WO2007069569A1 - 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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Definitions
- the present invention relates to a material for an organic electoluminescence device and an organic electoluminescence device using the same, and more particularly, an organic electorum having high luminous efficiency, excellent pixel resistance, excellent heat resistance, and a long lifetime.
- the present invention relates to an oral luminescence element material and an organic electroluminescence element.
- Organic-electric-luminescence elements may be abbreviated as EL, and the recombination energy between holes injected from the anode and electrons injected from the cathode by applying an electric field. It is a self-luminous element that utilizes the principle that fluorescent substances emit light.
- Eastman's Kodak's CW Tang et al. Reported low-voltage-driven organic EL devices using stacked devices (CW Tang, SA Vanslyke, Applied Physics Letters, 51 ⁇ , 913, 1987, etc.) Since then, research on organic EL devices using organic materials as constituent materials has been actively conducted. Tang et al.
- the organic EL device has a two-layer structure of a hole transport (injection) layer and an electron transport luminescent layer, or a hole transport (injection) layer, a luminescent layer, and an electron transport (injection) layer.
- the three-layer type is well known. In such a multilayer structure element, in order to increase the recombination efficiency of injected holes and electrons, the element structure and the formation method are devised.
- Light-emitting materials for organic EL devices include light-emitting materials such as tris (8-quinolinolato) aluminum complexes, chelate complexes, coumarin derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives, oxadiazole derivatives, and the like. And from them from blue It has been reported that light emission in the visible region up to red can be obtained, and realization of a color display element is expected (see, for example, Patent Document 1, Patent Document 2, Patent Document 3, etc.).
- Non-Patent Document 1 a fluorescent material for the light emitting layer of an organic EL element
- Non-Patent Document 2 a fluorescent material for the light emitting layer of an organic EL element
- high emission efficiency is achieved by using the singlet state and triplet state of the excited state of the organic phosphorescent material in the light emitting layer of the organic EL element.
- electrons and holes recombine in an organic EL device, it is thought that singlet excitons and triplet excitons are generated at a ratio of 1: 3 due to the difference in spin multiplicity. If a light-emitting material is used, light emission efficiency of 3 to 4 times that of an element using only fluorescence can be considered.
- an anode, a hole transport layer, an organic light emitting layer, an electron transport layer (hole blocking) are sequentially arranged so that the triplet excited state or triplet exciton is not quenched.
- Layer an electron transport layer, and a cathode are used, and a host compound and a phosphorescent compound have been used for the organic light emitting layer (see, for example, Patent Document 4 and Patent Document 5).
- 4,4-N, N-dicarbazole biphenyl is used as a host compound. This compound has a glass transition temperature of 110 ° C or lower, and further has a force rubazole molecular skeleton. Because the biphenyl skeleton is bonded to the nitrogen atom on the center line of the crystal! And / or the crystal is crystallized due to too good symmetry. There was a problem that occurred.
- Patent Document 6 a device having a fluorescent benzofuran compound and a dibenzofuran compound is disclosed.
- a compound having a substituent at the 7-position of benzofuran and the 4- or 6-position of dibenzofuran there is no description of its specific performance.
- a compound having a 4-biphenylindole structure as a substituent at the 4-position of benzofuran is exemplified, and an example of using as a host of an iridium complex which is a blue-green phosphorescent material is shown. It is shown (Patent Document 7).
- Patent Document 8 a compound having a benzothiophene skeleton in which an anthracene skeleton is essential is described.
- Patent Document 9 a furan compound in which an anthracene skeleton is essential is disclosed.
- a benzofuran compound bonded to the pyrene skeleton is also shown! /, (Patent Document 10), but the triplet energy gap is also narrow in the pyrene skeleton, which makes it difficult to apply to phosphorescent organic EL devices. It seems that the example is not described.
- Patent Document 11 describes a dibenzofuran compound having a benzotriazole skeleton! Although this compound also has a narrow triplet energy gap, it is difficult to apply to phosphorescent organic EL devices. In addition, the examples are also described.
- Patent Documents 12 and 13 Although dibenzo compounds having two or more amino groups have been described (Patent Documents 12 and 13), there is no description regarding examples as host materials, and the effects are unclear.
- Patent Document 1 Japanese Patent Application Laid-Open No. 8-239655
- Patent Document 2 Japanese Patent Laid-Open No. 7-138561
- Patent Document 3 Japanese Patent Laid-Open No. 3-200289
- Patent Document 4 U.S. Patent No. 6,097,147
- Patent Document 5 International Publication WO01Z41512
- Patent Document 6 JP-A-5-109485
- Patent Document 7 Japanese Unexamined Patent Application Publication No. 2004-214050
- Patent Document 8 Japanese Patent Laid-Open No. 2004-002351
- Patent Document 9 Japanese Unexamined Patent Application Publication No. 2005-047868
- Patent Document 10 International Publication WO04Z096945
- Patent Document 11 International Publication WO05Z054212
- Patent Document 12 JP-A-7-53950
- Patent Document 13 Japanese Patent Laid-Open No. 2001-43979
- Non-Patent Literature 1 D.F.O'Brien and M.A.Baldo et al 'Improved energy transfering electr ophosphorescent devices "Applied Physics letters Vol. 74 No.3, pp442 ⁇ 444, founded y 18, 1999
- Non-Patent Document 2 M.A.Baldo et al "Very high-efficiency green organic light-emitting de vices based on electrophosphorescence" Applied Physics letters Vol. 75 No. 1, pp4 -6, July 5, 1999
- the present invention has been made to solve the above-described problems.
- An organic EL element material having high luminous efficiency, no pixel defects, excellent heat resistance, and a long lifetime, and the use thereof are used.
- the object is to provide an organic EL device.
- the present invention provides an organic EL device material having a compound power represented by any one of the following general formulas (1) to (14).
- R ′, R ′ and R to R each independently represent a hydrogen atom, a halogen atom or a substituent.
- An optionally substituted alkyl group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group not having a benzotriazole skeleton having 3 to 60 carbon atoms, and an optionally substituted carbon It has an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 60 carbon atoms that may have a substituent, an aryloxy group having 6 to 60 carbon atoms that may have a substituent, and a substituent. May have a aralkyl group having 7 to 60 carbon atoms, an alkenyl group having 2 to 40 carbon atoms which may have a substituent, an alkylamino group having 1 to 40 carbon atoms and a substituent.
- An optionally substituted ketoaryl group having 7 to 40 carbon atoms, an optionally substituted halogenated alkyl group having 1 to 40 carbon atoms or a cyano group; is there.
- R 'and R', R and R, R and R are bonded to each other to form a saturated or unsaturated cyclic structure
- X represents a sulfur atom, an oxygen atom, or a substituted silicon atom represented by SiRaRb, and Ra and Rb each independently represents an alkyl group having 1 to 40 carbon atoms.
- Y is an alkyl group having 1 to 40 carbon atoms which may have a substituent, a benzotriazole skeleton having 3 to 60 carbon atoms which may have a substituent, a heterocyclic group or a substituent.
- R to R are independently the same as R ′ and R in the general formula (1).
- R is an anthracene skeleton. If any of R to R is an amino group,
- Saturated or unsaturated cyclic structures are formed by adjacent R to R and R to R
- X is the same as that in the general formula (1).
- Y ' may have a substituent, an alkyl group having 1 to 40 carbon atoms, or a substituent! ⁇ Carbonate No benzotriazole skeleton having 3 to 60 carbon atoms, having a heterocyclic group or a substituent, alkoxy group having 1 to 40 carbon atoms, or an optionally substituted carbon number 6
- R to R are independently the same as R to R in the general formula (2).
- ⁇ R is a hydrogen atom and any of R ⁇ R is an amino group
- annular structure may be formed!
- R to R are independently the same as R to R in the general formula (2),
- R to R are independently the same as R to R in the general formula (2).
- R ⁇ R When either is an amino group, only one of R to R is an amino group.
- 7 and 8 may form a saturated or unsaturated cyclic structure.
- R to R are independently the same as R to R in the general formula (2).
- R to R are independently the same as R to R in the general formula (2).
- R ⁇ R When any of these is an amino group, only one of R to R is an amino group.
- R ⁇ : R, R ⁇ : R, R ⁇ : R, R or R ⁇ R adjacent to each other are saturated or
- R to R are the same as R to R in the general formula (2), respectively.
- R to R is an amino group
- only one of R to R is an amino group.
- Saturated or unsaturated cyclic structures may be formed.
- the present invention provides an organic EL device in which an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between a cathode and an anode, and at least one of the organic thin film layers is
- the present invention provides an organic EL element containing a material for an organic EL element. The invention's effect
- the organic EL device material having the compound power represented by the general formula (1) of the present invention is used, an organic EL device having high luminous efficiency and excellent heat resistance without pixel defects and having a long lifetime can be obtained. It is done. For this reason, the organic EL device of the present invention is extremely useful as a light source for various electronic devices.
- the organic EL device material of the present invention comprises a compound represented by the following general formulas (1) to (14).
- R ′, R ′ and R to R are each independently a hydrogen atom, a halogen atom,
- ⁇ ⁇ ⁇ ⁇ ⁇ Alkoxy group having 1 to 40 carbon atoms, aryl group having 6 to 60 carbon atoms which may have a substituent, aryl group having 6 to 60 carbon atoms which may have a substituent You may have a substituent! May have a aralkyl group having 7 to 60 carbon atoms and a substituent, may have an alkenyl group having 2 to 40 carbon atoms, and may have a substituent.
- alkylamino group having 1 to 40 carbon atoms and a substituent may be substituted.
- Aralkylamino group having 7 to 60 carbon atoms, alkylsilyl group having 3 to 20 carbon atoms which may have a substituent, and arylenesilyl group having 8 to 40 carbon atoms which may have a substituent These may be a substituent, a C7 to C40 ketoaryl group, a C1 to C40 halogenated alkyl group or a cyano group which may have a substituent.
- R 'and R', R and R, R and R are bonded together and saturated
- an unsaturated cyclic structure may be formed.
- X represents a sulfur atom, an oxygen atom, or a substituted silicon atom represented by Si RaRb, and Ra and Rb each independently represents an alkyl group having 1 to 40 carbon atoms.
- Y may have a substituent, an alkyl group having 1 to 40 carbon atoms, may have a substituent, does not have a benzotriazole skeleton having 3 to 60 carbon atoms, is a heterocyclic group, or a substituent. May have an alkoxy group having 1 to 40 carbon atoms, a substituent, an aryl group having 6 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms which may have a substituent.
- substituent Aralkyl group having 7 to 60 carbon atoms substituent may be present, alkyl group having 2 to 40 carbon atoms, alkyl group having 1 to 40 carbon atoms which may have substituents A C7-C60 aralkylamino group which may have a substituent, a C3-C20 alkylsilyl group which may have a substituent, and a C8-C40 which may have a substituent. It is an arylsilyl group or a halogenated alkyl group having 1 to 40 carbon atoms which may have a substituent.
- R to R are each independently R ′, R ′ and R in the general formula (1).
- R is an anthracene skeleton and any of R to R is an amino group
- R to R is an amino group. Adjacent at R to R, R to R
- X is the same as that in the general formula (1).
- Y ′ may have a substituent, an alkyl group having 1 to 40 carbon atoms, may have a substituent, does not have a benzotriazole skeleton having 3 to 60 carbon atoms, is a heterocyclic group, is substituted May have a group, an alkoxy group having 1 to 40 carbon atoms, a substituent, an aryl group not having a pyrene skeleton having 6 to 60 carbon atoms, or a carbon that may have a substituent.
- R to R are independently the same as R to R in the general formula (2).
- R to R is a hydrogen atom, and any of R to R is amino
- Adjacent ones of R or R and R form a saturated or unsaturated cyclic structure.
- R to R are each independently R to R in the general formula (2).
- R to R or R to R in the general formula (6), R to R adjacent to each other, or R to R
- a saturated or unsaturated cyclic structure may be formed.
- X is the same as that in the general formula (2).
- R to R are each independently R to R in the general formula (2).
- R to R adjacent to each other, or R and R form a saturated or unsaturated cyclic structure
- X is the same as that in the general formula (2).
- R to R are independently the same as R to R in general formula (2).
- X is the same as that in the general formula (2).
- R to R are each independently R in the general formula (2).
- X is the same as that in the general formula (2).
- R to R are each independently R in the general formula (2). Same as ⁇ R.
- any of R to R is an amino group, one of R to R
- halogen atoms examples include fluorine, chlorine, bromine and iodine.
- alkyl group having 1 to 40 carbon atoms which may have a substituent of R ′, R ′, R to R, Y and Y ′;
- Benzotria having 3 to 60 carbon atoms which may have a substituent of R ', R', R to R, Y and Y '
- heterocyclic group having no sol skeleton examples include 1 pyrrolyl group, 2 pyrrolyl group, 3 pyrrolyl group, pyradyl group, 2-pyridinyl group, 1 imidazolyl group, 2-imidazolyl group, 1 pyrazolyl group, 1 indoli- 2-indolidyl group, 3-indolidyl group, 5-indolidyl group, 6-indolidyl group, 7-indolidyl group, 8-indolidyl group, 2 imidazopyridyl group, 3 Imidazopyridyl group, 5 Imidazopyridyl group, 6-Imidazopyridyl group, 7-Imidazopyridyl group, 8-Imidazopyridyl group, 3-Pyridyl group, 4 Pyridyl group, 1-Indolyl group 2—Indolyl group, 3—Indolyl group, 4 —Indolyl group
- 2-pyridyl group, 1-indolidinyl group, 2-indolidyl group, 3-indolidyl group, 5-indolidyl group, 6-indolidyl group, 7-indolidinyl group are preferable.
- R ', R', R to R, Y and Y ' An optionally substituted alkoxy group having 1 to 40 carbon atoms
- phenol group, 1 naphthyl group, 2 naphthyl group, 9 phenanthryl group, 2 biphenylyl are preferable.
- Examples of the aryl group not having a pyrene skeleton having 6 to 60 carbon atoms which may have a substituent of Y ′ include those other than those having a pyrene skeleton among the aryl groups.
- the Si group is a group represented by OAr, and specific examples of Ar include the same as those described for the aryl group, and preferred examples are also the same.
- Aralkyl having 7 to 60 carbon atoms which may have a substituent of R ', R', R to R, Y and Y '
- Examples of the group include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-butyl group, an ⁇ -naphthylmethyl group, 1 ⁇ -naphthylethyl, 2-a naphthylethyl, 1 a naphthylisopropyl, 2-a naphthylisopropyl, 13 naphthylmethyl, 1- ⁇ naphthylethyl, 2- ⁇ naphthylethyl, 1- ⁇ naphthylisopropyl, 2— ⁇ -naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, ⁇ methylbenzyl group, m-methylbenzyl group, o methylbenzyl group,
- benzyl group p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group.
- benzyl group p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group.
- R 2 R 1, R to R, Y and Y ′ optionally having a carbon number of 2 to 40 carbons
- Examples of the group include vinyl group, aralkyl group, 1-buturyl group, 2 butyr group, 3 butyl group, 1,3 butaneger group, 1-methylvinyl group, styryl group, and 2,2 diphenyl -L group, 1,2-diphenyl group, 1-methylaryl group, 1,1-dimethylaryl group Group, 2-methylaryl, 1-furaryl, 2-phenolyl, 3-phenolyl, 3,3-diphenylyl, 1,2-dimethylaryl, 1-loop -Butene group, 3-phenyl-1-butenyl group, etc., preferably styryl group, 2,2-diphenyl group, 1,2-diphenyl group and the like.
- R ', R', R to R and Y optionally having 1 to 40 alkylamino groups
- the aralkylamino group having 7 to 60 carbon atoms which may have a substituent is represented by —NQ Q, and Q
- 1 2 1 and Q are each independently the alkyl group, the aryl group,
- R ', R', R to R, Y and Y ' optionally having an alkyl group having 3 to 20 carbon atoms
- Examples of the group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a butyldimethylsilyl group, and a propyldimethylsilyl group.
- R ', R', R to R, Y and Y ' may have a substituent of 8 to 40 carbon atoms
- Examples of the group include tri-furylsilyl group, full-dimethylsilyl group, and tert-butyldiphenylsilyl group.
- R 7, R 7, and R 7 to R 7 R may be substituted with 7 to 40 carbon atoms.
- R 1, R 1, R to R, Y and Y ′ which may have a substituent group having 1 to 40 carbon atoms
- alkyl group examples include those in which at least one hydrogen atom of the alkyl group is substituted with a halogen atom, and examples thereof are also the same.
- Examples of the alkyl group having 1 to 40 carbon atoms of Ra and Rb include the same ones as the alkyl group, preferably a methyl group, an ethyl group, a propyl group and a butyl group.
- the organic EL device material of the present invention is preferably a host material contained in the light emitting layer of the organic EL device.
- the organic EL device of the present invention is an organic EL device in which an organic thin film layer composed of one or more layers having at least a light emitting layer is sandwiched between a cathode and an anode. At least one layer contains the organic EL device material of the present invention.
- the light-emitting layer has a phosphorescent light-emitting material strength with a host material, and the host material is made of the organic EL element material.
- the organic EL element wherein the light emitting layer contains a host material and a phosphorescent light emitting material, and the light emitting wavelength of the phosphorescent light emitting material has an emission peak of 500 nm or less.
- a metal complex such as an iridium complex, an osmium complex, or a platinum complex is preferable because the external quantum efficiency of the light emitting device having a high phosphorescence quantum yield can be further improved.
- Orthometalated lysium complexes are most preferred, with platinum complexes being more preferred.
- the ortho metal i metal complex the following iridium complexes are preferred.
- the light emitting layer preferably contains a host material and a phosphorescent light emitting material, and the phosphorescent light emitting material is a light emitting material having a metal-carbene carbon bond.
- the light emitting layer preferably contains a host material and a phosphorescent light emitting material, and the phosphorescent light emitting material is preferably a light emitting material having a phenylimidazole skeleton.
- the light-emitting layer preferably contains a host material and a phosphorescent light-emitting material, and the phosphorescent light-emitting material is a light-emitting material having a phenylvirazole skeleton.
- the element is preferably such that the material for the organic electroluminescence device is a host material contained in the light emitting layer of the organic electroluminescence device.
- the material for the organic electoluminescence device is a material contained in the hole transport layer of the organic EL device.
- the material for the organic electoluminescence device is a material contained in the electron transport layer or the hole barrier layer of the organic EL device.
- a reducing dopant is added to the interface region between the cathode and the organic thin film layer.
- Examples of the reducing dopant include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, and rare earth metal compounds. At least one kind selected.
- alkali metal examples include Na (work function: 2.36 eV), K (work function: 2.28 eV), R b (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like. Particularly preferred are those having a work function of 2.9 eV or less. Of these, K, Rb and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.
- alkaline earth metal examples include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV), and the like. Particularly preferred is 9 eV or less.
- rare earth metal examples include Sc, Y, Ce, Tb, and Yb, and those having a work function of 2.9 eV or less are particularly preferable.
- preferred metals are capable of improving the light emission luminance and extending the life of organic EL devices by adding a relatively small amount to the electron injection region, which has a particularly high reducing ability.
- alkali metal compound examples include alkali oxides such as Li 0, Cs 0, and KO, LiF, N Examples include alkali halides such as aF, CsF, KF, etc., and alkalis such as LiF, Li 0, NaF
- alkaline earth metal compound examples include BaO, SrO, CaO, and Ba Sr ⁇ ⁇ (0 ⁇ ⁇ 1) mixed with these, Ba Ca O (0 ⁇ x ⁇ 1), BaO, SrO, CaO is preferred x l- ⁇ x 1- ⁇
- rare earth metal compound examples include YbF, ScF, ScO, YO, CeO, GdF, and TbF.
- the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are particularly those containing at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as the metal ion. There is no limitation.
- the ligands include quinolinol, benzoquinolinol, ataridinol, phenanthridinol, hydroxyphenylazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxy Phenylvinylidine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfulborane, bipyridyl, phenanthrin, phthalocyanine, porphyrin, cyclopentagen, 13-diketones, azomethines, and their derivatives Is preferable, but is not limited thereto.
- the reducing dopant it is preferable to form a layered or island-like shape in the interface region.
- the reducing dopant When forming the reducing dopant in layers, after forming the light emitting material or electron injecting material, which is the organic layer at the interface, into layers, the reducing dopant is vapor-deposited alone by resistance heating vapor deposition. Form at ⁇ 15 nm.
- the reducing dopant When forming the reducing dopant in an island shape, after forming the light emitting material or electron injecting material, which is an organic layer at the interface, in an island shape, the reducing dopant is vapor-deposited alone by resistance heating vapor deposition. It is formed with a thickness of O.05 to lnm. Moreover, as a ratio of the main component and the reducing dopant in the organic EL device of the present invention, the main component: the reducing dopant is preferably 5: 1 to 1: 5 in a molar ratio, and 2: 1 to 1: 2. Is more preferable.
- the organic EL device of the present invention preferably has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer contains a nitrogen-containing ring derivative as a main component.
- an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
- this nitrogen-containing ring derivative for example, a compound represented by the general formula (A) is preferable.
- R 2 to R 7 are each independently a hydrogen atom, a halogen atom, an oxy group, an amino group, or a hydrocarbon group having 1 to 40 carbon atoms, and these may be substituted.
- Examples of the halogen atom include the same ones as described above.
- Examples of the amino group which may be substituted include those similar to the alkylamino group, arylamino group and aralkylamino group.
- Examples of the hydrocarbon group having 1 to 40 carbon atoms include a substituted or unsubstituted alkyl group, alkenyl group, cycloalkyl group, alkoxy group, aryl group, heterocyclic group, aralkyl group, aryloxy group, alkoxycarbo group. And the like.
- Examples of the alkyl group, alkenyl group, cycloalkyl group, alkoxy group, aryl group, heterocyclic group, aralkyl group, and aryloxy group include those described above.
- COOY ′, and examples of Y ′ include those similar to the alkyl group.
- M is aluminum (A1), gallium (Ga) or indium (In), and is preferably In.
- L in the general formula (A) is a group represented by the following general formula ( ⁇ ') or ( ⁇ ").
- R 8 to R 12 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure.
- R 13 to R 27 are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure.
- examples of the divalent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, diphenylmethane— 2, 2,-diyl group, diphenylane-3, 3,-diyl group, diphenylpropan 4, 4 'diyl group and the like.
- a nitrogen-containing 5-membered ring derivative is also preferable.
- the nitrogen-containing 5-membered ring include an imidazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a thiadiazole ring, Oxatriazole ring, thiatriazole ring, etc.
- nitrogen-containing 5-membered ring derivatives are benzimidazole ring, benzotriazole ring, pyridinoimidazole ring, pyrimidinoimidazole ring, pyridazinoimidazole ring, Preferably, it is represented by the following general formula (B). [0079] [Chemical 42]
- L B represents a divalent or higher valent linking group, for example, carbon, cage, nitrogen, boron, oxygen, sulfur, metal (for example, barium, beryllium), aromatic carbonization.
- examples thereof include a hydrogen ring and an aromatic complex ring.
- a carbon atom, a nitrogen atom, a carbon atom, a boron atom, an oxygen atom, a sulfur atom, an aryl group, and an aromatic heterocyclic group are preferred.
- a silicon atom, an aryl group, and an aromatic heterocyclic group are more preferable.
- L B of Ariru group and an aromatic heterocyclic group good Mashiku alkyl group as Yogu substituent may have a substituent, Aruke - group, an alkyl group, Ariru group, an amino group, an alkoxy group , Aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbol group, acyloxy group, acylamino group, alkoxycarbolamamino group, aryloxycarbolamino group, sulfo-lumino group, sulfamoyl group, strong rubamoyl Group, alkylthio group, arylthio group, sulfol group, halogen atom, cyano group and aromatic heterocyclic group, more preferably alkyl group, aryl group, alkoxy group, aryloxy group, halogen atom, cyano group and aromatic group.
- a heterocyclic group more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an aromatic group.
- a heterocyclic group particularly preferably ⁇ alkyl group, Ariru group, an alkoxy group, an aromatic heterocyclic group.
- R B2 represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.
- the aliphatic hydrocarbon group for R B2 is a linear, branched or cyclic alkyl group (preferably an alkyl group having 120 carbon atoms, more preferably 112 carbon atoms, and particularly preferably 18 carbon atoms, , Methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, nxadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.) , A alkenyl group (preferably a alkenyl group having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, for example, bur, allyl, 2 butyr, 3 Alkenyl group (preferably an alkyl group having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as propargyl).
- the aryl group of R B2 is a single ring or a condensed ring, preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms.
- the heterocyclic group of R B2 is a monocyclic ring or a condensed ring, preferably a heterocyclic group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 2 to 10 carbon atoms.
- An aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom is preferred.
- heterocyclic group examples include, for example, pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole.
- Indazole purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, atridine, phenanthorin, phenazine, tetrazole, benzimidazole Benzoxazonole, benzothiazonole, benzotriazonole, tetrazaindene, carbazole, azepine and the like, preferably, furan, thio Phen, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxaline, and quinazoline are more preferable, and furan, thiophene, pyridine, and quino
- substituent group aliphatic hydrocarbon group represented by R B2 Ariru group and heterocyclic group have substituents! /, As Yogu substituent also is represented by L B are the same as those mentioned above, and preferred substituents are also the same.
- R B2 is preferably an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, and more preferably Or an aliphatic hydrocarbon group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms) or an aryl group, and more preferably an aliphatic carbon group.
- a hydrogen group preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and still more preferably 2 to 10 carbon atoms).
- Z B2 represents an atomic group necessary for forming an aromatic ring.
- Specific examples of the aromatic ring formed by Z B2 may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring include, for example, a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, Examples include pyrrole ring, furan ring, thiophene ring, selenophene ring, terorophene ring, imidazole ring, thiazole ring, selenazole ring, tellurazole ring, thiadiazole ring, oxadiazole ring, and pyrazole ring, preferably benzene.
- Ring, pyridine ring, pyrazine ring, pyrimidine ring and pyridazine ring more preferably benzene ring, pyridine ring and pyrazine ring, further preferably benzene ring and pyridine ring, particularly preferably pyridine ring.
- the aromatic ring formed by Z B2 may further have a substituent which may form a condensed ring with another ring.
- the substituent is exemplified ones the same way as a substituent group represented by L B, preferably an alkyl group, Aruke - group, an alkyl group, Ariru group, an amino group, an alkoxy group, Ariruokishi Group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbolamamino group, aryloxycarbolamamino group, sulfo-lumino group, sulfamoyl group, carbamoyl group Alkylthio group, arylthio group, sulfol group, halogen atom, cyano group, and heterocyclic group, more preferably alkyl group, aryl group, alkoxy group, aryloxy group, halogen atom
- n B2 is an integer of 1 to 4, preferably 2 to 3.
- R m , R B72 and R B73 are the same as R B2 in the general formula (B), respectively, and the preferred ranges are also the same.
- Z B71, Z B72 and Zeta Beta73 are similar to Zeta B2 in the general formula (beta) respectively, and the preferred ranges are also the same.
- L B71, L B72 and L B73 each represent a linking group, those divalent examples of L B can be mentioned in the general formula (B), preferably a single bond, a divalent aromatic hydrocarbon ring Group, a divalent aromatic heterocyclic group, and a linking group having a combination force thereof, more preferably a single bond.
- L m, L B72 and L B73 are the same as those exemplified as the substituents of the group as the Yogu substituent group which may have a substituent represented by L B in the foregoing formula (B), also The same applies to preferred substituents.
- Y represents a nitrogen atom, a 1, 3, 5-benzenetriyl group or a 2, 4, 6-triazine triyl group.
- the 1, 3, 5-benzenetriyl group may have a substituent at the 2, 4, 6-position.
- substituent include an alkyl group, an aromatic hydrocarbon ring group, and a halogen atom.
- an inorganic compound as a constituent component of the electron injection layer It is preferable to use an insulator or a semiconductor. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
- Electron injection layer force S It is preferable that it is composed of these alkali metal chalcogenides and the like because the electron injection property can be further improved.
- preferred alkali metal chalcogenides include, for example, Li 0, K 0, Na S, Na Se and Na 2 O.
- potash earth metal chalcogenides examples include CaO, BaO, SrO, BeO, BaS, and CaSe.
- preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KC1, and NaCl.
- Preferred alkaline earth metal halides include fluorides such as CaF, BaF, SrF, MgF and BeF.
- Semiconductors include Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta,
- the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film can be formed, and pixel defects such as dark spots can be reduced. In addition, as such an inorganic compound,
- alkali metal chalcogenides alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
- the electron injection layer in the present invention preferably contains the aforementioned reducing dopant.
- the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
- the anode material used in the present invention include indium tin oxide alloy (ITO), acid tin (NESA), gold, silver, platinum, copper, and the like.
- the cathode can be an electron injection layer or a light emitting layer. For the purpose of injecting electrons into the optical layer, a material having a small work function is preferable.
- the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium indium alloy, magnesium aluminum alloy, aluminum lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
- the method for forming each layer of the organic EL device of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
- the organic thin film layer containing a compound represented by any of the general formulas (1) to (3) used in the organic EL device of the present invention is formed by vacuum deposition, molecular beam deposition (MBE) or A solution dissolved in a solvent can be formed by a known method such as a coating method such as a dating method, a spin coating method, a casting method, a bar coating method, or a roll coating method.
- each organic layer of the organic EL device of the present invention is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are generated. Usually, the range of several nm to 1 ⁇ m is preferable because of worsening.
- the compound was subjected to sublimation purification at 190 ° C.
- the purity obtained by sublimation purification was 99.8%.
- the compound was subjected to sublimation purification at 230 ° C.
- the purity of Compound 2 obtained by sublimation purification was 99.7%.
- the compound was purified by sublimation at 260 ° C.
- the purity obtained by sublimation purification was 99.4%.
- the compound was subjected to sublimation purification at 210 ° C.
- the purity obtained by sublimation purification was 99.4%.
- the compound was subjected to sublimation purification at 210 ° C.
- the purity of Compound E3 obtained by sublimation purification was 99.5%.
- the compound was purified by sublimation at 200 ° C.
- the purity of compound D3 obtained by sublimation purification was 99.7%.
- the compound was purified by sublimation at 350 ° C.
- the purity of Compound E22 obtained by sublimation purification was 99.3%.
- the compound was purified by sublimation at 330 ° C.
- the purity of Compound D22 obtained by sublimation purification was 99.5%.
- the compound was purified by sublimation at 200 ° C.
- the purity of compound G15 obtained by sublimation purification was 99.2%.
- the compound was subjected to sublimation purification at 320 ° C.
- the purity of compound H2 obtained by sublimation purification was 99.0%.
- the compound was subjected to sublimation purification at 315 ° C.
- the purity of the compound H 1 obtained by sublimation purification was 99.2%.
- a glass substrate with a transparent electrode having a thickness of 25 mm X 75 mm X 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning 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 film thickness is lOOnm so as to cover the transparent electrode on the surface where the transparent electrode line is formed. (See the structural formula below).
- the HTM film functions as a hole injecting and transporting layer. Further, following the formation of the hole injecting and transporting layer, D1 and a complex P having the following structural formula as a host compound were co-deposited by resistance heating at a thickness of 30 nm on this film.
- the concentration of complex P was 7wt%.
- This host compound: D1 film functions as a light emitting layer.
- the following material ETM1 was deposited to a thickness of 25 nm, and the following material ETM2 was deposited to a thickness of 5 nm on the ETM1.
- the ETM1 layer and the ETM2 layer function as an electron transport layer and an electron injection layer.
- LiF was used as an electron injecting electrode (cathode) to form a film thickness of 0.1 nm at a film forming speed of lAZmin.
- Metal A1 was vapor-deposited on this LiF layer, and a metal cathode was formed to a thickness of 150 nm to form an organic EL light emitting device.
- An organic EL device was produced in the same manner as in Example 1, except that each compound described in the host compound column of Table 1 was used instead of the host compound D1.
- the luminous efficiency was measured in the same manner as in Example 1, and the results are shown in Table 1.
- Example 1 instead of the host compound D1, organic compounds were similarly prepared except that the following comparative compounds 1 to 3 described in International Publication WO2004Z096945, JP-A-5-109485 and JP-A-2004-214050 were used. An EL device was produced. For each organic EL element obtained, the luminous efficiency was measured in the same manner as in Example 1, and the results are shown in Table 1.
- the organic EL device using the compound according to the present invention for the light emitting layer had high luminous efficiency. From these results, the compound in the present invention is effective as an organic EL application.
- an organic electoluminescence device material made of a compound represented by any one of the general formulas (1) to (14) of the present invention increases the luminous efficiency.
- an organic electoluminescence device having no pixel defects, excellent heat resistance, and a long lifetime can be obtained.
- the organic electoluminescence element of the present invention is used for various electronic devices. It is extremely useful as a light source.
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Abstract
Description
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JP5290581B2 (ja) | 2013-09-18 |
EP1962354A4 (en) | 2010-02-24 |
CN101331626B (zh) | 2011-08-17 |
EP1962354A1 (en) | 2008-08-27 |
TWI420963B (zh) | 2013-12-21 |
CN101331626A (zh) | 2008-12-24 |
TW200730027A (en) | 2007-08-01 |
KR20080080306A (ko) | 2008-09-03 |
JPWO2007069569A1 (ja) | 2009-05-21 |
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