be substituted, which may be substituted.
  • Aryloxy, optionally substituted arylthio or optionally substituted silyl, all X and Ar 4 are not hydrogenated at the same time.
  • At least one hydrogen in the compound represented by the formula (3-H) may be substituted with a halogen, cyano, deuterium or a heteroaryl which may be substituted.
  • a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3-H) as a unit structure.
  • the unit structures represented by the formula (3-H) may be bonded to each other via X, and the X includes a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.) and a heteroarylene (pyridine).
  • a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc. have a divalent bond value
  • aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl will be described in the section of preferred embodiments below.
  • substituents thereof include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl, and these. Details will also be described in the section of preferred embodiments below.
  • X is a group independently represented by the formula (3-X1), the formula (3-X2) or the formula (3-X3), and the formula (3-X1) and the formula (3-X1).
  • the group represented by (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3-H) in *.
  • the two Xs do not simultaneously become groups represented by the formula (3-X3). More preferably, the two Xs do not simultaneously become a group represented by the formula (3-X2).
  • a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3-H) as a unit structure.
  • the unit structures represented by the formula (3-H) may be bonded to each other via X, and the X includes a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.) and a heteroarylene (pyridine).
  • a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc. have a divalent bond value
  • the naphthalene moiety in the formulas (3-X1) and (3-X2) may be condensed with one benzene ring.
  • the structure condensed in this way is as follows.
  • Ar 1 and Ar 2 are independently represented by hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or formula (A). Groups to be (including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl). When Ar 1 or Ar 2 is a group represented by the formula (A) described later, the group represented by the formula (A) is represented by the formula (3-X1) or the formula (3-X2) in the *. It binds to the naphthalene ring inside.
  • Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the formula (A) (carbazolyl, benzocarbazolyl). And phenyl-substituted carbazolyl).
  • Ar 3 is a group represented by the formula (A)
  • the group represented by the formula (A) is bonded to the single bond represented by the straight line in the formula (3-X3) in the *. .. That is, the anthracene ring of the formula (3-H) and the group represented by the formula (A) are directly bonded.
  • Ar 3 may have a substituent, and at least one hydrogen in Ar 3 is further an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl and phenanthryl. , Fluolenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the formula (A) (including carbazolyl and phenyl-substituted carbazolyl) may be substituted.
  • the substituent contained in Ar 3 is a group represented by the formula (A)
  • the group represented by the formula (A) is bonded to Ar 3 in the formula (3-X3) in the *.
  • Ar 4 is 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. Cyril has been.
  • alkyl having 1 to 4 carbon atoms to be substituted with silyl examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and the three hydrogens in silyl are independent of each other. , Substituted with these alkyls.
  • sil substituted with alkyl having 1 to 4 carbon atoms includes trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyl.
  • Cycloalkyls having 5 to 10 carbon atoms to be substituted with silyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, Bicyclo [1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, decahydronaphthalenyl, decahydro Azulenyl and the like are mentioned, and each of the three hydrogens in silyl is independently substituted with these cycloalkyls.
  • silyl substituted with cycloalkyl having 5 to 10 carbon atoms include tricyclopentyl silyl and tricyclohexyl silyl.
  • Substituted silyls include dialkylcycloalkylsilyls substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyls, which are substituted alkyls and cycloalkyls.
  • dialkylcycloalkylsilyls substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyls, which are substituted alkyls and cycloalkyls.
  • alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyls which are substituted alkyls and cycloalkyls.
  • hydrogen in the chemical structure of the anthracene compound represented by the formula (3-H) may be substituted with the group represented by the formula (A).
  • the group represented by the formula (A) is substituted with at least one hydrogen in the compound represented by the formula (3-H) in the *.

Abstract

La présente invention concerne un composé aromatique polycyclique représenté par la formule (1), ou un polymère de celui-ci. Le composé selon la présente invention peut être utilisé dans un dispositif organique tel qu'un élément électroluminescent organique. (Dans la formule (1), les cycles A, B et C sont des cycles aryle éventuellement substitués ou des cycles hétéroaryle, au moins un cycle choisi dans le groupe constitué par le cycle A, le cycle B et le cycle C est un cycle condensé formé à partir de deux cycles ou plus choisis dans le groupe constitué par un cycle aryle, un cycle hétéroaryle et un cycle cyclopentadiène, Y1 est B ou similaire, X1 et X2 sont >N-R (R étant un aryle ou similaire), les cycles A, B, C, etc. peuvent être condensés par un cycloalcane ou analogue, et l'hydrogène dans la formule (1) peut être substitué par du deutérium, cyano ou halogène.)
PCT/JP2020/023312 2019-06-14 2020-06-12 Composé aromatique polycyclique WO2020251049A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020227000819A KR20220024468A (ko) 2019-06-14 2020-06-12 다환방향족 화합물
JP2021526175A JPWO2020251049A1 (fr) 2019-06-14 2020-06-12
CN202080043697.4A CN114026147A (zh) 2019-06-14 2020-06-12 多环芳香族化合物

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
JP2019111587 2019-06-14
JP2019-111587 2019-06-14
JP2019142577 2019-08-01
JP2019-142577 2019-08-01
JP2019-189741 2019-10-16
JP2019189741 2019-10-16
JP2019219152 2019-12-03
JP2019-219152 2019-12-03
JP2020-043590 2020-03-13
JP2020043590 2020-03-13

Publications (1)

Publication Number Publication Date
WO2020251049A1 true WO2020251049A1 (fr) 2020-12-17

Family

ID=73781246

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/023312 WO2020251049A1 (fr) 2019-06-14 2020-06-12 Composé aromatique polycyclique

Country Status (5)

Country Link
JP (1) JPWO2020251049A1 (fr)
KR (1) KR20220024468A (fr)
CN (1) CN114026147A (fr)
TW (1) TW202104239A (fr)
WO (1) WO2020251049A1 (fr)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112961174A (zh) * 2021-02-05 2021-06-15 吉林奥来德光电材料股份有限公司 一种多环芳族化合物及其制备方法和应用
WO2021122740A1 (fr) * 2019-12-19 2021-06-24 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
CN113024587A (zh) * 2021-03-12 2021-06-25 吉林奥来德光电材料股份有限公司 含硼和氮的稠合芳香族衍生物及其的制备方法和有机电致发光器件
CN113087734A (zh) * 2021-04-14 2021-07-09 吉林奥来德光电材料股份有限公司 一种有机化合物掺杂材料及其制备方法和应用
CN113135935A (zh) * 2021-04-14 2021-07-20 吉林奥来德光电材料股份有限公司 一种多环芳族系化合物及其制备方法和应用
WO2021177022A1 (fr) * 2020-03-03 2021-09-10 保土谷化学工業株式会社 Élément électroluminescent organique
CN114685545A (zh) * 2020-12-29 2022-07-01 乐金显示有限公司 发光化合物和包含其的有机发光装置
WO2022145775A1 (fr) * 2021-01-04 2022-07-07 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
CN114957223A (zh) * 2021-05-19 2022-08-30 江苏精润鸿测控技术有限公司 新型有机化合物和包含此化合物的有机电致发光器件
EP4056577A1 (fr) * 2021-03-12 2022-09-14 SFC Co., Ltd. Composé polycyclique et dispositif électroluminescent organique l'utilisant
KR20220128255A (ko) * 2021-03-12 2022-09-20 에스에프씨 주식회사 다환 고리 화합물 및 이를 이용한 유기발광소자
WO2022196612A1 (fr) * 2021-03-15 2022-09-22 学校法人関西学院 Composé aromatique polycyclique
JP2022140426A (ja) * 2021-03-12 2022-09-26 エスエフシー カンパニー リミテッド 多環化合物及びこれを用いた有機発光素子
WO2022203403A1 (fr) * 2021-03-24 2022-09-29 경상국립대학교산학협력단 Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2022220453A1 (fr) * 2021-04-15 2022-10-20 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
KR20220142937A (ko) 2021-04-15 2022-10-24 가꼬우 호징 관세이 가쿠잉 다환방향족 화합물
KR20220148952A (ko) 2021-04-26 2022-11-07 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
WO2022255634A1 (fr) * 2021-06-02 2022-12-08 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
KR20230024215A (ko) 2021-08-11 2023-02-20 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
KR20230034895A (ko) 2021-09-03 2023-03-10 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
WO2023043299A1 (fr) * 2021-09-20 2023-03-23 Samsung Display Co., Ltd. Molécules organiques pour dispositifs optoélectroniques
KR20230043732A (ko) 2021-09-24 2023-03-31 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
TWI817168B (zh) * 2020-12-29 2023-10-01 南韓商Ｌｇ顯示器股份有限公司 發光化合物及包含該發光化合物的有機發光裝置
KR20230140484A (ko) 2022-03-22 2023-10-06 가꼬우 호징 관세이 가쿠잉 다환방향족 화합물

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210067845A (ko) * 2019-11-29 2021-06-08 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN113201003A (zh) * 2021-05-08 2021-08-03 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其应用

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015102118A1 (fr) * 2014-02-18 2015-07-09 学校法人関西学院 Composé aromatique polycyclique
WO2016152544A1 (fr) * 2015-03-24 2016-09-29 学校法人関西学院 Élément électroluminescent organique
WO2017188111A1 (fr) * 2016-04-26 2017-11-02 学校法人関西学院 Élément électroluminescent organique
JP2018043984A (ja) * 2016-09-07 2018-03-22 学校法人関西学院 多環芳香族化合物
KR20180120619A (ko) * 2017-04-27 2018-11-06 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2018203666A1 (fr) * 2017-05-02 2018-11-08 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2019088799A1 (fr) * 2017-11-06 2019-05-09 주식회사 엘지화학 Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2020111830A1 (fr) * 2018-11-30 2020-06-04 에스에프씨 주식회사 Élément électroluminescent organique utilisant un composé dérivé aromatique polycyclique

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3735703B2 (ja) 1999-12-21 2006-01-18 大阪大学長 エレクトロルミネッセンス素子
US20040131881A1 (en) 2002-12-31 2004-07-08 Eastman Kodak Company Complex fluorene-containing compounds for use in OLED devices
JP2005170911A (ja) 2003-12-15 2005-06-30 Idemitsu Kosan Co Ltd 芳香族化合物およびそれを用いた有機エレクトロルミネッセンス素子
DE102010009903A1 (de) 2010-03-02 2011-09-08 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
US20140058099A1 (en) 2011-03-03 2014-02-27 Kyushu University National University Corporation Novel compound, charge transport material, and organic device
WO2012133465A1 (fr) * 2011-03-28 2012-10-04 住友化学株式会社 Dispositif électronique, composé polymère, composé organique et procédé de production du composé polymère
KR102123784B1 (ko) * 2012-04-09 2020-06-17 미쯔비시 케미컬 주식회사 유기 전계 발광 소자용 조성물 및 유기 전계 발광 소자
KR101876763B1 (ko) * 2017-05-22 2018-07-11 머티어리얼사이언스 주식회사 유기화합물 및 이를 포함하는 유기전계발광소자

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015102118A1 (fr) * 2014-02-18 2015-07-09 学校法人関西学院 Composé aromatique polycyclique
WO2016152544A1 (fr) * 2015-03-24 2016-09-29 学校法人関西学院 Élément électroluminescent organique
WO2017188111A1 (fr) * 2016-04-26 2017-11-02 学校法人関西学院 Élément électroluminescent organique
JP2018043984A (ja) * 2016-09-07 2018-03-22 学校法人関西学院 多環芳香族化合物
KR20180120619A (ko) * 2017-04-27 2018-11-06 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2018203666A1 (fr) * 2017-05-02 2018-11-08 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2019088799A1 (fr) * 2017-11-06 2019-05-09 주식회사 엘지화학 Composé polycyclique et dispositif électroluminescent organique le comprenant
WO2020111830A1 (fr) * 2018-11-30 2020-06-04 에스에프씨 주식회사 Élément électroluminescent organique utilisant un composé dérivé aromatique polycyclique

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021122740A1 (fr) * 2019-12-19 2021-06-24 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
WO2021177022A1 (fr) * 2020-03-03 2021-09-10 保土谷化学工業株式会社 Élément électroluminescent organique
EP4023653A1 (fr) * 2020-12-29 2022-07-06 LG Display Co., Ltd. Composé électroluminescent et dispositif électroluminescent organique le comprenant
TWI817168B (zh) * 2020-12-29 2023-10-01 南韓商Ｌｇ顯示器股份有限公司 發光化合物及包含該發光化合物的有機發光裝置
CN114685545A (zh) * 2020-12-29 2022-07-01 乐金显示有限公司 发光化合物和包含其的有机发光装置
WO2022145775A1 (fr) * 2021-01-04 2022-07-07 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
CN112961174A (zh) * 2021-02-05 2021-06-15 吉林奥来德光电材料股份有限公司 一种多环芳族化合物及其制备方法和应用
JP2022140425A (ja) * 2021-03-12 2022-09-26 エスエフシー カンパニー リミテッド 多環化合物及びこれを用いた有機発光素子
CN113024587A (zh) * 2021-03-12 2021-06-25 吉林奥来德光电材料股份有限公司 含硼和氮的稠合芳香族衍生物及其的制备方法和有机电致发光器件
JP7407853B2 (ja) 2021-03-12 2024-01-04 エスエフシー カンパニー リミテッド 多環化合物及びこれを用いた有機発光素子
EP4056577A1 (fr) * 2021-03-12 2022-09-14 SFC Co., Ltd. Composé polycyclique et dispositif électroluminescent organique l'utilisant
KR20220128255A (ko) * 2021-03-12 2022-09-20 에스에프씨 주식회사 다환 고리 화합물 및 이를 이용한 유기발광소자
JP2022140426A (ja) * 2021-03-12 2022-09-26 エスエフシー カンパニー リミテッド 多環化合物及びこれを用いた有機発光素子
KR102453929B1 (ko) * 2021-03-12 2022-10-12 에스에프씨 주식회사 다환 고리 화합물 및 이를 이용한 유기발광소자
JP7407852B2 (ja) 2021-03-12 2024-01-04 エスエフシー カンパニー リミテッド 多環化合物及びこれを用いた有機発光素子
WO2022196612A1 (fr) * 2021-03-15 2022-09-22 学校法人関西学院 Composé aromatique polycyclique
KR20230156725A (ko) 2021-03-15 2023-11-14 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
WO2022203403A1 (fr) * 2021-03-24 2022-09-29 경상국립대학교산학협력단 Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant
CN113087734A (zh) * 2021-04-14 2021-07-09 吉林奥来德光电材料股份有限公司 一种有机化合物掺杂材料及其制备方法和应用
CN113135935A (zh) * 2021-04-14 2021-07-20 吉林奥来德光电材料股份有限公司 一种多环芳族系化合物及其制备方法和应用
KR20220142937A (ko) 2021-04-15 2022-10-24 가꼬우 호징 관세이 가쿠잉 다환방향족 화합물
WO2022220453A1 (fr) * 2021-04-15 2022-10-20 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
KR20220148952A (ko) 2021-04-26 2022-11-07 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
CN114957223A (zh) * 2021-05-19 2022-08-30 江苏精润鸿测控技术有限公司 新型有机化合物和包含此化合物的有机电致发光器件
WO2022255634A1 (fr) * 2021-06-02 2022-12-08 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique l'utilisant
KR20230024215A (ko) 2021-08-11 2023-02-20 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
KR20230034895A (ko) 2021-09-03 2023-03-10 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
WO2023043299A1 (fr) * 2021-09-20 2023-03-23 Samsung Display Co., Ltd. Molécules organiques pour dispositifs optoélectroniques
KR20230043732A (ko) 2021-09-24 2023-03-31 가꼬우 호징 관세이 가쿠잉 다환 방향족 화합물
KR20230140484A (ko) 2022-03-22 2023-10-06 가꼬우 호징 관세이 가쿠잉 다환방향족 화합물

Also Published As

Publication number Publication date
TW202104239A (zh) 2021-02-01
KR20220024468A (ko) 2022-03-03
JPWO2020251049A1 (fr) 2020-12-17
CN114026147A (zh) 2022-02-08

Similar Documents

Publication Publication Date Title
WO2020251049A1 (fr) Composé aromatique polycyclique
WO2020218079A1 (fr) Composé aromatique polycyclique condensé par un cycloalcane
WO2019198699A1 (fr) Composé aromatique polycyclique substitué par cycloalkyle
JP7445923B2 (ja) ターシャリーアルキル置換多環芳香族化合物
WO2020162600A1 (fr) Composé aromatique polycyclique
JP6738063B2 (ja) シクロアルキル置換多環芳香族化合物
JP2021014446A (ja) アミノ置換多環芳香族化合物
JP2021038206A (ja) 多環芳香族化合物
WO2020250700A1 (fr) Composé aromatique polycyclique
WO2021230133A1 (fr) Composé aromatique polycyclique
JP2022074041A (ja) 多環芳香族化合物
JP2021113188A (ja) 多環芳香族化合物
JP2021095342A (ja) 多環芳香族化合物
JP2021063074A (ja) シアノ置換多環芳香族化合物
JP2021086978A (ja) 有機電界発光素子
JP2021113160A (ja) 多環芳香族化合物
JP2022017207A (ja) 多環芳香族化合物
KR20220124097A (ko) 다환 방향족 화합물
JP2022179317A (ja) 多環芳香族化合物
JP2022082867A (ja) 多環芳香族化合物
JP2022133567A (ja) 多環芳香族化合物
JP2022032441A (ja) 多環芳香族化合物
JP2023085205A (ja) トリアジニル基を有する多環芳香族化合物を用いた有機電界発光素子
KR20230098036A (ko) 다환 방향족 화합물
JP2023177281A (ja) 多環芳香族化合物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20822847

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021526175

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20227000819

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 20822847

Country of ref document: EP

Kind code of ref document: A1