WO2014050588A1 - Matériau d'élément électroluminescent organique et élément électroluminescent organique l'utilisant - Google Patents

Matériau d'élément électroluminescent organique et élément électroluminescent organique l'utilisant Download PDF

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WO2014050588A1
WO2014050588A1 PCT/JP2013/074657 JP2013074657W WO2014050588A1 WO 2014050588 A1 WO2014050588 A1 WO 2014050588A1 JP 2013074657 W JP2013074657 W JP 2013074657W WO 2014050588 A1 WO2014050588 A1 WO 2014050588A1
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淳也 小川
孝弘 甲斐
正樹 古森
山本　敏浩
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新日鉄住金化学株式会社
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Definitions

  • the present invention relates to an organic electroluminescent element containing an indolocarbazole compound, and more particularly to a thin film device that emits light by applying an electric field to a light emitting layer made of an organic compound.
  • an organic electroluminescent element (hereinafter referred to as an organic EL element) is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer as the simplest structure. That is, in an organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode, holes are injected from the anode, and these are recombined in the light emitting layer to emit light. .
  • CBP 4,4′-bis (9-carbazolyl) biphenyl
  • Ir (ppy) 3 2,4′-bis (9-carbazolyl) biphenyl
  • a host material having high triplet excitation energy and balanced in both charge (hole / electron) injection and transport characteristics is required. Further, a compound that is electrochemically stable and has high heat resistance and excellent amorphous stability is desired, and further improvement is required.
  • Patent Document 3 discloses indolocarbazole compounds as shown below.
  • the above compound is a compound in which a silyl group is directly bonded to the indolocarbazole skeleton, and a compound in which a silyl group is bonded to the nitrogen atom of the indolocarbazole skeleton through a nitrogen-containing aromatic heterocyclic group is not disclosed. Absent.
  • Patent Document 4 discloses an indolocarbazole compound as shown below.
  • a silyl group is bonded to the nitrogen atom of the indolocarbazole skeleton via two aromatic ring groups (or aromatic heterocyclic groups), and the nitrogen atom is contained on the nitrogen atom of the indolocarbazole skeleton. It does not disclose a compound in which a silyl group is bonded via one aromatic heterocyclic group.
  • Patent Document 5 discloses an indolocarbazole compound as shown below.
  • a silyl group is bonded to the nitrogen atom of the indolocarbazole skeleton via an aromatic hydrocarbon group, and the silyl group is bonded to the nitrogen atom of the indolocarbazole skeleton via a nitrogen-containing aromatic heterocyclic group. It does not disclose compounds in which is bound.
  • An object of this invention is to provide a practically useful organic electroluminescent element which has high efficiency and high brightness stability at the time of a drive, and a compound suitable for it in view of the said present condition.
  • an indolocarbazole compound in which a silyl group is linked by a nitrogen-containing aromatic heterocycle exhibits excellent characteristics by using it as an organic EL device, and completes the present invention. It came to.
  • the present invention relates to an organic electroluminescent element material comprising an indolocarbazole compound represented by the general formula (1).
  • ring A represents an aromatic ring represented by formula (1a) that is condensed at an arbitrary position of the adjacent ring
  • ring B is a formula (1b) that is condensed at an arbitrary position of the adjacent ring.
  • L 1 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 3 to 30 carbon atoms.
  • X 1 and X 2 represent methine or nitrogen
  • R 1 , R 2 and R 3 represent hydrogen, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 6 to 18 carbon atoms A group or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, wherein R 4 , R 5 and R 6 are an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a substituted or unsubstituted carbon group having 6 carbon atoms; Or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms.
  • p and q are integers of 1 to 4, r is 1 to 2, and s is an integer of 1 to 4. Hydrogen in the general formulas (1), (1a), and (1b) may be replaced with deuterium.
  • indolocarbazole compounds represented by the general formula (1) indolocarbazole compounds represented by any one of the following general formulas (2) to (6) are preferable compounds.
  • L 1 , L 2 , R 1 to R 6 , and p to s are the same as those in the general formula (1).
  • the present invention also relates to an organic electroluminescent device comprising an anode, an organic layer, and a cathode laminated on a substrate, the organic electroluminescent device having an organic layer containing the above-mentioned organic electroluminescent device material.
  • the organic layer containing the material for an organic electroluminescent element contains a phosphorescent dopant.
  • the indolocarbazole skeleton to which a nitrogen-containing aromatic heterocycle is bonded has high charge injection / transport capability, but it is necessary to optimize charge injection / transport properties to further improve device characteristics.
  • the light emitting element material when included in the light emitting layer of the phosphorescent light emitting element, the charge balance is improved, so that the recombination probability is improved.
  • this light-emitting device material has the lowest excited triplet state energy high enough to confine the dopant's lowest excited triplet state energy, thus reducing the triplet excitation energy transfer from the dopant to the host molecule. It can be effectively suppressed. From the above points, high luminous efficiency can be achieved.
  • this indolocarbazole compound is distributed on each substituent due to the effect of dividing the expansion of molecular orbitals by connecting the indolocarbazole skeleton and the silyl group via a nitrogen-containing aromatic heterocycle. Control the spread of molecular orbitals. Electrochemical stability (anti-oxidation and anti-reduction stability) is closely related to the molecular orbitals that contribute to them (highest occupied orbitals (HOMO) for oxidation, lowest orbitals (LUMO) for reduction). In order to improve the stability against both charges, it is essential to design a molecule so that HOMO is distributed at sites with high oxidation resistance and LUMO is distributed at sites with high reduction resistance.
  • This indolocarbazole compound is considered to be able to distribute molecular orbitals to sites with high oxidation / reduction stability by controlling the spread of molecular orbitals as described above, and to have good charge stability.
  • the phosphorescent light emitting element material exhibits good amorphous characteristics and high thermal stability, it is possible to realize a highly durable organic EL element with a low driving voltage.
  • the organic electroluminescent element material of the present invention is an indolocarbazole compound represented by the general formula (1).
  • an indolocarbazole compound represented by the general formula (1) By having one of the two nitrogens of the indolocarbazole compound substituted with a nitrogen-containing aromatic heterocycle to which a silicon group is bonded, it is considered that the excellent effects as described above are brought about.
  • the indolocarbazole compound for organic electroluminescent elements of this invention is used suitably as a material for phosphorescent light emitting elements, it is also called a material for phosphorescent light emitting elements.
  • ring A represents an aromatic ring represented by formula (1a) that is condensed at an arbitrary position of the adjacent ring
  • ring B is a formula (1b) that is condensed at an arbitrary position of the adjacent ring.
  • X 1 and X 2 independently represent methine or nitrogen. When both are methine, they are aromatic hydrocarbon rings, and when one or both are nitrogen, aromatic heteroelements It is a ring.
  • the aromatic ring may have a substituent represented by R 3 .
  • the heterocyclic ring has a substituent represented by -L 2- (SiR 4 R 5 R 6 ) s .
  • L 1 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms, the substituted or unsubstituted It represents a group constituted by connecting 2 to 6 aromatic hydrocarbons or substituted or unsubstituted aromatic heterocycles.
  • the substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, the substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, the substituted or unsubstituted aromatic hydrocarbon group, or the substituted or unsubstituted is a group constituted by connecting 2 to 5 substituted aromatic heterocycles.
  • unsubstituted aromatic hydrocarbon group examples include groups generated by removing one hydrogen from an aromatic hydrocarbon compound such as benzene, naphthalene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene.
  • an aromatic hydrocarbon compound such as benzene, naphthalene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene.
  • Preferable examples include groups generated by removing one hydrogen from benzene, naphthalene, anthracene, and phenanthrene.
  • unsubstituted aromatic heterocyclic group examples include pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthyridine, carbazole, dibenzofuran, dibenzothiophene, acridine, azepine, tribenzoazepine, phenazine, phenoxazine, phenothiazine, And a group formed by removing one hydrogen from an aromatic heterocyclic compound such as dibenzophosphole or dibenzoborol.
  • Preferable examples include groups formed by removing one hydrogen from pyridine, pyrimidine, triazine, carbazole, dibenzofuran, and dibenzothiophene.
  • the connected aromatic compounds may be the same or different. Also good.
  • the number to be linked is preferably 2 to 5, more preferably 2 or 3.
  • Specific examples of the group constituted by connecting 2 to 6 unsubstituted aromatic compounds include biphenyl, terphenyl, phenylnaphthalene, diphenylnaphthalene, phenylanthracene, diphenylfluorene, bipyridine, bipyrimidine, vitriazine, Biscarbazole, bisdibenzofuran, bisdibenzothiophene, phenylpyridine, phenylpyrimidine, phenyltriazine, phenylcarbazole, phenyldibenzofuran, phenyldibenzothiophene, diphenylpyridine, diphenyltriazine, biscarbazolylbenzene, bisdibenzofuranylbenzene, bisdibenzothio And a group formed by removing one hydrogen from phenylbenzene or the like.
  • aromatic hydrocarbon group, the aromatic heterocyclic group, and the group constituted by connecting two to six aromatic hydrocarbons or aromatic heterocyclic rings may have a substituent.
  • a preferable substituent is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acetyl group. More preferably, it is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or an acetyl group.
  • silicon-containing groups do not become substituents.
  • a group constituted by connecting 2 to 6 aromatic hydrocarbons or aromatic heterocycles is represented by the following formula, for example, linear or branched It may be connected.
  • Ar 1 to Ar 6 are unsubstituted aromatic hydrocarbons or aromatic heterocyclic rings.
  • L 2 represents a substituted or unsubstituted s + 1 valent nitrogen-containing aromatic heterocyclic group having 3 to 12 carbon atoms.
  • Preferred is a substituted or unsubstituted nitrogen-containing aromatic heterocyclic group having 3 to 10 carbon atoms.
  • the unsubstituted nitrogen-containing aromatic heterocyclic group examples include pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinolidine, phthalazine, quinazoline, quinoxaline, naphthyridine, carbazole, acridine, azepine, tribenzazepine, phenazine, phenoxazine, S + 1 groups generated by removing S + 1 hydrogen from a nitrogen-containing aromatic heterocyclic compound such as phenothiazine.
  • an S + 1 valent group derived from pyridine, pyrimidine, or triazine is used.
  • the nitrogen-containing aromatic heterocyclic compound preferably has a monocyclic structure or a structure in which 2 to 3 rings are condensed.
  • the nitrogen-containing aromatic heterocyclic ring may have a substituent, and when it has a substituent, preferred substituents include an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and a carbon number.
  • it is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, an acetyl group, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms.
  • silicon-containing groups do not become substituents.
  • substituents include methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group, octyl group, cyclopentyl group, cyclohexyl group, methoxy group, ethoxy group, propoxy group, butoxy group, Acetyl group, phenyl group, pyridyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, quinazolyl group, phthalazyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, and more Preferable examples include phenyl group, pyridyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, fluorenyl group, and carb
  • substituents may further have a substituent, preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, an acetyl group, an aromatic hydrocarbon group having 6 to 12 carbon atoms, carbon
  • a substituent preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, an acetyl group, an aromatic hydrocarbon group having 6 to 12 carbon atoms, carbon
  • aromatic heterocyclic group of formula 3 to 12 include methyl group, ethyl group, isopropyl group, butyl group, methoxy group, ethoxy group, acetyl group, phenyl group, pyridyl group, pyrimidyl group, triazyl group.
  • silicon-containing groups do not become this substituent.
  • p is an integer of 1 to 4, preferably an integer of 1 to 2.
  • q is an integer of 1 to 4, preferably an integer of 1 to 2.
  • r represents an integer of 1 to 2.
  • s is an integer of 1 to 4, preferably an integer of 1 to 2.
  • R 1 to R 3 are each independently hydrogen, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, An unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms is shown.
  • R 1 to R 3 are each independently hydrogen, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, An unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms.
  • an alkyl group having 1 to 4 carbon atoms a cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or a substituted or unsubstituted carbon group having 3 to 12 carbon atoms.
  • An aromatic heterocyclic group is an alkyl group having 1 to 4 carbon atoms, a
  • R 1 to R 3 include hydrogen, methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group, octyl group, cyclopentyl group, cyclohexyl group, methoxy group, ethoxy group, propoxy Group, butoxy group, acetyl group, phenyl group, pyridyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, quinazolyl group, phthalazyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group More preferred are hydrogen, phenyl group, pyridyl group, pyrimidyl group, triazyl group, naphthyl group, quinolyl group, isoquinolyl group, fluorenyl group, fluor
  • These may further have a substituent, preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, an acetyl group, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a carbon number of 3 -12 aromatic heterocyclic groups, and specific examples include methyl, ethyl, isopropyl, butyl, methoxy, ethoxy, acetyl, phenyl, pyridyl, pyrimidyl, triazyl, naphthyl Group, quinolyl group, isoquinolyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, or dibenzothiophenyl group.
  • silicon-containing groups do not become this substituent.
  • R 4 to R 6 are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted group. And an aromatic heterocyclic group having 3 to 17 carbon atoms. These aliphatic hydrocarbon group, aromatic hydrocarbon group or aromatic heterocyclic group are the same as described for R 1 to R 3 .
  • the indolocarbazole compounds represented by the general formula (1) may be mentioned as preferred compounds, and the above general formulas (2), (4 ), (5) or indolocarbazole compounds represented by (6) are more preferred compounds.
  • the total number of carbon atoms of the indolocarbazole compounds represented by the general formulas (1) to (6) is preferably 150 or less, more preferably 100 or less.
  • the indolocarbazole compounds represented by the general formulas (1) to (6) can be synthesized by selecting a raw material according to the structure of the target compound and using a known method.
  • skeleton (A-1) can be synthesized by the following reaction formula with reference to the synthesis example shown in p42-48.
  • the skeleton (A-2) can be synthesized by the following reaction formula with reference to the synthesis example shown in Journal of Heterocyclic Chemistry, 1992, 29, p1237.
  • the skeleton (A-3) can be synthesized by the following reaction formula.
  • the skeleton (A-4) can be synthesized by the following reaction formula with reference to synthesis examples shown in The Journal of Organic Chemistry, 2007, 72 (15) 5886 and Tetrahedron, 1999, 55, p2371.
  • the skeleton (A-5) can be synthesized by the following reaction formula with reference to the synthesis example shown in Archiv der Pharmazie (Weinheim, Germany), 1987, 320 (3), p280-2.
  • Indolocarbazole compounds represented by the general formulas (1) to (6) are obtained by substituting hydrogen on nitrogen of each indolocarbazole skeleton obtained by the above reaction formula with a corresponding aromatic group according to a conventional method. Groups can be synthesized.
  • indolocarbazole compounds represented by the general formulas (1) to (6) are shown below, but the organic electroluminescent element material of the present invention is not limited thereto.
  • the organic electroluminescent element material of the present invention contains an excellent organic electroluminescent element by containing it in at least one organic layer of an organic EL element in which an anode, a plurality of organic layers and a cathode are laminated on a substrate.
  • a light emitting layer As the organic layer to be contained, a light emitting layer, an electron transport layer or a hole blocking layer is suitable.
  • it when used in a light emitting layer, it can be used as a host material of a light emitting layer containing a fluorescent, delayed fluorescent or phosphorescent dopant, and the compound of the present invention emits fluorescence and delayed fluorescence. It can be used as an organic light emitting material.
  • the compound of the present invention is particularly preferably contained as a host material for a light emitting layer containing a phosphorescent dopant.
  • the organic EL device of the present invention has an organic layer having at least one light emitting layer between an anode and a cathode laminated on a substrate, and the at least one organic layer is for the organic electroluminescent device of the present invention.
  • the organic electroluminescent device material of the present invention is included in the light emitting layer together with a phosphorescent dopant.
  • the structure of the organic EL element of the present invention will be described with reference to the drawings.
  • the structure of the organic EL element of the present invention is not limited to the illustrated one.
  • FIG. 1 is a cross-sectional view showing a structural example of a general organic EL device used in the present invention, wherein 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, and 5 is a light emitting layer. , 6 represents an electron transport layer, and 7 represents a cathode.
  • the organic EL device of the present invention may have an exciton blocking layer adjacent to the light emitting layer, and may have an electron blocking layer between the light emitting layer and the hole injection layer.
  • the exciton blocking layer can be inserted on either the anode side or the cathode side of the light emitting layer, or both can be inserted simultaneously.
  • the organic EL device of the present invention has a substrate, an anode, a light emitting layer and a cathode as essential layers, but it is preferable to have a hole injecting and transporting layer and an electron injecting and transporting layer in layers other than the essential layers, and further emitting It is preferable to have a hole blocking layer between the layer and the electron injecting and transporting layer.
  • the hole injection / transport layer means either or both of a hole injection layer and a hole transport layer
  • the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.
  • the organic EL element of the present invention is preferably supported on a substrate.
  • the substrate is not particularly limited as long as it is conventionally used for an organic EL element.
  • a substrate made of glass, transparent plastic, quartz, or the like can be used.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • an electrode substance include conductive transparent materials such as metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when the pattern accuracy is not required (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. Or when using the substance which can be apply
  • the cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • an electron injecting metal a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy referred to as an electron injecting metal
  • an alloy referred to as an electron injecting metal
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the light emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a thickness of 1 to 20 nm on the cathode.
  • an element in which both the anode and the cathode are transmissive can be manufactured.
  • the light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from the anode and the cathode, respectively.
  • the light emitting layer includes an organic light emitting material and a host material.
  • a fluorescent light emitting material can be used alone for the light emitting layer, but it is preferable to use a fluorescent light emitting material as a fluorescent light emitting dopant and to mix a host material.
  • an indolocarbazole compound represented by the general formula (1) can be used as the fluorescent light emitting material in the light emitting layer.
  • it can be selected from them.
  • Polyphenylene, polyphenylene vinylene polymer compounds such as, organic silane derivatives, and the like.
  • Preferred examples include condensed aromatic compounds, styryl compounds, diketopyrrolopyrrole compounds, oxazine compounds, pyromethene metal complexes, transition metal complexes, and lanthanoid complexes, more preferably naphthacene, pyrene, chrysene, triphenylene, benzo [c] phenanthrene, Benzo [a] anthracene, pentacene, perylene, fluoranthene, acenaphthofluoranthene, dibenzo [a, j] anthracene, dibenzo [a, h] anthracene, benzo [a] naphthacene, hexacene, anthanthrene, naphtho [2,1 -f] isoquinoline, ⁇ -naphtha
  • an indolocarbazole compound represented by the general formula (1) can be used, but since it is known from a large number of patent documents, it can be selected from them.
  • a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene or a derivative thereof, N, N′-dinaphthyl-N, N′-diphenyl-4
  • Aromatic amine derivatives such as 4,4'-diphenyl-1,1'-diamine
  • metal chelated oxinoid compounds such as tris (8-quinolinato) aluminum (III)
  • bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenyl Butadiene derivatives, indene derivatives, coumarin derivatives,
  • the amount of the fluorescent light emitting dopant contained in the light emitting layer is 0.01 to 20% by weight, preferably 0.1 to 10% by weight. It should be in range.
  • an organic EL element injects electric charges into a luminescent material from both an anode and a cathode, generates an excited luminescent material, and emits light.
  • a charge injection type organic EL device it is said that 25% of the generated excitons are excited to a singlet excited state and the remaining 75% are excited to a triplet excited state.
  • certain fluorescent materials emit triplet-triplet annihilation or heat after energy transition to triplet excited state due to intersystem crossing etc. It is known that, due to the absorption of energy, the singlet excited state is crossed back to back and emits fluorescence, thereby expressing thermally activated delayed fluorescence.
  • the organic EL device of the present invention can also exhibit delayed fluorescence. In this case, both fluorescence emission and delayed fluorescence emission can be included. However, light emission from the host material may be partly or partly emitted.
  • a delayed light emitting material can be used alone in the light emitting layer, but it is preferable to use a delayed fluorescent material as a delayed fluorescent light emitting dopant and mix a host material.
  • an indolocarbazole compound represented by the general formula (1) can be used, but it can also be selected from known delayed fluorescent light emitting materials.
  • a tin complex, an indolocarbazole derivative, a copper complex, a carbazole derivative, and the like can be given. Specific examples include compounds described in the following non-patent documents and patent publications, but are not limited to these compounds.
  • delayed luminescent materials are shown, but are not limited to the following compounds.
  • the amount of the delayed fluorescent material contained in the light emitting layer is 0.01 to 50% by weight, preferably 0.1 to 20%. It is good to be in the range of wt%, more preferably 0.01 to 10%.
  • an indolocarbazole compound represented by the general formula (1) can be used, but it can also be selected from compounds other than indolocarbazole.
  • a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene or a derivative thereof, N, N′-dinaphthyl-N, N′-diphenyl-4
  • Aromatic amine derivatives such as 4,4'-diphenyl-1,1'-diamine
  • metal chelated oxinoid compounds such as tris (8-quinolinato) aluminum (III)
  • bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenyl Butadiene derivatives, indene derivatives, coumarin derivatives, ox
  • the light emitting layer When the light emitting layer is a phosphorescent light emitting layer, the light emitting layer contains a phosphorescent light emitting dopant and a host material.
  • the phosphorescent dopant material preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. Specific examples include compounds described in the following patent publications, but are not limited to these compounds.
  • Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 ⁇ acac3, and complexes such as PtOEt3. Specific examples of these complexes are shown below, but are not limited to the following compounds.
  • the amount of the phosphorescent dopant contained in the light emitting layer is 2 to 40% by weight, preferably 5 to 30% by weight.
  • the emissive layer is a phosphorescent light-emitting layer
  • an indolocarbazole compound represented by the general formula (1) as a host material in the light-emitting layer.
  • the material used for the light emitting layer may be a host material other than the indolocarbazole compound.
  • An indolocarbazole compound and another host material may be used in combination.
  • a plurality of known host materials may be used in combination.
  • a known host compound that can be used is preferably a compound that has a hole transporting ability and an electron transporting ability, prevents a long wavelength of light emission, and has a high glass transition temperature.
  • host materials are known from a large number of patent documents and can be selected from them.
  • Specific examples of the host material are not particularly limited, but include indole derivatives, carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine.
  • arylamine derivatives amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrin compounds, anthraquino Heterocyclic tetracarboxylic acid anhydrides such as dimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene,
  • the light emitting layer may be any one of a fluorescent light emitting layer, a delayed fluorescent light emitting layer and a phosphorescent light emitting layer, but is preferably a phosphorescent light emitting layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the indolocarbazole compound represented by the general formula (1) according to the present invention for the hole blocking layer.
  • the indolocarbazole compound represented by the general formula (1) according to the present invention for the hole blocking layer.
  • a hole blocking layer material may be used.
  • the material of the electron carrying layer mentioned later can be used as needed.
  • the electron blocking layer is made of a material that has a function of transporting holes and has a very small ability to transport electrons.
  • the electron blocking layer blocks the electrons while transporting holes, and the probability of recombination of electrons and holes. Can be improved.
  • the material for the electron blocking layer As the material for the electron blocking layer, the material for the hole transport layer described later can be used as necessary.
  • the thickness of the electron blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
  • the exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved.
  • the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
  • an indolocarbazole compound represented by the general formula (1) can be used as the material for the exciton blocking layer.
  • other materials for example, 1,3-dicarbazolylbenzene (mCP), Bis (2-methyl-8-quinolinolato) -4-phenylphenolato aluminum (III) (BAlq).
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • an indolocarbazole compound represented by the general formula (1) is preferably used, but any conventionally known compound can be selected and used.
  • Known hole transporting materials that can be used include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives.
  • Styrylanthracene derivatives Styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers, etc., but porphyrin compounds, aromatic tertiary amine compounds and It is preferable to use a styrylamine compound, and it is more preferable to use an aromatic tertiary amine compound.
  • the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
  • an electron transport material which may also serve as a hole blocking material
  • an indolocarbazole derivative represented by the general formula (1) according to the present invention it is preferable to use an indolocarbazole derivative represented by the general formula (1) according to the present invention, and any one of conventionally known compounds can be selected and used. Examples thereof include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, and oxadiazole derivatives.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • the aqueous layer was washed twice with 100 ml of ethyl acetate, and the organic layer obtained in the first fraction and the ethyl acetate layer from which the aqueous layer was washed were combined.
  • the organic layer was washed again with 100 ml of a saturated sodium bicarbonate solution and washed twice with 100 ml of water.
  • the obtained organic layer was dehydrated with magnesium sulfate, and magnesium sulfate was filtered off. Then, the solvent was distilled off under reduced pressure to obtain a viscous liquid. Thereafter, 2.5 g of palladium carbon and 150 ml of toluene were added and refluxed for 3 hours.
  • intermediate B 7.40 g (0.0289 mol), intermediate C 10.0 g (0.0241 mol), copper iodide 0.46 g (2.41 mol), tripotassium phosphate 20.5 g (0.0964 mol), trans-1,2 -Cyclohexanediamine 3.47 ml (0.0289 mol) and 1,4-dioxane 241 ml were added and stirred at 120 ° C overnight. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 4.0 g6.7 (6.77 mmol, yield 28.1%) of intermediate D as a white solid.
  • Example 1 Each thin film was laminated at a vacuum degree of 2.0 ⁇ 10 ⁇ 5 Pa by a vacuum deposition method on a glass substrate on which an anode made of an ITO substrate having a thickness of 110 nm was formed.
  • copper phthalocyanine (CuPC) was formed to a thickness of 25 nm on ITO as a hole injection layer.
  • NPB was formed to a thickness of 40 nm as a hole transport layer.
  • Compound 1 as a host material and Ir (ppy) 3 as a dopant were co-deposited from different vapor deposition sources on the hole transport layer to form a light emitting layer having a thickness of 40 nm. At this time, the concentration of Ir (ppy) 3 was 10 wt%.
  • Alq3 was formed to a thickness of 20 nm as an electron transport layer. Further, on the electron transport layer, lithium fluoride (LiF) was formed to a thickness of 1 nm as an electron injection layer. Finally, on the electron injection layer, aluminum (Al) was formed as an electrode to a thickness of 70 nm to produce an organic EL element.
  • LiF lithium fluoride
  • Al aluminum
  • the organic EL element had the light emission characteristics as shown in Table 3.
  • the luminance, voltage, and luminous efficiency show values at the time of driving at 20 mA / cm 2 .
  • the maximum wavelength of the device emission spectrum was 530 nm, and it was found that light emission from Ir (ppy) 3 was obtained.
  • Examples 2 to 10 An organic EL device in the same manner as in Example 1 except that Compound 3, 4, 5, 6, 13, 14, 16, 23, or 35 was used in place of Compound 1 as the host material of the light emitting layer in Example 1. It was created.
  • Comparative Example 1 An organic EL device was produced in the same manner as in Example 1 except that CBP was used as the host material of the light emitting layer in Example 1.
  • Comparative Example 2 An organic EL device was produced in the same manner as in Example 1 except that Compound H-1 was used as the host material for the light emitting layer in Example 1.
  • Comparative Example 3 An organic EL device was produced in the same manner as in Example 1 except that Compound H-2 was used as the host material for the light emitting layer in Example 1.
  • Comparative Example 4 An organic EL device was produced in the same manner as in Example 1 except that Compound H-3 was used as the host material for the light emitting layer in Example 1.
  • the organic EL device according to the present invention has practically satisfactory levels of light emission characteristics, driving voltage and durability, and is a flat panel display (mobile phone display device, vehicle-mounted display device, OA computer display device, television, etc.), surface light emission. Its technical value is great in applications to light sources (lighting, light sources for copying machines, backlight light sources for liquid crystal displays and instruments), display boards, and sign lamps that make use of the characteristics of the body.

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Abstract

L'invention concerne un élément électroluminescent organique qui améliore une efficacité lumineuse d'élément, assure de manière suffisante une stabilité d'attaque, et possède une constitution simple ; et un matériau d'élément électroluminescent organique qui est utilisé dans l'élément électroluminescent organique. Cet élément électroluminescent organique possède une couche électroluminescente entre une électrode positive et une électrode négative empilées sur un substrat, et la couche électroluminescente contient, en tant que matériau hôte, un matériau d'élément électroluminescent organique comprenant un composé d'indolocarbazole qui possède un dopant phosphorescent et un groupement silyle. Le matériau d'élément électroluminescent organique est un composé d'indolocarbazole ayant une structure dans laquelle le groupement silyle est remplacé par un atome d'azote d'un cycle indolocarbazole avec un composé hétérocyclique aromatique contenant de l'azote interposé entre ceux-ci.
PCT/JP2013/074657 2012-09-28 2013-09-12 Matériau d'élément électroluminescent organique et élément électroluminescent organique l'utilisant WO2014050588A1 (fr)

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