Light-emitting element, light-emitting device, electronic device, and lighting device

Abstract

To provide a novel organic compound having high hole-transport property, and to provide a long-lifetime light-emitting element.SOLUTION: An organic compound represented by General Formula (G0) is provided. In the General Formula (G0), Ar1 represents a substituted or unsubstituted naphthyl group, Ar2 represents a substituted or unsubstituted carbazolyl group, Ar3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirofluorenyl group, and α1 and α2 each independently represent a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. [Background technology]

[0002] In recent years, electroluminescence (EL) Research and development of light-emitting devices that use EL elements (also called EL elements) is currently being actively carried out. The basic structure of the device is a layer containing a light-emitting material sandwiched between a pair of electrodes. By applying a voltage, it is possible to obtain light emission from the light-emitting substance.

[0003] Since EL elements are self-emitting, they have higher pixel visibility than LCDs and no backlighting. It has the advantage of being suitable as a flat panel display element because it does not require a light source. Another major advantage of EL elements is that they can be made thin and lightweight. Another feature is its extremely fast response speed.

[0004] Since the EL element can be formed in a film shape, it is possible to obtain planar light emission. This makes it easy to form large-area elements. This is a feature that is difficult to obtain with point light sources such as fluorescent lamps, or linear light sources such as fluorescent lamps, and is therefore suitable for lighting, etc. It is also highly useful as a surface light source.

[0005] EL elements can be broadly classified according to whether the luminescent material is an organic compound or an inorganic compound. An organic electroluminescence device in which an organic compound is used as a light-emitting material and a layer containing the organic compound is provided between a pair of electrodes. In the case of a semiconductor, when a voltage is applied to the light-emitting element, electrons are emitted from the cathode and holes are emitted from the anode. Electrons are injected into the layer containing the organic compound, and current flows. Then, the injected electrons and holes excite the organic compound to an excited state, and light emission is obtained from the excited organic compound is obtained.

[0006] As types of excited states formed by organic compounds, singlet excited states and triplet excited states are possible and light emission from the singlet excited state (S * ) is fluorescence, and light emission from the triplet excited state (T * ) is called phosphorescence.

[0007] Regarding such a light-emitting device, there are many problems depending on the material in improving its device characteristics, and in order to overcome these, improvements in device structure, material development, etc. have been carried out. For example, in Patent Document 1, a carbazole derivative with high hole-transporting properties is disclosed as a material that can be used to form a light-emitting device with high luminous efficiency.

Prior Art Documents

Patent Documents

[0008]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0009] The development of organic EL devices still has room for improvement in terms of luminous efficiency, reliability, cost, etc., and the development of more excellent materials is desired. Therefore, an aspect of the present invention aims to provide a novel organic compound with high hole-transporting properties.

[0010]

[0011] ​​​​Another aspect of the present invention aims to provide a light-emitting element with a long lifespan.

[0012] Another aspect of the present invention aims to provide a highly reliable light-emitting device, electronic device, and lighting device using the light-emitting element.

Means for Solving the Problems

[0013] The organic compound of one aspect of the present invention has a substituent containing a fluorene skeleton or a spirofluorene skeleton, a substituent containing a naphthalene skeleton, and a substituent containing a carbazole skeleton, each of which is a tertiary amine directly bonded to a nitrogen atom. The organic compound of one aspect of the present invention exhibits high hole transportability. Specifically, one aspect of the present invention is an organic compound represented by general formula (G0).

[0014]

[0015]

Chemical Formula

[0016] In general formula (G0), Ar 1 represents a naphthyl group, Ar 2 represents a carbazolyl group, A r 3 represents a fluorenyl group or a spirofluorenyl group, α 1 and α 2 each independently represent a phenylene group or a biphenyldiyl group, and the naphthyl group, the carbazolyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyldiyl group are each independently unsubstituted or have as a substituent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms.

[0017] ​​In addition, one aspect of the present invention is an organic compound represented by the general formula (G1).

[0018]

Chemical formula

[0019] In the general formula (G1), Ar 1 represents a naphthyl group, Ar 3 represents a fluorenyl group or a spiro fluorenyl group, Ar 4 represents an aryl group having 6 to 25 carbon atoms, and α 1 represents a phenylene group or a biphenyldiyl group, and R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R 11 ~R 17 and R 21 ~R 24 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and the naphthyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the bi phenyldiyl group are each independently unsubstituted or have an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

[0020] In addition, one aspect of the present invention is an organic compound represented by the general formula (G2).

[0021]

Chemical formula

[0022] In the general formula (G2), Ar 1 represents a naphthyl group, Ar 3 represents a fluorenyl group or a spiro fluorenyl group, and α 1 represents a phenylene group or a biphenyldiyl group, and R 11 ~ R 17 and R 21 ~R24 each independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R 31 ~R 35 each independently represents hydrogen or represents an alkyl group having 1 to 10 carbon atoms. The naphthyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyldiyl group each independently have no substituent or have an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

[0023] Also, one aspect of the present invention is an organic compound represented by the general formula (G3).

[0024]

Chemical formula

[0025] In the general formula (G3), Ar 3 represents a fluorenyl group or a spirofluorenyl group, and R 11 ~R 17 , R 21 ~R 24 , R 41 ~R 47 , and R 51 ~R 54 each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R 31 ~ R 35 each independently represent hydrogen or an alkyl group having 1 to 10 carbon atoms. The fluorenyl group or the spirofluorenyl group has no substituent or has an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

[0026] Also, one aspect of the present invention is a light-emitting device including the above organic compound between a pair of electrodes.

[0027] One aspect of the present invention is a light-emitting element having a light-emitting layer between a pair of electrodes, the light-emitting layer including the above-described organic compound and a light-emitting substance. Further, the light-emitting element according to one aspect of the present invention has a light-emitting layer between a pair of electrodes and includes a first organic compound, a second organic compound, and a light-emitting substance. The first organic compound is the above-described organic compound, and the second organic compound is an organic compound having electron-transporting properties. In particular, it is preferable that the first organic compound and the second organic compound form a combination that forms an exciplex because the luminous efficiency of the light-emitting element can be increased.

[0028] Further, one aspect of the present invention is a light-emitting element having a light-emitting layer containing a light-emitting substance between a pair of electrodes and a hole-transporting layer in contact with the light-emitting layer, the hole-transporting layer including the above-described organic compound.

[0029] Further, one aspect of the present invention is a light-emitting element having a light-emitting layer between a pair of electrodes and a hole-transporting layer in contact with the light-emitting layer. The light-emitting layer contains a light-emitting substance and the above-described organic compound, and the hole-transporting layer contains the organic compound according to one aspect of the present invention.

[0030] Further, one aspect of the present invention is a light-emitting device including the above-described light-emitting element in a light-emitting unit. Further, one aspect of the present invention is an electronic device including the light-emitting device in a display unit. Further, one aspect of the present invention is a lighting device including the light-emitting device in a light-emitting unit.

[0031] The light-emitting element using the organic compound according to one aspect of the present invention has a long lifespan, and thus a highly reliable light-emitting device can be realized. Similarly, by applying one aspect of the present invention, a highly reliable electronic device and a lighting device can be realized.

[0032] In this specification, the term "light-emitting device" includes an image display device using a light-emitting element. In addition, the light emitting element is connected to a connector, such as anisotropic conductive film or TCP (Tape Cable). A module with a printed wiring board (Package A) attached, and a TCP Module with wiring board or COG (Chip On Glass) type for light emitting element According to the formula, all modules on which ICs (integrated circuits) are directly mounted are also included in the light-emitting device. Furthermore, it also includes light-emitting devices used in lighting fixtures and the like. Effect of the Invention

[0033] The organic compound of one embodiment of the present invention described above exhibits high hole-transport properties. By using an organic compound, a light-emitting element having a long life can be realized. According to one embodiment, a highly reliable light-emitting device, electronic device, and lighting device can be provided. [Brief description of the drawings]

[0034]

Figure 1

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Figure 17

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Figure 22

Figure 23

Embodiments for Carrying Out the Invention

[0035] The embodiments will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it is easily understood by those skilled in the art that the form and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not construed as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are commonly used for the same parts or parts having the same function among different drawings, and the repeated description thereof will be omitted. without departing from the spirit and scope of the present invention. Therefore, the present invention is not construed as being limited to the description of the embodiments shown below. In the configuration of the invention described below, the same reference numerals are commonly used for the same parts or parts having the same function among different drawings, and the repeated description thereof will be omitted. In the configuration of the invention described below, the same reference numerals are commonly used for the same parts or parts having the same function among different drawings, and the repeated description thereof will be omitted. The repeated description thereof will be omitted.

[0036] (Embodiment 1) In this embodiment, an organic compound according to one aspect of the present invention will be described.

[0037] One aspect of the present invention is a tertiary amine in which a substituent containing a fluorene skeleton or a spirofluorene skeleton, a substituent containing a naphthalene skeleton, and a substituent containing a carbazole skeleton are directly bonded to a nitrogen atom. The organic compound according to one aspect of the present invention exhibits high hole transportability. By using the organic compound, a light-emitting element with a long lifespan can be realized. Specifically, one aspect of the present invention is an organic compound represented by the general formula (G0). The organic compound according to one aspect of the present invention exhibits high hole transportability. By using the organic compound, a light-emitting element with a long lifespan can be realized. By using the organic compound, a light-emitting element with a long lifespan can be realized.

[0038] Specifically, one aspect of the present invention is an organic compound represented by the general formula (G0).

[0039] [Chemical formula]

[0040] In the general formula (G0), Ar 1 represents a naphthyl group, Ar 2 represents a carbazolyl group, A r 3 represents a fluorenyl group or a spirofluorenyl group, and α 1 and α 2 each independently represents a phenylene group or a biphenyldiyl group. The naphthyl group, the carbazolyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyldiyl group are each independently unsubstituted or have as a substituent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms.

[0041] Ar shown in the general formula (G0) 2 Specific structures of include, for example, the substituents shown in Structural Formulas (1-1) to Structural

[0042]

Chemical formula

[0043]

Chemical formula

[0044] Moreover, one aspect of the present invention is an organic compound represented by the general formula (G1). The organic compound represented by the general formula (G1) has a wide range of choices in the synthesis method, and is preferable because high purity and low cost of the material can be achieved easily.

[0045]

Chemical formula

[0046] In the general formula (G1), Ar 1 represents a naphthyl group, Ar 3 represents a fluorenyl group or a spiro fluorenyl group, Ar 4 represents an aryl group having 6 to 25 carbon atoms, α 1 represents a phenylene group or a biphenyldiyl group, and R ~R 11 ~R 17 and R 21 ~R24 each represents independently, hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, the naphthyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, or the bi phenyl diyl group is each independently unsubstituted or has an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

[0047] Further, in the general formula (G1), when Ar 4 is a phenyl group, compared with the case where Ar 4 is an alkyl group, the thermal properties of the organic compound are improved, so that a light-emitting device with a long lifespan can be fabricated, which is preferable. Therefore, one aspect of the present invention is an organic compound represented by the general formula (G2).

[0048]

Chemical formula

[0049] In the general formula (G2), Ar 1 represents a naphthyl group, Ar 3 represents a fluorenyl group or a spiro fluorenyl group, α 1 represents a phenylene group or a biphenyl diyl group, and R 11 ~ R 17 and R 21 ~R 24 each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R 31 ~R 35 each independently represent hydrogen or an alkyl group having 1 to 10 carbon atoms, and the naphthyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyl diyl group are each independently unsubstituted ​​having as a substituent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 25 carbon atoms, or the like and having

[0050] Ar represented by general formulas (G0) to (G2) 1 Specific structures of, for example, the substituents represented by structural formulas (2 -1) to (2-3) may be mentioned.

[0051]

Chemical formula

[0052] α represented by general formulas (G0) to (G2) 1 , and α represented by general formula (G0) 2 Specific structures of include, for example, the substituents represented by structural formulas (3-1) to (3-12).

[0053]

Chemical formula

[0054] Moreover, one aspect of the present invention is an organic compound represented by general formula (G3). General formula (G3) The organic compound is preferable because the synthesis cost can be reduced.

[0055]

Chemical formula

[0056] In general formula (G3), Ar 3 represents a fluorenyl group or a spirofluorenyl group, and R 11 ~R 17 , R 21 ~R 24 , R 41 ~R 47 , and R 51 ~R 54 are each independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, R 31 ~ R 35 each independently represents hydrogen or an alkyl group having 1 to 10 carbon atoms, and the fluorenyl group or the spirofluorenyl group is unsubstituted or has an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

[0057] In each of the general formulas listed above, specific structures of Ar 3 include, for example, the substituents shown in Structural Formulas (4- 1) to (4-5).

[0058]

Chemical Formula

[0059] In each of the general formulas listed above, when the naphthyl group, carbazolyl group, fluorenyl group, spirofluorenyl group, phenylene group, or biphenyldiyl group has a substituent, examples of the substituent include an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 25 carbon atoms. Examples of these specific structures include the substituents shown in Structural Formulas (5-1) to (5-31). Also, examples of specific structures of R ~R 11 ~R 17 、R 21 ~R 24 、R 41 ~R 47 、and R 51 ~R 54 also include the substituents shown in Structural Formulas (5-1) to (5-31). Also, examples of specific structures of R ~R 31 ~R 35 include, for example, the substituents shown in Structural Formulas (5-1) to (5-8). ​​​​​

[0060]

Chem.

[0061] Specific examples of the organic compound represented by the general formula (G0) include the organic compounds represented by structural formula (100) to structural formula (1 57). However, the present invention is not limited thereto.

[0062]

Chem.

[0063]

Chem.

[0064]

Chem.

[0065]

Chem.

[0066]

Chem.

[0067]

Chem.

[0068]

Chem.

[0069]

Chem.

[0070]

Chem.

[0071]

Chem.

[0072]

Chem.

[0073] As a method for synthesizing the organic compound of one embodiment of the present invention, various reactions can be applied. For example, by performing Step 1 and Step 2 shown below, the organic compound of one embodiment of the present invention represented by the general formula (G0) can be synthesized. Note that the method for synthesizing the organic compound which is one embodiment of the present invention is not limited to the following synthesis method.

[0074] <Step 1> As shown in the synthesis scheme (A-1), a primary arylamine (a1) and an aryl halide (a2) are coupled using a metal catalyst in the presence of a base to obtain a secondary diarylamine (a3).

[0075]

Chem.

[0076] In the synthesis scheme (A-1), Ar 1 represents a naphthyl group, Ar 2 represents a carbazolyl group, α and α 1 and α 2 each independently represent a phenylene group or a biphenyldiyl group, and X 1 ​​​​​represents a halogen group or a trifluoromethanesulfonyl group, preferably a bromo group or an iodo group. Further, the naphthyl group, carbazolyl group, phenylene group, and biphenyldiyl group are each independently unsubstituted or have an alkyl group having 1 to 10 carbon atoms

[0077] [When performing the Buchwald-Hartwig reaction] In the synthesis scheme (A-1), examples of the palladium catalyst that can be used include bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, etc. Examples of the ligand of the palladium catalyst include tri(tert-butyl)phosphine, tris(n-hexyl)phosphine, tricyclohexylphosphine, etc. The catalysts and their ligands that can be used are not limited to these.

[0078] Examples of the base that can be used in the synthesis scheme (A-1) include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate. Examples of the solvent that can be used include toluene, xylene, benzene, tetrahydrofuran, etc. However, the bases and

[0079] [When performing the Ullmann reaction] In the synthesis scheme (A-1), R 101 and R 102 each independently represent a halogen or an acetyl group, etc. Examples of the halogen include chlorine, bromine, 101 and iodine. Further, copper(I) iodide in which R 102 is iodine, or copper(II) acetate in which R is preferred. The copper compounds used in the reaction are not limited to these. In addition to the copper compounds, copper can also be used. In the synthesis scheme (A-1), examples of the base that can be used include potassium carbonate and the like. The bases that can be used are not limited to these. In the synthesis scheme (A-1), examples of the solvent that can be used include 1,3-dimethyl -3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene and the like. The solvents that can be used are not limited to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU, xylene, or toluene having a high boiling point.

[0080] In the synthesis scheme (A-1), examples of the solvent that can be used include 1,3-dimethyl -3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU), toluene, xylene, benzene and the like. The solvents that can be used are not limited to these. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU, xylene, or toluene having a high boiling point. In the Ullmann reaction, since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU, xylene, or toluene having a high boiling point. Since the target product can be obtained in a shorter time and in a higher yield when the reaction temperature is 100 °C or higher, it is preferable to use DMPU, xylene, or toluene having a high boiling point. In addition, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use D MPU.

[0081] <Step 2> As shown in the synthesis scheme (A-2), by coupling a secondary diarylamine (a3) and an aryl halide (a4) in the presence of a base using a metal catalyst, an organic compound represented by the general formula (G0) can be obtained. In the synthesis scheme (A-2), Ar represents a naphthyl group, Ar

[0082] [Chemical formula]

[0083] In the synthesis scheme (A-2), Ar 1 represents a naphthyl group, Ar 2 represents a carbazolyl group, Ar 3 represents a fluorenyl group or a spirofluorenyl group, α 1 and α2 each independently represents a phenylene group or a biphenyldiyl group, and X 2 represents a halogen group or a trifluoromethanesulfonyl group, preferably represents a bromo group or an iodo group . Further, the naphthyl group, carbazolyl group, fluorenyl group, spirofluorenyl group, phen ylene group, and biphenyldiyl group are each independently unsubstituted or have an alkyl group having 1 to 1 0 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

[0084] [When performing the Buchwald-Hartwig reaction] In the synthesis scheme (A-2), when performing the Buchwald-Hartwig reaction, the palladium catalyst, the ligand of the palladium catalyst, the base, and the solvent that can be used include those similar to the synthesis scheme (A-1).

[0085] [When performing the Ullmann reaction] In the synthesis scheme (A-2), R 103 and R 104 each independently represents a halogen or an acetyl group or the like, and examples of the halogen include chlorine, bromine, and iodine. Further, copper(I) iodide in which R 103 is iodine, or copper(II) acetate in which R 104 is an acetyl group is preferred. The copper compound used in the reaction is not limited to these. Further, copper can be used in addition to the copper compound .

[0086] In the synthesis scheme (A-2), examples of the base and the solvent that can be used include those similar to the synthesis scheme (A-1).

[0087] ​In this manner, the organic compound of this embodiment can be synthesized.

[0088] The organic compound of this embodiment has a high hole transporting property, and therefore can be used as a material for a hole transporting layer of a light-emitting element. In addition, the light-emitting material of the light-emitting layer of the light-emitting element can be dispersed in the light-emitting layer. The light-emitting layer can be preferably used as a host material. and further comprising the organic compound of the present embodiment as an assist material. By using the organic compound of this embodiment mode, a light-emitting element with a long life can be realized. Furthermore, by using this light-emitting element, a highly reliable light-emitting device and an electronic device can be obtained. An instrument and a lighting device can be obtained.

[0089] This embodiment mode can be freely combined with other embodiment modes.

[0090] (Embodiment 2) In this embodiment, a light-emitting element of one embodiment of the present invention will be described with reference to FIG.

[0091] The light-emitting element exemplified in this embodiment has a pair of electrodes (a first electrode and a second electrode) and A layer containing a light-emitting organic compound (EL layer) is provided between the pair of electrodes. One of the electrodes functions as an anode and the other as a cathode.

[0092] Specific structural examples of the light-emitting element of one embodiment of the present invention will be described below.

[0093] The light-emitting element shown in FIG. 1A includes an EL layer 20 between a first electrode 201 and a second electrode 205. In this embodiment, the first electrode 201 functions as an anode, and the second electrode 20 5 functions as the cathode.

[0094] When a voltage higher than the threshold voltage of the light-emitting element is applied between the first electrode 201 and the second electrode 205, holes are injected into the EL layer 203 from the side of the first electrode 201, and electrons are injected from the side of the second electrode 205. The injected electrons and holes recombine in the EL layer 20 3, and the light-emitting substance contained in the EL layer 20

[0095] 3 emits light. The EL layer 203 has at least a light-emitting layer containing a light-emitting substance. As layers other than the light-emitting layer, the EL layer 203 may further have a layer containing a substance with high hole-injecting property, a substance with high hole-transporting property, a hole-blocking material, a substance with high electron -transporting property, a substance with high electron-injecting property, or a bipolar substance (a substance with high electron-transporting property and high hole-transporting property), etc.

[0096] Known substances can be used for the EL layer 203, and either low molecular weight compounds or high molecular weight compounds can be used, and it may contain inorganic compounds. In this embodiment, the EL layer 203 contains an organic compound according to one aspect of the present invention. The organic compound according to one aspect of the present invention is a substance with high hole-transporting property, and thus can be used for a hole-transporting layer or a light-emitting layer.

[0097] A specific configuration example of the EL layer 203 is shown in Fig. 1(B). In the EL layer 203 shown in Fig. 1(B) , a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, an electron transport layer 304, and an electron injection layer 305 are laminated in this order from the side of the first electrode 201.

[0098] The light-emitting element shown in Fig. 1(C) has an EL layer 20 3 between the first electrode 201 and the second electrode 205, and further has an intermediate layer 207 between the EL layer 203 and the second electrode 205.

[0099] A specific configuration example of the intermediate layer 207 is shown in FIG. 1(D). The intermediate layer 207 has at least the charge generation region 3 08. As a layer other than the charge generation region 308, the intermediate layer 207 may further have an electron relay layer 307 and an electron injection buffer layer 306. In FIG. 1(D) , an EL layer 203 is provided on the first electrode 201, the intermediate layer 207 is provided on the EL layer 203, and a second electrode 205 is provided on the intermediate layer 207. Also, in FIG. 1(D), as the intermediate layer 207 , an electron injection buffer layer 306, an electron relay layer 307, and a charge generation region 308 are provided from the EL layer 203 side.

[0100] When a voltage higher than the threshold voltage of the light-emitting element is applied between the first electrode 201 and the second electrode 205, holes and electrons are generated in the charge generation region 308. The holes move to the second electrode 205, and the electrons move to the electron relay layer 307. The electron relay layer 307 has high electron transportability and is a layer that quickly transfers the electrons generated in the charge generation region 308 to the electron injection buffer layer 306. The electron injection buffer layer 306 relaxes the barrier for injecting electrons into the EL layer 203 and is a layer that enhances the electron injection efficiency into the EL layer 203. Therefore, the electrons generated in the charge generation region 308 are injected into the LUM O level (lowest unoccupied molecular orbital level) of the EL layer 203 through the electron relay layer 307 and the electron injection buffer layer 306.

[0101] Also, the electron relay layer 307 can prevent interactions such as the substances constituting the charge generation region 308 and the substances constituting the electron injection buffer layer 306 reacting at the interface and impairing each other's functions.

[0102] Between the first electrode 201 and the second electrode 205, like the light-emitting elements shown in FIGS. 1(E) and 1(F) A plurality of EL layers may be stacked. In this case, an intermediate layer 207 is preferably provided between the stacked EL layers. For example, the light-emitting element shown in FIG. 1(E) has an intermediate layer 207 between the first EL layer 2 03a and the second EL layer 203b. Also, the light-emitting element shown in FIG. 1(F) has n EL layers (n is a natural number of 2 or more), and an intermediate layer 207 is provided between the m-th EL layer 203(m)

[0103] and the (m + 1)-th EL layer 203(m + 1). The behavior of electrons and holes in the intermediate layer 207 provided between the EL layer 203(m) and the EL layer 203(m + 1) will be described. When a voltage higher than the threshold voltage of the light-emitting element is applied between the first electrode 201 and the second electrode 205, holes and electrons are generated in the intermediate layer 207, and the holes move to the EL layer 203(m + 1) provided on the second electrode 205 side, and the electrons move to the EL layer 203(m) provided on the first electrode 201 side. The holes injected into the EL layer 203(m + 1) recombine with the electrons injected from the second electrode 205 side, and the light-emitting substance contained in the EL layer 203( m + 1) emits light. Also, the electrons injected into the EL layer 203(m) recombine with the holes injected from the first electrode 201 side, and the light-emitting substance contained in the EL layer 203(m) emits light. Therefore, the holes and electrons generated in the intermediate layer 207 each lead to light emission in different EL layers. When the same configuration as the intermediate layer is formed between the EL layers by providing the EL layers in contact with each other,

[0104] the EL layers can be provided in contact with each other. For example, when a charge generation region is formed on one surface of the EL layer, an EL layer can be provided in contact with that surface.

[0105] ​​ Also, by making the emission colors of the respective EL layers different, it is possible to obtain emission of a desired color for the entire light-emitting element. For example, in a light-emitting element having two EL layers, by making the emission color of the first EL layer and the emission color of the second EL layer be in a complementary color relationship, it is also possible to obtain a light-emitting element that emits white light as the entire light-emitting element. Note that complementary colors refer to the relationship between colors that become achromatic when mixed. That is, when light obtained from substances that emit colors in a complementary color relationship is mixed, white light can be obtained. Also, the same applies to a light-emitting element having three or more EL layers.

[0106] FIGS. 1(A) to (F) can be used in combination with each other. For example, an intermediate layer 207 can also be provided between the second electrode 205 and the EL layer 203(n) of FIG. 1(F).

[0107] Hereinafter, materials that can be used for each layer are exemplified. Note that each layer is not limited to a single layer, and two or more layers may be stacked.

[0108] 〈Anode〉 The electrode that functions as the anode (the first electrode 201 in the present embodiment) can be formed by using one or more of a conductive metal, an alloy, a conductive compound, etc. In particular, it is preferable to use a material having a large work function (4.0 eV or more). For example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, gold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, or a nitride of a metal material (for example, titanium nitride), etc. are listed. ​​​​​​​​​​​ is irradiated.

[0109] When the anode is in contact with the charge generation region, various conductive materials can be used without considering the work function value. For example, aluminum, silver, alloys containing aluminum, etc. can also be used.

[0110] 〈Cathode〉 The electrode (the second electrode 205 in this embodiment) that functions as the cathode can be formed by using one or more of a conductive metal, alloy, conductive compound, etc. In particular, it is preferable to use a material with a small work function (3.8 eV or less). For example, elements belonging to Group 1 or Group 2 of the periodic table (e.g., alkali metals such as lithium and cesium, alkaline earth metals such as calcium and strontium, magnesium, etc.), alloys containing these elements (e.g., Mg-Ag, Al-Li), rare earth metals such as europium and ytterbium, alloys containing these rare earth metals, aluminum, silver, etc. can be used.

[0111] When the cathode is in contact with the charge generation region, various conductive materials can be used without considering the work function value. For example, indium tin oxide containing ITO, silicon, or silicon oxide, etc. can

[0112] also be used.

[0112] The light-emitting element may be configured such that one of the anode or the cathode is a conductive film that transmits visible light and the other is a conductive film that reflects visible light, or it may be configured such that both the anode and the cathode are conductive films that transmit visible light.

[0113] The conductive film that transmits visible light is, for example, indium oxide, ITO, indium zinc oxide, It can be formed using zinc oxide, zinc oxide added with gallium, etc. Also, gold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, or metal materials such as titanium, or nitrides of these metal materials (e.g., titanium nitride), etc. can also be used by forming them thinly to have light transmittance. Also, graphene, etc. can be used.

[0114] The conductive film that reflects visible light is, for example, made of metal materials such as aluminum, gold, platinum, silver, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, or palladium, alloys of aluminum and titanium, alloys of aluminum and nickel, alloys of aluminum and neodymium such as alloys containing aluminum (aluminum alloys), or alloys containing silver such as alloys of silver and copper. An alloy of silver and copper is preferable because of its high heat resistance. Also, lanthanum, neodymium, or germanium, etc. may be added to the above metal materials or alloys. It is also okay.

[0115] The electrodes can be formed using vacuum evaporation method or sputtering method respectively. Also, when using silver paste, etc., coating method or inkjet method can be used.

[0116] 〈Hole injection layer 301〉 The hole injection layer 301 is a layer containing a substance with high hole injection property.

[0117] Examples of substances with high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium nium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. ​Oxides and the like can be used.

[0118] In addition, phthalocyanine-based compounds such as phthalocyanine (abbreviation: H2Pc), copper(II) phthalocyanine (abbreviation: CuPc ) can be used.

[0119] In addition, 4,4’,4’’-tris(N,N-diphenylamino ) triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-meth ylphenyl)-N-phenylamino] triphenylamine (abbreviation: MTDATA), 4 ,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino] biphen yl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)- N’-phenylamino] phenyl}-N-phenylamino) biphenyl (abbreviation: DNTP D), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylami no] benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl )-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3, 6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9- phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-( 9-phenylcarbazol-3-yl) amino]-9-phenylcarbazole (abbreviation: P CzPCN1) and other aromatic amine compounds can be used.

[0120] In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenyl lamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylami [[4-(aminomethyl)phenyl]phenyl-N'-phenylamino]phenyl methacrylamide](abbreviation : PTPDMA), polymers such as poly[N,N'-bis(4-butylphenyl)-N,N'-bis( phenyl)benzidine](abbreviation: Poly-TPD), poly(3,4- ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS), etc. can be used.

[0121] Also, the hole injection layer 301 may be used as a charge generation region. When the hole injection layer 301 in contact with the anode is the charge generation region, various conductive materials can be used for the anode without considering the work function. The materials constituting the charge generation region will be described later.

[0122] 〈Hole transport layer 302〉 The hole transport layer 302 is a layer containing a substance with high hole transport properties. The organic compound of one aspect of the present invention has high hole transport properties and can be preferably used for the hole transport layer 302.

[0123] As the substance with high hole transport properties, any substance with higher hole transport properties than electrons can be used, especially , preferably a substance having a hole mobility of 10 -6 cm 2 / Vs or more.

[0124] Also, in the hole transport layer 302, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: TPD), etc. Minn (abbreviation: BPAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2 -yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis [N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl such as (abbreviation: BSPB) and other aromatic amine compounds can be used.

[0125] In addition, 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(1 0-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA ), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H- carbazole (abbreviation: PCzPA) and other carbazole derivatives can be used.

[0126] In addition, 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t- BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10 -diphenylanthracene (abbreviation: DPAnth) and other aromatic hydrocarbon compounds can be used as well.

[0127] In addition, polymer compounds such as PVK, PVTPA, PTPDMA, Poly-TPD can be used as well.

[0128] 〈Light-emitting layer 303〉 The light-emitting layer 303 is a layer containing a light-emitting substance. As the light-emitting substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. Here is an example of a fluorescent compound that can be used in the light-emitting layer 303. For example, a blue-emitting

[0129] light-emitting As materials, N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N, N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H- carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl- 9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be mentioned. Also, as green-emitting materials, N-(9,10-diphenyl-2-anthryl)- N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA ), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N ,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4- phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl- 2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl- 2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), etc. can be mentioned. Also, as yellow-emitting materials, rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,1 1-diphenyltetracene (abbreviation: BPT), etc. can be mentioned. Also, as red-emitting materials, N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11- diamine​ Diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N’,N’-tetra rakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-di amine (abbreviation: p-mPhAFD), etc. are exemplified.

[0130] An example of a phosphorescent compound that can be used in the light-emitting layer 303 is given. For example, as a phosphorescent compound having a peak of emission at 440 nm to 520 nm, tris{2-[5-(2-meth thylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazole -3-yl-κN2]phenyl-κC}iridium(III) (abbreviation: [Ir(mppt z-dmp)3]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-t riazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), tris[4-( 3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato iridium(III) (abbreviation: [Ir(iPrptz-3b)3]) such as 4H-t riazole skeleton-containing organometallic iridium complexes, and tris[3-methyl-1-(2-meth thylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III )(abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3 -propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir( Prptz1-Me)3]) such as 1H-triazole skeleton-containing organometallic iridium m complexes, and fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl- 1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]), t Lis[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanth trinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]) and other organometallic iridium complexes having an imidazole skeleton, and bis[2-(4’,6’-di fluorophenyl)pyridinato-N,C 2’ iridium(III) tetrakis(1-py razolyl)borate (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl )pyridinato-N,C 2’ iridium(III) picolinate (abbreviation: FIrpic) , bis{2-[3’,5’-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic) ), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C 2’ iridi um(III) acetylacetonate (abbreviation: FIrracac) and other organometallic iridium complexes having an electron-withdrawing group such as can be mentioned. Among the above-mentioned , organometallic iridium complexes having a 4H-triazole skeleton are particularly preferred because of their excellent reliability and luminescence efficiency.

[0131] In addition, for example, as a phosphorescent compound having a luminescence peak at 520 nm to 600 nm, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir (mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iridium (III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis(6- methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm) 2(acac)]), (acetylacetonato)bis(6-tert-butyl-4-phenyl pyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac) ), (acetylacetonato)bis[4-(2-norbornyl)-6-phenylpyrimido nato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (ace tylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimido nato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)]), ( (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III)( abbreviation: [Ir(dppm)2(acac)]) and other organometallic iridium complexes having a pyrimidine skeleton, (acetylacetonato)bis(3,5-dimethyl-2-phenylpyra dinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato )iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) and such organometallic iridium complexes having a pyrazine skeleton, tris(2-phenylpyridinato- N,C 2’ )iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-pheny lpyridinato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir (ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzo h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris(2- phenylquinolinato-N,C 2’) Iridium(III) (abbreviation: [Ir(pq)3]) , bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetonate Organometallic compounds with pyridine skeletons such as Ir(pq)2(acac) In addition to iridium complexes, tris(acetylacetonato)(monophenanthroline)terbiu Rare earth metal complexes such as Tb(III) (abbreviation: [Tb(acac)3(Phen)]) Among the above, organometallic iridium complexes having a pyrimidine skeleton are reliable. Since the light-emitting diode is particularly preferable because of its excellent light-emitting properties and luminous efficiency.

[0132] For example, phosphorescent materials having an emission peak at 600 nm to 700 nm include Diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]i Ir(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6 -Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(I II) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di(naphthalene (1-phenyl-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: Organometallic iridates with pyrimidine skeletons, such as [Ir(d1npm)2(dpm)] (acetylacetonato)bis(2,3,5-triphenylpyrazinate)yl complexes Ir(tppr)2(acac)], bis(2,3,5- Triphenylpyrazinate)(dipivaloylmethanato)iridium(III)(abbreviation: [I r(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-furan [Ir(Fdpq)2 Organometallic iridium complexes having a pyrazine skeleton such as (acac)]), and tris(1 -phenylisoquinolinato-N,C 2’ )iridium(III) (abbreviation: [Ir(piq )3]), bis(1-phenylisoquinolinato-N,C 2’ )iridium(III) acetate Chloroacetonate (abbreviation: [Ir(piq)2(acac)]) and other organometallic iridium complexes having a pyridine skeleton, 2,3,7,8,12,13,17,18-octa ethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) and other platinum complexes, and tris(1,3-diphenyl-1,3-propanedionato)(monophenanthro line) europium(III) (abbreviation: [Eu(DBM)3(Phen)]), tris 1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline ) europium(III) (abbreviation: [Eu(TTA)3(Phen)]) and other rare earth metal complexes. Among the above, organometallic iridium complexes having a pyrimidine skeleton are particularly preferred because of their outstanding reliability and luminescence efficiency. In addition, organometallic iridium complexes having a pyrazine skeleton can obtain red luminescence with good chromaticity.

[0133] In addition, a polymer compound can also be used for the light-emitting layer 303. For example, as a blue light-emitting material, poly(9,9-dioctylfluorene-2,7-diyl) (abbreviation: PFO), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,5-dimethoxy sibenzen-1,4-diyl)] (abbreviation: PF-DMOP), poly{(9,9-dioctyl fluorene-2,7-diyl)-co-[N,N’-di-(p-butylphenyl)-1 , 4-diaminobenzene] (abbreviation: TAB-PFH), etc. can be mentioned. Also, as the green-emitting luminescent material, poly(p-phenylenevinylene) (abbreviation: PPV), poly[(9,9- dihexylfluorene-2,7-diyl)-alt-co-(benzo[2,1,3]thiadiazole-4,7-diyl)] (abbreviation: PFBT), poly[(9,9-dioctyl-2 ,7-divinylenefluorenylene)-alt-co-(2-methoxy-5-(2-ethylhexyl oxy)-1,4-phenylene)], etc. can be mentioned. Also, as the orange to red-emitting luminescent material, poly[2-methoxy-5-(2'-ethylhexoxy)-1,4-phenylene vinylene] (abbreviation: MEH-PPV), poly(3-butylthiophene-2,5-diyl) (abbreviation: R4-PAT), poly{[9,9-dihexyl-2,7-bis(1-cyanovinylene fluorenylene]-alt-co-[2,5-bis(N,N'-diphenylamino )-1,4-phenylene]}, poly{[2-methoxy-5-(2-ethylhexoxy) -1,4-bis(1-cyanovinylenephenylene)]-alt-co-[2,5-bis( N,N'-diphenylamino)-1,4-phenylene]}(abbreviation: CN-PPV-DPD ) etc. can be mentioned.

[0134] Note that the light-emitting layer 303 may have a structure in which a luminescent substance (guest material) is dispersed in another substance (host material). As the host material, various materials can be used, and it is preferable to use a substance with a higher LUMO level and a lower highest occupied molecular orbital level (HOMO level) than the guest material. By adopting a structure in which the guest material is dispersed in the host material, crystallization of the light-emitting layer 30 3 can be suppressed. Also, concentration quenching due to a high concentration of the guest material can be prevented. can be suppressed.

[0135] As the host material, the above-mentioned substances with high hole transport properties (for example, aromatic amine compounds and car bazole derivatives), and the substances with high electron transport properties described later (for example, metal complexes having a quinoline skeleton or a benzoquinoline skeleton, and metal complexes having an oxazole-based ligand or a thiazole-based ligand) can be used. Since the organic compound of one aspect of the present invention has high hole transport properties, it can be suitably used as a host material. In addition, as the host material, tris( 8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8 -quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxy benzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis[2-(2 -hydroxyphenyl)pyridinato]zinc (abbreviation: Znpp2), bis(2-methyl-8 -quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq ), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzo oxazolyl)phenolato]zinc(II) (abbreviation: Zn(BOX)2), bis[2-(2 -benzothiazolyl)phenolato]zinc(II) (abbreviation: Zn(BTZ)2) and other metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4- oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl )-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3- (4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2 triazole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetri azole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetri azole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetri (4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2 ,4-triazole (abbreviation: TAZ), 2,2’,2’’-(1,3,5-benzenetri 1H-benzoimidazole (TPBI), Heterocyclization of phenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), etc. Compounds, CzPA, 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl )phenyl]-9H-carbazole (abbreviation: DPCzPA) and other carbazole derivatives, NA, t-BuDNA, DPAnth, 9,10-bis(3,5-diphenylphenyl) Anthracene (abbreviation: DPPA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(Stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9' -(Stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3' ,3''-(benzene-1,3,5-triyl)tripylene (abbreviation: TPB3), 6,1 Aromatic hydrocarbon compounds such as 2-dimethoxy-5,11-diphenylchrysene or condensed aromatic Aromatic compound, N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl] 10-phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), -9-Anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N -[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-a PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl- 9-Anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PC APBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9 H-Carbazole-3-amine (abbreviation: 2PCAPA), NPB, TPD, DFLDPB Aromatic amine compounds such as i and BSPB can be used.

[0136] In addition, compounds having an arylamine skeleton such as 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenyl amine (abbreviation: PCBA1BP), PCzPCN1, 2,3-bis(4-diphenyl aminophenyl)quinoxaline (abbreviation: TPAQn), carbazole derivatives such as CBP, 4,4',4''-tris(N-carbazolyl)triphenylamine (abbreviation: TCTA), etc., nitrogen-containing heteroaromatic compounds such as 2-[3-(dibenzothiophen-4-yl phenyl]dibenz[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenz[f, h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[4-(3,6-diphenyl -9H-carbazol-9-yl)phenyl]dibenz[f,h]quinoxaline (abbreviation: 2CzPDBq-III), etc. can be used. Further, a polymer compound such as PVK can also be used. In addition, a plurality of types of host materials can be used. For example, in order to suppress crystallization, a substance that suppresses crystallization such as rubrene etc. may be further added. Also, in order to perform energy transfer to the guest material more efficiently, NPB, or Alq etc. may be further added.

[0137] In addition, by providing a plurality of light-emitting layers and making the emission colors of each layer different, it is possible to obtain light emission of a desired color as the entire light-emitting element. For example, in a light-emitting element having two light-emitting layers, make the emission color of the first light-emitting layer and the emission color of the second light-emitting layer be in a complementary color relationship.

[0138] ​Thus, it is also possible to obtain a light-emitting element that emits white light as a whole. Also, the light-emitting layer The same applies to a light-emitting element having three or more light-emitting layers.

[0139] 〈Electron transport layer 304〉 The electron transport layer 304 is a layer containing a substance with high electron transport properties.

[0140] As the substance with high electron transport properties, an organic compound with higher electron transport properties than hole transport properties may be used. In particular, it is preferably a substance having an electron mobility of 10 -6 cm 2 / Vs or more.

[0141] For example, metal complexes such as Alq, Almq3, BeBq2, BAlq, Zn(BOX)2, Zn(BTZ )2 can be used.

[0142] Also, heteroaromatic compounds such as PBD, OXD-7, TAZ, BPhen, BCP, 3-(4-tert-butyl phenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-tri azole (abbreviation: p-EtTAZ), 4,4'-bis(5-methylbenzoxazol- 2-yl)stilbene (abbreviation: BzOs) can be used. 。

[0143] Also, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl fluorene-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) can be used. 。

[0144] 〈Electron injection layer 305〉 The electron injection layer 305 is a layer containing a substance with high electron injection properties.

[0145] As substances with high electron injection properties, for example, lithium, cesium, calcium, lithium oxide, lithium carbonate, cesium carbonate, lithium fluoride, cesium fluoride, calcium fluoride, erbium fluoride, etc., such as alkali metals, alkaline earth metals, rare earth metals, or compounds of these (oxides, carbonates, halides, etc.) can be used.

[0146] Also, the electron injection layer 305 may have a structure containing the aforementioned substance with high electron transport properties and a donor substance. For example, the electron injection layer 3 05 may be formed by containing magnesium (Mg) in Alq. When containing a substance with high electron transport properties and a donor substance, the mass ratio of the addition amount of the donor substance to the substance with high electron transport properties is preferably in the ratio of 0.001 or more and 0.1 or less.

[0147] As donor substances, lithium, cesium, magnesium, calcium, erbium, ytterbium, lithium oxide, calcium oxide, barium oxide, magnesium oxide, etc., such as alkali metals, alkaline earth metals, rare earth metals, or compounds of these (oxides), Lewis bases, and in addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF), tetrathianaphthacene (abbreviation: TTN), nickelocene, decamethylnickelocene, etc. can be used.

[0148] 〈Charge generation region〉 The charge generation region constituting the hole injection layer and the charge generation region 308 are regions containing a substance with high hole transport properties and an acceptor substance (electron acceptor). The acceptor substance is a hole transport It is preferably added in a ratio of 0.1 or more and 4.0 or less by mass to a highly conductive substance. Preferably.

[0149] In addition, the charge generation region may contain a substance with high hole transportability and an acceptor substance not only in the same film, but also when a layer containing a substance with high hole transportability and a layer containing an acceptor substance are laminated. However, when the charge generation region is provided on the cathode side, a layer containing a substance with high hole transportability is in contact with the cathode, and in the case of a laminated structure where the charge generation region is provided on the anode side, a layer containing an acceptor substance is in contact with the anode.

[0150] As the substance with high hole transportability, an organic compound with higher hole transportability than electrons may be used. In particular, -6 cm 2 / Vs or more, and it is preferably an organic compound having a hole mobility. Preferably.

[0151] Specifically, the organic compound of one aspect of the present invention, aromatic amine compounds such as NPB and BPAFLP, carbazole derivatives such as CBP, CzPA, and PCzPA, aromatic hydrocarbon compounds such as t-BuDNA, DNA, DPAnth, and polymer compounds such as PVK and PVTPA, etc., substances with high hole transportability exemplified as substances that can be used in the hole transport layer 302 can be used.

[0152] Examples of the acceptor substance include 7,7,8,8-tetracyano-2,3,5,6-tetra fluoroquinodimethane (abbreviation: F4-TCNQ), organic compounds such as chloranil, transition metal oxides, and metal oxides belonging to Groups 4 to 8 in the periodic table of elements can be mentioned. That is, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferred because they have high electron-accepting properties. In particular, molybdenum oxide is preferred because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle.

[0153] 〈Electron injection buffer layer 306〉 The electron injection buffer layer 306 is a layer containing a substance with high electron injection properties. The electron injection buffer layer 306 facilitates the injection of electrons from the charge generation region 308 to the EL layer 203. As a substance with high electron injection properties, the aforementioned materials can be used. In addition, the electron injection buffer layer 306 may also have a configuration containing the aforementioned substance with high electron transport properties and a donor substance.

[0154] 〈Electron relay layer 307〉 In the electron relay layer 307, electrons extracted by the acceptor substance in the charge generation region 308 are quickly received.

[0155] The electron relay layer 307 contains a substance with high electron transport properties. As the substance with high electron transport properties, it is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0156] Specific examples of the phthalocyanine-based material include CuPc, SnPc (Phthalocy anine tin(II) complex), ZnPc (Phthalocyani ne zinc complex), CoPc (Cobalt(II)phthaloc yanine, β-form), FePc (Phthalocyanine Iron ), PhO-VOPc (Vanadyl 2,9,16,23-tetraphenox​​​​ Examples include y-29H,31H-phthalocyanine).

[0157] As the metal complex having the metal-oxygen bond and the aromatic ligand, it is preferable to use a metal complex having a metal-oxygen double bond. Since the metal-oxygen double bond has acceptor properties, the transfer (donation / acceptance) of electrons becomes easier.

[0158] In addition, as the metal complex having the metal-oxygen bond and the aromatic ligand, phthalocyanine-based materials are preferable. In particular, VOPc (Vanadyl phthalocyanine), S nOPc (Phthalocyanine tin(IV) oxide comple x), TiOPc (Phthalocyanine titanium oxide c omplex) are preferable because the metal-oxygen double bond in the molecular structure easily acts on other molecules and has high acceptor properties.

[0159] As the phthalocyanine-based material, those having a phenoxy group are preferable. Specifically, phthalocyanine derivatives having a phenoxy group such as P hO-VOPc are preferable. Phthalocyanine derivatives having a phenoxy group are soluble in a solvent, so they have the advantages of being easy to handle in forming a light-emitting device and being easy to maintain the apparatus used for film formation.

[0160] In addition, as other substances having high electron transport properties, for example, 3,4,9,10-perylenetet racarboxylic dianhydride (abbreviation: PTCDA), 3,4,9,10-perylenetetracarbo xylic bisbenzimidazole (abbreviation: PTCBI), N,N’-dioctyl-3, ​​​​​4,9,10-Perylenetetracarboxylic diimide (abbreviation: PTCDI-C8H), N, N’-dihexyl-3,4,9,10-perylenetetracarboxylic diimide (abbreviation: He x PTC) and other perylene derivatives, pyrazino[2,3-f][1,10]phenanthro line-2,3-dicarbonitrile (abbreviation: PPDN), 2,3,6,7,10,11-he xacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT(C N)6), 2,3-diphenylpyrido[2,3-b]pyrazine (abbreviation: 2PYPR), 2 ,3-bis(4-fluorophenyl)pyrido[2,3-b]pyrazine (abbreviation: F2PYP R) and other nitrogen-containing condensed aromatic compounds may also be used. Since nitrogen-containing condensed aromatic compounds are stable, they are preferred as materials used to form the electron relay layer 307.

[0161] In addition, 7,7,8,8-tetracyanoquinodimethane (abbreviation: TCNQ), 1,4,5,8 -naphthalenetetracarboxylic dianhydride (abbreviation: NTCDA), perfluoropentacene , copper hexadecafluorophthalocyanine (abbreviation: F 16 CuPc), N,N’-bis(2 ,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooct yl)-1,4,5,8-naphthalenetetracarboxylic diimide (abbreviation: NTCDI-C 8F), 3’,4’-dibutyl-5,5’’-bis(dicyanomethylene)-5,5’’- dihydro-2,2’:5’,2’’-terthiophene (abbreviation: DCMT), methanofuller ene (for example, [6,6]-phenyl C 61 butyrate methyl ester), etc. can be used.

[0162] ​The electron relay layer 307 may further contain the above-described donor material. By including a donor material in the electron relay layer 3 07, the movement of electrons becomes easier, and the light-emitting element can be driven at a lower voltage.

[0163] The LUMO levels of the material with high electron-transporting properties and the donor material are set to be between the LUMO level of the acceptor material contained in the charge generation region 308 and the LUMO level of the material with high electron-transporting properties contained in the electron transport layer 304 (or the LUMO level of the EL layer 203 with which the electron relay layer 307 is in contact (via the electron injection buffer layer 306)). The LUMO level is preferably -5 .0 eV or higher and -3.0 eV or lower. When a donor material is included in the electron relay layer 307, a material having a LUMO level higher than the acceptor level of the acceptor material contained in the charge generation region 308 can be used as the material with high electron-transporting properties.

[0164] Note that the layers constituting the above-described EL layer 203 and the intermediate layer 207 can be formed by methods such as vapor deposition (including vacuum vapor deposition), transfer printing, printing, inkjet printing, and coating.

[0165] Using the light-emitting element shown in this embodiment, a passive matrix type light-emitting device or an active matrix type light-emitting device in which the driving of the light-emitting element is controlled by a transistor can be manufactured. Further, the light-emitting device can be applied to an electronic device, a lighting device, or the like.

[0166] This embodiment can be freely combined with other embodiments.

[0167] (Embodiment 3) ​​​​​​​​​​In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to FIG. 2.

[0168] The light-emitting element shown in FIG. 2 has an EL layer 203 between a first electrode 201 and a second electrode 205. The EL layer 203 includes at least a light-emitting layer 213 containing a first organic compound 221, a second organic compound 222, and a phosphorescent compound 223. The EL layer 203 may further include, as layers other than the light-emitting layer 213, a substance with high hole injection property, a substance with high hole transport property, a hole blocking material, a substance with high electron transport property, a substance with high electron injection property, or a bipolar substance (a substance with high electron transport property and high hole transport property), etc. The phosphorescent compound 223 is a guest material in the light-emitting layer 213. In this embodiment, the one with a higher proportion contained in the light-emitting layer 213 among the first organic compound 221 and the second organic compound 222 is used as the host material in the light-emitting layer 213. The organic compound according to one aspect of the present invention can be suitably used as the first organic compound 221 or the second organic compound 222. By adopting a configuration in which the above guest material is dispersed in the host material in the light-emitting layer 213, crystallization of the light-emitting layer can be suppressed. Also, concentration quenching due to a high concentration of the guest material can be suppressed, and the light-emitting efficiency of the light-emitting element can be increased.

[0169] Note that the triplet excitation energy level (T1 level) of each of the first organic compound 221 and the second organic compound 222 is preferably higher than the T1 level of the phosphorescent compound 223. The T1 level of the first organic compound 221 (or the second organic compound 222) is preferably higher than the T1 level of the phosphorescent compound 223. The one with a higher proportion contained in the light-emitting layer 213 among the first organic compound 221 and the second organic compound 222 is used as the host material in the light-emitting layer 213. The organic compound according to one aspect of the present invention can be suitably used as the first organic compound 221 or the second organic compound 222.

[0170] In the light-emitting layer 213, by adopting a configuration in which the above guest material is dispersed in the host material, crystallization of the light-emitting layer can be suppressed. Also, concentration quenching due to a high concentration of the guest material can be suppressed, and the light-emitting efficiency of the light-emitting element can be increased. Note that the triplet excitation energy level (T1 level) of each of the first organic compound 221 and the second organic compound 222 is preferably higher than the T1 level of the phosphorescent compound 223.

[0171] Note that the triplet excitation energy level (T1 level) of each of the first organic compound 221 and the second organic compound 222 is preferably higher than the T1 level of the phosphorescent compound 223. The T1 level of the first organic compound 221 (or the second organic compound 222) is preferably higher than the T1 level of the phosphorescent compound 223. The T1 level of the first organic compound 221 (or the second organic compound 222) is preferably higher than the T1 level of the phosphorescent compound 223. If it is lower than the T1 level of 23, the triplet excitation energy of the phosphorescent compound 223 that contributes to luminescence is quenched by the first organic compound 221 (or the second organic compound 222), resulting in a decrease in luminescence efficiency. ー, which causes a decrease in the luminescence efficiency.

[0172] Here, in order to increase the energy transfer efficiency from the host material to the guest material, considering the Förster mechanism (dipole-dipole interaction) and Dexter mechanism (electron exchange interaction) known as intermolecular transfer mechanisms, when discussing the energy transfer from the singlet excited state of the host material's luminescence spectrum (fluorescence spectrum when discussing energy transfer, phosphorescence spectrum when discussing energy transfer from the triplet excited state), it is preferable that the overlap with the absorption spectrum of the guest material (more specifically, the spectrum in the absorption band on the longest wavelength (low energy) side) is large.

[0173] However, usually, it is difficult to overlap the fluorescence spectrum of the host material with the absorption spectrum in the absorption band on the longest wavelength (low energy) side of the guest material. Because if it is done in that way, the phosphorescence spectrum of the host material is located on the longer wavelength (lower energy) side than the fluorescence spectrum, so the T1 level of the host material is lower than the T1 level of the phosphorescent compound, causing the quenching problem described above. On the other hand, in order to avoid the quenching problem, if the host material is designed so that its T1 level is higher than the T1 level of the phosphorescent compound, then the fluorescence spectrum of the host material shifts to the shorter wavelength (higher energy) side, and its fluorescence spectrum no longer overlaps with the absorption spectrum in the absorption band on the longest wavelength (low energy) side of the guest material. Therefore, overlapping the fluorescence spectrum of the host material with the absorption spectrum of the guest material​​​​​​​​​​​​​​ Overlap with the absorption spectrum in the absorption band on the longest wavelength (low energy) side, and one of the host materials It is usually difficult to maximize the energy transfer from the singlet excited state.

[0174] Therefore, in one aspect of the present invention, the first organic compound 221 and the second organic compound 222 Preferably form a combination that forms an exciplex (also referred to as an exciplex). In this case, when carriers (electrons and holes) recombine in the light-emitting layer 213, the first The organic compound 221 and the second organic compound 222 form an exciplex. As a result, light emission In the layer 213, the fluorescence spectrum of the first organic compound 221 and the second organic compound 22 The fluorescence spectrum of 2 is converted into the emission spectrum of the exciplex located on the longer wavelength side . And, by selecting the first organic compound and the second organic compound so that the overlap between the emission spectrum of the exciplex and the absorption spectrum of the guest material is large, The energy transfer from the singlet excited state can be maximized. Regarding the triplet excited state as well, it is considered that energy transfer occurs from the exciplex rather than the host material.

[0175] As the phosphorescent compound 223, for example, the phosphorescent compounds listed in Embodiment 2 can be used. In addition, as the first organic compound 221 and the second organic compound 222, any combination that produces an exciplex may be used, but a combination of a compound that easily accepts electrons (an electron trap compound) and a compound that easily accepts holes (a hole trap compound) Is preferred.

[0176] Examples of compounds that easily accept electrons include π-electron deficient compounds such as nitrogen-containing heteroaromatic compounds. ​​​​A metal complex having a polycyclic aromatic compound, a quinoline skeleton or a benzoquinoline skeleton, an oxazole system ligand or a metal complex having a thiazole system ligand can be used.

[0177] Specifically, metal complexes such as BeBq2, BAlq, Znq, Zn(BOX)2, Zn(BTZ)2, etc. of metal complexes, PBD, TAZ, OXD-7, 9-[4-(5-phenyl-1,3,4-oxa diazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2, 2’,2’’-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzo imidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phe nyl]-1-phenyl-1H-benzoimidazole (abbreviation: mDBTBIm-II), etc. heterocyclic compounds having a polyazole skeleton, 2mDBTPDBq-II, 2mDBTBP DBq-II, 2CzPDBq-III, 7-[3-(dibenzothiophen-4-yl) phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxali ne (abbreviation: 6mDBTPDBq-II), 2-[3’-(9H-carbazol-9-yl )biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq ) and other heterocyclic compounds having a quinoxaline skeleton or a dibenzoquinoxaline skeleton, 4,6 -bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPn P2Pm), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidi ne (abbreviation: 4,6mCzP2Pm), 4,6-bis[3-(4-dibenzothienyl)phe Diazine compounds having a diazine skeleton (pyrimidine skeleton, pyrazine skeleton, etc.) such as nil pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 3,5-bis[3-(9H-carbazol- yl-9-yl)phenyl]pyridine (abbreviation: 3,5DCzPPy), 1,3,5-tri [3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), 3,3’,5,5 ’-tetra[(m-pyridyl)-phen-3-yl]biphenyl (abbreviation: BP4mPy) and other heterocyclic compounds having a pyridine skeleton can be mentioned. Among the above, heterocyclic compounds having a quinoxaline skeleton or a dibenzoquinoxaline skeleton, heterocyclic compounds having a diazine skeleton, and heterocyclic compounds having a pyridine skeleton are preferable because of their good reliability. As a compound that easily receives holes, the organic compound of one aspect of the present invention can be preferably used.

[0178] In addition, π-electron-excessive heteroaromatic compounds (for example, carbazole derivatives and indole derivatives) and aromatic amine compounds can also be preferably used. For example, PCBA1BP , 4,4’-di(1-naphthyl)-4’’-(9-phenyl-9H-carbazol-3- yl)triphenylamine (abbreviation: PCBNBB), PCzPCN1, 4,4’,4’’ -tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1 ’-TNATA), 2,7-bis[N-(4-diphenylaminophenyl)-N-phenyl lamino]-spiro-9,9’-bifluorene (abbreviation: DPA2SF), N,N’-bis (9-phenylcarbazol-3-yl)-N,N’-diphenylbenzene-1,3-di amine (abbreviation: PCA2B), N-(9,9-dimethyl-2-diphenylamino-9H- etc. (Fluoren-7-yl)diphenylamine (abbreviation: DPNF), N,N’,N’’-tri Phenyl-N,N’,N’’-tris(9-phenylcarbazol-3-yl)benzene -1,3,5-triamine (abbreviation: PCA3B), 2-[N-(9-phenylcarbazol -3-yl)-N-phenylamino]spiro-9,9’-bifluorene (abbreviation: PCA SF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro- 9,9’-bifluorene (abbreviation: DPASF), N,N’-bis[4-(carbazol- 9-yl)phenyl]-N,N’-diphenyl-9,9-dimethylfluorene-2,7- diamine (abbreviation: YGA2F), TPD, DPAB, N-(9,9-dimethyl-9H-f luoren-2-yl)-N-{9,9-dimethyl-2-[N’-phenyl-N’-(9, 9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl} phenylamine (abbreviation: DFLADFL), PCzPCA1, 3-[N-(4-dipheny laminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCz DPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino no]-9-phenylcarbazole (abbreviation: PCzDPA2), DNTPD, 3,6-bis [N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-pheny lucarbazole (abbreviation: PCzTPN2), PCzPCA2, etc. can be mentioned.

[0179] The materials that can be used for the above-described first organic compound 221 and second organic compound 222 are not limited to these, and are combinations that can form an exciplex. The The emission spectrum overlaps with the absorption spectrum of the phosphorescent compound 223, and if the peak of the emission spectrum of the exciplex is at a longer wavelength than the peak of the absorption spectrum of the phosphorescent compound 223, it is preferable. it is preferable. it is preferable.

[0180] When the first organic compound 221 and the second organic compound 222 are composed of a compound that easily accepts electrons and a compound that easily accepts holes, the carrier balance can be controlled by the mixing ratio. Specifically, the range of the first organic compound: the second organic compound = 1:9 to 9:1 is preferable. When the first organic compound 221 and the second organic compound 222 are composed of a compound that easily accepts electrons and a compound that easily accepts holes, the carrier balance can be controlled by the mixing ratio. Specifically, the range of the first organic compound: the second organic compound = 1:9 to 9:1 is preferable. When the first organic compound 221 and the second organic compound 222 are composed of a compound that easily accepts electrons and a compound that easily accepts holes, the carrier balance can be controlled by the mixing ratio. Specifically, the range of the first organic compound: the second organic compound = 1:9 to 9:1 is preferable. When the first organic compound 221 and the second organic compound 222 are composed of a compound that easily accepts electrons and a compound that easily accepts holes, the carrier balance can be controlled by the mixing ratio. Specifically, the range of the first organic compound: the second organic compound = 1:9 to 9:1 is preferable.

[0181] The light-emitting device shown in this embodiment can increase the energy transfer efficiency by energy transfer utilizing the overlap between the emission spectrum of the exciplex and the absorption spectrum of the phosphorescent compound, and thus can realize a light-emitting device with high external quantum efficiency. The light-emitting device shown in this embodiment can increase the energy transfer efficiency by energy transfer utilizing the overlap between the emission spectrum of the exciplex and the absorption spectrum of the phosphorescent compound, and thus can realize a light-emitting device with high external quantum efficiency. The light-emitting device shown in this embodiment can increase the energy transfer efficiency by energy transfer utilizing the overlap between the emission spectrum of the exciplex and the absorption spectrum of the phosphorescent compound, and thus can realize a light-emitting device with high external quantum efficiency.

[0182] In one aspect of the present invention, as two other organic compounds of the phosphorescent compound 223 (guest material), a hole-trapping host molecule and an electron-trapping host molecule are used to form the light-emitting layer 213, and holes and electrons are introduced into the guest molecules present in the two host molecules to excite the guest molecules (that is, Guest Coupled with Complementary Hosts: GCCH) to obtain a configuration in which the light-emitting layer 213 is formed. In one aspect of the present invention, as two other organic compounds of the phosphorescent compound 223 (guest material), a hole-trapping host molecule and an electron-trapping host molecule are used to form the light-emitting layer 213, and holes and electrons are introduced into the guest molecules present in the two host molecules to excite the guest molecules (that is, Guest Coupled with Complementary Hosts: GCCH) to obtain a configuration in which the light-emitting layer 213 is formed. In one aspect of the present invention, as two other organic compounds of the phosphorescent compound 223 (guest material), a hole-trapping host molecule and an electron-trapping host molecule are used to form the light-emitting layer 213, and holes and electrons are introduced into the guest molecules present in the two host molecules to excite the guest molecules (that is, Guest Coupled with Complementary Hosts: GCCH) to obtain a configuration in which the light-emitting layer 213 is formed. In one aspect of the present invention, as two other organic compounds of the phosphorescent compound 223 (guest material), a hole-trapping host molecule and an electron-trapping host molecule are used to form the light-emitting layer 213, and holes and electrons are introduced into the guest molecules present in the two host molecules to excite the guest molecules (that is, Guest Coupled with Complementary Hosts: GCCH) to obtain a configuration in which the light-emitting layer 213 is formed. In one aspect of the present invention, as two other organic compounds of the phosphorescent compound 223 (guest material), a hole-trapping host molecule and an electron-trapping host molecule are used to form the light-emitting layer 213, and holes and electrons are introduced into the guest molecules present in the two host molecules to excite the guest molecules (that is, Guest Coupled with Complementary Hosts: GCCH) to obtain a configuration in which the light-emitting layer 213 is formed. In one aspect of the present invention, as two other organic compounds of the phosphorescent compound 223 (guest material), a hole-trapping host molecule and an electron-trapping host molecule are used to form the light-emitting layer 213, and holes and electrons are introduced into the guest molecules present in the two host molecules to excite the guest molecules (that is, Guest Coupled with Complementary Hosts: GCCH) to obtain a configuration in which the light-emitting layer 213 is formed.

[0183] At this time, as the hole-trapping host molecule and the electron-trapping host molecule, the above-described compound that easily accepts holes and the compound that easily accepts electrons can be used respectively. At this time, as the hole-trapping host molecule and the electron-trapping host molecule, the above-described compound that easily accepts holes and the compound that easily accepts electrons can be used respectively. At this time, as the hole-trapping host molecule and the electron-trapping host molecule, the above-described compound that easily accepts holes and the compound that easily accepts electrons can be used respectively.

[0184] This embodiment can be freely combined with other embodiments.

[0185] (Embodiment 4) In this embodiment, a light-emitting device according to one aspect of the present invention will be described with reference to FIG. 3. FIG. 3(A ) is a plan view showing a light-emitting device according to one aspect of the present invention, and FIG. 3(B) is a cross-sectional view taken along the dashed line A-B in FIG. 3(A).

[0186] The light-emitting device of this embodiment is surrounded by a support substrate 401, a sealing substrate 405, and a sealing material 407 in a space 415, and includes a light-emitting element 403 (a first electrode 421, an EL layer 423, and a second electrode 4 25). The light-emitting element 403 has a bottom emission structure. Specifically, it has a first electrode 421 that transmits visible light on the support substrate 401, an EL layer 423 on the first electrode 421, and a second electrode 425 that reflects visible light on the EL layer 423.

[0187] One aspect of the present invention is applied to the light-emitting element 403. Specifically, the light-emitting layer included in the EL layer 423 contains an organic compound according to one aspect of the present invention. Therefore, the light-emitting element 403 has a long lifespan. By applying one aspect of the present invention in this way, a highly reliable light-emitting device can be realized. .

[0188] The first terminal 409a is electrically connected to the auxiliary wiring 417 and the first electrode 421. An insulating layer 419 is provided in a region overlapping the auxiliary wiring 417 on the first electrode 421. The first terminal 409a and the second electrode 425 are electrically insulated by the insulating layer 419. The second terminal 409b is electrically connected to the second electrode 425. Note that in this embodiment 4 shows a configuration in which the first electrode 421 is formed on the auxiliary wiring 417. An auxiliary wiring 417 may be formed on the wiring 421 .

[0189] In addition, since organic EL elements emit light in an area with a higher refractive index than the atmosphere, the light is extracted into the atmosphere. When the organic EL element is heated, there are conditions that cause total reflection within the organic EL element or at the boundary between the organic EL element and the atmosphere. Therefore, there is a problem that the light extraction efficiency of the organic EL element is less than 100%.

[0190] Therefore, for example, a light extraction structure 411a is provided at the interface between the support substrate 401 and the atmosphere. It is preferable that the refractive index of the support substrate 401 is larger than that of the air. By providing a light extraction structure 411a at the interface of the support substrate 401, the light emitted from the support substrate 401 is prevented from being released into the atmosphere due to total reflection. The amount of light that cannot be extracted can be reduced, and the light extraction efficiency of the light emitting device can be improved.

[0191] In addition, the light-extraction structure 411b is provided at the interface between the light-emitting element 403 and the support substrate 401. is preferred.

[0192] However, if the first electrode 421 has unevenness, the EL layer 4 formed on the first electrode 421 may be damaged. Therefore, in this embodiment, a leakage current may occur in the EL layer 4. A planarization layer 413 having a refractive index equal to or greater than 23 is disposed in contact with the light extraction structure 411b. This allows the first electrode 421 to be a flat film, and the EL layer 423 This can suppress the occurrence of leakage current caused by the unevenness of the first electrode 421. In addition, since the light extraction structure 411b is provided at the interface between the planarization layer 413 and the support substrate 401, This reduces the amount of light that cannot be extracted to the atmosphere due to total reflection, and improves the light extraction efficiency of light-emitting devices. It can be done.

[0193] In FIG. 3(B), the support substrate 401, the light extraction structure 411a, and the light extraction structure 411b are shown as different elements, but the present invention is not limited to this. Two of these or all of them may be integrally formed. Further, by providing the light extraction structure 411b, no unevenness occurs on the first electrode 421 (for example, when the light extraction structure 411b has no unevenness, etc.), the planarization layer 413 may not be provided.

[0194] Note that the shape of the light-emitting device shown in FIG. 3(A) is octagonal, but the present invention is not limited to this. The light-emitting device may have other polygonal shapes or shapes having curved portions. In particular, as the shape of the light-emitting device, a triangle, a quadrilateral, a regular hexagon, etc. are preferable. This is because a plurality of light-emitting devices can be provided without gaps in a limited area. Also, because the light-emitting device can be formed by effectively using a limited substrate area. Also, the light-emitting elements included in the light-emitting device are not limited to one, and it may have a plurality of light-emitting elements.

[0195] Regarding the shape of the unevenness of the light extraction structure 411a and the light extraction structure 411b, the presence or absence of regularity does not matter. If the shape of the unevenness has periodicity, depending on the size of the unevenness, the unevenness may act like a diffraction grating, enhancing the interference effect and making it easier for light of a specific wavelength to be extracted into the atmosphere. Therefore, it is preferable that the shape of the unevenness has no periodicity. .

[0196] The bottom shape of the unevenness is not particularly limited, and can be, for example, a polygon such as a triangle or a quadrilateral, or a circle, etc. When the bottom shape of the unevenness has regularity, there will be gaps in adjacent portions. It is preferably provided so as not to occur. For example, as a preferable bottom surface shape, a regular hexagon can be mentioned.

[0197] The shape of the unevenness is not particularly limited, and for example, it can be a shape having a vertex such as a hemispherical shape, a cone, a pyramid (triangular pyramid, quadrangular pyramid, etc.), an umbrella shape, etc.

[0198] When the size and height of the unevenness are particularly 1 μm or more, the influence due to light interference can be suppressed, so it is preferable.

[0199] The light extraction structure 411a and the light extraction structure 411b can be directly formed on the support substrate 401. As the method, for example, an etching method, an abrasive grain processing method (sandblasting method), a microblast processing method, a frosting method, a droplet discharge method, a printing method (a method in which a pattern is formed such as screen printing or offset printing), a coating method such as a spin coating method, a dipping method, a dispenser method, an imprint method, a nanoimprint method, etc. can be appropriately used.

[0200] As the material of the light extraction structure 411a and the light extraction structure 411b, for example, a resin can be used. Also, as the light extraction structure 411a and the light extraction structure 411b, a hemispherical lens, a microlens array, a film provided with an uneven structure, a light diffusion film, etc. can also be used. For example, by adhering the above lens or film on the support substrate 401 using an adhesive or the like having the same refractive index as the support substrate 401 or the lens or film, the light extraction structure 411a and the light extraction structure 411b can be formed.

[0201] ​​​The planarization layer 413 is flatter on the surface that contacts the first electrode 421 than on the surface that contacts the light extraction structure 411b. Therefore, the first electrode 421 can be made into a flat film. As a result, the leakage current of the EL layer 423 due to the unevenness of the first electrode 421 can be suppressed. As the material of the planarization layer 413, glass, liquid, resin, etc. with a high refractive index can be used. The planarization layer 413 has light transmittance. This embodiment can be appropriately combined with other embodiments.

[0202]

[0203] (Embodiment 5) In this embodiment, a light-emitting device according to an aspect of the present invention will be described with reference to FIG. 4. FIG. 4(A) is a plan view showing a light-emitting device according to an aspect of the present invention, and FIG. 4(B) is a cross-sectional view taken along the dashed line C-D in FIG. 4(A).

[0204] The active matrix type light-emitting device according to this embodiment includes a light-emitting portion 551, a drive circuit portion 552 (gate side drive circuit portion), a drive circuit portion 553 (source side drive circuit portion), and a sealing material 507 on a support substrate 501. The light-emitting portion 551 and the drive circuit portions 552 and 553 are sealed in a space 515 formed by the support substrate 501, a sealing substrate 505, and the sealing material 507.

[0205] The light-emitting portion 551 shown in FIG. 4(B) is formed by a plurality of light-emitting units including a switching transistor 541a, a current control transistor 541b, and a second electrode 525 electrically connected to a wiring (source electrode or drain electrode) of the transistor 541b.

[0206]

[0206] The light-emitting element 503 has a top emission structure and includes a first electrode 521 that transmits visible light , an EL layer 523, and a second electrode 525 that reflects visible light. Also, a partition wall 519 is formed covering the end portion of the second electrode 525.

[0207] The light-emitting element 503 has an aspect of the present invention applied thereto. Specifically, the light-emitting layer included in the EL layer 523 contains an organic compound of an aspect of the present invention. Therefore, the light-emitting element 503 has a long lifespan. By applying an aspect of the present invention in this way, a highly reliable light-emitting device can be realized . .

[0208] On the support substrate 501, there is provided a lead-out wiring 517 for connecting external input terminals that transmit signals (such as video signals, clock signals, start signals, or reset signals) and potentials from the outside to the drive circuit units 552 and 553. Here, an example is shown in which an FPC 509 (Flexible Printed Circuit) is provided as the external input terminal. Note that , a printed wiring board (PWB) may be attached to the FPC 509. The light-emitting device in this specification includes not only the light-emitting device main body but also those in a state where an FPC or PWB is attached to the light-emitting device main body . . in the scope.

[0209] The drive circuit units 552 and 553 have a plurality of transistors. In FIG. 4(B), an example is shown in which the drive circuit unit 552 has a CMOS circuit combining an n-channel type transistor 542 and a p-channel type transistor 543. The circuit of the drive circuit unit can be formed by various CMOS circuits, PMOS circuits, or NMOS circuits. Also, in the present embodiment . shows a driver integrated type in which a driving circuit is formed on a substrate on which a light-emitting part is formed. However, the present invention is not limited to this configuration, and a driving circuit can also be formed on a substrate different from the substrate on which the light-emitting part is formed.

[0210] In order to prevent an increase in the number of processes, the lead wiring 517 is preferably manufactured using the same material and in the same process as the electrodes and wirings used for the light-emitting part and the driving circuit part.

[0211] In the present embodiment, an example is shown in which the lead wiring 517 is manufactured using the same material and in the same process as the source electrodes and drain electrodes of the transistors included in the light-emitting part 551 and the driving circuit part 552.

[0212] In FIG. 4(B), the sealing material 507 is in contact with the first insulating layer 511 on the lead wiring 517. The sealing material 507 may have low adhesion to metals. Therefore, the sealing material 507 is preferably in contact with an inorganic insulating film provided on the lead wiring 517. By adopting such a configuration, a light-emitting device with high sealing performance and adhesion and high reliability can be realized. Examples of the inorganic insulating film include oxide films of metals and semiconductors, nitride films of metals and semiconductors, and oxynitride films of metals and semiconductors. Specifically, silicon oxide films, silicon nitride films, oxynitride silicon films, silicon oxynitride films, aluminum oxide films, titanium oxide films, etc. can be mentioned.

[0213] In addition, the first insulating layer 511 has an effect of suppressing the diffusion of impurities into the semiconductor constituting the transistor. In addition, for the second insulating layer 513, it is preferable to select an insulating film having a planarization function in order to reduce surface irregularities caused by the transistor.

[0214] ​​​​​​ The structure of the transistor used in the light-emitting device according to one aspect of the present invention is not particularly limited. A top-gate type transistor may be used, or a bottom-gate type transistor such as an inverted staggered type may be used. Also, it may be a channel etch type or a channel protection type. Also, the material used for the transistor is not particularly limited.

[0215] The semiconductor layer can be formed using silicon or an oxide semiconductor. Examples of silicon include single-crystal silicon and polycrystalline silicon, and examples of the oxide semiconductor include In-Ga-Z n-based metal oxides and the like can be appropriately used. As the semiconductor layer, an oxide semiconductor which is an In-Ga-Zn-based metal oxide is used to form a transistor with low off-current, so that the leakage current when the light-emitting element is off can be suppressed, which is preferable.

[0216] On the sealing substrate 505, a color filter 533 which is a coloring layer is provided at a position overlapping with the light-emitting region of the light-emitting element 503. The color filter 533 is provided for the purpose of adjusting the emission color of the light-emitting element 503. For example, when a full-color display device is formed using a white light-emitting element, a plurality of light-emitting units provided with different color color filters are used. In that case, three colors of red (R), green (G), and blue (B) may be used, or four colors including yellow (Y) added thereto may be used. Also, a black matrix 531 is provided between adjacent color filters 533 (at a position overlapping with the partition wall 519). The black matrix 531 blocks the light from the light-emitting elements 503 of adjacent light-emitting units and suppresses color mixing between adjacent light-emitting units. Here

[0217] ​Then, the end of the color filter 533 is provided so as to overlap with the black matrix 531. This can suppress light leakage. The black matrix 531 can be made of a material that blocks light emitted from the light-emitting element 50 3, and can be formed using materials such as metals and resins. Note that the black matrix 531 may be provided in a region other than the light-emitting part 551 such as the drive circuit part 552.

[0218] Also, an overcoat layer 53 5 that covers the color filter 533 and the black matrix 531 is formed. The overcoat layer 535 is composed of a material that transmits light emitted from the light-emitting element 503, and for example, an inorganic insulating film or an organic insulating film can be used. Note that the overcoat layer 535 may not be provided if it is unnecessary.

[0219] In this embodiment, a light-emitting device using a color filter method has been described as an example, but the configuration of the present invention is not limited to this. For example, a painting method or a color conversion method may be applied.

[0220] This embodiment can be appropriately combined with other embodiments.

[0221] (Embodiment 6) In this embodiment, an example of an electronic device and a lighting device using a light-emitting device to which one aspect of the present invention is applied will be described with reference to FIGS. 5 and 6.

[0222] Since the light-emitting device used in the electronic device and the lighting device of this embodiment applies a light-emitting element including an organic compound of one aspect of the present invention, it has high reliability.

[0223] Examples of electronic devices to which the light-emitting device is applied include, for example, television devices (TVs or televisions ​​(also called a tuner receiver), monitors for computers, digital cameras, digital video cameras, digital photo frames, mobile phones (also called mobile telephones and mobile phone devices), portable game machines, portable information terminals, audio playback devices, large game machines such as pachinko machines, etc. are exemplified. Specific examples of these electronic devices and lighting devices are shown in FIGS. 5 and 6.

[0224] FIG. 5(A) shows an example of a television device. The television device 7100 has a display unit 7102 incorporated in a housing 7101. The display unit 7102 can display video. The light-emitting device to which one aspect of the present invention is applied can be used for the display unit 7102. Also, here, a configuration in which the housing 7101 is supported by a stand 7103 is shown.

[0225]

[0226]

[0227] The operation of the television device 7100 can be performed by operation switches provided in the housing 7101 or by a separate remote control operation device 7111. By operating keys provided on the remote control operation device 7111, channel and volume operations can be performed, and the video displayed on the display unit 7102 can be operated. Further, the remote control operation device 7111 may be configured to include a display unit for displaying information output from the remote control operation device 7111.

[0226] Note that the television device 7100 has a configuration including a receiver, a modem, etc. The receiver can receive general television broadcasts, and further, by connecting to a wired or wireless communication network via a modem, one-way (from sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication can also be performed.

[0227] ​​​FIG. 5(B) shows an example of a computer. The computer 7200 includes a main body 720 1, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a po rinting device 7206, etc. Note that the computer is manufactured by using the light-emitting device of one aspect of the present invention for its display unit 7203.

[0228] FIG. 5(C) shows an example of a portable game machine. The portable game machine 7300 is composed of two housings, a housing 7 301a and a housing 7301b, and is connected by a connecting portion 7302 so as to be open able and closable. A display unit 7303a is incorporated in the housing 7301a, and a display unit 73 03b is incorporated in the housing 7301b. Further, the portable game machine shown in FIG. 5(C) includes a speaker unit 7304, a recording medium insertion unit 7305, operation keys 7306, connection terminals 73 07, a sensor 7308 (having a function of measuring force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid , magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), an LED lamp, a microphone, etc. Of course, the configuration of the portable game machine is not limited to the above-mentioned one , and it is sufficient that at least one of the display unit 7303a and the display unit 7303b uses the light-emitting device of one aspect of the present invention, and other accessory equipment can be provided as appropriate . The portable game machine shown in FIG. 5(C) has a function of reading a program or data recorded on a recording medium and displaying it on a display unit, and a function of performing wireless communication with another portable game machine and sharing information . Note that the functions of the portable game machine shown in FIG. 5(C) are not limited to this , and it can have various functions.

[0229] FIG. 5(D) shows an example of a mobile phone. The mobile phone 7400 includes, in a housing 7401, in addition to a display unit 7402 incorporated therein, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. Note that the mobile phone 7400 is manufactured by using the light-emitting device according to one aspect of the present invention for the display unit 7402.

[0230] In the mobile phone 7400 shown in FIG. 5(D), information can be input by touching the display unit 7402 with a finger or the like. Also, operations such as making a call or creating an email can be performed by touching the display unit 7402 with a finger or the like.

[0231] The screen of the display unit 7402 mainly has three modes. The first is a display mode mainly for displaying images, the second is an input mode mainly for inputting information such as characters, and the third is a display + input mode in which the two modes of the display mode and the input mode are mixed.

[0232] For example, when making a call or creating an email, the display unit 7402 may be set to a character input mode mainly for inputting characters, and an input operation on the characters displayed on the screen may be performed.

[0233] Further, by providing a detection device having sensors such as a gyro and an acceleration sensor inside the mobile phone 7400 to detect the inclination, the orientation (portrait or landscape) of the mobile phone 7400 can be determined, and the screen display of the display unit 7402 can be automatically switched.

[0234] Also, the screen mode can be switched by touching the display unit 7402 or operating the housing 7401. This is performed by operating the button 7403. Also, it is possible to switch according to the type of image displayed on the display unit 7402. For example, if the image signal to be displayed on the display unit is video data, it is switched to the display mode, and if it is text data, it is switched to the input mode.

[0235] Also, in the input mode, the signal detected by the optical sensor of the display unit 7402 is detected, and the display is controlled to switch the screen mode from the input mode to the display mode when there is no input by the touch operation of the display unit 7402 for a certain period.

[0236] The display unit 7402 can also function as an image sensor. For example, by touching the display unit 74 02 with a palm or finger and imaging palm prints, fingerprints, etc., personal authentication can be performed. Also by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light on the display unit, it is also possible to image finger veins, palm veins, etc.

[0237] FIG. 5(E) shows an example of a foldable tablet terminal (opened state). The tablet terminal 7500 has a housing 7501a, a housing 7501b, a display unit 7502a, and a display unit 7502b. The housing 7501a and the housing 7501b are connected by a shaft portion 7503 and can perform an opening / closing operation about the shaft portion 7503 as an axis. Also, the housing 7501 a is provided with a power supply 7504, operation keys 7505, a speaker 7506, etc. Note that the tablet terminal 7500 is manufactured by using the light-emitting device according to one aspect of the present invention for both or one of the display units 7502a and 750 2b.

[0238] The display unit 7502a and the display unit 7502b have at least a part as a touch panel area.​​ It is possible to make [a certain operation], and data input can be performed by touching the displayed operation keys. For example, Keyboard buttons are displayed on the entire surface of the display unit 7502a to serve as a touch panel, and the display unit 75 02b can be used as a display screen.

[0239] FIG. 6(A) shows a desk lamp, which includes a lighting unit 7601, an umbrella 7602, a variable arm 7603, a support column 7604, a base 7605, and a power supply 7606. Note that the desk lamp is one embodiment of the present invention, which is manufactured by using a light-emitting device of this kind in the lighting unit 7601. Note that the lighting fixture also includes ceiling-fixed lighting fixtures or wall-mounted lighting fixtures, etc.

[0240] FIG. 6(B) shows an example in which a light-emitting device of one embodiment of the present invention is used in an indoor lighting fixture 7701 . Since the light-emitting device of one embodiment of the present invention can also be made larger in area, it can be used for large-area lighting devices for this purpose. In addition, it can also be used as a roll-type lighting fixture 7702. Note that, as shown in FIG. 6(B), in a room equipped with the indoor lighting fixture 7701, the desk lamp 7703 described in FIG. 6(A) may be used in combination.

Example

[0241] <Synthesis Example 1> In this example, a method for synthesizing 9,9-dimethyl-N-[4-(1-naphthyl)phenyl]-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine (abbreviation: PCBNBF) represented by the following structural formula (100) will be described

[0242]

Chemical Formula

[0243] In this example, two methods for synthesizing PCBNBF will be described.

[0244] ≪Synthesis Method 1≫ <Step 1-1: Synthesis of 1-(4-bromophenyl)naphthalene> The synthesis scheme of Step 1-1 is shown in (a-1).

[0245]

Chemical formula

[0246] Add 47 g (0.28 mol) of 1-naphthaleneboronic acid and 82 g (0.29 mol) of 4-bromoiodobenzene to a 3 L three-necked flask, and then add 750 mL of toluene and 250 mL of ethanol. The mixture was degassed by stirring under reduced pressure, and after degassing, the inside of the flask was purged with nitrogen. Add 415 mL of an aqueous potassium carbonate solution (2.0 mol / L) to this solution, and the mixture was degassed again by stirring under reduced pressure. After degassing, the inside of the flask was purged with nitrogen. Add 4.2 g (14 mmol) of tri(ortho-tolyl)phosphine and 0.7 g (2.8 mmol) of palladium(II) acetate here. The mixture was stirred at 90 °C for 1 hour under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature, and the aqueous layer of this mixture was extracted 3 times with toluene. The obtained extract and the organic layer were combined and washed twice with water and twice with saturated brine. Then, magnesium sulfate was added and left standing for 18 hours, followed by drying.

[0247] After filtration, the magnesium sulfate was removed, and the obtained filtrate was concentrated to obtain an orange liquid.

[0248] ​​​Add 500 mL of hexane to this orange liquid, and then purify the resulting solution through Celite (Wako Pure Chemical Industries, Ltd., catalog number: 531-16855, the same applies to the Celite described below, but repeated descriptions are omitted), Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135, the same applies to the Florisil described below, but repeated descriptions are omitted). The resulting filtrate was concentrated to obtain a colorless liquid. Hexane was added to this colorless liquid, and it was allowed to stand at -10 °C, and the precipitated impurities were filtered off. The resulting filtrate was concentrated to obtain a colorless liquid. This colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane), and a colorless liquid of the target product was obtained in a yield of 56 g and a yield of 72%. Co., Ltd., catalog number: 531-16855, the same applies to the Celite described below, but repeated descriptions are omitted) Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135, the same applies to the Florisil described below, but repeated descriptions are omitted) Co., Ltd., catalog number: 540-00135, the same applies to the Florisil described below, but repeated descriptions are omitted) The resulting filtrate was concentrated to obtain a colorless liquid. Hexane was added to this colorless liquid, and it was allowed to stand at -10 °C, and the precipitated impurities were filtered off. The resulting filtrate was concentrated to obtain a colorless liquid. This colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane), and a colorless liquid of the target product was obtained in a yield of 56 g and a yield of 72%. The resulting filtrate was concentrated to obtain a colorless liquid. This colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane), and a colorless liquid of the target product was obtained in a yield of 56 g and a yield of 72%. The resulting filtrate was concentrated to obtain a colorless liquid. This colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane), and a colorless liquid of the target product was obtained in a yield of 56 g and a yield of 72%. The resulting filtrate was concentrated to obtain a colorless liquid. This colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane), and a colorless liquid of the target product was obtained in a yield of 56 g and a yield of 72%.

[0249] <Step 1-2: Synthesis of 9,9-dimethyl-N-(4-naphthyl)phenyl-N-phenyl- 9H-fluoren-2-amine The synthesis scheme of Step 1-2 is shown in (a-2).

[0250]

Chemical formula

[0251] Place 40 g (0.14 mol) of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 40 g (0.42 mol ) of sodium tert-butoxide, and 2.8 g (1.4 mmol) of bis(dibenzylideneacetone)palladium(0) in a 1 L three-necked flask, and add 560 mL of a toluene solution of 44 g (0.15 mol) of 1-(4-bromophenyl)naphthalene. ) of sodium tert-butoxide, and 2.8 g (1.4 mmol) of bis(dibenzylideneacetone)palladium(0) in a 1 L three-necked flask, and add 560 mL of a toluene solution of 44 g (0.15 mol) of 1-(4-bromophenyl)naphthalene. The mixture was degassed by stirring under reduced pressure, and after degassing, the flask The mixture was degassed by stirring under reduced pressure, and after degassing, the flask The inside of the flask was replaced with nitrogen. Then, 14 mL (7.0 mmol) of tri(tert-butyl)phosphine (10 wt% hexane solution) was added, and the mixture was stirred at 110 °C for 2 hours under a nitrogen stream. After that, the mixture was cooled to room temperature, and the solid was filtered off by suction filtration. The resulting filtrate was concentrated to obtain a dark brown liquid. This dark brown liquid was mixed with toluene, and the resulting solution

[0252] was purified through celite, alumina, and florisil. The resulting filtrate was concentrated to obtain a pale yellow liquid. This pale yellow liquid was recrystallized from acetonitrile to obtain 53 g of the target pale yellow powder in a yield of 78%. <Synthesis of N-(4-bromophenyl)-9,9-dimethyl-N-[4-(1- naphthyl)phenyl]-9H-fluorene-2-amine>

[0253]

[0254]

[0255] To a 2 L Meyer flask, 59 g (0.12 mol) of 9,9-dimethyl-N-(4-naphthyl)phenyl-N-phenyl-9H-fluorene-2-amine and 300 mL of toluene were added, and the mixture was stirred while heating. After the resulting solution was allowed to cool to room temperature, 300 mL of ethyl acetate was added, and then 21 g (0 .12 mol) of N-bromosuccinimide (abbreviation; NBS) was added, and the mixture was stirred at room temperature for about 2.5 hours. 400 mL of a saturated aqueous sodium hydrogen carbonate solution was added to this mixture and stirred at room temperature. The organic layer of this mixture was washed with saturated aqueous carbonic acid hydrogen and then with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 10 / 1 to 5 / 1) to obtain 62 g of the target compound as a pale yellow solid in a yield of 85%. It was washed twice with an aqueous solution of sodium and twice with saturated brine. Then, magnesium sulfate was added and the mixture was allowed to stand for 2 hours and dried. After removing magnesium sulfate by natural filtration of this mixture , the obtained filtrate was concentrated to obtain a yellow liquid. This liquid was dissolved in toluene, and then this solution was purified by passing through celite, alumina, and florisil to obtain a pale yellow solid. When the obtained pale yellow solid was reprecipitated using toluene / acetonitrile, the white powder of the target product was obtained in a yield of 56 g and a yield of 85%.

[0256] <Step 1-4: Synthesis of PCBNBF> The synthesis scheme of Step 1-4 is shown in (a-4).

[0257]

Chemical formula

[0258] Into a 1 L three-necked flask, 51 g (90 mmol) of N-(4-bromophenyl)-9,9-dimethyl-N-[4-(1 -naphthyl)phenyl]-9H-fluorene-2-amine, 28 g (95 mmol) of 9 -phenyl-9H-carbazole-3-boronic acid, 0.4 mg (1.8 mmol) of palladium(II) acetate, 1. 4 g (4.5 mmol) of tri(ortho-tolyl)phosphine, 300 mL of toluene, 100 mL of ethanol, and 135 mL of an aqueous potassium carbonate solution (2.0 mol / L) were added. This mixture was degassed by stirring under reduced pressure, and after degassing, the inside of the flask was replaced with nitrogen. This mixture was stirred at 90 °C for 1.5 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature and then the solid was recovered by suction filtration . The organic layer was taken out from the obtained mixture of the aqueous layer and the organic layer, and concentrated to obtain a brown solid . . This brown solid was recrystallized using toluene / ethyl acetate / ethanol to obtain the target white powder. Also, the solid recovered after stirring, together with the white powder obtained by recrystallization, was dissolved in toluene and then purified through celite, alumina, and florisil. The resulting solution was concentrated and recrystallized using toluene / ethanol, and the target white powder was obtained in a yield of 54 g and a recovery rate of 82%.

[0259] 51 g of the obtained white powder was purified by sublimation using the train sublimation method. The sublimation purification was carried out by heating the white powder at 360 °C under the conditions of a pressure of 3.7 Pa and an argon flow rate of 15 mL / min. After sublimation purification, the target pale yellow solid was obtained in a yield of 19 g and a recovery rate of 38%.

[0260] By nuclear magnetic resonance method (NMR), it was confirmed that this compound is the target 9,9-dimethyl-N- 4-(1-naphthyl)phenyl]-N-[4-(9-phenyl-9H-carbazol-3 -yl)phenyl]-9H-fluorene-2-amine (abbreviation: PCBNBF).

[0261] The 1H NMR data of the obtained substance are shown below. 1 1 1H NMR (CDCl3, 500 MHz): δ = 1.50 (s, 6H), 7.21 ( dd, J = 8.0 Hz, 1.6 Hz, 1H), 7.26 - 7.38 (m, 8H), 7.4 1 - 7.44 (m, 5H), 7.46 - 7.55 (m, 6H), 7.59 - 7.69 (m , 9H), 7.85 (d, J = 8.0 Hz, 1H), 7.91 (dd, J = 7.5 Hz, 1.7 Hz, 1H), 8.07 - 8.09 (m, 1H), 8.19 (d, J = 8.0 Hz , 1H), 8.37 (d, J = 1.7 Hz, 1H).

[0262] Also, 1 The 1H NMR chart is shown in Fig. 7. Note that Fig. 7(B) is a chart showing an enlarged range of 7.00 ppm to 10.0 ppm in Fig. 7(A). .00 ppm to 10.0 ppm.

[0263] ≪Synthesis Method 2≫ <Step 2-1: Synthesis of 1-(4-aminophenyl)naphthalene> The synthesis scheme of Step 2-1 is shown in (b-1).

[0264]

Chemical formula

[0265] Into a 2 L three-necked flask, 25 g (0.15 mol) of 4-bromoaniline, 25 g (0.15 mol) of 1-naphthalene boronic acid, 450 mL of toluene, and 150 mL of ethanol were added. This mixture was degassed by stirring under reduced pressure, and after degassing, the inside of the system was replaced with nitrogen. 220 mL of an aqueous potassium carbonate solution (2.0 mol / L) was added to this mixture, and this mixture was degassed again by stirring under reduced pressure. After degassing, the inside of the system was replaced with nitrogen. To this mixture, 0.48 g (2.1 mmol) of palladium(II) acetate and 2.4 g (7.9 mmol) of tri(ortho-tolyl)phosphine were added, and this mixture was stirred at 80 °C for 3 hours under a nitrogen stream. After stirring, the mixture was allowed to cool to room temperature, and the aqueous layer was extracted 3 times with toluene. The obtained extract and the organic layer were combined and washed 2 times with water and 2 times with saturated brine. Thereafter, magnesium sulfate was added and allowed to stand for 18 hours and dried. This mixture was filtered naturally to remove magnesium sulfate, and the obtained filtrate was concentrated to obtain an orange liquid. This orange liquid was dissolved in toluene. After stirring, the mixture was allowed to cool to room temperature, and the aqueous layer was extracted 3 times with toluene. The combined extract and organic layer were washed twice with water and twice with saturated brine. Then, the combined extract and organic layer were washed twice with water and twice with saturated brine. After that, magnesium sulfate was added and the mixture was allowed to stand for 18 hours and dried. This mixture was filtered naturally to remove magnesium sulfate, and the obtained filtrate was concentrated to obtain an orange liquid. This orange liquid was dissolved in toluene, and the resulting solution was filtered naturally to remove magnesium sulfate. This solution was purified through Celite, alumina, and Florisil. The filtrate was concentrated to obtain the target orange liquid in a yield of 33 g and a yield rate of 99%.

[0266] <Step 2-2: Synthesis of 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole -3-yl)diphenylamine> The synthesis scheme of Step 2-2 is shown in (b-2).

[0267]

Chemical formula

[0268] To a 2 L three-necked flask, 50 g (0.13 mol) of 3-(4-bromophenyl)-9-phenyl-9H-carbazole , 36 g (0.38 mol ) of sodium tert-butoxide, 30 g (0.14 mol) of 4-(1-naphthyl)aniline, and 500 mL of toluene were added. The mixture was degassed by reducing the pressure inside the system while stirring, and after degassing, the inside of the system was replaced with nitrogen . After degassing, 0 .79 g (1.4 mmol) of bis(dibenzylideneacetone)palladium(0) and 13 mL of tri(tert-butyl)phosphine (10 wt% hexane solution) were added, and the mixture was stirred at 80 °C for about 2 hours and then at 110 °C for 3 hours. After stirring , 0.39 g (0.68 mmol) of bis(dibenzylideneacetone)palladium(0) and 4.5 mL of tri(tert-butyl)phosphine (10 wt% hexane solution) were added , and the mixture was further stirred at 110 °C for 3 hours. After heating, the mixture was cooled to room temperature while stirring and then , the solid was filtered off by suction filtration, and the obtained filtrate was concentrated. The obtained solution was dissolved in toluene , and this solution was purified through Celite, alumina, and Florisil. The obtained solution The liquid obtained by concentration was recrystallized with hexane to obtain a black solid.

[0269] This black solid was dissolved in toluene, and this solution was washed three times with water and twice with saturated brine. Magnesium sulfate was added to the organic layer for drying, and this mixture was filtered naturally to remove magnesium sulfate. The obtained filtrate was purified through celite, alumina, and florisil. The obtained solution was concentrated to obtain a yellow liquid. When this yellow liquid was recrystallized with hexane, a yellow powder was obtained. This yellow powder was suspended in toluene, and this mixture was irradiated with ultrasonic waves to wash the powder, and the target pale yellow powder was obtained in a yield of 18 g and a recovery rate of 27%. Also, the filtrates of the above recrystallization and the filtrate obtained by filtration after ultrasonic irradiation were combined and purified by silica gel column chromatography (the developing solvent was gradually changed from hexane:toluene = 4:1 to 2:3). As a result, a yellow solid was obtained. This yellow solid was recrystallized with toluene, and the target pale yellow powder was obtained in a yield of 12 g and a recovery rate of 18%. Combined with the previously recovered portion, 3 0 g of the target powder was obtained in a yield of 45%. Also, by concentrating the filtrate after recrystallization, 26 g of a yellow solid containing the target substance was obtained.

[0270] 22 g of the yellow solid obtained by concentrating the filtrate after the above recrystallization was sublimation-purified by the train sublimation method. The sublimation purification was carried out by heating the yellow solid at 305 °C under the conditions of a pressure of 2.9 Pa and an argon flow rate of 10 mL / min. After sublimation purification, 7.1 g of a pale yellow solid was obtained in a recovery rate of 3 8%.

[0271] 7.1 g of the pale yellow solid obtained by the above sublimation purification was sublimation-purified again by the train sublimation method. The sublimation purification was carried out under the conditions of a pressure of 2.2 Pa and an argon flow rate of 10 mL / min. The yellow solid was heated at 305 °C. After sublimation purification, 5.7 g of the target light yellow solid was obtained. It was obtained with a recovery rate of 80%.

[0272] <Step 2-3: Synthesis of PCBNBF> The synthesis scheme of Step 2-3 is shown in (b-3).

[0273]

Chemical formula

[0274] Into a 100 mL three-necked flask, 4.7 g (8.8 mmol) of 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)diphenylamine, 2.6 g (27 mmol) of sodium tert-butoxide, 0.17 g (0.17 mmol) of bis(dibenzylideneacetone)palladium(0), and a solution of 2.3 g (8.1 mmol) of 2-bromo-9,9'-dimethyl-9H-fluorene dissolved in 40 mL of toluene were added. This mixture was degassed by reducing the pressure inside the system while stirring, and then purged with nitrogen. After degassing, 0.8 mL of tri(tert-butyl)phosphine (10 wt% hexane solution) was added to this mixture, and the mixture was refluxed at 110 °C for 2 hours. After refluxing, it was allowed to cool to room temperature, and this mixture was filtered through celite to remove the solid. The obtained filtrate was purified through celite, alumina, and florisil to obtain the target light yellow solid. When this light yellow solid was recrystallized from toluene / ethanol, 1.4 g of the target white powder was obtained. Also, the mother liquor after recrystallization was concentrated, and the obtained white solid was recrystallized from ethyl acetate / acetonitrile to obtain 2.2 g of the target white powder. Combining with the previously recovered portion, a solution of 2.3 g (8.1 mmol) of 2-bromo-9,9'-dimethyl-9H-fluorene dissolved in 40 mL of toluene were added. This mixture was degassed by reducing the pressure inside the system while stirring, and then purged with nitrogen. After degassing, 0.8 mL of tri(tert-butyl)phosphine (10 wt% hexane solution) was added to this mixture, and the mixture was refluxed at 110 °C for 2 hours. After refluxing, it was allowed to cool to room temperature, and this mixture was filtered through celite to remove the solid. The obtained filtrate was purified through celite, alumina, and florisil to obtain the target light yellow solid. When this light yellow solid was recrystallized from toluene / ethanol, 1.4 g of the target white powder was obtained. Also, the mother liquor after recrystallization was concentrated, and the obtained white solid was recrystallized from ethyl acetate / acetonitrile to obtain 2.2 g of the target white powder. Combining with the previously recovered portion, When this light yellow solid was recrystallized from toluene / ethanol, 1.4 g of the target white powder was obtained. Also, the mother liquor after recrystallization was concentrated, and the obtained white solid was recrystallized from ethyl acetate / acetonitrile to obtain 2.2 g of the target white powder. Combining with the previously recovered portion, a solution of 2.3 g (8.1 mmol) of 2-bromo-9,9'-dimethyl-9H-fluorene dissolved in 40 mL of toluene were added.

[0275] When this light yellow solid was recrystallized from toluene / ethanol, 1.4 g of the target white powder was obtained. Also, the mother liquor after recrystallization was concentrated, and the obtained white solid was recrystallized from ethyl acetate / acetonitrile to obtain 2.2 g of the target white powder. Combining with the previously recovered portion, 1.4 g of the target white powder was obtained. Also, the mother liquor after recrystallization was concentrated, and the obtained white solid was recrystallized from ethyl acetate / acetonitrile to obtain 2.2 g of the target white powder. Combining with the previously recovered portion, 1.4 g of the target white powder was obtained. Also, the mother liquor after recrystallization was concentrated, and the obtained white solid was recrystallized from ethyl acetate / acetonitrile to obtain 2.2 g of the target white powder. Combining with the previously recovered portion, Thus, 3.6 g of the white powder of the target substance was obtained with a yield of 59%.

[0276] The 3.6 g of the obtained white powder was purified by sublimation using the train sublimation method. The sublimation purification was carried out by heating the white powder at 370 °C under the conditions of a pressure of 3.7 Pa and an argon flow rate of 15 mL / min. After the sublimation purification, 2.0 g of a pale yellow solid of the target substance was obtained with a recovery rate of 56%.

[0277] It was confirmed by nuclear magnetic resonance method (NMR) that this compound was PCBNBF, the target substance. In addition, the 1 1H NMR data of the obtained substance was the same as that of the substance obtained by Synthesis Method 1.

[0278] In Synthesis Method 2 shown in this example, the yield of 4-(1 -naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)diphenylamine (hereinafter referred to as target substance A), which is the target substance in the synthesis of Step 2-2, was low. This is because, as a by-product, 4-(1-naphthyl)-4',4''-bis(9-phenyl 9H-carbazol-3-yl)triphenylamine (hereinafter referred to as by-product B), which is the compound shown in the following structural formula ( 900), was generated.

[0279]

Chemical formula

[0280] By-product B showed very similar solubility and polarity to target substance A, so it was difficult to remove by purification methods such as recrystallization and column chromatography.

[0281] Here, by-product B has an extra substituent containing a carbazolyl group added compared to target substance A Therefore, its thermal properties are higher than those of target A. Thus, when purifying target A, train sub By performing sublimation purification by the remelting method, by-product B could be easily removed. .

[0282] In addition, when the synthesis of Step 2-3 was carried out using target A contaminated with a trace amount of by-product B, in this case, by-product B exhibits solubility and polarity very similar to those of PCBNBF, which is the target in Step 2-3. Therefore, it is difficult to remove by using purification methods such as recrystallization and column chromatography. In addition, since PCBNBF and by-product B have similar molecular weights, it was also difficult to remove them by sublimation purification. Therefore, when synthesizing PCBNBF by Synthesis Method 2, it is necessary to purify target A to a high purity.

[0283] From the above, in the synthesis of target PCBNBF, from the perspective of purifying target A, by applying Synthesis Method 1, target A can be obtained without generating by-product B. Therefore, as a synthesis method of PCBNBF, Synthesis Method 1 is more preferable.

[0284] In addition, the absorption spectrum of the toluene solution of PCBNBF is shown in Fig. 8(A), and the emission spectrum is shown in Fig. 8(B), respectively. Also, the absorption spectrum of the thin film of PCBNBF is shown in Fig. 9(A), and the emission spectrum is shown in Fig. 9(B), respectively. For the measurement of the absorption spectrum, a UV-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used. The solution was placed in a quartz cell, and the thin film was deposited on a quartz substrate to prepare a sample for measurement. Regarding the absorption spectrum, for the solution, the absorption spectrum measured by putting only toluene in the quartz cell was subtracted. Shows toluene, and for the thin film, shows the absorption spectrum obtained by subtracting the absorption spectrum of the quartz substrate was used. In FIGS. 8 and 9, the horizontal axis represents the wavelength (nm) and the vertical axis represents the intensity (arbitrary unit). For the toluene solution, an absorption peak was observed around 352 nm, and the peak of the emission wavelength was 417 nm (excitation wavelength 352 nm). For the thin film, absorption peaks were observed around 212 nm, 283 nm, and 358 nm, and the peak of the emission wavelength was 434 nm (excitation wavelength 371 nm).

[0285] In addition, PCBNBF was analyzed by liquid chromatography mass spectrometry (Liquid Chromatog raphy Mass Spectrometry (abbreviation: LC / MS analysis)) for mass (MS) analysis.

[0286] The LC / MS analysis was performed using Waters Acquity UPLC and Waters X evo G2 Tof MS. In the MS analysis, ionization was performed by electrospray ionization (ElectroSpray Ionization (abbreviation: ESI)). At this time, the capillary voltage was 3.0 kV and the sample cone voltage was 30 V, and the detection was performed in the positive mode. The components ionized under the above conditions were collided with argon gas in the collision cell (collision cell) to dissociate into product ions. The energy (collision energy) when colliding with argon was 50 eV and 70 eV. In addition, the mass range to be measured was set to m / z = 100 - 1200. FIG. 22(A) shows the measurement results when the collision energy is 50 eV, and FIG. 22(B) shows the measurement results when the collision energy is 70 eV.

[0287] ​​​From the results in Fig. 22(A), when the collision energy is 50 eV, PCBNBF is mainly detected with multiple product ions around m / z = 728, m / z = 713, m / z = 698, m / z = 509, m / z = 394, and m / z = 294 respectively due to the presence or absence of hydrogen ions and the existence of isotopes.

[0288] Also, from the results in Fig. 22(B), when the collision energy is 70 eV, PCBNBF is mainly detected with multiple product ions around m / z = 711, m / z = 697, m / z = 571, m / z = 509, m / z = 393, and m / z = 256 respectively due to the presence or absence of hydrogen ions and the existence of isotopes. It should be noted that the results shown in Fig. 22(A)(B) are important data for identifying PCBNBF contained in the mixture as they show characteristic results derived from PCBNBF.

Example

[0289] <Synthesis Example 2> In this example, the synthesis method of N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF) shown in the following structural formula (101) will be described.

[0290]

Chemical formula

[0291] The synthesis scheme of PCBNBSF is shown in (c-1).

[0292]

Chemical formula

[0293] Into a 1 L three-necked flask, 33 g (62 mmol) of 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)diphenylamine, 23 g (59 mmol) of 2-bromo-9,9'-spirobifluorene, 17 g (180 mmol) of sodium tert-butoxide, and 235 mL of toluene were added. The mixture was degassed by reducing the pressure while stirring, and after degassing, it was purged with nitrogen. To this mixture, 1.5 mL (3.0 mmol) of tris(tert-butyl)phosphine (10 wt% hexane solution) and 0.34 g (0.59 mmol) of bis(dibenzylideneacetone)palladium(0) were added. This mixture was stirred at 80 °C for 2 hours under a nitrogen stream. After stirring, the mixture was cooled to room temperature, and the solid precipitated by suction filtration was filtered off. The obtained filtrate was dissolved in toluene, and this solution was purified through celite and florisil, and the obtained solution was concentrated to obtain a yellow solid. This yellow solid was recrystallized from ethyl acetate / hexane to obtain 47 g of the target pale yellow powder in a yield of 94%. The synthesis method of 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)diphenylamine can be referred to Example 1.

[0294] 7.4 g of the obtained pale yellow powder was purified by sublimation using the train sublimation method. The sublimation purification was carried out by heating the pale yellow powder at 380 °C under the conditions of a pressure of 3.6 Pa and an argon flow rate of 15 mL / min. After sublimation purification, 6.1 g of the pale yellow solid was obtained in a recovery rate of 82%.

[0295] 6.1 g of the pale yellow solid obtained by the above sublimation purification was again sublimation-purified by the train sublimation method. The sublimation purification was carried out under the conditions of a pressure of 3.6 Pa and an argon flow rate of 15 mL / min. The pale yellow solid was heated at 380 °C. After the sublimation purification, the pale yellow solid of the target product was obtained with a yield of 5. 1 g and a recovery rate of 83%.

[0296] By nuclear magnetic resonance method (NMR), it was confirmed that this compound was the target product, N-[4-(9-phenyl -9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl -9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF).

[0297] The 1 1H NMR data of the obtained substance are shown below. 1 1H NMR (CDCl3, 500 MHz): δ = 6.69 - 6.71 (m, 2H), 6.85 (d, J = 7.5 Hz, 2H), 7.06 (t, J = 7.5 Hz, 1H), 7. 09 - 7.17 (m, 6H), 7.20 (dd, J = 8.0 Hz, 2.3 Hz, 1H), 7.27 - 7.54 (m, 16H), 7.58 - 7.63 (m, 5H), 7.74 - 7. 83 (m, 5H), 7.88 - 7.93 (m, 2H), 8.17 (d, J = 7.5 Hz, 1H), 8.28 (d, J = 1.7 Hz, 1H).

[0298] Also, 1 the 1H NMR chart is shown in Fig. 10. Note that Fig. 10(B) is an enlarged chart of the range of 6.00 ppm to 10.0 ppm in Fig. 10(A).

[0299] Also, the absorption spectrum of the toluene solution of PCBNBSF is shown in Fig. 11(A), and the emission spectrum The rings are shown in Fig. 11(B) respectively. The absorption spectrum of the thin film of PCBNBSF is shown in Fig. 1 2(A), and the emission spectrum is shown in Fig. 12(B) respectively. The method for measuring the absorption spectrum is the same as in Example 1. In Figs. 11 and 12, the horizontal axis represents the wavelength (nm), and the vertical axis represents the intensity ( arbitrary unit). In the case of the toluene solution, an absorption peak was observed near 351 nm, and the emission peak wavelength was 411 nm (excitation wavelength 331 nm). In the case of the thin film, an absorption peak was observed near 3 66 nm, and the emission peak wavelength was 435 nm (excitation wavelength 375 n m).

[0300] In addition, PCBNBSF was analyzed by liquid chromatography-mass spectrometry (Liquid Chromato graphy Mass Spectrometry (abbreviation: LC / MS analysis)) for mass (MS) analysis. The measurement method, measurement conditions, etc. of the LC / MS analysis were the same as in Example 1. Note that the energy (collision energy) when argon was collided was set to 70 eV. The mass

[0301] range to be measured was set to m / z = 100~1200. The measurement results are shown in Fig. 23. From the results of Fig. 23, PCBNBSF was mainly due to the presence or absence of hydrogen ions and the presence of isotopes, and mainly a plurality of product ions were detected near m / z = 851, near m / z = 648, near m / z = 536, near m / z = 333

[0302] near m / z = 315 respectively. Note that the results shown in Fig. 23 show the characteristic results derived from PCBNBSF and can be said to be important data for identifying PCBNBSF contained in the mixture.

Example

[0303] In this embodiment, a light-emitting element according to one aspect of the present invention will be described with reference to FIG. 13. In this embodiment, the chemical formulas of the materials used are shown below.

[0304] [Chemical formula]

[0305] The manufacturing methods of the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3 of this embodiment are shown below. .

[0306] (Light-emitting element 1) First, indium tin oxide (ITSO) containing silicon oxide was formed into a film on a glass substrate 1100 by sputtering to form a first electrode 1101. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm. Here, the first electrode 1101 is an electrode that functions as the anode of the light-emitting element.

[0307] Next, as a pretreatment for forming a light-emitting element on the glass substrate 1100, the substrate surface was washed with water and baked at 200 °C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

[0308] After that, the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 -4 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus, and then the glass substrate 110 0 was allowed to cool for about 30 minutes.

[0309] Next, with the surface on which the first electrode 1101 is formed facing downward, the glass substrate 1100 on which the first electrode 1101 is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus, and 10 -4 ​After reducing the pressure to the Pa level, by means of a vapor deposition method using resistance heating, on the first electrode 1101 , 4,4’,4’’-(1,3,5-benzenetriyl)tris(dibenzothiophene) ( abbreviation: DBT3P-II) and molybdenum(VI) oxide were co-evaporated to form the hole injection layer 1 111. The film thickness was set to 40 nm, and the ratio of DBT3P-II to molybdenum(VI) oxide was adjusted to a weight ratio of 4:2 (= DBT3P-II: molybdenum(VI) oxide). Note that the co-evaporation method is a vapor deposition method in which vapor deposition is performed simultaneously from a plurality of evaporation sources in one processing chamber .

[0310] Next, 4-phenyl-4’-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP) was formed into a film with a film thickness of 20 nm on the hole injection layer 1111 to form the hole transport layer 1112.

[0311] Furthermore, 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4 ,6mDBTP2Pm-II), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9’-spirobi[9 H-fluorene]-2-amine (abbreviation: PCBNBSF), and (acetylacetonato) bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation :[Ir(tBuppm)2(acac)]) were co-evaporated to form the light-emitting layer 1113 on the hole transport layer 1112. Here, the weight ratio of 4,6mDBTP2Pm-II, PCBNBSF, and [Ir(tBuppm)2(acac)] was 0.7:0.3:0.05 (= 4,6mDBTP2Pm-II:PCBNBSF:[Ir(tBuppm)2(acac )]) adjusted to form a layer with a thickness of 15 nm, and the weight ratio is 0.8:0.2 :0.05(=4,6mDBTP2Pm-II:PCBNBSF:[Ir(tBuppm )2(acac)]) adjusted to form a layer with a thickness of 25 nm and laminated them.

[0312] Next, 4,6mDBTP2Pm-II was formed on the light-emitting layer 1113 to have a film thickness of 10 nm and further, bathophenanthroline (abbreviation: BPhen) was formed to have a film thickness of 20 nm to form the electron transport layer 1114.

[0313] Furthermore, lithium fluoride (LiF) was vapor-deposited on the electron transport layer 1114 with a film thickness of 1 nm to form the electron injection layer 1115.

[0314] Finally, as the second electrode 1103 functioning as a cathode, aluminum was vapor-deposited to have a film thickness of 200 nm to fabricate the light-emitting device 1 of this example.

[0315] Note that in the above-described vapor deposition process, all vapor depositions used the resistance heating method.

[0316] (Comparative Light-Emitting Device 2) The light-emitting layer 1113 of the comparative light-emitting device 2 is 4,6mDBTP2Pm-II, 4-phenyl-4 ’-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BA1BP), and [Ir(tBuppm)2(acac)] were co-vapor-deposited to form it. Here, the weight ratio of 4,6mDBTP2Pm-II, PCBA1BP, and [Ir(tBup pm)2(acac)] is 0.7:0.3:0.05(=4,6mDBTP2 Pm-II:PCBA1BP:[Ir(tBuppm)2(acac)]) A layer with a thickness of 15 nm formed by adjustment and a layer with a thickness of 25 nm formed by adjusting the weight ratio to 0.8:0.2:0.05 (= 4, 6mDBTP2Pm-II:PCBA1BP:[Ir(tBuppm)2(acac)] ) were laminated. Except for the light-emitting layer 1113, it was fabricated in the same manner as the light-emitting element 1.

[0317] (Comparative light-emitting element 3) The light-emitting layer 1113 of the comparative light-emitting element 3 was formed by co-evaporating 4,6mDBTP2Pm-II, N-phenyl-N -[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-spiro-9,9 '-bifluorene-2-amine (abbreviation: PCBASF), and [Ir(tBuppm)2 (acac)]. Here, a layer with a thickness of 15 nm formed by adjusting the weight ratio of 4,6mDBTP2Pm-II , PCBASF, and [Ir(tBuppm)2(acac)] to 0.7:0 .3:0.05 (= 4,6mDBTP2Pm-II:PCBASF:[Ir(tBupp m)2(acac)]) and a layer with a thickness of 25 nm formed by adjusting the weight ratio to , 0.8:0.2:0.05 (= 4,6mDBTP2Pm-II:PCBASF:[Ir (tBuppm)2(acac)]) were laminated. Except for the light-emitting layer 1113, it was fabricated in the same manner as the light-emitting element 1.

[0318] The device structure of the light-emitting device of this example obtained as above is shown in Table 1.

[0319] [Table 1]

[0320] The light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3 were placed in a glove box under a nitrogen atmosphere ​​In this case, an operation was performed to seal each light-emitting element with a glass substrate so that it was not exposed to the atmosphere. After that, the operating characteristics of these light-emitting elements were measured. The measurement was performed at room temperature (atmosphere maintained at 25 °C).

[0321] The luminance-current efficiency characteristics of the light-emitting element of this example are shown in FIG. 14. In FIG. 14, the horizontal axis represents luminance (cd / m 2 ), and the vertical axis represents current efficiency (cd / A). The voltage-luminance characteristics are shown in FIG. 15. In FIG. 15, the horizontal axis represents voltage (V), and the vertical axis represents luminance (cd / m 2 ). The luminance-external quantum efficiency characteristics are shown in FIG. 16. In FIG. 16, the horizontal axis represents luminance (cd / m 2 ), and the vertical axis represents external quantum efficiency (%). Also, the voltage (V), current density (mA / cm ), CIE chromaticity coordinates (x, y), current efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%) near a luminance of 1000 cd / m 2 for each light-emitting element are shown in Table 2. 2

[0322]

Table 2

[0323] As shown in Table 2, the CIE chromaticity coordinates of Light-Emitting Element 1 at a luminance of 1100 cd / m 2 were (x, y) = (0.43, 0.56). The CIE chromaticity coordinates of Comparative Light-Emitting Element 2 2 at a luminance of 1000 cd / m were (x, y) = (0.43, 0.56). The CIE chromaticity coordinates of Comparative Light-Emitting Element 3 at a luminance of 1000 cd / m were (x, y) = (0.43, 0.56). The light-emitting element shown in this example is derived from [Ir(tBuppm)2(acac)]. 2 were (x, y) = (0.43, 0.56). ​ It was found that yellow-green light emission was obtained.

[0324] From FIGS. 14 to 16 and Table 2, it was found that the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3 all had a low driving voltage, high current efficiency, and high external quantum efficiency.

[0325] Next, reliability tests were conducted on the light-emitting element 1, the comparative light-emitting element 2, and the comparative light-emitting element 3. The reliability test results are shown in FIG. 17. In FIG. 17, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. The reliability test was conducted at room temperature, and the initial luminance was set to 5000 cd / m 2 2 and the light-emitting element of this example was driven under the condition of a constant current density. From FIG. 17, the luminance of the light-emitting element 1 after 180 hours maintained 85% of the initial luminance, the luminance of the comparative light-emitting element 2 after 160 hours maintained 53% of the initial luminance, and the luminance of the comparative light-emitting element 3 after 160 hours maintained 56% of the initial luminance. From the results of this reliability test, it was revealed that the light-emitting element 1 has a longer lifespan than the comparative light-emitting element 2 and the comparative light-emitting element 3.

[0326] As described above, by using the PCBNBSF fabricated in Example 2 as the light-emitting layer, a light-emitting element with a long lifespan could be fabricated.

Example

[0327] In this example, a light-emitting element according to one aspect of the present invention will be described with reference to FIG. 13. The chemical formulas of the materials used in this example are shown below. Note that the materials shown in Example 3 are omitted. The chemical formulas of the materials used are shown below. For the materials shown in Example 3, they are omitted.

[0328]

Chemical formula

[0329] The manufacturing methods of the light-emitting element 4 and the comparative light-emitting element 5 of the present example are shown below.

[0330] (Light-emitting element 4) First, in the same manner as the light-emitting element 1, a first electrode 1101, a hole injection layer 1 111, and a hole transport layer 1112 were formed on the glass substrate 1100.

[0331] Next, 2-[3’-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzothieno [f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 9,9-dimethyl-N -[4-(1-naphthyl)phenyl]-N-[4-(9-phenyl-9H-carbazole -3-yl)phenyl]-9H-fluorene-2-amine (abbreviation: PCBNBF), and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]) were co-evaporated to form a light-emitting layer 11 113 on the hole transport layer 1112. Here, the weight ratio of 2mDBTBPDBq-II, PCBNBF, and Ir(dppm)2(acac)] was adjusted to 0.8:0.2:0.05 (= 2mDB TBPDBq-II:PCBNBF:[Ir(dppm)2(acac)]). Also, the film thickness of the light-emitting layer 1113 was set to 40 nm.

[0332] Next, 2mDBTBPDBq-II was formed into a film with a film thickness of 15 nm on the light-emitting layer 1113, and further, BPhen was formed into a film with a film thickness of 15 nm, thereby forming an electron transport layer 11 114.

[0333] Furthermore, LiF was deposited on the electron transport layer 1114 with a film thickness of 1 nm to form an electron injection layer 1115 was formed.

[0334] Finally, as the second electrode 1103 that functions as a cathode, aluminum was deposited to a film thickness of 200 nm to fabricate the light-emitting element 4 of this example. was fabricated.

[0335] In addition, in the above-described deposition process, all depositions used the resistance heating method.

[0336] (Comparative light-emitting element 5) The light-emitting layer 1113 of the comparative light-emitting element 5 was formed by co-depositing 2mDBTBPDBq-II, 4,4'-bis(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), and [Ir(dppm)2(acac)]. Here, the weight ratio of 2mDBTBPDBq-II, PCBNBB, and [Ir(dppm)2(acac)] was adjusted to be 0.8:0.2:0.05 (=2mDBTBPDBq-II:PCBNBB:[Ir(dppm)2(acac)]). Also, the film thickness of the light-emitting layer 1113 was set to 40 nm. naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine mine (abbreviation: PCBNBB), and [Ir(dppm)2(acac)] were co-deposited as and. Here, 2mDBTBPDBq-II, PCBNBB, and [Ir(dp pm)2(acac)] q-II:PCBNBB:[Ir(dppm)2(acac)]) was adjusted. Also, the film thickness of the light-emitting layer 1113 was 40 nm.

[0337] Except for the light-emitting layer 1113, it was fabricated in the same manner as the light-emitting element 4.

[0338] The element structure of the light-emitting element of this example obtained as described above is shown in Table 3.

[0339]

Table 3

[0340] The light-emitting element 4 and the comparative light-emitting element 5 were sealed with a glass substrate in a glove box under a nitrogen atmosphere so that each light-emitting element was not exposed to the atmosphere. After the operation, these light-emitting elements were sealed with a glass substrate so that each light-emitting element was not exposed to the atmosphere. After the operation, these light-emitting elements The operating characteristics of the child were measured. The measurement was performed at room temperature (atmosphere maintained at 25°C). It was done.

[0341] The luminance-current efficiency characteristics of the light-emitting element of this example are shown in FIG. 18. In FIG. 18, the horizontal axis represents the luminance (cd / m 2 ), and the vertical axis represents the current efficiency (cd / A). Also, the voltage-luminance characteristics are shown in FIG. 19 . In FIG. 19, the horizontal axis represents the voltage (V), and the vertical axis represents the luminance (cd / m 2 ). Also, the luminance -external quantum efficiency characteristics are shown in FIG. 20. In FIG. 20, the horizontal axis represents the luminance (cd / m 2 ), and the vertical axis represents the external quantum efficiency (%). Also, the voltage (V), current density (mA / cm 2 ), CIE chromaticity coordinates (x, y), current 2 efficiency (cd / A), power efficiency (lm / W), and external quantum efficiency (%) near a luminance of 1000 cd / m for each light-emitting element are shown in Table 4.

[0342]

Table 4

[0343] As shown in Table 4, the CIE chromaticity coordinates of the light-emitting element 4 at a luminance of 1000 cd / m 2 are (x, y) = (0.55, 0.45), and the CIE chromaticity coordinates of the comparative light-emitting element 5 at a luminance of 900 cd / m 2 are (x, y) = (0.55, 0.44). It was found that the light-emitting element of this example obtained orange light emission derived from [Ir(dppm)2(acac)]. From FIGS. 18 to 20 and Table 4, it was found that both the light-emitting element 4 and the comparative light-emitting element 5 have a low driving voltage

[0344] and high current efficiency and external quantum efficiency. ​

[0345] Next, reliability tests were conducted on the light-emitting element 4 and the comparative light-emitting element 5. The results of the reliability tests are shown in Fig. 21 (A)(B). In Fig. 21(A)(B), the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%, and the horizontal axis represents the driving time (h) of the element. The reliability test was carried out at room temperature and the initial luminance was set to 5000 cd / m . Under the condition of constant current density, the light-emitting element of this example was driven 2 . From Fig. 21(A)(B), the luminance of the light-emitting element 4 after 370 hours was maintained at 94% of the initial luminance, and the luminance of the comparative light-emitting element 5 after 460 hours was maintained at 92% of the initial luminance . From the results of this reliability test, it became clear that the light-emitting element 4 has a longer lifespan than the comparative light-emitting element 5 . As described above, by using the PCBNBF fabricated in Example 1 as the light-emitting layer, a light-emitting element with a long lifespan could be fabricated .

[0346] (Reference Example)

[0347] The synthesis method of 4,6-bis[3-(dibenzothiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) used in Example 4 will be described

[0348] .

Chemical formula

[0349]

[0350] The synthesis scheme of 4,6mDBTP2Pm-II is shown in (x-1)

Chemical formula

[0351] ​​In a 100 mL eggplant flask, 1.0 g (6.7 mmol) of 4,6-dichloropyrimidine was added to 5.1 g (17 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 3.5 g (34 mmol) of sodium carbonate, 20 mL of 1,3-dimethyl-3, 4,5,6-tetrahydro-2(1H)-pyrimidinone (abbreviation: DMPU), and 10 mL of water. The mixture was degassed by stirring under reduced pressure. To this mixture was added 56 m g (81 μmol) of bis(triphenylphosphine)palladium(II) dichloride and the atmosphere was replaced with argon. The reaction vessel was irradiated with microwave (2.45 GHz, 100 W) for 1 hour and 30 minutes while stirring to heat. After heating, water was added to this mixture and it was filtered to obtain a filtrate. The obtained solid was washed with dichloromethane and ethanol. Toluene was added to the obtained solid and it was suction filtered through celite, alumina, and florisil, and the filtrate was concentrated to obtain a solid. The obtained solid was recrystallized using toluene to obtain 2.5 g of a white solid in a yield of 63%.

[0352] The 2.5 g of the obtained solid was purified by sublimation using the train sublimation method. It was carried out by heating at 300 °C under the conditions of a pressure of 3.6 P a and an argon flow rate of 5 mL / min. After sublimation purification, 2.0 g of a white solid was obtained in a recovery rate of 79%.

[0353] By nuclear magnetic resonance method (NMR), it was confirmed that this compound was the target 4,6-bis[3-(dibenz othiophen-4-yl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-I I).

[0354] The 1 1H NMR data of the obtained substance are shown below. 1 1H NMR (CDCl3, 300 MHz): δ = 7.41 - 7.51 (m, 4H), 7.58 - 7.62 (m, 4H), 7.68 - 7.79 (m, 4H), 8.73 (dt, J1 = 8.4 Hz, J2 = 0.9 Hz, 2H), 8.18 - 8.27 (m, 7H), 8. 54 (t, J1 = 1.5 Hz, 2H), 9.39 (d, J1 = 0.9 Hz, 1H).

Explanation of Symbols

[0355] 201 First electrode 203 EL layer 203a EL layer 203b EL layer 205 Second electrode 207 Intermediate layer 213 Light-emitting layer 221 First organic compound 222 Second organic compound 223 Phosphorescent compound 301 Hole injection layer 302 Hole transport layer 303 Light-emitting layer 304 Electron transport layer 305 Electron injection layer 306 Electron injection buffer layer 307 Electron relay layer 308 Charge generation region 401 Support substrate 403 Light-emitting element 405 Encapsulation substrate 407 Encapsulant 409a First terminal 409b Second terminal 411a Light extraction structure 411b Light extraction structure 413 Planarization layer 415 Space 417 Auxiliary wiring 419 Insulating layer 421 First electrode 423 EL layer 425 Second electrode 501 Support substrate 503 Light-emitting element 505 Encapsulation substrate 507 Encapsulant 509 FPC 511 Insulating layer 513 Insulating layer 515 Space 517 Wiring 519 Partition wall 521 First electrode 523 EL layer 525 Second electrode 531 Black matrix 533 Color filter 535 Overcoat layer 541a Transistor 541b Transistor 542 Transistor 543 Transistor 551 Light-emitting part 552 Driving circuit part 553 Driving circuit part 1100 Glass substrate 1101 First electrode 1103 Second electrode 1111 Hole injection layer 1112 Hole transport layer 1113 Light-emitting layer 1114 Electron transport layer 1115 Electron injection layer 7100 Television device 7101 Housing 7102 Display part 7103 Stand 7111 Remote control operation unit 7200 Computer 7201 Main body 7202 Housing 7203 Display part 7204 Keyboard 7205 External connection port 7206 Pointing device 7300 Portable game machine 7301a Housing 7301b Housing 7302 Connecting Part 7303a Display Part 7303b Display Part 7304 Speaker Part 7305 Recording Medium Insertion Part 7306 Operation Key 7307 Connection Terminal 7308 Sensor 7400 Mobile Phone 7401 Housing 7402 Display Part 7403 Operation Button 7404 External Connection Port 7405 Speaker 7406 Microphone 7500 Tablet Terminal 7501a Housing 7501b Housing 7502a Display Part 7502b Display Part 7503 Shaft Part 7504 Power Supply 7505 Operation Key 7506 Speaker 7601 Lighting Part 7602 Umbrella 7603 Variable Arm 7604 Support 7605 Base 7606 Power Supply 7701 Lighting Fixture 7702 Lighting Fixture 7703 Desktop Lighting Fixture

Claims

1. A light-emitting layer is disposed between a pair of electrodes, the light-emitting layer includes a first organic compound represented by Formula (G0), a second organic compound that forms an exciplex with the first organic compound, and an iridium complex. 【Chemistry 1】 (In formula (G0), Ar １ represents a naphthyl group, Ar ２ represents a carbazolyl group, Ar ３ represents a fluorenyl group or a spirofluorenyl group, α １ and α ２ each independently represents a phenylene group or a biphenyldiyl group, and the naphthyl group, the carbazolyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyldiyl group are each independently unsubstituted or have an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

2. A light-emitting layer is disposed between a pair of electrodes, the light-emitting layer includes a first organic compound represented by Formula (G1), a second organic compound that forms an exciplex with the first organic compound, and an iridium complex. 【Chemistry 2】 (In formula (G1), Ar １ represents a naphthyl group, Ar ３ represents a fluorenyl group or a spirofluorenyl group; Ar ４ represents an aryl group having 6 to 25 carbon atoms, α １ represents a phenylene group or a biphenyldiyl group, R １１ ~R １７ and R ２１ ~R ２４ each independently represents hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and the naphthyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyldiyl group are each independently unsubstituted or have an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms as a substituent.

3. A light-emitting layer is disposed between a pair of electrodes, the light-emitting layer includes a first organic compound represented by Formula (G2), a second organic compound that forms an exciplex with the first organic compound, and an iridium complex. 【Chemistry 3】 (In formula (G2), Ar １ represents a naphthyl group, Ar ３ represents a fluorenyl group or a spirofluorenyl group, α １ represents a phenylene group or a biphenyldiyl group, R １１ ~R １７ , and R ２１ ~R ２４ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms; R ３１ ~R ３５ each independently represents hydrogen or an alkyl group having 1 to 10 carbon atoms, and the naphthyl group, the fluorenyl group, the spirofluorenyl group, the phenylene group, and the biphenyldiyl group are each independently unsubstituted or have an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

4. A light-emitting layer is disposed between a pair of electrodes, the light-emitting layer includes a first organic compound represented by Formula (G3), a second organic compound that forms an exciplex with the first organic compound, and an iridium complex. 【Chemistry 4】 (In formula (G3), Ar ３ represents a fluorenyl group or a spirofluorenyl group; R １１ ~R １７ , R ２１ ~R ２４ , R ４１ ~R ４７ , and R ５１ ~R ５４ each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 25 carbon atoms; R ３１ ~R ３５ each independently represents hydrogen or an alkyl group having 1 to 10 carbon atoms, and the fluorenyl group or the spirofluorenyl group is unsubstituted or has an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 25 carbon atoms as a substituent.

5. A light emitting device having the light emitting element according to claim 1 in a light emitting portion.

6. An electronic device having the light emitting device according to claim 5 in a display section.

7. An illumination device having the light emitting device according to claim 5 as a light emitting portion.

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