WO2019151204A1 - Élément électroluminescent à effet de champ organique utilisant un matériau électroluminescent de composé aromatique polycyclique - Google Patents

Élément électroluminescent à effet de champ organique utilisant un matériau électroluminescent de composé aromatique polycyclique Download PDF

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WO2019151204A1
WO2019151204A1 PCT/JP2019/002866 JP2019002866W WO2019151204A1 WO 2019151204 A1 WO2019151204 A1 WO 2019151204A1 JP 2019002866 W JP2019002866 W JP 2019002866W WO 2019151204 A1 WO2019151204 A1 WO 2019151204A1
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ring
aryl
carbon atoms
alkyl
heteroaryl
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PCT/JP2019/002866
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Japanese (ja)
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琢次 畠山
靖宏 近藤
笹田　康幸
静萍 倪
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学校法人関西学院
Jnc株式会社
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    • 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
    • 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]
    • H10K50/14—Carrier transporting layers

Definitions

  • the present invention relates to an organic electroluminescent element using a light emitting material of a polycyclic aromatic compound and a multimer thereof (hereinafter, both are also simply referred to as a polycyclic aromatic compound), a display device, and a lighting device.
  • organic electroluminescent elements made of organic materials (hereinafter also referred to as organic EL elements) are It has been actively studied because it is easy to reduce the weight and size.
  • organic materials with emission characteristics such as blue, which is one of the three primary colors of light
  • organic materials with charge transporting ability potential of becoming semiconductors and superconductors
  • development has been actively researched regardless of whether it is a high molecular compound or a low molecular compound.
  • 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 including an organic compound disposed between the pair of electrodes.
  • the layer containing an organic compound include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons.
  • Various organic materials suitable for these layers have been developed.
  • a benzofluorene compound has been developed (International Publication No. 2004/061047).
  • a hole transport material for example, a triphenylamine compound has been developed (Japanese Patent Laid-Open No. 2001-172232).
  • an anthracene compound has been developed (Japanese Patent Laid-Open No. 2005-170911).
  • the charge transport property of a NO-linked compound (Compound 1 on page 63) is evaluated, but a method for producing a material other than the NO-linked compound is not described, and the element to be linked is not described. Since the electronic state of the entire compound is different if it is different, the characteristics obtained from materials other than NO-linked compounds are not yet known. Other examples of such compounds can be found (WO 2011/107186). For example, a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence having a shorter wavelength, and thus is useful as a blue light-emitting layer material.
  • T1 triplet exciton energy
  • 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 connected by a single bond, phosphorus atom or silicon atom. This is because a large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material is secured by connecting a large number of relatively conjugated aromatic rings. Furthermore, a host material for an organic EL device using a phosphorescent material or a thermally activated delayed fluorescent material also requires high triplet excitation energy (E T ), but the molecule has a donor or acceptor aromatic ring or substitution.
  • E T triplet excitation energy
  • the present inventors have used a compound having a specific structure among polycyclic aromatic compounds in which a plurality of aromatic rings are connected with a boron atom or the like and an oxygen atom, The inventors have found that an excellent organic EL device can be obtained, and completed the present invention. That is, the present invention provides an organic EL device using a polycyclic aromatic compound having aryloxy or heteroaryloxy as a substituent.
  • the chemical structure or substituent may be represented by the number of carbons.
  • the number of carbons in the case where a substituent is substituted on the chemical structure or the substituent is further substituted on the chemical group is the chemical structure.
  • the number of carbon atoms of each substituent and does not mean the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituent and the substituent.
  • “substituent B of carbon number Y substituted by substituent A of carbon number X” means that “substituent B of carbon number Y” is substituted for “substituent B of carbon number Y”.
  • the carbon number Y is not the total carbon number of the substituent A and the substituent B.
  • substituted with substituent A means that “substituent A having no carbon number” is substituted for “substituent B having carbon number Y”.
  • the carbon number Y is not the total carbon number of the substituent A and the substituent B.
  • An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer disposed between the pair of electrodes, the light emitting layer comprising: As the first component, at least one of a polycyclic aromatic compound represented by the following general formula (A) and a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (A); An organic electroluminescence device comprising, as a second component, at least one compound having a triplet energy (E T ) of 2.2 to 3.0 eV.
  • E T triplet energy
  • R 1 to R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, wherein at least one hydrogen is further aryl, Optionally substituted with heteroaryl, diarylamino, alkyl or cycloalkyl, Adjacent groups of R 1 to R 11 may be bonded to form an aryl ring or a heteroaryl ring together with a ring, b ring or c ring, and at least one hydrogen in the formed ring is Optionally substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, wherein at least one hydrogen is further aryl, heteroaryl, diarylamino, alkyl or cycloalkyl May be replaced with Provide
  • R 1 to R 11 are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), 1 to carbon atoms 12 alkyl or cycloalkyl having 3 to 16 carbon atoms, in which at least one hydrogen is further aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, or diarylamino (wherein aryl has 6 to 6 carbon atoms) 12 aryl), alkyl having 1 to 12 carbons or cycloalkyl having 3 to 16 carbons, Adjacent groups of R 1 to R 11 may be bonded to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring or c ring.
  • At least one hydrogen in the ring formed is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), 1 to 12 carbon atoms May be substituted with alkyl or cycloalkyl having 3 to 16 carbon atoms, in which at least one hydrogen is further aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, or diarylamino (where aryl is carbon)
  • An aryl having 6 to 12 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms Provided that one, two or three of R 2 , R 5 , R 7 , R 8 and R 10 are groups represented by —O—W, and each W is independently a group having 6 to 30 carbon atoms.
  • At least one hydrogen is aryl having 6 to 30 carbons, heteroaryl having 2 to 30 carbons, or diarylamino (wherein aryl has 6 to 12 carbons) Aryl), optionally substituted with alkyl having 1 to 12 carbons or cycloalkyl having 3 to 16 carbons, Item 2.
  • R 1 to R 11 are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), 1 to carbon atoms 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen is further aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or diarylamino (wherein aryl has 6 to 6 carbon atoms) 10 aryl), optionally substituted with C 1-6 alkyl or C 3-14 cycloalkyl, Adjacent groups of R 1 to R 11 may be bonded to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a ring, b ring or c ring.
  • At least one hydrogen in the formed ring is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), 1 to 6 carbon atoms May be substituted with alkyl or cycloalkyl having 3 to 14 carbon atoms, in which at least one hydrogen is further aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or diarylamino (where aryl is carbon)
  • An aryl having 6 to 10 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms Provided that one, two or three of R 2 , R 5 , R 7 , R 8 and R 10 are groups represented by —O—W, and each W independently represents 6 to 16 carbon atoms.
  • At least one hydrogen is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or diarylamino (wherein aryl has 6 to 10 carbon atoms) Aryl), optionally substituted with alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, Item 2.
  • R 2 or R 5 is —O—W
  • R 2 and R 5 are —O—W
  • R 5 and R 10 are —O—W
  • each W is independently aryl having 6 to 16 carbon atoms or heteroaryl having 2 to 15 carbon atoms, and at least one hydrogen in these is aryl having 6 to 12 carbon atoms
  • a heteroaryl having 2 to 10 carbon atoms a diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms) optionally substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, Item 4.
  • the organic electroluminescent device according to any one of Items 1 to 3.
  • R 2 or R 5 is —O—W
  • R 2 and R 5 are —O—W
  • R 5 and R 10 are —O—W
  • each W is independently phenyl, biphenylyl, terphenylyl or naphthyl, and at least one hydrogen in these is alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons Optionally substituted with Item 4.
  • the organic electroluminescent device according to any one of Items 1 to 3.
  • Item 6 The organic electroluminescent device according to Item 1, wherein the first component is a compound represented by any one of the following general formulas. In each of the above formulas, any hydrogen may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.
  • Item 7 The organic electroluminescent device according to Item 1, wherein the first component is a compound represented by any one of the following general formulas. “Me” in the above structural formulas represents a methyl group.
  • the second component is a compound represented by the following general formula (B1), a compound represented by the general formula (B2), a polycyclic aromatic compound represented by the general formula (B3), and a general formula (B3).
  • Item 8. The organic electroluminescence device according to any one of Items 1 to 7, which is at least one selected from the group consisting of multimers of polycyclic aromatic compounds having a plurality of the structures described above.
  • M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu
  • n is an integer of 1 to 3
  • X and Y are each independently 2 It is a monoanionic ligand of the locus.
  • ED is an electron donating group
  • Ln is a bonding group
  • EA is an electron accepting group
  • the energy difference ( ⁇ S 1 T 1 ) is 0.2 eV or less.
  • a ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted; Rings B and C may be connected by> N—R or> O, and R in> N—R may be an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted An optionally substituted alkyl or an optionally substituted cycloalkyl, and the R may be bonded to the B ring and / or the C ring by a linking group or a single bond,
  • Each X is independently>N—R,>O,> C (—R) 2 ,> S or> Si (—R) 2 ;
  • R in the>N—R,> C (—R) 2 or> Si (—R) 2 is each independently an optionally substituted aryl, an optionally substituted heteroaryl, or a substituted An optionally substituted alkyl or an optionally substituted cyclo
  • a ring, B ring and C ring are each independently an aryl ring or heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted Or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, tri May be substituted with alkylsilyl, tricycloalkylsilyl, substituted or unsubstituted aryloxy, cyano or halogen; Rings B and C may be linked by> N—R or> O, where R in> N—R is substituted with aryl, alkyl or cycloalkyl optional
  • R in the —C (—R) 2 — may be hydrogen, alkyl or cycloalkyl, Each X is independently> N—R or> O, provided that at least one is>N—R; R in the> N—R is aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, and R is —O—, -S-, -C (-R) 2 -or a single bond may be bonded to the A ring, B ring and / or C ring, wherein R of -C (-R) 2- is hydrogen, alkyl Or cycloalkyl, At least one hydrogen in the compound or structure represented by the formula (B3) may be substituted with halogen or deuterium; In the case of a multimer, it is a dimer or trimer having 2 or 3 structures represented by the formula (B3).
  • Item 9 The organic electrolumin
  • Item 10 The organic according to Item 8, wherein the polycyclic aromatic compound represented by the general formula (B3) or a multimer thereof is a polycyclic aromatic compound represented by the following general formula (B3 ′) or a multimer thereof.
  • Electroluminescent device In the above formula (B3 ′), R 1 to R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen.
  • At least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and adjacent groups of R 1 to R 11 are bonded together to form an aryl together with a ring, b ring or c ring.
  • Ring or heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy , Shea Or may be substituted by halogen, at least one hydrogen in these aryl, heteroaryl, may be substituted by alkyl or cycloalkyl, > R in N—R is independently aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, -O-, -S-, -C (-R) 2 -or a single bond may be bonded to the a ring, b ring and / or c ring, and R of -C (-R) 2- Is alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons,
  • R 1 to R 11 are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms or diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), and Adjacent groups of R 1 to R 11 may be bonded to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring or c ring.
  • At least one hydrogen in the ring formed may be substituted with aryl having 6 to 10 carbon atoms, > R in N—R is independently aryl having 6 to 10 carbon atoms; At least one hydrogen in the compound represented by the formula (B3 ′) or a multimer thereof may be substituted with halogen or deuterium;
  • Item 9 The organic electroluminescent device according to Item 8.
  • Item 12 The organic electroluminescence device according to item 8, wherein the polycyclic aromatic compound represented by the general formula (B3) or a multimer thereof is a compound represented by any one of the following structural formulas.
  • “Me” represents a methyl group
  • “tBu” represents a t-butyl group, which is represented by the above formula (B3-3001), formula (B3-3001-Cz4) or formula (B3-3002).
  • at least one hydrogen may be substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, cyano, halogen or deuterium.
  • Item 13 An electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, BO Item 1 containing at least one selected from the group consisting of a series derivative, anthracene derivative, benzofluorene derivative, phosphine oxide derivative, pyrimidine derivative, carbazole derivative, triazine derivative, benzimidazole derivative, phenanthroline derivative, and quinolinol metal complex
  • the organic electroluminescence device according to any one of 1 to 12.
  • the electron transport layer and / or the electron injection layer further includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, or an alkaline earth metal.
  • Item 13 contains at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes.
  • Item 15. A display device comprising the organic electroluminescent element according to Item 1-14.
  • Item 16 A lighting device comprising the organic electroluminescent element according to any one of Items 1 to 14.
  • the organic EL characteristics such as the light emission characteristics can be further enhanced by the polycyclic aromatic compound represented by the formula (A), which has not been specifically known conventionally, and the light emitting layer.
  • the choice of materials can be increased.
  • Organic electroluminescent device The organic EL device of the present invention has a plurality of polycyclic aromatic compounds represented by the general formula (A) and a structure represented by the general formula (A) as a first component in the light emitting layer. And at least one multimer of aromatic compounds having at least one compound having triplet energy (E T ) of 2.2 to 3.0 eV as a second component.
  • the first component functions as a host component in the light emitting layer, and the second component functions as a dopant component.
  • the polycyclic aromatic compound represented by the first component formula (A) or a multimer thereof has a large HOMO-LUMO gap (band gap Eg in a thin film) and a high triplet excitation energy (E T ). This is because a 6-membered ring containing a hetero element has a low aromatic attribute, so that the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugated system is suppressed, and the triplet excited state (T1) due to the electronic perturbation of the hetero element This is due to the localization of SOMO1 and SOMO2.
  • these polycyclic aromatic compounds can move the energy of HOMO and LUMO arbitrarily by introducing substituents (especially aryloxy groups and heteroaryloxy groups), so that the ionization potential and electron affinity can be controlled by using peripheral materials. It is possible to optimize according to. Since the polycyclic aromatic compound represented by the formula (A) has high triplet energy, it is preferable as a host for phosphorescent materials and thermally activated delayed fluorescent materials.
  • R 1 to R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, the first substitution) And at least one hydrogen in these groups may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (hereinafter, the second substituent).
  • aryl examples include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and 6 to 6 carbon atoms. 16 aryl is more preferred, aryl having 6 to 12 carbon atoms is particularly preferred, and aryl having 6 to 10 carbon atoms is most preferred.
  • aryl examples include, for example, phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, and (1-, 2-) naphthyl which is a condensed bicyclic aryl.
  • Terphenylyl which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) A fused tricyclic aryl, Naphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl
  • aryl as the first substituent is as follows: “aryl” in diarylamino, “aryl” in arylheteroarylamino, “aryl”, diaryl as second substituent The same reference can be made to “aryl” in amino.
  • heteroaryl examples include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, Heteroaryl having 2 to 15 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred.
  • heteroaryl examples include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring constituent atoms.
  • heteroaryl includes, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naph
  • heteroaryl in diheteroarylamino, “heteroaryl” in arylheteroarylamino, “heteroaryl” as first substituent, References can also be made to "heteroaryl”.
  • heteroaryl in the “heteroaryl” as the second substituent, at least one hydrogen in the heteroaryl is aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are groups described later) or A group substituted with cycloalkyl such as cyclohexyl (specific examples will be described later) is also included in the heteroaryl as the second substituent.
  • the second substituent is a carbazolyl group
  • a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also used as the second substituent. Included in the heteroaryl group.
  • alkyl (first substituent) may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms.
  • Alkyl having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms) is preferable, alkyl groups having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms) are more preferable, and alkyl having 1 to 6 carbon atoms (carbon number).
  • 3-6 branched chain alkyl is more preferred, alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred, and methyl is most preferred.
  • alkyl examples 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
  • Cycloalkyl (first substituent) includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, carbon Examples thereof include cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.
  • cycloalkyl examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms, bicyclo [1.0 .1] butyl, 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, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.
  • alkyl or cycloalkyl as the first substituent can be similarly cited for “alkyl” or “cycloalkyl” as the second substituent.
  • the position at which the second substituent, alkyl or cycloalkyl, is substituted with respect to the first substituent is not particularly limited, but is based on the bonding position (position 1) of the first substituent to the a-ring, b-ring and c-ring.
  • the 2nd or 3rd position is preferable, and the 2nd position is more preferable.
  • R 1 to R 11 for example, a group having the following structure is preferable.
  • M is alkyl having 1 to 4 carbon atoms (preferably methyl), cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) or phenyl, and * is a ring with a ring, b ring or c ring.
  • a linking group is shown.
  • At least one hydrogen in the following structure may be substituted with alkyl having 1 to 4 carbons, cycloalkyl having 5 to 10 carbons, preferably methyl, and the substitution position is not particularly limited, but is represented by * Based on the bonding position (1st position), the 2nd position or the 3rd position is preferable, and the 2nd position is more preferable.
  • R 1 to R 11 for example, a group having the following structure is more preferable.
  • Me is methyl
  • M is methyl or phenyl
  • * represents a bonding group to the a ring, b ring, and c ring.
  • adjacent groups of R 1 to R 11 may be bonded together to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring.
  • At least one hydrogen in may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, the first substituent), at least one of which The hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, the second substituent).
  • the polycyclic aromatic compound represented by the general formula (A) has the following formulas (A-L1) and (A-L2) depending on the mutual bonding form of the substituents in the a-ring, b-ring and c-ring. As shown, the ring structure constituting the compound changes.
  • the a ′ ring, b ′ ring and c ′ ring in each formula correspond to the above “formed ring (aryl ring or heteroaryl ring)”. Note that the symbols in the formulas (A-L1) and (A-L2) are the same as the definitions in the formula (A).
  • the compounds represented by the above formulas (AL1) and (AL2) are, for example, a benzene ring, an indole ring, a pyrrole with respect to a benzene ring which is a ring (and / or b ring and / or c ring).
  • Examples of the formed “aryl ring” include an aryl ring having 9 to 30 carbon atoms, preferably an aryl ring having 9 to 24 carbon atoms, more preferably an aryl ring having 9 to 20 carbon atoms, An aryl ring having 9 to 16 carbon atoms is more preferable, an aryl ring having 9 to 12 carbon atoms is particularly preferable, and an aryl having 9 to 10 carbon atoms is most preferable.
  • aryl ring examples include, for example, a naphthalene ring that is a condensed bicyclic system, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring that is a condensed tetracyclic system, and a pyrene.
  • heteroaryl ring examples include a heteroaryl ring having 6 to 30 carbon atoms, preferably a heteroaryl ring having 6 to 25 carbon atoms, and a heteroaryl ring having 6 to 20 carbon atoms. Is more preferable, a heteroaryl ring having 6 to 15 carbon atoms is more preferable, and a heteroaryl ring having 6 to 10 carbon atoms is particularly preferable.
  • heteroaryl ring include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as a ring constituent atom.
  • the total number of carbon atoms of the condensed ring in which a 5-membered ring is condensed is 6
  • the lower limit is the number of carbon atoms.
  • heteroaryl ring examples include indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline Ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, benzofuran ring, isobenzofuran Ring, dibenzofuran ring, benzothiophene ring, dibenzothiophene ring, thianthrene ring and the like.
  • R 2 , R 5 , R 7 , R 8 and R 10 is a group represented by —O—W, and each W is independently aryl or heteroaryl. In which at least one hydrogen may be substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl.
  • aryl and heteroaryl as W
  • the description of aryl and heteroaryl described in the columns of R 1 to R 11 can also be cited.
  • aryl, heteroaryl”, “diarylamino”, “alkyl” and “cycloalkyl” which are substituents to W, aryl, heteroaryl described in the columns of R 1 to R 11 .
  • diarylamino, alkyl and cycloalkyl can also be cited.
  • W is preferably a group having the following structure, for example.
  • * In the following structure represents a bonding group to the ether bond of “—O—W”.
  • at least one hydrogen in the following structure may be substituted with the above-mentioned aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl, preferably an alkyl having 1 to 4 carbon atoms (more preferably methyl or t- Butyl) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl), and the substitution position is not particularly limited, but it is 2 based on the bonding position (position 1) indicated by *.
  • the position or the third position is preferable, and the second position is more preferable.
  • W is more preferably a group having the following structure.
  • Me represents a methyl group
  • tBu represents a t-butyl group.
  • W is a group represented by the formula (W-2-1) to the formula (W-2-5), the formula (W-3-1) to the formula (W-3-5), and the formula (W— The group represented by any one of 38-1) to formula (W-38-5) is more preferred.
  • At least one hydrogen in the polycyclic aromatic compound represented by the formula (A) and the multimer thereof may be independently substituted with halogen or deuterium.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine
  • the polycyclic aromatic compound multimer having a plurality of unit structures represented by the general formula (A) is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer.
  • the multimer may be in a form having a plurality of the unit structures in one compound.
  • the unit structure is a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group.
  • it may be a mode in which any ring (a ring, b ring or c ring) contained in the unit structure is shared by a plurality of unit structures.
  • Arbitrary rings (a-ring, b-ring or c-ring) included in the unit structure may be combined to be condensed.
  • multimers represented by the following formula (A-P1), formula (A-P2-1) to formula (A-P2-4), or formula (A-P3) are multimers represented by the following formula (A-P1), formula (A-P2-1) to formula (A-P2-4), or formula (A-P3). It is done.
  • the multimer represented by the following formula (A-P1) is a unit represented by two general formulas (A) so as to share a benzene ring that is a ring.
  • the multimer represented by the following formulas (A-P2-1) to (A-P2-4) has a benzene ring which is a ring b (or ring c) as described in the general formula (A).
  • the multimer represented by the following formula (A-P3) can be represented by the general formula (A), for example, a benzene ring which is a b ring (or a ring or c ring) of a certain unit structure and a certain unit structure. And a benzene ring which is a ring b (or a ring or c ring) of the above, a multimer having a plurality of unit structures represented by the general formula (A) in one compound.
  • formula is the same as the definition in Formula (A).
  • the multimer is represented by the multimerized form represented by the formula (A-P1) and any one of the formulas (A-P2-1) to (A-P2-4) or the formula (A-P3).
  • a multimer combined with a multimerized form may be used, and a multimerized form represented by any one of formulas (A-P2-1) to (A-P2-4) and a formula (A-P3)
  • a multimerized form represented by formula (A-P1) and formulas (A-P2-1) to (A-P2-) A multimer in which the multimerized form represented by any one of 4) and the multimerized form represented by the formula (AP3) may be combined.
  • any hydrogen may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, particularly methyl or t-butyl.
  • the compound represented by formula (A) is produced by first coupling an a to c ring with a linking group (—O—). (The first reaction), and then the a to c rings can be bonded with a linking group (a group containing X) to produce the final product (second reaction).
  • first reaction for example, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used.
  • second reaction a tandem hetero Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used.
  • the details of the first and second reactions can be referred to the description described in International Publication No. 2015/102118.
  • the second reaction is a reaction for introducing B (boron) that connects the a ring, the b ring, and the c ring.
  • B boron
  • the hydrogen atom between two Os is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like.
  • boron trichloride, boron tribromide, etc. are added, and after lithium-boron metal exchange is performed, Bronsted base such as N, N-diisopropylethylamine is added to cause tandem Bora Friedel-Crafts reaction. You can get things.
  • a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.
  • lithium is introduced into a desired position by orthometalation.
  • a bromine atom or the like is introduced at a position where lithium is to be introduced, and the desired position is also obtained by halogen-metal exchange. Lithium can be introduced.
  • these groups may be introduced into the intermediate in advance, or these may be introduced after the second reaction. These groups may be introduced.
  • the compound represented by the formula (A) having a substituent at a desired position can be synthesized by appropriately selecting the synthesis method described above and appropriately selecting the raw material to be used.
  • the organic EL device of the present invention contains at least one compound having triplet energy (E T ) of 2.2 to 3.0 eV as the second component in the light emitting layer.
  • the triplet energy (E T ) is preferably 2.2 to 2.7 eV, more preferably 2.2 to 2.5 eV. Since the compound of the formula (A) as the first component has a high triplet energy, a phosphorescent material that emits light from the triplet energy and a thermal activity having a small ⁇ E ST (difference between singlet energy and triplet energy).
  • a type delayed fluorescent material can be used.
  • Phosphorescent materials utilize the intramolecular spin-orbit interaction (heavy atom effect) caused by metal atoms to obtain light emission from triplets.
  • Examples of such a second component include compounds represented by the following general formula (B1).
  • M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu
  • n is an integer of 1 to 3
  • X and Y Are each independently a bidentate monoanionic ligand.
  • Examples of the compound represented by the formula (B1) include compounds represented by the following general formula (B1-10) or general formula (B1-15).
  • X ′ is an aromatic ring containing carbon (C) bonded to M
  • Y ′ is a complex containing nitrogen (N) coordinated to M. It is a ring.
  • X 'and Y' are bonded, and X 'and Y' may form a new ring.
  • Z is a bidentate ligand having two oxygens.
  • M is preferably Ir from the viewpoint of high efficiency and long life.
  • Examples of the compound represented by the formula (B1-10) include Ir (ppy) 3 , Ir (ppy) 2 (acac), Ir (mppy) 3 , Ir (PPy) 2 (m-bppy), and BtpIr ( acac), Ir (btp) 2 (acac), Ir (2-phq) 3 , Hex-Ir (phq) 3 , Ir (fbi) 2 (acac), fac-Tris (2- (3-p-xylyl) phenyl) pyridine iridium (III), Eu (dbm) 3 (Phen), Ir (piq) 3 , Ir (piq) 2 (acac), Ir (Fiq) 2 (acac), Ir (Flq) 2 (acac), Ru (dtb-bpy) 3 ⁇ 2 (PF 6), Ir (2-phq) 3, Ir (BT) 2 (acac), Ir (DMP) 3, Ir (
  • Examples of the second component that can be used for such a purpose include a compound represented by the following general formula (B2) or a compound having the following general formula (B2) as a partial structure.
  • ED is an electron donating group
  • Ln is a bonding group
  • EA is an electron accepting group
  • the energy difference ( ⁇ S 1 T 1 ) of the term energy (T 1 ) is 0.2 eV or less (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)).
  • the energy difference ( ⁇ S 1 T 1 ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.
  • the compound represented by the general formula (B2) which is the second component of the present invention is a thermally activated delayed phosphor (TADF compound).
  • Thermally activated delayed phosphors efficiently localize HOMO and LUMO in the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor. It is preferable that the donor-acceptor type TADF compound (DA type TADF compound) is designed so as to cause reverse intersystem crossing.
  • electron-donating substituent means a substituent and a partial structure in which LUMO orbitals are localized in the TADF compound molecule.
  • Group means a substituent and a partial structure in which a HOMO orbital is localized in a TADF compound molecule.
  • a TADF compound using a donor or an acceptor has a large spin orbit coupling (SOC: Spin Orbit Coupling) due to the structure, a small exchange interaction between HOMO and LUMO, and a small ⁇ E (ST). In addition, a very fast inverse intersystem crossing speed is obtained.
  • SOC Spin Orbit Coupling
  • TADF compounds using donors and acceptors have a large structure relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so conversion from the ground state to the excited state by external stimulation) Then, the structure changes to a stable structure in an excited state), and gives a broad emission spectrum. Therefore, when used as a light emitting material, there is a possibility that the color purity is lowered.
  • a fluorescent compound may be added to the light emitting layer or a layer adjacent to the light emitting layer as the third component.
  • the second component serves as an assisting dopant and the third component serves as an emitting dopant.
  • the third component may be a compound whose absorption spectrum of the compound overlaps at least partially with the emission peak of the assisting dopant.
  • the donor-type and acceptor-type structures used in the thermally activated delayed phosphor (TADF compound) of the present invention for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used.
  • the ED include a functional group containing sp 3 nitrogen, and more specifically, carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothieno.
  • Carbazole phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis (tert-butyl) Phenyl) amine, (diphenylamino) phenyl) diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetra Examples thereof include groups derived from methyl-dihydro-indenoacridine and diphenyl-dihydrodibenzoazacillin.
  • EA examples include, for example, an sp 2 nitrogen-containing aromatic ring, a CN-substituted aromatic ring, a ring having a ketone, and a cyano group. More specifically, sulfonyldibenzene, benzophenone, phenylenebis (phenylmethanone), Benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzimidazole, dibenzoquinoxaline, hepta Azaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, pyridine, cycloheptabipyridine, benzenetricarbonitrile, fluorenedicarbonitrile, pyra
  • Ln examples include a single bond and arylene, and more specifically, phenylene, biphenylene, naphthylene, and the like.
  • hydrogen may be substituted with alkyl, cycloalkyl, and aryl.
  • the compound having thermally activated delayed fluorescence of the present invention has, as a partial structure, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole.
  • the compound represented by the general formula (B2) which is the second component of the present invention is a compound represented by any one of the following general formulas (B21), (B22) and (B23). .
  • M is each independently a single bond, —O—,> N—Ar or> CAr 2 , and the HOMO depth and excited singlet energy level and excited triplet energy level of the partial structure to be formed From the viewpoint of height, preferably a single bond, —O— or> N—Ar, J is a spacer structure that separates a donor partial structure and an acceptor partial structure, each independently an arylene having 6 to 18 carbon atoms, and a conjugate that exudes from a donor partial structure and an acceptor partial structure.
  • arylene having 6 to 12 carbon atoms is preferable, and more specifically, phenylene, methylphenylene and dimethylphenylene can be mentioned, Q is each independently ⁇ C (—H) — or ⁇ N—, and is a viewpoint of the LUMO shallowness of the partial structure to be formed and the height of the excited singlet energy level and the excited triplet energy level.
  • N- Ar is each independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 18 carbon atoms, and a partial structure to be formed From the viewpoint of the depth of HOMO and the height of the excited singlet energy level and excited triplet energy level, hydrogen, aryl having 6 to 12 carbons, heteroaryl having 2 to 14 carbons, 1-4 alkyl or cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert- Butylcarbazolyl, benzimidazole or phenylbenzimidazole, more preferably hydrogen Phenyl or carbazolyl, m is 1 or 2,
  • Examples of the compound represented by the formula (B2) include compounds represented by the following structure.
  • * represents a bonding position
  • Me represents a methyl group
  • tBu represents a t-butyl group.
  • the compound represented by the general formula (B2) which is the second component of the present invention includes 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC, among the above specific compounds.
  • the polycyclic aromatic compound represented by the general formula (B3) and the multimer of the polycyclic aromatic compound represented by the general formula (B3) and the polycyclic aromatic compound having a plurality of structures represented by the general formula (B3) are: Preferably, it is a multimer of a polycyclic aromatic compound represented by the following general formula (B3 ′) and a polycyclic aromatic compound having a plurality of structures represented by the following general formula (B3 ′). is there.
  • the A ring, B ring and C ring in the general formula (B3) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent.
  • the substituent is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (aryl and An amino group having a heteroaryl), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, cyano or halogen is preferred.
  • substituents include aryl, heteroaryl, alkyl, and cycloalkyl.
  • the aryl ring or heteroaryl ring has a 5-membered or 6-membered ring that shares a bond with the central condensed bicyclic structure composed of the central element B (boron) and left and right X (B3). It is preferable.
  • the “condensed bicyclic structure” is a structure in which two saturated hydrocarbon rings composed of a central element B (boron) and left and right X shown in the center of the general formula (B3) are condensed. means.
  • the “six-membered ring sharing a bond with the condensed bicyclic structure” means, for example, an a ring (benzene ring (six-membered ring)) condensed to a condensed bicyclic structure as shown in the general formula (B3 ′). means.
  • the aryl ring or heteroaryl ring (which is A ring) has this 6-membered ring means that the A ring is formed only by this 6-membered ring or includes this 6-membered ring. It means that another ring or the like is further condensed to this 6-membered ring to form A ring.
  • the term “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 part of the A ring is fused to a condensed bicyclic structure. Means that The same description applies to “B ring (b ring)”, “C ring (c ring)”, and “5-membered ring”.
  • Rings B and C may be connected by> N—R or> O, and R in> N—R may be an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted R may be alkyl or optionally substituted cycloalkyl, and R may be bonded to the B ring and / or C ring by a linking group or a single bond. This detailed description will be described later.
  • a ring (or B ring, C ring) in the general formula (B3) is a ring in the general formula (B3 ′) and its substituents R 1 to R 3 (or b ring and its substituents R 8 to R 11 , corresponding to ring c and its substituents R 4 to R 7 ). That is, the general formula (B3 ′) corresponds to a structure in which “A to C rings having a 6-membered ring” are selected as the A to C rings of the general formula (B3). In that sense, each ring of the general formula (B3 ′) is represented by lowercase letters a to c.
  • adjacent groups of the substituents R 1 to R 11 of the a ring, the b ring and the c ring are bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring.
  • at least one hydrogen in the ring formed is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen
  • at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • the polycyclic aromatic compound represented by the general formula (B3 ′) has the following formula (B3′-1) and formula (B3 ′) depending on the mutual bonding form of the substituents in the a-ring, b-ring and c-ring. As shown in -2), the ring structure constituting the compound changes. A ′ ring, B ′ ring and C ′ ring in each formula correspond to A ring, B ring and C ring in general formula (B3), respectively. Note that the symbols in the formulas (B3′-1) and (B3′-2) are the same as the definitions in the formula (B3).
  • the A ′ ring, the B ′ ring and the C ′ ring are represented by the general formula (B3 ′) as defined by the substituents R 1 to R 11 .
  • Adjacent groups are bonded to each other to indicate an aryl ring or a heteroaryl ring formed with a ring, b ring and c ring, respectively (a ring structure formed by condensing another ring structure to a ring, b ring or c ring).
  • a condensed ring ).
  • the b ring and the c ring in the general formula (B3 ′) To form> N—R or> O (preferably a position of R 8 on the b ring and a position of R 7 on the c ring form a> N—R bond or> O bond).
  • the compound represented by the formula (B3′-1) or the formula (B3′-2) is, for example, a benzene ring, an indole ring, a pyrrole ring, a benzene ring which is a ring (or b ring or c ring),
  • a compound having an A ′ ring (or B ′ ring or C ′ ring) formed by condensation of a benzofuran ring or a benzothiophene ring, etc., and formed condensed ring A ′ (or condensed ring B ′ or condensed ring) Ring C ′) is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or the like.
  • X in the general formula (B3) is each independently>N—R,>O,> C (—R) 2 ,> S or> Si (—R) 2.
  • R in C (—R) 2 or> Si (—R) 2 is independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted R of the above-mentioned>N—R,> C (—R) 2 or> Si (—R) 2 is bonded to the A ring, B ring and / or C ring by a linking group or a single bond.
  • the linking group is preferably —O—, —S— or —C (—R) 2 —.
  • R in the “—C (—R) 2 —” is hydrogen, alkyl or cycloalkyl.
  • This explanation is the same for>N—R,> C (—R) 2 or> Si (—R) 2 as X in formula (B3 ′).
  • This explanation is the same for> N—R in the case of connecting the B ring and the C ring in the general formula (B3) (the b ring and the c ring in the general formula (B3 ′)).
  • “>N—R,> C (—R) 2 or> Si (—R) 2 R represents the A ring, B ring and / or C ring by a linking group or a single bond.
  • the definition of “bonded to” is that in general formula (B3 ′), “>N—R,> C (—R) 2, or> Si (—R) 2 is —O—, —S—, This corresponds to the definition of “attached to the a ring, b ring and / or c ring by —C (—R) 2 — or a single bond”.
  • N—R which has a ring structure represented by the following formula (B3′-3-1), in which N is incorporated into the condensed ring B ′ and the condensed ring C ′. It can be expressed as a compound. That is, for example, a B ′ ring (or C ′ ring) formed by condensing another ring so as to incorporate N into the benzene ring which is the b ring (or c ring) in the general formula (B3 ′). It is a compound that has.
  • the formed condensed ring B ′ (or condensed ring C ′) is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
  • the condensed ring B ′ (or condensed ring C ′) formed when C or Si is incorporated is, for example, a xanthene ring, thioxanthene ring, dihydroanthracene ring, dibenzooxyline ring, dibenzothiacillin ring or dihydrodibenzo ring. Syrin ring. Further, the above definition will explain the case where X is> N—R.
  • N is represented by the following formula (B3′-3-2) or formula (B3′-3-3), and N is a condensed ring A ′. It can also be expressed by a compound having an incorporated ring structure. That is, for example, a compound having an A ′ ring formed by condensing another ring so as to incorporate N into the benzene ring which is the a ring in the general formula (B3 ′).
  • the formed condensed ring A ′ is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
  • the condensed ring A ′ formed when C or Si is incorporated is, for example, a xanthene ring, a thioxanthene ring, a dihydroanthracene ring, a dibenzooxyline ring, a dibenzothiacillin ring, or a dihydrodibenzocillin ring.
  • the symbols in the formulas (B3′-3-1) to (B3′-3-3) have the same definitions as in the formula (B3 ′).
  • Examples of the “aryl ring” that is the A ring, B ring and C ring in the general formula (B3) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, An aryl ring having 6 to 12 carbon atoms is more preferable, and an aryl ring having 6 to 10 carbon atoms is particularly preferable.
  • the “aryl ring” is an aryl ring formed together with a ring, b ring or c ring by bonding adjacent groups of “R 1 to R 11 ” defined by the general formula (B3 ′).
  • the total carbon number 9 of the condensed ring in which a 5-membered ring is condensed is the lower limit. It becomes carbon number.
  • aryl rings include monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings, tricyclic terphenyl rings (m-terphenyl, o -Terphenyl, p-terphenyl), condensed tricyclic systems such as acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, condensed tetracyclic systems such as triphenylene ring, pyrene ring, naphthacene ring, condensed pentacyclic system Examples include perylene ring and pentacene ring.
  • heteroaryl ring that is the A ring, B ring and C ring of the general formula (B3) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms.
  • a heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is more preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable.
  • heteroaryl ring include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as a ring constituent atom.
  • the “heteroaryl ring” is a heterocycle formed by combining adjacent groups of “R 1 to R 11 ” defined by the general formula (B3 ′) together with a ring, b ring or c ring. Since the a ring (or b ring or c ring) is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the condensed ring condensed with a 5-membered ring is The lower limit is the number of carbon atoms.
  • heteroaryl ring examples include pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring Cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, p
  • At least one hydrogen in the above “aryl ring” or “heteroaryl ring” is the first substituent, which is substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “Diarylamino”, substituted or unsubstituted “diheteroarylamino”, substituted or unsubstituted “arylheteroarylamino”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “cycloalkyl”, substituted or An aryl of “aryl”, “heteroaryl” or “diarylamino” as the first substituent, which may be substituted with unsubstituted “alkoxy”, or substituted or unsubstituted “aryloxy” , "Diheteroarylamino" heteroaryl, "arylheteroarylamino” aryl and heteroaryl Lumpur, also include monovalent
  • 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 or a branched chain alkyl having 3 to 24 carbon atoms.
  • Alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons) is preferable, alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons) is more preferable, and alkyl having 1 to 6 carbons. (Branched alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferable.
  • alkyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, and 1-methyl.
  • Pentyl 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propyl Pentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n- Tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-hepta Sill, n- octadecyl, etc. n- eicosyl and the like.
  • 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.
  • cycloalkyl examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms, bicyclo [1.0 .1] butyl, 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, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.
  • examples of the “alkoxy” as the first substituent include straight-chain alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms.
  • C1-C18 alkoxy (C3-C18 branched alkoxy) is preferred, C1-C12 alkoxy (C3-C12 branched alkoxy) is more preferred, and C1-C6 Of alkoxy (C3-C6 branched chain alkoxy) is more preferable, and C1-C4 alkoxy (C3-C4 branched chain alkoxy) is particularly preferable.
  • alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.
  • halogen as the first substituent is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.
  • the first substituent, substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “diarylamino”, substituted or unsubstituted “diheteroarylamino”, substituted Or unsubstituted “arylheteroarylamino”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “cycloalkyl”, substituted or unsubstituted “alkoxy”, or substituted or unsubstituted “aryloxy” Are described as substituted or unsubstituted, in which at least one hydrogen may be substituted with a second substituent.
  • Examples of the second substituent include aryl, heteroaryl, alkyl, and cycloalkyl. Specific examples thereof include the above-described monovalent group of “aryl ring” or “heteroaryl ring”, and the like. Reference may be made to the description of “alkyl” or “cycloalkyl” as one substituent.
  • at least one hydrogen in them is aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described above) or cyclohexyl.
  • a group substituted with cycloalkyl is also included in the aryl and heteroaryl as the second substituent.
  • the second substituent is a carbazolyl group
  • a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also used. Is included in the heteroaryl as a substituent.
  • aryl As aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, or aryloxy of aryloxy in R 1 to R 11 of formula (B3 ′), And a monovalent group of “aryl ring” or “heteroaryl ring” described in formula (B3).
  • alkyl cycloalkyl or alkoxy in R 1 to R 11 , see the description of “alkyl”, “cycloalkyl” or “alkoxy” as the first substituent in the description of the general formula (B3). can do.
  • aryl, heteroaryl, alkyl or cycloalkyl as a substituent for these groups.
  • adjacent groups of R 1 to R 11 are bonded to form an aryl ring or a heteroaryl ring together with a ring, b ring or c ring, it is a substituent to these rings.
  • R in general formula (B3)>N—R,> C (—R) 2 or> Si (—R) 2 is aryl, heteroaryl, alkyl or the like, optionally substituted with the second substituent described above
  • Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above.
  • aryl having 6 to 10 carbon atoms eg phenyl, naphthyl etc.
  • heteroaryl having 2 to 15 carbon atoms eg carbazolyl etc.
  • alkyl having 1 to 4 carbon atoms eg methyl, ethyl etc.
  • cycloalkyl such as bicyclooctyl and adamantyl are preferred.
  • R in “—C (—R) 2 —” which is a linking group in the general formula (B3) is hydrogen, alkyl or cycloalkyl, and examples of the alkyl and cycloalkyl include the groups described above. In particular, alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, etc.) is preferable. This explanation is the same for “—C (—R) 2 —” which is a linking group in formula (B3 ′).
  • the emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of R 1 to R 11 (first substituent), and R 1 to R 11 are preferably represented by the following formulae.
  • Group wherein * represents a bonding position, “Me” represents a methyl group, and “tBu” represents a t-butyl group), and more preferably methyl, t-butyl, bicyclooctyl, cyclohexyl, adamantyl, phenyl , O-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t -Butyl) phenyl) amino, diphenylboryl, dimesitylboryl, dibenzooxaborinyl, phenyldibenz
  • a larger steric hindrance is preferred for selective synthesis.
  • t-butyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.
  • the light-emitting layer has a multimer of polycyclic aromatic compounds having a plurality of unit structures represented by the general formula (B3), preferably a polycycle having a plurality of unit structures represented by the general formula (B3 ′).
  • Multimers of aromatic compounds may be included.
  • the multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer.
  • the multimer may be in a form having a plurality of the unit structures in one compound.
  • the unit structure is a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group.
  • any ring (A ring, B ring or C ring, a ring, b ring or c ring) included in the unit structure is bonded so as to be shared by a plurality of unit structures
  • any ring (A ring, B ring or C ring, a ring, b ring or c ring) included in the unit structure may be combined to be condensed. Good.
  • Examples of such multimers include the following formula (B3′-4), formula (B3′-4-1), formula (B3′-4-2), formula (B3′-5-1) to formula (B3′-4-1) And a multimeric compound represented by (B3′-5-4) or formula (B3′-6).
  • Formula (B3′-4) is a dimer compound, Formula (B3′-4-1) is a dimer compound, Formula (B3′-4-2) is a trimer compound, Formula (B3′-5) -1) is a dimer compound, formula (B3'-5-2) is a dimer compound, formula (B3'-5-3) is a dimer compound, and formula (B3'-5-4) is 3
  • the dimer compound, formula (B3′-6) is a dimer compound.
  • the multimeric compound represented by the following formula (B3′-4) is represented by the general formula (B3 ′), and can be divided into a plurality of general formulas (B3 ′) by sharing a benzene ring that is a ring. It is a multimeric compound having a unit structure represented in one compound.
  • the multimeric compound represented by the following formula (B3′-4-1) can be represented by the two general formulas (B3 ′) by sharing a benzene ring that is a ring.
  • the multimeric compound represented by the following formula (B3′-4-2) can be represented by the three general formulas (B3 ′) so as to share a benzene ring which is a ring.
  • the multimeric compounds represented by the following formulas (B3′-5-1) to (B3′-5-4) can be represented by the b ring (or c ring) in the general formula (B3 ′).
  • the multimeric compound represented by the following formula (B3′-6) can be represented by the general formula (B3 ′), for example, a benzene ring which is a b ring (or a ring or c ring) of a certain unit structure, and A multimeric compound having a unit structure represented by a plurality of general formulas (B3 ′) in one compound so that a benzene ring which is a b ring (or a ring or c ring) of a certain unit structure is condensed. It is.
  • symbol in each following formula is the same as the definition in Formula (B3 ').
  • the multimeric compound includes a multimerized form represented by the formula (B3′-4), the formula (B3′-4-1) or the formula (B3′-4-2), the formula (B3′-5-1) A multimer in combination with any of the formulas (B3′-5-4) or a multimerized form represented by the formula (B3′-6) may be used, and the formula (B3′-5-1) A multimer in which the multimerized form represented by any one of the formula (B3′-5-4) and the multimerized form represented by the formula (B3 ′) are combined may be used.
  • a multimerization form represented by formula (B3'-4-1) or formula (B3'-4-2) and formulas (B3'-5-1) to (B3'-5-4) A multimer in which the multimerized form represented by any one and the multimerized form represented by the formula (B3′-6) are combined may be used.
  • all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (B3) or (B3 ′) and its multimer may be deuterium.
  • all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (B3) or (B3 ′) and the multimer thereof may be cyano or halogen.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.
  • the polycyclic aromatic compound represented by the general formula (B3) and its multimer preferably include the following partial structures.
  • polycyclic aromatic compound represented by the general formula (B3) and the multimer thereof include compounds represented by the following structural formula.
  • “Me” represents a methyl group
  • “tBu” represents a t-butyl group.
  • Formula (B3-3001), Formula (B3-3001-Cz1) to Formula (B3-3001-Cz9), Formula (B3-3002), Formula (B3-3002-Cz1), and Formula (B3-3002-Cz2) At least one hydrogen in the compound represented by any of the above may be substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, cyano, halogen or deuterium.
  • the polycyclic aromatic compound represented by the formula (B3) and the multimer thereof include a central element B (boron) in at least one of the A ring, the B ring, and the C ring (a ring, b ring, and c ring).
  • a central element B boron
  • the polycyclic aromatic compound represented by the formula (B3) and the multimer thereof include a central element B (boron) in at least one of the A ring, the B ring, and the C ring (a ring, b ring, and c ring).
  • HOMO on the benzene rings that are A ring, B ring and C ring is more meta-positioned with respect to boron. Since the LUMO is localized in the ortho and para positions with respect to boron, an improvement in T1 energy can be particularly expected.
  • R is alkyl or cycloalkyl, and the alkyl may be either linear or branched.
  • linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms may be used.
  • alkyl having 1 to 18 carbon atoms branched alkyl having 3 to 18 carbon atoms
  • more preferred are alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), and 1 to 1 carbon atoms are preferred.
  • alkyl having 6 branched alkyl having 3 to 6 carbon atoms
  • alkyl having 1 to 4 carbons branched alkyl having 3 to 4 carbon atoms
  • cycloalkyl is having 3 to 24 carbon atoms.
  • Cycloalkyl, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, carbon 5-8 cycloalkyl, cycloalkyl having 5 to 6 carbon atoms, such as cycloalkyl having 5 carbon atoms can be mentioned.
  • R include phenyl.
  • “PhO—” is a phenyloxy group, which may be substituted with linear or branched alkyl or cycloalkyl.
  • alkyl linear alkyl having 1 to 24 carbon atoms or Branched chain alkyl having 3 to 24 carbon atoms, alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), carbon number 1-6 alkyl (C3-C6 branched alkyl), C1-C4 alkyl (C3-C4 branched alkyl), and cycloalkyl, C3-C24 cycloalkyl, Cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5
  • polycyclic aromatic compound represented by the formula (B3) and multimers thereof include ones in which at least one hydrogen in one or a plurality of aromatic rings in the compound is 1 And a compound substituted with one or more alkyls, cycloalkyls or aryls, more preferably 1 to 2 alkyls having 1 to 12 carbons, cycloalkyls having 3 to 16 carbons or 6 to 10 carbons. And an aryl-substituted compound. Specifically, the following compounds are mentioned.
  • R in the following formulas are each independently alkyl having 1 to 12 carbons, cycloalkyl having 3 to 16 carbons or aryl having 6 to 10 carbons, preferably alkyl having 1 to 4 carbons, and 5 to 10 carbons.
  • n is independently 0 to 2, preferably 1.
  • polycyclic aromatic compound represented by the formula (B3) and multimers thereof include at least one hydrogen in one or more phenyl groups or one phenylene group in the compound.
  • a compound in which any one of the four positions is preferably substituted with a methyl group is exemplified.
  • the polycyclic aromatic compound represented by the formula (B3) and a multimer thereof can be produced according to the production method described in International Publication No. 2015/102118. Further, referring to the method for producing the polycyclic aromatic compound represented by the above formula (A) and the multimer thereof, the general amination reaction such as the Buchwald-Hartwig reaction rather than the etherification reaction in the first reaction Can be used.
  • FIG. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.
  • An organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole A hole transport layer 104 provided on the injection layer 103; a light-emitting layer 105 provided on the hole transport layer 104; an electron transport layer 106 provided on the light-emitting layer 105; An electron injection layer 107 provided on the electron injection layer 106 and a cathode 108 provided on the electron injection layer 107 are included.
  • 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.
  • An electron transport layer 106 provided on the light emitting layer 105, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer 104.
  • the hole injection layer 103 provided on the hole injection layer 103 and the anode 102 provided on the hole injection layer 103 may be used.
  • each said layer may consist of a single layer, respectively, and may consist of multiple layers.
  • the layer constituting the organic EL element in addition to the above-described configuration aspect of “substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode”, “Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode”, “substrate / Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode ”,“ substrate / Anode / light emitting layer / electron transport layer / electron injection layer / cathode ”,“ substrate / Anode /
  • the substrate substrate 101 in the organic electroluminescent element 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 into a plate shape, a film shape, or a sheet shape according to the purpose.
  • a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used.
  • glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone and the like are preferable.
  • soda lime glass, non-alkali glass, or the like is used, and the thickness only needs to be sufficient to maintain the mechanical strength.
  • the upper limit value of the thickness is, for example, 2 mm or less, preferably 1 mm or less.
  • the glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass.
  • soda lime glass with a barrier coat such as SiO 2 is also commercially available, so it can be used. it can.
  • the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one surface in order to improve the gas barrier property, and a synthetic resin plate, film or sheet having a low gas barrier property is used as the substrate 101. When used, it is preferable to provide a gas barrier film.
  • the anode 102 in the organic electroluminescent element plays a role of injecting holes into the light emitting layer 105.
  • the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .
  • Examples of the material for forming the anode 102 include inorganic compounds and organic compounds.
  • Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide) Products (IZO), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, and the like.
  • Examples of the organic compound include polythiophene such as poly (3-methylthiophene), conductive polymer such as polypyrrole and polyaniline, and the like. In addition, it can select suitably from the substances used as an anode of an organic EL element.
  • the resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but is preferably low resistance from the viewpoint of power consumption of the light emitting element.
  • an ITO substrate of 300 ⁇ / ⁇ or less functions as an element electrode, but at present, since it is possible to supply a substrate of about 10 ⁇ / ⁇ , for example, 100 to 5 ⁇ / ⁇ , preferably 50 to 5 ⁇ . It is particularly desirable to use a low resistance product of / ⁇ .
  • the thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 50 to 300 nm.
  • the hole injection layer, the hole transport layer, and the hole injection layer 103 in the organic electroluminescence device have a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. Fulfill.
  • the hole transport layer 104 serves to efficiently transport 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 each formed by laminating and mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. It is formed.
  • an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.
  • a hole injection / transport material As a hole injection / transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. The hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do. For this purpose, it is preferable to use a substance that has a low ionization potential, a high hole mobility, excellent stability, and is less likely to generate trapping impurities during production and use.
  • a compound conventionally used as a charge transport material for holes in a photoconductive material, a p-type semiconductor, and a hole injection layer of an organic EL element are used.
  • known compounds used in the hole transport layer can be arbitrarily selected and used. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), triarylamine derivatives (aromatic tertiary class).
  • polycarbonates, styrene derivatives, polyvinylcarbazole, polysilanes, etc. having the aforementioned monomers in the side chain are preferred, but light emission There is no particular limitation as long as it is a compound that forms a thin film necessary for manufacturing the device, can inject holes from the anode, and can further transport holes.
  • organic semiconductors are strongly influenced by the doping.
  • Such an organic semiconductor matrix material 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 of electron donor materials.
  • TCNQ tetracyanoquinone dimethane
  • F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane
  • the light emitting layer 105 in the organic electroluminescence device emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied.
  • the material for forming the light-emitting layer 105 may be a compound that emits light by being excited by recombination of holes and electrons (a light-emitting compound), can form a stable thin film shape, and is in a solid state It is preferable that the compound exhibits a strong light emission (fluorescence) efficiency.
  • the light emitting layer may be either a single layer or a plurality of layers, each formed of a light emitting layer material (host material, dopant material).
  • a light emitting layer material host material, dopant material
  • Each of the host material and the dopant material may be one kind or a combination of plural kinds.
  • the dopant material may be included in the host material as a whole, or may be included partially.
  • the polycyclic aromatic compound represented by the formula (A), which is the first component, and a multimer thereof can be used as a host material.
  • the compound represented by Formula (B1), Formula (B2), or Formula (B3), which is the second component can be used as a dopant material.
  • the amount of host material used depends on the type of host material and can be determined according to the characteristics of the host material.
  • the amount of the host material used is preferably 50 to 99.999% by weight, more preferably 70 to 99.9% by weight, and even more preferably 80 to 99.9% by weight of the entire light emitting layer material. Particularly preferred is 90 to 99.9% by weight.
  • the amount of dopant material used depends on the type of dopant material, and can be determined according to the characteristics of the dopant material.
  • the standard of the amount of dopant used is preferably 0.001 to 50% by weight, more preferably 0.1 to 30% by weight, even more preferably 0.1 to 20% by weight of the entire material for the light emitting layer. It is particularly preferably 0.1 to 10% by weight. The above range is preferable in that, for example, the concentration quenching phenomenon can be prevented.
  • Examples of host materials that can be used in combination with the compound represented by formula (A) include fused ring derivatives such as anthracene and pyrene that have been known as light emitters, and bisstyryl such as bisstyrylanthracene derivatives and distyrylbenzene derivatives. Derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, and the like.
  • condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazoles Derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, distyrylbenzene derivatives, etc.
  • condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pent
  • blue to blue-green dopant materials include naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, chrysene and other aromatic hydrocarbon compounds and derivatives thereof, furan, pyrrole, thiophene, Aromatic complex such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene Ring compounds and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazo
  • green to yellow dopant material examples include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene.
  • a compound in which a substituent capable of increasing the wavelength such as aryl, heteroaryl, arylvinyl, amino, cyano is introduced into the compound exemplified as a blue-green dopant material is also a suitable example.
  • orange to red dopant materials include naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone Derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazo Derivatives, thi
  • the dopant can be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13, and references cited therein.
  • the amine having a stilbene structure is represented by the following formula, for example.
  • Ar 1 is an m-valent group derived from aryl having 6 to 30 carbon atoms
  • Ar 2 and Ar 3 are each independently aryl having 6 to 30 carbon atoms
  • Ar 1 to Ar At least one of 3 has a stilbene structure
  • Ar 1 to Ar 3 may be substituted
  • m is an integer of 1 to 4.
  • the amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula.
  • Ar 2 and Ar 3 are each independently aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted.
  • aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, stilbene, distyrylbenzene, distyrylbiphenyl, and distyryl.
  • fluorene include fluorene.
  • amines having a stilbene structure include N, N, N ′, N′-tetra (4-biphenylyl) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (1-naphthyl) ) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (2-naphthyl) -4,4′-diaminostilbene, N, N′-di (2-naphthyl) -N, N '-Diphenyl-4,4'-diaminostilbene, N, N'-di (9-phenanthryl) -N, N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis [4 "-bis (Diphenylamino) styryl] -biphenyl, 1,4-bis [4′-bis (diphenylamino)
  • perylene derivatives examples include 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, 3,10-diphenylperylene, 3,4- Diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) -8,11-di (t-butyl) perylene 3- (9′-anthryl) -8,11-di (t-butyl) perylene, 3,3′-bis (8,11-di (t-butyl) perylenyl), and the like.
  • JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, Perylene derivatives described in JP-A No. 2000-34234, JP-A No. 2001-267075, JP-A No. 2001-217077 and the like may be used.
  • borane derivatives examples include 1,8-diphenyl-10- (dimesitylboryl) anthracene, 9-phenyl-10- (dimesitylboryl) anthracene, 4- (9′-anthryl) dimesitylborylnaphthalene, 4- (10 ′ -Phenyl-9'-anthryl) dimesitylborylnaphthalene, 9- (dimesitylboryl) anthracene, 9- (4'-biphenylyl) -10- (dimesitylboryl) anthracene, 9- (4 '-(N-carbazolyl) phenyl) And -10- (dimesitylboryl) anthracene.
  • the aromatic amine derivative is represented by the following formula, for example.
  • Ar 4 is an n-valent group derived from aryl having 6 to 30 carbon atoms
  • Ar 5 and Ar 6 are each independently aryl having 6 to 30 carbon atoms
  • Ar 4 to Ar 6 are It may be substituted and n is an integer from 1 to 4.
  • Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene
  • Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms
  • Ar 4 to Ar 6 Are more preferably aromatic amine derivatives wherein n is 2 and n is 2.
  • aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorenephenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, and pentacene.
  • the chrysene type includes, for example, N, N, N ′, N′-tetraphenylchrysene-6,12-diamine, N, N, N ′, N′-tetra (p-tolyl) Chrysene-6,12-diamine, N, N, N ′, N′-tetra (m-tolyl) chrysene-6,12-diamine, N, N, N ′, N′-tetrakis (4-isopropylphenyl) chrysene -6,12-diamine, N, N, N ', N'-tetra (naphthalen-2-yl) chrysene-6,12-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) ) Chrysene-6,12-diamine, N, N′-diphenyl-N, N′-bis (4
  • Examples of the pyrene series include N, N, N ′, N′-tetraphenylpyrene-1,6-diamine, N, N, N ′, N′-tetra (p-tolyl) pyrene-1,6.
  • anthracene system examples include N, N, N, N-tetraphenylanthracene-9,10-diamine, N, N, N ′, N′-tetra (p-tolyl) anthracene-9,10-diamine.
  • Examples of coumarin derivatives include coumarin-6 and coumarin-334. Moreover, you may use the coumarin derivative described in Unexamined-Japanese-Patent No. 2004-43646, Unexamined-Japanese-Patent No. 2001-76876, and Unexamined-Japanese-Patent No. 6-298758.
  • Examples of the pyran derivative include the following DCM and DCJTB. Also, JP 2005-126399, JP 2005-097283, JP 2002-234892, JP 2001-220577, JP 2001-081090, and JP 2001-052869. Alternatively, pyran derivatives described in the above may be used.
  • Electron injection layer and electron transport layer in the organic electroluminescence device The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106.
  • the electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105.
  • the electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more electron transport / injection materials or a mixture of the electron transport / injection material and the polymer binder.
  • the electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and further transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is preferable to use a substance that has a high electron affinity, a high electron mobility, excellent stability, and is unlikely to generate trapping impurities during production and use. However, considering the transport balance between holes and electrons, if the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination is mainly played, the electron transport capability is much higher. Even if it is not high, the effect of improving the luminous efficiency is equivalent to that of a material having a high electron transport capability. Therefore, the electron injection / transport layer in this embodiment may include a function of a layer that can efficiently block the movement of holes.
  • a material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 a compound conventionally used as an electron transport compound in a photoconductive material, used for an electron injection layer and an electron transport layer of an organic EL element It can be used by arbitrarily selecting from known compounds.
  • a compound composed of an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus It is preferable to contain at least one selected from pyrrole derivatives, condensed ring derivatives thereof, and metal complexes having electron-accepting nitrogen.
  • condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives Quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives.
  • metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.
  • electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazoles.
  • metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Can be mentioned.
  • the above-mentioned materials can be used alone, but they may be mixed with different materials.
  • borane derivatives pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol metals Complexes are preferred.
  • the borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.
  • R 11 and R 12 are each independently hydrogen, alkyl, cycloalkyl, aryl that may be substituted, silyl that is substituted, or nitrogen that may be substituted A heterocyclic ring, or at least one of cyano
  • R 13 to R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl.
  • X is an optionally substituted arylene
  • Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl
  • n Are each independently an integer of 0 to 3.
  • substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl, alkyl, cycloalkyl and the like.
  • R 11 and R 12 are each independently hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen which may be substituted
  • a heterocycle containing at least one of cyano and R 13 to R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl or an optionally substituted aryl.
  • Each of R 21 and R 22 is independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; is one, X 1 is substituted carbon atoms and optionally more than 20 arylene, n is an integer of 0-3 each independently, To, m are each independently an integer of 0-4.
  • substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl, alkyl, cycloalkyl and the like.
  • R 11 and R 12 are each independently hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which is substituted, nitrogen which may be substituted
  • a heterocycle containing at least one of cyano and R 13 to R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl or an optionally substituted aryl.
  • X 1 is an optionally substituted arylene having 20 or less carbon atoms, and n is each independently an integer of 0 to 3.
  • substituent in the case of “which may be substituted” or “substituted” include aryl, heteroaryl, alkyl, cycloalkyl and the like.
  • X 1 include divalent groups represented by the following formulas (X-1) to (X-9). (In each formula, each R a is independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)
  • This borane derivative can be produced using a known raw material and a known synthesis method.
  • the pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2).
  • ⁇ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4 is there.
  • R 11 to R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbons), cycloalkyl (preferably cyclohexane having 3 to 12 carbons). Alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms).
  • R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cyclohexane having 3 to 12 carbon atoms). Alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms), and R 11 and R 12 may be bonded to form a ring.
  • the “pyridine substituent” is any of the following formulas (Py-1) to (Py-15), and each pyridine substituent is independently an alkyl or carbon having 1 to 4 carbon atoms. It may be substituted with cycloalkyl of several 5-10. Further, the pyridine-based substituent may be bonded to ⁇ , anthracene ring or fluorene ring in each formula through a phenylene group or a naphthylene group.
  • the pyridine-based substituent is any one of the above formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44) It is preferable.
  • At least one hydrogen in each pyridine derivative may be substituted with deuterium, and among the two “pyridine substituents” in the above formula (ETM-2-1) and formula (ETM-2-2) One of these may be replaced by aryl.
  • Alkyl in R 11 to R 18 may be linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms.
  • Preferred “alkyl” is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferable “alkyl” is alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons). More preferable “alkyl” is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred “alkyl” is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).
  • alkyl examples 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-undecy
  • alkyl having 1 to 4 carbon atoms to be substituted on the pyridine-based substituent As the above description of alkyl can be cited.
  • cycloalkyl in R 11 to R 18 examples include cycloalkyl having 3 to 12 carbon atoms. Preferred “cycloalkyl” is cycloalkyl having 3 to 10 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 3 to 8 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 3 to 6 carbon atoms. Specific examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.
  • preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, and still more preferred is aryl having 6 to 14 carbon atoms. And particularly preferred is aryl having 6 to 12 carbon atoms.
  • aryl having 6 to 30 carbon atoms include monocyclic aryl phenyl, condensed bicyclic aryl (1-, 2-) naphthyl, condensed tricyclic aryl acenaphthylene- ( 1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalen- (1-, 2-) yl, (1-, 2 -, 3-, 4-, 9-) phenanthryl, condensed tetracyclic aryl triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, naphthacene- (1- , 2-, 5-) yl, perylene- (1-, 2-, 3-) yl which is a fused pentacyclic aryl, pentacene- (1-, 2-, 5-, 6-) yl and the like. .
  • aryl having 6 to 30 carbon atoms includes phenyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl and the like, more preferably phenyl, 1-naphthyl, 2-naphthyl and phenanthryl, particularly preferably phenyl, 1 -Naphthyl or 2-naphthyl.
  • R 11 and R 12 in the above formula (ETM-2-2) may be bonded to form a ring.
  • the 5-membered ring of the fluorene skeleton includes cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, Cyclohexane, fluorene, indene and the like may be spiro-bonded.
  • pyridine derivative examples include the following.
  • This pyridine derivative can be produced using a known raw material and a known synthesis method.
  • the fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is disclosed in detail in International Publication No. 2010/134352.
  • X 12 to X 21 are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted Represents heteroaryl.
  • substituent when substituted include aryl, heteroaryl, alkyl, and cycloalkyl.
  • fluoranthene derivative examples include the following.
  • the BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by the following formula (ETM-4).
  • R 1 to R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen May be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • adjacent groups of R 1 to R 11 may be bonded to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring May be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen is aryl, heteroaryl, alkyl or It may be substituted with cycloalkyl.
  • At least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.
  • This BO derivative can be produced using a known raw material and a known synthesis method.
  • One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).
  • Ar is each independently divalent benzene or naphthalene, and R 1 to R 4 are each independently hydrogen, alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons or carbon number 6 to 20 aryls.
  • Ar can be independently selected as appropriate from divalent benzene or naphthalene, and the two Ar may be different or the same, but the same from the viewpoint of the ease of synthesis of the anthracene derivative. It is preferable that Ar is bonded to pyridine to form a “part consisting of Ar and pyridine”. This part is an anthracene as a group represented by any of the following formulas (Py-1) to (Py-12), for example. Is bound to.
  • a group represented by any one of the above formulas (Py-1) to (Py-9) is preferable, and any one of the above formulas (Py-1) to (Py-6) may be used. More preferred are the groups
  • the two “sites consisting of Ar and pyridine” bonded to anthracene may have the same structure or different structures, but are preferably the same structure from the viewpoint of ease of synthesis of the anthracene derivative. However, from the viewpoint of device characteristics, it is preferable that the structures of the two “sites composed of Ar and pyridine” are the same or different.
  • the alkyl having 1 to 6 carbon atoms in R 1 to R 4 may be linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferred is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).
  • cycloalkyl having 3 to 6 carbon atoms in R 1 to R 4 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.
  • the aryl having 6 to 20 carbon atoms in R 1 to R 4 is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.
  • aryl having 6 to 20 carbon atoms include monocyclic aryl phenyl, (o-, m-, p-) tolyl, (2,3-, 2,4-, 2,5- , 2,6-, 3,4-, 3,5-) xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumenyl, bicyclic aryl (2 -, 3-, 4-) biphenylyl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4) which is a tricyclic aryl '-Yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2
  • aryl having 6 to 20 carbon atoms is phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5′-yl. More preferred is phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferred is phenyl.
  • One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).
  • Ar 1 is each independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.
  • Ar 2 is independently an aryl having 6 to 20 carbon atoms, and the same description as “aryl having 6 to 20 carbon atoms” in the above formula (ETM-5-1) can be cited.
  • Aryl having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred.
  • Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl and the like.
  • R 1 to R 4 are each independently hydrogen, alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons or aryl having 6 to 20 carbons, and the above formula (ETM-5-1) The explanation in can be cited.
  • anthracene derivatives can be produced using known raw materials and known synthesis methods.
  • the benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).
  • Ar 1 is independently an aryl having 6 to 20 carbon atoms, and the same description as “aryl having 6 to 20 carbon atoms” in the above formula (ETM-5-1) can be cited.
  • Aryl having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred.
  • Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl and the like.
  • Ar 2 is independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). And two Ar 2 may be bonded to form a ring.
  • Alkyl in Ar 2 may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms.
  • Preferred “alkyl” is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferable “alkyl” is alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons). More preferable “alkyl” is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred “alkyl” is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).
  • alkyl examples 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 and the like.
  • cycloalkyl in Ar 2 examples include cycloalkyl having 3 to 12 carbon atoms. Preferred “cycloalkyl” is cycloalkyl having 3 to 10 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 3 to 8 carbon atoms. More preferred “cycloalkyl” is cycloalkyl having 3 to 6 carbon atoms. Specific examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.
  • aryl in Ar 2 , preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred is aryl having 6 to 14 carbon atoms, Preferred is aryl having 6 to 12 carbon atoms.
  • aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl and the like.
  • Two Ar 2 may be bonded to form a ring.
  • cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene is spiro-bonded to the 5-membered ring of the fluorene skeleton. May be.
  • This benzofluorene derivative can be produced using a known raw material and a known synthesis method.
  • the phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013/079217.
  • R 5 is substituted or unsubstituted alkyl having 1 to 20 carbons, cycloalkyl having 3 to 20 carbons, aryl having 6 to 20 carbons or heteroaryl having 5 to 20 carbons;
  • R 6 is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or 5 to 5 carbon atoms.
  • R 7 and R 8 are each independently substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms;
  • R 9 is oxygen or sulfur;
  • j is 0 or 1
  • k is 0 or 1
  • r is an integer of 0 to 4, and
  • q is an integer of 1 to 3.
  • substituent when substituted include aryl, heteroaryl, alkyl, and cycloalkyl.
  • the phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).
  • R 1 to R 3 may be the same or different and are hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, cycloalkylthio group, aryl ether group , Arylthioether group, aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, amino group, nitro group, silyl group, and a condensed ring formed between adjacent substituents Chosen from.
  • Ar 1 may be the same or different and is an arylene group or a heteroarylene group.
  • Ar 2 may be the same or different and is an aryl group or a heteroaryl group. However, at least one of Ar 1 and Ar 2 has a substituent, or forms a condensed ring with an adjacent substituent.
  • n is an integer of 0 to 3. When n is 0, there is no unsaturated structure, and when n is 3, R 1 does not exist.
  • the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted.
  • the substituent in the case of being substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group, and this point is common to the following description.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.
  • cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl and the like, which may be unsubstituted or substituted.
  • the number of carbon atoms in the alkyl group moiety is not particularly limited, but is usually in the range of 3-20.
  • the aralkyl group refers to an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon are unsubstituted or substituted. It doesn't matter.
  • the number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually in the range of 1-20.
  • the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, which may be unsubstituted or substituted.
  • the number of carbon atoms of the alkenyl group is not particularly limited, but is usually in the range of 2-20.
  • the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. It doesn't matter.
  • the alkynyl group represents an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted.
  • the number of carbon atoms of the alkynyl group is not particularly limited, but is usually in the range of 2-20.
  • the alkoxy group represents an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is usually in the range of 1-20.
  • the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
  • the cycloalkylthio group is a group in which an oxygen atom of an ether bond of a cycloalkoxy group is substituted with a sulfur atom.
  • aryl ether group refers to an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted.
  • the number of carbon atoms of the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.
  • the aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom.
  • the aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group.
  • the aryl group may be unsubstituted or substituted.
  • the number of carbon atoms of the aryl group is not particularly limited, but is usually in the range of 6 to 40.
  • the heterocyclic group refers to, for example, a cyclic structural group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, or a carbazolyl group, which is unsubstituted or substituted. It doesn't matter.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is usually in the range of 2-30.
  • Halogen means fluorine, chlorine, bromine and iodine.
  • aldehyde group, carbonyl group, and amino group can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic rings, and the like.
  • aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocyclic ring may be unsubstituted or substituted.
  • the silyl group refers to, for example, a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted.
  • the carbon number of the silyl group is not particularly limited, but is usually in the range of 3-20.
  • the number of silicon is usually 1-6.
  • the condensed ring formed between adjacent substituents includes, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and A conjugated or non-conjugated fused ring formed between Ar 2 and the like.
  • n when n is 1, it may be formed conjugated or non-conjugated fused ring with two of R 1 each other.
  • These condensed rings may contain a nitrogen, oxygen, or sulfur atom in the ring structure, or may be further condensed with another ring.
  • phosphine oxide derivative examples include the following.
  • This phosphine oxide derivative can be produced using a known raw material and a known synthesis method.
  • the pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011/021689.
  • Ar is each independently an optionally substituted aryl or an optionally substituted heteroaryl.
  • n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.
  • aryl in “optionally substituted aryl” include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, More preferred is aryl having 6 to 12 carbon atoms.
  • aryl include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl.
  • Terphenylyl which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, o-terpheny
  • Heteroaryl of “optionally substituted heteroaryl” includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbons is more preferred, and heteroaryl having 2 to 10 carbons is particularly preferred. Examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring constituent atoms.
  • heteroaryl includes, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naph
  • the aryl and heteroaryl may be substituted, and may be substituted with, for example, the aryl or heteroaryl.
  • this pyrimidine derivative include the following.
  • This pyrimidine derivative can be produced using a known raw material and a known synthesis method.
  • the carbazole derivative is, for example, a compound represented by the following formula (ETM-9) or a multimer in which a plurality of such carbazole derivatives are bonded by a single bond or the like. Details are described in US Publication No. 2014/0197386.
  • Ar is each independently an optionally substituted aryl or an optionally substituted heteroaryl.
  • n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.
  • aryl in “optionally substituted aryl” include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, More preferred is aryl having 6 to 12 carbon atoms.
  • aryl include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl.
  • Terphenylyl which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, o-terpheny
  • Heteroaryl of “optionally substituted heteroaryl” includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbons is more preferred, and heteroaryl having 2 to 10 carbons is particularly preferred. Examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring constituent atoms.
  • heteroaryl includes, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naph
  • the aryl and heteroaryl may be substituted, and may be substituted with, for example, the aryl or heteroaryl.
  • the carbazole derivative may be a multimer in which a plurality of compounds represented by the above formula (ETM-9) are bonded by a single bond or the like.
  • an aryl ring preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring
  • an aryl ring preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring
  • carbazole derivative examples include the following.
  • This carbazole derivative can be produced using a known raw material and a known synthesis method.
  • the triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Details are described in US Publication No. 2011/0156013.
  • Ar is each independently an optionally substituted aryl or an optionally substituted heteroaryl.
  • n is an integer of 1 to 3, preferably 2 or 3.
  • aryl in “optionally substituted aryl” include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, More preferred is aryl having 6 to 12 carbon atoms.
  • aryl include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl.
  • Terphenylyl which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, o-terpheny
  • Heteroaryl of “optionally substituted heteroaryl” includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbons is more preferred, and heteroaryl having 2 to 10 carbons is particularly preferred. Examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring constituent atoms.
  • heteroaryl includes, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, benzo [b] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naph
  • the aryl and heteroaryl may be substituted, and may be substituted with, for example, the aryl or heteroaryl.
  • triazine derivative examples include the following.
  • This triazine derivative can be produced using a known raw material and a known synthesis method.
  • the benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).
  • ⁇ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4
  • the “benzimidazole substituent” means that the pyridyl group in the “pyridine substituent” in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is benzo It is a group replaced with an imidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium.
  • R 11 in the benzimidazole group is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms, and the above formula (ETM-2-1) and the formula ( The description of R 11 in ETM-2-2) can be cited.
  • ⁇ is preferably an anthracene ring or a fluorene ring.
  • the structure of the above formula (ETM-2-1) or formula (ETM-2-2) can be cited, Among them, R 11 to R 18 can be referred to the description of the above formula (ETM-2-1) or formula (ETM-2-2). Further, in the above formula (ETM-2-1) or formula (ETM-2-2), it is explained in a form in which two pyridine-based substituents are bonded.
  • this benzimidazole derivative include, for example, 1-phenyl-2- (4- (10-phenylanthracen-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- ( Naphthalen-2-yl) anthracen-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalen-2-yl) anthracen-9-yl) -1,2-diphenyl-1H-benzo [d] imidazole, 1- (4 -(10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10 Di (naphthalen-2
  • This benzimidazole derivative can be produced using a known raw material and a known synthesis method.
  • the phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006/021982.
  • ⁇ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4 is there.
  • R 11 to R 18 in each formula are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably carbon (Aryl of formula 6 to 30).
  • alkyl preferably alkyl having 1 to 24 carbon atoms
  • cycloalkyl preferably cycloalkyl having 3 to 12 carbon atoms
  • aryl preferably carbon (Aryl of formula 6 to 30).
  • any of R 11 to R 18 is bonded to ⁇ which is an aryl ring.
  • At least one hydrogen in each phenanthroline derivative may be replaced with deuterium.
  • Alkyl in R 11 ⁇ R 18, cycloalkyl and aryl may be cited to the description of R 11 ⁇ R 18 in the formula (ETM-2).
  • ⁇ includes the following structural formula, for example.
  • each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl.
  • this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10- Phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9 ′ -Difluoro-bi (1,10-phenanthroline-5-yl), bathocuproin, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene and the like.
  • This phenanthroline derivative can be produced using a known raw material and a known synthesis method.
  • the quinolinol-based metal complex is, for example, a compound represented by the following general formula (ETM-13).
  • R 1 to R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl
  • M is Li, Al, Ga, Be or Zn
  • n is an integer of 1 to 3.
  • quinolinol metal complexes include 8-quinolinol lithium, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris (3 , 4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) ( Phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolato) aluminum, bis (2-methyl-8- Quinolinolato) (4- Tylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolate)
  • This quinolinol-based metal complex can be produced using a known raw material and a known synthesis method.
  • the thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).
  • the benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).
  • ⁇ in each formula is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4
  • the “thiazole-based substituent” and “benzothiazole-based substituent” are “pyridine-based” in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2).
  • the pyridyl group in the “substituent” is a group in which a thiazole group or a benzothiazole group is replaced, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with deuterium.
  • ⁇ is preferably an anthracene ring or a fluorene ring.
  • the structure of the above formula (ETM-2-1) or formula (ETM-2-2) can be cited, Among them, R 11 to R 18 can be referred to the description of the above formula (ETM-2-1) or formula (ETM-2-2).
  • R 11 to R 18 can be referred to the description of the above formula (ETM-2-1) or formula (ETM-2-2).
  • it is described in the form of two pyridine-based substituents bonded to each other, but these are represented by thiazole-based substituents (or benzothiazole-based substituents).
  • at least one of R 11 to R 18 in the above formula (ETM-2-1) is replaced with a thiazole substituent (or benzothiazole substituent) to replace the “pyridine substituent” with R 11 to R 18. May be replaced.
  • thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.
  • the electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer.
  • a substance capable of reducing the material forming the electron transport layer or the electron injection layer various substances can be used as long as they have a certain reducing ability.
  • alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkalis From the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one selected can be suitably used.
  • Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2. 9eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and alkaline earth metals such as those having a work function of 2.9 eV or less are particularly preferable.
  • a more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs.
  • alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL element can be improved and the lifetime can be extended.
  • a reducing substance having a work function of 2.9 eV or less a combination of two or more alkali metals is also preferable.
  • a combination containing Cs such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
  • Cs such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
  • the cathode 108 in the organic electroluminescence device plays a role of injecting electrons into the light emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.
  • the material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used.
  • metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or alloys thereof (magnesium-silver alloy, magnesium -Indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum) are preferred.
  • Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics.
  • metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride Lamination of hydrocarbon polymer compounds and the like is a preferred example.
  • the method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.
  • the material used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer which is equal to or higher than the binder that may be used in each layer, can form each layer alone.
  • each layer constituting the organic EL element is formed by vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method or casting method.
  • the thin film can be formed by a method such as a coating method.
  • the film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like.
  • the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, and the like.
  • Deposition conditions generally include boat heating temperature +50 to + 400 ° C., vacuum degree 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / second, substrate temperature ⁇ 150 to + 300 ° C., film thickness 2 nm to 5 ⁇ m. It is preferable to set appropriately within the range.
  • an organic EL element composed of an anode / hole injection layer / hole transport layer / a light emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode
  • a manufacturing method of will be described.
  • a thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode.
  • a host material and a dopant material are co-evaporated to form a thin film to form a light emitting layer.
  • An electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by vapor deposition. By forming it as a cathode, a target organic EL element can be obtained.
  • the production order can be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order. It is.
  • the anode When a DC voltage is applied to the organic EL device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Luminescence can be observed from the side (anode or cathode, and both).
  • the organic EL element also emits light when a pulse current or an alternating current is applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the present invention can also be applied to a display device provided with an organic EL element or a lighting device provided with an organic EL element.
  • the display device or lighting device including the organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment and a known driving device, such as DC driving, pulse driving, or AC driving. It can drive using a well-known drive method suitably.
  • Examples of the display device include a panel display such as a color flat panel display, and a flexible display such as a flexible color organic electroluminescence (EL) display (for example, JP-A-10-335066 and JP-A-2003-321546). Gazette, JP-A-2004-281086, etc.).
  • Examples of the display method of the display include a matrix and / or segment method. Note that the matrix display and the segment display may coexist in the same panel.
  • pixels for display are two-dimensionally arranged such as a grid or a mosaic, and characters and images are displayed by a set of pixels.
  • the shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 ⁇ m or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become.
  • monochrome display pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type.
  • the matrix driving method may be either a line sequential driving method or an active matrix.
  • the line-sequential driving has an advantage that the structure is simple. However, the active matrix may be superior in consideration of the operation characteristics, so that it is necessary to properly use it depending on the application.
  • a pattern is formed so as to display predetermined information, and a predetermined region is caused to emit light.
  • a predetermined region is caused to emit light.
  • the time and temperature display in a digital clock or a thermometer the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned.
  • the illuminating device examples include an illuminating device such as a room illuminator, a backlight of a liquid crystal display device, and the like (for example, Japanese Patent Laid-Open Nos. 2003-257621, 2003-277741, and 2004-119211). Etc.)
  • the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like.
  • the backlight using the light emitting element according to the present invention is thin and lightweight.
  • o-Tolylboronic acid (2.65 g, 22 mmol), tetrakis (triphenylphosphine) palladium (0) (1.16 g, 1.0 mmol), potassium carbonate (9.67 g, 70 mmol) and ethanol (71 ml) in a nitrogen atmosphere
  • 3-bromophenol (3.50 g, 20 mmol) was added, and the mixture was stirred with heating at 60 ° C. for 18 hours.
  • the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, 1N hydrochloric acid (45 ml) was added at room temperature, the aqueous layer was extracted three times with toluene, and then the solvent was distilled off under reduced pressure.
  • the obtained solid was dissolved in toluene (100 mL), acetic acid (3.00 mL, 52 mmol) was added, and the mixture was stirred with heating at 90 ° C. for 26 hr.
  • reaction solution was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (100 mL) was added at room temperature, the aqueous layer was extracted three times with toluene, and the solvent was evaporated under reduced pressure.
  • the obtained crude product was purified by sublimation (250 ° C., 8.9 ⁇ 10 ⁇ 4 Pa), whereby 1,3,5-tris ([1,1′-biphenyl] -3-yloxy) benzene was converted into yellow Obtained as a solid (2.07 g, 71% yield).
  • 1,2,4-trichlorobenzene (4.0 mL) was added at room temperature, and the mixture was heated and stirred at 200 ° C. for 12 hours.
  • the reaction solvent was cooled to room temperature, and hydrogen iodide in the reaction solvent was distilled off under reduced pressure. Thereafter, N, N-diisopropylethylamine (0.105 mL, 0.60 mmol) was added at room temperature, and the solvent was distilled off.
  • o-Tolylboronic acid (67.9 g, 0.500 mol), tetrakis (triphenylphosphine) palladium (0) (2.89 g, 2.51 mmol), potassium carbonate (242.1 g, 1.75 mol), and ethanol (520 ml) )
  • 4-bromophenol (87.0 g, 0.500 mol) under a nitrogen atmosphere, and the mixture was heated and stirred at 60 ° C. for 41 hours.
  • the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, 6N hydrochloric acid (1.0 L) was added at room temperature, the aqueous layer was extracted three times with toluene, and then the solvent was distilled off under reduced pressure.
  • the obtained crude product was washed with hexane to obtain 2′-methyl- [1,1′-biphenyl] -3-ol as a brown solid (75.0 g, yield 81%). .
  • HI is N, N′-diphenyl-N, N′-dinaphthyl-4,4′-diaminobiphenyl and “HT” is 4,4 ′, 4 ”-tris (N-carbazolyl) Triphenylamine
  • EB is 1,3-bis (N-carbazolyl) benzene
  • E-H is 3,3′-bis (N-carbazolyl) -1,1′-biphenyl
  • ET is diphenyl [4- (triphenylsilyl) phenyl] phosphine oxide.
  • Example 1 A glass substrate (manufactured by Opto Science Co., Ltd.) of 26 mm ⁇ 28 mm ⁇ 0.7 mm obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 50 nm was used as a transparent support substrate.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, HT, EB, compound (A-201), compound (B3-2676), compound ET and LiF are placed therein.
  • a molybdenum vapor deposition boat and a tungsten vapor deposition boat containing aluminum were mounted.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the vacuum chamber was depressurized to 5 ⁇ 10 ⁇ 4 Pa, and first, HI was heated and evaporated to a film thickness of 40 nm to form a hole injection layer. Next, HT was heated and evaporated to a thickness of 15 nm to form a hole transport layer. Next, the electron blocking layer was formed by heating and depositing EB to a thickness of 15 nm. Next, the compound (A-201) and the compound (B3-2676) were heated at the same time and evaporated to a thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of the compound (A-201) and the compound (B3-2676) was approximately 98 to 2.
  • ET was heated and evaporated to a film thickness of 40 nm to form an electron transport layer.
  • LiF is heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm, and then aluminum is heated to deposit to a film thickness of 100 nm to form a cathode.
  • an organic EL element was obtained.
  • a direct current voltage was applied with the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, and the characteristics at 100 cd / m 2 emission were measured.
  • Example 2 and Comparative Example 1 An organic EL device was prepared according to Example 1 except that the host material and the dopant material were those described in Table 1A, and the characteristics at 100 cd / m 2 emission were measured.
  • the structure of the compound used as the host and dopant of the light emitting layer is as follows.
  • Example 3 A glass substrate (manufactured by Optoscience Co., Ltd.) of 26 mm ⁇ 28 mm ⁇ 0.7 mm obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm was used as a transparent support substrate.
  • This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and HI, HT, EB, compound (A-226), compound (B3-3001), and ET were put therein.
  • a tantalum vapor deposition boat and an aluminum nitride vapor deposition boat each containing LiF and aluminum were mounted.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the vacuum chamber is depressurized to 5 ⁇ 10 ⁇ 4 Pa, and first, HI is heated and evaporated to a film thickness of 40 nm, and then HT is heated and evaporated to a film thickness of 15 nm to form holes. An injection layer and a hole transport layer were formed respectively.
  • the electron blocking layer was formed by heating and depositing EB to a thickness of 15 nm.
  • the compound (A-226) and the compound (B3-3001) were heated at the same time and evaporated to a thickness of 20 nm to form a light emitting layer.
  • the deposition rate was adjusted so that the weight ratio of the compound (A-226) and the compound (B3-3001) was 99: 1.
  • ET was heated and evaporated to a film thickness of 30 nm to form an electron transport layer.
  • the deposition rate of each layer was set to 0.01 to 1 nm / second.
  • LiF is heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm, and then aluminum is heated to deposit to a film thickness of 100 nm to form a cathode.
  • an organic EL element was obtained.
  • the deposition rate of aluminum was adjusted to 1 to 10 nm / second.
  • the emission spectrum had a peak wavelength of 469 nm, and deep blue emission was observed.
  • the external quantum efficiency at the time of light emission of 100 cd / m 2 was 29.1%, and a high quantum efficiency was obtained.
  • Example 4 An organic EL device was obtained by the same procedure and configuration as in Example 3 except that the host was changed to compound (A-3232).
  • a direct current voltage was applied using an ITO electrode as an anode and a LiF / aluminum electrode as a cathode and characteristics at 100 cd / m 2 emission were measured, the emission spectrum had a peak wavelength of 469 nm, and deep blue emission was observed.
  • the external quantum efficiency at the time of light emission of 100 cd / m 2 was 28.8%, and a high quantum efficiency was obtained.
  • TAF-OLED Element A TAF-OLED element was produced, and current density, luminance, chromaticity and external quantum efficiency were measured.
  • the configuration shown in Table 3 was selected and evaluated as the configuration of the manufactured TAF-OLED element.
  • This configuration is a configuration suitable for a thermally activated delayed fluorescence material, and is an element configuration that can be expected to have high efficiency as described in the literature (Adv. Mater. 2016, 28, 2777-2781).
  • application of the compound of the present invention is not limited to these structures, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compound of the present invention.
  • Example 5 A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm ⁇ 28 mm ⁇ 0.7 mm obtained by polishing ITO deposited to a thickness of 200 nm by sputtering to 50 nm is used as a transparent support substrate.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and HI, HT, EB, Compound (A-226), Compound (2PXZ-TAZ), Compound (B3-3001) And a tantalum vapor deposition boat each containing ET, and an aluminum nitride vapor deposition boat each containing LiF and aluminum.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the vacuum chamber is depressurized to 5 ⁇ 10 ⁇ 4 Pa, first, HI is heated and evaporated to a film thickness of 40 nm, and then HT is heated and evaporated to a film thickness of 15 nm to form two layers. A hole layer made of is formed. Next, the electron blocking layer is formed by heating and depositing EB so as to have a film thickness of 15 nm.
  • the compound (A-226) as a host, the compound (2PXZ-TAZ) as an assisting dopant, and the compound (B3-3001) as an emitting dopant are simultaneously heated to co-evaporate to a thickness of 20 nm to emit light. Form a layer.
  • the deposition rate is adjusted so that the weight ratio of host, assisting dopant and emitting dopant is approximately 90 to 9 to 1.
  • ET is heated and evaporated to a film thickness of 30 nm to form an electron transport layer.
  • the deposition rate of each of the above layers is set to 0.01 to 1 nm / second.
  • LiF is heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm, and then aluminum is heated to deposit to a film thickness of 100 nm to form a cathode.
  • the aluminum deposition rate is adjusted to 1 to 10 nm / second.
  • a high-efficiency TAF-OLED element that emits deep blue light can be obtained by applying a DC voltage using an ITO electrode as an anode and a LiF / aluminum electrode as a cathode.
  • the organic EL characteristics such as the light emission characteristics can be further enhanced by the polycyclic aromatic compound represented by the formula (A), which has not been specifically known conventionally, and the light emitting layer.
  • the choice of materials can be increased.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Theoretical Computer Science (AREA)
  • Electroluminescent Light Sources (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)

Abstract

Le problème décrit dans le cadre de la présente invention est de fournir un élément électroluminescent organique ayant des propriétés d'électroluminescence organique exceptionnelles, y compris des propriétés d'émission de lumière. À cet effet, la présente invention porte sur un élément électroluminescent à effet de champ organique qui comprend une couche électroluminescente comprenant : en tant que premier composant, au moins un multimère d'un composé aromatique polycyclique qui comporte un composé aromatique polycyclique représenté par la formule générale (A) et une pluralité de structures représentées par la formule générale (A) ; et, en tant que second composant, au moins un composé ayant une énergie de triplet (ET) comprise entre 2,2 et 3,0 eV. (Dans la formule générale (A) : X représente B (bore) ou similaire ; R1–R11 représentent l'hydrogène, un aryle pouvant être substitué, un hétéroaryle, ou analogue, à condition qu'au moins l'un de R2, R5, R7, R8 et R10 soit un groupe représenté par-O-W, W étant un aryle ou un hétéroaryle ; au moins un hydrogène parmi ceux-ci peut être substitué par un aryle, un hétéroaryle, un diarylamino ou un alkyle ; et au moins un hydrogène dans le composé représenté par la formule (A) peut être substitué par un halogène ou du deutérium).
PCT/JP2019/002866 2018-02-05 2019-01-29 Élément électroluminescent à effet de champ organique utilisant un matériau électroluminescent de composé aromatique polycyclique WO2019151204A1 (fr)

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CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
WO2020040298A1 (fr) * 2018-08-23 2020-02-27 学校法人関西学院 Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage, composition de formation de couche luminescente et composé
WO2020045681A1 (fr) * 2018-08-31 2020-03-05 学校法人関西学院 Élément électroluminescent organique utilisant un matériau électroluminescent constitué d'un composé aromatique polycyclique
WO2020101001A1 (fr) * 2018-11-15 2020-05-22 学校法人関西学院 Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage
US20210273175A1 (en) * 2020-02-19 2021-09-02 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
WO2022084505A1 (fr) * 2020-10-23 2022-04-28 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques

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Publication number Priority date Publication date Assignee Title
WO2020040298A1 (fr) * 2018-08-23 2020-02-27 学校法人関西学院 Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage, composition de formation de couche luminescente et composé
JPWO2020040298A1 (ja) * 2018-08-23 2021-09-24 学校法人関西学院 有機電界発光素子、表示装置、照明装置、発光層形成用組成物、および化合物
JP7388658B2 (ja) 2018-08-23 2023-11-29 学校法人関西学院 有機電界発光素子、表示装置、照明装置、発光層形成用組成物、および化合物
WO2020045681A1 (fr) * 2018-08-31 2020-03-05 学校法人関西学院 Élément électroluminescent organique utilisant un matériau électroluminescent constitué d'un composé aromatique polycyclique
WO2020101001A1 (fr) * 2018-11-15 2020-05-22 学校法人関西学院 Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
US20210273175A1 (en) * 2020-02-19 2021-09-02 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
US11800793B2 (en) * 2020-02-19 2023-10-24 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
WO2022084505A1 (fr) * 2020-10-23 2022-04-28 Cynora Gmbh Molécules organiques pour dispositifs optoélectroniques

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