WO2013038843A1 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- WO2013038843A1 WO2013038843A1 PCT/JP2012/070007 JP2012070007W WO2013038843A1 WO 2013038843 A1 WO2013038843 A1 WO 2013038843A1 JP 2012070007 W JP2012070007 W JP 2012070007W WO 2013038843 A1 WO2013038843 A1 WO 2013038843A1
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- PNDQXXBAAIHACR-UHFFFAOYSA-N C(C1)C=Cc2c1[o]c1cccc(-[n]3c(ccc(-c4cc(-c5ccccc5)cc(-c5nc(-c(cc6)cc(c7c8cccc7)c6[n]8-c6cccc7c6c(cccc6)c6[o]7)ccc5)n4)c4)c4c4ccccc34)c21 Chemical compound C(C1)C=Cc2c1[o]c1cccc(-[n]3c(ccc(-c4cc(-c5ccccc5)cc(-c5nc(-c(cc6)cc(c7c8cccc7)c6[n]8-c6cccc7c6c(cccc6)c6[o]7)ccc5)n4)c4)c4c4ccccc34)c21 PNDQXXBAAIHACR-UHFFFAOYSA-N 0.000 description 1
- MPNKVMIUURKNOK-UHFFFAOYSA-N C(C1c2c3ccc(-c4nc(-c5cccc(-c(cc6)cc(c7c8cccc7)c6[n]8-c6cccc7c6c(cccc6)c6[o]7)n5)ccc4)c2)=CC=CC1N3c1c(c(cccc2)c2[o]2)c2ccc1 Chemical compound C(C1c2c3ccc(-c4nc(-c5cccc(-c(cc6)cc(c7c8cccc7)c6[n]8-c6cccc7c6c(cccc6)c6[o]7)n5)ccc4)c2)=CC=CC1N3c1c(c(cccc2)c2[o]2)c2ccc1 MPNKVMIUURKNOK-UHFFFAOYSA-N 0.000 description 1
- OZIAHCJQXDFSBP-UHFFFAOYSA-N c(cc1c2c3ccc(-c4cc(-c5cccc(-c6cc(-c(cc7)cc(c8ccccc88)c7[n]8-c7c(c8ccccc8[o]8)c8ccc7)ccc6)c5)ccc4)c2)ccc1[n]3-c1c(c2ccccc2[o]2)c2ccc1 Chemical compound c(cc1c2c3ccc(-c4cc(-c5cccc(-c6cc(-c(cc7)cc(c8ccccc88)c7[n]8-c7c(c8ccccc8[o]8)c8ccc7)ccc6)c5)ccc4)c2)ccc1[n]3-c1c(c2ccccc2[o]2)c2ccc1 OZIAHCJQXDFSBP-UHFFFAOYSA-N 0.000 description 1
- AUBAFXUFSVUBOD-UHFFFAOYSA-N c(cc1c2c3ccc(-c4ccccc4-c(cc4c5c6cccc5)ccc4[n]6-c4cccc5c4c4ccccc4[s]5)c2)ccc1[n]3-c1c(c2ccccc2[o]2)c2ccc1 Chemical compound c(cc1c2c3ccc(-c4ccccc4-c(cc4c5c6cccc5)ccc4[n]6-c4cccc5c4c4ccccc4[s]5)c2)ccc1[n]3-c1c(c2ccccc2[o]2)c2ccc1 AUBAFXUFSVUBOD-UHFFFAOYSA-N 0.000 description 1
- UIANGROGYRLJKU-UHFFFAOYSA-N c(cc1c2cc(-c3c(cccc4-c(cc5)cc(c6ccccc66)c5[n]6-c5c(c6ccccc6[o]6)c6ccc5)c4ccc3)ccc22)ccc1[n]2-c1cccc2c1c(cccc1)c1[o]2 Chemical compound c(cc1c2cc(-c3c(cccc4-c(cc5)cc(c6ccccc66)c5[n]6-c5c(c6ccccc6[o]6)c6ccc5)c4ccc3)ccc22)ccc1[n]2-c1cccc2c1c(cccc1)c1[o]2 UIANGROGYRLJKU-UHFFFAOYSA-N 0.000 description 1
- CSEICUREGALGFH-UHFFFAOYSA-N c(cc1c2cc(-c3cc(-c4cccc(-c(cc5)cc(c6ccccc66)c5[n]6-c5c(c6ccccc6[o]6)c6ccc5)c4)ccc3)ccc22)ccc1[n]2-c1cccc2c1c(cccc1)c1[o]2 Chemical compound c(cc1c2cc(-c3cc(-c4cccc(-c(cc5)cc(c6ccccc66)c5[n]6-c5c(c6ccccc6[o]6)c6ccc5)c4)ccc3)ccc22)ccc1[n]2-c1cccc2c1c(cccc1)c1[o]2 CSEICUREGALGFH-UHFFFAOYSA-N 0.000 description 1
- CHOGMNBMKIKITJ-UHFFFAOYSA-N c(cc1c2cc(-c3cc(-c4cccc(-c5cc(-c(cc6)cc(c7ccccc77)c6[n]7-c6c(c7ccccc7[o]7)c7ccc6)ccc5)n4)ccc3)ccc22)ccc1[n]2-c1c(c2ccccc2[o]2)c2ccc1 Chemical compound c(cc1c2cc(-c3cc(-c4cccc(-c5cc(-c(cc6)cc(c7ccccc77)c6[n]7-c6c(c7ccccc7[o]7)c7ccc6)ccc5)n4)ccc3)ccc22)ccc1[n]2-c1c(c2ccccc2[o]2)c2ccc1 CHOGMNBMKIKITJ-UHFFFAOYSA-N 0.000 description 1
- MPYRVNGRXWVCHQ-UHFFFAOYSA-N c(cc1c2cc(-c3cccnc3-c(cc3c4c5cccc4)ccc3[n]5-c3cccc4c3c(cccc3)c3[s]4)ccc22)ccc1[n]2-c1c(c2ccccc2[s]2)c2ccc1 Chemical compound c(cc1c2cc(-c3cccnc3-c(cc3c4c5cccc4)ccc3[n]5-c3cccc4c3c(cccc3)c3[s]4)ccc22)ccc1[n]2-c1c(c2ccccc2[s]2)c2ccc1 MPYRVNGRXWVCHQ-UHFFFAOYSA-N 0.000 description 1
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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Definitions
- the present invention relates to an organic electroluminescent device, 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 a carbazole compound as shown below as a host material of an organic EL element.
- this carbazole derivative has a phenyl group at positions 3 and 7 of dibenzofuran, it is presumed that sufficient luminous efficiency cannot be obtained.
- Patent Document 4 discloses a carbazole compound as shown below as a host material of an organic EL element.
- Patent Document 5 discloses a carbazole compound as shown below as a host material of an organic EL element.
- Patent Document 6 discloses a carbazole compound as shown below as a host material of an organic EL element.
- the above compound only discloses a compound having a phenyl group introduced at the 9-position of carbazole, and does not disclose the usefulness of an organic EL device using a compound having carbazole introduced at the 1-position of dibenzothiophene or dibenzofuran. Absent.
- An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.
- an organic EL compound having a skeleton bonded to the 1-position of dibenzothiophene or dibenzofuran at the N-position of carbazole and 2 to 4 linked at the 3-position of carbazole It has been found that it exhibits excellent characteristics when used as an element, and the present invention has been completed.
- the present invention relates to an organic electroluminescence device in which an anode, an organic layer, and a cathode are laminated on a substrate, and includes a light emitting layer, a hole transport layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
- the present invention relates to an organic electroluminescent device using a carbazole compound represented by the general formula (1) in at least one selected layer.
- A is a direct bond, -O-, -S-, -Se-,>N-,>NR,> Si- (R) 2 ,> Ge- (R) 2 , and an n-valent fat having 1 to 12 carbon atoms.
- Hydrocarbon group n-valent alicyclic hydrocarbon group having 3 to 12 carbon atoms, n-valent aromatic hydrocarbon group having 6 to 18 carbon atoms, n-valent aromatic heterocyclic group having 3 to 17 carbon atoms Or an n-valent group in which 2 to 4 aromatic rings selected from an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 3 to 17 carbon atoms are connected,
- the aromatic hydrocarbon group, n-valent aromatic heterocyclic group, or the above aromatic ring may have a substituent.
- R independently represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 3 to 17 carbon atoms.
- R ′ each independently represents hydrogen, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.
- E represents oxygen or sulfur.
- n represents an integer of 2 to 4.
- A is a direct bond, an n-valent aliphatic hydrocarbon group having 1 to 6 carbon atoms, an n-valent alicyclic hydrocarbon group having 3 to 8 carbon atoms, and the n-valent aromatic carbonized carbon. It is preferably any one of a hydrogen group, the n-valent aromatic heterocyclic group, or an n-valent group in which 2 to 4 aromatic rings are connected. Further, it is more preferably any of a direct bond, an n-valent aromatic hydrocarbon group, an n-valent aromatic heterocyclic group, or an n-valent group in which 2 to 4 aromatic rings are connected. In general formula (1), n is preferably an integer of 2 or 3.
- the organic electroluminescent element preferably has a light emitting layer containing a carbazole compound represented by the general formula (1) and a phosphorescent light emitting dopant.
- FIG. 1 shows a 1 H-NMR chart of a carbazole compound (1).
- 1 shows a 1 H-NMR chart of a carbazole compound (40).
- the organic electroluminescent element of the present invention contains the carbazole compound represented by the general formula (1) in a specific layer.
- A is a direct bond or an n-valent group, but n is 2, 3 or 4.
- A is a direct bond, -O-, -S-, -Se-,>N-,>NR,> Si- (R) 2 ,> Ge- (R) 2 , carbon number 1 to 12, preferably 1.
- Two to four aromatic rings selected from an n-valent aromatic heterocyclic group having 3 to 17 carbon atoms, an aromatic hydrocarbon ring having 6 to 18 carbon atoms, and an aromatic heterocyclic ring having 3 to 17 carbon atoms are connected.
- the n-valent aromatic hydrocarbon group, the n-valent aromatic heterocyclic group, the aromatic hydrocarbon ring, and the aromatic heterocyclic ring may or may not have a substituent.
- A is a direct bond, the n-valent aliphatic hydrocarbon group, the n-valent alicyclic hydrocarbon group, the n-valent aromatic hydrocarbon group, the n-valent aromatic heterocyclic group, or An n-valent group in which 2 to 4 aromatic rings are connected.
- A is an n-valent aliphatic hydrocarbon group having 1 to 12 carbon atoms, it may be saturated or unsaturated, linear or branched. Specific examples include saturated or unsaturated methane, ethane, ethene, ethyne, propane, propene, propyne, butane, butene, butadiene, butyne, pentane, pentene, pentyne, hexane, heptane, octane, nonane, decane, etc. And an n-valent group obtained by removing n hydrogens from the aliphatic hydrocarbon.
- it is an n-valent aliphatic hydrocarbon group having 1 to 6 carbon atoms. More preferably, it is a divalent to tetravalent aliphatic hydrocarbon group generated by removing 2 to 4 hydrogens from an aliphatic hydrocarbon represented by CmH2m + 2.
- m is 1-6.
- A is an n-valent alicyclic hydrocarbon group having 3 to 12 carbon atoms, it may be saturated, unsaturated, or branched. Specific examples include removing n hydrogens from saturated or unsaturated alicyclic hydrocarbons such as cyclopropane, cyclobutane, cyclobutene, cyclobutadiene, cyclopentane, cyclopentene, cyclohexane, methylcyclohexane, cycloheptane, cyclooctane, etc. and n-valent groups.
- it is an n-valent aliphatic hydrocarbon group having 3 to 8 carbon atoms. More preferably, it is a divalent to tetravalent aliphatic hydrocarbon group generated by removing 2 to 4 hydrogens from an alicyclic hydrocarbon represented by CmH2m. Here, m is 3 to 8.
- A is an n-valent aromatic hydrocarbon group having 6 to 18 carbon atoms or an n-valent aromatic heterocyclic group having 3 to 17 carbon atoms
- specific examples of these groups include benzene, naphthalene, Fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene, pyridine, pyrimidine, triazine, indole, quinoline, isoquinoline, quinoxaline, naphthyridine, carbazole, acridine, phenanthroline, phenazine, benzofuran, dibenzofuran, xanthene, oxanthrene, phenoxazine, benzothiophene, And an n-valent group generated by removing n hydrogens from an aromatic compound selected from dibenzothiophene, thioxanthene, thianthrene, phenoxathiin and phenothiazine.
- it is an n-valent group formed by removing n hydrogens from an aromatic compound selected from benzene, indole, pyridine, pyrimidine, triazine, carbazole, benzofuran, dibenzofuran, benzothiophene, and dibenzothiophene.
- A is an n-valent group in which 2 to 4 aromatic rings selected from an aromatic hydrocarbon ring having 6 to 18 carbon atoms and an aromatic heterocyclic ring having 3 to 17 carbon atoms are connected
- the aromatic compound described in the case where A is an n-valent aromatic hydrocarbon group having 6 to 18 carbon atoms or an n-valent aromatic heterocyclic group having 3 to 17 carbon atoms Is an n-valent group formed by removing n hydrogen atoms from an aromatic compound formed by linking 2 to 4.
- aromatic compound that gives the aromatic ring examples include benzene, naphthalene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene, pyridine, pyrimidine, triazine, indole, quinoline, isoquinoline, quinoxaline, naphthyridine, carbazole, acridine, benzofuran, Dibenzofuran, phenoxazine, benzothiophene, dibenzothiophene, or phenothiazine are preferred. More preferred is benzene, indole, pyridine, pyrimidine, triazine, carbazole, benzofuran, dibenzofuran, benzothiophene, or dibenzothiophene.
- the aromatic hydrocarbon ring or the aromatic heterocyclic ring constituting the aromatic compound in which 2 to 4 aromatic rings are connected may be the same or different, and the aromatic hydrocarbon ring and the aromatic ring may be different from each other. Both of the heterocyclic rings may be included.
- aromatic compound in which 2 to 4 aromatic rings are connected include, for example, biphenyl, terphenyl, bipyridine, bipyrimidine, vitriazine, bistriazylbenzene, binaphthalene, phenylpyridine, diphenylpyridine, diphenylpyrimidine, diphenyltriazine , Phenyl carbazole, diphenyl carbazole, dicarbazolyl benzene, pyridyl carbazole, phenyl dibenzofuran, phenyl dibenzothiophene, and the like. It may be a ring or a central ring.
- the above aromatic hydrocarbon ring or aromatic heterocyclic ring may have a substituent in the same manner as the above n-valent aromatic hydrocarbon group and n-valent aromatic heterocyclic group.
- the preferred substituent is an alkyl group having 1 to 12 carbon atoms.
- an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 7 carbon atoms, or a diarylamino group having 12 to 20 carbon atoms. is there.
- the total number of substituents is 1-10.
- it is 1-6, more preferably 1-4.
- the aromatic hydrocarbon group, aromatic heterocyclic group or aromatic ring has two or more substituents, they may be the same or different.
- the carbon number of the aromatic hydrocarbon group, aromatic heterocyclic group or aromatic ring when it has a substituent, the carbon number of the substituent is not included.
- the aromatic hydrocarbon group, aromatic heterocyclic group or aromatic ring is a substituted aromatic hydrocarbon group, substituted aromatic heterocyclic group or substituted aromatic ring
- the total number of carbon atoms is In the case of a hydrogen group or a substituted aromatic hydrocarbon ring, 6 to 50 is preferable, and 6 to 30 is more preferable.
- the total number of carbon atoms is preferably 3 to 50, more preferably 4 to 30.
- an n-valent group generated from an aromatic compound in which 2 to 4 aromatic rings are connected is represented by the following formula, for example, in the case of a divalent group.
- each R is independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, Represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or an aromatic heterocyclic group having 3 to 17 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 1 to 12 carbon atoms, A 6-12 aromatic hydrocarbon group or a C3-C12 aromatic heterocyclic group.
- alkyl group and cycloalkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, cyclohexyl group, and methylcyclohexyl.
- Group, etc. and may be linear or branched. Preferred are methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, and cyclohexyl group.
- aromatic hydrocarbon group having 6 to 18 carbon atoms and the aromatic heterocyclic group having 3 to 17 carbon atoms include benzene, naphthalene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene, pyridine, pyrimidine, and triazine.
- Excluded groups and the like are exemplified.
- R ′ each independently represents hydrogen, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, preferably hydrogen, an alkyl group having 1 to 6 carbon atoms, or An alkoxy group having 1 to 6 carbon atoms.
- Specific examples of the alkyl group or alkoxy group include methyl group, ethyl group, propyl group, butyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, etc.
- the alkyl chain may be linear or branched.
- a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a methoxy group, an ethoxy group, a propoxy group, and a butoxy group are preferable.
- E represents oxygen or sulfur.
- n represents an integer of 2 to 4, preferably 2 or 3.
- the skeleton in which E is O can be synthesized by the following reaction formula with reference to the synthesis example shown in WO2009-145016.
- the compound represented by the general formula (1) can be synthesized by substituting iodine of various compounds obtained by the above reaction formula with a corresponding linking group by a coupling reaction such as Suzuki coupling. .
- the carbazole compound represented by the general formula (1) has an excellent organic electric field by being contained in at least one organic layer of an organic EL device in which an anode, a plurality of organic layers and a cathode are laminated on a substrate.
- a light emitting element is provided.
- the organic layer to be contained a light emitting layer, a hole transport layer, an electron transport layer or a hole blocking layer is suitable. More preferably, it is added as a host material of 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 at least one organic layer contains the carbazole compound.
- a carbazole compound represented by the general formula (1) 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 an example of the structure of a general organic EL device.
- 1 is a substrate
- 2 is an anode
- 3 is a hole injection layer
- 4 is a hole transport layer
- 5 is a light emitting layer
- 6 is an electron transport.
- Layers 7, 7 each represent 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 emit light. 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.
- electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO.
- conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO.
- an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form 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
- Suitable are a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, aluminum and the like.
- 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 phosphorescent light emitting layer and includes a phosphorescent 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. The numbers of patent gazettes and the like are described below.
- 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 preferably 0.1 to 50% by weight, and more preferably 1 to 30% by weight.
- the material used for the light emitting layer may be a host material other than the carbazole compound.
- a carbazole 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.
- Such other 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, indolocarbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, Pyrazolone derivatives, phenylenediamine derivatives, 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, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivative
- Tetracarboxylic anhydride Tetracarboxylic anhydride, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, various metal complexes represented by metal complexes of benzoxazole and benzothiazole derivatives, polysilane compounds, poly (N-vinylcarbazole) derivatives, Examples include aniline-based copolymers, thiophene oligomers, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, and polyfluorene derivatives.
- the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission.
- the injection layer can be provided as necessary.
- the hole blocking layer has a function of an electron transport layer in a broad sense, and is composed of a hole blocking material that has a function of transporting electrons and has a very small ability to transport holes, and transports holes while transporting electrons. The probability of recombination of electrons and holes can be improved by blocking.
- the carbazole compound represented by the general formula (1) for the hole blocking layer
- a known hole blocking layer material is used. Also good.
- 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. By blocking holes while transporting holes, it is established that electrons and holes are recombined. Can be improved.
- 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.
- Examples of the material for the exciton blocking layer include 1,3-dicarbazolylbenzene (mCP) and bis (2-methyl-8-quinolinolato) -4-phenylphenolato aluminum (III) (BAlq). It is done.
- mCP 1,3-dicarbazolylbenzene
- BAlq bis (2-methyl-8-quinolinolato) -4-phenylphenolato aluminum
- 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. Although it is preferable to use the carbazole compound represented by General formula (1) for a positive hole transport layer, arbitrary things can be selected and used from a conventionally well-known compound.
- Examples of known hole transport materials that can be used include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, Examples include styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers. Triazole derivatives, oxadiazole derivatives, imidazole derivatives, aryl An amine derivative is preferably used, and an arylamine derivative is more preferably used.
- 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
- the carbazole compound represented by the general formula (1) according to the present invention any one of conventionally known compounds can be selected and used. Fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like can be mentioned.
- 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.
- a carbazole compound as a phosphorescent light emitting device material was synthesized by the following route.
- corresponds to the number attached
- intermediate (A2) 8.62 g (0.0418 Nmol) and N-methyl-pyrrolidone 230 ml were added, and potassium carbonate 11.56 g (0.0836 mol) was added with stirring at room temperature. After stirring at 180 ° C. for 3 hours, the mixture was cooled to room temperature, and potassium carbonate was filtered off. After adding 900 ml of distilled water to the filtrate and stirring at room temperature, the precipitated solid was filtered off. The obtained solid was dissolved in dichloromethane, and the organic layer was washed with distilled water (30 ml ⁇ 3).
- nickel chloride (II) hexahydrate 4.16 g (0.0152 mol), triphenylphosphine 16.34 g (0.0623 mol), and dimethylformamide 50 ml were added and deaerated. 1.29 g (0.0198 mol) of zinc was added and stirred at 60 ° C. for 20 minutes. 50 ml of a dimethylformamide solution in which 5.84 g (0.0127 mol) of intermediate (A5) was dissolved was added and stirred at 90 ° C. for 4 hours. The reaction solution was cooled to room temperature, poured into 300 ml of water, and stirred at room temperature for 2 hours.
- Example 3 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa by a vacuum evaporation method on a glass substrate on which an anode made of an ITO substrate having a thickness of 110 nm was formed.
- CuPc was formed to a thickness of 20 nm on ITO.
- NPB was formed to a thickness of 20 nm as a hole transport layer.
- the compound (1) as the host material and Ir (ppy) 3 as the dopant were co-deposited on the hole transport layer from different vapor deposition sources to form a light emitting layer with a thickness of 30 nm. At this time, the concentration of Ir (ppy) 3 was 10 wt%.
- Alq3 was formed to a thickness of 40 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 light emission characteristics as shown in Table 1.
- Table 1 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 540 nm, indicating that light emission from Ir (ppy) 3 was obtained.
- Examples 4 to 11 In the same manner as in Example 1, compounds 8, 11, 17, 18, 20, and 31 were synthesized, and as a host material of the light emitting layer of Example 3, instead of compound 1, compounds 8, 11, 17, 18, 20 , 31, or 40 was used to produce an organic EL device in the same manner as in Example 3.
- the maximum wavelength of each device emission spectrum was 540 nm, and it was found that light emission from Ir (ppy) 3 was obtained.
- Examples 12 to 13 An organic EL device was produced in the same manner as in Example 3 except that CBP or Compound H-1 was used as the host material for the light emitting layer in Example 3.
- the maximum wavelength of the device emission spectrum was 535 nm (Example 12) or 530 nm (Example 13), and it was identified that light emission from Ir (ppy) 3 was obtained.
- Example 3 has improved initial characteristics over Examples 12 and 13 (comparison).
- the organic EL device characteristics are improved by using, for the organic EL device, a compound having carbazole at position 1 of dibenzothiophene or dibenzofuran and a specific substituent at positions 2 to 7 of carbazole. I understand that.
- the EL device characteristics of Examples 4 to 11 are good, and the superiority of the carbazole compound represented by the general formula (1) is also shown here.
- the carbazole compound represented by the general formula (1) used in the organic electroluminescence device of the present invention has 2 to 4 skeletons bonded to the 1-position of dibenzothiophene or dibenzofuran at the N-position of carbazole at the 3-position of carbazole.
- IP ionization potential
- EA electron affinity
- T1 triplet energy
- the carbazole compound is considered to be capable of improving the stability in each active state of oxidation, reduction, and excitation, and at the same time has good amorphous characteristics. From the above, it is possible to realize an organic EL element having a long driving life and high durability.
- the organic EL device according to the present invention has practically satisfactory levels in terms of light emission characteristics, driving life and durability, flat panel display (mobile phone display device, in-vehicle display device, OA computer display device, television, etc.), surface light emission, etc. 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.
Abstract
Description
Aは直接結合、-O-、-S-、-Se-、>N-、>N-R、>Si-(R)2、>Ge-(R)2、炭素数1~12のn価の脂肪族炭化水素基、炭素数3~12のn価の脂環式炭化水素基、炭素数6~18のn価の芳香族炭化水素基、炭素数3~17のn価の芳香族複素環基、又は炭素数6~18の芳香族炭化水素環、及び炭素数3~17の芳香族複素環から選ばれる芳香族環が2~4つ連結されたn価の基であるが、上記n価の芳香族炭化水素基、n価の芳香族複素環基、又は上記芳香族環は置換基を有してもよい。
Rはそれぞれ独立に炭素数1~20のアルキル基、炭素数1~20のシクロアルキル基、炭素数6~18の芳香族炭化水素基、炭素数3~17の芳香族複素環基を表す。
R’はそれぞれ独立に水素、炭素数1~12のアルキル基、又は炭素数1~12のアルコキシ基を表す。
Eは酸素または硫黄を表す。
nは2~4の整数を表す。
一般式(1)中、nは2又は3の整数であることが好ましい。
ここで、上記n価の芳香族炭化水素基、n価の芳香族複素環基、芳香族炭化水素環及び芳香族複素環は、置換基を有しても、有さなくともよい。
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については、特に制限はなく、従来から有機EL素子に慣用されているものであればよく、例えば、ガラス、透明プラスチック、石英などからなるものを用いることができる。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3-ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが、通常10~1000nm、好ましくは10~200nmの範囲で選ばれる。
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~5μm、好ましくは50~200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。
発光層は燐光発光層であり、燐光発光ドーパントとホスト材料を含む。燐光発光ドーパント材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金属錯体を含有するものがよい。具体的には以下の特許公報に記載されている化合物が挙げられるが、これらの化合物に限定されない。以下に、特許公報等の番号を記す。
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。
電子阻止層とは、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料から成り、正孔を輸送しつつ電子を阻止することで電子と正孔が再結合する確立を向上させることができる。
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、本層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は発光層に隣接して陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、正孔輸送層は単層又は複数層設けることができる。
電子輸送層とは電子を輸送する機能を有する材料からなり、電子輸送層は単層又は複数層設けることができる。
APCI-TOFMS, m/z 665 [M+1]、1H-NMR測定結果(測定溶媒:THF-d8)を図2に示す。
APCI-TOFMS, m/z 741 [M+1]、1H-NMR測定結果(測定溶媒:THF-d8)を図3に示す。
膜厚110nmのITO基板からなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-5Paで積層させた。まず、ITO上にCuPcを20 nmの厚さに形成した。次に、正孔輸送層としてNPBを20 nmの厚さに形成した。次に、正孔輸送層上に、ホスト材料としての化合物(1)とドーパントとしてのIr(ppy)3とを異なる蒸着源から、共蒸着し、30 nmの厚さに発光層を形成した。この時、Ir(ppy)3の濃度は10 wt%であった。次に電子輸送層としてAlq3を40 nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を1nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を70nmの厚さに形成し、有機EL素子を作製した。
実施例1と同様に、化合物8、11、17、18、20、及び31を合成し、実施例3の発光層のホスト材料として、化合物1に代えて化合物8、11、17、18、20、31、又は40を用いた以外は実施例3と同様にして有機EL素子を作成した。各々の素子発光スペクトルの極大波長は540 nmであり、Ir(ppy)3からの発光が得られていることがわかった。
実施例3における発光層のホスト材料としてCBP、又は化合物H-1を用いた以外は実施例3と同様にして有機EL素子を作成した。素子発光スペクトルの極大波長は535 nm(例12)又は530 nm(例13)であり、Ir(ppy)3からの発光が得られていると同定された。
Claims (4)
- 基板上に、陽極、有機層及び陰極が積層されてなる有機電界発光素子において、発光層、正孔輸送層、電子輸送層、及び正孔阻止層からなる群れから選ばれる少なくとも一つの層に一般式(1)で表されるカルバゾール化合物を含有させたことを特徴とする有機電界発光素子。
ここで、
Aは直接結合、-O-、-S-、-Se-、>N-、>N-R、>Si-(R)2、>Ge-(R)2、炭素数1~12のn価の脂肪族炭化水素基、炭素数3~12のn価の脂環式炭化水素基、炭素数6~18のn価の芳香族炭化水素基、炭素数3~17のn価の芳香族複素環基、又は炭素数6~18の芳香族炭化水素環及び炭素数3~17の芳香族複素環から選ばれる芳香族環が2~4つ連結されたn価の基である。ここで、上記該芳香族炭化水素基、該芳香族複素環基、該芳香族炭化水素環及び該芳香族複素環は、置換基を有してもよい。
Rはそれぞれ独立に炭素数1~20のアルキル基、炭素数1~20のシクロアルキル基、炭素数6~18の芳香族炭化水素基、炭素数3~17の芳香族複素環基を表し、
R’はそれぞれ独立に水素、炭素数1~12のアルキル基、又は炭素数1~12のアルコキシ基を表し、
Eは酸素または硫黄を表し
nは2~4の整数を表す。 - 一般式(1)において、Aが直接結合、炭素数1~6のn価の脂肪族炭化水素基、炭素数3~8のn価の脂環式炭化水素基、炭素数6~18のn価の芳香族炭化水素基、炭素数3~17のn価の芳香族複素環基、又は炭素数6~18の芳香族炭化水素環及び炭素数3~17の芳香族複素環から選ばれる芳香環から選ばれる芳香族環が2~4つ連結されたn価の基の何れかである請求項1に記載の有機電界発光素子。
- Aが、直接結合、n価の芳香族炭化水素基、n価の芳香族複素環基、又は芳香族環が2~4つ連結されたn価の基の何れかであり、nは2又は3である請求項2に記載の有機電界発光素子。
- 一般式(1)で表されるカルバゾール化合物を含有させた層が、燐光発光ドーパントを含有する発光層である請求項1~3のいずれかに記載の有機電界発光素子。
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Publication number | Publication date |
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EP2757608A1 (en) | 2014-07-23 |
KR20140074936A (ko) | 2014-06-18 |
TWI559592B (zh) | 2016-11-21 |
JP5972884B2 (ja) | 2016-08-17 |
TW201330344A (zh) | 2013-07-16 |
EP2757608A4 (en) | 2015-08-05 |
US20140203269A1 (en) | 2014-07-24 |
CN103907217A (zh) | 2014-07-02 |
CN103907217B (zh) | 2016-10-12 |
EP2757608B1 (en) | 2016-03-23 |
JPWO2013038843A1 (ja) | 2015-03-26 |
US9142785B2 (en) | 2015-09-22 |
KR101992874B1 (ko) | 2019-06-26 |
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