WO2015115529A1 - Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique - Google Patents

Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique Download PDF

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WO2015115529A1
WO2015115529A1 PCT/JP2015/052480 JP2015052480W WO2015115529A1 WO 2015115529 A1 WO2015115529 A1 WO 2015115529A1 JP 2015052480 W JP2015052480 W JP 2015052480W WO 2015115529 A1 WO2015115529 A1 WO 2015115529A1
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substituted
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carbon atoms
represented
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裕勝 伊藤
河村　昌宏
由美子 水木
匡 羽毛田
友治 羽山
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出光興産株式会社
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Definitions

  • the present invention relates to a compound, a material for an organic electroluminescence device comprising the compound, an organic electroluminescence device using the compound, and an electronic device equipped with the organic electroluminescence device.
  • an organic electroluminescence element (hereinafter also referred to as “organic EL element”) is composed of an anode, a cathode, and an organic thin film layer composed of one or more layers sandwiched between the anode and the cathode.
  • organic EL element When a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light emitting region, and the injected electrons and holes recombine in the light emitting region to generate an excited state, which is excited. Light is emitted when the state returns to the ground state.
  • organic EL elements can obtain various emission colors by using various light emitting materials for the light emitting layer, and therefore, researches for practical application to displays and the like are active. In particular, research on light emitting materials of the three primary colors of red, green, and blue is the most active, and intensive research has been conducted with the aim of improving characteristics. As characteristics of such an organic EL element, further improvement in light emission efficiency and reduction in driving voltage are
  • an object of the present invention is to provide an organic electroluminescence element that can be driven at a low voltage and can at least increase the efficiency of light emission or extend the life, and an electronic device equipped with the organic electroluminescence element. And providing a compound for realizing them.
  • [1] to [4] are provided.
  • [1] A compound represented by the following general formula (1).
  • X 1 to X 10 each represent C (R A1 ) to C (R A10 ) or a nitrogen atom. However, at least two selected from R A1 to R A10 are bonded to each other to form a saturated or unsaturated ring.
  • R A1 to R A10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the following general formula (2).
  • R A1 to R A10 (including a group bonded to a carbon atom constituting the ring at a position where each ring is bonded to each other) is represented by the following general formula (2) It is group represented by these.
  • Z shows an oxygen atom, a sulfur atom, or a selenium atom.
  • L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a bond of 2 to 4 of these groups Is a divalent group.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and Ar 1 And Ar 2 may be bonded to each other to form a ring.
  • a material for an organic electroluminescence device comprising the compound according to [1].
  • It has an organic thin film layer composed of one or more layers including at least a light emitting layer between an anode and a cathode facing each other, and at least one of the organic thin film layers contains the compound according to the above [1] An organic electroluminescence device.
  • an organic electroluminescence element that can be driven at a low voltage and can at least increase the efficiency of light emission or extend the lifetime, and an electronic device equipped with the organic electroluminescence element. Furthermore, the compound which can implement
  • 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.
  • “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • “atom number XX to YY” in the expression “ZZ group of substituted or unsubstituted atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In the case of substitution, the number of substituent atoms is not included.
  • “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom.
  • the carbon contained in the substituent is not included in the number of ring-forming carbons.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • the benzene ring has 6 ring carbon atoms
  • the naphthalene ring has 10 ring carbon atoms
  • the pyridinyl group has 5 ring carbon atoms
  • the furanyl group 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 number of ring-forming carbons.
  • the number of ring-forming atoms refers to a compound (for example, a monocyclic compound, a condensed ring compound, a bridged compound, or a carbocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a single 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. For example, the number of ring-forming atoms in the pyridine ring is 6, the number of ring-forming atoms in the quinazoline ring is 10, and the number of ring-forming atoms in the furan ring is 5.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is 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 spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
  • hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • the “heteroaryl group” and the “heteroarylene group” are groups containing at least one heteroatom as a ring-forming atom, and the heteroatom includes a nitrogen atom, an oxygen atom, and a sulfur atom. , Preferably at least one selected from silicon atoms and selenium atoms.
  • a “heteroaromatic ring” is a ring containing at least one heteroatom as a ring-forming atom, and the heteroatom includes a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, and a selenium atom. One or more selected are preferable.
  • the “substituted or unsubstituted carbazolyl group” means the following carbazolyl group, And a substituted carbazolyl group having an optional substituent with respect to the above group.
  • the substituted carbazolyl group may be condensed by bonding arbitrary substituents to each other, and may contain a heteroatom such as a nitrogen atom, an oxygen atom, a silicon atom and a selenium atom, and the bonding position is It may be any of 1st to 9th positions. Specific examples of such a substituted carbazolyl group include the groups shown below.
  • substituted or unsubstituted dibenzofuranyl group and “substituted or unsubstituted dibenzothiophenyl group” include the following dibenzofuranyl group and dibenzothiophenyl group, And a substituted dibenzofuranyl group and a substituted dibenzothiophenyl group further having an optional substituent with respect to the above group.
  • the substituted dibenzofuranyl group and the substituted dibenzothiophenyl group may be bonded together by arbitrary substituents and may be condensed, and include a hetero atom such as a nitrogen atom, an oxygen atom, a silicon atom, and a selenium atom.
  • the bonding position may be any of the 1st to 8th positions. Specific examples of such a substituted dibenzofuranyl group and a substituted dibenzothiophenyl group include the following groups.
  • X represents an oxygen atom or a sulfur atom
  • Y represents an oxygen atom, a sulfur atom, NH, NR a (R a is an alkyl group or an aryl group), CH 2 , or CR b 2 ( R b represents an alkyl group or an aryl group. ]
  • An optional substituent that can be “substituted” in the description of “substituted or unsubstituted” includes 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 3 to 50 (preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6); 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18).
  • An aryl group of 7 to 51 (preferably 7 to 30, more preferably 7 to 20) having an aryl group having 6 to 50 ring forming carbon atoms (preferably 6 to 25, more preferably 6 to 18).
  • Aryl group A mono- or di-substituted amino group having a selected substituent; an alkoxy group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18 and more preferably 1 to 8); 6 to 50 ring carbon atoms (preferably Is an aryloxy group having an aryl group of 6 to 25, more preferably 6 to 18); an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and a ring forming carbon number of 6 to A mono-, di- or tri-substituted silyl group having a substituent selected from 50 (preferably 6 to 25, more preferably 6 to 18) aryl groups; 5 to 50 ring atoms (preferably 5 to 24, More preferably 5 to 13) hetero
  • At least one selected from the group consisting of a carbonyl group; a carboxyl group; a vinyl group; a (meth) acryloyl group; an epoxy group; and an oxetanyl group is preferable.
  • substituents may be further substituted with the above-mentioned arbitrary substituents.
  • substituents may be bonded to each other to form a ring.
  • unsubstituted in the description of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted by these substituents.
  • a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms preferably 1 to 18, more preferably 1 to 8
  • substituted or unsubstituted ring carbon atoms having 3 to 50 carbon atoms preferably 1 to 18, more preferably 1 to 8.
  • cycloalkyl group substituted or unsubstituted 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 6) 18) an aryl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8), and a substituted or unsubstituted ring carbon atom number 6 to 50 (preferably 6).
  • X 1 to X 10 each represent C (R A1 ) to C (R A10 ) or a nitrogen atom, and at least two of X 1 to X 10 are C (R A1 ) to C (R A10 ) However, at least two selected from R A1 to R A10 are bonded to each other to form a saturated or unsaturated ring.
  • R A1 to R A10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the following general formula (2).
  • R A1 to R A10 (including a group bonded to a carbon atom constituting the ring at a position where each ring is bonded to each other) is represented by the following general formula (2) It is group represented by these.
  • Z shows an oxygen atom, a sulfur atom, or a selenium atom.
  • L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a bond of 2 to 4 of these groups Is a divalent group.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and Ar 1 And Ar 2 may be bonded to each other to form a ring. )]
  • X 1 to X 10 each represent C (R A1 ) to C (R A10 ) or a nitrogen atom. That is, X 1 is C (R A1 ) or a nitrogen atom, X 2 is C (R A2 ) or a nitrogen atom, X 3 is C (R A3 ) or a nitrogen atom, X 4 is C (R A4 ) or a nitrogen atom, X 5 is C (R A5 ) or a nitrogen atom, X 6 is C (R A6 ) or a nitrogen atom, X 7 is C (R A7 ) or a nitrogen atom, X 8 is C (R A8 ) or a nitrogen atom, X 9 Is C (R A9 ) or a nitrogen atom, and X 10 is C (R A10 ) or a nitrogen atom.
  • At least two selected from R A1 to R A10 are bonded to each other to form a saturated or unsaturated ring. That is, in the general formula (1), at least two of X 1 to X 10 are any one of C (R A1 ) to C (R A10 ), and at least 2 selected from R A1 to R A10 Are joined together to form a saturated or unsaturated ring. Therefore, the number of nitrogen atoms in X 1 to X 10 is 0 to 8. The number of nitrogen atoms in X 1 to X 10 is preferably 0 to 3, more preferably 0 to 2.
  • X 1 and X 2, X 2 and X 3, X 3 and X 4, X 4 and X 5, X 5 and X 6, X 6 and X 7, X 7 and X 8, X 8 and X 9 , X 9 and X 10 , and at least one selected from X 10 and X 1 are both groups selected from C (R A1 ) to C (R A10 ), and the selected R A1 to R A10 Together form a saturated or unsaturated ring.
  • [II] Two selected from X 1 to X 10 other than the group listed in [I] above are both groups selected from C (R A1 ) to C (R A10 ), and this selected R A1 Two of R A10 are bonded to each other to form a saturated or unsaturated ring.
  • Examples of the compound in which the ring of the above embodiment [I] is formed include, for example, X 1 and X 2 are C (R A1 ) and C (R A10 ) (wherein X 3 to X 10 are each C (R A3 ) to C (R A10 ) or a nitrogen atom), and two of R A1 and R A2 are bonded to each other to form a saturated or unsaturated ring.
  • Examples of the compound in which the ring of the above embodiment [II] is formed include, for example, X 1 and X 10 are C (R A1 ) and C (R A10 ) (wherein X 2 to X 9 are C (R A2 ) to C (R A9 ) or a nitrogen atom), and two of R A1 and R A10 are bonded to each other to form a saturated or unsaturated ring. Note that at least one such ring may be formed, and two or more such rings may be formed.
  • X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 are compounds in which the ring of the embodiment of [I] is formed. At least one selected from X 5 and X 6 , X 6 and X 7 , X 7 and X 8 , X 8 and X 9 , X 9 and X 10 , and X 10 and X 1 is both C (R A1 ) To C (R A10 ), and the selected two of R A1 to R A10 are preferably bonded to each other to form a saturated or unsaturated ring.
  • the saturated or unsaturated ring includes a substituted or unsubstituted aromatic ring having 6 to 40 (preferably 6 to 25, more preferably 6 to 18) ring-forming carbon atoms, a substituted or unsubstituted ring-forming atom number of 6 to 40 (preferably 6 to 25, more preferably 6 to 18) aromatic hetero ring, saturated with 6 to 40 (preferably 6 to 25, more preferably 6 to 18) ring-forming carbon atoms substituted or unsubstituted Or an unsaturated aliphatic ring and a saturated or unsaturated aliphatic hetero ring having 6 to 40 (preferably 6 to 25, more preferably 6 to 18) substituted or unsubstituted ring-forming atoms.
  • a ring is preferred. These rings may be rings in which the conjugated system is broken.
  • a compound in which at least one is a nitrogen atom is preferred.
  • the compound of X 1 ⁇ X 10 as the number of nitrogen atoms in the X 1 ⁇ X 10, and preferably 1 to 3, more preferably 1 or 2.
  • R A1 to R A10 are as described above, and more preferable examples of R A1 to R A10 include independently a hydrogen atom, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, An atom is preferred), a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), a substituted or unsubstituted ring carbon number 3 to 20 (preferably Are 3 to 10, more preferably 3 to 8, more preferably 5 or 6) cycloalkyl groups, substituted or unsubstituted 6 to 30 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18).
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, An atom is preferred
  • a cyano group a substituted or unsubstit
  • the “substituted or unsubstituted silyl group” that can be selected as R A1 to R A10 is preferably a “group represented by —Si (R C1 ) (R C2 ) (R C3 )”.
  • the “substituted or unsubstituted amino group” that can be selected as R A1 to R A10 is preferably a “group represented by —N (R D1 ) (R D2 )”.
  • R C1 to R C3 and R D1 to R D2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms (preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6), substituted or unsubstituted ring carbon atoms 6 to 50 An aryl group (preferably 3 to 25, more preferably 6 to 18), or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms (preferably 5 to 24, more preferably 5 to 13). is there.
  • R C1 to R C3 of the “group represented by —Si (R C1 ) (R C2 ) (R C3 )” are all hydrogen atoms
  • the group is “unsubstituted silyl group (—SiH 3 ) ”.
  • the group in the case where R D1 to R D2 of the group represented by —N (R D1 ) (R D2 ) are all hydrogen atoms is “unsubstituted amino group (—NH 2 )”.
  • R A1 to R A10 Specific examples of each group that can be selected as R A1 to R A10 , R C1 to R C3, and R D1 to R D2 are shown below.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (including isomers), and hexyl.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like.
  • aryl group examples include phenyl group, naphthyl group (1-naphthyl group, 2-naphthyl group), anthryl group (1-anthryl group, 2-anthryl group, etc.), biphenyl group, terphenyl group, benzo [a Anthryl group, phenanthryl group (1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, etc.), benzo [c] phenanthryl group, fluorenyl group, benzo [a] fluorenyl group, benzo [b] Fluorenyl group, benzo [c] fluorenyl group, dibenzofluorenyl group, picenyl group, tetracenyl group, pentacenyl group, pyrenyl group, chrysenyl group, benzo [g] chrycenyl group, s-indacenyl group, as-ind
  • heteroaryl group examples include pyrrolyl group, pyridyl group (2-pyridyl group and the like), imidazopyridyl group, bipyridyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, phenanthryl group and carbazolyl group [ 9-substituted-3-carbazolyl group and the like.
  • the substituent at the 9-position is an alkyl group having 1 to 10 carbon atoms (preferably 1 to 6), an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 14 carbon atoms), or 5 to 30 ring atoms.
  • heteroaryl group (Preferably 5 to 14) heteroaryl group.
  • a monovalent nitrogen-containing heteroaryl group such as: furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group (2-dibenzofuranyl group etc.), oxazolyl group, oxadiazolyl group, benzoxazolyl group, Monovalent oxygen-containing heteroaryl groups such as benzonaphthofuranyl group and dinaphthofuranyl group; benzothiophenyl group, dibenzothiophenyl group (2-dibenzothiophenyl group etc.), thiophenyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group, And monovalent sulfur-containing heteroaryl groups such as a benzonaphthothiophenyl group and a dinaphthothiophenyl group.
  • alkoxy group examples include groups in which the alkyl group portion is the alkyl group, and specific examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, and an octyl group.
  • An oxy group, a nonyloxy group, a decyloxy group, etc. are mentioned.
  • aryloxy group the group whose aryl group site
  • alkylthio group examples include groups in which the alkyl group moiety is the alkyl group, and specific examples include a methylthio group and an ethylthio group.
  • arylthio group the group whose aryl group site
  • the compound of the present invention includes R A1 to R A10 (including a group bonded to a carbon atom constituting the ring at a position where they are bonded to each other to form a ring). At least one of is a group represented by the general formula (2).
  • R A1 to R A10 including a group bonded to a carbon atom constituting the ring at a position where they are bonded to each other to form a ring.
  • At least one of is a group represented by the general formula (2).
  • two compounds selected from R A1 to R A10 in the general formula (1) are bonded to each other to form a saturated or unsaturated ring, as described above.
  • the group bonded to the formed ring may be a group represented by the general formula (2).
  • X 1 and X 2 are each a C (R A1) and C (R A2), Taking the case where the R A1 and R A2 are bonded to form a ring as an example, R A1 and R The group represented by the general formula (2) is bonded to the carbon atom constituting the ring formed by bonding with A2 , or any one of R A3 to R A10 is the above general formula ( It becomes group represented by 2).
  • the compound which has only one group represented by the said General formula (2) is preferable.
  • Z represents an oxygen atom, a sulfur atom, or a selenium atom, preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • L 1 in the general formula (2) represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or these Is a divalent group in which 2 to 4 groups are bonded.
  • single bond may be generally referred to as “direct bond” in other words.
  • the arylene group that can be selected as L 1 has 6 to 30 ring-forming carbon atoms, preferably 6 to 20, more preferably 6 to 14, and still more preferably 6 to 12.
  • Examples of the arylene group that can be selected as L 1 include a phenylene group (1,4-phenylene group, etc.), a naphthylene group (1,4-naphthylene group, 1,5-naphthylene group, etc.), and an anthrylene group (9,9).
  • 10-anthrylene group, etc.) biphenylylene group, terphenylylene group, benzoanthrylene group, phenanthrylene group, benzophenanthrylene group, fluorenylene group (2,7-fluorenylene group, etc.), benzofluorenylene group, dibenzofluorenylene group , Picenylene group, tetrasenylene group, pentasenylene group, pyrenylene group, chrysenylene group, benzocrisenylene group, s-indacenylene group, as-indacenylene group, fluoranthenylene group, benzofluoranthenylene group, peryleneylene group, coronenylene group and dibenzo Anthracenylene group, etc.
  • the above arylene group may be an arylene group having a substituent, for example, a 9,9-disubstituted fluorenylene group (9,9-dimethyl-2,7-fluorenylene group, 9,9-diphenyl). -2,7-fluorenylene group, or 9,9-di (trimethylsilyl) -2,7-fluorenylene group is preferable).
  • the number of ring-forming atoms of the heteroarylene group that can be selected as L 1 is 5 to 30, preferably 5 to 20, more preferably 5 to 14, and still more preferably 5 to 12.
  • Examples of the heteroarylene group that can be selected as L 1 include pyrrolylene group, pyridylene group (2,5-pyridylene group, etc.), imidazopyridylene group, pyrazolylene group, triazolylene group, tetrazolylene group, indoleylene group, isoindoleylene group, and the like.
  • Groups and divalent nitrogen-containing heteroarylene groups such as carbazolylene groups; furanylene groups, benzofuranylene groups, isobenzofuranylene groups, dibenzofuranylene groups (2,8-dibenzofuranylene groups, etc.), oxazolylene groups, oxadiazolylene groups Divalent oxygen-containing heteroarylene groups such as benzoxazolylene group, benzonaphthofurylene group and dinaphthofurylene group; thiophenylene group, benzothiophenylene group, dibenzothiophenylene group (2,8-dibenzothiophenylene group) Group), thiazolylene group, thia And divalent sulfur-containing heteroarylene groups such as a diazorylene group, a benzothiazolylene group, a benzonaphthothiophenylene group, and a dinaphthothiophenylene group.
  • the above-described heteroarylene group may be a heteroarylene group having a substituent, for example, a 9-substituted-3,6-carbazolylene group (the 9th-position substituent has 1 to 10 carbon atoms (preferably Is preferably an alkyl group having 1 to 6), an aryl group having 6 to 30 (preferably 6 to 14) ring carbon atoms, or a heteroaryl group having 5 to 30 (preferably 5 to 14) ring atoms. You can also choose.
  • a 9-substituted-3,6-carbazolylene group the 9th-position substituent has 1 to 10 carbon atoms (preferably Is preferably an alkyl group having 1 to 6), an aryl group having 6 to 30 (preferably 6 to 14) ring carbon atoms, or a heteroaryl group having 5 to 30 (preferably 5 to 14) ring atoms. You can also choose.
  • L 1 may be a divalent group formed by bonding 2 to 4 of these groups (arylene group and / or heteroarylene group).
  • the divalent group is preferably a divalent group formed by bonding 2 to 4 groups selected from the group consisting of the following groups.
  • any carbon atom that may have a substituent may have a substituent.
  • L 1 is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms. More preferably, it is an unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, and a substituted or unsubstituted phenylene group is Even more preferred.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a heteroaryl group having 5 to 30 ring atoms. Ar 1 and Ar 2 may be bonded to each other to form a ring.
  • the number of ring-forming carbon atoms of the aryl group that can be selected as Ar 1 and Ar 2 is 6 to 30, preferably 6 to 20, more preferably 6 to 14, and still more preferably 6 to 12.
  • Examples of the aryl group that can be selected as Ar 1 and Ar 2 include phenyl group, naphthyl group (1-naphthyl group, 2-naphthyl group), anthryl group (1-anthryl group, 2-anthryl group, etc.), biphenyl, and the like.
  • the aryl group described above may further be an aryl group having a substituent, such as a 9,9-disubstituted fluorenyl group (9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2).
  • a 9,9-disubstituted fluorenyl group (9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2).
  • -Fluorenyl group, 9,9-di (trimethylsilyl) -2-fluorenyl group and the like can also be selected.
  • the number of ring-forming atoms of the heteroaryl group that can be selected as Ar 1 and Ar 2 is 5 to 30, preferably 5 to 20, more preferably 5 to 14, and still more preferably 5 to 12.
  • the heteroaryl group that can be selected as Ar 1 and Ar 2 include, for example, pyrrolyl group, pyridyl group (2-pyridyl group and the like), imidazopyridyl group, bipyridyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, Monovalent nitrogen-containing heteroaryl groups such as isoindolyl group, phenanthroyl group and carbazolyl group; furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group (2-dibenzofuranyl group etc.), oxazolyl group, oxadiazolyl group Monovalent oxygen-containing heteroaryl groups such as benzoxazolyl group,
  • the heteroaryl group described above may be a heteroaryl group having a substituent.
  • a 9-substituted-3-carbazolyl group (the substituent at the 9-position has 1 to 10 carbon atoms (preferably 1).
  • an alkyl group an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 14) or a heteroaryl group having 5 to 30 ring atoms (preferably 5 to 14) is also selected.
  • Ar 1 and Ar 2 may be bonded to each other to form a ring.
  • examples of the group represented by the general formula (2) include the following groups.
  • At least one of Ar 1 and Ar 2 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and both Ar 1 and Ar 2 are More preferably, it is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and both Ar 1 and Ar 2 are substituted or unsubstituted aryl groups having 6 to 14 ring carbon atoms.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted fluorenyl group. It is even more preferable.
  • X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 , X 5 and X 6 , X 6 and At least one set selected from X 7 , X 7 and X 8 , X 8 and X 9 , X 9 and X 10 , and X 10 and X 1 are both selected from C (R A1 ) to C (R A10 )
  • a compound in which two selected from R A1 to R A10 are bonded to each other to form any of the rings represented by the following general formulas (3-a) to (3-e) hereinafter, Also referred to as “the compound of the first aspect of the present invention”).
  • the compound that forms any one of the rings represented by) is included in the compound of the first aspect of the present invention.
  • the compound of the first aspect of the present invention may be a compound having only one of the rings represented by the general formulas (3-a) to (3-e), It may be a compound having two or more of any of the rings represented by 3-a) to (3-e).
  • * represents a bond part with a carbon atom
  • Y represents —C (R B29 ) (R B30 ) —, —N (R B31 ) —, —Si (R B32 ) (R B33 ) —, —O—, or —S— is shown.
  • R B1 to R B33 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group Heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the general formula (2).
  • R B1 to R B33 are as described above, and more preferable R B1 to R B33 are each independently a hydrogen atom, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, An atom is preferred), a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), a substituted or unsubstituted ring carbon number 3 to 20 (preferably Are 1 to 10, more preferably 3 to 8, more preferably 5 or 6) cycloalkyl group, substituted or unsubstituted 6 to 30 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18).
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, An atom is preferred
  • a cyano group a substituted or unsubstitute
  • R B33 is - preferably "Si (R C1) (R C2 ) groups represented by (R C3)", R B1 ⁇
  • the “substituted or unsubstituted amino group” that can be selected as R B33 is preferably a “group represented by —N (R D1 ) (R D2 )” (R C1 to R C3 and R D1 to R D2 are , As described above).
  • R B1 to R B33 examples of more specific groups of the above-mentioned groups (alkyl group, cycloalkyl group, etc.) that can be selected as R B1 to R B33 are selected as R A1 to R A10 in the above general formula (1).
  • R A1 to R A10 examples of more specific groups of the above-mentioned groups (alkyl group, cycloalkyl group, etc.) that can be selected as R B1 to R B33 are selected as R A1 to R A10 in the above general formula (1).
  • R A1 to R A10 examples of each group to be obtained include the same groups as those exemplified.
  • At least one of R A1 to R A10 in the general formula (1) and R B1 to R B28 in the general formulas (3-a) to (3-e) Is a group represented by the general formula (2).
  • compounds represented by any one of the following general formulas (1-1) to (1-9) (hereinafter also referred to as “compound of the second aspect of the present invention”). ) Is more preferable.
  • X 1 to X 10 each represent C (R A1 ) to C (R A10 ) or a nitrogen atom.
  • R A1 to R A10 are the same as described above with respect to the general formula (1).
  • Y represents —C (R B29 ) (R B30 ) —, —N (R B31 ) —, —Si (R B32 ) (R B33 ) —, —O—, or —S—.
  • R B1 to R B33 and R B1 ′ to R B4 ′ are each independently a hydrogen atom, halogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (2).
  • R B1 to R B33 and R B1 ′ to R B4 ′ are as described above, and more preferable R B1 to R B33 and R B1 ′ to R B4 ′ are each independently a hydrogen atom, a halogen atom, A cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or An unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or
  • the “substituted or unsubstituted silyl group” that can be selected as R B1 to R B33 and R B1 ′ to R B4 ′ is represented by “—Si (R C1 ) (R C2 ) (R C3 )”.
  • a “substituted or unsubstituted amino group” that can be selected as R B1 to R B33 and R B1 ′ to R B4 ′ is represented by “—N (R D1 ) (R D2 )”. (R C1 to R C3 and R D1 to R D2 are as defined above).
  • Examples of more specific groups of the above-described groups (alkyl group, cycloalkyl group, etc.) that can be selected as R B1 to R B33 and R B1 ′ to R B4 ′ include those in the above general formula (1). Examples thereof include the same groups as those exemplified as each group that can be selected as R A1 to R A10 .
  • R A1 to R A10 , R B1 to R B28 , and R B1 ′ to R B4 ′ in the above formulas (1-1) to (1-9) is It is group represented by the said General formula (2).
  • R A1 to R A10 , R B1 to R B28 , and R B1 ′ to R B4 ′ is represented by the general formula (2).
  • the compound represented by any one of the general formulas (1-1) to (1-9) is preferably a compound having only one group represented by the general formula (2).
  • the compound of the third aspect of the present invention is a compound in which none of X 1 to X 10 in the general formulas (1-1) to (1-9) has a nitrogen atom.
  • the compound according to the third aspect of the present invention is preferably a compound represented by any one of the following general formulas (1-1A) to (1-9A).
  • R A1 to R A10 are the same as those described above for the general formula (1), and R B1 to R B28 , R B1 ′ to R B4 'And Y are the same as described above with respect to the general formulas (1-1) to (1-9).
  • At least one of R A1 to R A10 , R B1 to R B28 , and R B1 ′ to R B4 ′ in the general formulas (1-1A) to (1-9A) is represented by the general formula (2).
  • only one of R A1 to R A10 , R B1 to R B28 , and R B1 ′ to R B4 ′ is represented by the general formula (2).
  • the compound represented by any one of the general formulas (1-1A) to (1-9A) is preferably a compound having only one group represented by the general formula (2).
  • R A1 and R A4 in each formula are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • the compound represented by the general formula (1-1A) is preferable. Further, among the compounds represented by the general formula (1-1A), compounds having only one group represented by the general formula (2) are more preferable, and the following general formulas (1-1A-i) to The compound represented by any of (1-1A-iii) is more preferable.
  • L 1 , Ar 1 , Ar 2 , and Z are the same as described above with respect to the general formula (2).
  • R B1 to R B4 are the same as those described above with respect to the general formula (1-1).
  • R a1 , R a4 to R a10 and R b1 to R b4 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Substituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A substituted silyl group or a substituted or unsubstituted amino group.
  • all of R a1 , R a4 to R a10 and R b1 to R all of R a1 , R a4 to R a10 and R
  • R a1 , R a4 to R a10 , and R b1 to R b4 are the above-described R A1 , R A4 to R A4 , except that the group represented by the general formula (2) is not selected.
  • Examples of more specific groups of the above groups that can be selected as R a1 , R a4 to R a10 , and R b1 to R b4 include R A1 to R A10 in the above general formula (1).
  • R a4 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclocarbon having 3 to 20 ring carbon atoms.
  • a hydrogen atom preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is more preferable.
  • R a1 and R a4 in each formula are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • the compound according to the fourth aspect of the present invention is a compound in which at least one of X 1 to X 10 in the formulas (1-1) to (1-9) is a nitrogen atom.
  • the number of nitrogen atoms in X 1 to X 10 is 1 or more, preferably 1 to 3, more preferably 1 or 2.
  • at least one of X 1 , X 3 and X 4 is preferably a nitrogen atom.
  • the compound according to the fourth aspect of the present invention is preferably a compound represented by any one of the following general formulas (1-1B) to (1-5B).
  • R A2 , R A3 , R A5 to R A10 are the same as those described above for the general formula (1), and R B1 to R B4 , R B1 ′ to R B4 ′ , R B17 to R B20 and Y are the same as described above with respect to the general formulas (1-1) to (1-9).
  • One of the groups represented by the general formula (2) is R A2 , R A3 , R A5 to R A10 , R B1 to R B4 , R B17 to R B20 , and R B1 ′ to R B4 ′. It is preferable that only one of these is a group represented by the general formula (2).
  • the compound represented by any one of the above formulas (1-1B) to (1-5B) is preferably a compound having only one group represented by the general formula (2).
  • R A2 and R A3 in the formula are a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted number of ring forming atoms. A 5-30 heteroaryl group is preferred.
  • the compound according to the fourth aspect of the present invention is preferably a compound represented by any one of the following general formulas (1-6B) to (1-9B).
  • R A1 to R A7 and R A10 are the same as those described above for the general formula (1), and R B1 to R B4 are the same as the general formula. The same as the description above regarding (1-1) to (1-9).
  • R A1 to R A7 , R A10 , and R B1 to R B4 is a group represented by the general formula (2). It is preferable that only one of R A1 to R A7 , R A10 , and R B1 to R B4 is a group represented by the general formula (2).
  • the compound represented by any one of the above formulas (1-6B) to (1-8B) is preferably a compound having only one group represented by the general formula (2).
  • the compound represented by the general formula (1-1B) is preferable.
  • compounds having only one group represented by the general formula (2) are more preferable, and the following general formula (1-1Bi) to The compound represented by any of (1-1B-iii) is more preferable.
  • R a5 to R a10 and R b1 to R b4 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl.
  • R a5 to R a10 and R b1 to R b4 in the above formulas (1-1Bi) to (1-1B-iii) is a group represented by the general formula (2). .
  • R a5 to R a10 and R b1 to R b4 are the above-described R A5 to R A10 and R B1 except that the group represented by the general formula (2) is not selected. Same as the definition of ⁇ R B4 .
  • Examples of more specific groups of the above-mentioned groups that can be selected as R a5 to R a10 and R b1 to R b4 are selected as R A1 to R A10 in the above general formula (1).
  • Examples of each group to be obtained include the same groups as those exemplified.
  • the compounds represented by any one of the general formulas (1-1B-i) to (1-1B-iii) from the viewpoint of a material for an organic EL device that can further improve the luminous efficiency of the organic EL device, the compound represented by the general formula (1-1B-i) or (1-1B-ii) is preferable, and from the viewpoint of obtaining a material for an organic EL device that can further improve the life of the organic EL device, A compound represented by (1-1B-i) or (1-1B-iii) is preferred, and a compound represented by the general formula (1-1B-iii) is more preferred.
  • Specific examples of one embodiment of the compound of the present invention include the following compounds, but are not particularly limited thereto.
  • cases where X in the general formula (2) is an oxygen atom are listed. Therefore, the oxygen atom which the group represented by Formula (2) in the structure of the following compounds has can be replaced with a sulfur atom or a selenium atom.
  • any carbon atom that may have a substituent may have a substituent.
  • the organic EL device material of the present invention is composed of the compound of the present invention described above.
  • the organic EL device material of the present invention may be composed of only one of the compounds of the present invention, or may be composed of two or more of the compounds of the present invention.
  • the organic EL device of the present invention has an organic thin film layer composed of a single layer or a plurality of layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers is a compound of the present invention (hereinafter referred to as “ By including the “organic EL element material of the present invention”), the light emission efficiency of the organic EL element is increased and low voltage driving is enabled.
  • a hole transport zone also referred to as a hole transport layer provided between the anode and the light emitting layer of the organic EL device.
  • the term “hole transport zone” refers to the case where there is a single layer or a plurality of layers, and the electron transport zone (also referred to as an electron transport layer) provided between the cathode and the light emitting layer of the organic EL element.
  • the term “electron transport zone” is used in the meaning of including one or a plurality of electron transport layers, and a light emitting layer, a space layer, a barrier layer, and the like.
  • the organic EL device material of the present invention is preferably included in the electron transport zone.
  • the organic EL device of the present invention may be a fluorescent or phosphorescent monochromatic light emitting device, a fluorescent / phosphorescent hybrid white light emitting device, or a simple type having a single light emitting unit. It may be a tandem type having a plurality of light emitting units. Among these, a phosphorescent light emitting type is preferable.
  • the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit 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 light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, excitation generated in the phosphorescent light emitting layer between the light emitting layers.
  • a space layer may be provided.
  • a typical layer structure of the light emitting unit is shown below.
  • A Hole transport layer / light emitting layer (/ electron transport layer)
  • B Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
  • C Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
  • D Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • E Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • F Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
  • G Hole transport layer / electron barrier layer / light emitting layer (/ electron transport layer)
  • H Hole transport layer / light emitting layer / hole barrier layer (
  • Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
  • hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / Examples include a layer configuration such as an 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 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 of the present invention.
  • 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 includes a light emitting layer 5 including at least one phosphorescent light emitting layer including a phosphorescent host material and a phosphorescent dopant (phosphorescent material).
  • a hole transport zone (hole transport layer) 6 or the like may be formed between the light emitting layer 5 and the anode 3, and an electron transport zone (electron transport layer) 7 or the like may be formed between the light emitting layer 5 and the cathode 4.
  • an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5.
  • a host combined with a fluorescent dopant is referred to as a fluorescent host
  • a host combined with a phosphorescent dopant is referred to as 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 constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the substrate is used as a support for the light emitting element.
  • the substrate for example, 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 For 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
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide and indium oxide containing zinc oxide.
  • graphene graphene.
  • gold (Au), platinum (Pt), a nitride of a metal material (for example, titanium nitride), or the like can be given.
  • the hole transport zone includes a substance having a high hole injection property and / or a high hole transport property.
  • Substances with high hole injection properties include 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]
  • Polymer 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.
  • an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like, which is a substance having a high hole transport property can be used in the hole transport zone.
  • NPB 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • TPD Diphenyl- [1,1′-biphenyl] -4,4′-diamine
  • BAFLP 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine
  • 4 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl abbreviation: DFLDPBi
  • 4,4 ′, 4 ′′ -tris N, N-dip
  • the substances described here are mainly substances having a hole mobility of 10 ⁇ 6 cm 2 / Vs or higher.
  • carbazole derivatives such as CBP, CzPA, and PCzPA
  • anthracene derivatives such as t-BuDNA, DNA, and DPAnth
  • a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK N-vinylcarbazole
  • PVTPA poly (4-vinyltriphenylamine
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.
  • the light-emitting layer is a layer including a substance having high light-emitting properties, and various materials can be used.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the substance having high light-emitting property.
  • a fluorescent compound is a compound that can emit light from a singlet excited state
  • a phosphorescent compound is a compound that can emit 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.
  • N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA)
  • N- (9,10-diphenyl-2-anthryl) -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1′-biphenyl-2-yl)]-
  • 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.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used.
  • a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used.
  • iridium complex 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 (Fdp
  • phosphorescent materials ortho-metalated complexes of iridium (Ir), osmium (Os), or platinum (Pt) metal are preferable.
  • the light-emitting layer may have a structure in which the above-described highly light-emitting substance (guest material) is dispersed in another substance (host material).
  • Various materials can be used as a material for dispersing a highly luminescent substance.
  • the lowest unoccupied orbital level (LUMO level) is higher than that of a highly luminescent substance, and the highest occupied orbital level ( It is preferable to use a substance having a low HOMO level.
  • LUMO level lowest unoccupied orbital level
  • the compound of the present invention is preferable.
  • metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes
  • heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives
  • carbazole derivatives Condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives
  • aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.
  • the electron transport zone includes a substance having a high electron injection property and / or a high electron transport property. As described above, the electron transport zone preferably contains the compound of the present invention. In the electron transport zone, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), which are highly electron-injecting substances, are used. ), An alkali metal such as lithium oxide (LiOx), an alkaline earth metal, or a compound thereof.
  • a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property specifically, a substance in which magnesium (Mg) is contained in Alq may be used.
  • Mg magnesium
  • electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donating dopant may be used in the electron transport zone.
  • Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donating dopant.
  • the organic compound is preferably a material that is excellent in transporting the generated electrons.
  • the electron donating dopant may be any substance that exhibits an electron donating property with respect to the organic compound.
  • Specific examples include alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, and rare earth metal compounds.
  • Examples of the alkali metal, alkaline earth metal, and rare earth metal include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • Alkali metal oxides and alkaline earth metal oxides are also preferable.
  • lithium oxide, calcium oxide, barium oxide, and the like can be used.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • the electron transport zone includes substances having high electron transport properties, such as 1) organometallic complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, Heteroaromatic compounds such as phenanthroline derivatives, and 3) polymer compounds can be used.
  • organometallic complex it is preferable to use at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, and an organometallic complex containing a rare earth metal.
  • organometallic complexes include 8-quinolinolatolithium (abbreviation: Liq), Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato. ) Beryllium (abbreviation: BeBq 2 ), BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used.
  • heteroaromatic compound examples include 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-methylbenzoxazol-2-
  • 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) and the like.
  • the substances described here are mainly substances having an electron mobility of 10 ⁇ 6 cm 2 / Vs or higher.
  • the electron transport zone is not limited to a single layer, and two or more layers made of the above substances may be stacked.
  • the electron transport zone preferably further contains at least one selected from the electron donating dopant and the organometallic complex in addition to the compound of the present invention.
  • 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 alkaline earth such as magnesium (Mg). And other rare earth metals such as alloys and alloys containing them (for example, MgAg, AlLi) and alloys containing these.
  • a layer containing an acceptor material that is, an acceptor layer may be provided between the anode and the hole transport zone, and it is preferable to be so. This is expected to reduce drive voltage and manufacturing costs.
  • an acceptor material a compound represented by the following formula (K) is preferable.
  • R 401 to R 406 are each independently a cyano group, —CONH 2 , a carboxyl group, or —COOR 407 (R 407 is an alkyl group having 1 to 20 carbon atoms.) Or R 401 and R 402 , R 403 and R 404 , or R 405 and R 406 are bonded to each other to represent a group represented by —CO—O—CO—.
  • Examples of the alkyl group for R 407 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.
  • n-doping is a method of doping a metal such as Li or Cs into an electron transport material
  • p-doping 2,3,5,6-tetrafluoro- Examples thereof include a method of doping an acceptor material such as 7,7,8,8-tetracyanoquinodimethane (F 4 TCNQ).
  • the space layer is a fluorescent layer for the purpose of adjusting the carrier balance so that excitons generated in the phosphorescent layer are not diffused into the fluorescent layer. It is a layer provided between the 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 barrier layer such as an electron barrier layer, a hole barrier layer, or a triplet barrier layer can be provided in a portion adjacent to the light emitting layer.
  • the electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
  • the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. is there.
  • the triplet barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the surrounding layers, and confins the triplet excitons in the light emitting layer, thereby transporting electrons other than the light emitting dopant of the triplet excitons.
  • E T d E T TB ⁇ E T d
  • the electron mobility of the material constituting the triplet barrier layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm.
  • the electron mobility is determined by impedance spectroscopy.
  • the electron injection layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm. This facilitates the injection of electrons from the cathode into the electron transport layer, and also promotes the injection of electrons into the adjacent barrier layer and the light emitting layer, thereby enabling driving at a lower voltage.
  • the organic EL device obtained by using the compound of the present invention has high luminous efficiency and can be driven at a low voltage. For this reason, it can be used for display devices such as organic EL panel modules; display devices such as televisions, mobile phones, and personal computers;
  • 3-bromo-7,12-diphenylbenzo [k] fluoranthene (3.00 g, 6.21 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to -78 ° C. Thereafter, n-BuLi (2.50 M hexane solution, 4.22 mL, 10.6 mmol) was added dropwise over 20 minutes, and the mixture was stirred at ⁇ 78 ° C. for 1 hour. Then, the temperature was raised to ⁇ 50 ° C., diphenylphosphine chloride (1.37 g, 6.21 mmol) was added, the temperature was raised to room temperature (25 ° C.), and the mixture was stirred for 8 hours.
  • the mixture was purified by silica gel column chromatography to obtain a compound (1.31 g, 2.17 mmol, yield 35%).
  • the following performance of the produced organic EL element was measured by the following method.
  • (1) Drive voltage The drive voltage (V) when energized between the anode (ITO transparent electrode) and the metal cathode (metal Al) of the produced organic EL element so that the current density is 10 mA / cm 2 Measured.
  • Example 1 A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HI-1 is first deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed.
  • An acceptor layer having a thickness of 5 nm was formed.
  • the compound HT-1 is vapor-deposited as a first hole transport material on the formed acceptor layer to form a first hole transport layer (hole transport zone) having a film thickness of 155 nm.
  • the compound HT-2 was vapor-deposited on the layer to form a second hole transport layer (hole transport zone) having a thickness of 10 nm.
  • the concentration of the compound PGD-1 in the light emitting layer was 5.0% by mass.
  • 8-quinolinolato lithium (Liq) was vapor-deposited to form an electron injection layer having a thickness of 1 nm.
  • Metal Al was vapor-deposited on this electron injection layer, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
  • Example 2 An organic EL device was produced in the same manner as in Example 1 except that the compound (2) obtained in Synthesis Example 2 was used in place of the compound (1).
  • Comparative Example 1 An organic EL device was produced in the same manner as in Example 1 except that the comparative example compound was used instead of the compound (1).
  • the organic EL element produced in Examples 1 and 2 is superior in terms of light emission efficiency and can be driven at a lower voltage than the organic EL element produced in Comparative Example 1. became. Since the compound of the present invention has a condensed fluoranthene structure, it is considered that the compound has higher electron affinity, and is considered to function advantageously for electron injection from the cathode. Therefore, in the organic EL device using the compound of the present invention, electrons are suitably supplied to the light emitting layer, so that it is considered that the carrier balance is optimized and the effect of improving the light emission efficiency is exhibited.
  • Example 3 A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HI-1 is first deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed.
  • An acceptor layer having a thickness of 5 nm was formed.
  • the compound HT-3 is deposited as a first hole transport material on the formed acceptor layer to form a first hole transport layer (hole transport zone) having a thickness of 80 nm, and the first hole transport layer is formed.
  • the compound HT-4 was vapor-deposited on the layer to form a second hole transport layer (hole transport zone) having a thickness of 10 nm.
  • the concentration of the compound BD-1 in the light emitting layer was 4.0% by mass.
  • 8-quinolinolato lithium (Liq) was vapor-deposited to form an electron injection layer having a thickness of 1 nm.
  • Metal Al was vapor-deposited on this electron injection layer, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
  • Example 4 An organic EL device was produced in the same manner as in Example 3 except that the compound (5) obtained in Synthesis Example 5 was used in place of the compound (4).
  • Comparative Example 2 An organic EL device was produced in the same manner as in Example 3 except that the comparative compound was used instead of the compound (4).

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Abstract

Selon l'invention, un élément électroluminescent organique, qui utilise un composé de structure spécifique ayant un squelette de fluoranthène, peut être excité à basse tension et offrir au moins un rendement d'éclairage élevé ou une plus longue durée de vie de service.
PCT/JP2015/052480 2014-01-31 2015-01-29 Composé, matériau pour des éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique WO2015115529A1 (fr)

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KR20170065974A (ko) * 2015-12-04 2017-06-14 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
US10435350B2 (en) 2014-09-19 2019-10-08 Idemitsu Kosan Co., Ltd. Organic electroluminecence device
KR20200051223A (ko) * 2018-11-05 2020-05-13 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
KR20210154763A (ko) * 2020-06-12 2021-12-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

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US10435350B2 (en) 2014-09-19 2019-10-08 Idemitsu Kosan Co., Ltd. Organic electroluminecence device
KR20170065974A (ko) * 2015-12-04 2017-06-14 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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KR20200051223A (ko) * 2018-11-05 2020-05-13 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
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KR20210154763A (ko) * 2020-06-12 2021-12-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102560366B1 (ko) 2020-06-12 2023-07-27 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

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