WO2010098246A1 - 有機電界発光素子 - Google Patents
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- WO2010098246A1 WO2010098246A1 PCT/JP2010/052411 JP2010052411W WO2010098246A1 WO 2010098246 A1 WO2010098246 A1 WO 2010098246A1 JP 2010052411 W JP2010052411 W JP 2010052411W WO 2010098246 A1 WO2010098246 A1 WO 2010098246A1
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Definitions
- the present invention relates to an organic electroluminescent device exhibiting a high luminance rate by using a phosphorescent dopant material and a host material in combination.
- An organic electroluminescence element (organic EL element) is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. When an electric field is applied between the electrodes, electrons are injected from the cathode and holes are injected from the anode, and these recombine in the light emitting layer to generate excitons, whose energy level returns from the conduction band to the valence band. It uses the phenomenon of emitting light as energy.
- Organic EL elements are classified into fluorescent organic EL elements and phosphorescent organic EL elements depending on the light emission mechanism.
- the light emitting layer of the phosphorescent organic EL device is generally composed of a phosphorescent dopant material and a host material. If such a phosphorescent dopant material is used for light emission, a triplet state exciton having a generation probability of 75% can be used. Therefore, a fluorescent organic EL element using a singlet exciton having a generation probability of 25% It can have higher luminous efficiency.
- low molecular weight host materials have been actively researched and developed as host materials used in the light emitting layer.
- low-molecular compounds used as host materials are easily purified by purification techniques such as sublimation, column chromatography, and recrystallization.
- the high-purity low molecular host material reduces the number of impurity-derived energy trap sites and minimizes thermal deactivation of electrons, holes, or excitons injected from the electrode, resulting in high performance.
- the low molecular weight host material has characteristics that are generally found in low molecular weight compounds, such that the higher the purity, the higher the crystallinity.
- the light emitting layer using a high-purity low-molecular host material is partially crystallized by the weak heat generated during device operation, and the amorphous characteristics of the light emitting layer are impaired. is there.
- This characteristic has a more significant effect when the light emitting layer is formed by wet process. This is presumably because in wet process film formation, after a solution of a low molecular weight host compound is applied, a high concentration solution is temporarily formed during the drying step of evaporating the solvent, and crystallization is likely to occur. This is a major problem that a low molecular weight host material exhibiting high performance in the vapor deposition process cannot be applied to the wet process.
- a method for ensuring the amorphous stability of the light-emitting layer by mixing at least one other low-molecular host material with a low-molecular host material serving as a base is disclosed.
- a method of mixing amorphous polymer materials (Patent Document 1) and a method of mixing charge injection and charge transport auxiliary materials (Patent Documents 2 to 6) are disclosed.
- Japanese Patent Laid-Open No. 2002-203684 Japanese Patent Laid-Open No. 11-354279 Japanese Patent Laid-Open No. 2003-068466 JP 2004-335204 A JP 2006-135295 A JP 2006-148045 A
- IP ionization potential
- EA electron affinity
- T1 triplet excitation energy level
- the object of the present invention is to crystallize a material by weak heat generated during operation of a phosphorescent organic EL device using a low molecular weight host material while maintaining an electron / hole injection balance and an efficient phosphorescent light emitting mechanism. It is an object of the present invention to provide a low-molecular host material capable of suppressing crystallization and to provide a highly reliable organic electroluminescent element in the case of forming a wet process by suppressing the above.
- the present invention is an organic electroluminescent device having a light emitting layer formed by a wet process between an anode and a cathode, wherein the light emitting layer contains a phosphorescent dopant material and a host material having a molecular weight of 10,000 or less, and the host material Comprises a second host material different from the first host material and the first host material has a weight ratio of 90:10 to 10:90 of the first host material and the second host material,
- IP ionization potential
- EA electron affinity
- T1 value is The present invention relates to an organic electroluminescent element characterized by being 0.1 eV or less.
- Preferred examples of the first host material or the second host material include heterocyclic compounds selected from the group consisting of indolocarbazole derivatives and triazine derivatives.
- ring A represents an aromatic ring represented by formula (1a) which is condensed with an adjacent ring at an arbitrary position
- ring B is represented by formula (1b) which is condensed with an adjacent ring at an arbitrary position.
- R in the formulas (1) and (1a) is independently hydrogen or a monovalent substituent, and adjacent substituents may be combined to form a ring.
- L 1 in the formula (1b) independently represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
- L represents an n-valent aromatic hydrocarbon group or aromatic heterocyclic group, and n is 1 to 4.
- n is 2 or more, the condensed heterocycles containing rings A and B may be the same or different.
- first host material or the second host material is preferably a heterocyclic compound represented by the following formula (2) or (3).
- ring A, ring B, and R is synonymous with Formula (1)
- X is each independently C-H, N, either C-L 2.
- L 2 independently represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
- ring A, ring B and R are the same as in formula (1), and the condensed heterocycles containing rings A and B may be the same or different.
- Ar independently represents a phenylene group or a divalent aromatic heterocyclic group. m is 1-5.
- the present invention also relates to an organic electroluminescent device in which the first host material and the second host material are two kinds of heterocyclic compounds selected from the heterocyclic compounds represented by the formula (2) or (3). .
- the weight ratio of the first host material and the second host material is preferably 75:25 to 25:75.
- the organic EL device of the present invention has an anode (also referred to as an anode layer) and a cathode (also referred to as a cathode layer), and an organic layer sandwiched between the anode and the cathode. At least one of the organic layers is a light emitting layer.
- the layer structure of the element is not particularly limited, and a typical element structure is as shown in FIG.
- the organic EL device of the present invention includes the substrate 1, the anode 2, the light emitting layer 5, and the cathode 7 as essential layers, but the device performance can be improved by providing other layers as necessary.
- the substrate 1 is laminated in the order of the substrate 1, the anode 2, the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, the electron transport layer 6 and the cathode 7, but is indispensable if necessary. Layers other than the layers may be omitted, and layers other than those described above may be added or replaced as necessary.
- the light emitting layer of the organic EL device of the present invention contains a phosphorescent dopant material and a host material having a molecular weight of 10,000 or less, and the host material is composed of a first host material and a second host material.
- the second host material is at least one host material different from the first host material.
- the host material selected first is referred to as a first host material
- the other host material is referred to as a second host material.
- the second host material may contain two or more compounds, but is preferably one. When two or more kinds of compounds are included, the IP, EA, and T1 values of the compounds satisfy the following requirements with respect to the first host material.
- the second host material is effective for suppressing crystallization of the first host material. Since the IP, EA, and T1 values of the host material have already been adjusted to appropriate values in the high brightness factor element, the second host material is mixed from the viewpoint of maintaining the high brightness rate.
- the IP, EA and T1 values of the second host material are preferably the same values as the IP, EA and T1 values of the first host material, but these values are unique values calculated from the molecular structure. In fact, there is no compound that has the same three values. However, if the difference between the IP, EA, and T1 values of the first host material and the second host material is 0.10 eV or less, crystallization of the light-emitting layer is suppressed while maintaining the device characteristics with high luminance rate. In addition, it has been found that good light emission characteristics can be maintained for a long time.
- the IP and EA values of the first host material and the second host material are calculated as values inherent to the compound based on the molecular structure of the compound serving as the host material, and sequentially changing the signs of the HOMO energy and the LUMO energy. be able to.
- This relationship is defined as Koopmans' theorem under the Hartree-Fock approximation and as the Yanak's theorem in density functional theory.
- the values of HOMO energy and LUMO energy (eV unit converted value) can be calculated by structure optimization calculation using the density functional theory (DFT) method using the molecular orbital method program Gaussian03rev.C02.
- DFT density functional theory
- the T1 value can be calculated as the lowest value of the excitation triplet excitation energy calculated as a value unique to the compound based on the molecular structure of the compound serving as the host material.
- the excitation triplet excitation energy value is based on the optimized structure after the structure optimization using the density functional theory (DFT) calculation using, for example, the molecular orbital method program Gaussian03rev.C02. And time-dependent density functional theory (TD-DFT) calculation.
- DFT density functional theory
- TD-DFT time-dependent density functional theory
- the calculation method of the IP, EA, and T1 values is not particularly limited, but the same calculation method is used for the first host material and the second host material in order to avoid errors due to the calculation method.
- the compound serving as the first host material or the second host material is not particularly limited as long as it is applicable to the host material of the organic EL element.
- Compounds useful as host materials are known from many patent documents and the like, and are selected and used.
- a compound suitable as the first host material or the second host material is a charge transporting heterocyclic compound having a carbazole group, an indolocarbazole group, an oxadiazole group, a triazine group, or the like.
- the heterocyclic compound chosen from the group which consists of an indolocarbazole derivative and a triazine derivative is mentioned.
- the indolocarbazole derivative is a compound having an indolocarbazole skeleton and can have one or more substituents.
- a preferable substituent is a substituent having a triazine ring.
- the triazine derivative is a compound having a triazine ring and can have one or more substituents. Note that an indolocarbazole derivative having a triazine ring as a substituent is also a triazine derivative.
- a compound represented by the above formula (1) can be preferably used, and more preferably a compound represented by the formula (2) or (3). It is.
- Ring A is an aromatic ring represented by Formula (1a)
- Ring B is a heterocycle represented by Formula (1b).
- the heterocyclic ring represented by ring B is 2,3- And 4,5-positions and vice versa, and the 1,2-, 2,3- and 3,4-positions of the adjacent carbazole ring.
- isomers in the condensed heterocyclic ring including ring A and ring B in 1), (2) or (3).
- This fused heterocycle is an indolocarbazole ring.
- L represents an n-valent aromatic hydrocarbon group or an aromatic heterocyclic group, preferably an n-valent aromatic hydrocarbon group having 6 to 100 carbon atoms or an n-valent carbon group having 3 to 100 carbon atoms. And an n-valent aromatic hydrocarbon group having 6 to 36 carbon atoms or an n-valent aromatic heterocyclic group having 3 to 35 carbon atoms is more preferable.
- aromatic hydrocarbon groups or aromatic heterocyclic groups may have a substituent, and when they have two or more substituents, they may be the same or different. The calculation of the carbon number includes the carbon number of these substituents.
- Preferred aromatic hydrocarbon groups or aromatic heterocyclic groups include benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, tridene, fluoranthene, acephenanthrylene, and acanthrylene.
- More preferred is a group formed by removing n hydrogens from benzene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, carbazole or an aromatic compound in which a plurality of these aromatic rings are connected.
- the aromatic ring is a group derived from a linked aromatic compound, the number to be linked is preferably 2 to 10, more preferably 2 to 5, and the linked aromatic rings may be the same. It may be different.
- the bond position of the aromatic compound in which a plurality of N and aromatic rings of the indolocarbazole ring including rings A and B are connected is not limited, and even in the terminal portion of the connected aromatic ring, the central portion The ring may be Moreover, when an aromatic heterocyclic ring is contained in the connected aromatic ring, it includes in an aromatic heterocyclic group.
- the aromatic ring is a generic term for an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
- Specific examples of the group formed by connecting a plurality of the aromatic rings include, for example, biphenyl, terphenyl, bipyridine, bipyrimidine, vitriazine, terpyridine, bistriazylbenzene, dicarbazolylbenzene, carbazolylbiphenyl, dicarbazolylbiphenyl.
- Gerare more preferably benzene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, aromatic ring selected from carbazole groups resulting by removing n hydrogen from an aromatic compound linked.
- the total number of substituents is 1 to 10, preferably 1 to 6, and more preferably 1 to 4.
- the group which arises from the aromatic compound with which multiple aromatic rings were connected can also have a substituent.
- Preferred substituents are alkyl groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, alkyl-substituted amino groups having 1 to 20 carbon atoms, and acyls having 2 to 20 carbon atoms.
- n 1 to 4, preferably 1 or 2.
- the substituent in the case where L 1 has a substituent is the same as the substituent described for L in the formula (1).
- R is independently hydrogen or a monovalent substituent, but in the case of a monovalent substituent, an aromatic hydrocarbon group having 6 to 26 carbon atoms, 3 carbon atoms
- it is an aromatic hydrocarbon group having 6 to 26 carbon atoms, an aromatic heterocyclic group having 3 to 25 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or 12 to 24 carbon atoms.
- phenyl group pyridyl group, pyrimidyl group, triazyl group, indolyl group, carbazolyl group, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, Examples thereof include t-butyl group, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, diphenylamino group and the like.
- R When a plurality of R are present, they may be the same or different.
- ring A, ring B and R are the same as in formula (1).
- X independently represents N, C—H or C—L 2 , preferably N is 1 to 3, more preferably N is 2 to 3, and still more preferably N is 3.
- L 2 independently represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
- L 2 is an aromatic hydrocarbon group or an aromatic heterocyclic group having a substituent, it is the same as the substituent described for the substituent of L in formula (1).
- Ar independently represents a phenylene group or a divalent aromatic heterocyclic group, and is preferably a group obtained by removing two hydrogens from benzene, pyridine, pyrimidine, triazine, indole, and carbazole. .
- Ar has a substituent, it is the same as the case where R described for R in the formulas (1) and (1a) is a monovalent substituent.
- m represents the number of Ar repeats, and m is 1 to 5, preferably 1 to 3. When m is 2 or more, Ar may be the same or different.
- a compound suitable as the first host material or the second host material is, for example, 4,4′-N, N′-dicarbazole biphenyl (CBP) other than the formula (1), (2) or (3). ), 3- (4′-tert-butylphenyl) -4-phenyl-5- (4′-biphenyl) -1,2,4-triazole (TAZ).
- CBP N′-dicarbazole biphenyl
- TEZ 3-
- the first host material is first selected from the compounds that can be used as the host material as described above, and then the compound that becomes the second host material is selected.
- the IP value of the first host material is IP (1)
- the EA value is EA (1)
- the T1 value is T1 (1)
- the IP value of the second host material is IP (2)
- the EA value is EA ( 2) If the T1 value is T1 (2), IP (1) -IP (2), EA (1) -EA (2) and T1 (1) -T1 (2) are all ⁇ 0. It is selected to be within the range of 10 eV.
- the compound serving as the first host material and the compound serving as the second host material are preferably compounds having similar basic skeletons.
- the first host material and the second host material preferably use two kinds of compounds represented by the formula (1), and use two kinds of compounds represented by the formula (2) or (3) More preferably.
- the light emitting layer of the organic EL device of the present invention includes a host material and a phosphorescent dopant material, and the host material includes a first host material and a second host material.
- the use ratio (weight ratio) of the first host material and the second host material is 90:10 to 10:90, preferably 75:25 to 25:75, more preferably 2: 1 to 1: 2. It is.
- the ratio of the host material contained in the light emitting layer is not particularly limited, but is preferably in the range of 50 to 99% by weight.
- the phosphorescent dopant material is not limited in the emission color and molecular structure, but preferably includes complexes having a noble metal element such as iridium, platinum, ruthenium or the like as a central metal. Further, the ratio of the phosphorescent dopant material contained in the light emitting layer is not particularly limited, but is preferably in the range of 1 to 50% by weight, preferably 5 to 30% by weight.
- the phosphorescent dopant material is preferably a phosphorescent dopant having a maximum emission wavelength of 580 nm or less.
- film formation method by the wet process of the light emitting layer there is no particular limitation on the film formation method by the wet process of the light emitting layer, but film formation by a wet process such as a spin coating method, a spray method, a dip method, or a doctor blade method may be selected.
- a wet process such as a spin coating method, a spray method, a dip method, or a doctor blade method.
- the wet process is a method in which a coating liquid is prepared by dissolving an organic EL element material such as a host material in a solvent, and this is applied to a substrate or an organic layer on the substrate and dried.
- the preparation method of the coating liquid can be prepared, for example, by mixing and stirring an organic EL element material such as a host material and a solvent.
- an organic EL element material such as a host material
- a solvent such as a solvent
- the concentration of the coating liquid is not particularly limited, but is preferably 0.01 to 50 wt%, more preferably 0.1 to 10 wt%.
- the film forming method using the above coating liquid is not particularly limited, and examples thereof include a spin coating method, a slit coating method, a capillary coating method, a spray method, an ink jet method, a dip method, and a doctor blade method.
- a drying method For example, the method of heating a board
- the drying temperature varies depending on the solvent used, but is preferably 0 to 200 ° C, more preferably 50 to 150 ° C.
- the solvent used for the coating liquid is not particularly limited as long as the mixture of the first host material, the second host material, and the dopant material, which are constituent materials of the light emitting layer, can be dissolved so that no solid matter remains. Two or more solvents may be mixed and used.
- the melting point is preferably 0 ° C. or lower and the boiling point is 30 ° C. or higher.
- the substrate 1 is not particularly limited as long as it is a substrate used in a general organic electroluminescence device, but is an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness, It is preferable to use a glass substrate.
- the anode 2 is not particularly limited as long as it is a material used in a general organic electroluminescence device, and is preferably a metal or metal oxide that is transparent and excellent in electrical conductivity.
- ITO indium tin oxide
- IZO indium zinc oxide
- SnO 2 tin oxide
- ZnO zinc oxide
- the hole injection layer 3 is formed by forming a HIL substance into a thin film having a thickness of 5 to 500 nm on the upper part of the anode.
- the HIL substance is not particularly limited as long as it is a material used in a general organic electroluminescence device.
- copper phthalocyanine (CuPc) or poly (3,4-ethylenedioxy) thiophene / polystyrene sulfonic acid (PEDOT / PSS) ) Etc. can be used.
- the thin film formation method there are no particular restrictions on the thin film formation method, and not only the deposition process represented by the vacuum deposition method, but also the wet process such as the spin coating method, slit coating method, capillary coating method, spray method, ink jet method, dipping method, doctor blade method, etc.
- a film-forming method can be used.
- the hole transport layer 4 is formed by forming an HTL material into a thin film having a thickness of 5 to 500 nm on the hole injection layer.
- the HTL material is not particularly limited as long as it is a material used in a general organic electroluminescence device.
- N, N'-di (naphthalen-1-yl) -N, N' -diphenyl (1,1'-biphenyl) -4,4'-diamine ( ⁇ -NPD) can be used.
- a polymer material such as polyvinyl carbazole (PVK) can also be used.
- PVK polyvinyl carbazole
- the thin film formation method there are no particular restrictions on the thin film formation method, and not only the deposition process represented by the vacuum deposition method, but also the wet process such as the spin coating method, slit coating method, capillary coating method, spray method, ink jet method, dipping method, doctor blade method, etc.
- a film-forming method can be used.
- the electron transport layer 6 is formed by forming an ETL material in the form of a thin film having a thickness of 5 to 500 nm on the light emitting layer.
- the ETL substance is not particularly limited as long as it is a material used in a general organic electroluminescence device.
- the thin film formation method there are no particular restrictions on the thin film formation method, and not only the deposition process represented by the vacuum deposition method, but also the wet process such as the spin coating method, slit coating method, capillary coating method, spray method, ink jet method, dipping method, doctor blade method, etc.
- a film-forming method can be used.
- the cathode 7 is not particularly limited as long as it is a material used in a general organic electroluminescence device, and a metal material excellent in electrical conductivity is preferable.
- metals such as Al, Cs, Er, alloys such as MgAg, AlLi, AlLi, AlMg, CsTe, or Ca / Al, MgAl, Li / Al, Cs / Al, Cs2O / Al, LiF / Al, ErF3 /
- a laminated structure such as Al can be used.
- Synthesis example 1 Synthesis of Compound 2-9 Into a degassed nitrogen-substituted 1 L four-necked flask, 28.53 g (111.4 mmol) of indolo [2,3-a] carbazole, 21.56 g (156.02 mmol) of potassium carbonate, copper powder 35 .41 g (557.21 mmol), 1-bromo-3,5-di-t-butylbenzene 30.00 g (111.4 mmol) and tetraethylene glycol dimethyl ether 450 g were added, and the mixture was stirred at an internal temperature of 205 ° C. for 24 hours.
- the reaction mixture was dropped into 1000 g of distilled water that was vigorously stirred, and the precipitated solid was collected by filtration. This solid content was washed with methanol, and then dried under reduced pressure at 80 ° C. for a whole day and night to obtain 6.29 g of a crude product. This crude product was recrystallized and purified to obtain 3.36 g of white crystals. When the FD-MS spectrum of this white crystal was measured, a peak of 675 (M +, base) was observed, and it was confirmed that this white crystal was compound 2-9.
- Synthesis example 2 Synthesis of Compound 2-10 Into a 500 mL three-necked flask purged with degassed nitrogen, 9.84 g (38.4 mmol) of indolo [2,3-a] carbazole, 15.94 g (115.33 mmol) of potassium carbonate, copper powder 12 .22 g (192.22 mmol), 4-tert-butyliodobenzene 10.00 g (38.4 mmol) and 1,3-dimethyl-2-imidazolidinone 150 g were added, and the mixture was stirred at an internal temperature of 205 ° C. for 20 hours.
- the reaction mixture was dropped into 260 g of distilled water that was vigorously stirred, and the precipitated solid was collected by filtration. This solid content was reslurry washed with methanol at 50 ° C. for 3 hours, and then dried under reduced pressure at 80 ° C. for 24 hours to obtain 8.39 g of a crude product. This crude product was recrystallized and purified with dichloromethane to obtain 3.31 g of slightly yellow crystals. In the FD-MS spectrum of the slightly yellow crystals, a peak of 620 (MH +, base) was observed, confirming that the slightly yellow crystals were compound 2-10.
- Synthesis example 3 Synthesis of Compound 3-4 Into a degassed nitrogen-substituted 1 L four-necked flask, 45.0 g (0.176 mol) of indolo [2,3-a] carbazole, 72.9 g (0.527 mol) of potassium carbonate, copper powder 55 9.9 g (0.879 mol), 1,3-diiodobenzene 29.0 g (0.088 mol), and tetraethylene glycol dimethyl ether 638 g were added and stirred at an internal temperature of 205 ° C. for 18 hours. After cooling to room temperature, the solid content was filtered off using a filter aid.
- the obtained filtrate was transferred to a separatory funnel, 1400 g of 10 wt% hydrochloric acid was added, and the mixture was extracted with 2100 g of ethyl acetate.
- the ethyl acetate layer was washed successively with distilled water and saturated brine, and the magnesium sulfate dried and absorbed with magnesium sulfate was removed by suction filtration, and the solvent was evaporated under reduced pressure.
- the residue was subjected to dichloromethane reslurry and toluene reslurry in order, and dried at 80 ° C. under reduced pressure to obtain 29.08 g of a white solid.
- the white solid had an FD-MS spectrum of 587 (MH +, base).
- Synthesis example 5 Synthesis of Compound 3-9
- 36.96 g (0.112 mol) of 1,3-diiodobenzene, 45.00 g (0.224 mol) of 3-bromophenylboronic acid, tetrakis (Triphenylphosphine) palladium (0) 4.27 g (3.7 mmol), ethanol 225 ml, toluene 603 ml were added and stirred at room temperature.
- 142.2 g (1.342 mol) of sodium carbonate and 297 g of distilled water were charged, and stirred at an internal temperature of 75 ° C. for 19 hours.
- the obtained filtrate was transferred to a separatory funnel, 1000 ml of 10 wt% hydrochloric acid was added, and the mixture was extracted with 700 g of ethyl acetate.
- the ethyl acetate layer was washed sequentially with saturated brine, dried over magnesium sulfate, and the magnesium sulfate absorbed was removed by suction filtration, and the solvent was evaporated under reduced pressure.
- the residue was washed with dichloromethane reslurry and dried at 80 ° C. under reduced pressure to obtain 13.24 g of a white solid.
- the white solid had an FD-MS spectrum of 738 (M +, base).
- Synthesis example 7 Synthesis of Compound A Compound A was synthesized in the same manner as described in JP-A-2005-239703. When an FD-MS spectrum was measured, a peak of 524 (M +, base) was observed, confirming that it was Compound A.
- Synthesis example 8 Synthesis of Compound B Compound B was synthesized according to the method described in Example 4 of WO08-056746.
- IP, EA and T1 value was calculated.
- the IP, EA, and T1 values were calculated by structure optimization calculation using the density functional theory (DFT) method using the molecular orbital method program Gaussian03rev.C02.
- the IP value and the EA value were values obtained by changing the sign of the HOMO energy and the LUMO energy calculated by performing the structural optimization calculation at the B3LYP / 6-31G * level (eV unit converted value).
- Example 1 (comparison) In FIG. 1, an organic EL device having a configuration in which the hole transport layer was omitted and an electron injection layer was added was produced. A 20 wt% ethanol solution of PEDOT / PSS (Baytron P CH8000) as a hole injection layer was formed on a glass substrate on which an anode made of ITO having a film thickness of 150 nm passed through UV ozone cleaning and drying processes was rotated at 3000 rpm. For 60 seconds, and dried at 200 ° C. for 60 minutes. The film thickness at this time was 25 nm.
- PEDOT / PSS Boytron P CH8000
- the host material is compound 2-1 (38.0 parts by weight)
- the phosphorescent dopant material is tris (2-phenylpyridine) iridium (Ir (ppy) 3) (2.0 parts by weight)
- dichloromethane A mixed solution of (2840 parts by weight) was spin-coated at a rotation speed of 4000 rpm for 30 seconds and dried at 120 ° C. for 30 minutes.
- the film thickness of the light emitting layer at this time was 70 nm.
- tris (8-hydroxyquinoline) aluminum (Alq3) was formed by a vacuum deposition method at a deposition rate of 0.1 nm / sec to a thickness of 35 nm.
- lithium fluoride (LiF) was formed to a thickness of 0.5 nm by vacuum deposition.
- Al aluminum
- an external power source was connected to the device, a DC voltage was applied so that a current of 100 mA / cm 2 flowed, and current efficiency (cd / A) at that time was measured. Further, as a lifetime characteristic of the element, a DC voltage was applied so that the constant current amount was 20 mA / cm 2, and the time until the initial luminance was reduced by half (luminance half-life) was measured. This was converted to an initial luminance of 1000 cd / m 2 . The current efficiency was 5.7 cd / A, and the luminance half life was 32 hr.
- Example 2 As the host material, the first host material and the second host material are used, the compound 2-1 (17.3 parts by weight) as the first host material and the compound 2-9 (20. 7 parts by weight) was used, and an organic EL device was prepared by performing the same operation as in Example 1 except that a light emitting layer having a thickness of 70 nm was obtained.
- Example 3 In Example 2, the compound 2-1 (18.0 parts by weight) as the first host material and the compound 2-10 (20.0 parts by weight) as the second host material were used, and a light emitting layer having a thickness of 70 nm was used. Except having obtained, organic EL element was produced by performing the same operation and element evaluation was performed.
- Example 4 In Example 2, the compound 2-1 (13.3 parts by weight) was used as the first host material and the compound 3-4 (24.7 parts by weight) was used as the second host material, and a light-emitting layer having a thickness of 70 nm Except having obtained, all the same operations were performed, the organic EL element was produced, and element evaluation was performed.
- Example 5 In Example 2, the compound 2-1 (12.1 parts by weight) was used as the first host material and the compound 3-9 (25.9 parts by weight) was used as the second host material, and a light-emitting layer having a thickness of 70 nm Except having obtained, all the same operations were performed, the organic EL element was produced, and element evaluation was performed.
- Example 6 In Example 2, the compound 2-1 (23.6 parts by weight) was used as the first host material and the compound 3-4 (14.4 parts by weight) was used as the second host material, and a light-emitting layer having a thickness of 70 nm Except having obtained, all the same operations were performed, the organic EL element was produced, and element evaluation was performed.
- Example 7 (comparison) In Example 2, Compound 2-1 (19.7 parts by weight) was used as the first host material and Compound A (18.3 parts by weight) was used as the second host material to obtain a light-emitting layer having a thickness of 70 nm. Except for the above, the same operation was performed to produce an organic EL device, and the device was evaluated.
- Example 8 (comparison) In Example 2, Compound 2-1 (16.7 parts by weight) was used as the first host material and Compound B (21.3 parts by weight) was used as the second host material to obtain a light-emitting layer having a thickness of 70 nm. Except for the above, the same operation was performed to produce an organic EL device, and the device was evaluated.
- Example 9 (comparison) In Example 2, Compound 2-1 (14.2 parts by weight) was used as the first host material and Compound C (23.8 parts by weight) was used as the second host material to obtain a light-emitting layer having a thickness of 70 nm. Except for the above, the same operation was performed to produce an organic EL device, and the device was evaluated.
- Example 10 (comparison) In Example 1, except that Compound 3-1 was used as a host material and a light emitting layer having a thickness of 70 nm was obtained, all the same operations were performed to produce an organic EL device, and device evaluation was performed. The current efficiency was 10.8 cd / A, and the luminance half-life was 48 hours.
- Example 11 In Example 2, a compound 3-1 (16.6 parts by weight) was used as the first host material and a compound 3-4 (21.4 parts by weight) was used as the second host material, and a light emitting layer having a thickness of 70 nm Except having obtained, all the same operations were performed, the organic EL element was produced, and element evaluation was performed.
- Example 12 In Example 2, a compound 3-1 (20.8 parts by weight) was used as the first host material and a compound 2-9 (17.2 parts by weight) was used as the second host material, and a light-emitting layer having a thickness of 70 nm Except having obtained, all the same operations were performed, the organic EL element was produced, and element evaluation was performed.
- Example 13 In Example 2, a compound 3-1 (17.4 parts by weight) was used as the first host material and a compound 3-14 (20.6 parts by weight) was used as the second host material, and a light emitting layer having a thickness of 70 nm was used. Except having obtained, all the same operations were performed, the organic EL element was produced, and element evaluation was performed.
- Example 14 (comparison) In Example 2, Compound 3-1 (14.8 parts by weight) was used as the first host material and Compound A (23.2 parts by weight) was used as the second host material to obtain a light-emitting layer having a thickness of 70 nm. Except for the above, the same operation was performed to produce an organic EL device, and the device was evaluated.
- Example 15 (Comparison) In Example 2, Compound 3-1 (20.2 parts by weight) was used as the first host material and Compound B (17.8 parts by weight) was used as the second host material to obtain a light-emitting layer having a thickness of 70 nm. Except for the above, the same operation was performed to produce an organic EL device, and the device was evaluated.
- Example 16 (Comparison) In Example 2, Compound 3-1 (17.7 parts by weight) was used as the first host material and Compound C (20.3 parts by weight) was used as the second host material to obtain a light-emitting layer having a thickness of 70 nm. Except for the above, the same operation was performed to produce an organic EL device, and the device was evaluated.
- Table 2 shows the results of Examples 1 to 6. The current efficiency and luminance half-life of each example are expressed as relative values when Example 1 is 100.
- H1 represents the first host material
- H2 represents the second host material.
- Table 3 shows the results of Example 10 to Example 16. The current efficiency and luminance half-life of each example are expressed as relative values when the value of Example 10 is 100.
- H1 represents the first host material
- H2 represents the second host material.
- a highly reliable organic electric field can be obtained by suppressing crystallization of the material due to weak heat generated during operation of the device while maintaining an electron / hole injection balance and an efficient phosphorescence emission mechanism.
- a light-emitting element can be provided.
- an organic electroluminescent device having a high luminance rate and high reliability can be provided by suppressing crystallization in the drying step.
- the organic EL device of the present invention can maintain good light emission characteristics for a long period of time.
Abstract
Description
式(1)中、環Aは隣接環と任意の位置で縮合する式(1a)で表される芳香環を表し、環Bは隣接環と任意の位置で縮合する式(1b)で表される複素環を表す。式(1)、(1a)中のRは、独立に水素又は1価の置換基であり、隣接する置換基が一体となって環を形成してもよい。式(1b)中のL1は、独立に芳香族炭化水素基又は芳香族複素環基を示す。Lは、n価の芳香族炭化水素基又は芳香族複素環基を示し、nは1~4である。nが2以上の場合は、環A、Bを含む縮合複素環は同一であっても異なっていても良い。
基板1としては、一般的な有機電界発光素子で使われる基板であれば特に制限はないが、透明性、表面の平滑性、取扱の容易性及び防水性に優れた有機基板又は透明プラスチック基板、ガラス基板を用いることが好ましい。
なお、以下の合成例1~5で使用するインドロ[2,3-a]カルバゾール、2-クロロ-4,6-ジフェニル-1,3,5-トリアジン、及び実施例1の化合物2-1については、WO08―056746号公報に記載の方法に従い合成した。また、化合物3-1については、WO07―063754号公報に記載の方法に従い合成した。
化合物2-9の合成
脱気窒素置換した1L四ッ口フラスコに、インドロ[2,3-a]カルバゾール28.53g(111.4mmol)、炭酸カリウム21.56g(156.02mmol)、銅粉末35.41g(557.21mmol)、1-ブロモ-3,5-ジ-t-ブチルベンゼン30.00g(111.4mmol)、テトラエチレングリコールジメチルエーテル450gを入れ、内温205℃で24時間攪拌した。室温まで冷却後、ろ過助剤を用いて固形分をろ別し、ろ液を減圧下濃縮した。次いで、シリカゲルカラムにて分画・精製し、白色固体7.42gを得た。この白色固体のFD-MSスペクトルは、445(MH+、base)であった。
化合物2-10の合成
脱気窒素置換した500mL三ッ口フラスコに、インドロ[2,3-a]カルバゾール9.84g(38.4mmol)、炭酸カリウム15.94g(115.33mmol)、銅粉末12.22g(192.22mmol)、4-t-ブチルヨードベンゼン10.00g(38.4mmol)、1,3-ジメチル-2-イミダゾリジノン150gを入れ、内温205℃で20時間攪拌した。室温まで冷却後、ろ過助剤を用いて固形分をろ別し、ろ液を減圧下濃縮した。ろ液を分液ロートに移し、酢酸エチル700ml、10%塩酸を加えて、0.5時間静置し、下層を廃棄した。上層を蒸留水、飽和食塩水で洗浄、硫酸マグネシウムで乾燥後、溶媒を減圧留去し、褐色固体を得た。シリカゲルカラムにて精製後、ジクロロメタン-エタノールで再結晶を行い、白色結晶6.30gを得た。この白色固体のFD-MSスペクトルは、389(MH+、base)であった。
化合物3-4の合成
脱気窒素置換した1L四ツ口フラスコに、インドロ[2,3-a]カルバゾール45.0g(0.176mol)、炭酸カリウム72.9g(0.527mol)、銅粉末55.9g(0.879mol)、1,3-ジヨードベンゼン29.0g(0.088mol)、テトラエチレングリコールジメチルエーテル638gを入れ、内温205℃で18時間攪拌した。室温まで冷却後、ろ過助剤を用いて固形分をろ別した。得られたろ液を分液ロートに移し、10重量%塩酸1400gを加えた後、酢酸エチル2100gで抽出した。酢酸エチル層を蒸留水、飽和食塩水で順に洗浄した後、硫酸マグネシウムで乾燥、吸水した硫酸マグネシウムを吸引ろ過で除去後、溶媒を減圧留去した。残渣をジクロロメタンリスラリー、トルエンリスラリーを順に行い、減圧下80℃で乾燥し、白色固体29.08gを得た。この白色固体のFD-MSスペクトルは、587(MH+、base)であった。
化合物3-9の合成
脱気窒素置換した2L四ッ口フラスコに、1,3-ジヨードベンゼン36.96g(0.112mol)、3-ブロモフェニルボロン酸45.00g(0.224mol)、テトラキス(トリフェニルホスフィン)パラジウム(0)4.27g(3.7mmol)、エタノール225ml、トルエン603mlを入れ、室温で攪拌した。この溶液に、炭酸ナトリウム142.2g(1.342mol)、蒸留水297gを装入し、内温75℃にて19時間攪拌した。室温まで冷却し、水層を抜き出した後、有機層を飽和食塩水で洗浄し、硫酸マグネシウムで乾燥、吸水した硫酸マグネシウムを吸引ろ過で除去後、溶媒を減圧留去した。シリカゲルカラムにて精製し、茶色油状物42.13gを得た。これを0.2kPaの減圧下にて蒸留精製し、留出温度220~234℃を分画し、無色油状物21.55gを得た。FD-MSスペクトルにて、386、388、390(M+、base、1:2:1強度比)のピークが観測され、1,3-ビス(3-ブロモフェニル)ベンゼンであることを確認した。
化合物3-14の合成
WO07―063754号公報記載の化合物3-1の合成方法において、フェニルボロン酸を(3,5-ジフェニル)フェニルボロン酸に変更した以外は同様にして、化合物3-14を合成した。FD-MSスペクトルを測定したところ、970(M+、base)のピークが観測され、化合物3-14であることを確認した。
化合物Aの合成
特開2005-239703号公報に記載の方法と同様にして、化合物Aを合成した。FD-MSスペクトルを測定したところ、524(M+、base)のピークが観測され、化合物Aであることを確認した。
化合物Cの合成
WO07―063754号公報記載の化合物3-1の合成方法において、フェニルボロン酸をピレンー2-イルボロン酸に変更した以外は同様にして、化合物Cを合成した。FD-MSスペクトルを測定したところ、941(M+、base)のピークが観測され、化合物Cであることを確認した。
前述の合成例で得た化合物2-9、2-10、3-4、3-9、3-14、化合物2-1、3-1、及び化合物A、B、Cについて、IP、EA及びT1値を算出した。
IP、EA、T1値は、分子軌道法プログラムGaussian03rev.C02を使用して、密度汎関数理論(DFT)法を用いた構造最適化計算により計算した。IP値、EA値は、B3LYP/6-31G*レベルの構造最適化計算を行うことにより計算されたHOMOエネルギー、LUMOエネルギーの符号をかえた値(eV単位換算値)とした。T1値は、B3LYP/6-31G*レベルの構造最適化計算を行った後、最適化された構造を基にTD-B3LYP/6-31G*レベルで励起3重項の最も低い励起エネルギーを算出した。各化合物の計算値は、表1に示した。
図1において正孔輸送層を省略し、電子注入層を追加した構成の有機EL素子を作製した。UVオゾン洗浄及び乾燥工程を経た膜厚150nmのITOからなる陽極が形成されたガラス基板上に、正孔注入層として、PEDOT・PSS(Baytron P CH8000)の20重量%エタノール溶液を、回転数3000rpmで60秒間スピンコート製膜し、200℃で60分間乾燥した。このときの膜厚は25nmであった。次に、発光層として、ホスト材料が化合物2-1(38.0重量部)、燐光ドーパント材料がトリス(2-フェニルピリジン)イリジウム(Ir(ppy)3)(2.0重量部)、ジクロロメタン(2840重量部)の混合溶液を、回転数4000rpmで30秒間スピンコート製膜し、120℃にて30分間乾燥した。このときの発光層の膜厚は70nmであった。次に、電子輸送層として、トリス(8-ヒドロキシキノリン)アルミニウム(Alq3)を真空蒸着法にて、蒸着レート0.1nm/secにて35nmの厚さで製膜した。更に電子注入層として、真空蒸着法にてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に電子注入層上に電極として、真空蒸着法にてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作製した。
ホスト材料として、第一のホスト材料と第二のホスト材料を使用し、第一のホスト材料として化合物2-1(17.3重量部)と第二のホスト材料として化合物2-9(20.7重量部)を使用し、70nm膜厚の発光層を得た以外は、実施例1と同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(18.0重量部)と第二のホスト材料が化合物2-10(20.0重量部)を使用し、70nm膜厚の発光層を得た以外は、同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(13.3重量部)と第二のホスト材料として化合物3-4(24.7重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(12.1重量部)と第二のホスト材料として化合物3-9(25.9重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(23.6重量部)と第二のホスト材料として化合物3-4(14.4重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(19.7重量部)と第二のホスト材料として化合物A(18.3重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(16.7重量部)と第二のホスト材料として化合物B(21.3重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2-1(14.2重量部)と第二のホスト材料として化合物C(23.8重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例1において、ホスト材料として化合物3-1を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。電流効率は10.8cd/A、輝度半減期は48hrであった。
実施例2において、第一のホスト材料として化合物3-1(16.6重量部)と第二のホスト材料として化合物3-4(21.4重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3-1(20.8重量部)と第二のホスト材料として化合物2-9(17.2重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3-1(17.4重量部)と第二のホスト材料として化合物3-14(20.6重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3-1(14.8重量部)と第二のホスト材料として化合物A(23.2重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3-1(20.2重量部)と第二のホスト材料として化合物B(17.8重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3-1(17.7重量部)と第二のホスト材料として化合物C(20.3重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
Claims (7)
- 陽極及び陰極の間にウェットプロセスにより製膜された発光層を有する有機電界発光素子であって、発光層がりん光ドーパント材料と分子量10,000以下のホスト材料を含有し、前記ホスト材料は第一のホスト材料と第一のホスト材料とは異なる第二のホスト材料からなり、第一のホスト材料と第二のホスト材料の重量比が90:10~10:90であり、第一のホスト材料と第二のホスト材料のイオン化ポテンシャル(IP)値の差が0.1eV以下、かつ電子親和力(EA)値の差が0.1eV以下、かつ三重項エネルギー(T1)値の差が0.1eV以下であることを特徴とする有機電界発光素子。
- 第一のホスト材料又は第二のホスト材料が、インドロカルバゾール誘導体及びトリアジン誘導体からなる群から選ばれる複素環化合物である請求項1に記載の有機電界発光素子。
- 第一のホスト材料と第二のホスト材料が、式(2)又は(3)で表される複素環化合物から選ばれる2種の複素環化合物である請求項4記載の有機電界発光素子。
- 第一のホスト材料と第二のホスト材料の重量比が75:25~25:75である請求項1に記載の有機電界発光素子。
- 陽極及び陰極の間に発光層を含む有機層を有し、発光層がりん光ドーパント材料と分子量10,000以下のホスト材料を含有する有機電界発光素子の製造方法であって、ホスト材料とりん光ドーパント材料を用意すること、ここで、ホスト材料が、第一のホスト材料と第一のホスト材料とは異なる第二のホスト材料からなり、第一のホスト材料と第二のホスト材料の重量比が90:10~10:90であり、第一のホスト材料と第二のホスト材料のイオン化ポテンシャル(IP)値の差が0.1eV以下、かつ電子親和力(EA)値の差が0.1eV以下、かつ三重項エネルギー(T1)値の差が0.1eV以下であること、ホスト材料とりん光ドーパント材料を溶媒に溶解して塗液を形成すること、この塗液を発光層に隣接する有機層上に塗布、乾燥して製膜する工程を含むことを特徴とする有機電界発光素子の製造方法。
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CN106935712A (zh) * | 2015-12-29 | 2017-07-07 | 三星显示有限公司 | 有机发光器件 |
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JPWO2017199622A1 (ja) * | 2016-05-19 | 2019-03-14 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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JP7238044B2 (ja) | 2016-05-19 | 2023-03-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
KR20190097009A (ko) | 2016-12-27 | 2019-08-20 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자용 재료 및 유기 전계 발광 소자 |
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KR20230024436A (ko) | 2016-12-27 | 2023-02-20 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자용 재료 및 유기 전계 발광 소자 |
JP2023515163A (ja) * | 2020-03-03 | 2023-04-12 | エルジー・ケム・リミテッド | 新規な化合物およびこれを利用した有機発光素子 |
JP7427318B2 (ja) | 2020-03-03 | 2024-02-05 | エルジー・ケム・リミテッド | 新規な化合物およびこれを利用した有機発光素子 |
WO2021200243A1 (ja) | 2020-03-31 | 2021-10-07 | 日鉄ケミカル&マテリアル株式会社 | 有機電界発光素子 |
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CN102326273B (zh) | 2014-03-12 |
TW201100518A (en) | 2011-01-01 |
EP2403028A4 (en) | 2013-03-20 |
US8795852B2 (en) | 2014-08-05 |
EP2403028B1 (en) | 2014-11-12 |
JP5433677B2 (ja) | 2014-03-05 |
CN102326273A (zh) | 2012-01-18 |
JPWO2010098246A1 (ja) | 2012-08-30 |
KR20110134885A (ko) | 2011-12-15 |
US20120001158A1 (en) | 2012-01-05 |
EP2403028A1 (en) | 2012-01-04 |
KR101596906B1 (ko) | 2016-03-07 |
TWI471404B (zh) | 2015-02-01 |
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