WO2018211377A1 - 電子デバイス、発光装置、電子機器、および照明装置 - Google Patents
電子デバイス、発光装置、電子機器、および照明装置 Download PDFInfo
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- WO2018211377A1 WO2018211377A1 PCT/IB2018/053276 IB2018053276W WO2018211377A1 WO 2018211377 A1 WO2018211377 A1 WO 2018211377A1 IB 2018053276 W IB2018053276 W IB 2018053276W WO 2018211377 A1 WO2018211377 A1 WO 2018211377A1
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- HDLJTTBUZXCRHT-UHFFFAOYSA-N c1ccc(C2(c3ccccc3-c3ccccc23)c(cc2)ccc2N(c2ccccc2)c2ccc(C3(c(cccc4)c4-c4c3cccc4)c3ccccc3)cc2)cc1 Chemical compound c1ccc(C2(c3ccccc3-c3ccccc23)c(cc2)ccc2N(c2ccccc2)c2ccc(C3(c(cccc4)c4-c4c3cccc4)c3ccccc3)cc2)cc1 HDLJTTBUZXCRHT-UHFFFAOYSA-N 0.000 description 1
- YEDHTLQJDBFDHL-UHFFFAOYSA-N c1ccc(C2(c3ccccc3-c3ccccc23)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2)cc1 Chemical compound c1ccc(C2(c3ccccc3-c3ccccc23)c2cc(-[n]3c4ccccc4c4c3cccc4)ccc2)cc1 YEDHTLQJDBFDHL-UHFFFAOYSA-N 0.000 description 1
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Definitions
- One embodiment of the present invention relates to a novel electronic device.
- the present invention relates to an electronic device using an organic compound having a low refractive index.
- the present invention relates to a light-emitting device, an electronic device, and a lighting device each having the electronic device.
- one embodiment of the present invention is not limited to the above technical field.
- One embodiment of the present invention relates to an object, a method, or a manufacturing method. Or this invention relates to a process, a machine, a manufacture, or a composition (composition of matter).
- one embodiment of the present invention relates to an electronic device, a semiconductor device, a light-emitting device, a display device, a lighting device, a light-emitting element, and methods for manufacturing them.
- Organic EL elements light-emitting elements
- EL electroluminescence
- the basic structure of these electronic devices is such that a semiconductor layer containing an organic compound is sandwiched between a pair of electrodes.
- Such electronic devices are lightweight, flexible, and highly designable. Since there are various advantages such as the possibility of a coating process, research and development has been actively promoted.
- the light-emitting element is a self-luminous type, when used as a display pixel, there are advantages such as high visibility and no need for a backlight, and it is suitable as a flat panel display element.
- an organic semiconductor layer in which an organic compound is thinned is mainly formed, and the organic compound and the layer structure have a great influence on the organic semiconductor element. Therefore, selection of the organic compound and the layer structure is important. Furthermore, in an electronic device that emits or absorbs light, such as an organic solar cell or an organic EL element, a structure with high light extraction efficiency and light confinement effect is important.
- Patent Document 1 the light extraction efficiency is improved by forming a concavo-convex shape in a part of an electrode or an EL layer.
- a light emitting element such as an organic EL element
- a method for improving light extraction efficiency there is a method of adjusting a refractive index between a substrate and an electrode and / or between an electrode and an EL layer.
- a layer for adjusting the refractive index is introduced into the organic EL element, there is a problem that the process becomes complicated. Therefore, development of a layer and a layer structure capable of controlling the refractive index while having the function of the EL layer is required. Also, in organic solar cells, development of layers and layer structures having a high light confinement effect is required.
- an object of one embodiment of the present invention is to provide an electronic device with high light extraction efficiency. Another object of one embodiment of the present invention is to provide an electronic device including a layer with a low refractive index. Another object of one embodiment of the present invention is to provide an electronic device with low driving voltage. Another object of one embodiment of the present invention is to provide an electronic device with reduced power consumption. Another object of one embodiment of the present invention is to provide an electronic device with high reliability. Another object of one embodiment of the present invention is to provide an electronic device with high emission efficiency. Another object of one embodiment of the present invention is to provide a novel electronic device. Another object of one embodiment of the present invention is to provide an electronic device with a high light confinement effect. Another object of one embodiment of the present invention is to provide a novel semiconductor device.
- One embodiment of the present invention includes a first layer and a second layer between a first electrode and a second electrode, and the first layer is provided between the first electrode and the second layer.
- the first layer has a first organic compound and a first substance, the refractive index of the thin film of the first organic compound is not less than 1 and not more than 1.75, and the first substance has an electron accepting property.
- the second layer is an electronic device having a function of emitting or absorbing light.
- Another embodiment of the present invention includes a first layer between the first electrode and the second electrode, and the first layer includes the first organic compound and the first substance.
- the first organic compound is an electronic device having a first skeleton and an electron-donating skeleton, and the first skeleton is a tetraarylmethane skeleton or a tetraarylsilane skeleton.
- the refractive index of the first layer is preferably 1 or more and 1.75 or less.
- the aryl groups of the tetraarylmethane skeleton and the tetraarylsilane skeleton are each preferably a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. More preferably, the aryl group is a substituted or unsubstituted phenyl group.
- an organic compound having a low refractive index and good carrier transportability can be obtained.
- the aryl group or phenyl group may be bonded to each other to form a ring.
- the electron-donating skeleton preferably includes any one of a pyrrole skeleton, an aromatic amine skeleton, an acridine skeleton, and an azepine skeleton.
- the glass transition point (Tg) of the first organic compound is preferably 100 ° C. or higher.
- the refractive index of the first layer is preferably lower than the refractive index of the second layer.
- Another embodiment of the present invention includes a first layer, a second layer, and a third layer between the first electrode and the second electrode, and the first electrode and the second layer A first layer between the layers; a second layer between the first layer and the third layer; the first layer having the first organic compound and the first substance;
- the refractive index of the thin film of the first organic compound is 1 or more and 1.75 or less, the first substance has an electron accepting property, and the third layer has a function of emitting or absorbing light,
- An electronic device in which the refractive index of the first layer is lower than the refractive index of the second layer, and the refractive index of the first layer is lower than the refractive index of the third layer.
- the first organic compound preferably has an electron donating property. With this configuration, an electronic device with favorable carrier transportability can be obtained.
- the first layer and the second layer are preferably in contact with each other, and the second layer and the third layer are more preferably in contact with each other.
- the refractive index of the first layer is preferably lower than the refractive index of the first electrode.
- the volume ratio of the first substance in the first layer is preferably 0.01 or more and 0.3 or less with respect to the first organic compound.
- the first substance is titanium oxide, vanadium oxide, tantalum oxide, molybdenum oxide, tungsten oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, or hafnium oxide. And any one of silver oxides is preferable. With this configuration, an electronic device with favorable carrier transportability can be obtained.
- the first substance is 7,7,8,8-tetracyanoquinodimethane (abbreviation: TCNQ), 7,7,8,8-tetracyano-2,3,5,6-tetrafluoro.
- TCNQ 7,7,8,8-tetracyanoquinodimethane
- F4TCNQ 7,7,8,8-tetracyano-2,3,5,6-tetrafluoro.
- F6TCNNQ 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane
- the electronic device is preferably an organic EL element or a solar battery.
- Another embodiment of the present invention is an electronic device including the light-emitting element having the above structure and at least one of a housing and a touch sensor.
- Another embodiment of the present invention is a lighting device including the electronic device having each of the above structures and at least one of a housing, a connection terminal, and a protective cover.
- One embodiment of the present invention includes not only a light-emitting device including an electronic device but also an electronic device including the light-emitting device. Therefore, a light-emitting device in this specification refers to an image display device or a light source (including a lighting device).
- a display module in which a connector such as an FPC (Flexible Printed Circuit) or TCP (Tape Carrier Package) is attached to the light emitting element a display module in which a printed wiring board is provided at the end of TCP, or COG (Chip On A display module in which an IC (integrated circuit) is directly mounted by a glass method is also an embodiment of the present invention.
- an electronic device with high light extraction efficiency can be provided.
- an electronic device including a layer having a low refractive index can be provided.
- an electronic device with low driving voltage can be provided.
- an electronic device with reduced power consumption can be provided.
- a highly reliable electronic device can be provided.
- an electronic device with high emission efficiency can be provided.
- a novel electronic device can be provided.
- an electronic device with a high light confinement effect can be provided.
- a novel semiconductor device can be provided.
- FIG. 6 is a schematic cross-sectional view of an electronic device of one embodiment of the present invention.
- 4A and 4B are a cross-sectional schematic diagram and an optical path length of a light-emitting element of one embodiment of the present invention.
- FIGS. 3A and 3B are a schematic cross-sectional view of a light-emitting element of one embodiment of the present invention and a diagram illustrating a correlation between energy levels of a light-emitting layer.
- FIGS. FIGS. 3A and 3B are a schematic cross-sectional view of a light-emitting element of one embodiment of the present invention and a diagram illustrating a correlation between energy levels of a light-emitting layer.
- FIG. 10 illustrates a lighting device according to one embodiment of the present invention.
- FIG. 10 illustrates a lighting device according to one embodiment of the present invention.
- the figure explaining the refractive index based on an Example. 6A and 6B illustrate current efficiency-luminance characteristics of a light-emitting element according to an example.
- 6A and 6B illustrate current density-voltage characteristics of a light-emitting element according to an example.
- 6A and 6B illustrate an external quantum efficiency-luminance characteristic of a light-emitting element according to an example.
- 6A and 6B illustrate current efficiency-luminance characteristics of a light-emitting element according to an example.
- 6A and 6B illustrate current density-voltage characteristics of a light-emitting element according to an example.
- 6A and 6B illustrate an external quantum efficiency-luminance characteristic of a light-emitting element according to an example.
- the figure explaining the refractive index based on an Example. 6A and 6B illustrate current efficiency-luminance characteristics of a light-emitting element according to an example. 6A and 6B illustrate current density-voltage characteristics of a light-emitting element according to an example.
- 6A and 6B illustrate an external quantum efficiency-luminance characteristic of a light-emitting element according to an example.
- the ordinal numbers attached as the first and second are used for convenience, and may not indicate the process order or the stacking order. Therefore, for example, the description can be made by appropriately replacing “first” with “second” or “third”.
- the ordinal numbers described in this specification and the like may not match the ordinal numbers used to specify one embodiment of the present invention.
- film and “layer” can be interchanged.
- conductive layer may be changed to the term “conductive film”.
- insulating film may be changed to the term “insulating layer” in some cases.
- the refractive index n includes n Ordinary which is the refractive index of ordinary light, n Extraordinary which is the refractive index of extraordinary light, and n average which is the average value of both.
- n average when the anisotropy analysis is not performed
- n Original when the anisotropy analysis is performed.
- Anisotropy is represented by the difference between n Original and n Extraordinary. Note that n average is a value obtained by dividing a value obtained by doubling a value of n Original and a value obtained by dividing the value of n Extraordinary by 3.
- room temperature refers to a temperature in the range of 0 ° C. to 40 ° C.
- the electronic device 50 includes a pair of electrodes (electrode 11 and electrode 12) and the organic semiconductor layer 20 between a pair of substrates (substrate 10 and substrate 15).
- the organic semiconductor layer 20 has at least a carrier transport layer 30 and a functional layer 40.
- the organic semiconductor layer 20 may have a plurality of functional layers.
- the functional layer 40 of the electronic device 50 preferably has a function of absorbing or emitting light.
- the light that has passed through the substrate 10 passes through the electrode 11 and the carrier transport layer 30.
- the light that has entered the organic semiconductor layer 20 from the electrode 11 side is absorbed by the functional layer 40, the light that has passed through the substrate 10 passes through the electrode 11 and the carrier transport layer 30.
- the amount of light attenuated in the electrode 11 and the carrier transport layer 30 is small.
- an attenuation mode called an evanescent mode.
- the light generated in the functional layer 40 is attenuated by the evanescent mode when passing or reflecting through the electrode 11.
- the carrier transport layer 30 is required to have carrier transport properties or carrier injection properties. Therefore, the carrier transport layer 30 uses a carrier-accepting or carrier-donating substance. Since the carrier-accepting or carrier-donating substance is often a material having a high refractive index, the carrier transport layer 30 has a high refractive index. That is, it was difficult to obtain a layer having a low refractive index while having carrier transportability. In addition, when the carrier-accepting or carrier-donating substance is an organic compound, it is known that the refractive index decreases if the organic compound has a saturated cyclic compound such as a cyclohexane skeleton in the structure. There was a problem with heat resistance.
- the present inventors mixed an organic compound having a low refractive index into the carrier transport layer 30, so that even if a substance having an electron accepting property having a high refractive index is used, the refractive index is low while having carrier transportability. It has been found that low layers can be made. Further, by mixing either the tetraarylmethane skeleton or the tetraarylsilane skeleton and an organic compound having an electron donating group into the carrier transport layer 30, a substance having an electron accepting property having a high refractive index may be used. The inventors have found that a layer having a carrier transportability and a low refractive index can be produced. In addition, the present inventors have found that the organic compound is excellent in heat resistance.
- the refractive index of the organic compound having a low refractive index is preferably 1 or more and 1.75 or less, more preferably 1 or more and 1.73 or less, and still more preferably 1.70 or less. With this configuration, it is possible to obtain a good electronic device with reduced light attenuation.
- the refractive index of either the tetraarylmethane skeleton or the tetraarylsilane skeleton and the organic compound having an electron donating group is preferably 1 or more and 1.75 or less, more preferably 1 or more and 1.73 or less, Preferably it is 1.70 or less.
- FIG. 2A is a schematic cross-sectional view of the light-emitting element 150 of one embodiment of the present invention.
- the light-emitting element 150 includes a substrate 200 and a substrate 210.
- the light-emitting element 150 includes a pair of electrodes (an electrode 101 and an electrode 102) between the substrate 200 and the substrate 210, and the EL layer 100 provided between the pair of electrodes.
- the EL layer 100 includes at least a light emitting layer 130.
- the EL layer 100 illustrated in FIG. 2A includes functional layers such as a hole injection layer 111, a hole transport layer 112, an electron transport layer 118, and an electron injection layer 119.
- the electrode 101 is an anode and the electrode 102 is a cathode of the pair of electrodes, but the structure of the light-emitting element 150 is not limited thereto. That is, the electrode 101 may be a cathode, the electrode 102 may be an anode, and the layers stacked between the electrodes may be reversed. That is, from the anode side, the hole injection layer 111, the hole transport layer 112, the light emitting layer 130, the electron transport layer 118, and the electron injection layer 119 may be stacked.
- the electrode 101 (anode) side is described as the light extraction side in FIG. 2A, but the structure of the light-emitting element 150 is not limited thereto. That is, the light extraction side may be the electrode 102 (cathode) side, or light may be extracted from both the electrode 101 and the electrode 102.
- the structure of the EL layer 100 is not limited to the structure illustrated in FIG. 2A, and includes at least the light-emitting layer 130, the hole-injection layer 111, the hole-transport layer 112, the electron-transport layer 118, and the electron-injection Each of the layers 119 may or may not be included.
- the EL layer 100 can reduce the hole or electron injection barrier, improve the hole or electron transport property, inhibit the hole or electron transport property, or suppress the quenching phenomenon caused by the electrode. It is good also as a structure which has a functional layer which has a function of being able to suppress child diffusion. Note that each functional layer may be a single layer or a structure in which a plurality of layers are stacked.
- FIG. 2B is a schematic cross-sectional view illustrating an example of the light-emitting layer 130 illustrated in FIG.
- the light-emitting layer 130 illustrated in FIG. 2B may include a guest material 131 and a host material 132.
- the light extraction efficiency of the light emitting element 150 is preferably high.
- an attenuation mode called an evanescent mode.
- light generated in the light emitting layer 130 is attenuated by the evanescent mode when passing through or reflecting the electrode 101.
- the light-emitting element 150 In the light-emitting element 150, light generated in the light-emitting layer 130 is extracted to the outside. However, if a layer having a low refractive index exists before the light generated in the light-emitting layer 130 passes through the substrate 200, the light extraction efficiency is increased. Is known to improve.
- the refractive index of the hole injection layer 111 or the hole transport layer 112 is preferably low.
- the refractive index of the hole injection layer 111 in contact with the electrode 101 is preferably low.
- the hole injection layer 111 in order to obtain hole injection characteristics in the hole injection layer 111, a substance having an electron accepting property is mixed with an organic compound having an electron donating property. Since there are many materials having a high refractive index for the substance having an electron accepting property, the hole injection layer 111 has a high refractive index. That is, it was difficult to obtain a layer having a hole injection property and a low refractive index.
- the electron-accepting or electron-donating substance is an organic compound, it is known that the refractive index decreases when a saturated cyclic compound such as a cyclohexane skeleton is included in the structure of the organic compound. There was a problem with heat resistance.
- the present inventors have a hole injection characteristic and a refractive index even when a substance having a high refractive index is used. It was found that a low layer can be produced. Further, the present inventors mixed electrons having a high refractive index by mixing an organic compound having at least one of a tetraarylmethane skeleton or a tetraarylsilane skeleton and an electron-donating group into the hole injection layer 111. It has been found that even if a substance having acceptability is used, a layer having a low refractive index while having carrier transportability can be produced. Furthermore, it discovered that this organic compound was excellent also in heat resistance.
- the glass transition point (Tg) of the organic compound is preferably 100 ° C. or higher.
- the refractive index of the organic compound having a low refractive index is preferably 1 or more and 1.75 or less, more preferably 1 or more and 1.73 or less, and still more preferably 1.70 or less. With this configuration, a light-emitting element with favorable light extraction efficiency can be obtained.
- the organic compound having either the tetraarylmethane skeleton or the tetraarylsilane skeleton and the electron donating group preferably has a refractive index of 1 or more and 1.75 or less, more preferably 1 or more and 1.73 or less, Preferably it is 1.70 or less. With this configuration, a light-emitting element with favorable light extraction efficiency can be obtained.
- a layer having a low refractive index exists between the light emitting layer 130 and the substrate 200, the light extraction efficiency is improved.
- a layer having a low refractive index is used in addition to the hole injection layer 111 and the hole transport layer 112.
- the number of layers to be manufactured increases, so that the manufacturing process of the light-emitting element becomes complicated.
- a layer having a low refractive index and hole injection characteristics can be manufactured. Therefore, using a conventional manufacturing process, that is, while maintaining the number of layers to be manufactured, The light extraction efficiency of the light emitting element can be improved.
- the refractive index is low and the hole injection property is improved.
- the light extraction efficiency of the light-emitting element can be improved by using a conventional manufacturing process, that is, without increasing the number of layers to be manufactured.
- One embodiment of the present invention relates to an EL layer between an anode and a cathode. Therefore, it can be combined with other light extraction enhancement techniques such as forming irregularities on the substrate.
- an organic compound having an electron donating property is preferably used as the organic compound having a low refractive index.
- the organic compound having a low refractive index since the hole injection characteristics can be improved while reducing the refractive index of the hole injection layer 111, a light-emitting element having a good light extraction efficiency and a low driving voltage is provided. be able to.
- the organic compound has a tetraarylmethane skeleton or a tetraarylsilane skeleton.
- the refractive index of the hole injection layer 111 is preferably lower than the refractive index of the light emitting layer 130. With this configuration, attenuation due to evanescent waves of light emission from the light emitting layer 130 can be reduced.
- the refractive index of the hole injection layer 111 is preferably lower than the refractive index of the hole transport layer 112, and the refractive index of the hole transport layer 112 is more preferably lower than the refractive index of the light emitting layer 130. With this configuration, the refractive index difference between the light emitting layer 130 and the hole injection layer 111 can be reduced, so that the light extraction efficiency can be further improved.
- the number of layers through which light generated in the light emitting layer 130 passes is smaller. Therefore, it is preferable that the light-emitting layer 130 is in contact with the electrode 101 in consideration of light extraction efficiency. However, with this configuration, the light-emitting efficiency of the light-emitting layer 130 is reduced due to the influence of the carrier balance and the plasmon effect. There is a case. Therefore, the hole injection layer 111 and the hole transport layer 112 are layers necessary for efficiently functioning the EL layer. Therefore, the hole injection layer 111 and the hole transport layer 112 are preferably in contact with each other, and more preferably, the hole transport layer 112 and the light emitting layer 130 are in contact with each other.
- the refractive index of the hole injection layer 111 is preferably lower than the refractive index of the electrode 101.
- the refractive index of the hole injection layer 111 is preferably 1 or more and 1.80 or less. More preferably, they are 1 or more and 1.78 or less, More preferably, they are 1 or more and 1.75 or less. With this configuration, good light extraction efficiency can be obtained.
- the hole injection layer 111 it is preferable to mix an organic compound having an electron donating property and a substance having an electron accepting property. With this configuration, good hole injection characteristics can be obtained.
- the mixing ratio of the organic compound and the substance having an electron accepting property is preferably such that the volume ratio of the substance having an electron accepting property is 0.01 or more and 0.3 or less with respect to the organic compound.
- the above-described attenuation of light by the evanescent wave can also occur for light incident on the electronic device.
- the electronic device according to one embodiment of the present invention when the electronic device according to one embodiment of the present invention is applied to a solar cell, attenuation of light due to the evanescent wave can be suppressed, so that the light confinement effect of the solar cell can be improved. Therefore, the electronic device according to one embodiment of the present invention can be favorably used for a solar cell.
- the functional layer 40 in the electronic device 50 shown in FIG. 1 may be read as an active layer, a light absorption layer, or a photovoltaic layer.
- An organic compound having a low refractive index is preferably used for the hole injection layer 111.
- the refractive index of the polymer is represented by the Lorentz-Lorenz equation (Equation (1)) shown below.
- Equation (2) is obtained by transforming Equation (1).
- Equation (1) in Equation (2), n is the refractive index, alpha is polarizability, N is the number of molecules per unit volume, [rho is the density, N A is Avogadro's number, M is the molecular weight, V 0 is the molar volume, [R] represents atomic refraction.
- ⁇ may be reduced.
- atomic refraction [R] may be reduced. That is, in order to reduce the refractive index n, an organic compound having a small atomic refraction [R] may be selected.
- the above formula is a formula for macromolecules, when applied to low molecular weight compounds, it is expected that there will be some deviation in the calculated value.
- the organic compound used for the injection layer 111 it is preferable to select an organic compound having a small atomic refraction [R]. Further, the hole injection layer 111 preferably has hole injection characteristics. Therefore, it is more preferable that the organic compound used for the hole injection layer 111 further has ⁇ conjugation in the molecule and an electron donating property like an aromatic compound. By selecting such an organic compound, the hole injection layer 111 having a low refractive index and excellent hole injection characteristics can be manufactured.
- Atomic refraction [R] is a fluorine-containing substituent such as a fluoro group or a trifluoromethyl group, a cyclohexyl group, or a bond via an aromatic ring, represented by sp 3 hybrid orbitals, and the conjugation between aromatic rings is broken. When it has a structure, it tends to be small. In addition, organic compounds having non-alternating hydrocarbons tend to have small atomic refraction [R] because the conjugated system does not extend throughout the molecule. Therefore, the organic compound used for the hole injection layer 111 is preferably an organic compound having the above substituent or bond.
- the organic compound used for the hole injection layer 111 includes an aromatic compound having an aromatic amine skeleton, a pyrrole skeleton, a thiophene skeleton, and an aromatic ring having a bulky substituent such as a methyl group, a t-butyl group, or an isopropyl group.
- the organic compound which has can also be used suitably.
- the organic compound has a ⁇ -conjugated system in the molecule and tends to have a low refractive index.
- Examples of structures in which the conjugation between aromatic rings is broken in the bond via the aromatic ring described above include a tetraarylmethane skeleton represented by the following general formula (100) and a tetraarylsilane represented by the general formula (101) Examples thereof include a skeleton and a cyclohexyl skeleton. Since the tetraarylmethane skeleton and the tetraarylsilane skeleton have a low refractive index and better heat resistance than the cyclohexyl skeleton, the tetraarylmethane skeleton and the tetraarylsilane skeleton can be preferably used for the hole injection layer 111. Moreover, since a thin film can be easily formed by vacuum deposition, it can be used suitably for electronic devices such as organic EL.
- the organic compound used for the hole injection layer 111 preferably has an electron donating property.
- the skeleton having an electron donating property include aromatic amine skeletons and ⁇ electron-rich heteroaromatic skeletons represented by the following general formulas (200) to (220).
- X in the general formulas (210) to (213) represents oxygen or sulfur.
- Aromatic amine skeleton (specifically, for example, triarylamine skeleton), ⁇ -electron rich heteroaromatic skeleton (specifically, for example, a ring having a furan skeleton, a thiophene skeleton, a pyrrole skeleton, an azepine skeleton, or an acridine skeleton) May have a substituent.
- a substituent an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms can also be selected. it can.
- alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group.
- cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- aryl group having 6 to 12 carbon atoms include a phenyl group, a naphthyl group, and a biphenyl group.
- the above substituents may be bonded to each other to form a ring.
- the spirofluorene skeleton is formed by bonding the phenyl groups together. .
- the skeleton having electron donating properties is preferably an odd-membered ring skeleton such as an aromatic amine skeleton, a pyrrole skeleton, or an azepine skeleton, or an acridine skeleton. Since these skeletons have good electron donating properties and low atomic refraction [R], organic compounds having excellent electron donating properties and low refractive index can be obtained by having these skeletons in the molecule. .
- Ar 1 to Ar 8 are each independently an aryl group having 6 to 13 carbon atoms, an aromatic amine skeleton represented by the above general formulas (200) to (220), or a ⁇ -electron rich heteroaromatic group. Represents the skeleton.
- the aryl group may have a substituent, and the substituents may be bonded to each other to form a ring.
- the 9-position carbon of the fluorenyl group has two phenyl groups as substituents, and the phenyl groups are bonded to each other to form a spirofluorene skeleton. .
- aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthalenyl group, and a fluorenyl group.
- substituents include an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a carbon group having 6 to 12 carbon atoms.
- Aryl groups can also be selected.
- alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group.
- cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- aryl group having 6 to 12 carbon atoms include a phenyl group and a naphthyl group.
- aryl group represented by Ar 1 to Ar 8 for example, a group represented by the following structural formula can be applied. Note that groups that can be used as the aryl group are not limited thereto.
- the aryl group is a substituent having a relatively small ⁇ -conjugated system spread, such as a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. And a substituted or unsubstituted phenyl group is more preferred.
- a substituent having a small ⁇ -conjugated system tends to have a small atomic refraction [R].
- organic compounds having a small ⁇ -conjugated system such as alkenes are not suitable for electronic devices because of poor carrier transportability.
- an organic compound having a carrier transport property and a small ⁇ -conjugated system such as an aryl group having 6 to 13 carbon atoms, particularly a phenyl group, is preferable as the organic compound used for the hole-injecting layer 111.
- an organic compound having a carrier transport property and a small ⁇ -conjugated system such as an aryl group having 6 to 13 carbon atoms, particularly a phenyl group, is preferable as the organic compound used for the hole-injecting layer 111.
- the substituent of an odd-membered ring has small atomic refraction [R], it is preferable.
- R 1 to R 11 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms atoms, or, It represents either a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.
- Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group. Can do.
- cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- aryl group having 6 to 13 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, and a fluorenyl group.
- the aryl group and phenyl group described above may have a substituent, and the substituents may be bonded to each other to form a ring.
- an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms can also be selected.
- Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group.
- cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- aryl group having 6 to 12 carbon atoms include a phenyl group, a naphthyl group, and a biphenyl group.
- R 1 to R 11 groups represented by the following structural formulas (R-1) to (R-27) can be applied. Note that groups that can be used as an alkyl group or an aryl group are not limited thereto.
- Ar 9 to Ar 13 represent an arylene group having 6 to 13 carbon atoms, and the arylene group may have a substituent. May combine with each other to form a ring.
- the 9-position carbon of the fluorenyl group has two phenyl groups as substituents, and the phenyl groups are bonded to each other to form a spirofluorene skeleton.
- Specific examples of the arylene group having 6 to 13 carbon atoms include a phenylene group, a naphthalenediyl group, a biphenylene group, and a fluorenediyl group.
- the substituent when the arylene group has a substituent, the substituent includes an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a carbon group having 6 to 12 carbon atoms.
- Aryl groups can also be selected. Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and an n-hexyl group. Can do.
- cycloalkyl group having 3 to 6 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- aryl group having 6 to 12 carbon atoms include a phenyl group, a naphthyl group, and a biphenyl group.
- arylene group represented by Ar 9 to Ar 13 for example, groups represented by the following structural formulas (Ar-12) to (Ar-25) can be applied. Note that groups that can be used as Ar 9 to Ar 13 are not limited thereto.
- the organic compound used for the hole injection layer 111 is preferably a tetraarylmethane skeleton or a tetraarylsilane skeleton and an organic compound having an electron donating property.
- the organic compound include 9- (4-t-butylphenyl) -3,4-ditrityl-9H-carbazole (abbreviation: CzC), 9- (4-t-butylphenyl) -3,4-ditrile.
- Phenylsilyl-9H-carbazole (abbreviation: CzSi), 4,4,8,8, -12,12-hexa-p-toluyl-4H-8H-12H-12C-aza-dibenzo [cd, mn] pyrene (abbreviation) : FATPA), 4,4′-bis (dibenzo-azepin-1-yl) -biphenyl (abbreviation: BazBP), 4,4′-bis (dihydro-dibenzo-azepin-1-yl) -biphenyl (abbreviation: HBazBP) ), 4,4 ′-(diphenylmethylene) bis (N, N-diphenylamine) (abbreviation: TCBPA), 4,4 ′-(diphenylsilanediyl) bis (N, N-diphe) Triethanolamine) (abbreviation: TSBPA), and the like. These structural formulas are shown below
- a low-molecular organic compound can be favorably used for the electronic device according to one embodiment of the present invention.
- a low molecular weight organic compound By using a low molecular weight organic compound, all the layers included in the EL layer 100 can be formed by vacuum deposition, so that the manufacturing process can be simplified.
- the light extraction efficiency can be further improved by controlling the optical path length.
- the light emitted from the light emitting layer 130 light having a desired wavelength can be extracted efficiently.
- a region where light having a desired wavelength of the light emitting layer 130 can be obtained from the interface between the electrode 101 and the hole injection layer 111 (The optical distance to the light emitting region 134) is preferably adjusted to be in the vicinity of (2m′ ⁇ 1) ⁇ / 4 (where m ′ is a natural number).
- the light emitting region here refers to a recombination region of holes and electrons in the light emitting layer 130.
- the optical distance from the interface between the substrate 200 and the electrode 101 and the light emitting layer 130 to the region where the light having a desired wavelength is obtained is adjusted to be close to m ⁇ / 2 (where m is a natural number). Is preferred. By performing such optical adjustment, light attenuation due to the evanescent mode can be reduced, so that the light extraction efficiency from the light emitting layer 130 can be improved.
- the refractive index of the hole injection layer 111 is high, the optical path length tends to be long. For this reason, it may be difficult to adjust the optical path length, or the thickness of the hole injection layer 111 may be increased, and the drive voltage may increase.
- the hole injection layer 111 since the hole injection layer 111 has a low refractive index, the optical path length can be easily controlled and the film thickness can be reduced. Therefore, not only the light extraction efficiency from the light emitting layer 130 can be improved, but also a light emitting element manufacturing process can be simplified and a light emitting element having a low driving voltage can be realized.
- the above-described attenuation of light by the evanescent wave can also occur for light incident on the electronic device.
- the electronic device according to one embodiment of the present invention when the electronic device according to one embodiment of the present invention is applied to a solar cell, light attenuation due to an evanescent wave can be suppressed; thus, the light confinement effect of the organic solar cell can be improved. Therefore, the electronic device according to one embodiment of the present invention can be favorably used for a solar cell.
- the functional layer 40 in the electronic device 50 shown in FIG. 1 may be read as an active layer.
- the light-emitting layer 130 preferably includes at least a host material 131 and further includes a guest material 132. Further, as described later, the host material 131 may include an organic compound 131_1 and an organic compound 131_2. In the light emitting layer 130, the host material 131 is present in the largest amount by weight, and the guest material 132 is dispersed in the host material 131. When the guest material 132 is a fluorescent compound, the S1 level of the host material 131 (the organic compound 131_1 and the organic compound 131_2) of the light-emitting layer 130 is higher than the S1 level of the guest material (guest material 132) of the light-emitting layer 130. It is preferable.
- the T1 level of the host material 131 (the organic compound 131_1 and the organic compound 131_2) of the light-emitting layer 130 is higher than the T1 level of the guest material (guest material 132) of the light-emitting layer 130. Is preferably high.
- the organic compound 131_1 preferably has a heteroaromatic skeleton having 1 to 20 carbon atoms containing two or more nitrogen atoms.
- a compound having a pyrimidine skeleton and a triazine skeleton is preferable.
- a material having an electron transport property higher than that of holes can be used, and the material has an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher. preferable.
- 4,6-bis [3- (phenanthrene-9-yl) phenyl] pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis [3- (4-dibenzothienyl) phenyl] pyrimidine Heterocyclic compounds having a diazine skeleton such as (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis [3- (9H-carbazol-9-yl) phenyl] pyrimidine (abbreviation: 4,6mCzP2Pm), 2- ⁇ 4- [3- (N-phenyl-9H-carbazol-3-yl) -9H-carbazol-9-yl] phenyl ⁇ -4,6-diphenyl-1,3,5-triazine (Abbreviation: PCCzPTzn), 2- ⁇ 3- [3- (benzo [b] naphtho [1,2-d] furan-8-y
- the heterocyclic compound having the skeleton has a high electron transporting property and contributes to a reduction in driving voltage.
- the substances mentioned here are mainly substances having an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher. Note that other than the above substances, any substance that has a property of transporting more electrons than holes may be used.
- organic compound 131_1 compounds such as a pyridine derivative, a pyrazine derivative, a pyridazine derivative, a bipyridine derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, a phenanthroline derivative, and a purine derivative can also be used.
- Such an organic compound is preferably a material having an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher.
- heterocyclic compounds having a pyridine skeleton such as bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f , H] quinoxaline (abbreviation: 2mDBTPDBq-II), 2- [3 ′-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPBPDBq-II), 2- [ 3 ′-(9H-carbazol-9-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mCzBPDBq), 2- [4- (3,6-diphenyl-9H-carbazole-9) -Yl) phenyl] dibenzo [f, h]
- BPhen
- poly (2,5-pyridinediyl) (abbreviation: PPy)
- poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF -Py)
- poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy)
- PF-BPy poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)]
- the organic compound 131_2 preferably has a C 1-20 heteroaromatic skeleton containing two or more nitrogen atoms.
- a nitrogen-containing hetero five-membered ring skeleton is particularly preferable. Examples thereof include an imidazole skeleton, a triazole skeleton, and a tetrazole skeleton.
- a material having a property of transporting more holes than electrons can be used, and a material having a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or more. It is preferable that
- the hole transporting material may be a polymer compound.
- 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (abbreviation: TAZ)
- 9- [4- (4 , 5-Diphenyl-4H-1,2,4-triazol-3-yl) phenyl] -9H-carbazole (abbreviation: CzTAZ1), 2,2 ′, 2 ′′-(1,3,5-benzenetriyl )
- Tris (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2- [3- (dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) ) Etc.
- TAZ 9- [4- (4 , 5-Diphenyl-4H-1,2,4-triazol-3-yl) phenyl] -9H-c
- organic compound 131_2 other compounds having a nitrogen-containing hetero five-membered ring skeleton or a tertiary amine skeleton can also be preferably used. Specific examples include a pyrrole skeleton or an aromatic amine skeleton. For example, indole derivatives, carbazole derivatives, triarylamine derivatives and the like can be mentioned.
- a material having a property of transporting more holes than electrons (a hole transporting material) can be used, and a material having a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or more. It is preferable that The hole transporting material may be a polymer compound.
- N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA) 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB)
- N, N′-bis ⁇ 4- [bis (3-methylphenyl) amino] phenyl ⁇ -N, N′-diphenyl- (1,1′-biphenyl) -4,4′-diamine (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N— Phenylamino] benzene (abbreviation: DPA3B) and the like.
- PCzDPA1 3- [N- (4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole
- PCzDPA2 3,6-bis [N- ( 4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole
- PCzTPN2 3,6-bis [N- (4-diphenylaminophenyl) -N- (1-naphthyl) amino] -9 -Phenylcarbazole
- PCzTPN2 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole
- PCzPCA1 3,6-bis [ N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole
- PCzPCA1 3,6-bis [ N- (9-phenylcarbazol
- examples of the carbazole derivative include 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (abbreviation). : TCPB), 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA), 1,4-bis [4- (N-carbazolyl) phenyl] -2, 3,5,6-tetraphenylbenzene or the like can be used.
- CBP 4,4′-di (N-carbazolyl) biphenyl
- CzPA 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole
- CzPA 1,4-bis [4- (N-carbazolyl) phenyl] -2, 3,5,6-tetraphenyl
- poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD can also be used.
- NPB or ⁇ -NPD 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
- NPB or ⁇ -NPD N, N′— Bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine
- TPD 4,4 ′, 4 ′′ -tris (carbazole-9) -Yl) triphenylamine
- TCTA 4,4 ′, 4 ′′ -tris [N- (1-naphthyl) -N-phenylamino] triphenylamine
- 1′-TNATA 4, 4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine
- TDATA 4,4 ′, 4 ′, 4 ′, 4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine
- PCPN 3- [4- (1-naphthyl) -phenyl] -9-phenyl-9H-carbazole
- PCPPn 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole
- PCCP 3,3′-bis (9-phenyl-9H-carbazole)
- mCP 1,3-bis (N-carbazolyl) benzene
- mCP 1,3-bis (N-carbazolyl) benzene
- CzTP 3,5-diphenylphenyl) -9-phenylcarbazole
- PhCzGI 3,6-di (9H-carbazol-9-yl) -9-phenyl-9H-carbazole
- PhCzGI 2,8- An amine compound such as di (9H-carbazol-9-yl) -dibenzothiophene
- a compound having a pyrrole skeleton or an aromatic amine skeleton is preferable because it is stable and reliable.
- the compound having the skeleton has a high hole transport property and contributes to a reduction in driving voltage.
- the guest material 132 is not particularly limited.
- the fluorescent compound include anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, acridone derivatives, coumarins.
- Derivatives, phenoxazine derivatives, phenothiazine derivatives, and the like are preferable. For example, the following substances can be used.
- Examples of the guest material 132 include iridium, rhodium, or platinum-based organometallic complexes, or metal complexes.
- organic iridium complexes such as iridium-based orthometal complexes are preferable.
- Examples of orthometalated ligands include 4H-triazole ligands, 1H-triazole ligands, imidazole ligands, pyridine ligands, pyrimidine ligands, pyrazine ligands, and isoquinoline ligands.
- Examples of the metal complex include a platinum complex having a porphyrin ligand.
- organometallic iridium complexes having a nitrogen-containing five-membered heterocyclic skeleton such as a 4H-triazole skeleton, a 1H-triazole skeleton, and an imidazole skeleton have high triplet excitation energy, and have high reliability and luminous efficiency. It is particularly preferred because of its superiority.
- Examples of a substance having an emission peak in green or yellow include tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: Ir (mppm) 3 ), tris (4-t-butyl). -6-phenylpyrimidinato) iridium (III) (abbreviation: Ir (tBupppm) 3 ), (acetylacetonato) bis (6-methyl-4-phenylpyrimidinato) iridium (III) (abbreviation: Ir (mppm) ) 2 (acac)), (acetylacetonato) bis (6-tert-butyl-4-phenylpyrimidinato) iridium (III) (abbreviation: Ir (tBupppm) 2 (acac)), (acetylacetonato) bis [4- (2-norbornyl) -6-phenylpyrimidinato] iridium (III) (abbrevi
- organometallic iridium complexes having a pyrimidine skeleton are particularly preferable because they are remarkably excellent in reliability and luminous efficiency.
- An organometallic iridium complex having a pyrazine skeleton can emit red light with good chromaticity.
- the light-emitting material contained in the light-emitting layer 130 is preferably a material that can convert triplet excitation energy into light emission.
- the material capable of converting the triplet excitation energy into light emission include a thermally activated delayed fluorescence (TADF) material in addition to a phosphorescent compound. Therefore, the portion described as a phosphorescent compound may be read as a thermally activated delayed fluorescent material.
- TADF thermally activated delayed fluorescence
- the thermally activated delayed fluorescent material has a small difference between the triplet excitation energy level and the singlet excitation energy level, and the function of converting energy from the triplet excited state to the singlet excited state by crossing between inverses. It is the material which has.
- the triplet excited state can be up-converted (reverse intersystem crossing) into a singlet excited state with a slight thermal energy, and light emission (fluorescence) from the singlet excited state can be efficiently exhibited.
- the energy difference between the triplet excitation energy level and the singlet excitation energy level is preferably greater than 0 eV and not greater than 0.2 eV, and more preferably greater than 0 eV. It is mentioned that it is 0.1 eV or less.
- the heat activated delayed fluorescent material is composed of one kind of material, for example, the following materials can be used.
- metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), and the like can be given.
- metal-containing porphyrin include a protoporphyrin-tin fluoride complex (SnF 2 (ProtoIX)), a mesoporphyrin-tin fluoride complex (SnF 2 (Meso IX)), and a hematoporphyrin-tin fluoride complex (SnF 2).
- a thermally activated delayed fluorescent material composed of a kind of material a heterocyclic compound having a ⁇ -electron rich heteroaromatic ring and a ⁇ -electron deficient heteroaromatic ring can also be used.
- the heterocyclic compound has a ⁇ -electron rich heteroaromatic ring and a ⁇ -electron deficient heteroaromatic ring, it is preferable because of its high electron transporting property and hole transporting property.
- a diazine skeleton pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton
- a triazine skeleton is preferable because it is stable and has high reliability.
- an acridine skeleton, a phenoxazine skeleton, a thiophene skeleton, a furan skeleton, and a pyrrole skeleton are stable and reliable. It is preferable to have one or more.
- the pyrrole skeleton an indole skeleton, a carbazole skeleton, and a 3- (9-phenyl-9H-carbazol-3-yl) -9H-carbazole skeleton are particularly preferable.
- a substance in which a ⁇ -electron rich heteroaromatic ring and a ⁇ -electron deficient heteroaromatic ring are directly bonded has both a donor property of a ⁇ -electron rich heteroaromatic ring and an acceptor property of a ⁇ -electron deficient heteroaromatic ring, This is particularly preferable because the difference between the energy level in the singlet excited state and the energy level in the triplet excited state is small.
- the light emitting layer 130 may have a material other than the host material 131 and the guest material 132.
- a material that can be used for the light-emitting layer 130 is not particularly limited, and examples thereof include condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo [g, p] chrysene derivatives.
- 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9′- Bianthryl (abbreviation: BANT), 9,9 ′-(stilbene-3,3′-diyl) diphenanthrene (abbreviation: D) NS), 9,9 ′-(stilbene-4,4′-diyl) diphenanthrene (abbreviation: DPNS2), 1,3,5-tri (1-pyrenyl) benzene (abbreviation: TPB3)
- a compound having a heteroaromatic skeleton such as an oxadiazole derivative can be used for the light-emitting layer 130.
- a compound having a heteroaromatic skeleton such as an oxadiazole derivative
- PBD 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazol
- OXD-7 1,3-bis [5- (P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene
- OXD-7 1,3-bis [5- (P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene
- OXD-7 1,3-bis [5- (P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene
- OXD-7 1,3-bis [5- (P-tert-
- a metal complex having a heterocyclic ring eg, zinc and aluminum-based metal complex
- a metal complex having a quinoline ligand, a benzoquinoline ligand, an oxazole ligand, or a thiazole ligand can be given.
- tris (8-quinolinolato) aluminum (III) (abbreviation: Alq)
- tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq 3 )
- bis (10-hydroxybenzo) [H] quinolinato) beryllium (II) (abbreviation: BeBq 2 )
- bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) abbreviation: BAlq
- bis (8-quinolinolato) zinc (II) (abbreviation: Znq) and the like
- metal complexes having a quinoline skeleton or a benzoquinoline skeleton include metal complexes having a quinoline skeleton or a benzoquinoline skeleton.
- bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), etc.
- ZnPBO bis [2- (2-benzoxazolyl) phenolato] zinc
- ZnBTZ bis [2- (2-benzothiazolyl) phenolato] zinc
- a metal complex having an oxazole-based or thiazole-based ligand can also be used.
- the light emitting layer 130 can also be comprised with two or more layers.
- a substance having a hole-transport property is used as the host material of the first light-emitting layer
- a substance having an electron transporting property is used as a host material of the second light emitting layer.
- the light-emitting materials included in the first light-emitting layer and the second light-emitting layer may be the same material or different materials, and may be different materials that have a function of emitting light of the same color.
- a material having a function of emitting light of a color may be used.
- a light emitting material having a function of emitting light of different colors for each of the two light emitting layers, a plurality of light emissions can be obtained simultaneously.
- the light emitting layer 130 can be formed by a method such as a vapor deposition method (including a vacuum vapor deposition method), an ink jet method, a coating method, or gravure printing. Further, in addition to the materials described above, an inorganic compound such as a quantum dot or a polymer compound (oligomer, dendrimer, polymer, etc.) may be included.
- the hole injection layer 111 has a function of promoting hole injection by reducing a hole injection barrier from one of the pair of electrodes (the electrode 101 or the electrode 102).
- a transition metal oxide having electron acceptability It is formed by phthalocyanine derivatives, aromatic amines, heteropolyacids, and the like.
- Transition metal oxides include titanium oxide, vanadium oxide, tantalum oxide, molybdenum oxide, tungsten oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, and silver oxide.
- the transition metal oxide is preferable because it is excellent in electron acceptability and can be easily formed by a vacuum deposition method or a wet method.
- phthalocyanine derivative examples include phthalocyanine and metal phthalocyanine.
- aromatic amines examples include benzidine derivatives and phenylenediamine derivatives.
- High molecular compounds such as polythiophene and polyaniline can also be used.
- self-doped polythiophene poly (ethylenedioxythiophene) / poly (styrenesulfonic acid) is a typical example.
- heteropolyacid include phosphomolybdic acid, phosphotungstic acid, silicomolybdic acid, and silicotungstic acid. Heteropolyacids and polymer compounds are preferred because they can be easily formed by a wet method.
- the hole injection layer 111 it is preferable to use a layer having a composite material of the hole transporting material having a low refractive index as described above and the material exhibiting the above-described electron accepting property. With such a structure, a layer having a low refractive index can be formed while having hole injection / transport properties.
- the organic material having an electron accepting property TCNQ, F4TCNQ, and F6TCNNQ can be preferably used.
- a stack of a layer containing a material exhibiting electron accepting properties and a layer containing a hole transporting material may be used. Charges can be transferred between these materials in a steady state or in the presence of an electric field.
- organic material exhibiting electron acceptability examples include organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives in addition to the above-described TCNQ, F4TCNQ, and F6TCCNQ.
- organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives in addition to the above-described TCNQ, F4TCNQ, and F6TCCNQ.
- an electron-withdrawing group (halogen) such as chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN). Group or a cyano group).
- a transition metal such as titanium, vanadium, tantalum, molybdenum, tungsten, rhenium, ruthenium, chromium, zirconium, hafnium, silver, and a substance containing oxygen
- molybdenum oxide is preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.
- the hole transporting material having a low refractive index used for the hole injection layer 111 is an organic compound having a structure in which conjugation between aromatic rings is broken, represented by sp3 bonds, or a bulky substituent.
- Examples of the skeleton having a structure in which the conjugation between aromatic rings is broken include the above-described tetraarylmethane skeleton and tetraarylsilane skeleton.
- such compounds tend to have poor carrier transport properties and are not suitable for conventional hole injection layers.
- a single substance containing a transition metal and oxygen as described above has a very high effect of enhancing the hole injection property, but has a problem that the refractive index is high.
- the hole injection layer 111 is refracted. It was found that the hole injection property and transport property can be secured while keeping the rate low. In other words, this configuration can cancel the disadvantages of both, and express only the merits. This is considered to be due to the fact that a substance containing a transition metal oxide has a high electron-accepting property, and a hole-injecting property can be ensured by adding a small amount.
- the hole transporting material As the hole transporting material, than the electron can be used transport material having high hole is preferably a material having a 1 ⁇ 10 -6 cm 2 / Vs or more hole mobility. As described above, the hole transporting material preferably has a refractive index of 1 or more and 1.75 or less, more preferably 1 or more and 1.73 or less, and still more preferably 1 or more and 1.70 or less. is there. Specifically, aromatic amines, carbazole derivatives, aromatic hydrocarbons, stilbene derivatives, and the like mentioned as hole transporting materials that can be used for the light-emitting layer 130 can be used, but carbon containing two or more nitrogen atoms can be used. It is particularly preferable to have a heteroaromatic skeleton of several 1 to 20. A nitrogen-containing hetero five-membered ring skeleton is particularly preferable.
- the hole transporting material may be a polymer compound.
- hole transporting material examples include aromatic hydrocarbons, such as 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 2-tert- Butyl-9,10-di (1-naphthyl) anthracene, 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis (4-phenylphenyl) ) Anthracene (abbreviation: t-BuDBA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-) BuAnth), 9,10-bis (4-methyl-1-naphthyl) anthracene
- pentacene, coronene, and the like can also be used.
- an aromatic hydrocarbon having a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or more and having 14 to 42 carbon atoms.
- the aromatic hydrocarbon may have a vinyl skeleton.
- the aromatic hydrocarbon having a vinyl group for example, 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2- Diphenylvinyl) phenyl] anthracene (abbreviation: DPVPA) and the like.
- a compound having a pyrrole skeleton, a furan skeleton, a thiophene skeleton, or an aromatic amine skeleton is preferable because it is stable and reliable.
- the compound having the skeleton has a high hole transport property and contributes to a reduction in driving voltage.
- the hole transport layer 112 is a layer containing a hole transport material, and the hole transport material exemplified as the material of the hole injection layer 111 can be used. Since the hole transport layer 112 has a function of transporting holes injected into the hole injection layer 111 to the light emitting layer 130, the HOMO (High Occupied Molecular Orbital) of the hole injection layer 111 is also known. It is preferable to have a HOMO level that is the same as or close to the position.
- a substance having a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher is preferable.
- any substance other than these may be used as long as it has a property of transporting more holes than electrons.
- the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.
- the electron transport layer 118 has a function of transporting electrons injected from the other of the pair of electrodes (the electrode 101 or the electrode 102) through the electron injection layer 119 to the light emitting layer 130.
- the electron transporting material a material having a higher electron transporting property than holes can be used, and a material having an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or more is preferable.
- a compound that easily receives electrons (a material having an electron transporting property)
- a ⁇ -electron deficient heteroaromatic such as a nitrogen-containing heteroaromatic compound, a metal complex, or the like can be used.
- the pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, phenanthroline derivatives, triazole derivatives, benzimidazole derivatives, oxalates which are listed as electron transporting materials that can be used for the light-emitting layer 130.
- Examples thereof include diazole derivatives, but it is preferable to have a heteroaromatic skeleton having 1 to 20 carbon atoms containing two or more nitrogen atoms.
- a compound having a pyrimidine skeleton and a triazine skeleton is preferable.
- a substance having an electron mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher is preferable.
- any substance that has a property of transporting more electrons than holes may be used for the electron-transport layer 118.
- the electron-transporting layer 118 is not limited to a single layer, and two or more layers including the above substances may be stacked.
- the metal complex which has a heterocyclic ring is mentioned,
- the metal complex which has a quinoline ligand, a benzoquinoline ligand, an oxazole ligand, or a thiazole ligand is mentioned.
- tris (8-quinolinolato) aluminum (III) (abbreviation: Alq)
- tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq 3 )
- bis (10-hydroxybenzo) [H] quinolinato) beryllium (II) (abbreviation: BeBq 2 )
- bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) abbreviation: BAlq
- bis (8-quinolinolato) zinc (II) (abbreviation: Znq) and the like
- metal complexes having a quinoline skeleton or a benzoquinoline skeleton include metal complexes having a quinoline skeleton or a benzoquinoline skeleton.
- bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), etc.
- ZnPBO bis [2- (2-benzoxazolyl) phenolato] zinc
- ZnBTZ bis [2- (2-benzothiazolyl) phenolato] zinc
- a metal complex having an oxazole-based or thiazole-based ligand can also be used.
- a layer for controlling the movement of electron carriers may be provided between the electron transport layer 118 and the light emitting layer 130.
- This is a layer obtained by adding a small amount of a substance having a high electron trapping property to a material having a high electron transporting property as described above. By suppressing the movement of electron carriers, the carrier balance can be adjusted.
- Such a configuration is highly effective in suppressing problems that occur when the electron transporting property of the electron transporting material is significantly higher than the hole transporting property of the hole transporting material (for example, a reduction in device lifetime). .
- the electron injection layer 119 has a function of promoting electron injection by reducing an electron injection barrier from the electrode 102.
- a Group 1 metal, a Group 2 metal, or an oxide, halide, carbonate, or the like thereof is used. Can be used.
- a composite material of the electron transporting material described above and a material exhibiting an electron donating property can be used. Examples of the material exhibiting electron donating properties include Group 1 metals, Group 2 metals, and oxides thereof.
- alkali metals such as lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiO x ), etc., alkaline earth Similar metals, or compounds thereof can be used.
- a rare earth metal compound such as erbium fluoride (ErF 3 ) can be used.
- electride may be used for the electron injection layer 119. Examples of the electride include a substance obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum.
- a substance that can be used for the electron-transport layer 118 may be used for the electron-injection layer 119.
- a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer 119.
- Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor.
- the organic compound is preferably a material excellent in transporting the generated electrons.
- a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer 118 described above is used.
- the electron donor may be any substance that exhibits an electron donating property to the organic compound.
- an alkali metal, an alkaline earth metal, or a rare earth metal is preferable, and examples thereof include lithium, sodium, cesium, magnesium, calcium, erbium, and ytterbium.
- Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
- a Lewis base such as magnesium oxide can also be used.
- an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
- the light emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer described above are formed by a vapor deposition method (including a vacuum vapor deposition method), an inkjet method, a coating method, a gravure printing, and the like, respectively. Can be formed by a method.
- the light emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer described above include inorganic compounds such as quantum dots, and polymer compounds (oligomers, dendrimers). , Polymers, etc.) may be used.
- a quantum dot is a semiconductor nanocrystal having a size of several nanometers to several tens of nanometers, and is composed of about 1 ⁇ 10 3 to 1 ⁇ 10 6 atoms. Since quantum dots shift in energy depending on the size, even if the quantum dots are made of the same material, the emission wavelength differs depending on the size. Therefore, the emission wavelength can be easily changed by changing the size of the quantum dots to be used.
- quantum dots since the quantum dot has a narrow emission spectrum peak width, it is possible to obtain light emission with good color purity. Furthermore, the theoretical internal quantum efficiency of quantum dots is said to be almost 100%, which is much higher than 25% of organic compounds that exhibit fluorescence and is equivalent to organic compounds that exhibit phosphorescence. For this reason, a light-emitting element with high emission efficiency can be obtained by using quantum dots as a light-emitting material. In addition, quantum dots, which are inorganic materials, are excellent in essential stability, and thus a light-emitting element that is preferable from the viewpoint of life can be obtained.
- the materials constituting the quantum dots include group 14 elements, group 15 elements, group 16 elements, compounds composed of a plurality of group 14 elements, elements belonging to groups 4 to 14 and group 16 elements.
- Compounds of Group 2, elements of Group 16 and Group 16, compounds of Group 13 elements and Group 15 elements, compounds of Group 13 elements and Group 17 elements, Group 14 elements and Group 15 Examples thereof include compounds with elements, compounds of Group 11 elements and Group 17 elements, iron oxides, titanium oxides, chalcogenide spinels, and semiconductor clusters.
- an alloy type quantum dot whose composition is represented by arbitrary ratios.
- an alloy type quantum dot of cadmium, selenium, and sulfur is one of effective means for obtaining blue light emission because the emission wavelength can be changed by changing the content ratio of elements.
- the structure of the quantum dot includes a core type, a core-shell type, and a core-multishell type, and any of them may be used, but the shell is covered with another inorganic material that covers the core and has a wider band gap.
- the shell material include zinc sulfide and zinc oxide.
- Quantum dots also have high reactivity because of a high proportion of surface atoms, and aggregation is likely to occur. Therefore, it is preferable that a protective agent is attached or a protective group is provided on the surface of the quantum dots. Aggregation can be prevented and solubility in a solvent can be increased by attaching the protective agent or providing a protective group. It is also possible to reduce the reactivity and improve the electrical stability.
- protecting agent examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, tripropylphosphine, tributylphosphine, trihexylphosphine, Trialkylphosphines such as octylphosphine, polyoxyethylene alkylphenyl ethers such as polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, tri (n-hexyl) amine, tri (n-octyl) Tertiary amines such as amine and tri (n-decyl) amine, tripropylphosphine oxide, tributylphosphine oxide, trihexylphosphine oxide, trioctylphosphite Organic phosphorus compounds such as oxide and tridecylphosphine oxide
- the size of the quantum dot is adjusted as appropriate so that light of a desired wavelength can be obtained.
- the crystal size decreases, the light emission of the quantum dots shifts to the blue side, that is, to the high energy side, so changing the size of the quantum dots changes the spectral wavelengths in the ultraviolet, visible, and infrared regions.
- the emission wavelength can be adjusted over a region.
- the size (diameter) of the quantum dots those in the range of 0.5 nm to 20 nm, preferably 1 nm to 10 nm are usually used.
- the quantum dot has a narrower size distribution, the emission spectrum becomes narrower and light emission with good color purity can be obtained.
- the shape of the quantum dots is not particularly limited, and may be spherical, rod-shaped, disk-shaped, or other shapes. Note that a quantum rod that is a rod-shaped quantum dot has a function of exhibiting light having directivity, and thus a light-emitting element with better external quantum efficiency can be obtained by using the quantum rod as a light-emitting material.
- organic EL elements increase luminous efficiency by dispersing a light emitting material in a host material and suppressing concentration quenching of the light emitting material.
- the host material needs to be a material having a singlet excitation energy level or a triplet excitation energy level higher than that of the light emitting material.
- a blue phosphorescent material is used as a light emitting material
- a host material having a triplet excitation energy level higher than that and having an excellent lifetime is required, and its development is extremely difficult.
- the quantum dots can maintain the light emission efficiency even if the light emitting layer is constituted only by the quantum dots without using the host material, a light emitting element that is preferable from this point of view can also be obtained.
- the quantum dots preferably have a core-shell structure (including a core-multishell structure).
- the film thickness of the light emitting layer is 3 nm to 100 nm, preferably 10 nm to 100 nm, and the content of quantum dots in the light emitting layer is 1 to 100% by volume.
- the quantum dots are dispersed in the host material, or the host material and the quantum dots are dissolved or dispersed in an appropriate liquid medium.
- a vacuum vapor deposition method for the light-emitting layer using a phosphorescent light-emitting material, in addition to the wet process, a vacuum vapor deposition method can be suitably used.
- liquid medium used in the wet process examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, and aromatic carbonization such as toluene, xylene, mesitylene, and cyclohexyl benzene. Hydrogen, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) can be used.
- ketones such as methyl ethyl ketone and cyclohexanone
- fatty acid esters such as ethyl acetate
- halogenated hydrocarbons such as dichlorobenzene
- aromatic carbonization such as toluene, xylene, mesitylene, and cyclohexyl benzene.
- the electrode 101 and the electrode 102 have a function as an anode or a cathode of the light emitting element.
- the electrode 101 and the electrode 102 can be formed using a metal, an alloy, a conductive compound, a mixture or a stacked body thereof.
- One of the electrode 101 and the electrode 102 is preferably formed of a conductive material having a function of reflecting light.
- the conductive material include aluminum (Al) or an alloy containing Al.
- the alloy containing Al include an alloy containing Al and L (L represents one or more of titanium (Ti), neodymium (Nd), nickel (Ni), and lanthanum (La)).
- Li represents one or more of titanium (Ti), neodymium (Nd), nickel (Ni), and lanthanum (La)).
- Al and Ti, or an alloy containing Al, Ni, and La Aluminum has a low resistance value and a high light reflectance. In addition, since aluminum is abundant in the crust and inexpensive, manufacturing cost of a light-emitting element by using aluminum can be reduced.
- N is yttrium (Y), Nd, magnesium (Mg), ytterbium (Yb), Al, Ti, gallium (Ga), zinc (Zn), indium (In) Represents one or more of tungsten (W), manganese (Mn), tin (Sn), iron (Fe), Ni, copper (Cu), palladium (Pd), iridium (Ir), or gold (Au) ) And the like.
- the alloy containing silver include an alloy containing silver, palladium and copper, an alloy containing silver and copper, an alloy containing silver and magnesium, an alloy containing silver and nickel, an alloy containing silver and gold, and silver and ytterbium. Examples thereof include alloys.
- transition metals such as tungsten, chromium (Cr), molybdenum (Mo), copper, and titanium can be used.
- At least one of the electrode 101 and the electrode 102 is preferably formed using a conductive material having a function of transmitting light.
- the conductive material is a conductive material having a visible light transmittance of 40% to 100%, preferably 60% to 100%, and a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ ⁇ cm or less. Can be mentioned.
- the electrode 101 and the electrode 102 may be formed of a conductive material having a function of transmitting light and a function of reflecting light.
- the conductive material include a conductive material having a visible light reflectance of 20% to 80%, preferably 40% to 70%, and a resistivity of 1 ⁇ 10 ⁇ 2 ⁇ ⁇ cm or less.
- it can be formed using one or more kinds of conductive metals, alloys, conductive compounds, and the like.
- ITO indium tin oxide
- ITSO indium tin oxide containing silicon or silicon oxide
- indium zinc oxide indium zinc oxide
- Metal oxides such as indium oxide containing indium oxide-tin oxide, indium-titanium oxide, tungsten oxide, and zinc oxide can be used.
- a metal thin film with a thickness that allows light to pass therethrough preferably, a thickness of 1 nm to 30 nm
- the metal for example, Ag or an alloy such as Ag and Al, Ag and Mg, Ag and Au, Ag and Yb, or the like can be used.
- the material having a function of transmitting light may be any material that has a function of transmitting visible light and has conductivity.
- an oxide semiconductor or an organic conductor including an organic substance is included.
- the organic conductor containing an organic substance include a composite material obtained by mixing an organic compound and an electron donor (donor), and a composite material obtained by mixing an organic compound and an electron acceptor (acceptor).
- an inorganic carbon-based material such as graphene may be used.
- the resistivity of the material is preferably 1 ⁇ 10 5 ⁇ ⁇ cm or less, and more preferably 1 ⁇ 10 4 ⁇ ⁇ cm or less.
- one or both of the electrode 101 and the electrode 102 may be formed by stacking a plurality of the above materials.
- a material having a higher refractive index than that of the electrode may be formed in contact with the electrode having a function of transmitting light.
- a material may be a material having a function of transmitting visible light, and may be a material having conductivity or not.
- an oxide semiconductor and an organic substance can be given.
- the material illustrated to the light emitting layer, the positive hole injection layer, the positive hole transport layer, the electron carrying layer, or the electron injection layer is mentioned, for example.
- an inorganic carbon-based material or a metal thin film that transmits light can be used, and a plurality of layers of several nm to several tens of nm may be stacked.
- the electrode 101 or the electrode 102 has a function as a cathode, it is preferable to use a material having a low work function (3.8 eV or less).
- a material having a low work function 3.8 eV or less.
- elements belonging to Group 1 or Group 2 of the periodic table alkali metals such as lithium, sodium and cesium, alkaline earth metals such as calcium and strontium, magnesium and the like
- alloys containing these elements for example, Ag And rare earth metals such as Mg, Al and Li
- europium (Eu) and Yb alloys containing these rare earth metals, alloys containing aluminum and silver, and the like can be used.
- the electrode 101 or the electrode 102 is used as an anode, it is preferable to use a material having a large work function (4.0 eV or more).
- the electrode 101 and the electrode 102 may be a stack of a conductive material having a function of reflecting light and a conductive material having a function of transmitting light. In that case, the electrode 101 and the electrode 102 are preferable because they can have a function of adjusting an optical distance so that light having a desired wavelength from each light-emitting layer can resonate and light having a desired wavelength can be strengthened. .
- a sputtering method As a method for forming the electrode 101 and the electrode 102, a sputtering method, a vapor deposition method, a printing method, a coating method, an MBE (Molecular Beam Epitaxy) method, a CVD method, a pulse laser deposition method, an ALD (Atomic Layer Deposition) method, or the like is appropriately used. be able to.
- the light-emitting element according to one embodiment of the present invention may be manufactured over a substrate formed of glass, plastic, or the like. As the order of manufacturing on the substrate, the layers may be sequentially stacked from the electrode 101 side or may be sequentially stacked from the electrode 102 side.
- the substrate over which the light-emitting element according to one embodiment of the present invention can be formed glass, quartz, plastic, or the like can be used, for example.
- a flexible substrate may be used.
- the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate and polyarylate.
- a film, an inorganic vapor deposition film, etc. can also be used.
- other materials may be used as long as they function as a support in the manufacturing process of the light-emitting element and the optical element. Or what is necessary is just to have a function which protects a light emitting element and an optical element.
- a light emitting element can be formed using various substrates.
- substrate is not specifically limited.
- the substrate include a semiconductor substrate (for example, a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having stainless steel foil, and a tungsten substrate.
- the glass substrate include barium borosilicate glass, aluminoborosilicate glass, and soda lime glass.
- Examples of a flexible substrate, a laminated film, a base film and the like include the following.
- plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), and polytetrafluoroethylene (PTFE).
- PET polyethylene terephthalate
- PEN polyethylene naphthalate
- PES polyethersulfone
- PTFE polytetrafluoroethylene
- Another example is a resin such as acrylic.
- examples include polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride.
- polyamide, polyimide, aramid, epoxy, an inorganic vapor deposition film, papers, and the like are examples of the like.
- a flexible substrate may be used as the substrate, and the light emitting element may be formed directly on the flexible substrate.
- a separation layer may be provided between the substrate and the light-emitting element.
- the release layer can be used to separate a part from the substrate after the light emitting element is partially or wholly formed thereon, and to transfer the light emitting element to another substrate. At that time, the light-emitting element can be transferred to a substrate having poor heat resistance or a flexible substrate.
- a structure of a laminated structure of an inorganic film of a tungsten film and a silicon oxide film or a structure in which a resin film such as polyimide is formed over a substrate can be used for the above-described release layer.
- a light emitting element may be formed using a certain substrate, and then the light emitting element may be transferred to another substrate, and the light emitting element may be disposed on another substrate.
- a substrate to which the light emitting element is transferred in addition to the above-described substrate, a cellophane substrate, a stone substrate, a wood substrate, a cloth substrate (natural fiber (silk, cotton, hemp), synthetic fiber (nylon, polyurethane, polyester) or There are recycled fibers (including acetate, cupra, rayon, recycled polyester), leather substrates, rubber substrates, and the like.
- a light-emitting element that is not easily broken, a light-emitting element with high heat resistance, a light-emitting element that is reduced in weight, or a light-emitting element that is thinned can be obtained.
- a field effect transistor FET
- the light-emitting element 150 may be formed on an electrode electrically connected to the FET. Accordingly, an active matrix display device in which driving of the light emitting element 150 is controlled by the FET can be manufactured.
- a material that can be used for the above light-emitting element can be used for the solar cell.
- the hole transport material and electron transport material described above are used for the carrier transport layer of the solar cell, and the hole transport material, electron transport material, light emitting material, silicon, and CH 3 NH 3 PbI are used for the photovoltaic layer.
- Perovskite crystals represented by 3 can be used.
- the material which can be used for the above-mentioned light emitting element can be used also regarding a board
- Embodiment 2 a light-emitting element having a structure different from that of the light-emitting element described in Embodiment 1 and a light-emitting mechanism of the light-emitting element will be described below with reference to FIGS. 3 and 4, portions having the same functions as those shown in FIG. 2A have the same hatch pattern, and the symbols may be omitted. Moreover, the same code
- FIG. 3A is a schematic cross-sectional view of the light-emitting element 250.
- a light-emitting element 250 illustrated in FIG. 3A includes a plurality of light-emitting units (the light-emitting unit 106 and the light-emitting unit 108 in FIG. 3A) between a pair of electrodes (the electrode 101 and the electrode 102). Note that in the light-emitting element 250, the electrode 101 functions as an anode and the electrode 102 functions as a cathode, but the structure of the light-emitting element 250 may be reversed.
- the light-emitting unit 106 and the light-emitting unit 108 are stacked, and a charge generation layer 115 is provided between the light-emitting unit 106 and the light-emitting unit 108.
- the light emitting unit 106 and the light emitting unit 108 may have the same configuration or different configurations.
- the light emitting element 250 includes the light emitting layer 120 and the light emitting layer 170.
- the light emitting unit 106 includes a hole injection layer 111, a hole transport layer 112, an electron transport layer 113, and an electron injection layer 114.
- the light emitting unit 108 includes a hole injection layer 116, a hole transport layer 117, an electron transport layer 118, and an electron injection layer 119.
- the charge generation layer 115 has a configuration in which an acceptor substance that is an electron acceptor is added to a hole transport material, but a donor substance that is an electron donor is added to the electron transport material. May be. Moreover, both these structures may be laminated
- the charge generation layer 115 includes a composite material of an organic compound and an acceptor substance
- a composite material that can be used for the hole-injection layer 111 described in Embodiment 1 may be used as the composite material.
- the organic compound various compounds such as an aromatic amine compound, a carbazole compound, an aromatic hydrocarbon, and a high molecular compound (oligomer, dendrimer, polymer, etc.) can be used.
- a substance having a hole mobility of 1 ⁇ 10 ⁇ 6 cm 2 / Vs or higher is preferably used. However, any substance other than these substances may be used as long as it has a property of transporting more holes than electrons.
- the charge generation layer 115 can also serve as a hole injection layer or a hole transport layer of the light emission unit.
- the unit may not be provided with a hole injection layer or a hole transport layer.
- the charge generation layer 115 can also serve as an electron injection layer or an electron transport layer of the light emission unit. May have a configuration in which an electron injection layer or an electron transport layer is not provided.
- the charge generation layer 115 may be formed as a stacked structure in which a layer including a composite material of an organic compound and an acceptor substance and a layer formed using another material are combined.
- a layer including a composite material of an organic compound and an acceptor substance may be formed in combination with a layer including one compound selected from electron donating substances and a compound having a high electron transporting property.
- a layer including a composite material of an organic compound and an acceptor substance may be combined with a layer including a transparent conductive film.
- the charge generation layer 115 sandwiched between the light-emitting unit 106 and the light-emitting unit 108 injects electrons into one light-emitting unit and applies holes to the other light-emitting unit when voltage is applied to the electrode 101 and the electrode 102. As long as it injects. For example, in FIG. 3A, when a voltage is applied so that the potential of the electrode 101 is higher than the potential of the electrode 102, the charge generation layer 115 injects electrons into the light-emitting unit 106, and the light-emitting unit 108. Inject holes into
- the charge generation layer 115 preferably has a property of transmitting visible light (specifically, the transmittance of visible light to the charge generation layer 115 is 40% or more) from the viewpoint of light extraction efficiency.
- the charge generation layer 115 functions even when it has lower conductivity than the pair of electrodes (the electrode 101 and the electrode 102).
- the present invention can be similarly applied to a light-emitting element in which three or more light-emitting units are stacked.
- a plurality of light-emitting units are partitioned between a pair of electrodes by a charge generation layer, thereby enabling high-intensity light emission while maintaining a low current density, and a longer-life light-emitting element Can be realized.
- a light-emitting element with low power consumption can be realized.
- the light emission colors exhibited by the guest materials used for the light-emitting unit 106 and the light-emitting unit 108 may be the same as or different from each other.
- the light-emitting element 250 is preferably a light-emitting element that exhibits high luminance with a small current value.
- the light-emitting element 250 is preferably a light-emitting element that emits multicolor light.
- the emission spectrum of the light emitting element 250 is combined with light having light emission having different light emission peaks. Therefore, the emission spectrum has at least two maximum values.
- White light emission can be obtained by making the lights of the light emitting layer 120 and the light emitting layer 170 complementary colors.
- the emission colors exhibited by the guest materials used in the respective light-emitting units may be the same or different from each other.
- the light emission colors exhibited by the plurality of light emitting units can achieve high light emission luminance with a smaller current value than other colors.
- Such a configuration can be suitably used for adjusting the emission color.
- it is suitable when using guest materials that have different luminous efficiencies and exhibit different luminescent colors.
- the emission intensity of phosphorescence can be adjusted. That is, the intensity of the emitted color can be adjusted by the number of light emitting units.
- a light emitting device containing two layers of light emitting units containing a blue fluorescent material and one layer of light emitting units containing a yellow phosphorescent material or blue
- a light-emitting element having one light-emitting layer unit containing a material is preferable because white light emission can be efficiently obtained.
- At least one of the light emitting layer 120 or the light emitting layer 170 may be further divided into layers, and a different light emitting material may be included in each of the divided layers. That is, at least one of the light-emitting layer 120 or the light-emitting layer 170 can also be configured by a plurality of two or more layers. For example, the first light-emitting layer and the second light-emitting layer are sequentially stacked from the hole transport layer side. When the light emitting layer is used, a material having a hole transporting property is used as the host material of the first light emitting layer, and a material having an electron transporting property is used as the host material of the second light emitting layer.
- the light emitting materials included in the first light emitting layer and the second light emitting layer may be the same material or different materials, and may be different materials that have the function of emitting light of the same color.
- a material having a function of emitting light of a color may be used.
- white light emission having high color rendering properties composed of three primary colors or four or more light emission colors can be obtained.
- Embodiment 1 by applying the structure described in Embodiment 1 to at least one of the plurality of units, a light-emitting element with high light extraction efficiency and reduced driving voltage can be provided.
- the light-emitting layer 120 included in the light-emitting unit 108 includes a guest material 121 and a host material 122 as illustrated in FIG.
- the guest material 121 will be described below as a fluorescent material.
- Light-Emitting Mechanism of Light-Emitting Layer 120 >> The light emission mechanism of the light emitting layer 120 will be described below.
- Excitons are generated by recombination of electrons and holes injected from the pair of electrodes (electrode 101 and electrode 102) or the charge generation layer 115 in the light emitting layer 120. Since the host material 122 is present in a large amount compared to the guest material 121, the excited state of the host material 122 is almost formed by the generation of excitons.
- An exciton is a carrier (electron and hole) pair.
- the singlet excitation energy is transferred from the S1 level of the host material 122 to the S1 level of the guest material 121, and the singlet excitation of the guest material 121 is performed. A state is formed.
- the guest material 121 is a fluorescent material, the guest material 121 emits light quickly when a singlet excited state is formed in the guest material 121. At this time, in order to obtain high luminous efficiency, the guest material 121 preferably has a high fluorescence quantum yield. Note that the same applies to the guest material 121 in which carriers are recombined and the generated excited state is a singlet excited state.
- FIG. 3C shows the correlation between energy levels of the host material 122 and the guest material 121 in this case.
- the notations and symbols in FIG. 3C are as follows. Note that since the T1 level of the host material 122 is preferably lower than the T1 level of the guest material 121, FIG. 3C illustrates this case, but the T1 level of the host material 122 is higher than that of the guest material 121. It may be higher than the T1 level.
- triplet-triplet annihilation causes triplet excitons generated by carrier recombination to interact with each other, exchange excitation energy with each other, and by the exchange of spin angular momentum, resulting in S1 level position of the host material 122 reactions to be converted to singlet excitons having an energy of (S FH) is caused (see FIG. 3 (C) TTA).
- the singlet excitation energy of the host material 122 causes energy transfer from S FH to the S1 level (S FG ) of the guest material 121 having lower energy (see FIG. 3C, route E 1 ).
- a singlet excited state of 121 is formed, and the guest material 121 emits light.
- the density of triplet excitons in the light emitting layer 120 is sufficiently high (for example, 1 ⁇ 10 12 cm ⁇ 3 or more), the inactivation of the singlet excitons alone is ignored, and two adjacent triplet excitations are performed. Only the reaction by the child can be considered.
- T FH T1 level position of the host material 122
- T FG T1 level position of the guest material 121
- T FG T1 level position of the guest material 121
- the host material 122 preferably has a function of converting triplet excitation energy to singlet excitation energy by TTA. By doing so, part of the triplet excitation energy generated in the light-emitting layer 120 is converted into singlet excitation energy by TTA in the host material 122, and the singlet excitation energy is transferred to the guest material 121, whereby fluorescence It can be extracted as light emission.
- the S1 level (S FH ) of the host material 122 is preferably higher than the S1 level (S FG ) of the guest material 121.
- the T1 level (T FH ) of the host material 122 is preferably lower than the T1 level (T FG ) of the guest material 121.
- the weight ratio of the host material 122 to the guest material 121 is as follows. A lower weight ratio is preferred. Specifically, the weight ratio of the guest material 121 when the host material 122 is 1 is preferably greater than 0 and 0.05 or less. By doing so, the probability that carriers are recombined in the guest material 121 can be reduced. In addition, the probability of energy transfer from the T1 level (T FH ) of the host material 122 to the T1 level (T FG ) of the guest material 121 can be reduced.
- the host material 122 may be composed of a single compound or a plurality of compounds.
- the light emission from the light emitting layer 120 has a light emission peak on the shorter wavelength side than the light emission from the light emitting layer 170. Is preferred.
- a light-emitting element using a material having a high triplet excitation energy level tends to deteriorate in luminance.
- TTA for the light-emitting layer that emits light with a short wavelength, a light-emitting element with low luminance deterioration can be provided.
- FIG. 4A is a schematic cross-sectional view of the light-emitting element 252.
- a light-emitting element 252 illustrated in FIG. 4A has a plurality of light-emitting units (in FIG. 4A) between a pair of electrodes (the electrode 101 and the electrode 102), similarly to the light-emitting element 250 described above.
- the light-emitting unit 106 and the light-emitting unit 110 are stacked, and a charge generation layer 115 is provided between the light-emitting unit 106 and the light-emitting unit 110.
- the EL layer 100 is preferably used for the light-emitting unit 106.
- the light emitting element 252 includes a light emitting layer 140 and a light emitting layer 170.
- the light emitting unit 106 includes a hole injection layer 111, a hole transport layer 112, an electron transport layer 113, and an electron injection layer 114.
- the light emitting unit 110 includes a hole injection layer 116, a hole transport layer 117, an electron transport layer 118, and an electron injection layer 119.
- Embodiment 1 by applying the structure described in Embodiment 1 to at least one of the plurality of units, a light-emitting element with high light extraction efficiency and reduced driving voltage can be provided.
- the light emitting layer 140 included in the light emitting unit 110 includes a guest material 141 and a host material 142 as shown in FIG.
- the host material 142 includes an organic compound 142_1 and an organic compound 142_2. Note that the guest material 141 included in the light-emitting layer 140 is described below as a phosphorescent material.
- the organic compound 142_1 and the organic compound 142_2 included in the light-emitting layer 140 form an exciplex.
- the combination of the organic compound 142_1 and the organic compound 142_2 may be any combination that can form an exciplex with each other, but one is a compound having a hole transporting property and the other is a compound having an electron transporting property. More preferably.
- FIG. 4C illustrates the correlation of energy levels among the organic compound 142_1, the organic compound 142_2, and the guest material 141 in the light-emitting layer 140.
- symbol in FIG.4 (C) are as follows.
- the organic compound 142_1 and the organic compound 142_2 form an exciplex, and the S1 level (S PE ) and the T1 level (T PE ) of the exciplex are adjacent to each other (FIG. 4C, route E 3 reference).
- One of the organic compound 142_1 and the organic compound 142_2 receives a hole and the other receives an electron, so that an exciplex is quickly formed.
- an exciplex is quickly formed.
- the excitation energy level (S PE or T PE ) of the exciplex is lower because it is lower than the S1 level (S PH1 and S PH2 ) of the host material (organic compound 142_1 and organic compound 142_2) that forms the exciplex.
- the excited state of the host material 142 can be formed with the excitation energy. As a result, the driving voltage of the light emitting element can be lowered.
- the T1 level (T PE ) of the exciplex is preferably larger than the T1 level (T PG ) of the guest material 141.
- the singlet excitation energy and triplet excitation energy of the generated exciplex are changed from the S1 level (S PE ) and T1 level (T PE ) of the exciplex to the T1 level (T PG ) of the guest material 141. ) To transfer energy.
- the T1 level (T PE ) of the exciplex corresponds to each organic compound (organic compound 142_1 and organic compound 142_2) that forms the exciplex. It is preferable that it is equal to or smaller than the T1 level ( TPH1 and TPH2 ). Accordingly, quenching of the triplet excitation energy of the exciplex by each organic compound (organic compound 142_1 and organic compound 142_2) is difficult to occur, and energy transfer from the exciplex to the guest material 141 is efficiently generated.
- one of the organic compounds 142_1 and 142_2 has a higher HOMO level than the other HOMO level, and one LUMO level. Is preferably higher than the other LUMO level.
- the HOMO level of the organic compound 142_1 is preferably higher than the HOMO level of the organic compound 142_2.
- the LUMO level is preferably higher than the LUMO level of the organic compound 142_2.
- the HOMO level of the organic compound 142_2 is preferably higher than the HOMO level of the organic compound 142_1.
- the LUMO level is preferably higher than the LUMO level of the organic compound 142_1.
- the energy difference between the HOMO level of the organic compound 142_1 and the HOMO level of the organic compound 142_2 is preferably 0.05 eV or more, more preferably 0.1 eV or more, and still more preferably 0.8. 2 eV or more.
- the energy difference between the LUMO level of the organic compound 142_1 and the LUMO level of the organic compound 142_2 is preferably 0.05 eV or more, more preferably 0.1 eV or more, and further preferably 0.2 eV or more. is there.
- the light emitting layer 140 has the above-described structure, light emission from the guest material 141 (phosphorescent material) of the light emitting layer 140 can be efficiently obtained.
- the processes of the routes E 3 to E 5 described above may be referred to as ExTET (Exciplex-Triple Energy Transfer) in this specification and the like.
- the light-emitting layer 140 has a supply of excitation energy from the exciplex to the guest material 141. Note that this is not necessarily the reverse intersystem crossing efficiency from T PE to S PE is high when, because there is no great need emission quantum yield from S PE, it is possible to widely select a material.
- the light emission from the light emitting layer 170 has a light emission peak on the shorter wavelength side than the light emission from the light emitting layer 140.
- a light-emitting element using a phosphorescent material that emits light having a short wavelength tends to deteriorate in luminance. Therefore, a light-emitting element with small luminance deterioration can be provided by using short-wavelength light emission as fluorescent light emission.
- the host material 122 is present in the largest amount by weight, and the guest material 121 (fluorescent material) is dispersed in the host material 122.
- the S1 level of the host material 122 is higher than the S1 level of the guest material 121 (fluorescent material), and the T1 level of the host material 122 is preferably lower than the T1 level of the guest material 121 (fluorescent material). .
- the guest material 121 is not particularly limited, but anthracene derivatives, tetracene derivatives, chrysene derivatives, phenanthrene derivatives, pyrene derivatives, perylene derivatives, stilbene derivatives, acridone derivatives, coumarin derivatives, phenoxazine derivatives, phenothiazine derivatives.
- the fluorescent compound shown in Embodiment Mode 1 can be preferably used.
- a material that can be used for the host material 122 in the light-emitting layer 120 for example, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-) 8-quinolinolato) aluminum (III) (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq 2 ), bis (2-methyl-8-quinolinolato) (4- Phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation) : ZnPBO), gold such as bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ)
- condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo [g, p] chrysene derivatives can be given.
- the light emitting layer 120 can also be comprised by two or more layers.
- a substance having a hole-transport property is used as the host material of the first light-emitting layer
- a substance having an electron transporting property is used as a host material of the second light emitting layer.
- the host material 122 may be composed of one kind of compound or a plurality of compounds.
- the light-emitting layer 120 may include a material other than the host material 122 and the guest material 121.
- the host material 142 is present in the largest amount by weight, and the guest material 141 (phosphorescent material) is dispersed in the host material 142.
- the T1 level of the host material 142 (the organic compound 142_1 and the organic compound 142_2) of the light-emitting layer 140 is preferably higher than the T1 level of the guest material 141.
- Examples of the organic compound 142_1 include zinc and aluminum-based metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, Bipyridine derivatives, phenanthroline derivatives and the like can be mentioned.
- Other examples include aromatic amines and carbazole derivatives. Specifically, the electron transporting material and the hole transporting material described in Embodiment 1 can be used.
- the organic compound 142_2 a combination capable of forming an exciplex with the organic compound 142_1 is preferable.
- the electron transporting material and the hole transporting material described in Embodiment 1 can be used.
- the emission peak of the exciplex formed by the organic compound 142_1 and the organic compound 142_2 is an absorption band of the triplet MLCT (Metal to Ligand Charge Transfer) transition of the guest material 141 (phosphorescent material), more specifically,
- the organic compound 142_1, the organic compound 142_2, and the guest material 141 (phosphorescent material) are preferably selected so as to overlap with the absorption band on the longest wavelength side. Thereby, it can be set as the light emitting element which luminous efficiency improved greatly.
- the absorption band on the longest wavelength side is a singlet absorption band.
- Examples of the guest material 141 include iridium, rhodium, or platinum-based organometallic complexes, or metal complexes.
- organic iridium complexes such as iridium-based orthometal complexes are preferable.
- Examples of orthometalated ligands include 4H-triazole ligands, 1H-triazole ligands, imidazole ligands, pyridine ligands, pyrimidine ligands, pyrazine ligands, and isoquinoline ligands.
- Examples of the metal complex include a platinum complex having a porphyrin ligand.
- the materials exemplified as the guest material 132 described in Embodiment 1 can be used.
- the light emitting material included in the light emitting layer 140 may be any material that can convert triplet excitation energy into light emission.
- Examples of the material capable of converting the triplet excitation energy into light emission include a thermally activated delayed fluorescent material in addition to the phosphorescent material. Therefore, the portion described as phosphorescent material may be read as thermally activated delayed fluorescent material.
- the material exhibiting thermally activated delayed fluorescence may be a material that can generate a singlet excited state from a triplet excited state by reverse intersystem crossing alone, or an exciplex (also referred to as an exciplex or exciplex). It may be composed of a plurality of materials that form
- thermally activated delayed fluorescent material is composed of one type of material, specifically, the thermally activated delayed fluorescent material shown in the first embodiment can be used.
- thermally activated delayed fluorescent material when used as a host material, it is preferable to use a combination of two types of compounds that form an exciplex. In this case, it is particularly preferable to use a compound that easily receives electrons, which is a combination that forms the exciplex shown above, and a compound that easily receives holes.
- Materials that can be used for light-emitting layer 170 are materials that can be used for the light-emitting layer 170.
- a material that can be used for the light-emitting layer described in Embodiment 1 may be used, so that a light-emitting element with high emission efficiency can be manufactured.
- the light emission color of the light emitting material contained in the light emitting layer 120, the light emitting layer 140, and the light emitting layer 170 is not limited, and may be the same or different. Since the light emission obtained from each is mixed and taken out of the device, the light emitting device can give white light when, for example, the light emission colors of both are complementary colors. In consideration of the reliability of the light emitting element, the emission peak wavelength of the light emitting material included in the light emitting layer 120 is preferably shorter than that of the light emitting material included in the light emitting layer 170.
- the light-emitting unit 106, the light-emitting unit 108, the light-emitting unit 110, and the charge generation layer 115 can be formed by a method such as an evaporation method (including a vacuum evaporation method), an inkjet method, a coating method, or gravure printing.
- a method such as an evaporation method (including a vacuum evaporation method), an inkjet method, a coating method, or gravure printing.
- FIG. 5A is a top view illustrating the light-emitting device
- FIG. 5B is a cross-sectional view taken along lines AB and CD of FIG. 5A.
- This light-emitting device includes a drive circuit portion (source side drive circuit) 601, a pixel portion 602, and a drive circuit portion (gate side drive circuit) 603 indicated by dotted lines, for controlling light emission of the light emitting element.
- Reference numeral 604 denotes a sealing substrate
- reference numeral 625 denotes a desiccant
- reference numeral 605 denotes a sealing material
- the inside surrounded by the sealing material 605 is a space 607.
- the routing wiring 608 is a wiring for transmitting a signal input to the source side driving circuit 601 and the gate side driving circuit 603, and a video signal, a clock signal, an FPC (flexible printed circuit) 609 serving as an external input terminal, Receives start signal, reset signal, etc.
- FPC flexible printed circuit
- a printed wiring board PWB: Printed Wiring Board
- the light-emitting device in this specification includes not only a light-emitting device body but also a state in which an FPC or a PWB is attached thereto.
- a driver circuit portion and a pixel portion are formed over the element substrate 610.
- a source side driver circuit 601 that is a driver circuit portion and one pixel in the pixel portion 602 are shown.
- the source side driver circuit 601 is a CMOS circuit in which an n-channel TFT 623 and a p-channel TFT 624 are combined.
- the driving circuit may be formed of various CMOS circuits, PMOS circuits, and NMOS circuits.
- CMOS circuits complementary metal-oxide-semiconductor circuits
- PMOS circuits PMOS circuits
- NMOS circuits CMOS circuits
- a driver integrated type in which a driver circuit is formed over a substrate is shown; however, this is not necessarily required, and the driver circuit can be formed outside the substrate.
- the pixel portion 602 is formed of a pixel including a switching TFT 611, a current control TFT 612, and a first electrode 613 electrically connected to the drain thereof. Note that an insulator 614 is formed so as to cover an end portion of the first electrode 613.
- the insulator 614 can be formed using a positive photosensitive resin film.
- a surface having a curvature is formed at the upper end portion or the lower end portion of the insulator 614.
- photosensitive acrylic is used as a material for the insulator 614
- the curvature radius of the curved surface is preferably 0.2 ⁇ m or more and 0.3 ⁇ m or less.
- the insulator 614 either a negative photosensitive material or a positive photosensitive material can be used.
- An EL layer 616 and a second electrode 617 are formed over the first electrode 613.
- a material used for the first electrode 613 functioning as an anode a material having a high work function is preferably used.
- a stack of a titanium nitride film and a film containing aluminum as a main component, a three-layer structure of a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film can be used. Note that with a stacked structure, resistance as a wiring is low, good ohmic contact can be obtained, and a function as an ano
- the EL layer 616 is formed by various methods such as an evaporation method using an evaporation mask, an inkjet method, and a spin coating method.
- the material forming the EL layer 616 may be a low molecular compound or a high molecular compound (including an oligomer and a dendrimer).
- the second electrode 617 formed over the EL layer 616 and functioning as a cathode a material having a low work function (Al, Mg, Li, Ca, or an alloy or compound thereof, MgAg, MgIn, AlLi or the like is preferably used.
- the second electrode 617 includes a thin metal film and a transparent conductive film (ITO, 2 wt% or more and 20 wt% or less).
- ITO transparent conductive film
- ZnO zinc oxide
- the light-emitting element 618 is formed by the first electrode 613, the EL layer 616, and the second electrode 617.
- the light-emitting element 618 is preferably a light-emitting element having the structure of Embodiments 1 and 2. Note that a plurality of light-emitting elements are formed in the pixel portion. However, in the light-emitting device in this embodiment, the light-emitting element having the structure described in Embodiments 1 and 2 and other structures are used. Both of the light emitting elements having the above may be included.
- the sealing substrate 604 is attached to the element substrate 610 with the sealant 605, whereby the light-emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. Yes.
- the space 607 is filled with a filler and may be filled with an inert gas (nitrogen, argon, or the like), or may be filled with a resin or a desiccant, or both.
- an epoxy resin or glass frit is preferably used for the sealant 605. Moreover, it is desirable that these materials are materials that do not transmit moisture and oxygen as much as possible.
- a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as a material used for the sealing substrate 604.
- FIG. 6 illustrates an example of a light emitting device in which a light emitting element that emits white light is formed and a colored layer (color filter) is formed as an example of the light emitting device.
- FIG. 6A shows a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, and a pixel portion.
- 1040, a driving circuit portion 1041, a first electrode 1024W, 1024R, 1024G, and 1024B of a light emitting element, a partition wall 1026, an EL layer 1028, a second electrode 1029 of the light emitting element, a sealing substrate 1031, a sealing material 1032, and the like are illustrated. ing.
- colored layers are provided over a transparent base material 1033.
- a black layer (black matrix) 1035 may be further provided.
- the transparent base material 1033 provided with the coloring layer and the black layer is aligned and fixed to the substrate 1001. Note that the colored layer and the black layer are covered with an overcoat layer 1036.
- FIG. 6A there are a light emitting layer in which light is emitted outside without passing through the colored layer, and a light emitting layer in which light is emitted through the colored layer of each color and is transmitted through the colored layer. Since the light that does not pass is white, and the light that passes through the colored layer is red, blue, and green, an image can be expressed by pixels of four colors.
- FIG. 6B illustrates an example in which the red colored layer 1034R, the green colored layer 1034G, and the blue colored layer 1034B are formed between the gate insulating film 1003 and the first interlayer insulating film 1020.
- the coloring layer may be provided between the substrate 1001 and the sealing substrate 1031.
- a light-emitting device having a structure in which light is extracted to the substrate 1001 side where the TFT is formed (bottom emission type) is used.
- a structure in which light is extracted from the sealing substrate 1031 side (top-emission type).
- FIG. 10 A cross-sectional view of a top emission type light emitting device is shown in FIG.
- a substrate that does not transmit light can be used as the substrate 1001.
- the connection electrode for connecting the TFT and the anode of the light emitting element is manufactured, it is formed in the same manner as the bottom emission type light emitting device.
- a third interlayer insulating film 1037 is formed so as to cover the electrode 1022. This insulating film may play a role of planarization.
- the third interlayer insulating film 1037 can be formed using various other materials in addition to the same material as the second interlayer insulating film 1021.
- the first lower electrodes 1025W, 1025R, 1025G, and 1025B of the light emitting elements are anodes here, but may be cathodes.
- the lower electrodes 1025W, 1025R, 1025G, and 1025B are preferably reflective electrodes.
- the second electrode 1029 preferably has a function of reflecting light and a function of transmitting light.
- a microcavity structure be applied between the second electrode 1029 and the lower electrodes 1025W, 1025R, 1025G, and 1025B to have a function of amplifying light of a specific wavelength.
- the EL layer 1028 has a structure as described in Embodiment 2 and has an element structure in which white light emission can be obtained.
- the structure of the EL layer that can emit white light may be realized by using a plurality of light-emitting layers, a plurality of light-emitting units, or the like. .
- the configuration for obtaining white light emission is not limited to these.
- sealing can be performed with a sealing substrate 1031 provided with colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B).
- a black layer (black matrix) 1035 may be provided on the sealing substrate 1031 so as to be positioned between the pixels.
- the colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) or black layer (black matrix) may be covered with an overcoat layer.
- the sealing substrate 1031 is a light-transmitting substrate.
- full color display is performed with four colors of red, green, blue, and white
- the present invention is not particularly limited, and full color display may be performed with three colors of red, green, and blue. Further, full color display may be performed with four colors of red, green, blue, and yellow.
- one embodiment of the present invention is a light-emitting element using an organic EL
- a highly reliable electronic device having a flat surface and favorable light emission efficiency can be manufactured.
- a highly reliable electronic device having a curved surface and favorable emission efficiency can be manufactured.
- a highly reliable electronic device having flexibility and favorable light emission efficiency can be manufactured.
- Electronic devices include, for example, television devices, desktop or notebook personal computers, monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, personal digital assistants, audio devices Large game machines such as playback devices and pachinko machines are listed.
- the light-emitting device of one embodiment of the present invention can achieve high visibility regardless of the intensity of external light. Therefore, it can be suitably used for a portable electronic device, a wearable electronic device (wearable device), an electronic book terminal, and the like.
- a portable information terminal 900 illustrated in FIGS. 8A and 8B includes a housing 901, a housing 902, a display portion 903, a hinge portion 905, and the like.
- the housing 901 and the housing 902 are connected by a hinge portion 905.
- the portable information terminal 900 can be expanded from the folded state (FIG. 8A) as shown in FIG. 8B. Thereby, when carrying, it is excellent in portability, and when using, it is excellent in visibility by a large display area.
- the portable information terminal 900 is provided with a flexible display portion 903 across a housing 901 and a housing 902 connected by a hinge portion 905.
- a light-emitting device manufactured using one embodiment of the present invention can be used for the display portion 903. Thereby, a portable information terminal can be manufactured with a high yield.
- the display unit 903 can display at least one of document information, a still image, a moving image, and the like.
- the portable information terminal 900 can be used as an electronic book terminal.
- the display unit 903 When the portable information terminal 900 is deployed, the display unit 903 is held in a greatly curved form.
- the display portion 903 is held including a curved portion with a curvature radius of 1 mm to 50 mm, preferably 5 mm to 30 mm.
- Part of the display portion 903 can display a curved surface by continuously arranging pixels from the housing 901 to the housing 902.
- the display portion 903 functions as a touch panel and can be operated with a finger or a stylus.
- the display unit 903 is preferably composed of one flexible display. Accordingly, it is possible to perform continuous display without interruption between the housing 901 and the housing 902. Note that a display may be provided in each of the housing 901 and the housing 902.
- the hinge unit 905 preferably has a lock mechanism so that the angle between the housing 901 and the housing 902 does not become larger than a predetermined angle when the portable information terminal 900 is deployed.
- the angle at which the lock is applied is 90 degrees or more and less than 180 degrees, typically 90 degrees, 120 degrees, 135 degrees, 150 degrees, or 175 degrees. be able to. Thereby, the convenience, safety
- the hinge portion 905 has a lock mechanism
- the display portion 903 can be prevented from being damaged without applying excessive force to the display portion 903. Therefore, a highly reliable portable information terminal can be realized.
- the housing 901 and the housing 902 may include a power button, an operation button, an external connection port, a speaker, a microphone, and the like.
- One of the housing 901 and the housing 902 is provided with a wireless communication module, and transmits and receives data via a computer network such as the Internet, a LAN (Local Area Network), and Wi-Fi (registered trademark). Is possible.
- a computer network such as the Internet, a LAN (Local Area Network), and Wi-Fi (registered trademark). Is possible.
- a portable information terminal 910 illustrated in FIG. 8C includes a housing 911, a display portion 912, operation buttons 913, an external connection port 914, a speaker 915, a microphone 916, a camera 917, and the like.
- a light-emitting device manufactured using one embodiment of the present invention can be used for the display portion 912. Thereby, a portable information terminal can be manufactured with a high yield.
- the portable information terminal 910 includes a touch sensor in the display unit 912. All operations such as making a call or inputting characters can be performed by touching the display portion 912 with a finger or a stylus.
- the power can be turned on and off, and the type of the image displayed on the display unit 912 can be switched.
- the mail creation screen can be switched to the main menu screen.
- the orientation (portrait or landscape) of the portable information terminal 910 is determined, and the screen display orientation of the display unit 912 is determined. It can be switched automatically. The screen display orientation can also be switched by touching the display portion 912, operating the operation buttons 913, or inputting voice using the microphone 916.
- the portable information terminal 910 has one or more functions selected from, for example, a telephone, a notebook, an information browsing device, or the like. Specifically, it can be used as a smartphone.
- the portable information terminal 910 can execute various applications such as mobile phone, electronic mail, text browsing and creation, music playback, video playback, Internet communication, and games.
- a camera 920 illustrated in FIG. 8D includes a housing 921, a display portion 922, operation buttons 923, a shutter button 924, and the like.
- a removable lens 926 is attached to the camera 920.
- a light-emitting device manufactured using one embodiment of the present invention can be used for the display portion 922. Thereby, a camera can be manufactured with a high yield.
- the camera 920 is configured such that the lens 926 can be removed from the housing 921 and replaced, but the lens 926 and the housing 921 may be integrated.
- the camera 920 can capture a still image or a moving image by pressing the shutter button 924.
- the display portion 922 has a function as a touch panel and can capture an image by touching the display portion 922.
- the camera 920 can be separately attached with a strobe device, a view interface, and the like. Alternatively, these may be incorporated in the housing 921.
- 9A to 9E illustrate electronic devices. These electronic devices include a housing 9000, a display portion 9001, a speaker 9003, operation keys 9005 (including a power switch or an operation switch), a connection terminal 9006, and a sensor 9007 (force, displacement, position, speed, acceleration, angular velocity, rotation) Number, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell, or infrared) And a microphone 9008 and the like.
- operation keys 9005 including a power switch or an operation switch
- connection terminal 9006 includes a connection terminal 9006
- a sensor 9007 force, displacement, position, speed, acceleration, angular velocity, rotation
- Number distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell, or infrared
- a microphone 9008 and the like.
- a light-emitting device manufactured using one embodiment of the present invention can be favorably used for the display portion 9001. Thereby, an electronic device can be manufactured with a high yield.
- the electronic devices illustrated in FIGS. 9A to 9E can have a variety of functions. For example, a function for displaying various information (still images, moving images, text images, etc.) on the display unit, a touch panel function, a function for displaying a calendar, date or time, a function for controlling processing by various software (programs), Wireless communication function, function for connecting to various computer networks using the wireless communication function, function for transmitting or receiving various data using the wireless communication function, and reading and displaying the program or data recorded on the recording medium It can have a function of displaying on the section. Note that the functions of the electronic devices illustrated in FIGS. 9A to 9E are not limited to these, and may have other functions.
- FIG. 9A is a perspective view illustrating a wristwatch-type portable information terminal 9200
- FIG. 9B is a perspective view illustrating a wristwatch-type portable information terminal 9201.
- a portable information terminal 9200 illustrated in FIG. 9A can execute various applications such as a mobile phone, electronic mail, text browsing and creation, music playback, Internet communication, and computer games. Further, the display portion 9001 is provided with a curved display surface, and can perform display along the curved display surface. In addition, the portable information terminal 9200 can execute short-range wireless communication with a communication standard. For example, it is possible to talk hands-free by communicating with a headset capable of wireless communication. In addition, the portable information terminal 9200 includes a connection terminal 9006 and can directly exchange data with other information terminals via a connector. Charging can also be performed through the connection terminal 9006. Note that the charging operation may be performed by wireless power feeding without using the connection terminal 9006.
- a mobile information terminal 9201 illustrated in FIG. 9B is different from the mobile information terminal illustrated in FIG. 9A in that the display surface of the display portion 9001 is not curved.
- the external shape of the display portion of the portable information terminal 9201 is a non-rectangular shape (a circular shape in FIG. 9B).
- FIG. 9C to 9E are perspective views showing a foldable portable information terminal 9202.
- FIG. 9C is a perspective view of a state in which the portable information terminal 9202 is expanded
- FIG. 9D is a state in which the portable information terminal 9202 is expanded or changed from one of the folded state to the other.
- FIG. 9E is a perspective view of the portable information terminal 9202 folded.
- the portable information terminal 9202 is excellent in portability in the folded state, and in the expanded state, the portable information terminal 9202 is excellent in display listability due to a seamless wide display area.
- a display portion 9001 included in the portable information terminal 9202 is supported by three housings 9000 connected by a hinge 9055. By bending between the two housings 9000 via the hinge 9055, the portable information terminal 9202 can be reversibly deformed from the expanded state to the folded state. For example, the portable information terminal 9202 can be bent with a curvature radius of 1 mm to 150 mm.
- an electronic device or a lighting device having a light-emitting region having a curved surface can be realized.
- the light-emitting device to which the light-emitting element of one embodiment of the present invention is applied can also be used for lighting of a car, for example, lighting can be installed on a windshield, a ceiling, or the like.
- FIG. 10A shows a perspective view of one surface of the multi-function terminal 3500
- FIG. 10B shows a perspective view of the other surface of the multi-function terminal 3500.
- a display portion 3504 a camera 3506, an illumination 3508, and the like are incorporated in a housing 3502.
- the light-emitting device of one embodiment of the present invention can be used for the lighting 3508.
- the illumination 3508 functions as a surface light source by using the light-emitting device of one embodiment of the present invention. Therefore, unlike a point light source represented by LED (Light Emitting Diode), light emission with less directivity can be obtained. For example, when the lighting 3508 and the camera 3506 are used in combination, the lighting 3508 can be turned on or blinked and an image can be captured by the camera 3506. Since the illumination 3508 has a function as a surface light source, it can capture a photograph taken under natural light.
- LED Light Emitting Diode
- multi-function terminal 3500 illustrated in FIGS. 10A and 10B can have various functions similar to the electronic devices illustrated in FIGS. 9A to 9C.
- a speaker In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current are provided inside the housing 3502. , Voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared measurement function), microphone, and the like. Further, by providing a detection device having a sensor for detecting inclination such as a gyroscope and an acceleration sensor inside the multi-function terminal 3500, the orientation (vertical or horizontal) of the multi-function terminal 3500 is determined, and a display unit 3504 is provided. The screen display can be automatically switched.
- the display portion 3504 can also function as an image sensor. For example, personal authentication can be performed by touching the display portion 3504 with a palm or a finger and capturing a palm print, a fingerprint, or the like.
- personal authentication can be performed by touching the display portion 3504 with a palm or a finger and capturing a palm print, a fingerprint, or the like.
- a backlight that emits near-infrared light or a sensing light source that emits near-infrared light is used for the display portion 3504, finger veins, palm veins, and the like can be imaged. Note that the light-emitting device of one embodiment of the present invention may be applied to the display portion 3504.
- FIG. 10C is a perspective view of a crime prevention light 3600.
- the light 3600 includes an illumination 3608 outside the housing 3602, and the housing 3602 incorporates a speaker 3610 and the like.
- the light-emitting element of one embodiment of the present invention can be used for the lighting 3608.
- the light 3600 for example, light can be emitted by holding, holding, or holding the illumination 3608.
- an electronic circuit that can control a light emission method from the light 3600 may be provided inside the housing 3602.
- a circuit that can emit light once or intermittently a plurality of times may be used, or a circuit that can adjust the light emission amount by controlling the light emission current value. Good.
- a circuit that outputs a loud alarm sound from the speaker 3610 at the same time as the light emission of the illumination 3608 may be incorporated.
- the light 3600 can emit light in all directions, for example, it can be threatened with light or light and sound toward a thief or the like. Further, the light 3600 may be provided with a camera such as a digital still camera so that a function having a photographing function may be provided.
- a camera such as a digital still camera
- FIG. 11 shows an example in which a light-emitting element is used as an indoor lighting device 8501.
- the light-emitting element can have a large area, a large-area lighting device can be formed.
- the lighting device 8502 in which the light-emitting region has a curved surface can be formed.
- the light-emitting element described in this embodiment is thin and has a high degree of freedom in housing design. Therefore, it is possible to form a lighting device with various designs.
- a large lighting device 8503 may be provided on the indoor wall surface.
- the lighting devices 8501, 8502, and 8503 may be provided with touch sensors to turn the power on or off.
- illuminating device 8504 provided with the function as a table by using a light emitting element for the surface side of a table.
- a lighting device having a function as furniture can be obtained by using a light-emitting element as part of other furniture.
- a lighting device and an electronic device can be obtained by using the light-emitting device of one embodiment of the present invention.
- applicable lighting devices and electronic devices are not limited to those described in this embodiment and can be applied to electronic devices in various fields.
- a manufacturing example of a light-emitting element which is a kind of the electronic device according to one embodiment of the present invention and characteristics of the light-emitting element will be described.
- the refractive index of the organic compound used for the hole injection layer and the refractive index of the hole injection layer will be described.
- a cross-sectional view of the element structure manufactured in this embodiment is shown in FIG. Details of the element structure are shown in Table 1. The structures and abbreviations of the compounds used are shown below.
- the organic compound used for the hole injection layer 111 of the comparative light emitting element 1 to the comparative light emitting element 4, the light emitting element 5 to the light emitting element 8, and the light emitting elements 9 to 12 and the refractive index of the hole injection layer 111 were measured.
- the refractive index is J.I. A.
- the measurement was performed at room temperature using a Woolam rotation compensator type multi-incidence angle high-speed spectroscopic ellipsometer (M-2000U). A measurement sample was produced on a quartz substrate by a vacuum deposition method. n Original and n Extraordinary were measured, and n average was calculated.
- the hole injection layer 111 since the hole injection layer 111 is required to have a hole injection property, the hole injection layer 111 preferably includes an electron donating material.
- the hole injection layer 111 of each light emitting device using MoO 3 having a high refractive index as an electron donating material is expected to have a high refractive index.
- the refractive index of the film obtained by adding MoO 3 as the hole injection layer 111 of each light emitting element to each organic compound is slightly higher than the refractive index of each organic compound. I understood.
- the hole injection layer 111 having a low refractive index can be obtained even when a material having a high refractive index is used as the material having an electron donating property. It was.
- FIG. 12 shows that the hole injection layer 111 of each light-emitting element has a smaller difference between n Original and n Extraordinary than each organic compound film. That is, it was found that the mixed film of MoO 3 that is an electron-accepting material and an organic compound has lower anisotropy than the organic compound film.
- DBT3P-II 1,3,5-tri- (4-dibenzothiophenyl) -benzene
- MoO 3 1,3,5-tri- (4-dibenzothiophenyl) -benzene
- DBT3P— II: MoO 3 a weight ratio
- the value of x 1 is different for each light-emitting element, the value of x 1 in the light-emitting elements is a value shown in Table 2.
- PCCP was deposited as a hole transport layer 112 on the hole injection layer 111 so as to have a thickness of 20 nm.
- 4,6mCzP2Pm, PCCP and Ir (pbi-diBuCNp) 3 are used as the light emitting layer 130 (1) on the hole transport layer 112 in a weight ratio (4 , 6mCzP2Pm: PCCP: Ir (pbi-diBuCNp) 3 ) is 0.5: 0.5: 0.1, and is co-evaporated to a thickness of 20 nm, and then the light emitting layer 130 (2 ) Was co-evaporated so that the weight ratio (4,6mCzP2Pm: PCCP: Ir (pbi-diBuCNp) 3 ) was 0.8: 0.2: 0.1 and the thickness was 20 nm.
- Ir (pbi-diBuCNp) 3 is a guest material that emits phosphorescence.
- 4,6 mCzP2Pm was co-deposited on the light emitting layer 130 (2) as the first electron transporting layer 118 (1) so as to have a thickness of 20 nm.
- bathophenanthroline abbreviation: BPhen
- BPhen bathophenanthroline
- lithium fluoride (LiF) was deposited as an electron injection layer 119 on the second electron transport layer 118 (2) so as to have a thickness of 1 nm.
- Al aluminum
- a glass substrate for sealing using an organic EL sealing material is fixed to a glass substrate on which an organic material is formed, so that the comparative light-emitting element 1 to the comparative light-emitting element are used. 4 was sealed. Specifically, a sealing material is applied around the organic material on the glass substrate on which the organic material is formed, the substrate and the glass substrate for sealing are bonded, and ultraviolet light with a wavelength of 365 nm is applied to 6 J / Irradiated with cm 2 and heat-treated at 80 ° C. for 1 hour.
- or the comparative light emitting element 4 were obtained by the above process.
- dmCBP and MoO 3 are mixed so that the weight ratio (dmCBP: MoO 3 ) is 2: 0.5 and the thickness is 35 nm. deposited, followed by a DBT3P-II, and MoO 3, the weight ratio (DBT3P-II: MoO 3) is 2: to 0.5, and thickness were co-deposited so that x 2 nm .
- the value of x 2 varies depending on each light emitting element, and the value of x 2 in each light emitting element is a value shown in Table 3.
- the manufacturing steps of the light-emitting elements 9 to 12 are different from the manufacturing steps of the comparative light-emitting element 1 to the comparative light-emitting element 4 and the manufacturing steps of the hole injection layer 111, and the other steps are the same as those of the comparative light-emitting elements 1 to 4. The same was done.
- TAPC and MoO 3 are mixed so that the weight ratio (TAPC: MoO 3 ) is 2: 0.5 and the thickness is 35 nm. deposited, followed by a DBT3P-II, and MoO 3, the weight ratio (DBT3P-II: MoO 3) is 2: to 0.5, and thickness were co-deposited so that x 2 nm .
- the value of x 2 is different for each light-emitting element, the value of x 2 in the light-emitting elements is a value shown in Table 3.
- FIG. 13 shows current efficiency-luminance characteristics of the comparative light-emitting element 1, the light-emitting element 5, and the light-emitting element 9 among the manufactured light-emitting elements.
- FIG. 14 shows current density-voltage characteristics.
- FIG. 15 shows the external quantum efficiency-luminance characteristics. Note that the value of the external quantum efficiency shown in FIG. 15 is the external quantum efficiency when measured from the front direction with respect to the light-emitting element without performing viewing angle correction.
- the comparative light emitting element 1 is DBT3P-II
- the light emitting element 5 is dmCBP
- the light emitting element 9 is an element using TAPC.
- the comparative light-emitting element 1, the light-emitting element 5, and the light-emitting element 9 have equivalent current density-voltage characteristics. Therefore, it was found that even when an organic compound having a low refractive index was used for the hole injection layer 111, it had good hole injection characteristics.
- the comparative light-emitting element 1, the light-emitting element 5, and the light-emitting element 9 have a high current efficiency exceeding 100 cd / A and a high external quantum efficiency exceeding 30%.
- the light-emitting element 5 and the light-emitting element 9 using dmCBP and TAPC, which are organic compounds having a low refractive index, for the hole injection layer 111 are higher than the comparative light-emitting element 1 using DBT3P-II, which is a material having a high refractive index. Showed efficiency.
- emission spectra when current is supplied to the comparative light-emitting element 1, the light-emitting element 5, and the light-emitting element 9 at a current density of 25 mA / cm 2 are illustrated in FIGS.
- the emission spectra of the comparative light-emitting element 1, the light-emitting element 5, and the light-emitting element 9 have peaks near 515 nm and 550 nm, and Ir (pbi ⁇ ), which is a guest material included in the light-emitting layer 130.
- diBuCNp) 3 was found to be derived from luminescence.
- Table 4 shows element characteristics of the comparative light-emitting elements 1 to 4 and the light-emitting elements 5 to 12 in the vicinity of 1000 cd / m 2 .
- the external quantum efficiency shown in Table 4 indicates the external quantum efficiency after performing the viewing angle correction.
- Comparative Light-Emitting Element 1 to Comparative Light-Emitting Element 4 and Light-Emitting Element 5 to Light-Emitting Element 12 manufactured in this example show good driving voltage and light emission efficiency regardless of the structure of the hole injection layer 111. I understand that.
- FIG. 17 shows the relationship between the chromaticity x and the external quantum efficiency depending on the organic material used for each hole injection layer 111, using the values of each element shown in Table 4.
- the values of the comparative light emitting element 1 to the comparative light emitting element 4 are used for the data of the curve “DBT3P-II”
- the values of the light emitting elements 5 to 8 are used for the data of the curve “dmCBP”
- the values of the light-emitting elements 9 to 12 are used as the curve data.
- the refractive index differs depending on the organic compound used.
- the optical path length from the light emitting region of the light emitting element to the substrate changes.
- the external quantum efficiency also changes. Therefore, when evaluating the relationship between the refractive index of the hole injection layer 111 and the external quantum efficiency, it is necessary to adjust the optical path length in each light emitting element. It is difficult to finely adjust the thickness of the EL layer.
- the emission spectrum and chromaticity obtained from the light-emitting elements are also different.
- the emission spectra extracted from each light emitting element are considered to be the same. That is, when the same chromaticity is obtained from each light emitting element, it can be said that the optical path length from the light emitting region of each light emitting element to the substrate is the same. Therefore, by considering the relationship between the external quantum efficiency and chromaticity x or chromaticity y, the relationship between the refractive index of the hole injection layer 111 and the external quantum efficiency can be evaluated.
- the organic compound used for the hole injection layer 111 has a high refractive index in the order of DBT3P-II> dmCBP> TAPC. From FIG. 17, it was found that the lower the refractive index of the organic compound used for the hole injection layer 111, the higher the external quantum efficiency. This is because light attenuation due to the evanescent mode is reduced and light extraction efficiency is improved.
- the manufacturing steps of the light-emitting elements 13 to 18 are different from the manufacturing steps of the comparative light-emitting element 1 to the comparative light-emitting element 4 and the manufacturing steps of the hole injection layer 111 and the light-emitting layer 130, and the other steps are the same. The same operation as that of the light-emitting element 4 was performed.
- DBT3P-II and MoO 3 are mixed so that the weight ratio (DBT3P-II: MoO 3 ) is 3-y: y and the thickness is 40 nm. Co-deposited. Note that the value of y varies depending on each light emitting element, and the value of y in each light emitting element is a value shown in Table 6. Table 6 also shows the results of converting the weight ratio to the volume ratio of MoO 3 at the same time.
- 4,6 mCzP2Pm and PCCP and Ir (tBupppm) 3 as a light emitting layer 130 (1) on the hole transport layer 112 have a weight ratio (4,6 mCzP2Pm: PCCP: Ir (tBupppm) 3 ) of 0.5. : 0.5: 0.075, and co-evaporated to a thickness of 20 nm, and then, as the light emitting layer 130 (2), the weight ratio (4,6mCzP2Pm: PCCP: Ir (tBupppm) 3 ) Was 0.8: 0.2: 0.075 and the thickness was 20 nm. Note that in the light-emitting layer 130 (1) and the light-emitting layer 130 (2), Ir (tBupppm) 3 is a guest material that exhibits phosphorescence.
- FIG. 18 shows the relationship between the external quantum efficiency in the vicinity of 10,000 cd / m 2 of each element and the volume ratio of MoO 3 in the hole injection layer 111.
- the external quantum efficiency is as high as 24% to 26%. Then, it turns out that efficiency is falling. This is because in the region where the volume ratio of MoO 3 is larger than 0.3, it is affected by the electron accepting substance (MoO 3 ) having a large refractive index, and the refractive index of the hole injection layer 111 is large, so that the light extraction is performed. It is suggested that efficiency is decreasing.
- the volume ratio of MoO 3 is greater than 0 and less than or equal to 0.3
- the effect of the electron-accepting material (MoO 3 ) having a large refractive index is small, and the refractive index is smaller than the electron-accepting material (MoO 3 )
- the refractive index of the donating substance has a strong influence on the refractive index of the hole injection layer 111, it is suggested that the light extraction efficiency is good. That is, by volume ratio of MoO 3 hole-injection layer 111 is used in the 0.3 following concentrations greater than 0, it is possible to light extraction efficiency to produce good light-emitting element.
- Example 1 As an electronic device according to one embodiment of the present invention, a manufacturing example of a light-emitting element different from that in Example 1 and characteristics of the light-emitting element will be described. Further, the refractive index of the organic compound used for the hole injection layer 111 and the refractive index of the hole injection layer will be described. Details of the element structure are shown in Table 7. The structures and abbreviations of the compounds used are shown below. In addition, what is necessary is just to refer previous Example 1 about another organic compound.
- FIG. 19 shows that DBT3P-II used for the comparative light-emitting elements 19 to 22 has the highest refractive index.
- 9- [3- (9-Phenyl-9H-fluoren-9-yl) phenyl] -9H-carbazole (abbreviation: mCzFLP) used for the light-emitting elements 23 to 26 has a refractive index in which n Original is 1.75 or less. It was found to be an organic compound with a low rate.
- 4,4 ′-[bis (9-phenylfluoren-9-yl)]-triphenylamine (abbreviation: FLP2A) used for the light-emitting element 27 to the light-emitting element 30 has a refractive index in which n Original is 1.75 or less. It was found to be an organic compound with a low rate.
- the mixed film of mCzFLP or FLP2A and MoO 3 which is the hole injection layer 111 of the light-emitting elements 23 to 30 has the same refractive index as each organic compound, and comparative light emission.
- the refractive index is expected to be lower than that of the mixed film of DBT3P-II and MoO 3 that is the hole injection layer 111 of the element 19 to the comparative light emitting element 22.
- DBT3P-II and MoO 3 are mixed so that the weight ratio (DBT3P-II: MoO 3 ) is 2: 0.5 and the thickness is z 1 nm. Co-deposited so that Note that the value of z 1 varies depending on each light emitting element, and the value of z 1 in each light emitting element is a value shown in Table 8.
- 4,6 mCzP2Pm and PCCP and Ir (ppy) 3 as a light emitting layer 130 (1) on the hole transport layer 112 have a weight ratio (4,6mCzP2Pm: PCCP: Ir (ppy) 3 ) of 0.5. : 0.5: 0.1 and co-evaporated to a thickness of 20 nm, followed by a light emitting layer 130 (2) with a weight ratio (4,6mCzP2Pm: PCCP: Ir (ppy) 3 ) Was 0.8: 0.2: 0.1 and co-evaporated to a thickness of 20 nm.
- Ir (ppy) 3 is a guest material that exhibits phosphorescence.
- the manufacturing steps of the light-emitting elements 23 to 26 are different from the manufacturing steps of the comparative light-emitting element 19 to the comparative light-emitting element 22 and the manufacturing steps of the hole injection layer 111, and the other steps are the same as those of the comparative light-emitting element 19 to the comparative light-emitting element 22. The same was done.
- mCzFLP and MoO 3 are mixed so that the weight ratio (mCzFLP: MoO 3 ) is 2: 0.5 and the thickness is 35 nm. Vapor deposition was performed, and then DBT3P-II and MoO 3 were co-deposited so that the weight ratio (DBT3P-II: MoO 3 ) was 2: 0.5 and the thickness was z 2 nm. .
- the value of z 2 is different for each light-emitting element, the value of z 2 in the light-emitting elements is a value shown in Table 9.
- the weight ratio (FLP2A: MoO 3) is 2: to 0.5, as and thickness is 35nm co Vapor deposition was performed, and then DBT3P-II and MoO 3 were co-deposited so that the weight ratio (DBT3P-II: MoO 3 ) was 2: 0.5 and the thickness was z 2 nm. .
- the value of z 2 is different for each light-emitting element, the value of z 2 in the light-emitting elements is a value shown in Table 9.
- FIG. 20 shows current efficiency-luminance characteristics of the comparative light-emitting element 19, the light-emitting element 23, and the light-emitting element 27 among the manufactured light-emitting elements.
- FIG. 21 shows current density-voltage characteristics.
- FIG. 22 shows the external quantum efficiency-luminance characteristics. Note that the values of the external quantum efficiency shown in FIG. 22 are the external quantum efficiencies when measured from the front direction with respect to the light emitting element, without performing viewing angle correction.
- the comparative light emitting element 19 is an element using DBT3P-II
- the light emitting element 23 is mCzFLP
- the light emitting element 27 is an element using FLP2A. Are all the same device structure.
- FIG. 21 indicates that the comparative light-emitting element 19, the light-emitting element 23, and the light-emitting element 27 have equivalent current density-voltage characteristics. Therefore, as in Example 1, it was found that even when an organic compound having a low refractive index was used for the hole injection layer 111, it had good hole injection characteristics.
- the comparative light-emitting element 19, the light-emitting element 23, and the light-emitting element 27 have a high current efficiency of around 100 cd / A and a high external quantum efficiency of more than 25%.
- the light emitting element 23 and the light emitting element 27 using mCzFLP and FLP2A, which are organic compounds having a low refractive index are higher than the comparative light emitting element 19 using DBT3P-II, which is a material having a high refractive index. Showed efficiency.
- the emission spectra of the comparative light-emitting element 19, the light-emitting element 23, and the light-emitting element 27 have a peak near 518 nm, and Ir (ppy) 3 , which is a guest material included in the light-emitting layer 130. It was found to be derived from luminescence.
- Table 10 shows element characteristics of the comparative light-emitting element 19 to the comparative light-emitting element 22 and the light-emitting element 23 to the light-emitting element 30 in the vicinity of 1000 cd / m 2 .
- Comparative Light-Emitting Element 19 to Comparative Light-Emitting Element 22 and Light-Emitting Element 23 to Light-Emitting Element 30 manufactured in this example show good driving voltage and light emission efficiency regardless of the structure of the hole injection layer 111. I understand that.
- FIG. 24 shows the relationship between the chromaticity x and the external quantum efficiency by the organic material used for each hole injection layer 111 using the values of each element shown in Table 10.
- the values of the comparative light emitting element 19 to the comparative light emitting element 22 are used for the data of the curve “DBT3P-II”, and the values of the light emitting elements 23 to 26 are used for the data of the curve “mCzFLP”.
- the values of the light emitting element 27 to the light emitting element 30 were used for the curve data of “
- the organic compound used for the hole injection layer 111 has a higher refractive index in the order of DBT3P-II> mCzFLP> FLP2A. From FIG. 24, it was found that the external quantum efficiency was higher as the refractive index of the organic compound used in the hole injection layer 111 was lower as in Example 1. This is because light attenuation due to the evanescent mode is reduced and light extraction efficiency is improved.
- a manufacturing example of a light-emitting element which is a kind of the electronic device according to one embodiment of the present invention and characteristics of the light-emitting element will be described.
- the refractive index of the organic compound used for the hole injection layer and the refractive index of the hole injection layer will be described.
- a cross-sectional view of the element structure manufactured in this embodiment is shown in FIG. Details of the element structure are shown in Tables 11 to 14.
- the structure and abbreviation of the compound used may be referred to the above embodiment and examples.
- the hole injection layer 111 since the hole injection layer 111 is required to have a hole injection property, the hole injection layer 111 preferably includes an electron donating material.
- the hole injection layer 111 of each light emitting device using MoO 3 having a high refractive index as an electron donating material is expected to have a high refractive index.
- the refractive index of the film obtained by adding MoO 3 as the hole injection layer 111 of each light-emitting element to each organic compound is slightly higher than the refractive index of each organic compound. I understood.
- the hole injecting layer 111 having a low refractive index even when a material having a high refractive index is mixed with the material having the electron donating property. was found to be obtained.
- FIG. 25 shows that the hole injection layer 111 of each light-emitting element has a smaller difference between n Original and n Extraordinary than each organic compound film. That is, it was found that the mixed film of MoO 3 that is an electron donating material and an organic compound has lower anisotropy than the organic compound film.
- CzSi which is an organic compound used for the hole injection layer 111 of the light emitting elements 39 to 42
- UGH-2 which is an organic compound used for the hole injection layer 111 of the comparative light emitting elements 47 to 50
- the mixed film of MoO 3 has the same refractive index as that of each organic compound, and the refractive index is higher than that of the mixed film of DBT3P-II and MoO 3 which are the hole injection layers 111 of the comparative light-emitting elements 1 to 4. Expected to be low.
- An ITSO film having a thickness of 70 nm was formed as an electrode 101 on a glass substrate.
- the electrode area of the electrode 101 was 4 mm 2 (2 mm ⁇ 2 mm).
- DBT3P-II 1,3,5-tri- (4-dibenzothiophenyl) -benzene
- MoO 3 1,3,5-tri- (4-dibenzothiophenyl) -benzene
- DBT3P— II: MoO 3 a weight ratio
- the value of x 3 are different for each light-emitting element, the value of x 3 in each light-emitting element is a value shown in Table 13.
- PCCP was deposited as a hole transport layer 112 on the hole injection layer 111 so as to have a thickness of 20 nm.
- 4,6 mCzP2Pm and PCCP and Ir (ppy) 3 as a light emitting layer 130 (1) on the hole transport layer 112 have a weight ratio (4,6mCzP2Pm: PCCP: Ir (ppy) 3 ) of 0.5. : 0.5: 0.1 and co-evaporated to a thickness of 20 nm, followed by a light emitting layer 130 (2) with a weight ratio (4,6mCzP2Pm: PCCP: Ir (ppy) 3 ) Was 0.8: 0.2: 0.1 and co-evaporated to a thickness of 20 nm.
- Ir (ppy) 3 is a guest material that exhibits phosphorescence.
- 4,6 mCzP2Pm was co-deposited on the light emitting layer 130 (2) as the first electron transporting layer 118 (1) so as to have a thickness of 20 nm.
- bathophenanthroline abbreviation: BPhen
- BPhen bathophenanthroline
- lithium fluoride (LiF) was deposited as an electron injection layer 119 on the second electron transport layer 118 (2) so as to have a thickness of 1 nm.
- Al aluminum
- or the comparative light emitting element are fixed by fixing the glass substrate for sealing using the sealing material for organic EL in the glove box of nitrogen atmosphere to the glass substrate in which the organic material was formed. 34 was sealed. Specifically, a sealing material is applied around the organic material on the glass substrate on which the organic material is formed, the substrate and the glass substrate for sealing are bonded, and ultraviolet light with a wavelength of 365 nm is applied to 6 J / Irradiated with cm 2 and heat-treated at 80 ° C. for 1 hour.
- the comparative light emitting element 31 to the comparative light emitting element 34 were obtained through the above steps.
- FIG. 26 shows current efficiency-luminance characteristics of the comparative light emitting element 31, the light emitting element 35, the light emitting element 39, the light emitting element 43, and the comparative light emitting element 47 among the manufactured light emitting elements.
- FIG. 27 shows current density-voltage characteristics.
- FIG. 28 shows the external quantum efficiency-luminance characteristics. Note that the values of the external quantum efficiency shown in FIG. 28 are the external quantum efficiencies when measured from the front direction with respect to the light emitting element, without performing viewing angle correction.
- the comparative light emitting element 31 is DBT3P-II
- the light emitting element 35 is CzC
- the light emitting element 39 is CzSi
- the light emitting element 43 is FATPA
- the comparative light emitting element 47 is UGH-2.
- Each part except for the hole injection layer 111 has the same element structure.
- the comparative light emitting element 31, the light emitting element 35, the light emitting element 39, the light emitting element 43, and the comparative light emitting element 47 have a high current efficiency exceeding 90 cd / A and a high external quantum efficiency exceeding 25%. I found out.
- the light emitting element 35, the light emitting element 39, the light emitting element 43, and the comparative light emitting element 47 using an organic compound having a low refractive index for the hole injection layer 111 are comparative light emitting elements using DBT3P-II which is a material having a high refractive index. The efficiency was higher than 31. This suggests that the attenuation of light due to the evanescent wave is suppressed by using an organic compound having a low refractive index for the hole injection layer 111.
- the comparative light-emitting element 31 the light-emitting element 35, the light-emitting element 39, and the light-emitting element 43 have equivalent good current density-voltage characteristics.
- the comparative light-emitting element 47 had a lower current density-voltage characteristic and a lower hole injection property than the comparative light-emitting element 31, the light-emitting element 35, the light-emitting element 39, and the light-emitting element 43. This is because UGH-2 does not have an electron donating group in the molecule.
- the hole-injecting layer 111 having good hole-injecting characteristics can be manufactured even when a material having a low refractive index is used for the hole-injecting layer 111. It was.
- the emission spectra of the comparative light-emitting element 31, the light-emitting element 35, the light-emitting element 39, the light emitting element 43, and the comparative light-emitting element 47 have a peak near 518 nm, and the guest material included in the light-emitting layer 130 It was found that it originates from the luminescence of Ir (ppy) 3 .
- Table 15 shows element characteristics of the comparative light-emitting elements 31 to 34, the light-emitting elements 35 to 46, and the comparative light-emitting elements 47 to 50 in the vicinity of 1000 cd / m 2 .
- the external quantum efficiency shown in Table 15 indicates the external quantum efficiency after performing the viewing angle correction.
- the comparative light-emitting element 31 to comparative light-emitting element 34, the light-emitting element 35 to the light-emitting element 46, and the comparative light-emitting element 47 to the comparative light-emitting element 50 manufactured in this example have the same structure regardless of the structure of the hole injection layer 111. It can be seen that good drive voltage and luminous efficiency are exhibited.
- the comparative light emitting element 47 is used. This is probably because the hole-injection property is better than that of UGH-2. Therefore, it was found that the reliability of the light-emitting element is better when the hole injection property of the hole injection layer 111 is better.
- the reliability test results of the comparative light emitting element 31, the light emitting element 35, and the light emitting element 39 are overlapped.
- FIG. 31 shows the relationship between the chromaticity x and the external quantum efficiency depending on the organic material used for each hole injection layer 111, using the values of each element shown in Table 15.
- the values of the comparative light emitting element 31 to the comparative light emitting element 34 are used for the data of the curve “DBT3P-II”
- the values of the light emitting element 35 to the light emitting element 38 are used for the data of the curve “CzC”.
- the data of the light emitting elements 39 to 42 are compared to the data of the curve “
- the values of the light emitting elements 43 to 46 are compared to the data of the curve“ FATPA ”
- the data of the curve“ UGH-2 ” are compared.
- the values of the light emitting element 47 to the comparative light emitting element 50 were used.
- DBT3P-II which is an organic compound used for the hole injection layer 111 has a high refractive index exceeding 1.80, but CzC, CzSi, FATPA, UGH-2 has a refractive index. 1.
- the light emitting element using the organic compound having a low refractive index in the hole injection layer 111 has higher external quantum efficiency than the light emitting element using DBT3P-II in the hole injection layer 111. I understood. This is because light attenuation due to the evanescent mode is reduced and light extraction efficiency is improved.
- the light extraction efficiency is excellent while maintaining the hole injection characteristics. It was also found that a light-emitting element with good reliability can be obtained.
- a manufacturing example of a light-emitting element which is a kind of the electronic device according to one embodiment of the present invention and characteristics of the light-emitting element will be described.
- the refractive index of the organic compound used for the hole injection layer and the refractive index of the hole injection layer will be described.
- a cross-sectional view of the element structure manufactured in this embodiment is shown in FIG. Details of the element structure are shown in Table 16 and Table 17. The structures and abbreviations of the compounds used are shown below.
- the light-emitting element described in this example is formed using only an organic compound without using a metal oxide for the hole-injection layer 111.
- N, N, N ′, N′-tetra-naphthalen-2-yl-benzidine (abbreviation: ⁇ -TNB) and p-dopant (analytical workshop (analytical workshop)) used for the comparative light-emitting elements 51 to 54 are used. It was found that the mixed film of NPB and p-dopant used for the mixed film purchased from Co., Ltd.) and the comparative light emitting element 55 to comparative light emitting element 58 had a refractive index higher than 1.75 and a high refractive index.
- the refractive index of the BPAFLP / p-dopant mixed film used for the light-emitting elements 59 to 62 and the TAPC / p-dopant mixed film used for the light-emitting elements 63 to 66 has a refractive index of 1.75. Was found to have a lower and lower refractive index.
- An ITSO film having a thickness of 70 nm was formed as an electrode 101 on a glass substrate.
- the electrode area of the electrode 101 was 4 mm 2 (2 mm ⁇ 2 mm).
- the thickness of ⁇ -TNB and p-dopant is set so that the weight ratio ( ⁇ -TNB: p-dopant) is 1: 0.01.
- the weight ratio ( ⁇ -TNB: p-dopant) is 1: 0.01.
- PCBBiF was deposited as a hole transport layer 112 on the hole injection layer 111 so as to have a thickness of z 1 nm. Note that the value of z 1 varies depending on each light emitting element, and the value of z 1 in each light emitting element is a value shown in Table 17.
- 2mDBTBBPDBq-II, PCBBiF, and Ir (dppm) 2 (acac) as a light emitting layer 130 (1) on the hole transport layer 112 are weight ratios (2mDBTBBPDBq-II: PCBiF: Ir (dppm) 2 (acac)) is co-evaporated so that the thickness is 0.7: 0.3: 0.06 and the thickness is 20 nm.
- the light-emitting layer 130 (2) has a weight ratio (2mDBTBPDBq ⁇ II: PCBBiF: Ir (dppm) 2 (acac)) was co-evaporated so that the thickness was 0.8: 0.2: 0.06 and the thickness was 20 nm.
- Ir (dppm) 2 (acac) is a guest material that emits phosphorescence.
- 2mDBTBPDBq-II was co-deposited as a first electron transport layer 118 (1) on the light emitting layer 130 (2) so as to have a thickness of 20 nm.
- 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10- Phenanthroline (abbreviation: NBPhen) was deposited to a thickness of 20 nm.
- lithium fluoride (LiF) was deposited as an electron injection layer 119 on the second electron transport layer 118 (2) so as to have a thickness of 1 nm.
- Al aluminum
- a glass substrate for sealing using an organic EL sealing material is fixed to a glass substrate on which an organic material is formed, so that the comparative light-emitting element 51 to the comparative light-emitting element. 54 was sealed.
- a sealing material is applied around the organic material on the glass substrate on which the organic material is formed, the substrate and the glass substrate for sealing are bonded, and ultraviolet light with a wavelength of 365 nm is applied to 6 J / Irradiated with cm 2 and heat-treated at 80 ° C. for 1 hour.
- the comparative light emitting element 51 to the comparative light emitting element 54 were obtained through the above steps.
- Comparative Light-Emitting Element 51 to Comparative Light-Emitting Element 58 and Light-Emitting Element 59 to Light-Emitting Element 66 manufactured in this example show good driving voltage and light emission efficiency regardless of the structure of the hole injection layer 111. I understand that.
- FIG. 32 shows the relationship between the chromaticity y and the external quantum efficiency depending on the organic material used for each hole injection layer 111, using the values of each element shown in Table 19.
- the values of the comparative light emitting element 51 to the comparative light emitting element 54 are used for the data of the curve “ ⁇ -TNB”
- the values of the comparative light emitting element 55 to the comparative light emitting element 58 are used for the data of the curve “NPB”.
- the values of the light-emitting elements 59 to 62 are used for the data of the curve “BPAFLP”
- the values of the light-emitting elements 63 to 66 are used for the data of the curve “TAPC”.
- the refractive index of the hole injection layer 111 is a high refractive index exceeding 1.75, but when BPAFLP and TAPC are used, the refractive index is positive.
- the refractive index of the hole injection layer 111 is a low refractive index of 1.75 or less. From FIG. 32, for example, when comparing the external quantum efficiencies of the light emitting elements in the vicinity of the y chromaticity of 0.435, the light emitting element having the hole injection layer 111 having a low refractive index has a higher external quantum efficiency. I understood that.
- the light-emitting element having the hole injection layer 111 having a low refractive index at the same chromaticity has better light emission efficiency. This is because light attenuation due to the evanescent mode is reduced and light extraction efficiency is improved.
- Step 1 The synthesis scheme of Step 1 is shown in the following formula (a-1).
- Step 2 Synthesis of 4- [N- (2-nitrophenyl) amino] -3,5-diisobutylbenzonitrile> 4-amino-3,5-diisobutylbenzonitrile (30 g, 131 mmol) synthesized in Step 1, 86 g (263 mmol) of cesium carbonate, 380 mL of dimethyl sulfoxide (DMSO), 19 g (131 mmol) of 2-fluoronitrobenzene were placed in a 1000 mL three-necked flask. The mixture was stirred at 120 ° C. for 20 hours under a nitrogen stream. The reaction solution after elapse of a predetermined time was extracted with chloroform to obtain a crude product.
- DMSO dimethyl sulfoxide
- Step 3 Synthesis of 4- [N- (2-aminophenyl) amino] -3,5-diisobutylbenzonitrile>
- 21 g (60.0 mmol) of 4- [N- (2-nitrophenyl) amino] -3,5-diisobutylbenzonitrile synthesized in Step 2 11 mL (0.6 mol) of water, and 780 mL of ethanol were placed.
- 57 g (0.3 mol) of tin (II) chloride was added, and the mixture was stirred at 80 ° C. for 7.5 hours under a nitrogen stream.
Abstract
Description
本実施の形態では、本発明の一態様の電子デバイスについて、図1を用いて以下説明する。
電子デバイス50は、一対の基板(基板10及び基板15)間に一対の電極(電極11及び電極12)と有機半導体層20を有する。有機半導体層20は少なくとも、キャリア輸送層30と機能層40を有する。なお、有機半導体層20は機能層を複数有していても良い。
以下では、本発明の一態様の電子デバイスの一例である発光素子について、図2を用いて以下説明する。
ここで、正孔注入層111に好適に用いることができる有機化合物について説明する。
また、本発明の一態様である電子デバイスにおいて、光路長を制御することで、さらに光取出し効率を向上させることができる。発光層130から得られる発光のうち、所望の波長の光を効率良く取り出すことができる。
次に、本発明の一態様に係る電子デバイスの一例である発光素子の構成要素の詳細について、以下説明を行う。
発光層130は少なくとも、ホスト材料131を有し、さらにゲスト材料132を有すると好ましい。また、後述するように、ホスト材料131は有機化合物131_1及び有機化合物131_2を有していても良い。発光層130中では、ホスト材料131が重量比で最も多く存在し、ゲスト材料132は、ホスト材料131中に分散される。ゲスト材料132が蛍光性化合物の場合、発光層130のホスト材料131(有機化合物131_1及び有機化合物131_2)のS1準位は、発光層130のゲスト材料(ゲスト材料132)のS1準位よりも高いことが好ましい。また、ゲスト材料132が燐光性化合物の場合、発光層130のホスト材料131(有機化合物131_1及び有機化合物131_2)のT1準位は、発光層130のゲスト材料(ゲスト材料132)のT1準位よりも高いことが好ましい。
正孔注入層111は、一対の電極の一方(電極101または電極102)からのホール注入障壁を低減することでホール注入を促進する機能を有し、例えば電子受容性を有する遷移金属酸化物、フタロシアニン誘導体、芳香族アミン、ヘテロポリ酸などによって形成される。遷移金属酸化物としては、チタン酸化物、バナジウム酸化物、タンタル酸化物、モリブデン酸化物、タングステン酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、銀酸化物などが挙げられ、該遷移金属酸化物は電子受容性に優れ、真空蒸着法や湿式法によって簡便に成膜を行うことができるため好ましい。また、フタロシアニン誘導体としては、フタロシアニンや金属フタロシアニンなどが挙げられる。芳香族アミンとしてはベンジジン誘導体やフェニレンジアミン誘導体などが挙げられる。ポリチオフェンやポリアニリンなどの高分子化合物を用いることもでき、例えば自己ドープされたポリチオフェンであるポリ(エチレンジオキシチオフェン)/ポリ(スチレンスルホン酸)などがその代表例である。また、ヘテロポリ酸としては、リンモリブデン酸、リンタングステン酸、ケイモリブデン酸、ケイタングステン酸などが挙げられる。ヘテロポリ酸や高分子化合物は湿式法により簡便に成膜を行うことができるため好ましい。
正孔輸送層112は正孔輸送性材料を含む層であり、正孔注入層111の材料として例示した正孔輸送性材料を使用することができる。正孔輸送層112は正孔注入層111に注入された正孔を発光層130へ輸送する機能を有するため、正孔注入層111のHOMO(Highest Occupied Molecular Orbital、最高被占軌道ともいう)準位と同じ、あるいは近いHOMO準位を有することが好ましい。
電子輸送層118は、電子注入層119を経て一対の電極の他方(電極101または電極102)から注入された電子を発光層130へ輸送する機能を有する。電子輸送性材料としては、正孔よりも電子の輸送性の高い材料を用いることができ、1×10−6cm2/Vs以上の電子移動度を有する材料であることが好ましい。電子を受け取りやすい化合物(電子輸送性を有する材料)としては、含窒素複素芳香族化合物のようなπ電子不足型複素芳香族や金属錯体などを用いることができる。具体的には、発光層130に用いることができる電子輸送性材料として挙げたピリジン誘導体、ビピリジン誘導体、ピリミジン誘導体、トリアジン誘導体、キノキサリン誘導体、ジベンゾキノキサリン誘導体、フェナントロリン誘導体、トリアゾール誘導体、ベンゾイミダゾール誘導体、オキサジアゾール誘導体などが挙げられるが、窒素を二つ以上含む炭素数1乃至20の複素芳香族骨格を有すると好ましい。特に、ピリミジン骨格、及びトリアジン骨格を有する化合物であると好ましい。また、1×10−6cm2/Vs以上の電子移動度を有する物質であることが好ましい。なお、正孔よりも電子の輸送性の高い物質であれば、上記以外の物質を電子輸送層118として用いても構わない。また、電子輸送層118は、単層だけでなく、上記物質からなる層が二層以上積層してもよい。
電子注入層119は電極102からの電子注入障壁を低減することで電子注入を促進する機能を有し、例えば第1族金属、第2族金属、あるいはこれらの酸化物、ハロゲン化物、炭酸塩などを用いることができる。また、先に示す電子輸送性材料と、これに対して電子供与性を示す材料の複合材料を用いることもできる。電子供与性を示す材料としては、第1族金属、第2族金属、あるいはこれらの酸化物などを挙げることができる。具体的には、フッ化リチウム(LiF)、フッ化ナトリウム(NaF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。また、フッ化エルビウム(ErF3)のような希土類金属化合物を用いることができる。また、電子注入層119にエレクトライドを用いてもよい。該エレクトライドとしては、例えば、カルシウムとアルミニウムの混合酸化物に電子を高濃度添加した物質等が挙げられる。また、電子注入層119に、電子輸送層118で用いることが出来る物質を用いても良い。
量子ドットは、数nm乃至数十nmサイズの半導体ナノ結晶であり、1×103個乃至1×106個程度の原子から構成されている。量子ドットはサイズに依存してエネルギーシフトするため、同じ物質から構成される量子ドットであっても、サイズによって発光波長が異なる。そのため、用いる量子ドットのサイズを変更することによって、容易に発光波長を変更することができる。
電極101及び電極102は、発光素子の陽極または陰極としての機能を有する。電極101及び電極102は、金属、合金、導電性化合物、およびこれらの混合物や積層体などを用いて形成することができる。
また、本発明の一態様に係る発光素子は、ガラス、プラスチックなどからなる基板上に作製すればよい。基板上に作製する順番としては、電極101側から順に積層しても、電極102側から順に積層しても良い。
本実施の形態においては、実施の形態1に示す発光素子の構成と異なる構成の発光素子、及び当該発光素子の発光機構について、図3及び図4を用いて、以下説明を行う。なお、図3及び図4において、図2(A)に示す符号と同様の機能を有する箇所には、同様のハッチパターンとし、符号を省略する場合がある。また、同様の機能を有する箇所には、同様の符号を付し、その詳細な説明は省略する場合がある。
図3(A)は、発光素子250の断面模式図である。
発光層120の発光機構について、以下説明を行う。
・Host(122):ホスト材料122
・SFG:ゲスト材料121(蛍光材料)のS1準位
・TFG:ゲスト材料121(蛍光材料)のT1準位
・SFH:ホスト材料122のS1準位
・TFH:ホスト材料122のT1準位
図4(A)は、発光素子252の断面模式図である。
次に、発光層140の発光機構について、以下説明を行う。
・Host(142_1):有機化合物142_1(ホスト材料)
・Host(142_2):有機化合物142_2(ホスト材料)
・TPG:ゲスト材料141(燐光材料)のT1準位
・SPH1:有機化合物142_1(ホスト材料)のS1準位
・TPH1:有機化合物142_1(ホスト材料)のT1準位
・SPH2:有機化合物142_2(ホスト材料)のS1準位
・TPH2:有機化合物142_2(ホスト材料)のT1準位
・SPE:励起錯体のS1準位
・TPE:励起錯体のT1準位
次に、発光層120、発光層140、及び発光層170に用いることのできる材料について、以下説明する。
発光層120中では、ホスト材料122が重量比で最も多く存在し、ゲスト材料121(蛍光材料)は、ホスト材料122中に分散される。ホスト材料122のS1準位は、ゲスト材料121(蛍光材料)のS1準位よりも高く、ホスト材料122のT1準位は、ゲスト材料121(蛍光材料)のT1準位よりも低いことが好ましい。
発光層140中では、ホスト材料142が重量比で最も多く存在し、ゲスト材料141(燐光材料)は、ホスト材料142中に分散される。発光層140のホスト材料142(有機化合物142_1及び有機化合物142_2)のT1準位は、ゲスト材料141のT1準位よりも高いことが好ましい。
発光層170に用いることのできる材料としては、実施の形態1に示す発光層に用いることのできる材料を援用すればよく、そうすることで、発光効率の高い発光素子を作製することができる。
図5(A)は、発光装置を示す上面図、図5(B)は図5(A)をA−BおよびC−Dで切断した断面図である。この発光装置は、発光素子の発光を制御するものとして、点線で示された駆動回路部(ソース側駆動回路)601、画素部602、駆動回路部(ゲート側駆動回路)603を含んでいる。また、604は封止基板、625は乾燥材、605はシール材であり、シール材605で囲まれた内側は、空間607になっている。
図6には発光装置の一例として、白色発光を呈する発光素子を形成し、着色層(カラーフィルタ)を形成した発光装置の例を示す。
トップエミッション型の発光装置の断面図を図7に示す。この場合、基板1001は光を通さない基板を用いることができる。TFTと発光素子の陽極とを接続する接続電極を作製するまでは、ボトムエミッション型の発光装置と同様に形成する。その後、第3の層間絶縁膜1037を電極1022を覆って形成する。この絶縁膜は平坦化の役割を担っていても良い。第3の層間絶縁膜1037は第2の層間絶縁膜1021と同様の材料の他、他の様々な材料を用いて形成することができる。
本実施の形態では、本発明の一態様の電子機器について説明する。
本実施の形態では、本発明の一態様の発光素子を様々な照明装置に適用する一例について、図10及び図11を用いて説明する。本発明の一態様である発光素子を用いることで、発光効率が良好な、信頼性の高い照明装置を作製できる。
比較発光素子1乃至比較発光素子4、発光素子5乃至発光素子8及び発光素子9乃至発光素子12の正孔注入層111に用いた有機化合物と正孔注入層111の屈折率を測定した。屈折率はJ.A.Woolam社製回転補償子型多入射角高速分光エリプソメーター(M−2000U)を用いて室温で測定した。測定サンプルは石英基板上に真空蒸着法にて作製した。n Ordinary及びn Extraordinaryを測定し、n averageを算出した。
≪比較発光素子1乃至比較発光素子4の作製≫
ガラス基板上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。なお、ITSO膜の波長が532nmの光における屈折率(n Ordinary)は2.07である。
発光素子5乃至発光素子8の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
発光素子9乃至発光素子12の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
次に、上記作製した比較発光素子1乃至比較発光素子4及び発光素子5乃至発光素子12の特性を測定した。輝度およびCIE色度の測定には色彩輝度計(トプコン社製、BM−5A)を用い、電界発光スペクトルの測定にはマルチチャンネル分光器(浜松ホトニクス社製、PMA−11)を用いた。なお、各発光素子の測定は室温(23℃に保たれた雰囲気)で行った。
図17に表4に示した各素子の値を用いて、各正孔注入層111に用いた有機材料による、色度xと外部量子効率の関係を示す。図17中、「DBT3P−II」の曲線のデータには比較発光素子1乃至比較発光素子4の値を、「dmCBP」の曲線のデータには発光素子5乃至発光素子8の値を、「TAPC」の曲線のデータには発光素子9乃至発光素子12の値を、それぞれ用いた。ここで、比較発光素子1乃至比較発光素子4及び発光素子5乃至発光素子12において、正孔注入層111の膜厚が同一の場合でも、用いている有機化合物によって、屈折率が異なるため、各発光素子の発光領域から基板までの光路長が変化する。光路長が変化すると、外部量子効率も変化するため、正孔注入層111の屈折率と外部量子効率の関係を評価するとき、各発光素子で光路長を調整する必要があるが、発光素子作製によるEL層膜厚の微調整は困難である。
ここで、正孔注入層111における電子供与性物質に対する電子受容性物質(MoO3)の体積比率(以下、MoO3の体積比率と示す)と外部量子効率の関係を調査した。また、素子構造の詳細を表5に示す。また、使用した化合物の構造と略称を以下に示す。なお、他の有機化合物については上述の化合物を参照すればよい。
発光素子13乃至発光素子18の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111と発光層130の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
次に、上記作製した発光素子13乃至発光素子18の輝度−外部量子効率特性を測定した。測定は上述の方法で行った。
比較発光素子19乃至比較発光素子22、発光素子23乃至発光素子26及び発光素子27乃至発光素子30の正孔注入層111に用いた有機化合物の屈折率を測定した。屈折率の測定は実施例1と同様に行った。
≪比較発光素子19乃至比較発光素子22の作製≫
比較発光素子19乃至比較発光素子22の作製工程は上記比較発光素子1乃至比較発光素子4の作製工程と正孔注入層111と発光層130の作製工程のみ異なり、他の工程は比較発光素子1乃至比較発光素子4と同様に行った。
発光素子23乃至発光素子26の作製工程は上記比較発光素子19乃至比較発光素子22の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子19乃至比較発光素子22と同様に行った。
発光素子27乃至発光素子30の作製工程は上記比較発光素子19乃至比較発光素子22の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子19乃至比較発光素子22と同様に行った。
次に、上記作製した比較発光素子19乃至比較発光素子22及び発光素子23乃至発光素子30の特性を測定した。測定は実施例1と同様に行った。
比較発光素子31乃至比較発光素子34、発光素子35乃至発光素子38、発光素子39乃至発光素子42、発光素子43乃至発光素子46、比較発光素子47乃至比較発光素子50の正孔注入層111に用いた有機化合物及び比較発光素子31乃至比較発光素子34、発光素子35乃至発光素子38、発光素子39乃至発光素子42、発光素子43乃至発光素子46及び比較発光素子47乃至比較発光素子50に用いた正孔注入層111の屈折率を測定した。屈折率の測定は実施例1に記載の方法と同様に行った。
≪比較発光素子31乃至比較発光素子34の作製≫
ガラス基板上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。
発光素子35乃至発光素子46及び比較発光素子47乃至比較発光素子50の作製工程は上記比較発光素子31乃至比較発光素子34の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子31乃至比較発光素子34と同様に行った。素子構造の詳細は表11乃至表14に示す通りであるため、作製方法の詳細は省略する。
次に、上記作製した比較発光素子31乃至比較発光素子34、発光素子35乃至発光素子46及び比較発光素子47乃至比較発光素子50の特性を測定した。測定は実施例1と同様に行った。
次に、比較発光素子31、発光素子35、発光素子39、発光素子43及び比較発光素子47の2mAにおける定電流駆動試験を行った。その結果を図30に示す。図30から、比較発光素子31、発光素子35、発光素子39、発光素子43の信頼性は、比較発光素子47と比較し信頼性が良好であることが分かった。特に発光素子43の信頼性は良好であることが分かった。上述の通り、比較発光素子31、発光素子35、発光素子39、発光素子43の正孔注入層111に用いた有機化合物は分子内に電子供与性基を有しているため、比較発光素子47に用いたUGH−2と比較し、正孔注入性が良好であるためであると考えられる。よって、正孔注入層111の正孔注入性が良好な方が発光素子の信頼性が良好であることが分かった。なお、図30において、比較発光素子31、発光素子35及び発光素子39の信頼性試験結果は重なっている。
比較発光素子51乃至比較発光素子54、比較発光素子55乃至比較発光素子58、発光素子59乃至発光素子62、発光素子63乃至発光素子66の正孔注入層111の屈折率を測定した。屈折率の測定は実施例1に記載の方法と同様に行った。波長が633nmの光における各膜の屈折率(n Ordinary)の値を表18に示す。
≪比較発光素子51乃至比較発光素子54の作製≫
ガラス基板上に電極101として、ITSO膜を厚さが70nmになるように形成した。なお、電極101の電極面積は、4mm2(2mm×2mm)とした。
比較発光素子55乃至比較発光素子58及び発光素子59乃至発光素子66の作製工程は上記比較発光素子51乃至比較発光素子54の作製工程と正孔注入層111の作製工程のみ異なり、他の工程は比較発光素子51乃至比較発光素子54と同様に行った。素子構造の詳細は表16及び表17に示す通りであるため、作製方法の詳細は省略する。
次に、上記作製した比較発光素子51乃至比較発光素子58及び発光素子59乃至発光素子66の特性を測定した。測定は実施例1と同様に行った。1000cd/m2付近における各素子の特性を表19に示す。表19に示す外部量子効率は視野角補正を行う前の外部量子効率を示す。
図32に表19に示した各素子の値を用いて、各正孔注入層111に用いた有機材料による、色度yと外部量子効率の関係を示す。図32中、「β−TNB」の曲線のデータには比較発光素子51乃至比較発光素子54の値を、「NPB」の曲線のデータには比較発光素子55乃至比較発光素子58の値を、「BPAFLP」の曲線のデータには発光素子59乃至発光素子62の値を、「TAPC」の曲線のデータには発光素子63乃至発光素子66の値をそれぞれ用いた。
本参考例では、実施例1で用いた、Ir(pbi−diBuCNp)3の合成方法について説明する。
4−アミノ−3,5−ジクロロベンゾニトリル52g(280mmol)、イソブチルボロン酸125g(1226mmol)、リン酸三カリウム260g(1226mmol)、2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシビフェニル(S−phos)5.4g(13.1mmol)、トルエン1500mLを3000mL三口フラスコに入れ、フラスコ内を窒素置換し、フラスコ内を減圧しながら攪拌し、この混合物を脱気した。脱気後、トリス(ジベンジリデンアセトン)ジパラジウム(0)4.8g(5.2mmol)を加え、窒素気流下、130℃で12時間攪拌した。得られた反応溶液にトルエンを加えて、セライト(和光純薬工業株式会社、カタログ番号:531−16855)/フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)/酸化アルミニウムの順に積層したろ過補助剤を通して吸引ろ過した。得られたろ液を濃縮し、油状物を得た。得られた油状物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、トルエンを用いた。得られたフラクションを濃縮して、黄色油状物を61g、収率95%で得た。核磁気共鳴法(NMR)により得られた黄色油状物が4−アミノ−3,5−ジイソブチルベンゾニトリルであることを確認した。ステップ1の合成スキームを下記式(a−1)に示す。
ステップ1で合成した4−アミノ−3,5−ジイソブチルベンゾニトリル30g(131mmol)、炭酸セシウム86g(263mmol)、ジメチルスルホキシド(DMSO)380mL、2−フルオロニトロベンゼン19g(131mmol)を1000mL三口フラスコに入れ、窒素気流下、120℃で20時間攪拌した。所定時間経過後の反応溶液を、クロロホルムによる抽出を行い粗生成物を得た。得られた粗生成物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、ヘキサン:酢酸エチル=7:1を用いた。得られたフラクションを濃縮して、橙色固体を得た。得られた固体にヘキサンを加えて吸引ろ過し、黄色固体を16g、収率35%で得た。核磁気共鳴法(NMR)により得られた黄色固体が4−[N−(2−ニトロフェニル)アミノ]−3,5−ジイソブチルベンゾニトリルであることを確認した。ステップ2の合成スキームを下記式(a−2)に示す。
ステップ2で合成した4−[N−(2−ニトロフェニル)アミノ]−3,5−ジイソブチルベンゾニトリル21g(60.0mmol)、水11mL(0.6mol)、エタノール780mLを2000mL三口フラスコに入れ、撹拌した。この混合物に塩化スズ(II)57g(0.3mol)を加え、窒素気流下、80℃で7.5時間撹拌した。所定時間経過後、この混合物を2M水酸化ナトリウム水溶液400mLに注ぎ、16時間室温で撹拌した。析出した沈殿物を吸引ろ過することで除去し、さらにクロロホルムで洗浄し、ろ液を得た。得られたろ液をクロロホルムによる抽出を行った。その後、抽出した溶液を濃縮して白色固体を20g、収率100%で得た。核磁気共鳴法(NMR)により得られた白色固体が4−[N−(2−アミノフェニル)アミノ]−3,5−ジイソブチルベンゾニトリルであることを確認した。ステップ3の合成スキームを下記式(a−3)に示す。
ステップ3で合成した4−[N−(2−アミノフェニル)アミノ]−3,5−ジイソブチルベンゾニトリル20g(60.0mmol)、アセトニトリル200mL、ベンズアルデヒド6.4g(60.0mmol)を1000mLナスフラスコに入れ、100℃で1時間攪拌した。この混合物に塩化鉄(III)100mg(0.60mmol)を加え、100℃で24時間攪拌した。所定時間経過後の反応溶液を、クロロホルムによる抽出を行い、油状物を得た。得られた油状物にトルエンを加えて、セライト/フロリジール/酸化アルミニウムの順に積層したろ過補助剤を通して吸引ろ過した。得られたろ液を濃縮し、油状物を得た。得られた油状物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、トルエンを用いた。得られたフラクションを濃縮して、固体を得た。この固体を酢酸エチル/ヘキサンで再結晶したところ、目的物である白色固体を4.3g、収率18%で得た。核磁気共鳴法(NMR)により得られた白色固体が1−(4−シアノ−2,6−ジイソブチルフェニル)−2−フェニル−1H−ベンゾイミダゾール(略称:Hpbi−diBuCNp)であることを確認した。ステップ4の合成スキームを下記式(a−4)に示す。
ステップ4で合成した1−(4−シアノ−2,6−ジイソブチルフェニル)−2−フェニル−1H−ベンゾイミダゾール(略称:Hpbi−diBuCNp)1.8g(4.4mmol)、トリス(アセチルアセトナト)イリジウム(III)0.43g(0.88mmol)を、三方コックを付けた反応容器に入れ、250℃にて39時間加熱した。得られた反応混合物にトルエンを加え、不溶物を取り除いた。得られたろ液を濃縮し、固体を得た。得られた固体をシリカカラムクロマトグラフィー(中性シリカ)により精製した。展開溶媒には、トルエンを用いた。得られたフラクションを濃縮して、固体を得た。得られた固体を酢酸エチル/ヘキサンで再結晶し、黄色固体を0.26g、収率21%で得た。合成スキームを下記式(a−5)に示す。
Claims (22)
- 第1の電極と、第2の電極と、第1の層と、第2の層と、を有し、
前記第1の層は、前記第1の電極と、前記第2の層と、の間に設けられ、
前記第2の層は、前記第1の層と、前記第2の電極と、の間に設けられ、
前記第1の層は、第1の物質と、第1の有機化合物と、を有し、
前記第1の物質は、電子受容性を有し、
前記第1の有機化合物を薄膜とした際の屈折率は、1以上1.75以下である、
電子デバイス。 - 第1の電極と第2の電極の間に、第1の層を有し、
前記第1の層は第1の有機化合物及び第1の物質を有し、
前記第1の有機化合物は第1の骨格と電子供与性骨格とを有し、
前記第1の骨格はテトラアリールメタン骨格またはテトラアリールシラン骨格である、電子デバイス。 - 第1の電極と、第2の電極との間に、第1の層と、第2の層と、第3の層と、を有し、
前記第1の層は、前記第1の電極と、前記第2の層と、の間に設けられ
前記第2の層は、前記第1の層と、前記第3の層と、の間に設けられ、
前記第1の層は、第1の物質と、第1の有機化合物と、を有し、
前記第1の物質は、電子受容性を有し、
前記第3の層は光を発するまたは吸収する機能を有し、
前記第1の層の屈折率は、前記第2の層の屈折率及び前記第3の屈折率の双方よりも低く、
前記第1の有機化合物を薄膜とした際の屈折率は、1以上1.75以下である、電子デバイス。 - 請求項2において、
前記第1の層の屈折率は1以上1.75以下である、電子デバイス。 - 請求項2において、
前記テトラアリールメタン骨格及び前記テトラアリールシラン骨格におけるアリール基はそれぞれ独立に、置換又は無置換の炭素数6乃至13のアリール基である、電子デバイス。
なお、前記アリール基どうしは互いに結合し、環を形成してもよい。 - 請求項5において、
前記アリール基はそれぞれ独立に、置換又は無置換のフェニル基である、電子デバイス。
なお、前記フェニル基どうしは互いに結合し、環を形成してもよい。 - 請求項2において、
前記電子供与性骨格は少なくとも、ピロール骨格、芳香族アミン骨格、アクリジン骨格、アゼピン骨格のうち、いずれか一を含む、電子デバイス。 - 請求項2において、
前記第1の有機化合物のガラス転移点(Tg)が100℃以上である、電子デバイス。 - 請求項1または請求項2において、
前記第1の層の屈折率は前記第2の層の屈折率よりも低い、電子デバイス。 - 請求項1または請求項3において、
前記第1の有機化合物は電子供与性を有する、電子デバイス。 - 請求項3において、
前記第3の層は、前記第2の層と接する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の層は、前記第2の層と接する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の層の屈折率は、前記第1の電極の屈折率よりも低い、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の有機化合物に対して、前記第1の物質の体積比率は、0.01以上0.3以下である、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の物質は、チタン酸化物、バナジウム酸化物、タンタル酸化物、モリブデン酸化物、タングステン酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、及び銀酸化物のいずれか一を含む、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の物質は、TCNQ、F4TCNQ、及びF6TCNNQのいずれか一である、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第1の電極は陽極であり、前記第2の電極が陰極である、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第2の層は、発光機能を有する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項において、
前記第2の層は、光電変換機能を有する、電子デバイス。 - 請求項1乃至請求項3のいずれか一項に記載の電子デバイスと、
カラーフィルタまたはトランジスタの少なくとも一方と、
を有する表示装置。 - 請求項20に記載の表示装置と、
筐体またはタッチセンサの少なくとも一方と、
を有する電子機器。 - 請求項1乃至請求項3のいずれか一項に記載の電子デバイスと、
筐体またはタッチセンサの少なくとも一方と、
を有する照明装置。
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JP2023082169A (ja) | 2023-06-13 |
JP2023082168A (ja) | 2023-06-13 |
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US10950805B2 (en) | 2021-03-16 |
JP7257952B2 (ja) | 2023-04-14 |
JPWO2018211377A1 (ja) | 2020-05-14 |
DE112018008264B4 (de) | 2023-11-30 |
DE112018002586T5 (de) | 2020-03-05 |
US20200176692A1 (en) | 2020-06-04 |
DE112018002586B4 (de) | 2023-03-09 |
KR20220003140A (ko) | 2022-01-07 |
US20210257562A1 (en) | 2021-08-19 |
CN110603658A (zh) | 2019-12-20 |
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