WO2020054676A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2020054676A1
WO2020054676A1 PCT/JP2019/035408 JP2019035408W WO2020054676A1 WO 2020054676 A1 WO2020054676 A1 WO 2020054676A1 JP 2019035408 W JP2019035408 W JP 2019035408W WO 2020054676 A1 WO2020054676 A1 WO 2020054676A1
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ring
substituted
aryl
alkyl
cycloalkyl
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PCT/JP2019/035408
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English (en)
Japanese (ja)
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琢次 畠山
瑛治 清水
国防 王
詠希 町田
笹田　康幸
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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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

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  • the present invention relates to an organic electroluminescence device, a display device and a lighting device using the same.
  • the organic EL element has a structure including a pair of electrodes including an anode and a cathode, and one or more 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-based compound has been developed (WO 2004/061047).
  • a hole transport material for example, a triphenylamine-based compound has been developed (Japanese Patent Application Laid-Open No. 2001-172232).
  • an anthracene-based compound has been developed (Japanese Patent Application Laid-Open No. 2005-170911).
  • the charge transporting property of a NO-linked compound (compound 1 on page 63) is evaluated, but there is no description of a method for producing a material other than the NO-linked compound, and the linking element is If different, the electronic state of the entire compound is different, and thus characteristics obtained from materials other than the NO-linked compound are not yet known.
  • Other examples of such compounds can be found (WO 2011/107186).
  • a compound having a conjugated structure in which the energy (T1) of triplet excitons is large can emit phosphorescence of a shorter wavelength, and thus is useful as a material for a blue light-emitting layer.
  • polycyclic An organic EL device comprising at least one of an aromatic compound
  • a light-emitting layer containing an anthracene compound between a pair of electrodes to form an organic EL device has been completed.
  • the chemical structure and the substituent may be represented by the number of carbon atoms.However, when the chemical structure is substituted with a substituent, or when the substituent is further substituted with a substituent, the number of carbon atoms is represented by the chemical structure And the carbon number of each substituent, and does not mean the total carbon number of the chemical structure and the substituent or the total carbon number of the substituent and the substituent.
  • “substituent B having carbon number Y substituted with substituent A having carbon number X” means that “substituent A having carbon number X” is substituted for “substituent B having carbon number Y”. However, the carbon number Y is not the total carbon number of the substituent A and the substituent B.
  • the substituent B having the number of carbon atoms Y substituted with the substituent A means that the “substituent A (there is no limitation on the number of carbon atoms)” replaces the “substituent B having the number of carbon atoms 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 including an anode and a cathode and a light emitting layer disposed between the pair of electrodes, wherein the light emitting layer is a polycyclic aromatic compound represented by the following general formula (1).
  • An organic electroluminescent device comprising: an aromatic compound; and at least one polymer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1); and an anthracene compound.
  • 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;
  • Y 1 is B,
  • X 1 and X 2 are each independently> O or> NR, wherein R of the above> NR is an optionally substituted aryl, an optionally substituted heteroaryl, a substituted Or an optionally substituted cycloalkyl, and R in> NR is bonded to at least one of the rings A, B and C via a linking group or a single bond. May be doing, and At least one hydrogen in the compound or structure represented by the formula (1) may be substituted with halogen or deuterium.
  • Ring A, ring B and ring C are each independently an aryl ring or a 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 diarylboryl (where two aryls are connected via a single bond or a linking group ), Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy, and these rings are represented by Y 1 , A 5-membered ring sharing a bond with the fused bicyclic structure at the center of the above formula
  • the a ring may also be at least one bond of ring B and ring C, wherein -C (-R) 2 - of R is hydrogen, alkyl or cycloalkyl Yes, At least one hydrogen in the compound or structure represented by the formula (1) may be substituted with halogen or deuterium, and In the case of a multimer, it is a dimer or trimer having two or three structures represented by the formula (1).
  • Item 2 The organic electroluminescent device according to Item 1.
  • the polycyclic aromatic compound and a multimer thereof are a polycyclic aromatic compound represented by the following general formula (2) and a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2) Item 2.
  • Y 1 is B
  • X 1 and X 2 are each independently> O or> NR, wherein R in the> NR is alkyl, cycloalkyl, diarylamino or diarylboryl (the two aryls are a single bond or a linked Aryl, alkyl, cycloalkyl, diarylamino, or diarylboryl (optionally substituted with a group) having 6 to 12 carbon atoms (the two aryls may be bonded via
  • R of —C (—R) 2 — is alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons; At least one hydrogen in the compound represented by the formula (2) may be replaced by halogen or deuterium.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently hydrogen, aryl having 6 to 30 carbons, carbon, A heteroaryl having 2 to 30 carbon atoms, a diarylamino (where each aryl is an aryl having 6 to 12 carbon atoms) or a diarylboryl (where each aryl is an aryl having 6 to 12 carbon atoms, and the two aryls are a single bond or And an adjacent ring among R 1 to R 11 may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms together with ring a, ring b or ring c.
  • a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one hydrogen in the formed ring is a diarylamino (where each aryl is an aryl having 6 to 12 carbon atoms) or a diarylamino group.
  • Ruboriru (where each aryl is aryl of 6 to 12 carbon atoms, the two aryl linked via a single bond or a linking group may be) may be substituted with, X 1 and X 2 each independently represent> O or> NR (where R of the NR is alkyl, cycloalkyl, diarylamino or diarylboryl (two aryls are a single bond or a linking group)
  • R of the NR is alkyl, cycloalkyl, diarylamino or diarylboryl (two aryls are a single bond or a linking group)
  • Aryl having 6 to 10 carbon atoms which may be substituted with At least one hydrogen in the compound represented by the formula (2) may be substituted with halogen or deuterium;
  • Item 4 The organic electroluminescent device according to item 3.
  • Item 5 The organic electroluminescent device according to any one of Items 1 to 4, wherein the polycyclic aromatic compound and a multimer thereof have at least one deuterium.
  • Item 6 In the polycyclic aromatic compound and its multimer, the ratio of deuterium to the total number of 100% of hydrogen and deuterium bonded to carbon constituting the aromatic ring in one molecule is 10 to 100%. 6.
  • Item 7. In the polycyclic aromatic compound and the multimer thereof, the ratio of deuterium to 100% of the total number of hydrogen and deuterium bonded to carbon constituting the aromatic ring in one molecule is 100%.
  • Item 8 The organic electroluminescent device according to item 1, wherein the polycyclic aromatic compound and a multimer thereof are compounds having a structure represented by any of the following. (In the above structural formulas, “Me” represents methyl, “tBu” represents t-butyl, “tAm” represents t-amyl, and “D” represents deuterium.)
  • Item 9 The organic electroluminescent device according to any one of Items 1 to 8, wherein the anthracene compound is a compound represented by the following general formula (3).
  • L is a single bond, arylene having 6 to 18 carbon atoms, or alkylene having 1 to 10 carbon atoms, and at least one hydrogen in the arylene and the alkylene is substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • Ar 4 is each independently silyl substituted with a group selected from hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, alkyl having 1 to 4 carbons and cycloalkyl having 5 to 10 carbons, n is 0 or 1
  • X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3); * In the above formula (3-X1), formula (3-X2) or formula (3-X3) indicates a bonding position to the 9th or 10th position of the anthracene ring in the formula (3)
  • Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, carbazolyl, benzocarbazolyl, or Ph
  • Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, carbazolyl, benzocarbazolyl, phenyl-substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthofuran Benzofuranyl, benzothiophenyl, dibenzothiophenyl or naphthobenzothiophenyl, and at least one hydrogen in these groups further includes alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkyl Or cycloalkyl-substituted or unsubstituted phenyl,
  • Item 10 The group represented by the formula (3-X3) is phenyl, phenanthryl, a group represented by the following formula (3-X3-1) or a group represented by the following formula (3-X3-2); Item 10.
  • Ar 5 is independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, benzofuranyl, naphthobenzofuranyl, It is benzothiophenyl or naphthobenzothiophenyl, and at least one hydrogen thereof may be further substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons. )
  • Item 11 The organic electroluminescent device according to any one of items 1 to 10, wherein the anthracene compound is a compound represented by the following general formula (3-1-X).
  • ⁇ is phenyl, naphthyl, phenanthryl or triphenylenyl, which is bonded to phenyl and is optionally substituted with Ar 1 and R,
  • Ar is an optionally substituted aryl; n is 1 or 2; when n is 1, Ar is bonded to either the x-position or y-position; when n is 2, Ar is at the x-position; And the structure may be the same or different by bonding to both the y-position, Ar 1 is an optionally substituted aryl; m is an integer that can be substituted at maximum from 0 to ⁇ ; and when m is 2 or more, the structures of Ar 1 may be the same or different.
  • R is each independently alkyl or cycloalkyl
  • a is an integer of 0 to 5
  • b is an integer of 0 to 3
  • b + n is 4 or less
  • c is 0 to ⁇ .
  • a possible integer, where c + m is less than or equal to the maximum substitutable for ⁇ , d is an integer from 0 to 4, and At least one hydrogen in the compound represented by the formula (3-1-X) may be substituted with deuterium.
  • Item 12. The organic electroluminescent device according to item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X1).
  • Ar is an optionally substituted aryl
  • n is 1 or 2
  • the structure may be the same or different by bonding to both the y-position
  • Ar 1 is an aryl which may be substituted
  • m is an integer of 0 to 5, and when m is 2 or more, the structures of Ar 1 may be the same or different
  • R is each independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is 4 or less, c is an integer of 0 to 5, Where c + m is 5 or less, d is an integer from 0 to 4, and At least one hydrogen in the compound represented
  • Item 13 The organic electroluminescent device according to item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X2).
  • the naphthalene ring represented by the formula (3-1-X2) is 1-naphthyl or 2-naphthyl bonded to phenyl, Ar is an optionally substituted aryl; n is 1 or 2; when n is 1, Ar is bonded to either the x-position or y-position; when n is 2, Ar is at the x-position; And the structure may be the same or different by bonding to both the y-position, Ar 1 is an optionally substituted aryl, m is an integer of 0 to 7, and when m is 2 or more, the structures of Ar 1 may be the same or different, R is each independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is 4
  • Item 14 The organic electroluminescent device according to item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X3).
  • the phenanthrene ring represented by the formula (3-1-X3) is 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl or 9-phenanthryl, which is bonded to phenyl;
  • Ar is an optionally substituted aryl; n is 1 or 2; when n is 1, Ar is bonded to either the x-position or y-position; when n is 2, Ar is at the x-position;
  • the structure may be the same or different by bonding to both the y-position,
  • Ar 1 is an optionally substituted aryl, m is an integer of 0 to 9, and when m is 2 or more, the structures of Ar 1 may be the same or different;
  • R is each independently alkyl or cycloalkyl, a is an integer of 0 to 5,
  • Item 15. The organic electroluminescent device according to item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X4).
  • the triphenylene ring represented by the formula (3-1-X4) is 1-triphenylenyl or 2-triphenylenyl bonded to phenyl; Ar is an optionally substituted aryl; n is 1 or 2; when n is 1, Ar is bonded to either the x-position or y-position; when n is 2, Ar is at the x-position; And the structure may be the same or different by bonding to both the y-position, Ar 1 is an optionally substituted aryl, m is an integer of 0 to 11, and when m is 2 or more, the structures of Ar 1 may be the same or different, R is each independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is 4 or
  • Item 16 The organic electroluminescent device according to any one of Items 1 to 15, wherein the anthracene-based compound has at least one deuterium.
  • Item 17. The organic electric field according to Item 16, wherein in the anthracene-based compound, the ratio of deuterium to the total number of hydrogen and deuterium bonded to carbon constituting the aromatic ring in one molecule is 10 to 100% with respect to 100%.
  • Item 18 The organic electroluminescent device according to item 16, wherein in the anthracene-based compound, deuterium occupies 100% of the total number of hydrogen and deuterium bonded to carbon constituting the aromatic ring in one molecule is 100%. .
  • Item 19 The organic electroluminescent device according to item 16, wherein the anthracene-based compound is a compound represented by any of the following formulas. (“D” in each of the above structural formulas represents deuterium.)
  • Item 20 The organic electroluminescent device according to any one of Items 1 to 15, wherein the anthracene-based compound is a compound represented by any of the following.
  • Item 22 Further, at least one of an electron transport layer and 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, Fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and Item 22.
  • the organic electroluminescent device according to any one of Items 1 to 21, comprising at least one selected from the group consisting of azoline derivatives.
  • At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, and an alkaline earth metal. Containing at least one selected from the group consisting of halides of rare earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals. 23. The organic electroluminescent device according to 22.
  • Item 24 A display device or a lighting device comprising the organic electroluminescent element according to any one of Items 1 to 23.
  • the organic EL device has optimal light emitting characteristics.
  • FIG. 1 is a schematic cross-sectional view illustrating an organic EL device according to an embodiment.
  • the present invention is an organic EL element having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. It includes at least one of a polycyclic aromatic compound represented by the general formula (1) and a polymer of the polycyclic aromatic compound having a plurality of structures represented by the general formula (1), and the anthracene-based compound. It is an organic EL element.
  • the light-emitting layer of the organic EL device of the present invention includes, together with an anthracene-based compound, a polycyclic aromatic compound represented by the general formula (1) and a polycyclic aromatic compound represented by the general formula (1).
  • an organic EL device having a narrow emission half width, a long lifetime, and excellent quantum efficiency can be obtained.
  • the polycyclic aromatic compound and its multimer, and the anthracene-based compound included in the light-emitting layer will be described.
  • Polycyclic Aromatic Compounds and Multimers Thereof Multimers of polycyclic aromatic compounds represented by general formula (1) and polycyclic aromatic compounds having a plurality of structures represented by general formula (1) are basically Functions as a dopant.
  • the polycyclic aromatic compound and the multimer thereof are preferably a polycyclic aromatic compound represented by the following general formula (2) or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2) It is a multimer of the compound.
  • Ring A, ring B and ring C in formula (1) 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 may be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (aryl and Amino having a heteroaryl), substituted or unsubstituted diarylboryl (the two aryls may be linked via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, Preferred is substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy.
  • substituents include aryl, heteroaryl, alkyl and cycloalkyl.
  • the aryl ring or heteroaryl ring has a bond with a central condensed bicyclic structure (hereinafter, this structure is also referred to as “D structure”) composed of Y 1 , X 1 and X 2. It preferably has a shared 5- or 6-membered ring.
  • the “condensed bicyclic structure (D structure)” is defined by the condensation of two saturated hydrocarbon rings including Y 1 , X 1 and X 2 shown in the center of the general formula (1). Means structure.
  • the “six-membered ring sharing a bond with the condensed two-ring structure” means, for example, an a-ring (benzene ring (6-membered ring)) condensed with the D structure as shown in the general formula (2).
  • the aryl ring (which is the A ring) or the heteroaryl ring has the 6-membered ring” means that the 6-membered ring alone forms the A-ring or includes the 6-membered ring.
  • aryl ring or heteroaryl ring having a 6-membered ring (A-ring)” means that the 6-membered ring constituting all or a part of the A-ring is fused to the D structure.
  • Ring A (or ring B or ring C) in general formula (1) is the same as ring a and its substituents R 1 to R 3 (or ring b and its substituents R 8 to R 11 , c) in general formula (2). Ring and its substituents R 4 to R 7 ). That is, the general formula (2) corresponds to a formula in which “A to C rings having a 6-membered ring” are selected as the A to C rings in the general formula (1). In that sense, each ring of the general formula (2) is represented by lowercase letters a to c.
  • adjacent groups among 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, the b ring or the c ring.
  • At least one hydrogen in the ring formed may be aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be a single bond or a linking group.
  • the polycyclic aromatic compound represented by the general formula (2) is obtained by the following formulas (2-1) and (2-2) depending on the mutual bonding form of the substituents on the a ring, the b ring and the c ring.
  • the ring structure constituting the compound changes.
  • the A ′ ring, B ′ ring and C ′ ring in each formula correspond to the A ring, B ring and C ring in the general formula (1), respectively.
  • the definition of each symbol is the same as the definition described above.
  • the A ′ ring, B ′ ring and C ′ ring are adjacent to each other among the substituents R 1 to R 11 as described in the general formula (2).
  • R 8 of b ring and R 7 of c ring, R 11 of b ring and R 1 of a ring, and R 1 of a ring and R 4 and R 3 of the a-ring do not correspond to “adjacent groups” and do not bond to each other. That is, “adjacent groups” means groups that are adjacent on the same ring.
  • the compound represented by the above formula (2-1) or (2-2) may be, for example, a benzene ring, an indane ring, an indole ring, a pyrrole with respect to a benzene ring which is a ring (or b ring or c ring).
  • Is a compound having an A ′ ring (or B ′ ring or C ′ ring) formed by condensing a ring, a benzofuran ring or a benzothiophene ring, and a formed condensed ring A ′ (or condensed ring B ′ or The condensed ring C ′) is a naphthalene ring, a fluorene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.
  • the compound represented by the formula (2-1A) is obtained by condensing an indane ring with both the b-ring and the c-ring benzene ring in the formula (2-1) to form a fluorene ring, It is a compound in which a group represented by -N (Ar X ) 2 is substituted on a fluorene ring.
  • the compound represented by the above formula (2-1B) has a structure in which an indane ring is condensed with only the benzene ring of ring b in the above formula (2-1) to form a fluorene ring, and further, a fluorene ring is formed.
  • R x is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group) ), Alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • R y is each independently aryl, heteroaryl, alkyl or cycloalkyl.
  • p is each independently an integer of 0 to 3.
  • R x and R y are such that when adjacent groups among R 1 to R 11 in the formula (2) are bonded to each other to form an aryl ring, the formed aryl ring is substituted. Corresponds to the above definition for the substituents obtained.
  • Ar X is each independently aryl or heteroaryl, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • Examples of the “aryl” and “heteroaryl” as Ar X include a monovalent group of “aryl ring” or “heteroaryl ring” which can be selected as A ring, B ring and C ring of general formula (1).
  • Y 1 , X 1 , X 2 , R 1 to R 8 and R 11 are the same as defined in the general formula (2), and R x , Ry and p are the same as defined in the aforementioned general formulas (2-1A) and (2-1B).
  • q is each independently an integer of 0 to 5.
  • the substituent R y of the diphenylamine structure and the substituent R y of the fluorene structure are adjacent to each other means, for example, as described below, the substituent R y adjacent to the bonding position with N (nitrogen) in Ar (phenyl).
  • R y is substituted, the substituent R y on the next bonding position to N (nitrogen) in the fluorene structure is meant a case of substituting. That is, these two substituents Ry may be bonded as follows.
  • Y 1 is B (boron), and X 1 and X 2 are each independently> O or> NR. That is, the polycyclic aromatic compound represented by the general formula (1) and a multimer thereof include the polycyclic aromatic compound represented by any of the following general formulas (1a), (1b), and (1c). It becomes a multimer. (In the above formulas (1a), (1b) and (1c), the A ring, the B ring and the C ring, and Y 1 are the same as defined in the general formula (1).)
  • the polycyclic aromatic compound represented by the general formula (2) and a multimer thereof include a polycyclic aromatic compound represented by any one of the following general formulas (2a), (2b) and (2c). It becomes a multimer.
  • R 1 to R 11 and Y 1 are the same as defined in the general formula (2).
  • R in the above —N—R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted Aryl, alkyl, cycloalkyl, diaryl which is cycloalkyl and which may be substituted by alkyl, cycloalkyl, diarylamino or diarylboryl (the two aryls may be linked via a single bond or a linking group) It is preferably a heteroaryl, alkyl or cycloalkyl optionally substituted by amino or diarylboryl (the two aryls may be linked via a single bond or a linking group).
  • R in> NR may be bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond.
  • the linking group is preferably —O—, —S— or —C (—R) 2 —.
  • R in the above-mentioned “—C (—R) 2 —” is hydrogen, alkyl or cycloalkyl.
  • R in> NR is bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond
  • R in> NR corresponds to the definition that at least one of the a, b, and c rings is bonded via a linking group or a single bond.
  • This rule can be expressed by a compound represented by the following formula (2-3-1) and having a ring structure in which X 1 and X 2 are incorporated into the condensed ring B ′ and the condensed ring C ′.
  • a B ′ ring (or a B ′ ring formed by condensing another ring so as to incorporate X 1 (or X 2 ) into the benzene ring which is the b ring (or c ring) in the general formula (2) C ′ ring).
  • the above definition has a ring structure represented by the following formula (2-3-2) or (2-3-3) in which at least one of X 1 and X 2 is incorporated into a condensed ring A ′. It can also be expressed by compounds.
  • X 1 at least one of X 1 and X 2
  • R 1 to R 11 , Y 1 , X 1 and X 2 in the formulas (2-3-1) to (2-3-3) are the same as defined in the formula (2).
  • Examples of the “aryl ring” that is ring A, ring B and ring C in formula (1) include an aryl ring having 6 to 30 carbon atoms, an aryl ring having 6 to 16 carbon atoms is preferable, and an aryl ring having 6 to 16 carbon atoms is preferable.
  • An aryl ring having 6 to 12 is more preferred, and an aryl ring having 6 to 10 carbon atoms is still more preferred.
  • the “aryl ring” is an “aryl ring formed by combining adjacent groups among R 1 to R 11 together with the a ring, b ring or c ring” defined by the general formula (2).
  • ring a (or ring b or ring c) is already composed of a benzene ring having 6 carbon atoms
  • a total of 9 carbon atoms of a condensed ring obtained by condensing a 5-membered ring with the benzene ring is the lower limit of carbon atoms. It becomes a number.
  • aryl ring examples include a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, and a tricyclic terphenyl ring (m-terphenyl, o-ring).
  • -Terphenyl, p-terphenyl condensed tricyclic, acenaphthylene, fluorene, phenalene, phenanthrene, and condensed tetracyclic triphenylene, pyrene, naphthacene, and condensed pentacyclic Examples include a perylene ring and a pentacene ring.
  • heteroaryl ring which is the ring A, ring B and ring C in the general formula (1) include a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferable. And 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, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • the “heteroaryl ring” is a heteroaryl formed by bonding adjacent groups of R 1 to R 11 defined by the general formula (2) together with a ring, b ring or c ring.
  • the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total carbon number of the condensed ring formed by condensing a 5-membered ring with the a ring (or b ring, c ring) is lower limit. Is the number of carbon atoms.
  • a pyrrole ring for example, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a 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 A, cinnoline ring, quinazoline ring, quinoxaline ring
  • At least one hydrogen in the above “aryl ring” or “heteroaryl ring” is the first substituent, substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “Diarylamino”, substituted or unsubstituted “diheteroarylamino”, substituted or unsubstituted “arylheteroarylamino”, substituted or unsubstituted “diarylboryl (two aryls are linked via a single bond or a linking group May be bonded) ", substituted or unsubstituted” alkyl ", substituted or unsubstituted” cycloalkyl ", substituted or unsubstituted” alkoxy ", or substituted or unsubstituted” aryloxy "
  • the first substituent may be an “aryl”, “heteroaryl”, or “diarylamino”.
  • aryl, heteroaryl of "diheteroarylamino", aryl and heteroaryl of "arylheteroarylamino", aryl of "diarylboryl", or aryl of "aryloxy” include the above-mentioned "aryl ring” or "aryloxy”.
  • Heteroaryl ring “includes a monovalent group.
  • alkyl as the first substituent may be either straight-chain or branched, and includes, for example, straight-chain alkyl having 1 to 24 carbons or branched-chain alkyl having 3 to 24 carbons.
  • 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 is preferable.
  • Branched alkyl having 3 to 6 carbons is more preferable, alkyl having 1 to 5 carbons (branched alkyl having 3 to 5 carbons) is particularly preferable, and alkyl having 1 to 4 carbons (3 carbons) is more preferable.
  • ⁇ 4 branched-chain alkyls ).
  • alkyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- Hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3 -Tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-dec
  • the “cycloalkyl” as the first substituent includes, for example, 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. Examples thereof include cycloalkyl and cycloalkyl having 3 to 12 carbon atoms, preferably cycloalkyl having 3 to 10 carbon atoms and 5 to 10 carbon atoms, and more preferably cycloalkyl having 3 to 8 carbon atoms and 5 to 8 carbon atoms. Further, cycloalkyl having 3 to 6 carbon atoms or 5 to 6 carbon atoms is more preferable, and cycloalkyl having 5 carbon atoms is particularly preferable.
  • Specific cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and at least one hydrogen of these groups is an alkyl having 1 to 5 carbon atoms (particularly methyl).
  • 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 or decahydroazulenyl are exemplified.
  • Alkoxy as the first substituent includes, for example, straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (alkoxy having a branched chain having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbons (alkoxy having a branched chain having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is preferable.
  • alkoxy having a branched chain having 3 to 6 carbon atoms is more preferable, alkoxy having 1 to 5 carbon atoms (alkoxy having a branched chain having 3 to 5 carbon atoms) is particularly preferable, and alkoxy having 1 to 4 carbon atoms is also preferable. (Branched alkoxy having 3 to 4 carbon atoms).
  • alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyl Oxy, n-hexyloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylhexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5 -Trimethylhexyloxy, n-decyloxy
  • aryl in the “diarylboryl” as the first substituent, the above description of aryl can be cited. Further, the two aryls may be linked via a single bond or a linking group (eg,> C (—R) 2 ,>O,> S, or> NR).
  • a linking group eg,> C (—R) 2 ,>O,> S, or> NR.
  • R of> C (—R) 2 and> NR represents aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (the above, 1 substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above is a second substituent).
  • Specific examples of these groups include Can refer to the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy as the first substituent described above.
  • Hydrogen may be substituted by a second substituent.
  • the second substituent include aryl, heteroaryl, alkyl and cycloalkyl, and specific examples thereof include the above-described monovalent group of “aryl ring” or “heteroaryl ring”; Reference may be made to the description of "alkyl” or "cycloalkyl” as a substituent of 1.
  • at least one hydrogen atom is an aryl such as phenyl (the above-described group), an alkyl such as methyl (the above-described group), or cyclohexyl.
  • a group substituted with cycloalkyl is also included in the aryl or 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 or an alkyl such as methyl or a cycloalkyl such as cyclohexyl is also a second group.
  • Heteroaryl as a substituent.
  • Examples include the monovalent group of the “aryl ring” or “heteroaryl ring” described in the general formula (1).
  • alkyl, cycloalkyl or alkoxy for R 1 to R 11 refer to the description of “alkyl”, “cycloalkyl” and “alkoxy” as the first substituent in the above description of the general formula (1). can do.
  • aryl, heteroaryl, alkyl or cycloalkyl as a substituent on these groups.
  • adjacent groups among R 1 to R 11 are bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, a heteroaryl which is a substituent on these rings , Diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, and further The same applies to aryl, heteroaryl, alkyl or cycloalkyl which is a substituent.
  • the emission wavelength can be adjusted by the steric hindrance, the electron donating property and the electron withdrawing property of the structure of the first substituent, and is preferably a group represented by the following structural formula, more preferably Is methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6- With mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy And more preferably methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, 2,6-xy
  • steric hindrance is large for selective synthesis.
  • Me represents methyl
  • tBu represents t-butyl
  • tAm represents t-amyl
  • tOct represents t-octyl
  • R of> NR in X 1 and X 2 in the general formula (1) is aryl, heteroaryl, alkyl or cycloalkyl optionally substituted with the above-mentioned second substituent, and the aryl, hetero
  • aryl, alkyl and cycloalkyl include the groups described above.
  • aryl having 6 to 10 carbon atoms such as phenyl and naphthyl
  • heteroaryl having 2 to 15 carbon atoms such as carbazolyl
  • alkyl having 1 to 5 carbon atoms such as methyl and ethyl
  • 3 to 16 carbon atoms are preferred.
  • At least one hydrogen in aryl and heteroaryl selected as R in> NR is, for example, alkyl, cycloalkyl, diarylamino or diarylboryl (two aryls are bonded through a single bond or a linking group. May be substituted.
  • alkyl, cycloalkyl, diarylamino and diarylboryl include the groups described above. This description is the same in the general formula (2) even X 1 and X 2.
  • R of the linking group “—C (—R) 2 —” in the general formula (1) is hydrogen, alkyl or cycloalkyl, and specific examples of the alkyl or cycloalkyl include the groups described above. . Particularly, alkyl having 1 to 5 carbon atoms (eg, methyl, ethyl and the like) is preferable. This description is the same for “—C (—R) 2 —” which is a linking group in the general formula (2).
  • a polymer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1), preferably a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (2) Multimers of group compounds may be included.
  • the multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer.
  • the multimer may be a form having a plurality of the above unit structures in one compound.
  • the above unit structure may be a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, or the like.
  • any of the rings (A ring, B ring or C ring, a ring, b ring or c ring) contained in the above unit structure is shared by the plurality of unit structures.
  • a ring, B ring or C ring, a ring, b ring or c ring contained in the above unit structure. May be in the form of being condensed and condensed (ring-fused multimer), but a ring-sharing multimer and a ring-fused multimer are preferable, and a ring-sharing multimer is more preferable.
  • Examples of such a multimer include the following formulas (2-4), (2-4-1), (2-4-2), (2-5-1) to (2-5) -4) or a multimeric compound represented by the formula (2-6).
  • the following formula (2-4) is a dimer compound
  • formula (2-4-1) is a dimer compound
  • formula (2-4-2) is a trimer compound
  • formula (2-5-1) is Dimer compound
  • Formula (2-5-2) is a dimer compound
  • Formula (2-5-3) is a dimer compound
  • Formula (2-5-4) is a trimer compound
  • Formula (2-5) -6) is a dimer compound.
  • the multimeric compound represented by the following formula (2-4) has a plurality of unit structures represented by the general formula (2) by sharing a benzene ring as the a ring in the general formula (2). It is a multimeric compound (ring-coupling type multimer) contained in one compound.
  • the multimeric compound represented by the following formula (2-4-1) has two units represented by the general formula (2) so as to share the benzene ring which is the a ring in the general formula (2). It is a multimeric compound having a structure in one compound (ring-sharing multimer).
  • the multimeric compound represented by the following formula (2-4-2) has three units represented by the general formula (2) by sharing the benzene ring which is the a ring in the general formula (2).
  • the multimeric compounds represented by the following formulas (2-5-1) to (2-5-4) share a benzene ring, which is the b-ring (or c-ring) in the general formula (2).
  • it is a multimeric compound (ring-sharing multimer) having a plurality of unit structures represented by the general formula (2) in one compound.
  • the multimeric compound represented by the following formula (2-6) is a compound represented by the general formula (2), for example, a benzene ring which is a ring (or a ring or c ring) of a certain unit structure and a b unit of a certain unit structure.
  • a benzene ring which is a ring (or a ring or c ring)
  • R 1 to R 11 , Y 1 , X 1 and X 2 are the same as defined in the formula (2).
  • the multimeric compound includes a multimerized form represented by the formula (2-4), the formula (2-4-1) or the formula (2-4-2) and a compound represented by the formula (2-5-1) to the formula (2-5-1). -5-4) or a multimer in combination with the multimerized form represented by the formula (2-6), and may be represented by the formulas (2-5-1) to (2-5).
  • a multimer in which the multimeric form represented by any of 4) and the multimeric form represented by formula (2-6) may be combined, may be represented by formulas (2-4) and (2).
  • the multimer may be a combination of the multimerized form represented by the formula (2-6).
  • all or a part of hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and a multimer thereof may be deuterium. That is, as in the compounds (2-2A-1) to (2-2A-248) described below, the polycyclic aromatic compound represented by the general formula (1) or (2) and its multimer are at least It may be a compound having one deuterium.
  • deuterium relative to 100% of the total number of hydrogen and deuterium bonded to carbon constituting the aromatic ring in one molecule Is preferably 10 to 100%, more preferably 30 to 100%, still more preferably 50 to 100%, still more preferably 80 to 100%, and particularly preferably 100%.
  • hydrogen and deuterium bonded to a carbon (ring-forming carbon) constituting an aromatic ring in one molecule refers to hydrogen and deuterium bonded directly to a ring-forming carbon.
  • Hydrogen and deuterium which are bonded to a ring-forming carbon through a linking atom such as carbon or nitrogen, such as hydrogen and deuterium of a substituent to be bonded are not included.
  • the number of “carbons constituting an aromatic ring in one molecule (ring-forming carbon)” is 34, of which “deuterium (D)” And 18 bonds with “methyl (Me)”, and 0 hydrogens directly bond with the ring-forming carbon.
  • At least one hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and a multimer thereof may be entirely or partially a halogen.
  • ring A, ring B, ring C where ring AC is the above-described aryl or heteroaryl ring
  • substituents on ring AC and X 1 and X 2
  • R in some> NR R is alkyl, cycloalkyl or aryl as described above
  • R is alkyl, cycloalkyl or aryl as described above
  • halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.
  • polycyclic aromatic compound examples include the following compounds.
  • “Me” is methyl
  • “Et” is ethyl
  • “tBu” is t-butyl
  • “tAm” is t-amyl
  • “D” indicates deuterium.
  • the polycyclic aromatic compound and a multimer thereof are characterized in that at least one of A ring, B ring and C ring (a ring, b ring and c ring) has phenyl at the para position to B (boron) which is Y 1.
  • B boron
  • T1 energy about 0.01 to 0.1 eV
  • At least one hydrogen in one or more phenyl or one phenylene in the compound is one or more alkyl having 1 to 5 carbon atoms, 5 to 10 carbon atoms. And more preferably a compound substituted with a cycloalkyl, preferably an alkyl having 1 to 3 carbon atoms (preferably one or more methyl), and more preferably a hydrogen (or two hydrogens) in the ortho position of one phenyl.
  • a compound in which hydrogen at the ortho position of two phenylenes (preferably any one of them) or one of the phenylene at the ortho position (all four at a maximum, preferably any one of the four phenylenes) is substituted with methyl.
  • the polycyclic aromatic compound represented by the general formula (1) or (2) and the multimer thereof are disclosed in, for example, International Publication No. WO 2015/102118. It can be synthesized by applying the method. That is, as shown in the following scheme, an intermediate in which ring A (ring a), ring B (ring b), and ring C (ring c) are bonded to each other at X 1 or X 2 is synthesized, and the resultant is tandem hetero-free.
  • the desired polycyclic aromatic compound and its multimer can be synthesized by cyclization by the Del Crafts reaction (continuous aromatic electrophilic substitution reaction).
  • X represents halogen or hydrogen, and the definitions of other symbols are the same as those described above.
  • the intermediate before cyclization in the above scheme can also be synthesized by the method shown in WO 2015/102118 and the like. That is, an intermediate having a desired substituent can be synthesized by appropriately combining a Buchwald-Hartwig reaction, a Suzuki coupling reaction, or an etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction.
  • the cyclization by the tandem hetero Friedel-Crafts reaction shown in the above scheme is a reaction for introducing B (boron) connecting A ring (a ring), B ring (b ring) and C ring (c ring).
  • B boron
  • X 1 and X 2 is ortho-metallized with n-butyllithium, sec-butyllithium, t-butyllithium, or the like.
  • boron trichloride, boron tribromide, etc. are added, lithium-boron metal exchange is performed, and then a Bronsted base such as N, N-diisopropylethylamine is added to cause a tandem borafriedder-Crafts reaction.
  • a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.
  • the polycyclic aromatic compound and its multimer include a compound in which at least a part of hydrogen atoms are substituted with deuterium and a compound in which at least a part of hydrogen atoms are substituted with halogen such as fluorine and chlorine.
  • a compound or the like can be synthesized in the same manner as described above by using a raw material in which a desired portion is deuterated, fluorinated, or chlorinated.
  • Anthracene-based compound Anthracene-based compound basically functions as a host.
  • the anthracene-based compound may be any compound having an anthracene structure, such as a compound represented by the following general formula (3).
  • L in the anthracene-based compound represented by the general formula (3) is a single bond, arylene having 6 to 18 carbon atoms, or alkylene having 1 to 10 carbon atoms.
  • One hydrogen may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl (second substituent).
  • second substituent aryl, heteroaryl, alkyl, and cycloalkyl, which can be substituted on arylene and alkylene
  • the description on the “second substituent” in the general formula (2) is cited. be able to.
  • Examples of the arylene include divalent groups having 6 to 18 carbon atoms among divalent groups represented by removing any two hydrogen atoms from the “aryl ring” described in the above polycyclic aromatic compound. .
  • alkylene examples include a divalent group having 1 to 10 carbon atoms among divalent groups represented by removing any one hydrogen atom from “alkyl” described in the above polycyclic aromatic compound. Any of a straight chain and a branched chain may be used, and examples thereof include methylene, ethylene, propylene, isopropylene, butylene, isobutylene, and pentylene.
  • Ar 4 in the general formula (3) is each independently substituted with a group selected from hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, alkyl having 1 to 4 carbons and cycloalkyl having 5 to 10 carbons. Is Cyril.
  • alkyl having 1 to 4 carbon atoms to be substituted with silyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl and the like. And are substituted with these alkyls.
  • sil substituted with alkyl having 1 to 4 carbon atoms include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, ethyl Dimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, i-propyl diethylsilyl, butyl diethylsilyl, sec-butyl Diethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, buty
  • Silyl-substituted cycloalkyl having 5 to 10 carbon atoms includes cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, bicyclo [ 1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl And three hydrogens in silyl are each independently substituted by these cycloalkyls.
  • sil substituted by cycloalkyl having 5 to 10 carbon atoms includes tricyclopentylsilyl, tricyclohexylsilyl and the like.
  • substituted silyl examples include dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls. Examples of the above include the groups described above.
  • n is 0 or 1. That is, the compound represented by the general formula (3) is classified into a compound represented by the following general formula (3a) and a compound represented by the following general formula (3b). In the following formulas (3a) and (3b), the definition of each symbol is the same as that of the general formula (3).
  • X is each independently a group represented by the following formula (3-X1), formula (3-X2) or formula (3-X3). * In the following formula (3-X1), formula (3-X2) or formula (3-X3) indicates a bonding position to the 9-position or the 10-position of the anthracene ring in the formula (3).
  • Ar 1 and Ar 2 in the formula (3-X1) or the formula (3-X2) are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl , Chrysenyl, triphenylenyl, pyrenylyl, carbazolyl, benzocarbazolyl, phenyl-substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiophenyl, dibenzothiophenyl, or naphthobenzothiophenyl, and at least one of these
  • One hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and may be substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, phenyl, or naphthyl
  • the alkyl having 1 to 6 carbon atoms includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-butyl Pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl and the like.
  • Examples of the above cycloalkyl having 3 to 14 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl having 1 to 4 carbons (particularly methyl). Substitutes, bicyclo [1.0.1] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, bicyclo [1.2.1] hexyl, bicyclo [3.0.
  • Ar 3 in the formula (3-X3) is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, carbazolyl, benzocarbazolyl, or phenyl-substituted carbazolyl Benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothiophenyl, dibenzothiophenyl or naphthobenzothiophenyl.
  • At least one hydrogen of these groups which may be selected as Ar 3 further includes alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkyl or cycloalkyl substituted or unsubstituted phenyl, alkyl or cycloalkyl.
  • the group represented by the above formula (3-X3) is phenyl, phenanthryl, a group represented by the following formula (3-X3-1), or a group represented by the following formula (3-X3-2).
  • at least one of these hydrogens may be substituted by the above-mentioned second substituent, aryl, heteroaryl, alkyl or cycloalkyl, or substituted by alkyl having 1 to 6 carbons. It may be.
  • * In the following formulas (3-X3-1) and (3-X3-2) indicates the bonding position to the 9th or 10th position of the anthracene ring in the general formula (3).
  • Ar 5 is each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, phenyl-substituted carbazolyl, benzofuranyl, naphthobenzofuran Nyl, benzothiophenyl or naphthobenzothiophenyl, and at least one of these hydrogens may be further substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons.
  • At least one hydrogen of the groups represented by the above formulas (3-X3-1) and (3-X3-2) may be substituted with alkyl having 1 to 6 carbon atoms or 3 to 3 carbon atoms.
  • the 14 cycloalkyl is as described above.
  • Anthracene-based compound represented by general formula (3-1-X) Further, examples of anthracene-based compound include compounds represented by the following general formula (3-1-X).
  • the compounds represented by the general formulas (3-1-X) and (3-1-X1) to (3-1-X4) basically have two phenyl groups at the 9-position and the 10-position.
  • a specific aryl is substituted at the 2-position, 5-position, 3-position and 4-position or 2-position, 4-position and 5-position of one phenyl group (bonded to anthracene at the 1-position).
  • Compound. By selecting such a substitution position and an aryl structure, it is possible to obtain a compound that achieves more excellent driving voltage, luminous efficiency, and device life as a light emitting layer material.
  • Ar is an optionally substituted aryl
  • n is 1 or 2
  • Ar is bonded to either the x-position or the y-position.
  • N is 2
  • Ar is bonded to both the x-position and the y-position, and the respective structures may be the same or different. That is, the general formula (3-1-X) has a structure represented by the following formula (3-1-Xa), a structure represented by the formula (3-1-Xb), and a structure represented by the following formula (3-1-Xc) ).
  • the “aryl” of the “aryl which may be substituted” as Ar is, for example, an aryl having 6 to 30 carbon atoms.
  • Preferred “aryl” is aryl having 6 to 18 carbon atoms, more preferably aryl having 6 to 14 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms.
  • aryl include phenyl which is a monocyclic aryl, (1-, 2-) naphthyl which is a fused bicyclic aryl, and acenaphthylene- (1-, 3-, which is a fused tricyclic aryl.
  • aryl among these, phenyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl and the like are preferable, phenyl, 1-naphthyl, 2-naphthyl and phenanthryl are more preferable, and phenyl, 1-naphthyl is particularly preferable. Examples include naphthyl or 2-naphthyl.
  • the substituent on the “aryl” is not particularly limited as long as the desired properties can be obtained, but is preferably an alkyl having 1 to 12 carbons, a cycloalkyl having 3 to 12 carbons, or a 6 to 18 carbons. And the like.
  • The“ alkyl having 1 to 12 carbons ”as the substituent may be either a straight chain or a branched chain. That is, it is a straight-chain alkyl having 1 to 12 carbons or a branched alkyl having 3 to 12 carbons. More preferably, it is an alkyl having 1 to 6 carbons (branched alkyl having 3 to 6 carbons), and further preferably, an alkyl having 1 to 4 carbons (branched alkyl having 3 to 4 carbons) is used. is there.
  • Specific 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 or 2-ethylbutyl; and the like, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl, and methyl , Isopropyl or t-butyl are more preferred.
  • cycloalkyl having 3 to 12 carbon atoms examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl. can give. Among these, cyclopentyl or cyclohexyl is preferred.
  • aryl having 6 to 18 carbon atoms an aryl having 6 to 14 carbons is preferable, and an aryl having 6 to 10 carbons is particularly preferable.
  • Specific examples include phenyl, (2-, 3-, 4-) biphenylyl, (1-, 2-) naphthyl, (1-, 2-, 3-, 4-, 9-) phenanthryl, (1-, 2-) phenanthryl, 2-) triphenylenyl and the like.
  • the substituent on “aryl” is preferably unsubstituted, but when a substituent is present, its number is, for example, the maximum substitutable number, preferably 1 to 3, more preferably 1 to 3. One or two, more preferably one.
  • Ar 1 is an optionally substituted aryl.
  • the “aryl” of the “aryl which may be substituted” as Ar 1 includes, for example, aryl having 6 to 30 carbon atoms.
  • Preferred “aryl” is aryl having 6 to 18 carbon atoms, more preferably aryl having 6 to 14 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms.
  • aryl include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, and (1-, 2-) naphthyl which is a fused bicyclic aryl And condensed tricyclic aryl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1 -, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl, a condensed tetracyclic aryl triphenylene- (1-, 2-) yl, pyrene- (1-, 2) -, 4-) yl, naphthacene- (1-, 2-, 5-) yl, condensed pentacyclic aryl perylene- (1-, 2-, 3-) yl, pentacene- (1-
  • aryl among these, phenyl, biphenylyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl and the like are preferred, and phenyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl, phenanthryl and Triphenylenyl is exemplified, and phenyl, 1-naphthyl and 2-naphthyl are particularly preferred.
  • the substituent on the “aryl” is not particularly limited as long as the desired properties can be obtained, but is preferably an alkyl having 1 to 12 carbons, a cycloalkyl having 3 to 12 carbons, or a 6 to 18 carbons. And the like.
  • aryl having 6 to 18 carbon atoms an aryl having 6 to 14 carbons is preferable, and an aryl having 6 to 10 carbons is particularly preferable.
  • Specific examples include phenyl, (1-, 2-) naphthyl, (1-, 2-, 3-, 4-, 9-) phenanthryl and the like.
  • the substituent on “aryl” is preferably unsubstituted, but when a substituent is present, its number is, for example, the maximum substitutable number, preferably 1 to 3, more preferably 1 to 3. One or two, more preferably one.
  • the number m of substituents of Ar 1 is an integer that can be substituted from 0 to ⁇ at the maximum.
  • m is 2 or more, the structures of Ar 1 may be the same or different, and preferably an integer of 0 to 2. And more preferably 0 or 1.
  • alkyl as R in the general formula (3-1-X), for example, an alkyl having 1 to 12 carbons can be mentioned, and the specific description thereof can be referred to the above description of Ar. it can.
  • cycloalkyl as R in the general formula (3-1-X) includes, for example, cycloalkyl having 3 to 12 carbon atoms, and specific description thereof is the same as that described in the section of Ar. be able to.
  • a is an integer of 0 to 5
  • b is an integer of 0 to 3
  • b + n is 4 or less
  • c is an integer which can be substituted from 0 to ⁇ at the maximum.
  • c + m is equal to or smaller than an integer that can be replaced by ⁇ at the maximum
  • d is an integer of 0 to 4.
  • a is an integer from 0 to 2
  • b is 0 or 1
  • b + n is 4 or less
  • c is an integer from 0 to 2
  • d is an integer from 0 to 2. More preferably, ad is 0.
  • hydrogen in an anthracene skeleton hydrogen in phenyl substituted in the 9th and 10th positions of anthracene, and hydrogen in Ar, Ar 1 or R At least one may be replaced by deuterium.
  • Anthracene-based compound represented by general formula (3-1-X1) has a structure represented by the following formula (3-1-X1a), and a compound represented by formula (3-1-X1b) And a structure represented by the formula (3-1-X1c).
  • Ar, Ar 1 and R in the general formula (3-1-X1) include those described in the general formula (3-1-X).
  • the number m of substituents of Ar 1 is an integer of 0 to 5, preferably an integer of 0 to 2, and more preferably 0 or 1.
  • a is an integer of 0 to 5
  • b is an integer of 0 to 3 (b + n is 4 or less)
  • c is an integer of 0 to 5 (c + m Is 5 or less)
  • d is an integer of 0-4. More preferably, a is an integer from 0 to 2, b is 0 or 1, c is an integer from 0 to 2, and d is an integer from 0 to 2. More preferably, ad is 0.
  • hydrogen in an anthracene skeleton hydrogen in phenyl substituted at the 9th and 10th positions of anthracene, and hydrogen in Ar, Ar 1 or R At least one may be replaced by deuterium.
  • General formula (3-1-X2) has a structure represented by the following formula (3-1-X2a) and a compound represented by the following formula (3-1-X2b) And a structure represented by the formula (3-1-X2c).
  • the naphthalene ring is 1-naphthyl or 2-naphthyl.
  • Ar, Ar 1 and R in the general formula (3-1-X2) include those described in the general formula (3-1-X).
  • the number m of substituents of Ar 1 is an integer of 0 to 7, preferably an integer of 0 to 2, and more preferably 0 or 1.
  • a is an integer of 0 to 5
  • b is an integer of 0 to 3 (b + n is 4 or less)
  • c is an integer of 0 to 7 (c + m Is 7 or less)
  • d is an integer of 0-4. More preferably, a is an integer from 0 to 2, b is 0 or 1, c is an integer from 0 to 2, and d is an integer from 0 to 2. More preferably, ad is 0.
  • hydrogen in an anthracene skeleton hydrogen in phenyl substituted at the 9th or 10th position of anthracene, and hydrogen in Ar, Ar 1 or R At least one may be replaced by deuterium.
  • Anthracene-based compound represented by general formula (3-1-X3) has a structure represented by the following formula (3-1-X3a), and a compound represented by the following formula (3-1-X3b) And a structure represented by the formula (3-1-X3c).
  • the phenanthrene ring is 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl.
  • Ar, Ar 1 and R in the general formula (3-1-X3) include those described in the general formula (3-1-X).
  • the number m of substituents of Ar 1 is an integer of 0 to 9, preferably an integer of 0 to 2, and more preferably 0 or 1.
  • a is an integer of 0 to 5
  • b is an integer of 0 to 3 (b + n is 4 or less)
  • c is an integer of 0 to 9 (c + m Is 9 or less)
  • d is an integer of 0-4. More preferably, a is an integer from 0 to 2, b is 0 or 1, c is an integer from 0 to 2, and d is an integer from 0 to 2. More preferably, ad is 0.
  • hydrogen in an anthracene skeleton hydrogen in phenyl substituted at the 9th and 10th positions of anthracene, and hydrogen in Ar, Ar 1 or R At least one may be replaced by deuterium.
  • Anthracene-based compound represented by general formula (3-1-X4) has a structure represented by the following formula (3-1-X4a), and a compound represented by formula (3-1-X4b) And a structure represented by the formula (3-1-X4c).
  • the triphenylene ring is 1-triphenylenyl or 2-triphenylenyl.
  • Ar, Ar 1 and R in the general formula (3-1-X4) include those described in the general formula (3-1-X).
  • the number m of substituents of Ar 1 is an integer of 0 to 11, preferably an integer of 0 to 2, and more preferably 0 or 1.
  • a is preferably an integer of 0 to 5
  • b is an integer of 0 to 3 (b + n is 4 or less)
  • c is an integer of 0 to 11 (c + m Is 11 or less)
  • d is an integer of 0-4. More preferably, a is an integer from 0 to 2, b is 0 or 1, c is an integer from 0 to 2, and d is an integer from 0 to 2. More preferably, ad is 0.
  • hydrogen in an anthracene skeleton hydrogen in phenyl substituted at the 9th and 10th positions of anthracene, and hydrogen in Ar, Ar 1 or R At least one may be replaced by deuterium.
  • Anthracene compounds having at least one deuterium are also represented by formulas (3), (3-1-X) and (3-1-X1) to (3-1-X4). At least one hydrogen in certain compounds may be replaced by deuterium. That is, the anthracene-based compound may be a compound having at least one deuterium, such as compounds (3-2-1) to (2-2A-674) described later.
  • the ratio of deuterium to the total number of hydrogen and deuterium bonded to carbon constituting an aromatic ring in one molecule is preferably 10 to 100%, more preferably 30 to 100%. %, More preferably 50 to 100%, still more preferably 80 to 100%, particularly preferably 100%.
  • hydrogen and deuterium bonded to a carbon (ring-forming carbon) constituting an aromatic ring in one molecule refers to hydrogen and deuterium bonded directly to a ring-forming carbon. Hydrogen and deuterium which are bonded to a ring-forming carbon through a linking atom such as carbon or nitrogen, such as hydrogen and deuterium of a substituent to be bonded, are not included.
  • the number of “carbons constituting an aromatic ring in one molecule (ring-forming carbon)” is 36, of which “deuterium (D)” and 5 And 18 of them are bonded to “hydrogen (H)”. Therefore, the “ratio of heavy hydrogen” in the compound (3-327) is about 21.7% ( ⁇ 5 / (5 + 18) ⁇ 100).
  • anthracene-based compound examples include the following compounds.
  • “Me” represents methyl
  • “Et” represents ethyl
  • “tBu” represents t-butyl
  • “iPr” represents propyl
  • “D” represents deuterium.
  • FIG. 1 is a schematic sectional view showing the organic EL device according to the present embodiment.
  • the organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a The provided hole transport layer 104, the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and the electron transport layer 106 provided on the electron transport layer 106. Electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.
  • the organic EL element 100 is manufactured by reversing the manufacturing order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer 107.
  • An electron transport layer 106 provided on the electron transport layer 106, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, And the anode 102 provided on the hole injection layer 103 may be provided.
  • the minimum constitutional unit is composed of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, the electron injection layer
  • the layer 107 is an optional layer. Further, each of the above layers may be composed of a single layer or a plurality of layers.
  • the layer constituting the organic EL element in addition to the above-described embodiment of “substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode”, “Substrate / anode / hole transport layer / emission layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / emission layer / electron transport layer / electron injection layer / cathode”, “substrate / Anode / hole injection layer / hole transport layer / emission layer / electron injection layer / cathode "," substrate / anode / hole injection layer / hole transport layer / emission layer / electron transport layer / cathode "," substrate / Anode / light-emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole transport layer / emission layer / electron
  • the substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like.
  • the substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose.
  • a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used.
  • a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable.
  • the thickness only needs to be 0.2 mm or more, as long as it has a thickness sufficient to maintain mechanical strength.
  • the upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less.
  • alkali-free glass is preferable because it is preferable that the amount of ions eluted from the glass is small, but soda lime glass having a barrier coat such as SiO 2 is also commercially available. 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 enhance gas barrier properties.
  • a synthetic resin plate, film, or sheet having low gas barrier properties is used as the substrate 101. When used, it is preferable to provide a gas barrier film.
  • the anode 102 plays a role of injecting holes into the light emitting layer 105. Note that when at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers. Become.
  • an inorganic compound and an organic compound can be given.
  • the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide) (IZO), metal halides (eg, copper iodide), copper sulfide, carbon black, ITO glass, Nesa glass, and the like.
  • the organic compound include conductive polymers such as polythiophene such as poly (3-methylthiophene), polypyrrole, and polyaniline. In addition, it can be appropriately selected from the substances used as the anode of the organic EL element.
  • the resistance of the transparent electrode is not limited as long as a current sufficient for light emission of the light emitting element can be supplied, but is preferably low from the viewpoint of power consumption of the light emitting element.
  • an ITO substrate having a resistance of 300 ⁇ / ⁇ or less functions as an element electrode.
  • a substrate of about 10 ⁇ / ⁇ can be supplied at present, 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 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104.
  • the hole transport layer 104 plays a role in efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light-emitting layer 105.
  • the hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more of the hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder. Is done. Further, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injecting / transporting material.
  • a hole injection / transport substance As a hole injection / transport substance, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes to which an electric field is applied, and the hole injection efficiency is high, and the injected holes are efficiently transported. It is desirable to do. For that purpose, it is preferable that the ionization potential is small, the hole mobility is large, the stability is further improved, and impurities serving as traps are less likely to be generated during production and use.
  • Examples of the material for forming the hole injection layer 103 and the hole transport layer 104 include a compound conventionally used as a hole charge transport material in a photoconductive material, a p-type semiconductor, and a hole injection layer of an organic EL element. Any compound can be selected from known compounds used for the hole transport layer and used. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), and triarylamine derivatives (aromatic tertiary).
  • polycarbonates having the above monomers in the side chain polycarbonates having the above monomers in the side chain, styrene derivatives, polyvinyl carbazole, polysilane, etc. are preferred, but light emitting devices
  • the compound is not particularly limited as long as it is a compound capable of forming a thin film required for the preparation of the compound, injecting holes from the anode, and transporting holes.
  • 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 tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known for doping of electron donors.
  • TCNQ tetracyanoquinonedimethane
  • F4TCNQ 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane
  • the light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied.
  • the material for forming the light-emitting layer 105 may be any compound that emits light when excited by recombination of holes and electrons (light-emitting compound), and can form a stable thin film, and It is preferred that the compound exhibits a strong luminescence (fluorescence) efficiency.
  • a polycyclic aromatic compound represented by the above general formula (1) and a polycyclic aromatic compound having a plurality of structures represented by the above general formula (1) are used as dopant materials.
  • An anthracene-based compound can be used as a host material for at least one of the multimers.
  • the light emitting layer may be a single layer or a plurality of layers, each of which is formed of a light emitting layer material (host material, dopant material).
  • the host material and the dopant material may each be of one type or a combination of a plurality of types.
  • the dopant material may be included in the entire host material, may be partially included, or may be included therein.
  • As a doping method it can be formed by a co-evaporation method with a host material, but may be mixed with the host material in advance and then vapor-deposited at the same time.
  • the amount of host material used depends on the type of host material, and may be determined according to the characteristics of the host material.
  • the standard of the usage amount of the host material is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and further preferably 90 to 99.9% by weight of the whole material for the light emitting layer. It is.
  • the amount of the dopant material used depends on the type of the dopant material, and may be determined according to the characteristics of the dopant material.
  • the standard of the usage amount of the dopant is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, further preferably 0.1 to 10% by weight of the whole material for the light emitting layer. is there.
  • the above range is preferable, for example, in that the density quenching phenomenon can be prevented.
  • the content ratio of the polycyclic aromatic compound represented by the general formula (1) in the light-emitting layer and its multimer to the anthracene compound [polycyclic aromatic compound and its multimer / anthracene compound]
  • the weight ratio is preferably 0.001 / 99.999 to 50/50, more preferably 0.05 / 99.95 to 20/80, and still more preferably 0.1 / 99.9 to 10/90. is there.
  • Host materials that can be used in combination with anthracene-based compounds include condensed ring derivatives such as pyrene, bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, and fluorene derivatives, which have long been known as light emitters. And benzofluorene derivatives.
  • 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 in 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 transporting layer 106 and the electron injecting layer 107 are each formed by laminating and mixing one or more of the electron transporting / injecting materials or a mixture of the electron transporting / injecting material and the polymer binder.
  • the electron injection / transport layer is a layer that controls the injection of electrons from the cathode and the transport of electrons. It is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently.
  • the substance be a substance having a high electron affinity, a high electron mobility, excellent stability, and hardly generating impurities serving as traps during production and use.
  • the electron transport capability is not so high. Even if it is not high, the effect of improving the luminous efficiency is equivalent to a material having a high electron transporting ability. Therefore, the electron injecting / transporting layer in the present embodiment may include a function of a layer that can efficiently block the movement of holes.
  • a material (electron transporting material) for forming the electron transporting layer 106 or the electron injecting layer 107 a compound conventionally used as an electron transporting compound in a photoconductive material, and used for an electron injecting layer and an electron transporting layer of an organic EL device. Any of the known compounds can be used.
  • the material used for the electron transporting layer or the electron injecting layer carbon, hydrogen, oxygen, sulfur, a compound comprising an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from silicon and phosphorus, It is preferable to contain at least one selected from a pyrrole derivative, a fused ring derivative thereof, and a metal complex having an electron-accepting nitrogen.
  • condensed ring type aromatic ring derivatives such as naphthalene and anthracene
  • styryl type aromatic ring derivatives typified by 4,4′-bis (diphenylethenyl) biphenyl
  • perinone derivatives such as naphthalene and anthracene
  • coumarin derivatives such as naphthalimide derivatives
  • quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives.
  • the metal complex having an electron accepting nitrogen include a hydroxyazole complex such as a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, a flavonol metal complex, and a benzoquinoline metal complex. These materials may 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, and oxadiazole.
  • Derivatives such as 1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene), thiophene derivatives, and triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4- Triazole), metal complexes of thiadiazole derivatives, oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazoles, gallium complexes, pyrazole derivatives, perfluorinated Nylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis (benzo [h] quinolin-2-yl) -9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzones Imidazole derivatives (such as tris (N-phenylbenzimidazol
  • a metal complex having an electron-accepting nitrogen can also be used.
  • a hydroxyazole complex such as a quinolinol-based metal complex and a hydroxyphenyloxazole complex
  • an azomethine complex such as a quinolinol-based metal complex and a hydroxyphenyloxazole complex
  • an azomethine complex such as a tropolone metal complex, a flavonol metal complex, and a benzoquinoline metal complex.
  • a hydroxyazole complex such as a quinolinol-based metal complex and a hydroxyphenyloxazole complex
  • an azomethine complex such as a quinolinol-based metal complex and a hydroxyphenyloxazole complex
  • an azomethine complex such as a quinolinol-based metal complex and a hydroxyphenyloxazole complex
  • an azomethine complex such as a quinolinol-based metal complex and a hydroxyphenyloxazole complex
  • the above-mentioned materials may be used alone, but may be used in combination 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-based 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, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing At least one of a heterocyclic ring or cyano, and each of R 13 to R 16 is 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
  • Is each independently an integer of 0 to 3.
  • substituent when “optionally substituted” or “substituted” include aryl, heteroaryl, alkyl and cycloalkyl.
  • R 11 and R 12 are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen.
  • R 13 to R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl.
  • R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano.
  • R 11 and R 12 are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen.
  • 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.
  • substituents when “optionally substituted” or “substituted” include aryl, heteroaryl, alkyl and cycloalkyl.
  • X 1 include divalent groups represented by the following formulas (X-1) to (X-9).
  • Ra is each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.
  • borane derivative examples include, for example, the following compounds.
  • 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 formula (ETM-2-1) or (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 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) 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 cycloalkyl having 3 to 12 carbon atoms) Alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms), and R 11 and R 12 may combine to form a ring.
  • the “pyridine-based substituent” is any of the following formulas (Py-1) to (Py-15), and the pyridine-based substituents are each independently an alkyl or carbon atom having 1 to 5 carbon atoms. It may be substituted with cycloalkyl of formulas 5 to 10. Further, the pyridine-based substituent may be bonded to ⁇ , an anthracene ring or a fluorene ring in each formula via a phenylene group or a naphthylene group.
  • the pyridine-based substituent is any of the above formulas (Py-1) to (Py-15), and among them, any of the following formulas (Py-21) to (Py-44) Is preferred.
  • At least one hydrogen in each pyridine derivative may be substituted with deuterium, and among the two “pyridine-based substituents” in the above formula (ETM-2-1) and formula (ETM-2-2) May be replaced by an aryl.
  • the “alkyl” for R 11 to R 18 may be linear or branched, and includes, for example, linear alkyl having 1 to 24 carbons or branched alkyl having 3 to 24 carbons.
  • Preferred “alkyl” is alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons). More preferred “alkyl” is alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons). More preferred “alkyl” is alkyl having 1 to 6 carbons (branched alkyl having 3 to 6 carbons). Particularly preferred “alkyl” is alkyl having 1 to 4 carbons (branched alkyl having 3 to 4 carbons).
  • alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3 , 3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethyl Hexyl, n-dec
  • the “cycloalkyl” for R 11 to R 18 includes, for example, 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.
  • cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.
  • 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 preferably an aryl having 6 to 12 carbon atoms.
  • aryl having 6 to 30 carbon atoms include phenyl which is a monocyclic aryl, (1-, 2-) naphthyl which is a fused bicyclic aryl, and acenaphthylene- (which is a fused tricyclic aryl.
  • Preferred “aryl having 6 to 30 carbon atoms” include phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl. -Naphthyl or 2-naphthyl.
  • R 11 and R 12 in the above formula (ETM-2-2) may combine to form a ring, and as a result, the 5-membered ring of the fluorene skeleton has cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, Cyclohexane, fluorene or indene may be spiro-bonded.
  • pyridine derivative examples include, for example, the following compounds.
  • 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 WO 2010/134352.
  • X 12 to X 21 represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted Represents heteroaryl.
  • the substituent when substituted, includes aryl, heteroaryl, alkyl and cycloalkyl.
  • fluoranthene derivative examples include the following compounds.
  • the BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a polymer of a polycyclic aromatic compound 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, diarylboryl (the two aryls are linked via a single bond or a linking group; ), Alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
  • adjacent groups among R 1 to R 11 may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring Is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl It may be substituted by oxy, and at least one hydrogen in these may be substituted by aryl, heteroaryl, alkyl or cycloalkyl.
  • At least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.
  • BO derivative include, for example, the following compounds.
  • 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;
  • R 1 to R 4 are each independently hydrogen, alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons or carbon 6-20 aryls.
  • Ar can be independently selected from divalent benzene or naphthalene as appropriate, and the two Ars may be different or the same, but are the same from the viewpoint of ease of synthesis of the anthracene derivative. It is preferred that Ar is bonded to pyridine to form a “site consisting of Ar and pyridine”, and this site is an anthracene as a group represented by any of the following formulas (Py-1) to (Py-12). Is bound to.
  • a group represented by any of the above formulas (Py-1) to (Py-9) is preferable, and a group represented by any of the above formulas (Py-1) to (Py-6) is preferable.
  • the two “sites composed of Ar and pyridine” bonded to anthracene may have the same or different structures, but preferably have the same structure from the viewpoint of easy synthesis of an anthracene derivative. However, from the viewpoint of device characteristics, it is preferable that the two “sites composed of Ar and pyridine” have the same or different structures.
  • the alkyl having 1 to 6 carbon atoms in R 1 to R 4 may be linear or branched. That is, it is a straight-chain alkyl having 1 to 6 carbons or a branched alkyl having 3 to 6 carbons. More preferably, it is an alkyl having 1 to 4 carbons (a branched alkyl having 3 to 4 carbons).
  • Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl and the like, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or T-butyl is preferred, and methyl, ethyl or t-butyl is more preferred.
  • cycloalkyl having 3 to 6 carbon atoms for 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 phenyl which is a monocyclic aryl, (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 and bicyclic aryl (2 -, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (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,
  • Preferred "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 preferably, it is phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, most preferably 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 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 referred to.
  • An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable.
  • phenyl 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) Can be cited.
  • anthracene derivatives include, for example, the following compounds.
  • 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 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.
  • An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable.
  • phenyl examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl and the like.
  • Ar 2 is each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbons), cycloalkyl (preferably cycloalkyl having 3 to 12 carbons) or aryl (preferably aryl having 6 to 30 carbons) ), And the two Ar 2 may combine to form a ring.
  • the “alkyl” in Ar 2 may be either straight-chain or branched, and includes, for example, straight-chain alkyl having 1 to 24 carbons or branched-chain alkyl having 3 to 24 carbons.
  • Preferred “alkyl” is alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons). More preferred “alkyl” is alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons). More preferred “alkyl” is alkyl having 1 to 6 carbons (branched alkyl having 3 to 6 carbons). Particularly preferred “alkyl” is alkyl having 1 to 5 carbons (branched alkyl having 3 to 5 carbons).
  • alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), Examples include n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.
  • the “cycloalkyl” in Ar 2 includes, for example, 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 “cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.
  • a preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, and further preferably an aryl having 6 to 14 carbon atoms. Preferably, it is an 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 form a ring, as a result, the 5-membered ring of the fluorene skeleton, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene are spiro-linked You may.
  • benzofluorene derivative examples include, for example, the following compounds.
  • 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). The details are also described in WO2013 / 079217.
  • R 5 is a 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 carbons, cycloalkyl having 3 to 20 carbons, heteroalkyl having 1 to 20 carbons, aryl having 6 to 20 carbons, 5 to 5 carbons 20 heteroaryl, C1-20 alkoxy or C6-20 aryloxy
  • R 7 and R 8 are each independently a substituted or unsubstituted aryl having 6 to 20 carbons or a heteroaryl having 5 to 20 carbons
  • R 9 is oxygen or sulfur;
  • j is 0 or 1
  • k is 0 or 1
  • 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 include hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, and an aryl ether group.
  • 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 part, and when n is 3, R 1 does not exist.
  • the alkyl group means a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, and a butyl group, which may be unsubstituted or substituted.
  • the substituent is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group. This point is also common to the following description.
  • the number of carbon atoms in 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 refers to, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted.
  • the number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20.
  • the aralkyl group refers to, for example, an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group and a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon are unsubstituted or substituted. It doesn't matter.
  • the carbon number of the aliphatic moiety is not particularly limited, but is usually in the range of 1 to 20.
  • Alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group and 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 to 20.
  • the cycloalkenyl group refers to, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexene group, which may be unsubstituted or substituted. I don't care.
  • Alkynyl group means, for example, 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 in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.
  • Alkoxy group means, for example, an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted.
  • the carbon number of the alkoxy group is not particularly limited, it is usually in the range of 1 to 20.
  • Alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
  • a cycloalkylthio group is a group in which an oxygen atom of an ether bond of a cycloalkoxy group is substituted with a sulfur atom.
  • the aryl ether group refers to, for example, 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 in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.
  • the arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is substituted with a sulfur atom.
  • the aryl group refers to, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenylyl group, and a pyrenyl group.
  • the aryl group may be unsubstituted or substituted.
  • the carbon number of the aryl group is not particularly limited, but is usually in the range of 6 to 40.
  • heterocyclic group refers to, for example, a cyclic structure group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group. It doesn't matter.
  • the carbon number of the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.
  • Halogen refers to fluorine, chlorine, bromine and iodine.
  • the aldehyde group, carbonyl group, and amino group may also include groups substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocyclic ring, and the like.
  • aliphatic hydrocarbons aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocycles may be unsubstituted or substituted.
  • silyl group means a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted.
  • carbon number of the silyl group is not particularly limited, it is usually in the range of 3 to 20. Further, the number of silicon is usually 1 to 6.
  • the condensed ring formed between adjacent substituents is, 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 It is a conjugated or non-conjugated fused ring formed between Ar 2 and the like.
  • n when n is 1, may be formed conjugated or non-conjugated fused ring with two of R 1 each other.
  • These condensed rings may contain nitrogen, oxygen and sulfur atoms in the ring structure, or may be condensed with another ring.
  • phosphine oxide derivative examples include the following compounds.
  • 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). The details are also described in WO 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 of the “optionally substituted aryl” includes, for example, 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 preferably, it is an aryl having 6 to 12 carbon atoms.
  • aryl include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, and (1-, 2-) naphthyl which is a fused 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-2-
  • heteroaryl of the “optionally substituted heteroaryl” includes, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, and a heteroaryl having 2 to 20 carbon atoms.
  • Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is still more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred.
  • the heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 hetero atoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • heteroaryl examples include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phen
  • At least one hydrogen in the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl and heteroaryl.
  • pyrimidine derivative examples include, for example, the following compounds.
  • 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 the carbazole derivatives are bonded by single bonds or the like. The details are described in U.S. Publication No. 2014/0197386.
  • Ar is each independently an optionally substituted aryl or an optionally substituted heteroaryl.
  • n is each independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.
  • aryl of the “optionally substituted aryl” includes, for example, 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 preferably, it is an aryl having 6 to 12 carbon atoms.
  • aryl include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, and (1-, 2-) naphthyl which is a fused 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-2-
  • heteroaryl of the “optionally substituted heteroaryl” includes, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, and a heteroaryl having 2 to 20 carbon atoms.
  • Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is still more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred.
  • the heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 hetero atoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • heteroaryl examples include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phen
  • At least one hydrogen in the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl and 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.
  • ETM-9 a plurality of compounds represented by the above formula
  • they may be bonded by 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, for example, the following compounds.
  • 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 U.S. 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, and is preferably 2 or 3.
  • aryl of the “optionally substituted aryl” includes, for example, 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 preferably, it is an aryl having 6 to 12 carbon atoms.
  • aryl include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, and (1-, 2-) naphthyl which is a fused 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-2-
  • heteroaryl of the “optionally substituted heteroaryl” includes, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, and a heteroaryl having 2 to 20 carbon atoms.
  • Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is still more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred.
  • the heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 hetero atoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.
  • heteroaryl examples include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phen
  • At least one hydrogen in the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl and heteroaryl.
  • triazine derivative examples include the following compounds.
  • 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-based substituent” means that the pyridyl group in the “pyridine-based substituent” in the above formulas (ETM-2), (ETM-2-1) and (ETM-2-2) is benzo. It is a substituent replacing the 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 carbons, cycloalkyl having 3 to 12 carbons or aryl having 6 to 30 carbons, and is represented by the above formula (ETM-2-1) or ( It may be cited to the description of R 11 in ETM-2-2).
  • ⁇ is further preferably an anthracene ring or a fluorene ring, and in this case, the structure described in the above formula (ETM-2-1) or (ETM-2-2) can be referred to.
  • R 11 to R 18 can refer to the description in the above formula (ETM-2-1) or formula (ETM-2-2).
  • two pyridine-based substituents are described as being bonded. However, when these are replaced with benzimidazole-based substituents, both are substituted.
  • benzimidazole derivative examples 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 (ETM-12-1). Details are described in WO 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 each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbons), cycloalkyl (preferably cycloalkyl having 3 to 12 carbons) or aryl (preferably carbon Aryl of formulas 6 to 30).
  • alkyl preferably alkyl having 1 to 24 carbons
  • cycloalkyl preferably cycloalkyl having 3 to 12 carbons
  • aryl preferably carbon Aryl of formulas 6 to 30.
  • each phenanthroline derivative may be replaced with deuterium.
  • R 11 ⁇ R 18, cycloalkyl and aryl may be cited to the description of R 11 ⁇ R 18 in the formula (ETM-2).
  • ⁇ is, for example, the following structural formula in addition to the above examples.
  • R in the following structural formulas is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl.
  • phenanthroline derivative examples 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), bathocuproine, 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 -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-based metal complexes include 8-quinolinol lithium, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, tris (3 , 4-Dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) ( Phenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8- Quinolinolate) (4- Butylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-methyl- 8-quinol lithium
  • 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” The pyridyl group in the “substituent” is a substituent in which a thiazole group or a benzothiazole group is substituted, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with deuterium.
  • ⁇ is further preferably an anthracene ring or a fluorene ring, and in this case, the structure described in the above formula (ETM-2-1) or (ETM-2-2) can be referred to.
  • R 11 to R 18 can refer to the description in the above formula (ETM-2-1) or formula (ETM-2-2).
  • two pyridine-based substituents are described as being bonded, but these are replaced with thiazole-based substituents (or benzothiazole-based substituents).
  • thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.
  • the silole derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in JP-A-9-94487.
  • X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, and these may be substituted.
  • the description in the above formula (2) and the description in the above formula (ETM-7-2) can be cited.
  • alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is replaced by alkenyl or alkynyl, respectively.
  • the description in the above formula (ETM-7-2) can be cited.
  • X and Y may combine to form a cycloalkyl ring (and a ring in which a part thereof is unsaturated).
  • a cycloalkyl ring and a ring in which a part thereof is unsaturated.
  • cycloalkyl ring See the description of cycloalkyl in the above formula (2). Can be referred to.
  • R 1 to R 4 are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyl Oxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isothiocyanate, Or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, with adjacent substituents It may form a condensed ring between.
  • alkyl, aryl and alkoxy in R 1 to R 4 in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy are also described above.
  • silyl examples include a silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with aryl, alkyl or cycloalkyl.
  • Tri-substituted silyl is preferable, and triarylsilyl, Trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl and the like can be mentioned.
  • aryl, alkyl and cycloalkyl in these the description in the above formula (2) can be cited.
  • the fused ring formed between adjacent substituents is, for example, a conjugated or non-conjugated fused ring formed between R 1 and R 2 , R 2 and R 3 , R 3 and R 4, and the like.
  • These condensed rings may contain nitrogen, oxygen and sulfur atoms in the ring structure, or may be condensed with another ring.
  • R 1 and R 4 are phenyl groups
  • X and Y are not alkyl or phenyl.
  • R 1 and R 4 are thienyl groups
  • X and Y are alkyl
  • R 2 and R 3 are alkyl, aryl, alkenyl, or R 2 and R 3 combine to form a ring
  • the structure does not simultaneously satisfy cycloalkyl.
  • R 1 and R 4 are silyl groups
  • R 2 , R 3 , X and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms.
  • X and Y are not alkyl or phenyl.
  • silole derivatives can be produced using known raw materials and known synthesis methods.
  • the azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in WO 2017/014226.
  • ⁇ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen of ⁇ has 1 carbon atom.
  • Y is each independently -O-, -S- or> N-Ar
  • Ar is aryl having 6 to 12 carbons or heteroaryl having 2 to 12 carbons
  • at least one hydrogen of Ar May be substituted by alkyl having 1 to 4 carbons, cycloalkyl having 5 to 10 carbons, aryl having 6 to 12 carbons or heteroaryl having 2 to 12 carbons
  • R 1 to R 5 are each independently Is hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, provided that any one of Ar and R 1 to R 5 in> N—Ar is bonded to L Is the part that L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2); Wherein (L-1), X
  • a specific azoline derivative is a compound represented by the following general formula (ETM-16-1) or (ETM-16-2).
  • ⁇ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen of ⁇ has 1 carbon atom.
  • Y is each independently —O—, —S— or> N—Ar
  • Ar is an aryl having 6 to 12 carbons or a heteroaryl having 2 to 12 carbons.
  • Aryl wherein at least one hydrogen of Ar is substituted by alkyl having 1 to 4 carbons, cycloalkyl having 5 to 10 carbons, aryl having 6 to 12 carbons or heteroaryl having 2 to 12 carbons.
  • R 1 to R 4 are each independently hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, provided that R 1 and R 2 are the same.
  • R 3 and R 4 are the same
  • R 1 to R 5 are each independently hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, provided that R 1 and R 2 are the same.
  • L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2);
  • ⁇ is a monovalent group represented by the following formulas ( ⁇ 1-1) to ( ⁇ 1-18), and a divalent group represented by the following formulas ( ⁇ 2-1) to ( ⁇ 2-34).
  • At least one hydrogen of ⁇ is substituted by alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, aryl having 6 to 18 carbons or heteroaryl having 2 to 18 carbons. Is also good.
  • Z in the above formula is> CR 2 ,>N—Ar,> NL, —O— or —S—, and R in> CR 2 is each independently an alkyl having 1 to 4 carbon atoms.
  • R 5 may be a cycloalkyl having 5 to 10 carbons, an aryl having 6 to 12 carbons or a heteroaryl having 2 to 12 carbons, R may be bonded to each other to form a ring, and
  • L is a divalent ring radical selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine.
  • at least one hydrogen of L may be substituted by alkyl having 1 to 4 carbons, cycloalkyl having 5 to 10 carbons, aryl having 6 to 10 carbons or heteroaryl having 2 to 10 carbons.
  • Ar in> N—Ar as Y or Z is from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl
  • At least one hydrogen of Ar selected in> N—Ar as Y may be substituted by alkyl having 1 to 4 carbons, cycloalkyl having 5 to 10 carbons or aryl having 6 to 10 carbons.
  • R 1 to R 4 are each independently hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, provided that R 1 and R 2 are the same, and R 3 and R 4 are the same. 4 is the same, R 1 to R 4 are not all hydrogen at the same time, and m is 1 or 2, and when m is 2, a group formed by an azoline ring and L Are the same.
  • azoline derivative examples include, for example, the following compounds.
  • “Me” in the structural formula represents a methyl group.
  • ⁇ is a divalent group represented by the following formulas ( ⁇ 2-1), ( ⁇ 2-31), ( ⁇ 2-32), ( ⁇ 2-33) and ( ⁇ 2-34). Selected from the group consisting of: wherein at least one hydrogen of ⁇ may be substituted by aryl having 6 to 18 carbon atoms; L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine and triazine, wherein at least one hydrogen of L is alkyl having 1 to 5 carbons, It may be substituted by 10 cycloalkyl, 6-10 carbon aryl or 2-14 carbon heteroaryl, Ar in> N—Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, wherein at least one hydrogen of Ar is alkyl having 1 to 5 carbons
  • R 1 to R 4 are each independently hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, provided that R 1 and R 2 are the same, and R 3 and R 4 are the same And not all of R 1 to R 4 are simultaneously hydrogen, and m is 2 and the groups formed by the azoline ring and L are the same.
  • azoline derivative examples include, for example, the following compounds.
  • “Me” in the structural formula represents a methyl group.
  • This azoline derivative can be produced using a known raw material and a known synthesis method.
  • the electron transport layer or the electron injection layer may further contain a substance capable of reducing a material forming the electron transport layer or the electron injection layer.
  • a substance capable of reducing a material forming the electron transport layer or the electron injection layer various substances are used as long as the substance has a certain reducing property, for example, an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, and an alkali metal.
  • 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 (2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2. eV).
  • Alkaline earth metals such as 9 eV), Sr (2.0 to 2.5 eV) and Ba (2.52 eV), and a substance having a work function of 2.9 eV or less is particularly preferable.
  • a more preferable reducing substance is an alkali metal of K, Rb or Cs, further 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 transporting layer or the electron injecting layer, the emission luminance and the life of the organic EL device can be improved.
  • a reducing substance having a work function of 2.9 eV or less a combination of these two or more kinds of alkali metals is also preferable.
  • a combination containing Cs for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
  • Cs for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred.
  • the cathode 108 plays a role of injecting electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.
  • the material for forming the cathode 108 is not particularly limited as long as it is a substance that 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) -An indium alloy, an aluminum-lithium alloy such as lithium fluoride / aluminum, etc.).
  • lithium, sodium, potassium, cesium, calcium, magnesium or an alloy containing these low work function metals is effective.
  • metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, and vinyl chloride It is preferable to laminate a hydrocarbon polymer compound and the like.
  • 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.
  • ⁇ Binder that may be used in each layer The above materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer can be used alone to form each layer.
  • solvent-soluble resins such as phenolic resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin,
  • Each layer constituting the organic EL element is formed by thinning a material to constitute each layer by a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating or casting, or coating. By doing so, it can be formed.
  • the thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm.
  • the film thickness can usually be measured with a quartz oscillation type film thickness measuring device or the like.
  • the evaporation conditions vary depending on the type of material, the target crystal structure, association structure, and the like of the film.
  • the deposition conditions are as follows: boat heating temperature +50 to + 400 ° C., vacuum degree 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature ⁇ 150 to + 300 ° C., film thickness 2 nm to 5 ⁇ m. It is preferable to set appropriately within the range.
  • an organic EL element including an anode / a hole injection layer / a hole transport layer / a light emitting layer composed of a host material and a dopant material / an electron transport layer / an electron injection layer / a cathode
  • an anode is formed by forming a thin film of an anode material on an appropriate substrate by an evaporation method or the like, 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 thereon 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 a vapor deposition method or the like.
  • a target organic EL device is obtained by forming the cathode. In the production of the above-mentioned organic EL device, 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 obtained in this way, the anode may be applied with a positive polarity and the cathode may be applied with a negative polarity. Light emission 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 waveform of the applied alternating current may be arbitrary.
  • the present invention can be applied to a display device including an organic EL element, a lighting device including an organic EL element, and the like.
  • a display device or a 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 to a known driving device, and includes DC driving, pulse driving, AC driving, and the like. Driving can be performed using a known driving method as appropriate.
  • 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 electroluminescent (EL) display (for example, JP-A-10-335066, JP-A-2003-321546). Gazette, JP-A-2004-281086).
  • the display method of the display includes, for example, at least one of a matrix method and a 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 in a lattice or mosaic, and a set of pixels displays a character or an image.
  • the shape and size of the pixel depend on the application. For example, a square pixel having a side of 300 ⁇ m or less is normally used for displaying images and characters on a personal computer, a monitor, and a television. In the case of a large display such as a display panel, a pixel having a side of mm order is used. become.
  • pixels of the same color may be arranged, but in the case of 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 may be driven by either a line-sequential driving method or an active matrix.
  • Line-sequential driving has the advantage of a simpler structure, but in consideration of operating characteristics, active matrices may be better, so it is necessary to use these differently depending on the application.
  • a pattern is formed so as to display predetermined information, and a predetermined area emits light.
  • a time display and a temperature display on a digital clock or a thermometer an operation state display of an audio device or an electromagnetic cooker, and a panel display of a car.
  • Illumination devices include, for example, illumination devices such as indoor illumination, backlights of liquid crystal display devices, and the like (for example, JP-A-2003-257621, JP-A-2003-277741, and JP-A-2004-119211). Etc.).
  • a backlight is mainly used 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 present embodiment is considered to be difficult to make thin because the conventional method is made up of a fluorescent lamp and a light guide plate.
  • the backlight using the light emitting element according to the above is characterized by being thin and lightweight.
  • the color conversion is to convert light emitted from a light emitter to light having a longer wavelength (wavelength conversion), for example, to convert blue light to green or red light.
  • wavelength conversion wavelength conversion
  • a full-color display can be manufactured by combining such a blue light source and a film having a wavelength conversion function with a white light source as a light source unit and combining it with a liquid crystal driving portion and a color filter.
  • a liquid crystal driving portion it can be used as it is as a white light source, and can be applied as a white light source such as LED lighting.
  • a blue organic EL element as a light source in combination with a film for converting into green and red
  • a full-color organic EL display without using a metal mask can be manufactured.
  • a blue micro LED as a light source in combination with a film for converting into green and red, a low-cost full-color micro LED display can be manufactured.
  • the polycyclic aromatic compound represented by the general formula (1) is useful as a fluorescent material that emits blue light or green light with high color purity by excitation light, and is also used as a material having such a wavelength conversion function. be able to.
  • the polycyclic aromatic compound of the formula (1) converts light having a wavelength of, for example, 300 nm to 449 nm into blue light emission having a narrow half width (25 nm or less, further 20 nm or less) having a maximum value at 450 nm to 500 nm. It can be used as a wavelength conversion material.
  • it can be used as a wavelength conversion material for converting light having a wavelength of 300 nm to 499 nm into green light emission having a narrow half width (25 nm or less, further 20 nm or less) having a maximum value at 500 nm to 570 nm.
  • the obtained solid was purified by a silica gel column (eluent: heptane / toluene mixed solvent), and methyl 4 '-(diphenylamino) -5-methoxy- [1,1'-biphenyl] -2-carboxylate (29. 7 g) were obtained.
  • the ratio of toluene in the eluent was gradually increased with reference to the method described in page 94 of “Chemical Doujinshi (1)-Material handling method and separation and purification method-”.
  • the target substance was eluted with an increase.
  • a solution of tetrahydrofuran (THF, 111.4 ml) in which methyl 4 '-(diphenylamino) -5-methoxy- [1,1'-biphenyl] -2-carboxylate (11.4 g) is dissolved is placed in a water bath. After cooling, a THF solution of methylmagnesium bromide (1.0 M, 295 ml) was added dropwise to the solution. After the addition, the water bath was removed, the temperature was raised to the reflux temperature, and the mixture was stirred for 4 hours.
  • THF tetrahydrofuran
  • the obtained precipitate is washed with water and then methanol, and then purified by a silica gel column (eluent: heptane / toluene mixed solvent) to give 6,6 ′-((2-bromo-1,3-phenylene) Bis (oxy)) bis (9,9-dimethyl-N, N-diphenyl-9H-fluoren-2-amine) (12.6 g) was obtained.
  • the target substance was eluted by gradually increasing the ratio of toluene in the eluent.
  • compound (2-1A-114) was also synthesized from compound (XD-10) according to the following scheme using the same method as in Synthesis Example (D-10) described later.
  • N 1- (2,3-dichlorophenyl) -N 1 , N 3 , N 3 -triphenylbenzene-1,3-diamine (15.0 g)
  • di ([1,1′-biphenyl]- A flask containing (4-yl) amine (10.0 g), Pd-132 (0.2 g), NaOtBu (4.5 g) and xylene (70 ml) was heated and stirred at 120 ° C. for 1 hour. After cooling the reaction solution to room temperature, water and toluene were added thereto to carry out liquid separation. Next, purification was performed using a silica gel short path column (eluent: toluene).
  • yl) -2-chloro -N 3 - phenyl-1,3-diamine (18.5g) - (3- (diphenylamino) phenyl) -N 3.
  • N 1 is (X-D-1), N 1 - Di ([1,1'-biphenyl] -4-yl) -2-chloro -N 3 - (3- (diphenylamino) phenyl) -
  • N 3 -phenylbenzene-1,3-diamine (18.0 g)
  • t-butylbenzene 130 ml
  • 1.7M t-butyllithium pentane was added while cooling in an ice bath under a nitrogen atmosphere.
  • the solution 27.6 ml was added.
  • the temperature was raised to 60 ° C., and the mixture was stirred for 3 hours.
  • Synthesis example (D-4) ⁇ Synthesis of Compound (2-1A-69)> Using the same method as in Synthesis Example (D-2), compound (2-1A-69) was synthesized from compound (XD-3) shown below.
  • Synthesis example (D-6) ⁇ Synthesis of Compound (2-1A-215)> Using the same method as in Synthesis Example (D-2), compound (2-1A-215) was synthesized from compound (XD-5) shown below.
  • Synthesis example (D-7) ⁇ Synthesis of Compound (2-1A-201)> Using the same method as in Synthesis Example (D-2), compound (2-1A-201) was synthesized from compound (XD-6) shown below.
  • Synthesis example (D-8) ⁇ Synthesis of Compound (2-2A-218)> Using the same method as in Synthesis Example (D-2), compound (2-2A-218) was synthesized from compound (XD-7) shown below.
  • 6- (2,3-dibromophenoxy) -9,9-dimethyl-N, N-diphenyl-9H-fluoren-2-amine (10.0 g), di ([1,1′-biphenyl] -4-yl) amine (5.3 g), palladium acetate (0.15 g), dicyclohexyl (2 ', 6'-diisopropoxy- [1,1'-biphenyl] -2-yl) phosphane (0.61 g) ), NaOtBu (2.4 g) and toluene (35 ml) were heated at 80 ° C. for 6 hours.
  • 6- (2-bromo-3- (di ([1,1′-biphenyl] -4-yl) amino) phenoxy) -9,9-dimethyl-N, N-diphenyl-9H-fluorene- 2-Amine (7.9 g) and tetrahydrofuran (42 ml) were placed in a flask, cooled to ⁇ 40 ° C., and a 1.6 M n-butyllithium hexane solution (6 ml) was added dropwise. After completion of the dropwise addition, the mixture was stirred at this temperature for 1 hour, and trimethyl borate (1.7 g) was added. The mixture was heated to room temperature and stirred for 2 hours.
  • the reaction solution was cooled, water was added, and the mixture was filtered to obtain a crude product 1 as a crude product.
  • the organic layer in the filtrate was separated, dried over anhydrous sodium sulfate, the desiccant was removed, and the solvent was distilled off under reduced pressure to obtain a solid as crude product 2.
  • the crude product 1 and the crude product 2 were combined and subjected to short column purification (solvent: toluene) using silica gel. Thereafter, the resultant was washed with methanol, recrystallized from toluene, and further purified by sublimation to obtain 2.63 g (yield: 44%) of a compound (3-1-1).
  • the glass transition temperature (Tg) of compound (3-1-1) was 97.3 ° C.
  • the glass transition temperature is a value measured at a cooling rate of 200 ° C./Min and a heating rate of 10 ° C./Min using a measuring device: Diamond DSC (manufactured by PERKIN-ELMER). The glass transition temperatures of the subsequent compounds were measured in the same manner.
  • the structure of the compound (3-1-301) was confirmed by MS spectrum and NMR measurement.
  • 1 H-NMR (CDCl 3 ): ⁇ 7.91 to 7.89 (m, 2H), 7.72 to 7.70 (m, 2H), 7.66 (d, 1H), 7.63 to 7.47 (m, 7H), 7.40 to 7.18 (m, 14H).
  • the glass transition temperature (Tg) of the compound (3-1-301) was 110.1 ° C.
  • the structure of the compound (3-1-307) was confirmed by MS spectrum and NMR measurement.
  • 1 H-NMR (CDCl 3 ): ⁇ 7.99 to 7.97 (m, 3H), 7.92 (d, 1H), 7.88 (d, 3H), 7.84 (d, 2H) , 7.75-7.73 (m, 3H), 7.64-7.61 (m, 3H), 7.58-7.32 (m, 23H).
  • the glass transition temperature (Tg) of the compound (3-1-307) was 147.6 ° C.
  • the structure of the compound (3-1-560) was confirmed by MS spectrum and NMR measurement.
  • 1 H-NMR (CDCl 3 ): ⁇ 7.96 (s, 1H), 7.92 (d, 2H), 7.85 to 7.81 (m, 2H), 7.78 (d, 1H) , 7.73 to 7.68 (m, 3H), 7.63 to 7.54 (m, 5H), 7.51 to 7.47 (m, 4H), 7.42 to 7.28 (m, 3H) 7H), 7.18 to 7.16 (m, 3H).
  • the glass transition temperature (Tg) of the compound (3-1-560) was 116.6 ° C.
  • organic EL devices were manufactured, and drive voltage (V), emission wavelength (nm), CIE chromaticity (x, y), and external quantum efficiency (%), which are characteristics at 1000 cd / m 2 emission, respectively. , And the time during which 90% or more of the initial luminance was maintained (hereinafter, simply referred to as “90% life”) was measured.
  • the quantum efficiency of a light-emitting device includes an internal quantum efficiency and an external quantum efficiency.
  • the internal quantum efficiency is such that external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting device is purely converted into photons. Shows the ratio of
  • the external quantum efficiency is calculated based on the amount of this photon emitted to the outside of the light emitting element, and part of the photon generated in the light emitting layer is continuously absorbed or reflected inside the light emitting element. As a result, the external quantum efficiency is lower than the internal quantum efficiency because the external quantum efficiency is not emitted outside the light emitting element.
  • the measuring method of the external quantum efficiency is as follows. Using a voltage / current generator R6144 manufactured by Advantest, a voltage at which the luminance of the element was 1000 cd / m 2 was applied to cause the element to emit light. Using a spectral radiance meter SR-3AR manufactured by TOPCON, the spectral radiance in the visible light region was measured from the direction perpendicular to the light emitting surface. Assuming that the light emitting surface is a perfect diffusion surface, the value obtained by dividing the measured value of the spectral radiance of each wavelength component by the wavelength energy and multiplying by ⁇ is the number of photons at each wavelength.
  • the external quantum efficiency is a value obtained by dividing a value obtained by dividing an applied current value by an elementary charge as the number of carriers injected into the device and dividing the total number of photons emitted from the device by the number of carriers injected into the device.
  • HI the material of the hole injection layer 1 is N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′- Biphenyl] -4,4′-diamine
  • HAT-CN the material of the hole injection layer 2 is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile
  • HT -1 (the material of the hole transport layer 1) is N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazole- 3-yl) phenyl) -9H-fluoren-2-amine
  • HT-2 the material of the hole transport layer 2 is N, N-bis (4- (dibenzo [b, d] furan-4 -Y
  • the electron transporting material a material selected from “ET-1”, “ET-2”, “ET-3” and “Liq” represented by the following formula is used.
  • the transport layer material is 4- (3- (4- (10-phenylanthracen-9-yl) naphthalen-1-yl) phenyl) pyridine, and “ET-2” is 9,9 ′-(5 — (6- (1,1′-biphenyl) -4-yl) -2-phenylpyrimidin-4-yl) -1,3-phenylene] bis (9H-carbazole), and “ET-3” is 3 , 3 '-[(2-phenylanthracene-9,10-diyl) dibenzene-4,1-diyl] dipyridine.
  • the chemical structure is shown below together with “Liq” and “Compound (3-15)” used as a host in Example 1.
  • Example 1 ⁇ Device using compound (3-15) as host and compound (2-1A-114) as dopant> A 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate (manufactured by OptoScience Inc.), which was formed by polishing ITO formed to a thickness of 180 nm by sputtering to 150 nm, was used as a transparent support substrate.
  • This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Nagasu Sangyo Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, compound (3-15), compound (2-1A) -114), and a tantalum deposition boat containing ET-1 and an aluminum nitride deposition boat containing Liq, magnesium and silver, respectively.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the pressure in the vacuum chamber was reduced to 5 ⁇ 10 ⁇ 4 Pa, and first, HI was heated and vapor-deposited to a thickness of 40 nm to form the hole injection layer 1.
  • the HAT-CN was heated and vapor-deposited so as to have a thickness of 5 nm to form the hole injection layer 2.
  • HT-1 was heated and vapor-deposited to a thickness of 15 nm to form a hole transport layer 1.
  • HT-2 was heated and evaporated to a thickness of 10 nm to form a hole transport layer 2.
  • the compound (3-15) and the compound (2-1A-114) obtained as described above were simultaneously heated and evaporated to a thickness of 20 nm to form a light emitting layer.
  • the deposition rate was adjusted such that the mass ratio of the compound (3-15) to the compound (2-1A-114) became about 98: 2.
  • ET-1 and Liq were simultaneously heated and evaporated to a thickness of 25 nm to form an electron transport layer.
  • the deposition rate was adjusted so that the mass ratio between ET-1 and Liq was approximately 50:50.
  • the deposition rate of each layer was 0.01 to 1 nm / sec.
  • Liq is heated to be deposited at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then magnesium and silver are simultaneously heated to be deposited to a thickness of 100 nm.
  • a cathode was formed to obtain an organic EL device.
  • the deposition rate was adjusted between 0.1 and 10 nm / sec so that the atomic ratio of magnesium to silver was 10: 1.
  • the driving voltage was 3.7 V and the external quantum efficiency was 7.3%.
  • an organic EL device was manufactured in the following procedure.
  • a 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate manufactured by OptoScience Corp.
  • ITO formed to a thickness of 180 nm by sputtering was polished to 150 nm
  • This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH-1, and the hosts described in Tables 1 to 4 were used.
  • the following layers were sequentially formed on the ITO film of the transparent support substrate.
  • the pressure in the vacuum chamber was reduced to 5 ⁇ 10 ⁇ 4 Pa, and first, HI was heated and vapor-deposited to a thickness of 40 nm to form the hole injection layer 1.
  • the HAT-CN was heated and vapor-deposited so as to have a thickness of 5 nm to form the hole injection layer 2.
  • HT-1 was heated and vapor-deposited to a thickness of 45 nm to form a hole transport layer 1.
  • HT-2 was heated and evaporated to a thickness of 10 nm to form a hole transport layer 2.
  • the host and the dopants described in Tables 1 to 4 were simultaneously heated and vapor-deposited to a thickness of 25 nm to form a light-emitting layer.
  • the deposition rate was adjusted so that the mass ratio of host to dopant was approximately 98: 2.
  • ET-2 is heated and vapor-deposited to a thickness of 5 nm to form an electron transporting layer 1
  • ET-2 and Liq are simultaneously heated and vapor-deposited to a thickness of 25 nm.
  • an electron transport layer 2 was formed.
  • the deposition rate was adjusted so that the mass ratio between ET-2 and Liq was approximately 50:50.
  • the deposition rate of each layer is 0.01 to 1 nm / sec.
  • LiF is heated to deposit a film at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum is heated to deposit a film to a thickness of 100 nm to form a cathode.
  • organic EL devices were obtained.
  • Tables 1 to 4 show materials of each layer of the organic EL elements manufactured in Examples 2 to 66.
  • an organic EL device including a light emitting layer containing a polycyclic aromatic compound having a specific structure and an anthracene compound, the emission half width is narrow, the driving voltage is low, and the quantum efficiency is low.
  • the emission half width is narrow, the driving voltage is low, and the quantum efficiency is low.
  • a device with a long lifetime can be obtained by using a deuterated anthracene-based compound.
  • REFERENCE SIGNS LIST 100 organic electroluminescent element 101 substrate 102 anode 103 hole injection layer 104 hole transport layer 105 light emitting layer 106 electron transport layer 107 electron injection layer 108 cathode

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Abstract

L'invention concerne un élément électroluminescent organique ayant une paire d'électrodes, comprenant une électrode positive et une électrode négative, et une couche électroluminescente disposée entre la paire d'électrodes, la couche électroluminescente contenant un composé d'anthracène et au moins l'un des composés aromatiques polycycliques représentés par la formule générale (1) et des multimères de ceux-ci. L'élément électroluminescent organique présente des caractéristiques d'émission de lumière optimales. (Dans la formule (1), les cycles A à C sont des cycles aryle, etc., Y1 désigne B (bore), et X1 et X2 représentent > O ou > N-R).
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CN112961174A (zh) * 2021-02-05 2021-06-15 吉林奥来德光电材料股份有限公司 一种多环芳族化合物及其制备方法和应用
WO2021122740A1 (fr) * 2019-12-19 2021-06-24 Merck Patent Gmbh Composés polycycliques pour dispositifs électroluminescents organiques
CN113024587A (zh) * 2021-03-12 2021-06-25 吉林奥来德光电材料股份有限公司 含硼和氮的稠合芳香族衍生物及其的制备方法和有机电致发光器件
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JP7506168B2 (ja) 2020-03-23 2024-06-25 エスエフシー カンパニー リミテッド 多環芳香族誘導体化合物及びこれを用いた有機発光素子
CN114181094A (zh) * 2020-09-15 2022-03-15 材料科学有限公司 有机化合物及包含有机化合物的有机电致发光元件
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WO2022086125A1 (fr) * 2020-10-19 2022-04-28 에스에프씨 주식회사 Dispositif électroluminescent organique
CN112961174A (zh) * 2021-02-05 2021-06-15 吉林奥来德光电材料股份有限公司 一种多环芳族化合物及其制备方法和应用
CN113024587A (zh) * 2021-03-12 2021-06-25 吉林奥来德光电材料股份有限公司 含硼和氮的稠合芳香族衍生物及其的制备方法和有机电致发光器件
WO2023043044A1 (fr) * 2021-09-14 2023-03-23 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
WO2024094592A2 (fr) 2022-11-01 2024-05-10 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2024132892A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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