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WO2018034242A1 - Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique Download PDF

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WO2018034242A1
WO2018034242A1 PCT/JP2017/029157 JP2017029157W WO2018034242A1 WO 2018034242 A1 WO2018034242 A1 WO 2018034242A1 JP 2017029157 W JP2017029157 W JP 2017029157W WO 2018034242 A1 WO2018034242 A1 WO 2018034242A1
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carbon atoms
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Inventor
裕基 中野
祐一 西前
匡 羽毛田
河村　昌宏
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence element, an organic electroluminescence element, and an electronic device.
  • an organic electroluminescence element (organic EL element) is composed of an anode, a cathode, and an organic thin film layer including one or more layers sandwiched between the anode and the cathode.
  • the organic thin film layer includes a light emitting layer, and exciton energy generated by recombination of holes and electrons injected into the light emitting layer is converted into light emission.
  • the light emitting layer is a host / dopant light emitting layer in which a host material is doped with a light emitting material (dopant material).
  • a host material is doped with a light emitting material (dopant material).
  • excitons can be efficiently generated from the charge injected into the host. And the energy of the produced
  • Patent Document 1 describes a compound in which indole is essential to be condensed at the 2,3-position of phenanthrene.
  • Patent Document 2 is a compound in which indole is condensed at the 2,3-position of phenanthrene, and Patent Document 3 is indispensable that benzofuran or benzothiophene is condensed at the 2,3-position of phenanthrene.
  • Patent Document 4 describes a compound in which it is essential that benzofuran, benzothiophene, or other heterocycle is condensed at the 2,3-position of phenanthrene. It is described that the compounds described in Patent Documents 2 to 4 can be used as host materials for phosphorescent organic EL devices.
  • the present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a novel compound that can realize an organic EL device having good characteristics.
  • the present invention provides a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)). ((Where The broken lines indicate adjacent groups R 1 and R 2 included in A, adjacent groups R 3 and R 4 included in B, adjacent groups R 5 and R 6 included in C, and adjacent groups R 7 and R 8 included in D.
  • Each adjacent group selected from the adjacent groups R 9 and R 10 contained in E may or may not be bonded to the group represented by the formula (2) or (3);
  • the adjacent group contained in one selected from A to E is bonded to the group represented by the formula (2);
  • the adjacent groups contained in 1 to 4 groups selected from the remaining A to E are each independently bonded to the group represented by the formula (3);
  • When the adjacent group is bonded to the group represented by the formula (2) one of the adjacent groups is bonded to * 1, and the other is bonded to * 2.
  • the adjacent group is bonded to the group represented by the formula (3), one of the adjacent groups is bonded to * 3, and the other is bonded to * 4.
  • R 1 to R 10 represent a bond bonded to * 1, * 2, * 3 or * 4 when bonded to a group represented by the formula (2) or (3);
  • R 1 to R 10 each independently represent a hydrogen atom or a substituent when not bonded to the group represented by the formula (2) or (3), and two adjacent groups are bonded to each other,
  • the aliphatic heterocyclic ring may be formed. However, it excludes when forming group represented by Formula (2) or (3).
  • X is O, S, or NL 1 -R 15 ;
  • L 1 is a single bond or a linking group;
  • R 15 is a hydrogen atom or a substituent,
  • R 11 to R 14 are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms,
  • a group heterocycle may be formed,
  • Y is O, S, NL 2 -R 25 , or CR 26 R 27 ;
  • L 2 is a single bond or a linking group,
  • R 25 is a hydrogen atom or a substituent
  • An aliphatic heterocyclic ring having 5 to 18 ring atoms may be formed, R 21 to R 24 are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic ring having 6 ring atoms A group heterocycle may be formed. ))
  • the present invention provides a material for an organic electroluminescence device comprising the compound (1).
  • the present invention is an organic electroluminescent device comprising a cathode, an anode, and an organic thin film layer disposed between the cathode and the anode, wherein the organic thin film layer includes one or more layers.
  • the organic thin film layer includes a light emitting layer, and at least one of the organic thin film layers provides an organic electroluminescence device including the compound (1).
  • the present invention provides an electronic device comprising the organic electroluminescence element.
  • Compound (1) can realize an organic EL device having good characteristics.
  • the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
  • atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.
  • unsubstituted ZZ group in the case of “substituted or unsubstituted ZZ group” means that the hydrogen atom of the ZZ group is not substituted with a substituent.
  • hydroxogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • the “ring-forming carbon number” means the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among the constituent atoms.
  • the carbon contained in the substituent is not included in the ring-forming carbon.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • a benzene ring has 6 ring carbon atoms
  • a naphthalene ring has 10 ring carbon atoms
  • a pyridine ring has 5 ring carbon atoms
  • a furan ring has 4 ring carbon atoms.
  • the carbon number of the alkyl group is not included in the number of ring-forming carbons.
  • the carbon number of the fluorene ring as a substituent is not included in the ring-forming carbon number.
  • the “number of ring-forming atoms” means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, or a carbocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
  • a heterocyclic compound represents the number of atoms constituting the ring itself.
  • An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
  • an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • the hydrogen atoms bonded to the ring-forming carbon atoms of the pyridine ring and quinazoline ring and the atoms constituting the substituent are not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirobifluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
  • an arbitrary substituent referred to as “substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; A cycloalkyl group having a number of 3 to 50, preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6, and a ring forming carbon number of 6 to 50, preferably 6 to 25, more preferably 6 to 18.
  • An aryl group an aralkyl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 25, more preferably 6 to 18 carbon atoms, and an aryl group having 7 to 51 carbon atoms, preferably 7 to 30 carbon atoms, and more preferably 7 to 20 carbon atoms;
  • An amino group selected from an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, and an aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms.
  • the optional substituent is more preferably an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 carbon atoms.
  • the compound which concerns on 1 aspect of this invention is represented by Formula (1). ((Where The broken lines indicate adjacent groups R 1 and R 2 included in A, adjacent groups R 3 and R 4 included in B, adjacent groups R 5 and R 6 included in C, and adjacent groups R 7 and R 8 included in D.
  • Each adjacent group selected from the adjacent groups R 9 and R 10 contained in E may or may not be bonded to the group represented by the formula (2) or (3);
  • the adjacent group contained in one selected from A to E is bonded to the group represented by the formula (2);
  • the adjacent groups contained in 1 to 4 groups selected from the remaining A to E are each independently bonded to the group represented by the formula (3);
  • When the adjacent group is bonded to the group represented by the formula (2) one of the adjacent groups is bonded to * 1, and the other is bonded to * 2.
  • the adjacent group is bonded to the group represented by the formula (3), one of the adjacent groups is bonded to * 3, and the other is bonded to * 4.
  • R 1 to R 10 represent a bond bonded to * 1, * 2, * 3 or * 4 when bonded to a group represented by the formula (2) or (3);
  • R 1 to R 10 each independently represent a hydrogen atom or a substituent when not bonded to the group represented by the formula (2) or (3), and two adjacent groups are bonded to each other,
  • the aliphatic heterocyclic ring may be formed. However, it excludes when forming group represented by Formula (2) or (3).
  • X is O, S, or NL 1 -R 15 ;
  • L 1 is a single bond or a linking group;
  • R 15 is a hydrogen atom or a substituent,
  • R 11 to R 14 are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms,
  • a group heterocycle may be formed,
  • Y is O, S, NL 2 -R 25 , or CR 26 R 27 ;
  • L 2 is a single bond or a linking group,
  • R 25 is a hydrogen atom or a substituent
  • An aliphatic heterocyclic ring having 5 to 18 ring atoms may be formed, R 21 to R 24 are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic ring having 6 ring atoms A group heterocycle may be formed. ))
  • Compound (1) includes compounds represented by the following formulas (10-1) to (10-16).
  • formulas (10-1) to (10-16) the curves shown by solid lines indicate that the adjacent groups contained in A to E are bonded to the groups represented by formula (2) or (3), respectively. Indicates that a ring is formed.
  • the compound (1) is preferably represented by the formulas (10-2), (10-6), (10-7), (10-11), (10-13), (10-14) ) And (10-16), more preferably the formulas (10-6), (10-7), (10-11), (10-13), (10-14) and (10 -16), more preferably represented by any one of formulas (10-11), (10-13), (10-14) and (10-16), and particularly preferably represented by formula (10-16). ⁇ 13), (10-14) and (10-16).
  • the compound (1) is represented by the formula (20) or (30). (Wherein R 1 to R 4 , R 7 to R 10 , R 11 to R 14 , and X are as described above, and a curve indicated by a broken line is a group selected from A, B, D, and E 1 to (It represents that the adjacent groups contained in each of the four are independently bonded to the group represented by the formula (3).)
  • the compound represented by the formula (20) includes compounds represented by the formulas (20-1) to (20-15).
  • the curves shown by solid lines are represented by the formula (3) in which the adjacent groups contained in each of A, B, D, and E are independently represented. Represents a bond to a group.
  • the compound represented by the formula (20) is represented by the formula (20-3), (20-6), (20-9), (20-10), (20-12), (20-14), or ( 20-15) is preferable, and a formula (20-20) or (20-21) is particularly preferable.
  • the compound represented by the formula (30) includes compounds represented by the formulas (30-1) to (30-15).
  • the curves shown by solid lines are represented by the formula (3) in which the adjacent groups contained in each of A, B, D, and E are independently represented. Represents bonding to a group.
  • the compound represented by the formula (30) is represented by the formula (30-3), (30-6), (30-9), (30-10), (30-12), (30-14), or ( 30-15), and particularly preferably represented by the formula (30-20) or (30-21).
  • the compound (1) is represented by the formula (40), (50) or (60).
  • R 1 to R 10 , R 11 to R 14 , and X are as described above
  • the curve indicated by a broken line shows that each of the adjacent groups contained in 1 to 4 selected from A to C and E is independently represented by the formula (3).
  • the curve indicated by the broken line shows that the adjacent groups contained in each of 1 to 4 selected from A to D are independently bonded to the group represented by the formula (3).
  • the compound represented by the formula (40) includes compounds represented by the formulas (40-1) to (40-15).
  • the curves indicated by solid lines are represented by the formula (3) in which the adjacent groups contained in each of A, B, C, and E are independently represented. Represents a bond to a group.
  • the compound represented by the formula (40) is represented by the formula (40-2), (40-9), (40-10), (40-11), (40-13), (40-14), or ( 40-15), and particularly preferably represented by any one of formulas (40-20) to (40-23).
  • the compound represented by the formula (50) includes compounds represented by the formulas (50-1) to (50-15).
  • the adjacent groups contained in each of A, B, C and E are each independently represented by the formula (3). Represents a bond to a group.
  • the compound represented by the formula (50) is represented by the formula (50-2), (50-9), (50-10), (50-11), (50-13), (50-14), or ( 50-15) and particularly preferably any one of formulas (50-20) to (50-23).
  • the compound represented by the formula (60) includes compounds represented by the formulas (60-1) to (60-15).
  • the adjacent groups contained in each of A, B, C and D are independently represented by the formula (3). Represents a bond to a group.
  • the compound represented by the formula (60) is preferably represented by any one of the formulas (60-12) to (60-15).
  • the compound (1) is represented by the formula (70) or (80).
  • R 1 to R 4 , R 7 to R 10 , R 21 to R 24 , and Y are as described above, and the curve indicated by a broken line is one selected from A, B, D, and E
  • That the adjacent group contained in is bonded to the group represented by the formula (2), and the adjacent groups contained in the remaining 1 to 3 are each independently represented by the formula (3). It represents that it is bonded to the group.
  • the curves shown by broken lines are included in the adjacent groups R 1 and R 2 included in A, the adjacent groups R 3 and R 4 included in B, and the adjacent groups R 5 and R 6 and D included in C.
  • Each adjacent group selected from the adjacent groups R 7 and R 8 and the adjacent groups R 9 and R 10 contained in E may be bonded to or bonded to the group represented by the formula (2) or (3) Indicates that you do not have to.
  • two groups selected from R 2 and R 3 , R 4 and R 5 , R 6 and R 7 , R 8 and R 9 , and R 10 and R 1 are represented by the formula (2) or (3 ) Or a group represented by the formula (2) or (3).
  • the central phenanthrene structure at the 2nd and 3rd positions, the 4th and 5th positions, the 6th and 7th positions, the 8th and 9th positions, and the 10th and 1st positions, The group represented by 3) is not bonded.
  • the adjacent group contained in one selected from A to D is preferably bonded to the group represented by the formula (2), and the adjacent group contained in B or C is represented by the formula It is more preferable to bond to the group represented by (2).
  • the adjacent groups contained in 1 to 3 selected from A to D are independently bonded to the group represented by the formula (3), and A, B More preferably, the adjacent groups contained in 1 to 3 groups selected from A and C or A, C and D are each independently bonded to the group represented by the formula (3).
  • the adjacent group contained in one of B or C is bonded to the group represented by the formula (2), and the other of B or C, 1-3 selected from A and D It is preferable that the adjacent groups included are each independently bonded to the group represented by the formula (3), and the adjacent groups included in one or two selected from A and D are each independently More preferably, it is bonded to a group represented by the formula (3).
  • the group represented by the formula (2) and the group represented by the formula (3) are preferably bonded to benzene rings having different central phenanthrene structures.
  • R 1 to R 10 represent a bond bonded to * 1, * 2, * 3 or * 4 when bonded to the group represented by the formula (2) or (3). That is, the group represented by the formula (2) and the group represented by the formula (3) are directly bonded to the benzene ring of the central phenanthrene structure.
  • R 1 to R 10 each independently represent a hydrogen atom or a substituent when not bonded to the group represented by the formula (2) or (3).
  • Two adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 5 to 18 ring atoms, or A substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms may be formed. However, it excludes when forming group represented by Formula (2) or (3). In one embodiment of the present invention, two adjacent substituents are not bonded to each other and thus do not have to form a ring. In another embodiment of the present invention, R 1 to R 10 that are not bonded to the group represented by formula (2) or (3) are preferably hydrogen atoms.
  • the substituent represented by R 1 to R 10 is an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms, and more preferably.
  • Mono-substituted, di-substituted or tri-substituted silyl groups having a substituent having a substituent; a haloalkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, and more A haloalkoxy group preferably having 1 to 8 haloalkyl groups; an aromatic or non-aromatic heterocyclic group having 5 to 50, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms Is a group selected from and nitro group, a halogen atom, a cyano group.
  • the above substituent may be further substituted with the above-described substituent.
  • the substituent represented by R 1 to R 10 is preferably an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms. More preferably 3 to 8, more preferably 5 or 6 cycloalkyl group; ring-forming carbon number 6 to 50, preferably 6 to 25, more preferably 6 to 18 aryl group; carbon number 1 to 50, preferably Is mono- or di-substituted having a substituent selected from an alkyl group having 1 to 18, more preferably 1 to 8 and an aryl group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms.
  • it is selected from 6-18 aryl groups; 5-50 ring-forming atoms, preferably 5-24, more preferably 5-13 aromatic heterocyclic groups; and cyano groups.
  • alkyl group having 1 to 50 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (isomers).
  • Group, s-butyl group, t-butyl group, and pentyl group (including isomer group) are preferable, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group Group and t-bu More preferably group, further preferably a methyl group and t- butyl group.
  • Examples of the cycloalkyl group having 3 to 50 ring carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • Examples of the aryl group having 6 to 50 ring carbon atoms include phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, acenaphthylenyl group, anthryl group, benzoanthryl group, aceanthryl group, phenanthryl group, benzophenyl group, Examples include nantril group, phenalenyl group, fluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzocrisenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, and perylenyl group.
  • a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group are preferable, a phenyl group, a biphenylyl group, and a naphthyl group are more preferable, and a phenyl group is more preferable.
  • As the substituted aryl group having 6 to 50 ring carbon atoms 9,9-dimethylfluorenyl group and 9,9-diphenylfluorenyl group are preferable.
  • the aryl group having 6 to 50 ring carbon atoms contained in the aralkyl group having 7 to 51 carbon atoms is the same as the aryl group having 6 to 50 ring carbon atoms, and the alkyl part of the aralkyl group has The alkyl group is selected so as to satisfy 7 to 51.
  • Examples of the aralkyl group having 7 to 51 carbon atoms include a benzyl group, a phenethyl group, and a phenylpropyl group, and a benzyl group is preferable.
  • the mono- or di-substituted amino group has an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, and the alkyl group having 1 to 50 carbon atoms and the ring group having 6 to 50 carbon atoms. This is the same as the aryl group.
  • Examples of the mono- or di-substituted amino group include a dialkylamino group, a diarylamino group, and an alkylarylamino group.
  • the alkyl group having 1 to 50 carbon atoms contained in the alkoxy group is the same as the alkyl group having 1 to 50 carbon atoms.
  • a t-butoxy group, a propoxy group, an ethoxy group, and a methoxy group are preferable, an ethoxy group and a methoxy group are more preferable, and a methoxy group is more preferable.
  • the aryl group having 6 to 50 ring carbon atoms contained in the aryloxy group is the same as the aryl group having 6 to 50 ring carbon atoms.
  • a terphenyloxy group, a biphenyloxy group, and a phenoxy group are preferable, a biphenyloxy group and a phenoxy group are more preferable, and a phenoxy group is more preferable.
  • the mono-substituted, di-substituted, or tri-substituted silyl group has an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, and the alkyl group having 1 to 50 carbon atoms and the ring group having 6 to 50 carbon atoms. This is the same as the aryl group.
  • Tri-substituted silyl groups are preferred, for example, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, triphenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group, And tolylylsilyl group.
  • the haloalkyl group having 1 to 50 carbon atoms is at least one of the above alkyl groups having 1 to 50 carbon atoms, preferably 1 to 7 hydrogen atoms, or all hydrogen atoms are fluorine atoms, chlorine atoms, bromine atoms. And a group obtained by substitution with a fluorine atom, preferably a fluoroalkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms.
  • a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group are more preferable, and a pentafluoroethyl group, 2,2,2-trifluoroethyl group is more preferable. And a trifluoromethyl group are more preferable, and a trifluoromethyl group is particularly preferable.
  • the haloalkyl group having 1 to 50 carbon atoms of the haloalkoxy group is the same as the haloalkyl group having 1 to 50 carbon atoms, and has 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms.
  • a fluoroalkoxy group is preferred, a heptafluoropropoxy group (including isomers), a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, and a trifluoromethoxy group are more preferred, and a pentafluoroethoxy group, 2,2 , 2-trifluoroethoxy group and trifluoromethoxy group are more preferable, and trifluoromethoxy group is particularly preferable.
  • the aromatic or non-aromatic heterocyclic group having 5 to 50 ring atoms is 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring-forming heteroatoms such as nitrogen atom, sulfur Includes atoms and oxygen atoms.
  • the aromatic heterocyclic group include pyrrolyl, furyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl Group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group, isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group (benzothienyl group, the same shall apply hereinafter), indolizinyl group, quinolidinyl
  • substituted heteroaryl group examples include N-phenylcarbazolyl group, N-biphenylylcarbazolyl group, N-phenylphenylcarbazolyl group, N-naphthylcarbazolyl group, phenyldibenzofuranyl group, And a phenyldibenzothiophenyl group (phenyldibenzothienyl group) is preferable.
  • a non-aromatic heterocyclic group the group which hydrogenated the aromatic ring of the said aromatic heterocyclic group, and converted into the aliphatic ring is mentioned, for example.
  • the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and a fluorine atom is preferred.
  • Examples of the aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms include cyclopentene, cyclopentadiene, cyclohexene, cyclohexadiene, and biphenylene, naphthalene, acenaphthylene, anthracene, benzoanthracene, aceanthrylene, phenanthrene, benzo Examples include phenanthrene, phenalene, fluorene, pyrene, chrysene, s-indacene, as-indacene, fluoranthene and the like, which are obtained by hydrogenating an aromatic ring of an aromatic hydrocarbon having 6 to 18 carbon atoms and converting it into an aliphatic ring. It is done.
  • aromatic heterocyclic ring having 5 to 18 ring atoms examples include pyrrole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazoline, oxazole, thiazole, pyrazole, isoxazole, isothiazole, oxadi Azole, thiadiazole, triazole, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, benzoxazole, benzothiazole, indazole, benzisoxa Sol, benzoisothiazole, dibenzofuran, naphthobenzofuran, dibenzothiophene, naphtho
  • Examples of the aliphatic heterocyclic ring having 5 to 18 ring atoms include a ring obtained by hydrogenating an aromatic ring of the aromatic heterocyclic ring having 5 to 18 ring atoms and converting it to an aliphatic ring.
  • X represents O, S, or NL 1 -R 15 , preferably NL 1 -R 15
  • L 1 is a single bond or a linking group
  • R 15 is a hydrogen atom or It is a substituent.
  • L 1 is preferably a single bond, and in another embodiment, L 1 is preferably a linking group.
  • R 15 is preferably a hydrogen atom, and in another embodiment, R 15 is preferably a substituent.
  • the linking group represented by L 1 is a substituted or unsubstituted arylene group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring forming carbon atoms, or a substituted or unsubstituted ring forming carbon atom number of 5 to 50, preferably Is a heteroarylene group of 5 to 24, more preferably 5 to 13.
  • the arylene group is a divalent group obtained by removing one hydrogen atom from an aryl group having 6 to 50 ring carbon atoms described for R 1 to R 10
  • the heteroarylene group is R 1 to R 10.
  • L 1 is preferably an arylene group having 6 to 50 ring carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms, more preferably a phenylene group (including an isomer group), a biphenylene group (an isomer group). A terphenylene group (including an isomer group).
  • the substituent represented by R 15 is the same as the substituent described for R 1 to R 10 , and is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted ring group having 6 to 50 carbon atoms.
  • the group is preferably selected from the group, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. It is more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • aryl group examples include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzoanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, Examples include fluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrycenyl group, benzocricenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, and perylenyl group.
  • Phenyl group, biphenylyl group , A terphenylyl group, and a naphthyl group are preferable, a phenyl group, a biphenylyl group, and a naphthyl group are more preferable, and a phenyl group and a p-, m-, or o-biphenylyl group are more preferable.
  • R 11 to R 14 are each independently a hydrogen atom or a substituent. In one embodiment of the present invention, R 11 to R 14 are preferably hydrogen atoms.
  • the substituents represented by R 11 to R 14 are the same as the substituents described for R 1 to R 10 .
  • Two adjacent groups selected from R 11 to R 14 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 18 carbon atoms.
  • substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms or a substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms.
  • the substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 carbon atoms and the substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms are as described for R 1 to R 10. is there.
  • Examples of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms include benzene, biphenylene, naphthalene, acenaphthylene, anthracene, benzoanthracene, aceanthrylene, phenanthrene, benzophenanthrene, phenalene, fluorene, and pyrene. , Chrysene, s-indacene, as-indacene, fluoranthene and the like.
  • Examples of the substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms include pyridine, pyrazine, pyridazine, pyrimidine, oxazine, and thiazine.
  • two adjacent groups selected from R 11 to R 14 are not bonded to each other and thus do not need to form a ring.
  • Y is O, S, NL 2 —R 25 , or CR 26 R 27 , preferably O, S, or NL 2 —R 25 .
  • a compound in which X in formula (2) is NL 2 -R 25 and Y in formula (3) is O, S, NL 2 -R 25 , or CR 26 R 27 is preferred.
  • X is N-L 2 -R 25 of formula (2)
  • Y is O, S, or more preferably a compound which is N-L 2 -R 25 of formula (3)
  • X in formula (2) There are N-L 2 -R 25, compound Y is N-L 2 -R 25 of formula (3) is more preferable.
  • L 2 is a single bond or a linking group. In one embodiment of the present invention, L 2 is preferably a single bond, and in another embodiment, L 2 is preferably a linking group.
  • the linking group represented by L 2 has a substituted or unsubstituted ring-forming carbon number of 6 to 50, preferably 6 to 25, more preferably 6 to 18 arylene group or a substituted or unsubstituted ring forming atom number of 5 to 50, Preferably, it is a heteroarylene group having 5 to 24, more preferably 5 to 13, preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 carbon atoms. is there.
  • the arylene group is a divalent group obtained by removing one hydrogen atom from an aryl group having 6 to 50 ring carbon atoms described for R 1 to R 10 , and the heteroarylene group is R 1 to R 10. And a divalent group obtained by removing one hydrogen atom from an aromatic heterocyclic group having 5 to 50 ring atoms as described for No. 10.
  • L 2 is preferably a phenylene group (including an isomer group), a biphenylene group (including an isomer group), and a terphenylene group (including an isomer group), more preferably a phenylene group (including an isomer group).
  • a biphenylene group (including an isomer group) more preferably an o-, m- or p-phenylene group.
  • R 25 is a hydrogen atom or a substituent. In one embodiment of the present invention, R 25 is preferably a hydrogen atom, and in another embodiment, R 25 is preferably a substituent.
  • the substituent represented by R 25 is the same as the substituents described for R 1 to R 10 , preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted ring carbon number of 6 to A substituted or unsubstituted aryl group having 7 to 51 carbon atoms having an aryl group having 6 to 50 ring carbon atoms; and a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms.
  • the substituted or unsubstituted aryl group include a phenyl group, a biphenylyl group (including an isomer group), a terphenylyl group (including an isomer group), a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, and a benzoan.
  • Tolyl group aceanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzocrisenyl group , S-indacenyl group, as-indacenyl group, fluoranthenyl group and perylenyl group are preferable, phenyl group, biphenylyl group (including isomer group), terphenylyl group (including isomer group), 9,9-dimethyl Fluorenyl group and fluoranthenyl group are more preferred Properly, a phenyl group, p- biphenylyl group, m- biphenylyl group, p- terphenylyl group, 1-9,9- dimethyl fluorenyl group, and 3-flu
  • aromatic heterocyclic group examples include pyrrolyl group, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, Isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group, isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group (benzothienyl group, the same shall apply hereinafter), indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl Group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl
  • R 26 and R 27 are each independently a hydrogen atom or a substituent. In one embodiment of the present invention, R 26 and R 27 are preferably a hydrogen atom, and in another embodiment, R 26 and R 27 are A substituent is preferred.
  • the substituents represented by R 26 and R 27 are the same as the substituents described with respect to R 1 to R 10 , and in particular, an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, An aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 is preferable, and a methyl group, an ethyl group, or a phenyl group is more preferable.
  • R 26 and R 27 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms or a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms. It may be formed.
  • Examples of the aliphatic hydrocarbon ring include cyclopentane, cyclohexane and the like, and examples of the aliphatic heterocycle include imidazolidine, imidazoline, oxazolidine, dioxolane, thiazoline, tetrahydropyran, piperazine, piperidine, pyrazoline, Examples include pyrazolidine, pyrrolidine, pyrroline, tetrahydrofuran, tetrahydrothiophene, morpholine and the like.
  • R 21 to R 24 are each independently a hydrogen atom or a substituent. In one embodiment of the present invention, R 21 to R 24 are preferably hydrogen atoms.
  • the substituents represented by R 21 to R 24 are the same as the substituents described for R 1 to R 10 .
  • Two adjacent groups selected from R 21 to R 24 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 18 carbon atoms.
  • a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms is a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms.
  • the aromatic heterocycle of 6 is as described for R 11 to R 14 .
  • two adjacent groups selected from R 21 to R 24 are not bonded to each other and thus do not need to form a ring.
  • the compound (1) is useful as a material for an organic EL device.
  • the method for producing the compound (1) is not particularly limited, and those skilled in the art can easily produce the compound (1) by utilizing and changing known synthetic reactions with reference to the examples described below.
  • the organic EL element material of the present invention contains the compound represented by the formula (1) (compound (1)).
  • the content of the compound (1) in the organic EL device material of the present invention is not particularly limited, and may be, for example, 1% by mass or more (including 100%), and 10% by mass or more (including 100%). It is preferably 50% by mass or more (including 100%), more preferably 80% by mass or more (including 100%), and 90% by mass or more (including 100%). It is particularly preferred that The material for an organic EL element of the present invention is useful as a material for producing an organic EL element.
  • the fluorescent light emitting unit is also useful as a material for the anode-side organic thin film layer such as a hole transport layer, a hole injection layer, and an electron blocking layer provided between the anode and the light emitting layer.
  • the cathode-side organic thin film layers such as an electron transport layer, an electron injection layer, and a hole blocking layer provided between the cathode and the light emitting layer.
  • the material for an organic EL device of the present invention is preferably used for a phosphorescent light emitting unit, and is preferably used as a host material in a light emitting layer of the phosphorescent light emitting unit.
  • An organic EL element has an organic thin film layer including one or more layers between a cathode and an anode.
  • the organic thin film layer includes a light emitting layer, and at least one of the organic thin film layers includes the compound (1).
  • the organic thin film layer containing the compound (1) include an anode-side organic thin film layer (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer) provided between the anode and the light emitting layer. Etc.), light emitting layer, space layer, cathode side organic thin film layer (electron transport layer, electron injection layer, hole blocking layer, etc.), etc., but are not limited thereto.
  • it can be used as a host material, a dopant material, a hole injection layer material, or a hole transport layer material in the light emitting layer of the fluorescent light emitting unit. Further, it can be used as a host material, a hole injection layer material, and a hole transport layer material in a light emitting layer of a phosphorescent light emitting unit. It is used as a host material in the light emitting layer of a phosphorescent light emitting unit (red or green phosphorescent light emitting device).
  • the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
  • a tandem type having a plurality of light emitting units may be used, and among these, a fluorescent light emitting type element is preferable.
  • the “light emitting unit” includes an organic thin film layer including one or more layers, at least one of which is a light emitting layer, and is a minimum unit that emits light by recombination of injected holes and electrons.
  • typical element configurations of simple organic EL elements include the following element configurations.
  • Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided.
  • a typical layer structure of the simple light emitting unit is shown below. The layers in parentheses are optional.
  • A (hole injection layer /) hole transport layer / fluorescent light emitting layer (/ electron transport layer)
  • B (hole injection layer /) hole transport layer / phosphorescent layer (/ electron transport layer)
  • C (hole injection layer /) hole transport layer / first fluorescent light emitting layer / second fluorescent light emitting layer (/ electron transport layer)
  • D (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
  • E (hole injection layer /) hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
  • F (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • G (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer (/ electron
  • Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
  • the laminated light emitting unit (f) hole injection layer /) hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescence.
  • the layer structure include a light emitting layer (blue light emission) (/ electron transport layer).
  • An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer.
  • a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer.
  • the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
  • the first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units, for example.
  • the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
  • a known material structure to be supplied can be used.
  • FIG. 1 shows a schematic configuration of an example of the organic EL element.
  • the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 10 has at least one light emitting layer 5.
  • Hole injection / transport layer 6 anode-side organic thin film layer
  • electron injection / transport layer 7 cathode-side organic thin film layer
  • an electron barrier layer (not shown) may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5.
  • a host combined with a fluorescent dopant is called a fluorescent host
  • a host combined with a phosphorescent dopant is called a phosphorescent host
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material for forming a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the substrate is used as a support for the organic EL element.
  • a plate made of glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • the flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. .
  • an inorganic vapor deposition film can also be used.
  • Anode As the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
  • a metal an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
  • ITO indium tin oxide
  • indium oxide-tin oxide containing silicon or silicon oxide indium oxide-zinc oxide
  • indium oxide containing tungsten oxide and zinc oxide examples include graphene.
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • a nitride of the metal for example, titanium nitride
  • indium oxide-zinc oxide is a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide is 0.5 to 5 wt. % And a target containing 0.1 to 1 wt% of zinc oxide can be formed by a sputtering method.
  • the hole injection layer formed in contact with the anode is formed using a material that is easy to inject holes regardless of the work function of the anode. Therefore, a material generally used as an electrode material (for example, metal , Alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the Periodic Table of Elements) can be used.
  • a material generally used as an electrode material for example, metal , Alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the Periodic Table of Elements
  • An element belonging to Group 1 or Group 2 of the periodic table which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used.
  • an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these
  • a vacuum evaporation method or a sputtering method can be used.
  • the hole injecting layer is a layer containing a material having a high hole injecting property (hole injecting material).
  • the compound (1) may be used alone or in combination with the following materials for the hole injection layer.
  • molybdenum oxide titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, Silver oxide, tungsten oxide, manganese oxide, or the like can be used.
  • Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
  • poly (N-vinylcarbazole) (abbreviation: PVK)
  • poly (4-vinyltriphenylamine) (abbreviation: PVTPA)
  • PVTPA poly (4-vinyltriphenylamine)
  • PTPDMA poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide]
  • PTPDMA poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine]
  • High molecular compounds such as Poly-TPD
  • a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.
  • acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) in combination with the compound (1).
  • HAT hexaazatriphenylene
  • R 21 to R 26 may be the same as or different from each other, and each independently represents a cyano group, —CONH 2 , carboxyl group, or —COOR 27 (R 27 represents an alkyl group having 1 to 20 carbon atoms or And represents a cycloalkyl group having 3 to 20 carbon atoms, and in R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 , two adjacent groups are bonded to each other to form —CO—.
  • R 27 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the hole transport layer is a layer containing a material having a high hole transport property (hole transport material). You may use the said compound (1) for a positive hole transport layer individually or in combination with the following compound.
  • an aromatic amine compound for example, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and N, N′-bis (3-methylphenyl) -N , N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4,4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ′′ -tris (N, N -
  • the hole-transporting layer includes 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9- Carbazole derivatives such as phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA) and 2-t-butyl-9,10-di (2-naphthyl) anthracene
  • An anthracene derivative such as (abbreviation: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth) may be used.
  • a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly(N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • the layer including a compound having a high hole-transport property may be a single layer or a stacked layer including two or more layers including the above compound.
  • the hole transport layer may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
  • the compound (1) may be contained in either the first hole transport layer or the second hole transport layer.
  • the compound (1) is preferably contained in the first hole transport layer, and in another embodiment, the compound (1) is contained in the second hole transport layer. preferable.
  • the dopant material of a light emitting layer is a layer containing material (dopant material) with high luminescent property, A various material can be used.
  • a fluorescent material or a phosphorescent material can be used as the dopant material.
  • the fluorescent light-emitting material is a compound that emits light from a singlet excited state
  • the phosphorescent material is a compound that emits light from a triplet excited state.
  • pyrene derivatives As a blue fluorescent material that can be used for the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used.
  • N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S)
  • 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA)
  • 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine abbreviation: PCBAPA
  • An aromatic amine derivative or the like can be used as a green fluorescent material that can be used for the light emitting layer.
  • Tetracene derivatives, diamine derivatives and the like can be used as red fluorescent materials that can be used for the light emitting layer.
  • N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used.
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex.
  • FIr6 bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ′, 5′bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium (III ) Picolinate (abbreviation: Ir (CF3ppy) 2 (pic)), bis [2- (4 ′, 6′-difluorophenyl)
  • An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer.
  • red phosphorescent light-emitting material that can be used for the light-emitting layer
  • metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used.
  • iridium complexes bis [2- (2′-benzo [4,5- ⁇ ] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (btp) 2 (acac)), Bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) 2 (acac)), (acetylacetonato) bis [2,3-bis (4-fluoro Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) 2 (acac)), 2,
  • Tb (acac) 3 (Phen) tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation
  • the light-emitting layer may have a configuration in which the above-described dopant material is dispersed in another material (host material).
  • the host material the compound (1) of the present invention is preferable, and various other materials can be used.
  • the lowest unoccupied orbital level (LUMO level) is higher than that of the dopant material, and the highest occupied orbital level (HOMO level). It is preferable to use a material having a low order.
  • Examples of the host material that can be used in combination with the compound (1) of the present invention include (1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; (4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.
  • a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex
  • heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives
  • condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives
  • tris (8-quinolinolato) aluminum (III) (abbreviation: Alq)
  • tris (4-methyl-8-quinolinolato) aluminum (III) abbreviation: Almq3)
  • bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq2)
  • bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) abbreviation: BAlq
  • bis (8-quinolinolato) zinc (II) (abbreviation: Znq )
  • Bis [2- (2-benzoxazolyl) phenolato] zinc (II) abbreviation: ZnPBO
  • bis [2- (2-benzothiazolyl) phenolato] zinc (II) abbreviation: ZnBTZ
  • the electron transport layer is a layer containing a material having a high electron transport property (electron transport material).
  • the compound (1) may be used alone or in combination with the following materials for the electron transport layer.
  • the electron transport layer for example, (1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, (2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, (3) A polymer compound can be used.
  • Examples of the metal complex include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato ) Beryllium (abbreviation: BeBq 2 ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq) ), Bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), and bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ).
  • Alq tris (8-quinolinolato) aluminum
  • Almq3 tris (4-methyl-8-quinolinolato) aluminum
  • heteroaromatic compound for example, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(Pt-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4 -Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4 -Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis (5-methylbenzo
  • polymer compound for example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9, 9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
  • the above materials are mainly materials having an electron mobility of 10 ⁇ 6 cm 2 / Vs or higher. Note that materials other than those described above may be used for the electron-transport layer as long as the material has a higher electron-transport property than the hole-transport property. Further, the electron transport layer is not limited to a single layer, and two or more layers made of the above materials may be stacked.
  • the electron injection layer is a layer containing a material having a high electron injection property.
  • a material having a high electron injection property lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc.
  • Alkali metals, alkaline earth metals, or compounds thereof can be used.
  • a material containing an electron transporting material containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
  • a composite material has an excellent electron injecting property and electron transporting property because the organic compound receives electrons from the electron donor.
  • the organic compound is preferably a material excellent in transporting received electrons.
  • a material (metal complex, heteroaromatic compound, or the like) constituting the above-described electron transport layer is used. be able to.
  • the electron donor may be any material that exhibits an electron donating property with respect to the organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
  • Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • Cathode It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode.
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
  • a vacuum evaporation method or a sputtering method can be used.
  • coating method, the inkjet method, etc. can be used.
  • a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
  • an insulating layer made of an insulating thin film layer may be inserted between the pair of electrodes.
  • the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture or laminate of these may be used.
  • the space layer is, for example, in the case of laminating a fluorescent light emitting layer and a phosphorescent light emitting layer, for the purpose of adjusting the carrier balance so as not to diffuse excitons generated in the phosphorescent light emitting layer into the fluorescent light emitting layer.
  • This is a layer provided between the fluorescent light emitting layer and the phosphorescent light emitting layer.
  • the space layer can be provided between the plurality of phosphorescent light emitting layers. Since the space layer is provided between the light emitting layers, a material having both electron transport properties and hole transport properties is preferable. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.
  • a blocking layer such as an electron blocking layer, a hole blocking layer, or a triplet blocking layer may be provided in a portion adjacent to the light emitting layer.
  • the electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
  • the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer.
  • the triplet blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing into surrounding layers and confining the excitons in the light emitting layer.
  • the compound (1) of the present invention is also suitable as a material for the electron blocking layer and the triplet blocking layer.
  • Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like.
  • the film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, a high driving voltage is required and the efficiency is lowered, so it is usually 5 nm to 10 ⁇ m. 10 nm to 0.2 ⁇ m is more preferable.
  • the organic EL element can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, and a personal computer, and electronic equipment such as a light emitting device for lighting and a vehicle lamp.
  • display devices such as an organic EL panel module
  • display devices such as a television, a mobile phone, and a personal computer
  • electronic equipment such as a light emitting device for lighting and a vehicle lamp.
  • Example 1 Manufacture of EL element A glass substrate with an ITO transparent electrode (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 10 minutes, and then UV ozone cleaning was performed for 30 minutes. The thickness of the ITO transparent electrode was 120 nm.
  • the cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and the following acceptor material (Compound A) was first deposited so as to cover the transparent electrode to form an acceptor layer having a thickness of 5 nm. On this acceptor layer, the following aromatic amine compound (compound B) was vapor-deposited to form a 220 nm-thick hole transport layer.
  • the compound (1) obtained in Synthesis Example 1 and the following compound RD-1 were co-evaporated to form a co-deposited film having a thickness of 40 nm.
  • the concentration of Compound RD-1 was 2.0% by mass.
  • This co-deposited film functions as a light emitting layer.
  • the following compound C (50 mass%) and Liq (50 mass%) which is an electron donating dopant were binary-deposited, and the 25-nm-thick electron carrying layer was formed.
  • Liq was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
  • organic EL element was manufactured. Evaluation of organic EL element The produced organic EL element was made to emit light by direct current drive, and the drive voltage (V) at 10 mA / cm 2 was determined. Further, an 80% lifetime at a current density of 50 mA / cm 2 was determined. The 80% life means the time until the luminance is attenuated to 80% of the initial luminance in constant current driving. The results are shown in Table 1.
  • Comparative Examples 1 and 2 An organic EL device was produced in the same manner as in Example 1 except that the comparative compound (1) or (2) was used in place of the compound (1), and the driving voltage (V) was 80% as in Example 1. Lifespan was measured. The results are shown in Table 1.
  • the compound (1) corresponds to a compound obtained by crosslinking one carbazole structure benzene ring and the other carbazole structure benzene ring of the comparative compound (1). From Table 1, it can be seen that the organic EL device using the compound (1) has a lower driving voltage and longer life than the organic EL device using the comparative compound (1). In addition, the EL device using the comparative compound (2) having a structure in which an indole ring is condensed at positions 2 and 3 of the phenanthrene skeleton has a higher driving voltage and a longer life than the organic EL device using the compound (1). Is significantly shorter.
  • Reference Example A compound represented by the formula (2) or (3) was bonded to one or both of the 2-position and 3-position, and the 6-position and 7-position of the compounds (I) to (III) of the present invention and the phenanthrene ring.
  • the triplet energy gap E T1 difference between the first excited triplet energy and the ground state
  • the results are shown in Table 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un composé représenté par la formule (1) (dans la formule (1), les pointillés, A-D, et R 1 -R 10 sont tels que définis dans la description) et fournit un élément électroluminescent organique à haute performance.
PCT/JP2017/029157 2016-08-19 2017-08-10 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique Ceased WO2018034242A1 (fr)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
JP2020500892A (ja) * 2016-12-05 2020-01-16 メルク パテント ゲーエムベーハー Ｏｌｅｄに使用するための窒素含有ヘテロ環式化合物

Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291771A (en) * 1961-02-23 1966-12-13 Ciba Ltd Melt spinnable polyamide dyed with stable anthraquinones
KR20110041726A (ko) * 2009-10-16 2011-04-22 에스에프씨 주식회사 방향족 화합물 및 이를 이용한 유기전계발광소자
US20120097929A1 (en) * 2010-10-25 2012-04-26 Samsung Mobile Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
JP2012513459A (ja) * 2008-12-23 2012-06-14 ルミナノ カンパニー リミテッド 新規有機半導体化合物、その製造方法、及びこれを含む有機半導体組成物、有機半導体薄膜及び素子
KR20120072784A (ko) * 2010-12-24 2012-07-04 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
KR20120081539A (ko) * 2011-01-11 2012-07-19 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
JP2013045810A (ja) * 2011-08-22 2013-03-04 Udc Ireland Ltd 有機電界発光素子、化合物、並びに該素子を用いた発光装置、表示装置及び照明装置
JP2013058712A (ja) * 2011-08-18 2013-03-28 Udc Ireland Ltd 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置
WO2014137104A1 (fr) * 2013-03-07 2014-09-12 덕산하이메탈(주) Composé pour élément électronique organique, élément électronique organique comprenant le composé, et dispositif électronique utilisant l'élément électronique organique
CN104513247A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种苯并[c]苯并[3,4]咔唑并咔唑衍生物及应用
CN104513246A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种蒽并双咔唑衍生物及其应用
WO2016032150A2 (fr) * 2014-08-29 2016-03-03 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique utilisant ledit composé, et dispositif électronique comprenant ceux-ci
WO2016099037A2 (fr) * 2014-12-19 2016-06-23 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2016167505A1 (fr) * 2015-04-16 2016-10-20 에스에프씨 주식회사 Nouveau composé hétérocyclique et élément électroluminescent organique le comprenant
JP2017011224A (ja) * 2015-06-25 2017-01-12 山本化成株式会社 有機トランジスタ
WO2017052099A1 (fr) * 2015-09-22 2017-03-30 덕산네오룩스 주식회사 Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et dispositif électronique associé
WO2017052212A1 (fr) * 2015-09-24 2017-03-30 주식회사 엘지화학 Composé et dispositif optoélectronique organique le comprenant

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101905970B1 (ko) * 2015-09-24 2018-10-10 주식회사 엘지화학 화합물 및 이를 포함하는 유기전자소자

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291771A (en) * 1961-02-23 1966-12-13 Ciba Ltd Melt spinnable polyamide dyed with stable anthraquinones
JP2012513459A (ja) * 2008-12-23 2012-06-14 ルミナノ カンパニー リミテッド 新規有機半導体化合物、その製造方法、及びこれを含む有機半導体組成物、有機半導体薄膜及び素子
KR20110041726A (ko) * 2009-10-16 2011-04-22 에스에프씨 주식회사 방향족 화합물 및 이를 이용한 유기전계발광소자
US20120097929A1 (en) * 2010-10-25 2012-04-26 Samsung Mobile Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
KR20120072784A (ko) * 2010-12-24 2012-07-04 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
KR20120081539A (ko) * 2011-01-11 2012-07-19 (주)씨에스엘쏠라 유기발광화합물 및 이를 이용한 유기 광소자
JP2013058712A (ja) * 2011-08-18 2013-03-28 Udc Ireland Ltd 有機電界発光素子、該素子用材料、並びに該素子を用いた発光装置、表示装置及び照明装置
JP2013045810A (ja) * 2011-08-22 2013-03-04 Udc Ireland Ltd 有機電界発光素子、化合物、並びに該素子を用いた発光装置、表示装置及び照明装置
WO2014137104A1 (fr) * 2013-03-07 2014-09-12 덕산하이메탈(주) Composé pour élément électronique organique, élément électronique organique comprenant le composé, et dispositif électronique utilisant l'élément électronique organique
CN104513247A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种苯并[c]苯并[3,4]咔唑并咔唑衍生物及应用
CN104513246A (zh) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 一种蒽并双咔唑衍生物及其应用
WO2016032150A2 (fr) * 2014-08-29 2016-03-03 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique utilisant ledit composé, et dispositif électronique comprenant ceux-ci
WO2016099037A2 (fr) * 2014-12-19 2016-06-23 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2016167505A1 (fr) * 2015-04-16 2016-10-20 에스에프씨 주식회사 Nouveau composé hétérocyclique et élément électroluminescent organique le comprenant
JP2017011224A (ja) * 2015-06-25 2017-01-12 山本化成株式会社 有機トランジスタ
WO2017052099A1 (fr) * 2015-09-22 2017-03-30 덕산네오룩스 주식회사 Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et dispositif électronique associé
WO2017052212A1 (fr) * 2015-09-24 2017-03-30 주식회사 엘지화학 Composé et dispositif optoélectronique organique le comprenant

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
CHAMPAGNE, B. ET AL.: "Second-order nonlinear optical responses of heptahelicene and heptathiahelicene derivatives", CHEMICAL PHYSICS LETTERS, vol. 644, 14 December 2015 (2015-12-14), pages 195 - 200, XP029381812, DOI: doi:10.1016/j.cplett.2015.12.008 *
DATABASE REGISTRY 16 July 2010 (2010-07-16), "Naphtho[l,8-bc:4, 5-b'c']dicarbazole", Database accession no. 1232593-95-1 *
DATABASE REGISTRY 16 November 1984 (1984-11-16), "Benzo[a]benzo [1,2]naphtho[2',3' :7,8]carbazolo[4,3-c]naphtho [2,3-i]carbazole", Database accession no. 24369-21-9 *
DATABASE REGISTRY 17 August 2012 (2012-08-17), "Naphtho[l,2-a:4, 3-a']dicarbazole", Database accession no. 1391814-32-6 *
DATABASE REGISTRY 19 July 2016 (2016-07-19), "Indolo[2,3-a] phenanthro[l,2-c]carbazole", Database accession no. 1955517-09-5 *
DATABASE REGISTRY 21 May 2012 (2012-05-21), "Benzo[c]benzo[3,4] carbazolo[2,1-a]carbazole", Database accession no. 1374136-84-1 *
DATABASE REGISTRY 22 April 2014 (2014-04-22), "Indeno[2',1':5,6] naphtho[2,1-a]carbazole", Database accession no. 1588499-51-7 *
DATABASE REGISTRY 22 April 2014 (2014-04-22), "Indeno[2',1':5,6] naphtho[l,2-c]carbazole", Database accession no. 1588499-54-0 *
DATABASE REGISTRY 22 May 2002 (2002-05-22), "Naphtho[l,8-ab:4, 5-a'b']dicarbazole", Database accession no. 420108-97-0 *
DATABASE REGISTRY 24 April 2014 (2014-04-24), "Benzo[l,2-a:3, 4-c']dicarbazole", Database accession no. 1589514-90-8 *
DATABASE REGISTRY 25 May 2011 (2011-05-25), "Naphtho[l,8-ab: 5,4-b'c']dicarbazole", Database accession no. 1300575-62-5 *
DATABASE REGISTRY 25 May 2011 (2011-05-25), "Tetrabenzo[g,g',i, i']naphtho[l,8-bc:4,5-b'c']dicarbazole", Database accession no. 1300575-55-6 *
DATABASE REGISTRY 27 August 2012 (2012-08-27), "Benzo[l,2-a:4, 3-a']dicarbazole", Database accession no. 1392417-34-3 *
DATABASE REGISTRY 7 March 2013 (2013-03-07), "Indeno[2',1':5,6] phenaleno[l,9-bc]carbazole", Database accession no. 1422506-26-0 *
DATABASE REGISTRY 7 March 2013 (2013-03-07), "Indeno[l',2':5,6] phenaleno[l,9-bc]carbazole", Database accession no. 1422506-21-5 *
DATABASE REGISTRY 7 March 2013 (2013-03-07), "Pyreno[l,2-b:7, 8-b']bisbenzofuran", Database accession no. 1422506-23-7 *
NUMAN, H. ET AL.: "The resolution of heterohelicenes, a facile method using HPLC", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, vol. 95, no. 9, 1976, pages 211 - 212, XP055603746 *
YE, Q. ET AL.: "Cyclization of Tetraaryl- Substituted Benzoquinones and Hydroquinones through the Scholl Reaction", JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 19, 20 September 2016 (2016-09-20), pages 9219 - 9226, XP055605072, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01785 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020500892A (ja) * 2016-12-05 2020-01-16 メルク パテント ゲーエムベーハー Ｏｌｅｄに使用するための窒素含有ヘテロ環式化合物
JP7229919B2 (ja) 2016-12-05 2023-02-28 メルク パテント ゲーエムベーハー Ｏｌｅｄに使用するための窒素含有ヘテロ環式化合物
US12193325B2 (en) 2016-12-05 2025-01-07 Merck Patent Gmbh Nitrogen-containing heterocycles for use in OLEDs

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