Organic Compounds and Light-Emitting Devices

Abstract

To provide an organic compound having a stable excited state and high light emission efficiency.SOLUTION: An organic compound represented by general Formula (G1) is provided, where Q1 represents sulfur or oxygen. In addition, R1 to R5 each independently represent hydrogen, deuterium, a substituted or unsubstituted 1-10C alkyl group, a substituted or unsubstituted 3-10C cycloalkyl group, a substituted or unsubstituted 6-10C polycyclic alkyl group, a substituted or unsubstituted 6-30C aryl group, or a substituted or unsubstituted 2-30C heteroaryl group. In addition, A1 represents a 6-100C aryl group including a substituted or unsubstituted substituent, or a 2-100C heteroaryl group including a substituted or unsubstituted substituent. At least one of hydrogen contained in R1 to R5 and A1 is substituted with deuterium.SELECTED DRAWING: None

Description

Technical field

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting device, a light-emitting device, a light-receiving and emitting device, a display device, an electronic device, a lighting device, and an electronic device. Note that one embodiment of the present invention is not limited to the above technical field. A technical field of one embodiment of the invention disclosed in this specification and the like relates to a product, a method, or a manufacturing method. Alternatively, one aspect of the present invention relates to a process, machine, manufacture, or composition of matter. Therefore, the technical field of one embodiment of the present invention disclosed in this specification more specifically includes semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, imaging devices, and the like. Driving methods or their manufacturing methods can be mentioned as an example. [Background technology]

[0002] Light-emitting devices (organic EL elements) utilizing electroluminescence (EL) using organic compounds have been put to practical use. The basic structure of these light-emitting devices is to sandwich an organic compound layer (EL layer) containing a light-emitting material between a pair of electrodes. By applying a voltage to this element to inject carriers and utilizing recombination energy of the carriers, light emission from the light-emitting material can be obtained.

[0003] Since such a light-emitting device is self-luminous, it has higher visibility than a liquid crystal display and is suitable as a pixel of a display. Further, a display using such a light-emitting device has the great advantage that it does not require a backlight and can be manufactured to be thin and light. Another feature is its extremely fast response speed.

[0004] In addition, since these light-emitting devices can continuously form light-emitting layers two-dimensionally, planar light emission can be obtained. This is a feature that is difficult to obtain with point light sources such as incandescent lamps or LEDs, or linear light sources such as fluorescent lamps, so it is also highly useful as a surface light source that can be applied to lighting and the like.

[0005] A display or a lighting device using such a light-emitting device is suitable for application to various electronic devices, and research and development are proceeding in search of a light-emitting device having better efficiency and life.

[0006] Although the properties of light emitting devices have improved remarkably, they are still insufficient to meet the high demands on any property, including efficiency or durability. In particular, in order to solve problems such as burn-in, which are problems specific to EL, the smaller the decrease in efficiency due to deterioration, the better.

[0007] Deterioration is greatly affected by the luminescent center substance and its peripheral materials, and therefore, the development of host materials with good properties is being actively pursued.

[0008] For example, an organic compound having an indolocarbazole skeleton has been disclosed as a host material (Patent Documents 1 and 2). An organic compound having an indolocarbazole skeleton has a high glass transition point, and good characteristics can be obtained by using it in a light-emitting device. However, in order to suppress deterioration of light-emitting devices, materials with higher heat resistance and longer life are required.

[0009] Further, a technique of substituting deuterium for hydrogen contained in a host material (deuteration) is disclosed (Patent Document 3). Deuteration of the host material is effective for prolonging the life of the light-emitting device, but there are problems such as complicating the synthesis route or requiring high temperature and high pressure for the synthesis. [Prior art documents] [Patent document]

[0010] [Patent document 1] WO2018 / 198844 [Patent document 2] WO2018 / 123783 [Patent Document 3] Special table 2013-503860 [Outline of the invention] [Problems to be solved by the invention]

[0011] An object of one embodiment of the present invention is to provide a novel organic compound. Another object of one embodiment of the present invention is to provide an organic compound whose excited state is stable. Another object of one embodiment of the present invention is to provide an organic compound that can be used as a host material for dispersing a light-emitting substance. Another object of one embodiment of the present invention is to provide an organic compound that can be easily synthesized. Another object of one embodiment of the present invention is to provide a light-emitting device with a long driving lifetime. Another object of one embodiment of the present invention is to provide a novel light-emitting device. Another object of one embodiment of the present invention is to reduce the manufacturing cost of a light-emitting device. Another object of one embodiment of the present invention is to provide a light-emitting device, an electronic device, or a lighting device with low power consumption.

[0012] Another object of one embodiment of the present invention is to provide an organic compound in which a partial structure is selectively deuterated. Another object of one embodiment of the present invention is to provide an organic compound in which a partial structure is selectively deuterated so that the effect of extending the lifetime can be obtained. Another object of one embodiment of the present invention is to carry out molecular design that can reduce the complexity of synthetic routes, high temperature and high pressure in synthesis, etc., and to synthesize an organic compound with such a molecular design. do.

[0013] The description of these problems does not preclude the existence of other problems. Note that one embodiment of the present invention does not necessarily solve all of these problems. Problems other than these are self-evident from the descriptions of the specification, drawings, claims, etc., and it is possible to extract problems other than these from the descriptions of the specification, drawings, claims, etc. is. [Means for solving the problem]

[0014] One embodiment of the present invention is an organic compound represented by General Formula (G1).

[0015] [formation]

[0016] In the above general formula (G1), Q 1 represents sulfur or oxygen, and R 1 thru R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; 1 represents an aryl group having 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group having 2 to 100 carbon atoms containing a substituted or unsubstituted substituent; 1 thru R 5 , and A 1 has at least one hydrogen replaced by deuterium.

[0017] One embodiment of the present invention is an organic compound represented by General Formula (G1).

[0018] [formation]

[0019] However, in the above general formula (G1), Q 1 represents sulfur or oxygen, and R 1 , R 2 , R 4 , and R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; 1 represents an aryl group having 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group having 2 to 100 carbon atoms containing a substituted or unsubstituted substituent; 3 A 1 at least one of the hydrogens of the R 1 thru R 5 has at least one hydrogen replaced by deuterium.

[0020] One embodiment of the present invention is an organic compound represented by General Formula (G2).

[0021] [formation]

[0022] However, in the above general formula (G2), Q 1 represents sulfur or oxygen, and R 1 , R 2 , R 4 , and R5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group, where α is a substituted or unsubstituted C6-C25 represents an arylene group or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms, m represents an integer of 0 to 4, A 2 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R 3 represents an aryl group having 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group having 2 to 100 carbon atoms containing a substituted or unsubstituted substituent, α, A 2 , and R 3 At least one of the hydrogens in is deuterium.

[0023] Further, in one aspect of the present invention, in each of the above structures, α is an arylene group having 6 to 25 carbon atoms or a heteroarylene group having 2 to 25 carbon atoms, each independently represented by formulas (α-1) to (α -20) is an organic compound represented by any one of

[0024] [formation]

[0025] One embodiment of the present invention is an organic compound represented by General Formula (G3).

[0026] [formation]

[0027] However, in the above general formula (G3), Q 1 represents sulfur or oxygen, and R 1 , R 2 , and R 4 thru R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; 3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, m represents an integer of 0 to 4, and A 3 Hydrogen possessed by and R 1 , R 2 , and R 4 thru R 14 is deuterium.

[0028] One embodiment of the present invention is an organic compound represented by General Formula (G4).

[0029] [formation]

[0030] However, in the above general formula (G4), Q 1 and Q 2 each independently represents sulfur or oxygen, and R 1 , R 2 , and R 4 thru R 21 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, m represents an integer of 0 to 4, R 1 , R 2 , and R 4 thru R 21 is deuterium.

[0031] Further, one aspect of the present invention is the above A 1 and R 3 are organic compounds with the same structure.

[0032] Another embodiment of the present invention is an organic compound in which, in each of the above structures, at least one hydrogen other than the hydrogen directly bonded to the benzofuropyrimidine skeleton is deuterium.

[0033] Another embodiment of the present invention is, in each of the above structures, an organic compound in which all hydrogen atoms in the molecular structure are deuterium atoms.

[0034] Further, in one aspect of the present invention, in each of the above structures, the aryl group having 6 to 30 carbon atoms or the heteroaryl group having 2 to 30 carbon atoms is each independently represented by formulas (Ar-1) to (Ar-80) It is an organic compound represented by any one of

[0035] [formation]

[0036] [formation]

[0037] [formation]

[0038] One aspect of the present invention is an organic compound represented by Structural Formula (100), (101) or (128).

[0039] [formation]

[0040] Another embodiment of the present invention is a light-emitting device using the organic compound having any of the above structures.

[0041] Another embodiment of the present invention is a light-emitting device including a light-emitting device having any of the above structures, a transistor, or a substrate.

[0042] Another embodiment of the present invention is an electronic device including the light-emitting device having any of the above structures, and a detection portion, an input portion, or a communication portion.

[0043] Another embodiment of the present invention is a lighting device including the light-emitting device having the above structure, the above electronic device, and a housing.

Effect of the invention

[0044] One aspect of the present invention can provide novel organic compounds. Further, according to one embodiment of the present invention, a stable organic compound that is unlikely to react from an excited state can be provided. Further, according to one embodiment of the present invention, an organic compound that can be used as a host material can be provided. Further, according to one embodiment of the present invention, an organic compound that can be easily synthesized can be provided. Further, according to one embodiment of the present invention, a novel light-emitting device can be provided. Further, according to one embodiment of the present invention, a light-emitting device with long driving life can be provided. Further, according to one embodiment of the present invention, the manufacturing cost of the light-emitting device can be reduced. Further, according to one embodiment of the present invention, a light-emitting device, an electronic device, or a lighting device with low power consumption can be provided.

[0045] Further, according to one embodiment of the present invention, an organic compound whose partial structure is selectively deuterated can be provided. Further, according to one embodiment of the present invention, an organic compound in which a partial structure with an effect of prolonging the lifetime is selectively deuterated can be provided. As a result, it is possible to reduce the complexity of the synthetic route and the increase in temperature and pressure in the synthetic route, which are caused when all the hydrogen in the organic compound is replaced with deuterium.

[0046] Note that the description of these effects does not preclude the existence of other effects. Note that one embodiment of the present invention does not necessarily have all of these effects. Effects other than these are self-evident from the descriptions of the specification, drawings, claims, etc., and it is possible to extract effects other than these from the descriptions of the specification, drawings, claims, etc. is. [Brief description of the drawing]

[0047]

Figure 1

Figure 2

[0048] (Embodiment 1) In this embodiment, an organic compound and a thin film that are one embodiment of the present invention will be described.

[0049] One embodiment of the present invention is a bipolar substance having both a hole-transporting skeleton and an electron-transporting skeleton, which is an organic compound in which the hole-transporting skeleton is deuterated. Specifically, one embodiment of the present invention is a bipolar substance having a benzofuropyrimidine skeleton as an electron-transporting skeleton and a deuterated dibenzothiophene skeleton or a deuterated dibenzofuran skeleton as a hole-transporting skeleton. is. One embodiment of the present invention has both a hole-transporting skeleton and an electron-transporting skeleton, and thus has both hole-transporting and electron-transporting properties. Therefore, for example, it can be suitably used as a host material for a light-emitting layer of a light-emitting device. Moreover, it can be suitably used for a hole transport layer and an electron transport layer as the transport layer in contact with the light-emitting layer.

[0050] In this specification and the like, deuteration means that at least one hydrogen (H) in an organic compound is replaced with deuterium (D). The bond dissociation energy of the bond between carbon and deuterium (C-D bond) is larger than the bond dissociation energy of the bond between carbon and hydrogen (C-H bond), and is stable and difficult to break. Therefore, by deuterating the hole-transporting skeleton in one embodiment of the present invention, dissociation of the carbon-hydrogen bond of the hole-transporting skeleton in the ground state or excited state can be suppressed. In addition, deterioration or alteration of the organic compound due to dissociation of the carbon-hydrogen bond in the hole-transporting skeleton can be suppressed.

[0051] Further, since the organic compound of one embodiment of the present invention has a hole-transporting skeleton, when the organic compound of one embodiment of the present invention is used as a host material in a light-emitting device, for example, the hole-transporting skeleton receives holes. There is In giving and receiving holes, the carbon-hydrogen bond is likely to dissociate in some cases. can be prevented.

[0052] In addition, in the synthesis of an organic compound in which the entire structure of a bipolar substance having a hole-transporting skeleton and an electron-transporting skeleton is deuterated, the route becomes complicated, or high temperature and high pressure are required. There's a problem. Therefore, according to one embodiment of the present invention, selective deuteration of only the hole-transporting skeleton enables easy synthesis and cost reduction.

[0053] In this specification and the like, the deuteration ratio of the hole-transporting skeleton indicates the ratio of hydrogen directly bonded to the hole-transporting skeleton replaced with deuterium. For example, when 10% of the hydrogens directly bonded to the hole-transporting skeleton are replaced with deuterium, the deuteration rate of the hole-transporting skeleton is 10%. Further, when the hole-transporting skeleton has a substituent, the hydrogen or deuterium of the substituent is not used for calculating the deuteration rate of the hole-transporting skeleton. For example, when only deuterium and a phenyl group are directly bonded to a hole-transporting skeleton, the deuteration rate of the hole-transporting skeleton is 100, regardless of the ratio of hydrogen and deuterium in the phenyl group. %.

[0054] Moreover, as the benzofuropyrimidine skeleton, specifically, a benzofuro[3,2-d]pyrimidine skeleton and the like can be mentioned, but it is not limited thereto.

[0055] Further, the organic compound of one embodiment of the present invention has excellent carrier-transport properties. Therefore, it is possible to provide a light-emitting device with a low driving voltage. Also, an electronic device with low power consumption can be provided.

[0056] Further, since the organic compound of one embodiment of the present invention has a high triplet excitation level (T1 level), it can be suitably used for a light-emitting device using a phosphorescent substance. Specifically, the organic compound of one embodiment of the present invention is preferably used as a host material for a light-emitting device.

[0057] When the organic compound of one embodiment of the present invention is used as a host material, the organic compound has a high triplet excitation level (T1 level), so that the excitation energy of the phosphorescent substance is transferred to the organic compound. is suppressed, and the excitation energy can be effectively converted into luminescence. Note that an iridium complex can be used as the phosphorescent substance, for example. Therefore, a highly efficient light emitting device can be provided.

[0058] Moreover, it can be suitably used not only as a host material in a light emitting layer but also as a carrier transport layer (hole transport layer or electron transport layer).

[0059] Further, since the organic compound of one embodiment of the present invention has a hole-transporting skeleton, when the organic compound of one embodiment of the present invention is used in a light-emitting device as a host material in which a light-emitting substance is dispersed, for example, the hole-transporting skeleton does not exist. It may accept holes. In giving and receiving holes, the carbon-hydrogen bond is likely to dissociate in some cases. can be prevented. Further, since the organic compound of one embodiment of the present invention has both a hole-transporting skeleton and an electron-transporting skeleton, it can accept both electrons and holes. Therefore, the organic compound of one embodiment of the present invention is efficiently brought into an excited state by recombination of carriers. Therefore, by using the organic compound of one embodiment of the present invention as a host material in which a light-emitting substance is dispersed in a light-emitting device, a highly efficient light-emitting device can be provided.

[0060] <Example 1 of organic compound> One embodiment of the present invention is an organic compound represented by General Formula (G1).

[0061] [formation]

[0062] However, in the above general formula (G1), Q 1 represents sulfur or oxygen. Also, R 1 thru R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Also, A 1 represents an aryl group of 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group of 2 to 100 carbon atoms containing a substituted or unsubstituted substituent. Also, R 1 thru R 5 , and A 1 At least one of the hydrogens in is replaced with deuterium.

[0063] Further, in the above general formula (G1), R 1 thru R 5 Examples of the alkyl group substituted with include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert -pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, etc. can.

[0064] Further, in the above general formula (G1), R 1 thru R 5 Examples of the cycloalkyl group or polycyclic alkyl group substituted with include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a cycloheptyl group, and an adamantyl group.

[0065] In addition, in the above general formula (G1), A 1 or R 1 thru R 5 Examples of the aryl group or heteroaryl group substituted with are phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1 -naphthyl, 2-naphthyl, fluorenyl, acenaphthylenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylenyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, bipyridinyl, phenanthrolinyl quinoxalinyl group, dibenzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, dibenzoquinazolinyl group, imidazolyl group, triazolyl group, oxadiazolyl group, benzimidazolyl group, furopyrimidyl group, furopyrazyl group, furopyridazyl group, benzofuro pyrimidinyl group, benzofuropyrazinyl group, benzofuropyridazinyl group, thienyl group, furanyl group, benzothiophen-yl group, benzofuran-yl group, dibenzothiophen-yl group, dibenzofuran-yl group, benzonaphthothiophene- Examples include an yl group, a benzonaphthofuran-yl group, a dinaphthothiophen-yl group, a dinaphthofuran-yl group, and the like.

[0066] The organic compound represented by the general formula (G1), which is one embodiment of the present invention, is R 1 thru R 5 , and A 1 Since at least one of the hydrogens in is replaced with deuterium, deterioration or alteration of the organic compound can be suppressed. In addition, since dissociation of carbon-hydrogen bonds in an excited state can be suppressed, it can be suitably used as a host material for dispersing a light-emitting substance of a light-emitting device.

[0067] Further, when the organic compound of one embodiment of the present invention is used as a host material in a light-emitting device, the hole-transporting skeleton may receive holes. Carbon-hydrogen bonds tend to be easily dissociated in giving and receiving holes. It is suitable because it can be prevented.

[0068] <Example of organic compound 2> One embodiment of the present invention is an organic compound represented by General Formula (G1).

[0069] [formation]

[0070] However, in the above general formula (G1), Q 1 represents sulfur or oxygen. Also, R 1 , R 2 , R 4 and R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Also, A 1 represents an aryl group of 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group of 2 to 100 carbon atoms containing a substituted or unsubstituted substituent. Also, R 3 represents an aryl group of 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group of 2 to 100 carbon atoms containing a substituted or unsubstituted substituent. Also, A 1 at least one of the hydrogens of the R 1 thru R 5 has at least one hydrogen replaced by deuterium.

[0071] In addition, in the above general formula (G1), A 1 , R 1 , R 2 , R 4 and R 5 As the substituent to be substituted with , the same substituent as the substituent having the same symbol in the general formula (G1) in <Example of organic compound 1> can be mentioned, and the above is referred to.

[0072] Further, in the above general formula (G1), R 3 Examples of aryl groups substituted with include phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, o-biphenyl, m-biphenyl, p-biphenyl, 1-naphthyl, 2 -naphthyl group, fluorenyl group, acenaphthylenyl group, anthryl group, phenanthryl group, terphenyl group, triphenylenyl group, and heteroaryl group includes pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, bipyridinyl group, phenanthrolinyl group. quinoxalinyl group, dibenzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, dibenzoquinazolinyl group, imidazolyl group, triazolyl group, oxadiazolyl group, benzimidazolyl group, furopyrimidyl group, furopyrazyl group, furopyridazyl group, benzofuro pyrimidinyl group, benzofuropyrazinyl group, benzofuropyridazinyl group, thienyl group, furanyl group, benzothiophen-yl group, benzofuran-yl group, dibenzothiophen-yl group, dibenzofuran-yl group, benzonaphthothiophene- Examples include an yl group, a benzonaphthofuran-yl group, a dinaphthothiophen-yl group, a dinaphthofuran-yl group, and the like.

[0073] The organic compound represented by the general formula (G1), which is one embodiment of the present invention, is R 1 thru R 5 , and A 1 Since at least one of the hydrogens in is replaced with deuterium, deterioration or alteration of the organic compound can be suppressed. In addition, since dissociation of carbon-hydrogen bonds in an excited state can be suppressed, it can be suitably used as a host material for dispersing a light-emitting substance of a light-emitting device.

[0074] Further, when the organic compound of one embodiment of the present invention is used as a host material in a light-emitting device, the hole-transporting skeleton may receive holes. Carbon-hydrogen bonds tend to be easily dissociated in giving and receiving holes. It is suitable because it can be prevented.

[0075] <Example 3 of organic compound> One embodiment of the present invention is an organic compound represented by General Formula (G2).

[0076] [formation]

[0077] However, in the above general formula (G2), Q 1 represents sulfur or oxygen. Also, R 1 , R 2 , R 4 , and R 5are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. α represents a substituted or unsubstituted C6-C25 arylene group or a substituted or unsubstituted C2-C25 heteroarylene group. Also, m represents an integer of 0 to 4. Also, A 2 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Also, R 3 represents an aryl group of 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group of 2 to 100 carbon atoms containing a substituted or unsubstituted substituent. Also, α, A 2 , and R 3 At least one of the hydrogens in is deuterium.

[0078] In addition, in the above general formula (G2), A 1 , and R 1 thru R 5 For the substituent to be substituted with , reference can be made to the substituents that can be used for the same symbol in general formula (G1) described in <Example of organic compound 1> or <Example of organic compound 2>.

[0079] In the above general formula (G2), A 2 Examples of aryl groups substituted with include phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, o-biphenyl, m-biphenyl, p-biphenyl, 1-naphthyl, 2 -naphthyl group, fluorenyl group, acenaphthylenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group; nantholinyl group, quinoxalinyl group, dibenzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, dibenzoquinazolinyl group, imidazolyl group, triazolyl group, oxadiazolyl group, benzimidazolyl group, furopyrimidyl group, furopyrazyl group, furopyridazyl group , benzofuropyrimidinyl group, benzofuropyrazinyl group, benzofuropyridazinyl group, thienyl group, furanyl group, benzothiophen-yl group, benzofuran-yl group, dibenzothiophen-yl group, dibenzofuran-yl group, benzo A naphthothiophen-yl group, a benzonaphthofuran-yl group, a dinaphthothiophene-yl group, a dinaphthofuran-yl group and the like can be mentioned.

[0080] In the general formula (G2) above, the arylene group substituted for α includes a phenylene group, a toluylene group, a dimethylphenylene group, a trimethylphenylene group, a tetramethylphenylene group, a biphenylene group, a terphenylene group, a quaterphenylene group, and a naphthylene group. , a fluorenylene group, a phenanthrenylene group, a triphenylenylene group, a benzo[a]phenanthrenylene group, a benzo[c]phenanthrenylene group, etc., and the heteroarylene group includes a pyrimidine-diyl group. , pyrazine-diyl group, pyridazine-diyl group, triazine-diyl group, bipyridine-diyl group, phenanthroline-diyl group, quinoxaline-diyl group, dibenzoquinoxaline-diyl group, quinazoline-diyl group, benzoquinazoline-diyl group, dibenzoquinazoline-diyl group, imidazole-diyl group, triazole-diyl group, oxadiazole-diyl group, benzimidazole-diyl group, furodiazine-diyl group, benzofuropyrimidine-diyl group, thiophene-diyl group, furan-diyl group, benzo thiophene-diyl group, benzofuran-diyl group, dibenzothiophene-diyl group, dibenzofuran-diyl group, benzonaphtho-thiophene-diyl group, benzonaphtho-furan-diyl group, dinaphtho-thiophene-diyl group, dinaphtho-furan-diyl group, etc. can be mentioned.

[0081] In the above general formula (G2), when m is 0, the highest occupied molecular orbital (HOMO) level tends to be deep, and when m is 1 or more and 4 or less, the HOMO level is It tends to be shallow. By changing m in this way, it is possible to change the HOMO level of the organic compound. In addition, when m is 2 or more and 4 or less, the molecular weight is larger than when m is 0 or 1, so the heat resistance is high, and when the film is thinned, the film quality is less likely to crystallize and is stable, which is preferable. As a result, it is possible to provide a highly reliable device.

[0082] On the other hand, when m is 0 or 1, the molecular weight does not become too large, so the sublimability can be improved, and decomposition during vapor deposition can be prevented, so that a highly pure thin film can be provided, which is preferable. As a result, it is possible to provide a highly reliable device.

[0083] In general formulas (G1) and (G2) above, the arylene group having 6 to 30 carbon atoms and the heteroarylene group having 2 to 30 carbon atoms are each independently represented by structural formulas (α-1) to (α-20 ) is preferably represented by any one of

[0084] [formation]

[0085] The substituents represented by the structural formulas (α-1) to (α-20) are examples of an arylene group having 6 to 25 carbon atoms or a heteroarylene group having 2 to 25 carbon atoms. An arylene group having 6 to 25 carbon atoms or a heteroarylene group having 2 to 25 carbon atoms that can be used in general formula (G2) is not limited to these. When having an arylene group or a heteroarylene group as a substituent, the HOMO level can be changed to adjust carrier balance or improve heat resistance.

[0086] In the general formula (G2), when the arylene group having 6 to 25 carbon atoms or the heteroarylene group having 2 to 25 carbon atoms has a substituent, the substituent is a linear alkyl group having 1 to 6 carbon atoms. , a branched alkyl group having 1 to 6 carbon atoms, a cyclic or polycyclic alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. When having an alkyl group as a substituent, general formula (G2) can lower the refractive index. Further, when having an aryl group as a substituent, general formula (G2) can improve heat resistance.

[0087] The organic compound represented by the general formula (G2), which is one embodiment of the present invention, includes α, A 2 , and R 3 Since at least one of the hydrogens in is replaced with deuterium, deterioration of the organic compound or change in molecular structure can be suppressed. In addition, since dissociation of carbon-hydrogen bonds in an excited state can be suppressed, a compound with a stable excited state can be provided. It is preferable to use such a compound as a host material for dispersing a light-emitting substance of a light-emitting device, because a highly reliable device having a long driving life can be provided.

[0088] Further, when the organic compound of one embodiment of the present invention is used as a host material in a light-emitting device, the hole-transporting skeleton may receive holes. A carbon-hydrogen bond is likely to dissociate in giving and receiving holes in some cases. This is preferable because dissociation of bonds can be prevented.

[0089] <Example 4 of organic compound> One embodiment of the present invention is an organic compound represented by General Formula (G3).

[0090] [formation]

[0091] However, in the above general formula (G3), Q 1 represents sulfur or oxygen. Also, R 1 , R 2 and R 4 thru R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Also, A 3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. m represents an integer from 0 to 4, A 3 Hydrogen possessed by and R 1 , R 2 and R 4 thru R 14 is deuterium.

[0092] In addition, in the above general formula (G3), A 1 , A 2 , R 1 , R 2 , R 4 and R 5 As the substituent to be substituted with , the same substituent as the substituent having the same symbol in the general formula (G1) in <Example of organic compound 1> can be mentioned, and the above is referred to.

[0093] In addition, in the above general formula (G3), A 3Examples of aryl groups substituted with include phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, o-biphenyl, m-biphenyl, p-biphenyl, 1-naphthyl, 2 -naphthyl group, fluorenyl group, acenaphthylenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group; nantholinyl group, quinoxalinyl group, dibenzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, dibenzoquinazolinyl group, imidazolyl group, triazolyl group, oxadiazolyl group, benzimidazolyl group, furopyrimidyl group, furopyrazyl group, furopyridazyl group , benzofuropyrimidinyl group, benzofuropyrazinyl group, benzofuropyridazinyl group, thienyl group, furanyl group, benzothiophen-yl group, benzofuran-yl group, dibenzothiophen-yl group, dibenzofuran-yl group, benzo A naphthothiophen-yl group, a benzonaphthofuran-yl group, a dinaphthothiophene-yl group, a dinaphthofuran-yl group and the like can be mentioned.

[0094] Also, in the above general formula (G3), R 6 thru R 14 Linear or branched alkyl groups to be substituted with include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec -pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group , etc. can be mentioned.

[0095] Also, in the above general formula (G3), R 6 thru R 14 Examples of the cycloalkyl group or polycyclic alkyl group substituted with include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a cycloheptyl group, and an adamantyl group.

[0096] Also, in the above general formula (G3), R 6 thru R 14 Examples of aryl groups substituted with include phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, o-biphenyl, m-biphenyl, p-biphenyl, 1-naphthyl, 2 -naphthyl group, fluorenyl group, acenaphthylenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group; nantholinyl group, quinoxalinyl group, dibenzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, dibenzoquinazolinyl group, imidazolyl group, triazolyl group, oxadiazolyl group, benzimidazolyl group, furopyrimidyl group, furopyrazyl group, furopyridazyl group , a benzofuropyrimidinyl group, and the like.

[0097] The organic compound represented by the general formula (G3), which is one embodiment of the present invention, is A 3 Hydrogen possessed by and R 1 , R 2 and R 4 thru R 14 Since at least one of the hydrogens in is replaced with deuterium, deterioration or alteration of the organic compound can be suppressed. In addition, since dissociation of carbon-hydrogen bonds in an excited state can be suppressed, it can be suitably used as a host material for dispersing a light-emitting substance of a light-emitting device.

[0098] Further, when the organic compound of one embodiment of the present invention is used as a host material in a light-emitting device, the hole-transporting skeleton may receive holes. Carbon-hydrogen bonds tend to be easily dissociated in giving and receiving holes. It is suitable because it can be prevented.

[0099] <Example 5 of organic compound> One embodiment of the present invention is an organic compound represented by General Formula (G4).

[0100] [formation]

[0101] However, in the above general formula (G4), Q 1 and Q 2 each independently represents sulfur or oxygen. Also, R 1 , R 2 , and R 4 thru R 21 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Also, m represents an integer of 0 to 4. R. 1 , R 2 , and R 4 thru R 21 is deuterium.

[0102] In addition, in the above general formula (G4), R 1 , R 2 , and R 4 thru R 21 Examples of the alkyl group substituted with include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert -Pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, etc. can be done.

[0103] Further, in the above general formula (G4), R 1 , R 2 , and R 4 thru R 21 Examples of the cycloalkyl group or polycyclic alkyl group substituted with include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a cycloheptyl group, and an adamantyl group.

[0104] Further, in the above general formula (G4), R 1 , R 2 , and R 4 thru R 21 The aryl group substituted with a phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group, acenaphthylenyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, triphenylenyl group; phenanthrolinyl group, quinoxalinyl group, dibenzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, dibenzoquinazolinyl group, imidazolyl group, triazolyl group, oxadiazolyl group, benzimidazolyl group, furopyrimidyl group, furopyrazyl group, furopyridazyl a benzofuropyrimidinyl group, a benzofuropyrazinyl group, a benzofuropyridazinyl group, a thienyl group, a furanyl group, a benzothiophen-yl group, a benzofuran-yl group, a dibenzothiophen-yl group, a dibenzofuran-yl group, A benzonaphthothiophen-yl group, a benzonaphthofuran-yl group, a dinaphthothiophene-yl group, a dinaphthofuran-yl group and the like can be mentioned.

[0105] In one embodiment of the present invention, the organic compound represented by the general formula (G4) is R 1 , R 2 , and R 4 thru R 21 Since at least one of the hydrogens in is replaced with deuterium, deterioration or alteration of the organic compound can be suppressed. In addition, since dissociation of carbon-hydrogen bonds in an excited state can be suppressed, it can be suitably used as a host material for dispersing a light-emitting substance of a light-emitting device.

[0106] Further, when the organic compound of one embodiment of the present invention is used as a host material in a light-emitting device, the hole-transporting skeleton may receive holes. Carbon-hydrogen bonds tend to be easily dissociated in giving and receiving holes. It is suitable because it can be prevented.

[0107] Further, in the general formulas (G1) to (G4) described in <Example of organic compound 1> to <Example of organic compound 5>, an aryl group having 6 to 100 carbon atoms or an aryl group having 2 to 100 carbon atoms Each heteroaryl group is preferably represented independently by any one of structural formulas (Ar-1) to (Ar-80).

[0108] [formation]

[0109] [formation]

[0110] [formation]

[0111] The substituents represented by the structural formulas (Ar-1) to (Ar-80) are examples of aryl groups and heteroaryl groups, and are used in the general formulas (G1) to (G4). Aryl groups and heteroaryl groups that can be used are not limited to these.

[0112] In the above general formulas (G1) to (G4), R 1 thru R 21 any one or more of is substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, substituted or unsubstituted polycyclic group having 6 to 10 carbon atoms In the case of an alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, these groups may be deuterated. It does not have to be hydrogenated.

[0113] In the above general formulas (G1) to (G4), A 1 thru A 3 at least one of the hydrogens of R, or 1 thru R 21 is deuterium, dissociation of carbon-hydrogen bonds can be prevented.

[0114] Further, in the above general formula (G4), R 1 thru R 21 are more preferably deuterium. In particular, R 1 thru R 21 is all deuterium, dissociation of all carbon-hydrogen bonds of the hole-transporting skeleton can be prevented. Even if the deuteration rate is less than 100%, the effect of preventing dissociation of carbon-hydrogen bonds can be obtained.

[0115] In this specification and the like, in the hole-transporting skeleton, that is, the benzofuropyrimidine skeleton in the general formula (G1), the deuteration rate of the benzofuropyrimidine skeleton refers to the deuteration rate of the benzofuropyrimidine skeleton. Indicates the ratio of hydrogen substituted by deuterium. For example, R 1 thru R 21 is deuterium, the deuteration rate of the benzofuropyrimidine skeleton is 100%. Also, R 1 thru R 21 is neither hydrogen nor deuterium, i.e., a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted When it is a polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the substituent has Hydrogen or deuterium shall not be used in calculating the deuteration rate of the benzofuropyrimidine skeleton.

[0116] In general formulas (G1) to (G4) above, the deuteration rate of the indolocarbazole skeleton is preferably 50% or more and 100% or less. For example, R in general formulas (G1) to (G4) 1 , even when deuterium is 50% and hydrogen is 50%, the effect of preventing the dissociation of carbon-hydrogen bonds is exhibited. R. 2 thru R 10 The same is true for The deuteration rate of the indolocarbazole skeleton is more preferably 60% or higher, preferably 70% or higher, more preferably 80% or higher, and even more preferably 90% or higher.

[0117] Further, in the above general formulas (G1) to (G4), A 1 thru A 3 at least one of the hydrogens of R, or 1 thru R 21 are more preferably deuterium. Especially R. 1 thru R 21 is deuterium, all carbon-hydrogen bonds are less likely to dissociate, which is preferable.

[0118] When the organic compound of one embodiment of the present invention having a structure represented by any of the general formulas (G1) to (G4) is used for a light-emitting device, it is preferably a thin film (also referred to as an organic compound layer). A thin film containing an organic compound that is one embodiment of the present invention can be suitably used for a light-emitting layer, a hole-transport layer, an electron-transport layer, or a cap layer in a light-emitting device. Further, the organic compound according to one embodiment of the present invention can also be used for non-light-emitting devices. Examples of non-light-emitting devices include devices such as light-receiving devices.

[0119] The structure of the case where the organic compound of one embodiment of the present invention is used for the light-emitting layer, the hole-transport layer, the electron-transport layer, or the cap layer of the light-emitting device, or the case where the organic compound is used for the light-receiving device is detailed in Embodiment 2. to explain.

[0120] <Example 1> Next, specific examples of organic compounds according to one embodiment of the present invention, which have structures represented by general formulas (G1) to (G4), are shown below. In addition, Q 1 and Q 2 is an example representing oxygen.

[0121] [formation]

[0122] [formation]

[0123] [formation]

[0124] [formation]

[0125] [formation]

[0126] [formation]

[0127] [formation]

[0128] [formation]

[0129] [formation]

[0130] [formation]

[0131] [formation]

[0132] [formation]

[0133] [formation]

[0134] [formation]

[0135] [formation]

[0136] [formation]

[0137] [formation]

[0138] [formation]

[0139] [formation]

[0140] [formation]

[0141] [formation]

[0142] [formation]

[0143] The organic compounds represented by the structural formulas (100) to (195) and the structural formulas (501) to (601) are examples of the organic compounds represented by the general formulas (G1) to (G4). , the organic compound of one embodiment of the present invention is not limited thereto.

[0144] <Example 2> Next, specific examples of organic compounds according to one embodiment of the present invention, which have structures represented by general formulas (G1) to (G4), are shown below. In addition, Q 1 and Q 2 are examples each independently representing oxygen or sulfur.

[0145] [formation]

[0146] [formation]

[0147] [formation]

[0148] [formation]

[0149] [formation]

[0150] [formation]

[0151] [formation]

[0152] [formation]

[0153] [formation]

[0154] [formation]

[0155] [formation]

[0156] [formation]

[0157] [formation]

[0158] [formation]

[0159] [formation]

[0160] [formation]

[0161] [formation]

[0162] [formation]

[0163] [formation]

[0164] [formation]

[0165] [formation]

[0166] [formation]

[0167] [formation]

[0168] [formation]

[0169] [formation]

[0170] [formation]

[0171] [formation]

[0172] The organic compounds represented by the structural formulas (201) to (337) and the structural formulas (700) to (801) are examples of the organic compounds represented by the general formulas (G1) to (G4). , the organic compound of one embodiment of the present invention is not limited thereto.

[0173] <Method for synthesizing organic compounds> In this embodiment, a method for synthesizing an organic compound represented by General Formula (G1) below will be described.

[0174] [formation]

[0175] In general formula (G1), Q 1 represents sulfur or oxygen, and R 1 thru R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polyvalent group having 6 to 10 carbon atoms represents a cyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; 1 represents an aryl group having 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group having 2 to 100 carbon atoms containing a substituted or unsubstituted substituent; 1 thru R 5 , and A 1 has at least one hydrogen replaced by deuterium.

[0176] The organic compound represented by general formula (G1) of the present invention can be synthesized according to synthesis schemes (s-1) to (s-5) shown below.

[0177] The organic compound represented by the general formula (G1) is produced by, for example, coupling a halogen compound containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton with a deuterated organoboron compound or boronic acid by Suzuki-Miyaura reaction. can be obtained. Alternatively, it can be obtained by coupling an organic boron compound or boronic acid containing a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton with a deuterated halogen compound by Suzuki-Miyaura reaction.

[0178] [formation]

[0179] [formation]

[0180] [formation]

[0181] [formation]

[0182] In the above synthesis scheme, Q 1represents sulfur or oxygen, and R 1 thru R 5 ((R n1 ) (n1 is an integer of 1 to 5) are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms , a substituted or unsubstituted C6-C10 polycyclic alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group, A. 1 represents an aryl group having 6 to 100 carbon atoms containing a substituted or unsubstituted substituent or a heteroaryl group having 2 to 100 carbon atoms containing a substituted or unsubstituted substituent; 1 thru R 5 , and A 1 has at least one hydrogen replaced by deuterium.

[0183] Also, X 1 thru X 7 (Note that X 3 thru X 6 is (X n2 ) (n2 is an integer of 3 to 6)) each independently represents a halogen or a triflate group, and X 1 thru X 7 When is halogen, chlorine, bromine and iodine are particularly preferred. However, it is not limited to X 1 thru X 7 may each independently be an organic boron group or a boronic acid. X 3 thru X 7 are each independently hydrogen or deuterium.

[0184] Palladium catalysts that can be used in the coupling reaction represented by the above synthesis scheme include palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(II) dichloride, and the like. mentioned.

[0185] Examples of ligands for the palladium catalyst include tri(ortho-tolyl)phosphine, triphenylphosphine, tricyclohexylphosphine and the like.

[0186] Examples of the base that can be used in the coupling reaction represented by the above synthetic scheme include organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate and sodium carbonate.

[0187] Solvents that can be used in the coupling reaction represented by the above synthesis scheme include a mixed solvent of toluene and water, a mixed solvent of alcohol and water such as toluene and ethanol, a mixed solvent of xylene and water, xylene and ethanol, and the like. a mixed solvent of alcohol and water, a mixed solvent of benzene and water, a mixed solvent of alcohol and water such as benzene and ethanol, and a mixed solvent of ether and water such as diethylene glycol dimethyl ether. However, solvents that can be used are not limited to these. Further, a mixed solvent of toluene and water, or a mixed solvent of toluene, ethanol and water, or a mixed solvent of ether such as diethylene glycol dimethyl ether and water is more preferable.

[0188] In addition, the reaction to be performed in the above synthesis scheme is not limited to the Suzuki-Miyaura coupling reaction, but may be the Migita-Kosugi-Stille coupling reaction using an organotin compound, the coupling reaction using a Grignard reagent, or the like. can be done.

[0189] In addition, in the above synthesis scheme (s-1), B in compound 1 1 is the A that compound 2 has 1 C 1 is the R n1 (n1 is 1 to 5) deuterium-free compound precursors. A deuteration reaction of the desired unit can give the deuteride.

[0190] Further, as a method for synthesizing the organic compound represented by general formula (G1), as shown in the following synthesis scheme (s-5), R 1 thru R 5 , and A 1 The organic compound represented by the general formula (G1) can also be obtained by deuterating the precursor of the general formula (G1) using the compound 7 containing no deuterium in any of the above. However, in this case, since it may be difficult to deuterate all hydrogen, the deuteration rate may decrease. Therefore, a synthesis method in which each partial structure is deuterated and then a coupling reaction is performed is preferable for improving the deuteration rate.

[0191] [formation]

[0192] R. 60 thru R 64 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic group having 6 to 10 carbon atoms represents an alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0193] In addition, in the above deuteration reaction, solvents that can be used include benzene-d6, toluene-d8, xylene-d10, DMSO-d6, acetonitrile-d3, heavy water, and the like. However, solvents that can be used are not limited to these.

[0194] Catalysts that can be used in the deuteration reaction include molybdenum (V) chloride, tungsten (VI) chloride, niobium (V) chloride, tantalum (V) chloride, aluminum (III) chloride, titanium (IV) chloride, ), tin (IV) chloride, and the like. However, the catalysts that can be used are not limited to these.

[0195] In addition, the above deuteration reaction may be performed after Synthesis Scheme (s-3) and Synthesis Scheme (s-4).

[0196] In the above scheme, A 1 and R 1 thru R 5 When one is the same substituent, in the synthesis scheme (s-3), by making the amount of compound 2 equivalent to compound 5, in one step, the organic compound represented by the general formula (G1) Compounds can be synthesized. Therefore, the synthesis scheme (s-4) can be omitted, making it possible to reduce the synthesis cost.

[0197] Also, R 1 thru R 5 in A 1 and R 1 thru R 5 When 2 to 4 of these have the same substituents, compound 2 is added in an amount of 3 to 5 equivalents to compound 5 in the synthesis scheme (s-3), thereby obtaining the general formula ( Organic compounds represented by G1) can be synthesized.

[0198] An example of a method for synthesizing a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, which are compounds of one embodiment of the present invention, has been described above. may be synthesized by

[0199] The structure described in this embodiment can be combined as appropriate with any of the structures described in other embodiments.

[0200] (Embodiment 2) In this embodiment, a structure of a light-emitting device using the organic compound described in Embodiment 1 will be described with reference to FIGS. 1(A) to 1(E).

[0201] <<Basic Structure of Light-Emitting Device>> A basic structure of a light-emitting device will be described. FIG. 1A shows a light-emitting device having an EL layer including a light-emitting layer between a pair of electrodes. Specifically, it has a structure in which the EL layer 103 is sandwiched between the first electrode 101 and the second electrode 102 .

[0202] Further, in FIG. 1(B), a plurality of EL layers (103a and 103b) (two layers in FIG. 1(B)) are provided between a pair of electrodes, and a charge generation layer 106 is provided between the EL layers. A light-emitting device with a laminated structure (tandem structure) is shown. A light-emitting device with a tandem structure can realize a highly efficient light-emitting device without changing the amount of current.

[0203] When a potential difference is generated between the first electrode 101 and the second electrode 102, the charge generation layer 106 injects electrons into one EL layer (103a or 103b) and injects electrons into the other EL layer (103b or It has a function of injecting holes into 103a). Therefore, in FIG. 1(B), when a voltage is applied to the first electrode 101 so that the potential is higher than that of the second electrode 102, electrons are injected from the charge generation layer 106 into the EL layer 103a. Holes are injected into 103b.

[0204] From the viewpoint of light extraction efficiency, the charge generation layer 106 may be transparent to visible light (specifically, the charge generation layer 106 has a visible light transmittance of 40% or more). preferable. Also, the charge generation layer 106 functions even with a lower conductivity than the first electrode 101 and the second electrode 102 .

[0205] Further, FIG. 1C shows a stacked structure of the EL layer 103 of the light-emitting device which is one embodiment of the present invention. However, in this case, the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked on the first electrode 101. have Note that the light-emitting layer 113 may have a structure in which a plurality of light-emitting layers emitting light of different colors are stacked. For example, a light-emitting layer containing a light-emitting substance that emits red light, a light-emitting layer that contains a light-emitting substance that emits green light, and a light-emitting layer that contains a light-emitting substance that emits blue light are stacked, or a layer containing a carrier-transporting material is interposed therebetween. It may be a structure in which the layers are laminated together. Alternatively, a light-emitting layer containing a light-emitting substance that emits yellow light and a light-emitting layer containing a light-emitting substance that emits blue light may be combined. However, the laminated structure of the light-emitting layer 113 is not limited to the above. For example, the light-emitting layer 113 may have a structure in which a plurality of light-emitting layers emitting the same color are stacked. For example, a structure in which a first light-emitting layer containing a light-emitting substance that emits blue light and a second light-emitting layer that contains a light-emitting substance that emits blue light are laminated, or a layer containing a carrier-transporting material is interposed therebetween. It can be. In the case of a structure in which a plurality of light-emitting layers emitting light of the same color are stacked, reliability may be improved as compared with a single-layer structure. Even in the case of having a plurality of EL layers like the tandem structure shown in FIG. 1(B), the EL layers are stacked sequentially from the anode side as described above. Also, when the first electrode 101 is the cathode and the second electrode 102 is the anode, the stacking order of the EL layers 103 is reversed. Specifically, 111 on the first electrode 101, which is a cathode, is an electron injection layer, 112 is an electron transport layer, 113 is a light emitting layer, 114 is a hole transport layer, and 115 is a hole transport layer. It has a configuration of an injection layer.

[0206] The light-emitting layers 113 included in the EL layers (103, 103a, 103b) each have a light-emitting substance and a plurality of substances in appropriate combination, and are configured to obtain fluorescence or phosphorescence with a desired emission color. can be In addition, the light-emitting layer 113 may have a laminated structure that emits light of different colors. Note that in this case, different materials may be used for the light-emitting substance and the other substance used in each of the stacked light-emitting layers. Further, a configuration in which different emission colors are obtained from the plurality of EL layers (103a and 103b) shown in FIG. 1(B) may be employed. In this case also, different materials may be used for the light-emitting substance and other substances used in each light-emitting layer.

[0207] Further, in the light-emitting device which is one embodiment of the present invention, for example, the first electrode 101 shown in FIG. With the (microcavity) structure, light emitted from the light-emitting layer 113 included in the EL layer 103 can be resonated between both electrodes, and light emitted from the second electrode 102 can be enhanced.

[0208] Note that when the first electrode 101 of the light-emitting device is a reflective electrode having a laminated structure of a reflective conductive material and a translucent conductive material (transparent conductive film), the film of the transparent conductive film Optical tuning can be achieved by controlling the thickness. Specifically, the optical distance between the first electrode 101 and the second electrode 102 (the product of the film thickness and the refractive index) is mλ / It is preferable to adjust to 2 (where m is an integer equal to or greater than 1) or its vicinity.

[0209] In order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical distance from the first electrode 101 to the region (light-emitting region) of the light-emitting layer 113 from which the desired light is obtained, (2m′+1)λ / 4 (where m′ is an integer equal to or greater than 1) or It is preferable to adjust them so that they are close to each other. The light-emitting region here means a recombination region of holes and electrons in the light-emitting layer 113 .

[0210] By performing such optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.

[0211] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is the total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102. can. However, since it is difficult to strictly determine the reflective regions in the first electrode 101 and the second electrode 102, it is possible to assume arbitrary positions of the first electrode 101 and the second electrode 102 as the reflective regions. can sufficiently obtain the above effects. Strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer from which desired light is obtained is the optical distance between the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light is obtained. It can be said that it is the distance. However, since it is difficult to strictly determine the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer from which desired light is obtained, an arbitrary position of the first electrode 101 can be set as the reflective region and the desired light. By assuming that an arbitrary position of the light-emitting layer from which light is obtained is the light-emitting region, the above effects can be sufficiently obtained.

[0212] The light-emitting device shown in FIG. 1(D) is a light-emitting device having a tandem structure, and since it has a microcavity structure, light of different wavelengths (monochromatic light) can be extracted from each EL layer (103a, 103b). . Therefore, separate coloring (for example, RGB) for obtaining different emission colors is unnecessary. Therefore, it is easy to achieve high definition. A combination with a colored layer (color filter) is also possible. Furthermore, since it is possible to increase the emission intensity of the specific wavelength in the front direction, it is possible to reduce power consumption.

[0213] The light-emitting device shown in FIG. 1(E) is an example of the tandem structure light-emitting device shown in FIG. It has a laminated structure with (106a, 106b) sandwiched therebetween. The three EL layers (103a, 103b, 103c) each have a luminescent layer (113a, 113b, 113c), and the luminescent colors of the respective luminescent layers can be freely combined. For example, light-emitting layer 113a can be blue, light-emitting layer 113b can be either red, green, or yellow, and light-emitting layer 113c can be blue; Alternatively, the light-emitting layer 113c can be red.

[0214] Note that in the above-described light-emitting device which is one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (a transparent electrode, a semi-transmissive / semi-reflective electrode, or the like). do. When the electrode having translucency is a transparent electrode, the visible light transmittance of the transparent electrode is set to 40% or more. In the case of the semi-transmissive / semi-reflective electrode, the visible light reflectance of the semi-transmissive / semi-reflective electrode should be 20% or more and 80% or less, preferably 40% or more and 70% or less. These electrodes also have a resistivity of 1×10 -2 Ωcm or less is preferable.

[0215] Further, in the above-described light-emitting device according to one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode is visible. The light reflectance is 40% or more and 100% or less, preferably 70% or more and 100% or less. Also, this electrode has a resistivity of 1×10 -2 Ωcm or less is preferable.

[0216] <<Specific structure of light-emitting device>> Next, a specific structure of a light-emitting device that is one embodiment of the present invention is described. Also, here, description is made using FIG. 1(D) having a tandem structure. Note that the structure of the EL layer is the same for the single-structure light-emitting devices shown in FIGS. 1(A) and 1(C). When the light-emitting device shown in FIG. 1D has a microcavity structure, the first electrode 101 is formed as a reflective electrode, and the second electrode 102 is formed as a semi-transmissive / semi-reflective electrode. Therefore, a desired electrode material can be used singly or plurally to form a single layer or lamination. Note that the second electrode 102 is formed by selecting an appropriate material after the EL layer 103b is formed.

[0217] <First electrode and second electrode> As materials for forming the first electrode 101 and the second electrode 102, the following materials can be used in appropriate combination as long as the above-described functions of both electrodes can be satisfied. For example, metals, alloys, electrically conductive compounds, mixtures thereof, and the like can be used as appropriate. Specifically, In--Sn oxide (also referred to as ITO), In--Si--Sn oxide (also referred to as ITSO), In--Zn oxide, and In--W--Zn oxide can be mentioned. In addition, aluminum (Al), magnesium (Mg), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga) ), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag ), yttrium (Y), neodymium (Nd), and alloys containing appropriate combinations thereof can also be used. In addition, elements belonging to group 1 or 2 of the periodic table of elements not exemplified above (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium Rare earth metals such as (Yb), alloys containing an appropriate combination thereof, graphene, and the like can be used.

[0218] In the light-emitting device shown in FIG. 1(D), when the first electrode 101 is an anode, the hole-injection layer 111a and the hole-transport layer 112a of the EL layer 103a are sequentially formed on the first electrode 101 by a vacuum evaporation method. It is laminated. After EL layer 103a and charge generation layer 106 are formed, hole injection layer 111b and hole transport layer 112b of EL layer 103b are sequentially laminated on charge generation layer 106 in the same manner.

[0219] <Hole injection layer> The hole injection layers (111, 111a, 111b) inject holes from the first electrode 101, which is an anode, and the charge generation layers (106, 106a, 106b) into the EL layers (103, 103a, 103b). It is a layer containing an organic acceptor material and a material with a high hole injection property.

[0220] An organic acceptor material is a material that can generate holes in an organic compound by causing charge separation between the organic compound whose LUMO level value and HOMO level value are close to each other. be. Accordingly, compounds having electron-withdrawing groups (halogen groups or cyano groups) such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used as organic acceptor materials. For example, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), 3,6-difluoro-2,5,7,7,8,8-hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8 ,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), 2-(7- Dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyren-2-ylidene)malononitrile and the like can be used. Among organic acceptor materials, a compound in which an electron-withdrawing group is bound to a condensed aromatic ring having multiple heteroatoms, such as HAT-CN, is suitable because it has high acceptor properties and stable film quality against heat. is. In addition, [3]radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) are preferred because of their extremely high electron-accepting properties, specifically α, α', α'. '-1,2,3-Cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriy Redentris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidentris[2,3 ,4,5,6-pentafluorobenzeneacetonitrile] and the like can be used.

[0221] Materials with high hole injection properties include oxides of metals belonging to groups 4 to 8 in the periodic table (molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc.). transition metal oxides, etc.) can be used. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among the above, molybdenum oxide is preferred because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle. In addition, phthalocyanine (abbreviation: H 2 Pc) or a phthalocyanine-based compound such as copper phthalocyanine (abbreviation: CuPc) can be used.

[0222] In addition to the above materials, low-molecular compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris [N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 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), Aromatic amine compounds such as 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and the like can be used.

[0223] In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4 -{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)- N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) and the like can be used. Alternatively, poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviation: PEDOT / PSS), polyaniline / polystyrene sulfonic acid (abbreviation: PAni / PSS), etc. can also be used.

[0224] As a material with high hole injection properties, a mixed material containing a hole transporting material and the organic acceptor material (electron accepting material) described above can also be used. In this case, electrons are extracted from the hole-transporting material by the organic acceptor material, holes are generated in the hole-injection layer 111 , and holes are injected into the light-emitting layer 113 via the hole-transporting layer 112 . Note that the hole injection layer 111 may be formed of a single layer made of a mixed material containing a hole-transporting material and an organic acceptor material (electron-accepting material). (electron-accepting material) may be laminated in separate layers.

[0225] The hole transport material has a hole mobility of 1 × 10 when the square root of the electric field strength [V / cm] is 600. -6 cm 2 A material having a hole mobility of / Vs or more is preferred. Note that any substance other than these can be used as long as it has a higher hole-transport property than electron-transport property.

[0226] Examples of hole-transporting materials include compounds having a π-electron-rich heteroaromatic ring (e.g., carbazole derivatives, furan derivatives, or thiophene derivatives), and positive compounds such as aromatic amines (organic compounds having an aromatic amine skeleton). Materials with high pore transport properties are preferred. Since the compound of Embodiment 1 has a hole-transport property, it can also be used as a hole-transport material.

[0227] Examples of the carbazole derivatives (organic compounds having a carbazole ring) include bicarbazole derivatives (eg, 3,3'-bicarbazole derivatives) and aromatic amines having a carbazolyl group.

[0228] Further, specific examples of the bicarbazole derivative (for example, 3,3′-bicarbazole derivative) include 3,3′-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9 '-Bis(biphenyl-4-yl)-3,3'-bi-9H-carbazole (abbreviation: BisBPCz), 9,9'-bis(1,1'-biphenyl-3-yl)-3,3' -Bi-9H-carbazole (abbreviation: BismBPCz), 9-(1,1'-biphenyl-3-yl)-9'-(1,1'-biphenyl-4-yl)-9H,9'H-3 ,3'-bicarbazole (abbreviation: mBPCCBP), 9-(2-naphthyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: βNCCP), and the like.

[0229] Further, specific examples of the aromatic amine having a carbazolyl group include 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), N-( 4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl- 4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), N-[4- (9-phenyl-9H-carbazol-3-yl)phenyl]-bis(9,9-dimethyl-9H-fluoren-2-yl)amine (abbreviation: PCBFF), N-(1,1'-biphenyl-4 -yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-4-amine, N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-4-amine, N-(1,1'-biphenyl- 4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-diphenyl-9H-fluoren-2-amine, N-(1,1'-biphenyl- 4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-diphenyl-9H-fluoren-4-amine, N-(1,1'-biphenyl- 4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi(9H-fluorene)-2-amine, N-(1,1'- biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi(9H-fluorene)-4-amine, N-[4-( 9-Phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':3',1''-terphenyl-4-yl)-9,9-dimethyl-9H-fluorene-2- Amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':4',1''-terphenyl-4-yl)-9,9- Dimethyl-9H-fluoren-2-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':3',1''-terphenyl-4 -yl)-9,9-dimethyl-9H-fluoren-4-amine, N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-N-(1,1':4', 1''-terphenyl-4-yl)-9,9-dimethyl-9H-fluoren-4-amine, 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl) Triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1 -naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine ( Abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''- Triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N- [4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl) )Phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 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: PCzPCN1), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl) -N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-bis[4-(carbazole- 9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F), 4,4',4''-tris(carbazol-9-yl)tri Examples include phenylamine (abbreviation: TCTA).

[0230] As carbazole derivatives, in addition to the above, 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3-[4-(1-naphthyl)- Phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP) , 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9 -[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA) and the like.

[0231] Further, as the furan derivative (an organic compound having a furan ring), specifically, 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P- II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), and the like.

[0232] Further, as the thiophene derivative (organic compound having a thiophene ring), specifically, 4,4′,4″-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P -II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl- 9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and the like.

[0233] Further, as the aromatic amine, specifically, 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), 4,4'-bis[N-(spiro-9, 9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4- Phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-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), N-(9 ,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'- Bifluorene (abbreviation: DPASF), 2,7-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-spiro-9,9'-bifluorene (abbreviation: DPA2SF), 4,4',4' '-Tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-MTDATA), N,N'-di(p -tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), N-(4-biphenyl)-6,N-diphenylbenzo[b]naphtho [1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ( BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)-4''-phenyltriphenylamine (abbreviation: BnfBB1BP), N, N-bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[ 1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf(II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophene- 4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1BP), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: BBAβNB), 4-[4 -(2-naphthyl)phenyl]-4',4''-diphenyltriphenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1'-binaphthyl-2-yl)tri Phenylamine (abbreviation: BBAαNβNB), 4,4'-diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4 ''-(7-Phenyl)naphthyl-2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl-4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B), 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(βN2)B-03), 4, 4'-diphenyl-4''-(4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-(5;2'-binaphthyl-1 -yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3- Biphenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-(2-naphthyl) Phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβNBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA1BP), 4,4'-bis(1-naphthyl)tri Phenylamine (abbreviation: αNBB1BP), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4 -(3-Phenyl-9H-carbazol-9-yl)phenyl]tris(1,1'-biphenyl-4-yl)amine (abbreviation: YGTBi1BP-02), 4-[4'-(carbazol-9-yl) )biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenylamine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl ]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'-biphenyl] -4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9 '-spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1'-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluorene-2 -yl)-9,9'-spirobi[9H-fluoren]-4-amine (abbreviation: oFBiSF), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl) Dibenzofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN) , 4-phenyl-4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation: BPAFLBi), N,N-bis(9,9-dimethyl-9H-fluorene-2- yl)-9,9'-spirobi-9H-fluoren-4-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluorene- 3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-2-amine, N,N-bis(9,9- dimethyl-9H-fluoren-2-yl)-9,9'-spirobi-9H-fluoren-1-amine, and the like.

[0234] In addition, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVK), which are high molecular compounds (oligomers, dendrimers, polymers, etc.), are used as hole-transporting materials. PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N' -Bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) and the like can be used. Alternatively, poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (abbreviation: PEDOT / PSS), polyaniline / polystyrene sulfonic acid (abbreviation: PAni / PSS), etc. can also be used.

[0235] However, the hole-transporting material is not limited to the above, and one or a combination of various known materials may be used as the hole-transporting material.

[0236] The hole injection layers (111, 111a, 111b) can be formed using various known film forming methods, and for example, can be formed using a vacuum deposition method.

[0237] <Hole transport layer> The hole transport layers (112, 112a, 112b) transport holes injected from the first electrode 101 by the hole injection layers (111, 111a, 111b) to the light emitting layers (113, 113a, 113b). layer. The hole-transporting layers (112, 112a, 112b) are layers containing a hole-transporting material. Therefore, for the hole transport layers (112, 112a, 112b), a hole transport material that can be used for the hole injection layers (111, 111a, 111b) can be used.

[0238] Note that in the light-emitting device which is one embodiment of the present invention, the same organic compound as the hole-transporting layers (112, 112a, 112b) can be used for the light-emitting layers (113, 113a, 113b). When the same organic compound is used for the hole transport layers (112, 112a, 112b) and the light emitting layers (113, 113a, 113b), the hole transport layers (112, 112a, 112b) to the light emitting layers (113, 113a, 113b) It is more preferable because the holes can be transported efficiently.

[0239] <Light emitting layer> The light-emitting layers (113, 113a, 113b) are layers containing light-emitting substances. As a light-emitting substance that can be used for the light-emitting layers (113, 113a, 113b), a substance that emits light of blue, purple, blue-violet, green, yellow-green, yellow, orange, red, or the like can be used as appropriate. can. In the case where a plurality of light-emitting layers are provided, a structure in which different light-emitting substances are used for each light-emitting layer to exhibit different emission colors (for example, white light emission obtained by combining complementary emission colors) can be employed. can. Furthermore, a laminated structure in which one light-emitting layer contains different light-emitting substances may be employed.

[0240] In addition, the light-emitting layers (113, 113a, 113b) may contain one or more organic compounds (host material, etc.) in addition to the light-emitting substance (guest material).

[0241] When a plurality of host materials are used for the light-emitting layers (113, 113a, 113b), a substance having an energy gap larger than that of the existing guest materials and the first host material is used as the newly added second host material. is preferably used. The lowest singlet excitation level (S1 level) of the second host material is higher than the S1 level of the first host material, and the lowest triplet excitation level (T1 level) of the second host material is higher than that of the first host material. ) is preferably higher than the T1 level of the guest material. Also, the lowest triplet excitation level (T1 level) of the second host material is preferably higher than the T1 level of the first host material. With such a structure, an exciplex can be formed with two types of host materials. Note that in order to efficiently form an exciplex, it is particularly preferable to combine a compound that easily accepts holes (hole-transporting material) and a compound that readily accepts electrons (electron-transporting material). Also, with this configuration, high efficiency, low voltage, and long life can be achieved at the same time.

[0242] The organic compound used as the above host material (including the first host material and the second host material) may be selected from the above-described hole transport layer (112, 112a, 112b), or an electron-transporting material that can be used in the later-described electron-transporting layers (114, 114a, 114b). It may be an exciplex composed of compounds (the first host material and the second host material described above). Exciplexes (also called exciplexes, exciplexes, or exciplexes) that form an excited state with multiple types of organic compounds have an extremely small difference between the S1 level and the T1 level, and the triplet excitation energy is reduced to the singlet excitation energy. It functions as a TADF material that can be converted into energy. As a combination of a plurality of types of organic compounds that form an exciplex, for example, it is preferable that one has a π-electron-deficient heteroaromatic ring and the other has a π-electron-rich heteroaromatic ring. Note that as a combination forming an exciplex, an organometallic complex based on iridium, rhodium, or platinum, or a phosphorescent substance such as a metal complex may be used for one side. The organic compound described in Embodiment 1 can be effectively used as the first host material because it has an electron-transport property. In addition, since it has a hole-transport property, it can be used as a second host material.

[0243] The light-emitting substance that can be used in the light-emitting layers (113, 113a, 113b) is not particularly limited. Altering luminescent materials can be used.

[0244] ≪Luminescent substances that convert singlet excitation energy into luminescence≫ Examples of light-emitting substances that convert singlet excitation energy into light emission that can be used in the light-emitting layers (113, 113a, 113b) include the following substances that emit fluorescence (fluorescent light-emitting substances). Examples include pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives and the like. Pyrene derivatives are particularly preferred because they have a high emission quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6 -diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: : 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene -2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b) ]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[ 1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho [1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03) and the like.

[0245] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9- anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), 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-(9H- Carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl) Phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCAPA) PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), perylene, 2,5 ,8,11-tetra-tert-butylperylene (abbreviation: TBP), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N', N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole-3- Amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), etc. can be used.

[0246] In addition, 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), 9,10-bis(1,1'-biphenyl-2-yl) -N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA) , coumarin 545T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT), 2 -(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl-6-[ 2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N ,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methyl Phenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1,7,7-tetramethyl-2 2-{2-tert- Butyl-6-[2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidin-9-yl)ethenyl]-4H-pyran- 4-ylidene}propanedinitrile (abbreviation: DCJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl}-4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCJTB) BisDCM), 2-{2,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine- 9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), 1,6BnfAPrn-03, 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl )-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-02), 3,10-bis[N-(dibenzofuran-3- yl)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10FrA2Nbf(IV)-02) and the like. In particular, pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, 1,6BnfAPrn-03, and the like can be used.

[0247] ≪Luminescent substances that convert triplet excitation energy into luminescence≫ Next, the light-emitting substance that converts triplet excitation energy into light emission that can be used in the light-emitting layer 113 includes, for example, a substance that emits phosphorescence (phosphorescent light-emitting substance), or a thermally activated delayed fluorescence that exhibits thermally activated delayed fluorescence. (Thermally activated delayed fluorescence: TADF) materials.

[0248] A phosphorescent substance refers to a compound that exhibits phosphorescence and does not exhibit fluorescence in a temperature range from low temperature (for example, 77 K) to room temperature (that is, from 77 K to 313 K). The phosphorescent substance preferably contains a metal element having a large spin-orbit interaction, and examples thereof include organometallic complexes, metal complexes (platinum complexes), rare earth metal complexes, and the like. Specifically, a transition metal element is preferable, and in particular, it may contain a platinum group element (ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), or platinum (Pt)). Among them, iridium is preferable because the transition probability associated with the direct transition between the singlet ground state and the triplet excited state can be increased.

[0249] ≪Phosphorescent substance (450 nm or more and 570 nm or less: blue or green)≫ Examples of phosphorescent substances that exhibit blue or green color and have an emission spectrum with a peak wavelength of 450 nm or more and 570 nm or less include the following substances.

[0250] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III ) (abbreviation: [Ir(mpptz-dmp) 3 ]), tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)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 ]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz) 3 ]), an organometallic complex having a 4H-triazole ring, such as tris[3-methyl-1-(2-methylphenyl)-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 ]), fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi) 3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me) 3 ]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (FIr6) , bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl) Phenyl]pyridinato-N,C 2’} Iridium (III) picolinate (abbreviation: [Ir(CF 3 ppy) 2 (pic)]), bis[2-(4’,6’-difluorophenyl)pyridinato-N,C 2’ ] iridium (III) acetylacetonate (abbreviation: FIr(acac)) and other organometallic complexes having a phenylpyridine derivative having an electron-withdrawing group as a ligand.

[0251] ≪Phosphorescent substance (495 nm or more and 590 nm or less: green or yellow)≫ Examples of the phosphorescent substance that exhibits green or yellow color and has an emission spectrum with a peak wavelength of 495 nm or more and 590 nm or less include the following substances.

[0252] For example, 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-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm) 2 (acac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm) 2 (acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm) 2 (acac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN]phenyl-κC}iridium(III) (abbreviation: [Ir(dmppm-dmp) 2 (acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) 2 (acac)]), (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me ) 2 (acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr) 2 Organometallic iridium complexes with pyrazine rings such as (acac)]), tris(2-phenylpyridinato-N,C 2’ ) iridium (III) (abbreviation: [Ir(ppy) 3]), bis(2-phenylpyridinato-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 (abbreviation: [Ir(pq) 2 (acac)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir(ppy ) 2 (4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC], [2-d3-methyl -8-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3-methyl-2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(5mppy-d3) 2 (mbfpypy-d3)), [2-(methyl-d3)-8-[4-(1-methylethyl-1-d)-2-pyridinyl-κN]benzofuro[2,3-b]pyridine-7- yl-κC]bis[5-(methyl-d3)-2-[5-(methyl-d3)-2-pyridinyl-κN]phenyl-κC]iridium(III) (abbreviation: Ir(5mtpy-d6) 2 (mbfpypy-iPr-d4)), [2-d3-methyl-(2-pyridinyl-κN)benzofuro[2,3-b]pyridine-κC] bis[2-(2-pyridinyl-κN)phenyl-κC] Iridium(III) (abbreviation: Ir(ppy) 2 (mbfpypy-d3)), [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation :Ir(ppy) 2 Organometallic iridium complexes with pyridine rings such as (mdppy)), bis(2,4-diphenyl-1,3-oxazolato-N,C) 2’ ) iridium (III) acetylacetonate (abbreviation: [Ir(dpo) 2 (acac)]), bis{2-[4’-(perfluorophenyl)phenyl]pyridinato-N,C 2’} Iridium (III) acetylacetonate (abbreviation: [Ir(p-PF-ph) 2 (acac)]), bis(2-phenylbenzothiazolato-N,C 2’ ) iridium (III) acetylacetonate (abbreviation: [Ir(bt) 2 (acac)]), tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)) 3 (Phen)]).

[0253] ≪Phosphorescent substance (570 nm or more and 750 nm or less: yellow or red)≫ Examples of phosphorescent substances that exhibit yellow or red color and have an emission spectrum with a peak wavelength of 570 nm or more and 750 nm or less include the following substances.

[0254] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm) 2 (dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm) 2 (dpm)]), (dipivaloylmethanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm) 2 (dpm)]), (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr) 2 (acac)]), bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr) 2 (dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3 ,5-Heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-P) 2 (dibm)]), bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl -κC}(2,2,6,6-tetramethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2 (dpm)]), bis[2-(5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN)-4,6-dimethylphenyl-κC]( 2,2',6,6'-tetramethyl-3,5-heptanedionato-κO,O')iridium(III) (abbreviation: [Ir(dmdppr-dmp) 2 (dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalinato-N,C 2’ ]iridium(III) (abbreviation: [Ir(mpq) 2 (acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ ) Iridium (III) (abbreviation: [Ir(dpq) 2 (acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq) 2 (acac)]), an organometallic complex with a pyrazine ring, tris(1-phenylisoquinolinato-N,C) 2’ ) iridium (III) (abbreviation: [Ir(piq) 3 ]), bis(1-phenylisoquinolinato-N,C 2’ ) iridium (III) acetylacetonate (abbreviation: [Ir(piq) 2 (acac)]), and bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O,O’)iridium(III) (abbreviation: [Ir(dmpqn) 2 (acac)]), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: [PtOEP]) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM) 3 (Phen)]), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline) europium(III) (abbreviation: [Eu(TTA) 3 (Phen)]).

[0255] ≪TADF material≫ As the TADF material, the following materials can be used. A TADF material has a small difference between the S1 level and the T1 level (preferably, 0.2 eV or less), and the triplet excited state is up-converted (reverse intersystem crossing) to the singlet excited state by a small amount of thermal energy. It is a material that efficiently emits light (fluorescence) from a singlet excited state. In addition, as a condition for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. . In addition, delayed fluorescence in the TADF material refers to luminescence having a spectrum similar to that of normal fluorescence and having a significantly long lifetime. Its lifetime is 1×10 -6 seconds or more, or 1 x 10 -3 seconds or more. Further, the organic compounds described in Embodiment 1 can be used.

[0256] The TADF material can also be used as an electron-transporting material, a hole-transporting material, and a host material.

[0257] TADF materials include, for example, fullerenes and derivatives thereof, acridine derivatives such as proflavin, and eosin. Also included are metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include protoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Proto IX)), mesoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Meso IX)), hematoporphyrin-tin fluoride complex (abbreviation: SnF 2 (Hemato IX)), coproporphyrin tetramethyl ester-stannous fluoride complex (abbreviation: SnF 2 (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF) 2 (OEP)), Ethioporphyrin-tin fluoride complex (abbreviation: SnF 2 (Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl 2OEP), etc.

[0258] [formation]

[0259] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC -TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4- (5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H) -acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9'-anthracen]-10'-one (abbreviation: ACRSA), 4-(9'-phenyl-3,3'-bi-9H-carbazole -9-yl)benzofuro[3,2-d]pyrimidine (abbreviation: 4PCCzBfpm), 4-[4-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)phenyl]benzofuro[ 3,2-d]pyrimidine (abbreviation: 4PCCzPBfpm), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'- Heteroaromatic compounds having π-electron-rich heteroaromatic compounds and π-electron-deficient heteroaromatic compounds such as bi-9H-carbazole (abbreviation: mPCCzPTzn-02) may also be used.

[0260] A substance in which a π-electron-rich heteroaromatic compound and a π-electron-deficient heteroaromatic compound are directly bonded has the donor property of the π-electron-rich heteroaromatic compound and the acceptor property of the π-electron-deficient heteroaromatic compound. becomes strong, and the energy difference between the singlet excited state and the triplet excited state becomes small, which is particularly preferable. As the TADF material, a TADF material (TADF100) in which a singlet excited state and a triplet excited state are in thermal equilibrium may be used. Since such a TADF material has a short emission lifetime (excitation lifetime), it is possible to suppress a decrease in efficiency in a high-luminance region of a light-emitting device.

[0261] [formation]

[0262] In addition to the above, examples of materials having a function of converting triplet excitation energy into light emission include nanostructures of transition metal compounds having a perovskite structure. Nanostructures of metal halide perovskites are particularly preferred. Nanoparticles and nanorods are preferred as the nanostructures.

[0263] In the light-emitting layers (113, 113a, 113b, 113c), the organic compound (host material, etc.) used in combination with the above-described light-emitting substance (guest material) has an energy gap larger than that of the light-emitting substance (guest material). One or a plurality of substances may be selected and used.

[0264] <<Host material for fluorescence emission>> When the light-emitting substance used in the light-emitting layers (113, 113a, 113b, 113c) is a fluorescent light-emitting substance, the combined organic compound (host material) has a large singlet excited state energy level and a triplet excited state energy level. It is preferable to use an organic compound with a small order or an organic compound with a high fluorescence quantum yield. Therefore, a hole-transporting material (described above), an electron-transporting material (described later), and the like described in this embodiment can be used as long as they are organic compounds satisfying such conditions. Further, the organic compounds described in Embodiment 1 can be used.

[0265] Although partly overlapping with the above-described specific examples, from the viewpoint of a preferable combination with a light-emitting substance (fluorescent light-emitting substance), organic compounds (host materials) include anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, Examples include condensed polycyclic aromatic compounds such as dibenzo[g,p]chrysene derivatives.

[0266] A specific example of an organic compound (host material) that is preferably used in combination with a fluorescent substance is 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation : PCzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 3-[4-(1-naphthyl)-phenyl]- 9-phenyl-9H-carbazole (abbreviation: PCPN), 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H- Carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-( 10-Phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole- 3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylchrysene, N,N,N',N',N'',N'',N''',N'''- Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (DBC1), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (CzPA) , 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl ]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)-biphenyl-4'-yl}-anthracene (abbreviation: FLPPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert- Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9-(1-naphthyl)-10-(2-naphthyl)anthracene (abbreviation: α,β-ADN), 2-( 10-phenylanthracen-9-yl)dibenzofuran, 2-(10-phenyl-9-anthracenyl)-benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA), 9-(1 -naphthyl)-10-[4-(2-naphthyl)phenyl]anthracene (abbreviation: αN-βNPAnth), 2,9-di(1-naphthyl)-10-phenylanthracene (abbreviation: 2αN-αNPhA), 9- (1-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: αN-mαNPAnth), 9-(2-naphthyl)-10-[3-(1-naphthyl)phenyl]anthracene (abbreviation: αN-mαNPAnth) : βN-mαNPAnth), 9-(1-naphthyl)-10-[4-(1-naphthyl)phenyl]anthracene (abbreviation: αN-αNPAnth), 9-(2-naphthyl)-10-[4-(2 -naphthyl)phenyl]anthracene (abbreviation: βN-βNPAnth), 2-(1-naphthyl)-9-(2-naphthyl)-10-phenylanthracene (abbreviation: 2αN-βNPhA), 9-(2-naphthyl)- 10-[3-(2-naphthyl)phenyl]anthracene (abbreviation: βN-mβNPAnth), 1-[4-(10-[1,1'-biphenyl]-4-yl-9-anthracenyl)phenyl]-2 -ethyl-1H-benzimidazole (abbreviation: EtBImPBPhA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9, 9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), 5,12-diphenyltetracene, 5,12 -bis(biphenyl-2-yl)tetracene and the like.

[0267] <<Host material for phosphorescence>> When the light-emitting substance used in the light-emitting layers (113, 113a, 113b, 113c) is a phosphorescent light-emitting substance, the organic compound (host material) to be combined with the triplet excitation energy (ground state and triplet excited state) of the light-emitting substance It suffices to select an organic compound having a triplet excitation energy larger than the energy difference between ). Note that when a plurality of organic compounds (for example, a first host material, a second host material (or an assist material), etc.) are used in combination with a light-emitting substance to form an exciplex, these plurality of organic compounds is preferably mixed with a phosphorescent material. Further, the organic compounds described in Embodiment 1 can be used.

[0268] With such a structure, light emission using ExTET (Exciplex-Triplet Energy Transfer), which is energy transfer from an exciplex to a light-emitting substance, can be efficiently obtained. As a combination of a plurality of organic compounds, one that easily forms an exciplex is preferable, and a compound that easily accepts holes (hole-transporting material) and a compound that easily accepts electrons (electron-transporting material) are combined. is particularly preferred.

[0269] Although partly overlaps with the above-described specific examples, from the viewpoint of a preferable combination with a light-emitting substance (phosphorescent substance), as an organic compound (host material, assist material), an aromatic amine (having an aromatic amine skeleton) organic compounds), carbazole derivatives (organic compounds having a carbazole ring), dibenzothiophene derivatives (organic compounds having a dibenzothiophene ring), dibenzofuran derivatives (organic compounds having a dibenzofuran ring), oxadiazole derivatives (having an oxadiazole ring) organic compounds), triazole derivatives (organic compounds having a triazole ring), benzimidazole derivatives (organic compounds having a benzimidazole ring), quinoxaline derivatives (organic compounds having a quinoxaline ring), dibenzoquinoxaline derivatives (organic compounds having a dibenzoquinoxaline ring) ), pyrimidine derivatives (organic compounds having a pyrimidine ring), triazine derivatives (organic compounds having a triazine ring), pyridine derivatives (organic compounds having a pyridine ring), bipyridine derivatives (organic compounds having a bipyridine ring), phenanthroline derivatives (phenanthroline organic compounds having a phodiazine ring), flodiazine derivatives (organic compounds having a phodiazine ring), zinc- and aluminum-based metal complexes, and the like.

[0270] Among the above organic compounds, specific examples of aromatic amines and carbazole derivatives, which are highly hole-transporting organic compounds, include the same specific examples as the hole-transporting materials described above. All of these are preferable as host materials.

[0271] Among the above organic compounds, specific examples of dibenzothiophene derivatives and dibenzofuran derivatives, which are highly hole-transporting organic compounds, include 4-{3-[3-(9-phenyl-9H-fluorene- 9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 4 ,4',4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H- Fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) ), 4-[3-(triphenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mDBTPTp-II), and the like, all of which are preferable as host materials.

[0272] Other oxazoles such as bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ) , a metal complex having a thiazole-based ligand, and the like are also mentioned as preferred host materials.

[0273] Further, among the above organic compounds, specific examples of oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, quinazoline derivatives, phenanthroline derivatives, etc., which are highly electron-transporting organic compounds, include: 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), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl] -9H-carbazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2' ,2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1 -Phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), including heteroaromatic rings with polyazole rings Organic compounds such as bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), etc. Organic compounds containing a heteroaromatic ring with a pyridine ring, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzo Thiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[ f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 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] Quinoxaline (abbreviation: 6mDBTPDBq-II), 2-{4-[9,10-di(2-naphthyl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN), 2-[ 4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mpPCBPDBq), etc., all of which are It is preferable as a host material.

[0274] Among the above organic compounds, specific examples of pyridine derivatives, diazine derivatives (including pyrimidine derivatives, pyrazine derivatives, and pyridazine derivatives), triazine derivatives, and phlodiazine derivatives, which are highly electron-transporting organic compounds, include 4,6 -bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)- 9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazine- 2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), 9,9'-[pyrimidine-4,6-diylbis(biphenyl-3,3' -diyl)]bis(9H-carbazole) (abbreviation: 4,6mCzBP2Pm), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3-yl ]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 8-(1,1'-biphenyl-4-yl)-4-[3-(dibenzothiophen-4-yl)phenyl ]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8BP-4mDBtPBfpm), 9-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2': 4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr), 9-[3'(-dibenzothiophen-4-yl)biphenyl-4-yl]naphtho[1',2':4,5 ]furo[2,3-b]pyrazine (abbreviation: 9pmDBtBPNfpr), 11-[3'(-dibenzothiophen-4-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[ 2,3-b]pyrazine (abbreviation: 11mDBtBPPnfpr), 11-[3'(-dibenzothiophen-4-yl)biphenyl-4-yl]phenanthro[9',10':4,5]furo[2,3 -b]pyrazine, 11-[3'-(9H-carbazol-9-yl)biphenyl-3-yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazine, 12- (9'-Phenyl-3,3'-bi-9H-carbazol-9-yl)phenanthro[9',10':4,5]furo[2,3-b]pyrazine (abbreviation: 12PCCzPnfpr), 9- [(3′-9-phenyl-9H-carbazol-3-yl)biphenyl-4-yl]naphtho[1′,2′:4,5]furo[2,3-b]pyrazine (abbreviation: 9pmPCBPNfpr), 9-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9PCCzNfpr), 10-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 10PCCzNfpr), 9-[3'-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl)biphenyl-3-yl]naphtho[1',2':4,5]furo[2, 3-b]pyrazine (abbreviation: 9mBnfBPNfpr), 9-{3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophen-4-yl]phenyl}naphtho[1',2':4, 5]furo[2,3-b]pyrazine (abbreviation: 9mFDBtPNfpr), 9-[3'-(6-phenyldibenzothiophen-4-yl)biphenyl-3-yl]naphtho[1',2':4, 5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr-02), 9-[3-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)phenyl]naphtho[1 ',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mPCCzPNfpr), 9-{(3'-[2,8-diphenyldibenzothiophen-4-yl]biphenyl-3-yl} Naphtho[1',2':4,5]furo[2,3-b]pyrazine, 11-{(3'-[2,8-diphenyldibenzothiophen-4-yl]biphenyl-3-yl}phenanthro[ 9',10':4,5]furo[2,3-b]pyrazine, 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7 -dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenylen-2-yl)-1,1'-biphenyl-3-yl ]-4,6-diphenyl-1,3,5-triazine (abbreviation: mTpBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'- Spirobi(9H-fluoren)-2-yl]-1,3,5-triazine (abbreviation: BP-SFTZn), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3 -pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9- Phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-[1,1'-biphenyl]-3-yl-4-phenyl-6-(8-[1,1':4',1''-terphenyl ]-4-yl-1-dibenzofuranyl)-1,3,5-triazine (abbreviation: mBP-TPDBfTzn), 6-(1,1'-biphenyl-3-yl)-4-[3,5- Bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6 -(1,1'-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), an organic compound containing a heteroaromatic ring having a diazine ring, and the like, all of which are preferable as host materials.

[0275] Among the above organic compounds, a specific example of the metal complex, which is an organic compound having a high electron transport property, is a zinc-based or aluminum-based metal complex, tris(8-quinolinolato)aluminum (III) (abbreviation : Alq), tris(4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq 2 ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq), quinoline ring or A metal complex having a benzoquinoline ring and the like can be mentioned, and all of these are preferable as the host material.

[0276] In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF) -Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) Molecular compounds and the like are also preferred as host materials.

[0277] Furthermore, the bipolar 9-phenyl-9'-(4-phenyl-2-quinazolinyl)-3,3'-bipolar compound, which is an organic compound with a high hole-transport property and a high electron-transport property, -9H-carbazole (abbreviation: PCCzQz), 2-[4'-(9-phenyl-9H-carbazol-3-yl)-3,1'-biphenyl-1-yl]dibenzo[f,h]quinoxaline (abbreviation: PCCzQz) :2mpPCBPDBq), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 11-(4-[1,1'-biphenyl]-4-yl-6-phenyl-1,3,5-triazin-2-yl)-11,12-dihydro -12-phenyl-indolo[2,3-a]carbazole (abbreviation: BP-Icz(II)Tzn), 7-[4-(9-phenyl-9H-carbazol-2-yl)quinazolin-2-yl] An organic compound having a diazine ring such as -7H-dibenzo[c,g]carbazole (abbreviation: PC-cgDBCzQz) can also be used as a host material.

[0278] <Electron transport layer> The electron transport layers (114, 114a, 114b) transfer electrons injected from the second electrode 102 and the charge generation layers (106, 106a, 106b) by the electron injection layers (115, 115a, 115b) described later into the light emitting layer ( 113, 113a, 113b). Note that the heat resistance of the light-emitting device, which is one embodiment of the present invention, can be improved when the electron-transport layer has a layered structure. Further, the electron-transporting material used for the electron-transporting layers (114, 114a, 114b) has an electron mobility of 1×10 at the square root of the electric field strength [V / cm] of 600. -6 cm 2 Substances with an electron mobility of / Vs or higher are preferred. Note that any substance other than these substances can be used as long as it has a higher electron-transport property than hole-transport property. In addition, the electron transport layers (114, 114a, 114b) function as a single layer, but may have a laminated structure of two or more layers. Since the above mixed material has heat resistance, the effect of the heat process on the device characteristics can be suppressed by performing a photolithography process on the electron transport layer using the mixed material.

[0279] <<Electron-transporting material>> As an electron-transporting material that can be used for the electron-transporting layers (114, 114a, 114b), an organic compound having a high electron-transporting property can be used, for example, a heteroaromatic compound can be used. A heteroaromatic compound is a cyclic compound containing at least two different elements in the ring. The ring structure includes a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, etc., and a 5-membered ring or a 6-membered ring is particularly preferable. Heteroaromatic compounds containing any one or more of nitrogen, oxygen, or sulfur are preferred. In particular, nitrogen-containing heteroaromatic compounds (nitrogen-containing heteroaromatic compounds) are preferable, and materials with high electron transport properties such as nitrogen-containing heteroaromatic compounds or π-electron deficient heteroaromatic compounds containing these (electron transport properties) material) is preferably used. Since the compound of Embodiment 1 has an electron-transporting property, it can be used as an electron-transporting material.

[0280] A material different from the material used for the light-emitting layer can also be used for this electron-transporting material. Not all excitons generated by recombination of carriers in the light-emitting layer can contribute to light emission, and may diffuse into layers in contact with or in the vicinity of the light-emitting layer. In order to avoid this phenomenon, the energy level (lowest singlet excited level or lowest triplet excited level) of the material used for the layer adjacent to or in the vicinity of the light emitting layer is used for the light emitting layer. preferably higher than the material. Therefore, by using an electron-transporting material different from the material used for the light-emitting layer, an element with high efficiency can be obtained.

[0281] A heteroaromatic compound is an organic compound having at least one heteroaromatic ring.

[0282] The heteroaromatic ring has any one of a pyridine ring, a diazine ring, a triazine ring, a polyazole ring, an oxazole ring, a thiazole ring, and the like. In addition, heteroaromatic rings having a diazine ring include heteroaromatic rings having a pyrimidine ring, a pyrazine ring, a pyridazine ring, or the like. Moreover, heteroaromatic rings having a polyazole ring include heteroaromatic rings having an imidazole ring, a triazole ring, and an oxadiazole ring.

[0283] A heteroaromatic ring also includes a fused heteroaromatic ring having a fused ring structure. The condensed heteroaromatic ring includes quinoline ring, benzoquinoline ring, quinoxaline ring, dibenzoquinoxaline ring, quinazoline ring, benzoquinazoline ring, dibenzoquinazoline ring, phenanthroline ring, furodiazine ring, and benzimidazole ring.

[0284] For example, among heteroaromatic compounds containing one or more of nitrogen, oxygen, or sulfur in addition to carbon, heteroaromatic compounds having a 5-membered ring structure include heteroaromatic compounds having an imidazole ring compounds, heteroaromatic compounds having a triazole ring, heteroaromatic compounds having an oxazole ring, heteroaromatic compounds having an oxadiazole ring, heteroaromatic compounds having a thiazole ring, heteroaromatic compounds having a benzimidazole ring, etc. is mentioned.

[0285] Further, for example, among heteroaromatic compounds containing one or more of nitrogen, oxygen, sulfur, etc. in addition to carbon, heteroaromatic compounds having a six-membered ring structure include a pyridine ring, a diazine ring (pyrimidine ring, pyrazine ring, pyridazine ring, etc.), heteroaromatic compounds having heteroaromatic rings such as triazine ring and polyazole ring. It is included in heteroaromatic compounds having a structure in which pyridine rings are linked, and includes heteroaromatic compounds having a bipyridine structure and heteroaromatic compounds having a terpyridine structure.

[0286] Furthermore, the heteroaromatic compound having a condensed ring structure partially including the six-membered ring structure includes a quinoline ring, a benzoquinoline ring, a quinoxaline ring, a dibenzoquinoxaline ring, a phenanthroline ring, and a (including structures in which aromatic rings are condensed), heteroaromatic compounds having condensed heteroaromatic rings such as benzimidazole rings, and the like.

[0287] Specific examples of the heteroaromatic compound having a five-membered ring structure (polyazole ring (including imidazole ring, triazole ring, oxadiazole ring), oxazole ring, thiazole ring, benzimidazole ring, etc.) include 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), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H- Carbazole (abbreviation: CO11), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert- Butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), 2,2',2''-(1,3, 5-Benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: TPBI) mDBTBIm-II), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), and the like.

[0288] Specific examples of the heteroaromatic compound having a 6-membered ring structure (including a heteroaromatic ring having a pyridine ring, a diazine ring, a triazine ring, etc.) include 3,5-bis[3-(9H-carbazole-9 -yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), etc. Compound, 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation : PCCzPTzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn -02), 5-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-7,7-dimethyl-5H,7H-indeno[2,1-b]carbazole (abbreviation: mINc(II)PTzn), 2-[3'-(triphenylen-2-yl)-1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine ( Abbreviation: mTpBPTzn), 2-[(1,1'-biphenyl)-4-yl]-4-phenyl-6-[9,9'-spirobi(9H-fluoren)-2-yl]-1,3, 5-triazine (abbreviation: BP-SFTzn), 2,6-bis(4-naphthalen-1-ylphenyl)-4-[4-(3-pyridyl)phenyl]pyrimidine (abbreviation: 2,4NP-6PyPPm), 3-[9-(4,6-diphenyl-1,3,5-triazin-2-yl)-2-dibenzofuranyl]-9-phenyl-9H-carbazole (abbreviation: PCDBfTzn), 2-[1, 1'-biphenyl]-3-yl-4-phenyl-6-(8-[1,1':4',1''-terphenyl]-4-yl-1-dibenzofuranyl)-1,3 ,5-triazine (abbreviation: mBP-TPDBfTzn), 2-{3-[3-(dibenzothiophen-4-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: mDBtBPTzn) ), heteroaromatic compounds containing a heteroaromatic ring with a triazine ring such as mFBPTzn, 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis [3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 4,6mCzBP2Pm, 6-(1,1'-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm) , 4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenyl-6-(1,1'-biphenyl-4-yl)pyrimidine (abbreviation: 6BP-4Cz2PPm), 4- [3-(Dibenzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfpm), 8BP-4mDBtPBfpm, 9mDBtBPNfpr, 9pmDBtBPNfpr, 3,8-bis[3-(dibenzothiophen-4-yl)phenyl]benzofuro[2,3-b]pyrazine (abbreviation: 3,8mDBtP2Bfpr), 4,8-bis[3-(dibenzothiophene-4 -yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm), 8-[3'-(dibenzothiophen-4-yl)(1,1'-biphenyl-3- yl)]naphtho[1',2':4,5]furo[3,2-d]pyrimidine (abbreviation: 8mDBtBPNfpm), 8-[(2,2'-binaphthalene)-6-yl]-4-[ Heteroaromatic rings containing a diazine (pyrimidine) ring such as 3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8(βN2)-4mDBtPBfpm) aromatic compounds, and the like. The aromatic compound containing a heteroaromatic ring includes a heteroaromatic compound having a condensed heteroaromatic ring.

[0289] In addition, 2,2'-(pyridine-2,6-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2,2'-(2 ,2'-bipyridine-6,6'-diyl)bis(4-phenylbenzo[h]quinazoline) (abbreviation: 6,6'(P-Bqn)2BPy), 2,2'-(pyridine-2,6 -diyl)bis{4-[4-(2-naphthyl)phenyl]-6-phenylpyrimidine} (abbreviation: 2,6(NP-PPm) 2 Py), 6-(1,1′-biphenyl-3-yl)-4-[3,5-bis(9H-carbazol-9-yl)phenyl]-2-phenylpyrimidine (abbreviation: 6mBP-4Cz2PPm), Heteroaromatic compounds containing a heteroaromatic ring with a diazine (pyrimidine) ring such as 2,4,6-tris[3'-(pyridin-3-yl)biphenyl-3-yl]-1,3,5- Triazine (abbreviation: TmPPPyTz), 2,4,6-tris(2-pyridyl)-1,3,5-triazine (abbreviation: 2Py3Tz), 2-[3-(2,6-dimethyl-3-pyridinyl)- 5-(9-phenanthrenyl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), heteroaromatic compounds containing a heteroaromatic ring having a triazine ring, and the like. be done.

[0290] Specific examples of the above heteroaromatic compounds having a condensed ring structure partially containing a six-membered ring structure (heteroaromatic compounds having a condensed ring structure) include bathophenanthroline (abbreviation: BPhen) and bathocuproine (abbreviation: BCP). ), 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBPhen), 2,2'-(pyridine-2,6-diyl)bis(4- Phenylbenzo[h]quinazoline) (abbreviation: 2,6(P-Bqn)2Py), 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II) , 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl )biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline ( abbreviation: 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]quinoxaline (abbreviation: 6mDBTPDBq-II), 2mpPCBPDBq, and other heteroaromatic compounds having a quinoxaline ring.

[0291] For the electron transport layers (114, 114a, 114b), metal complexes shown below can be used in addition to the heteroaromatic compounds shown above. Tris(8-quinolinolato)aluminum(III) (abbreviation: Alq) 3 ), Almq 3 , 8-quinolinolatritium (I) (abbreviation: Liq), BeBq 2 , bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq) or quinoline rings such as benzoquinoline Ring-bearing metal complexes, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ) metal complexes having an oxazole ring or a thiazole ring such as

[0292] In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF -Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) A molecular compound can also be used as an electron-transporting material.

[0293] Further, the electron transport layers (114, 114a, 114b) are not limited to a single layer, and may have a structure in which two or more layers made of the above substances are laminated.

[0294] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing substances with high electron injection properties. In addition, the electron injection layers (115, 115a, 115b) are layers for increasing the injection efficiency of electrons from the second electrode 102, and the work function value of the material used for the second electrode 102 and the electron injection When comparing the LUMO level values ​​of the materials used for the layers (115, 115a, 115b), it is preferable to use a material with a small difference (0.5 eV or less). Therefore, the electron injection layer 115 includes lithium, cesium, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), 2 ), 8-quinolinolatritium (I) (abbreviation: Liq), 2-(2-pyridyl)phenoratritium (abbreviation: LiPP), 2-(2-pyridyl)-3-pyridinolatritium (abbreviation: LiPPy ), 4-phenyl-2-(2-pyridyl)phenolatolithium (abbreviation: LiPPP), lithium oxide (LiO x ), alkali metals such as cesium carbonate, alkaline earth metals, or compounds thereof. In addition, erbium fluoride (ErF 3 ), ytterbium (Yb) or rare earth metal compounds can be used. The electron injection layers (115, 115a, 115b) may be formed by mixing a plurality of the above materials, or may be formed by stacking a plurality of the above materials. Electride may also be used for the electron injection layers (115, 115a, 115b). Examples of the electride include a mixed oxide of calcium and aluminum to which electrons are added at a high concentration. It should be noted that the materials that constitute the electron transport layers (114, 114a, 114b) described above can also be used.

[0295] A mixed material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layers (115, 115a, 115b). Such a mixed material has excellent electron injection properties and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons. Specifically, for example, an electron-transporting material (metal complex and heteroaromatic compounds, etc.) can be used. As the electron donor, any substance can be used as long as it exhibits an electron donating property with respect to an organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium and the like. Further, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used. Also, a plurality of these materials may be laminated and used.

[0296] Alternatively, a mixed material obtained by mixing an organic compound and a metal may be used for the electron injection layers (115, 115a, 115b). Note that the organic compound used here preferably has a LUMO (Lowest Unoccupied Molecular Orbital) level of −3.6 eV or more and −2.3 eV or less. Also, a material having a lone pair of electrons is preferred.

[0297] Therefore, as the organic compound used for the mixed material, the mixed material obtained by mixing the heteroaromatic compound with the metal, which can be used for the electron transport layer, may be used. Heteroaromatic compounds include heteroaromatic compounds having a five-membered ring structure (imidazole ring, triazole ring, oxazole ring, oxadiazole ring, thiazole ring, benzimidazole ring, etc.), six-membered ring structures (pyridine ring, diazine ring, etc.). Heteroaromatic compounds having a ring (including pyrimidine ring, pyrazine ring, pyridazine ring, etc.), triazine ring, bipyridine ring, terpyridine ring, etc., condensed ring structures containing a six-membered ring structure (quinoline ring, benzoquinoline A material having a lone pair of electrons, such as a heteroaromatic compound having a ring, a quinoxaline ring, a dibenzoquinoxaline ring, a phenanthroline ring, etc., is preferred. Since the specific materials have been described above, the description is omitted here.

[0298] As the metal used in the mixed material, it is preferable to use transition metals belonging to Groups 5, 7, 9 or 11 in the periodic table and materials belonging to Group 13. For example, Ag , Cu, Al, or In. Also, at this time, the organic compound forms a semi-occupied molecular orbital (SOMO) with the transition metal.

[0299] For example, when amplifying the light obtained from the light emitting layer 113b, the optical distance between the second electrode 102 and the light emitting layer 113b is less than 1 / 4 of the wavelength λ of the light emitted by the light emitting layer 113b. It is preferable to form In this case, it can be adjusted by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.

[0300] Further, as in the light-emitting device shown in FIG. 1(D), by providing the charge generation layer 106 between the two EL layers (103a, 103b), a structure in which a plurality of EL layers are stacked between a pair of electrodes. (Also referred to as a tandem structure).

[0301] <Charge generation layer> The charge generation layer 106 injects electrons into the EL layer 103a and holes into the EL layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. It has the function of injecting. Even if the charge generation layer 106 has a structure in which an electron acceptor (acceptor) is added to a hole transport material (also referred to as a P-type layer), an electron donor (donor) is added to the electron transport material. A structure (also referred to as an electron injection buffer layer) may be used. Also, both of these configurations may be stacked. Furthermore, an electron relay layer may be provided between the P-type layer and the electron injection buffer layer. By forming the charge generation layer 106 using the materials described above, it is possible to suppress an increase in drive voltage when EL layers are stacked.

[0302] When the charge-generating layer 106 has a structure (P-type layer) in which an electron acceptor is added to a hole-transporting material that is an organic compound, the hole-transporting material may be the material shown in this embodiment. can be used. In addition, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F 4 -TCNQ), chloranil and the like. Further, oxides of metals belonging to groups 4 to 8 in the periodic table can be mentioned. Specific examples include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide. Note that the acceptor material described above may be used. Further, it may be used as a mixed film obtained by mixing materials constituting the P-type layer, or may be laminated with single films containing each material.

[0303] When the charge generation layer 106 has a structure in which an electron donor is added to an electron-transporting material (an electron-injecting buffer layer), the material shown in this embodiment can be used as the electron-transporting material. can. As the electron donor, alkali metals, alkaline earth metals, rare earth metals, metals belonging to Groups 2 and 13 in the periodic table, and oxides and carbonates thereof can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide (Li 2 O), cesium carbonate and the like are preferably used. Alternatively, an organic compound such as tetrathianaphthacene may be used as an electron donor.

[0304] When an electron relay layer is provided between the P-type layer and the electron-injection buffer layer in the charge-generating layer 106, the electron-relay layer contains at least a substance having an electron-transport property, and the electron-injection buffer layer and the P-type layer interact with each other. It has the function of preventing the action and transferring electrons smoothly. The LUMO level of the electron-transporting substance contained in the electron relay layer is the LUMO level of the acceptor substance in the P-type layer and the LUMO level of the electron-transporting substance contained in the electron transport layer in contact with the charge generation layer. It is preferably between levels. A specific energy level of the LUMO level in the substance having an electron-transporting property used for the electron relay layer is -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. It is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand as an electron-transporting substance used for the electron-relay layer.

[0305] Although FIG. 1D shows a structure in which two EL layers 103 are stacked, a stacked structure of three or more EL layers may be employed by providing a charge generation layer between different EL layers.

[0306] <Cap layer> Note that although not shown in FIGS. 1A to 1E, a cap layer may be provided over the second electrode 102 of the light-emitting device. For example, a material with a high refractive index can be used for the cap layer. By providing the cap layer on the second electrode 102, the extraction efficiency of light emitted from the second electrode 102 can be improved.

[0307] Specific examples of materials that can be used for the cap layer include 5,5′-diphenyl-2,2′-di-5H-[1]benzothieno[3,2-c]carbazole (abbreviation: BisBTc), 4,4 ',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and the like. Further, the organic compounds described in Embodiment 1 can be used.

[0308] <Substrate> The light-emitting device described in this embodiment can be formed over various substrates. Note that the type of substrate is not limited to a specific one. Examples of substrates include semiconductor substrates (for example, single crystal substrates or silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates, metal substrates, stainless steel substrates, substrates with stainless steel foil, tungsten substrates, Substrates with tungsten foil, flexible substrates, laminated films, papers containing fibrous materials, or substrate films.

[0309] Note that examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, soda lime glass, and the like. Examples of flexible substrates, laminated films, and base films include plastics such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), and acrylic resins. Synthetic resin, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid, epoxy resin, inorganic deposition film, paper, and the like.

[0310] Note that a vapor phase method such as an evaporation method, a liquid phase method such as a spin coating method, or an inkjet method can be used for manufacturing the light-emitting device described in this embodiment mode. When vapor deposition is used, physical vapor deposition (PVD method) such as sputtering, ion plating, ion beam vapor deposition, molecular beam vapor deposition, vacuum vapor deposition, chemical vapor deposition (CVD method), etc. should be used. can be done. In particular, the layers having various functions (hole injection layer 111, hole transport layer 112, light emitting layer 113, electron transport layer 114, electron injection layer 115) included in the EL layer of the light emitting device are formed by vapor deposition (vacuum vapor deposition). method, etc.), coating method (dip coating method, die coating method, bar coating method, spin coating method, spray coating method, etc.), printing method (inkjet method, screen (stencil printing) method, offset (lithographic printing) method, flexo ( It can be formed by a method such as a letterpress printing method, a gravure method, a microcontact method, or the like.

[0311] In the case of applying a film forming method such as the above coating method or printing method, high molecular compounds (oligomers, dendrimers, polymers, etc.), middle molecular compounds (compounds in the intermediate region between low molecular weight and high molecular weight: molecular weight 400 to 4000 below), inorganic compounds (quantum dot materials, etc.), and the like can be used. As the quantum dot material, a colloidal quantum dot material, an alloy quantum dot material, a core-shell quantum dot material, a core quantum dot material, or the like can be used.

[0312] Each layer (hole-injection layer 111, hole-transport layer 112, light-emitting layer 113, electron-transport layer 114, electron-injection layer 115) constituting EL layer 103 of the light-emitting device shown in this embodiment is The materials are not limited to those shown, and other materials can be used in combination as long as they can satisfy the functions of each layer.

[0313] Note that in this specification and the like, the terms “layer” and “film” can be interchanged as appropriate.

[0314] The structure described in this embodiment can be combined as appropriate with any of the structures described in other embodiments.

[0315] (Embodiment 3) In this embodiment, a specific structure example and an example of a manufacturing method of a light emitting and receiving device which is one embodiment of the present invention will be described.

[0316] <Configuration example of light emitting / receiving device 700> The light receiving and emitting device 700 shown in FIG. 2A has a light emitting device 550B, a light emitting device 550G, a light emitting device 550R, and a light receiving device 550PS. Also, the light-emitting device 550B, the light-emitting device 550G, the light-emitting device 550R, and the light-receiving device 550PS are formed on the functional layer 520 provided on the first substrate 510. FIG. The functional layer 520 includes driving circuits such as a gate driver and a source driver configured by a plurality of transistors, wirings electrically connecting them, and the like. These drive circuits are electrically connected to, for example, the light emitting device 550B, the light emitting device 550G, the light emitting device 550R, and the light receiving device 550PS, and can drive them. In addition, the light receiving and emitting device 700 includes an insulating layer 705 on the functional layer 520 and each device (light emitting device and light receiving device), and the insulating layer 705 has a function of bonding the second substrate 770 and the functional layer 520 together. .

[0317] Light-emitting device 550B, light-emitting device 550G, and light-emitting device 550R have the device structure shown in the second embodiment. That is, each light-emitting device has a different EL layer 103 shown in FIG. 2(A). In this embodiment, each device (a plurality of light-emitting devices and a light-receiving device) is formed separately. layer) and part of the active layer of the light receiving device (the first transport layer and the second transport layer) may be simultaneously formed of the same material in the manufacturing process. A detailed description will be given in an eighth embodiment.

[0318] In this specification and the like, a light-emitting layer of each color light-emitting device (for example, blue (B), green (G), and red (R)) and a light-receiving layer of a light-receiving device are separately manufactured or painted separately. It is sometimes called a (Side By Side) structure. Note that although the light emitting device 550B, the light emitting device 550G, the light emitting device 550R, and the light receiving device 550PS are arranged in this order in the light receiving and emitting device 700 illustrated in FIG. 2A, one embodiment of the present invention is not limited to this configuration. For example, in the light emitting / receiving device 700, these devices may be arranged in order of the light emitting device 550R, the light emitting device 550G, the light emitting device 550B, and the light receiving device 550PS.

[0319] In FIG. 2A, a light-emitting device 550B has an electrode 551B, an electrode 552, and an EL layer 103B. Light emitting device 550G also has electrode 551G, electrode 552, and EL layer 103G. Also, the light emitting device 550R has an electrode 551R, an electrode 552, and an EL layer 103R. Also, the light receiving device 550PS has an electrode 551PS, an electrode 552, and a light receiving layer 103PS. The specific configuration of each layer of the light receiving device is as shown in the second embodiment. Further, the specific configuration of each layer of the light-emitting device is as shown in the second embodiment. Also, the EL layer 103B, EL layer 103G, and EL layer 103R have a laminated structure composed of a plurality of layers with different functions, including light-emitting layers (105B, 105G, 105R). In addition, light receiving layer 103PS has a laminated structure composed of a plurality of layers having different functions, including active layer 105PS. FIG. 2A shows the case where EL layer 103B has hole injection / transport layer 104B, light emitting layer 105B, electron transport layer 108B, and electron injection layer 109, and EL layer 103G is a hole injection / transport layer. 104G, a light-emitting layer 105G, an electron-transporting layer 108G, and an electron-injecting layer 109, and an EL layer 103R includes a hole-injection / transporting layer 104R, a light-emitting layer 105R, an electron-transporting layer 108R, and an electron-injecting layer 109. Although the case is illustrated and the light-receiving layer 103PS includes the first transport layer 104PS, the active layer 105PS, the second transport layer 108PS, and the electron injection layer 109, the present invention is not limited to this. The hole injection / transport layers (104B, 104G, 104R) are layers having the functions of the hole injection layer and the hole transport layer described in Embodiment 2, and may have a laminated structure.

[0320] The electron transport layers (108B, 108G, 108R) and the second transport layer 108PS function to block holes moving from the anode side to the cathode side through the EL layers (103B, 103G, 103R). may have Further, the electron injection layer 109 may have a layered structure partially or wholly formed using different materials.

[0321] Further, as shown in FIG. 2(A), among the layers included in the EL layers (103B, 103G, 103R), hole injection / transport layers (104B, 104G, 104R), light emitting layers (105B, 105G, 105R), and the side surfaces (or edges) of the electron transport layers (108B, 108G, 108R) and the side surfaces (or ends) of the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS among the layers of the light-receiving layer 103PS. Alternatively, the insulating layer 107 may be formed on the edge). The insulating layer 107 is formed in contact with the side surfaces (or ends) of the EL layers (103B, 103G, 103R) and the light receiving layer 103PS. This makes it possible to suppress the intrusion of oxygen, moisture, or their constituent elements from the side surfaces of the EL layers (103B, 103G, 103R) and the absorption layer 103PS into the inside. Note that for the insulating layer 107, for example, aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, or silicon nitride oxide can be used. Also, the insulating layer 107 may be formed by stacking the materials described above. The insulating layer 107 can be formed by a sputtering method, a CVD method, an MBE method, a PLD method, an ALD method, or the like, but the ALD method, which has good coverage, is more preferable. Note that the insulating layer 107 has a structure that continuously covers part of the EL layers (103B, 103G, 103R) of the adjacent light-emitting device or part of the side surface (or end) of the light-receiving layer 103PS of the light-receiving device. have. For example, in FIG. 2A, the sides of part of the EL layer 103B of the light emitting device 550B and part of the EL layer 103G of the light emitting device 550G are covered with the insulating layer 107BG. In addition, partition walls 528 made of an insulating material are preferably formed in the region covered with the insulating layer 107BG as shown in FIG. 2(A).

[0322] Further, an electron injection layer 109 is formed on the electron transport layers (108B, 108G, 108R) and the insulating layer 107 which are part of the EL layers (103B, 103G, 103R). Note that the electron injection layer 109 may have a laminated structure of two or more layers (for example, a laminated structure of layers having different electrical resistances, etc.).

[0323] Also, an electrode 552 is formed on the electron injection layer 109 . Note that the electrodes (551B, 551G, 551R) and the electrode 552 have regions that overlap each other. Further, a light-emitting layer 105B is formed between the electrodes 551B and 552, a light-emitting layer 105G is formed between the electrodes 551G and 552, a light-emitting layer 105R is formed between the electrodes 551R and 552, and a light-emitting layer 105R is formed between the electrodes 551PS and 552. Each has a light-receiving layer 103PS.

[0324] Also, the EL layers (103B, 103G, 103R) shown in FIG. 2A have the same configuration as EL layer 103 described in the second embodiment. Further, for example, the light emitting layer 105B can emit blue light, the light emitting layer 105G can emit green light, and the light emitting layer 105R can emit red light.

[0325] Partitions 528 are provided between the electrodes (551B, 551G, 551R, 551PS), part of the EL layers (103B, 103G, 103R), and part of the light-receiving layer 103PS. In addition, as shown in FIG. 2(A), the electrodes (551B, 551G, 551R, 551PS) of each device, part of the EL layers (103B, 103G, 103R), part of the light-receiving layer 103PS, and partition walls 528 are in contact with each other at the side surface (or end) via the insulating layer 107 .

[0326] In each EL layer and light-receiving layer, the hole-injecting layers included in the hole-transporting regions, especially those located between the anode and the light-emitting layer, and between the anode and the active layer, are often highly conductive, and thus adjacent to each other. If formed as a common layer between devices, it may cause crosstalk. Therefore, by providing a partition 528 made of an insulating material between each EL layer and light-receiving layer as shown in this configuration example, adjacent devices (between light-receiving devices and light-emitting devices, between light-emitting devices and light-emitting devices) are provided. It is possible to suppress the occurrence of crosstalk that occurs between light-receiving devices (or between light-receiving devices).

[0327] In addition, in the manufacturing method described in the present embodiment, the side surfaces (or end portions) of the EL layer and light-receiving layer are exposed during the patterning process. Therefore, the deterioration of the EL layer and the light-receiving layer is likely to progress due to the intrusion of oxygen, water, etc. from the side surfaces (or ends) of the EL layer and the light-receiving layer. Therefore, by providing the partition wall 528, deterioration of the EL layer and the light-receiving layer in the manufacturing process can be suppressed.

[0328] In addition, by providing the partition wall 528, a concave portion formed between adjacent devices (between a light receiving device and a light emitting device, between a light emitting device and a light emitting device, or between a light receiving device and a light receiving device) is flattened. is also possible. By flattening the concave portion, disconnection of the electrode 552 formed on each EL layer and the light-receiving layer can be suppressed. Examples of insulating materials used to form the partition walls 528 include acrylic resins, polyimide resins, epoxy resins, imide resins, polyamide resins, polyimideamide resins, silicone resins, siloxane resins, benzocyclobutene resins, phenol resins, and Organic materials such as precursors of these resins can be applied. Organic materials such as polyvinyl alcohol (PVA), polyvinyl butyral, polyvinylpyrrolidone, polyethylene glycol, polyglycerin, pullulan, water-soluble cellulose, or alcohol-soluble polyamide resins may also be used. A photosensitive resin such as photoresist can also be used. A positive material or a negative material can be used as the photosensitive resin.

[0329] By using a photosensitive resin, the partition walls 528 can be manufactured only through the steps of exposure and development. Alternatively, the partition 528 may be formed using a negative photosensitive resin (for example, a resist material). In the case where an insulating layer containing an organic material is used for the partition 528, a material that absorbs visible light is preferably used. When a material that absorbs visible light is used for the partition 528, the emission from the EL layer can be absorbed by the partition 528, and light (stray light) that can leak to the adjacent EL layer and light-receiving layer can be suppressed. Therefore, a display panel with high display quality can be provided.

[0330] In addition, the difference between the height of the upper surface of the partition 528 and the height of the upper surface of any one of the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS is, for example, 0.5 times or less the thickness of the partition 528. It is preferable, and 0.3 times or less is more preferable. Further, for example, the partition 528 may be provided such that the upper surface of any one of the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS is higher than the upper surface of the partition 528. Further, for example, the partition 528 may be provided such that the upper surface of the partition 528 is higher than the upper surfaces of the EL layer 103B, the EL layer 103G, the EL layer 103R, and the light-receiving layer 103PS.

[0331] In a high-definition light emitting / receiving device (display panel) exceeding 1000ppi, crosstalk occurs when electrical continuity is observed between the EL layer 103B, EL layer 103G, EL layer 103R, and light receiving layer 103PS. , the displayable color gamut of the light receiving and emitting device is narrowed. A high-definition display panel exceeding 1000 ppi, preferably a high-definition display panel exceeding 2000 ppi, more preferably an ultra-high-definition display panel exceeding 5000 ppi, and providing a partition wall 528 provides a display panel capable of displaying vivid colors. can provide.

[0332] 2(B) and (C) are schematic top views of the light emitting / receiving device 700 corresponding to the dashed-dotted line Ya-Yb in the cross-sectional view of FIG. 2(A). That is, the light emitting device 550B, the light emitting device 550G, and the light emitting device 550R are each arranged in a matrix. Note that FIG. 2(B) shows a so-called stripe arrangement in which light emitting devices of the same color are arranged in the X direction. Also, FIG. 2(C) shows a configuration in which light emitting devices of the same color are arranged in the X direction, but a pattern is formed for each pixel. Note that the arrangement method of the light emitting devices is not limited to this, and an arrangement method such as a delta arrangement or a zigzag arrangement may be applied, or a pentile arrangement, a diamond arrangement, or the like may be used.

[0333] In addition, in the separation processing of each EL layer (EL layer 103B, EL layer 103G, and EL layer 103R) and light receiving layer 103PS, pattern formation is performed by photolithography, so a high-definition light emitting and receiving device (display panel) can be obtained. can be made. In addition, the edges (side surfaces) of the EL layer processed by pattern formation by photolithography have substantially the same surface (or are positioned substantially on the same plane). At this time, the width (SE) of the gap 580 between each EL layer and the light receiving layer is preferably 5 μm or less, more preferably 1 μm or less.

[0334] In the EL layer, especially the hole-injection layer contained in the hole-transporting region located between the anode and the light-emitting layer is often formed as a layer common to adjacent light-emitting devices because it often has high conductivity. , can cause crosstalk. Therefore, by separating the EL layer by patterning by photolithography as shown in this configuration example, it is possible to suppress the occurrence of crosstalk between adjacent light emitting devices.

[0335] 2(D) is a schematic cross-sectional view corresponding to the dashed-dotted line C1-C2 in FIGS. 2(B) and 2(C). FIG. 2(D) shows the connection portion 130 where the connection electrode 551C and the electrode 552 are electrically connected. In connection portion 130, electrode 552 is provided on connection electrode 551C in contact therewith. A partition wall 528 is provided to cover the end of the connection electrode 551C.

[0336] <Example of manufacturing method of light emitting / receiving device> As shown in FIG. 3A, an electrode 551B, an electrode 551G, an electrode 551R, and an electrode 551PS are formed. For example, a conductive film is formed over the functional layer 520 formed over the first substrate 510 and processed into a predetermined shape using a photolithography method.

[0337] The conductive film can be formed by sputtering, chemical vapor deposition (CVD), molecular beam epitaxy (MBE), vacuum deposition, pulsed laser deposition (PLD). ) method, Atomic Layer Deposition (ALD) method, or the like. The CVD method includes a plasma enhanced CVD (PECVD) method, a thermal CVD method, and the like. Also, one of the thermal CVD methods is a metal organic chemical vapor deposition (MOCVD) method.

[0338] In addition to the photolithography method described above, the conductive film may be processed by a nanoimprint method, a sandblast method, a lift-off method, or the like. Alternatively, an island-shaped thin film may be directly formed by a film formation method using a shielding mask such as a metal mask.

[0339] As the photolithography method, there are typically the following two methods. One is a method of forming a resist mask on a thin film to be processed, processing the thin film by etching or the like, and removing the resist mask. The other is a method of forming a photosensitive thin film, then performing exposure and development to process the thin film into a desired shape. When the former method is used, there are heat treatment steps such as heating after resist coating (PAB: Pre Applied Bake) and heating after exposure (PEB: Post Exposure Bake). In one embodiment of the present invention, a lithography method is used not only for processing a conductive film but also for processing a thin film (a film containing an organic compound or a film partially containing an organic compound) used for forming an EL layer.

[0340] In photolithography, the light used for exposure can be, for example, i-line (wavelength 365 nm), g-line (wavelength 436 nm), h-line (wavelength 405 nm), or a mixture of these. In addition, ultraviolet light, KrF laser light, ArF laser light, or the like can also be used. Moreover, you may expose by a liquid immersion exposure technique. As the light used for exposure, extreme ultraviolet (EUV) light or X-rays may be used. An electron beam can also be used instead of the light used for exposure. The use of extreme ultraviolet light, X-rays, or electron beams is preferable because extremely fine processing is possible. A photomask is not necessary when exposure is performed by scanning a beam such as an electron beam.

[0341] A dry etching method, a wet etching method, a sandblasting method, or the like can be used for etching the thin film using the resist mask.

[0342] Next, as shown in FIG. 3B, the hole injection / transport layer 104B, the light emitting layer 105B, and the electron transport layer 108B are formed on the electrode 551B, the electrode 551G, the electrode 551R, and the electrode 551PS. A vacuum deposition method, for example, can be used to form the hole injection / transport layer 104B, the light emitting layer 105B, and the electron transport layer 108B. Furthermore, a sacrificial layer 110B is formed on the electron transport layer 108B. In forming the hole injection / transport layer 104B, the light emitting layer 105B, and the electron transport layer 108B, the materials shown in Embodiment 2 can be used.

[0343] It should be noted that, for the sacrificial layer 110B, it is preferable to use a film having high resistance to the etching treatment of the hole injection / transport layer 104B, the light emitting layer 105B, and the electron transport layer 108B, that is, a film having a high etching selectivity. Moreover, the sacrificial layer 110B preferably has a laminated structure of a first sacrificial layer and a second sacrificial layer with different etching selectivity. Also, for the sacrificial layer 110B, a film that can be removed by a wet etching method that causes little damage to the EL layer 103B can be used. As an etching material used for wet etching, oxalic acid or the like can be used.

[0344] As the sacrificial layer 110B, for example, an inorganic film such as a metal film, an alloy film, a metal oxide film, a semiconductor film, or an inorganic insulating film can be used. Also, the sacrificial layer 110B can be formed by various film forming methods such as sputtering, vapor deposition, CVD, and ALD.

[0345] As the sacrificial layer 110B, for example, metal materials such as gold, silver, platinum, magnesium, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, aluminum, yttrium, zirconium, and tantalum, or the metal materials can be used. In particular, it is preferable to use a low melting point material such as aluminum or silver.

[0346] As the sacrificial layer 110B, a metal oxide such as indium gallium zinc oxide (In--Ga--Zn oxide, also abbreviated as IGZO) can be used. Furthermore, indium oxide, indium zinc oxide (In-Zn oxide), indium tin oxide (In-Sn oxide), indium titanium oxide (In-Ti oxide), indium tin zinc oxide (In-Sn -Zn oxide), indium titanium zinc oxide (In-Ti-Zn oxide), indium gallium tin zinc oxide (In-Ga-Sn-Zn oxide), and the like can be used. Alternatively, indium tin oxide containing silicon or the like can be used.

[0347] In place of gallium, element M (M is aluminum, silicon, boron, yttrium, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium, neodymium, hafnium, tantalum, tungsten , or one or more selected from magnesium).

[0348] Inorganic insulating materials such as aluminum oxide, hafnium oxide, and silicon oxide can be used as the sacrificial layer 110B.

[0349] Moreover, as the sacrificial layer 110B, it is preferable to use a material that can be dissolved in a chemically stable solvent at least for the electron transport layer 108B located on the top. In particular, a material that dissolves in water or alcohol can be suitably used for the sacrificial layer 110B. When forming the sacrificial layer 110B, it is preferable to apply the sacrificial layer 110B dissolved in a solvent such as water or alcohol by a wet film forming method, and then perform heat treatment to evaporate the solvent. At this time, the solvent can be removed at a low temperature and in a short time by performing heat treatment in a reduced pressure atmosphere, thereby reducing thermal damage to the hole injection / transport layer 104B, the light emitting layer 105B, and the electron transport layer 108B. It is possible and preferable.

[0350] Note that when the sacrificial layer 110B has a laminated structure, a layer formed of the above materials can be used as the first sacrificial layer, and a second sacrificial layer can be formed thereon to form the laminated structure.

[0351] The second sacrificial layer in this case is a film used as a hard mask when etching the first sacrificial layer. Also, the first sacrificial layer is exposed during the processing of the second sacrificial layer. Therefore, for the first sacrificial layer and the second sacrificial layer, a combination of films having a high etching selectivity to each other is selected. Therefore, a film that can be used for the second sacrificial layer can be selected according to the etching conditions for the first sacrificial layer and the etching conditions for the second sacrificial layer.

[0352] For example, when dry etching using a fluorine-containing gas (also referred to as a fluorine-based gas) is used to etch the second sacrificial layer, silicon, silicon nitride, silicon oxide, tungsten, titanium, molybdenum, tantalum, and nitride can be used. Materials such as tantalum, an alloy containing molybdenum and niobium, or an alloy containing molybdenum and tungsten can be used for the second sacrificial layer. Here, as a film capable of obtaining a high etching selectivity (that is, capable of slowing the etching rate) in dry etching using a fluorine-based gas, there are metal oxide films such as IGZO and ITO. can be used for the first sacrificial layer.

[0353] Note that the second sacrificial layer is not limited to this, and can be selected from various materials according to the etching conditions for the first sacrificial layer and the etching conditions for the second sacrificial layer. For example, it can be selected from films that can be used for the first sacrificial layer.

[0354] A nitride film, for example, can be used as the second sacrificial layer. Specifically, nitrides such as silicon nitride, aluminum nitride, hafnium nitride, titanium nitride, tantalum nitride, tungsten nitride, gallium nitride, and germanium nitride can also be used.

[0355] Alternatively, an oxide film can be used as the second sacrificial layer. Typically, an oxide film or an oxynitride film such as silicon oxide, silicon oxynitride, aluminum oxide, aluminum oxynitride, hafnium oxide, or hafnium oxynitride can be used.

[0356] Next, as shown in FIG. 3(C), a resist is applied onto the sacrificial layer 110B, and the resist is formed into a desired shape (resist mask: REG) by photolithography. When performing such a method, there are heat treatment steps such as heating after resist coating (PAB: Pre Applied Bake) and heating after exposure (PEB: Post Exposure Bake). For example, the PAB temperature is around 100°C, and the PEB temperature is around 120°C. Therefore, a light-emitting device that can withstand these processing temperatures is required.

[0357] Next, using the obtained resist mask REG, a portion of the sacrificial layer 110B that is not covered with the resist mask REG is removed by etching. The layer 104B, the light-emitting layer 105B, and the electron transport layer 108B are removed by etching, and holes are injected and transported into a shape having a side surface (or a side surface being exposed) on the electrode 551B, or a strip-like shape extending in a direction intersecting the plane of the paper. Fabricate layer 104B, light-emitting layer 105B, and electron-transporting layer 108B. Dry etching is preferable for the etching. If the sacrificial layer 110B has a laminated structure of the first sacrificial layer and the second sacrificial layer, the resist mask REG is removed after part of the second sacrificial layer is etched using the resist mask REG. Using the second sacrificial layer as a mask, part of the first sacrificial layer may be etched to process the hole injection / transport layer 104B, the light emitting layer 105B, and the electron transport layer 108B into predetermined shapes. By these etching treatments, the shape shown in FIG. 4(A) is obtained.

[0358] Next, as shown in FIG. 4B, the hole injection / transport layer 104G, the light emitting layer 105G, and the electron transport layer 108G are formed on the sacrificial layer 110B, the electrode 551G, the electrode 551R, and the electrode 551PS. In forming the hole injection / transport layer 104G, the light emitting layer 105G, and the electron transport layer 108G, the materials shown in Embodiment 2 can be used. A vacuum deposition method, for example, can be used to form the hole injection / transport layer 104G, the light emitting layer 105G, and the electron transport layer 108G.

[0359] Next, as shown in FIG. 4(C), a sacrificial layer 110G is formed on the electron transport layer 108G, a resist is applied on the sacrificial layer 110G, and the resist is formed into a desired shape (resist layer) by photolithography. mask: REG), a portion of the sacrificial layer 110G not covered with the obtained resist mask REG is removed by etching, and after removing the resist mask REG, a hole injection / transport layer not covered with the sacrificial layer 110G. Part of 104G, light emitting layer 105G, and electron transport layer 108G is removed by etching, and holes are injected into a shape having a side surface (or a side surface is exposed) on electrode 551G, or a belt-like shape extending in a direction intersecting the plane of the paper. · Process the transport layer 104G, the light emitting layer 105G, and the electron transport layer 108G. Dry etching is preferable for the etching. Also, the sacrificial layer 110G can use the same material as the sacrificial layer 110B. After part of the second sacrificial layer is etched by , the resist mask REG is removed, and using the second sacrificial layer as a mask, part of the first sacrificial layer is etched to form a hole injection / transport layer 104G and a light emitting layer. Layer 105G and electron transport layer 108G may be processed into a predetermined shape. By these etching treatments, the shape of FIG. 5(A) is obtained.

[0360] Next, as shown in FIG. 5B, the hole injection / transport layer 104R, the light emitting layer 105R, and the electron transport layer 108R are formed on the sacrificial layer 110B, the sacrificial layer 110G, the electrode 551R, and the electrode 551PS. In forming the hole injection / transport layer 104R, the light emitting layer 105R, and the electron transport layer 108R, the materials shown in Embodiment 2 can be used. A vacuum deposition method, for example, can be used to form the hole injection / transport layer 104R, the light emitting layer 105R, and the electron transport layer 108R.

[0361] Next, as shown in FIG. 5(C), a sacrificial layer 110R is formed on the electron transport layer 108R, a resist is applied on the sacrificial layer 110R, and the resist is formed into a desired shape (resist layer) by photolithography. mask: REG), a portion of the sacrificial layer 110R not covered with the obtained resist mask REG is removed by etching, and after removing the resist mask REG, a hole injection / transport layer not covered with the sacrificial layer 110R is formed. Part of 104R, light-emitting layer 105R, and electron-transporting layer 108R is removed by etching, and holes are injected into a shape having a side surface (or a side surface is exposed) on electrode 551R, or a strip-like shape extending in a direction intersecting the plane of the paper. · Process the transport layer 104R, the light emitting layer 105R, and the electron transport layer 108R. Dry etching is preferable for the etching. Also, the sacrificial layer 110R can use the same material as the sacrificial layer 110B. After part of the second sacrificial layer is etched by , the resist mask REG is removed, and using the second sacrificial layer as a mask, part of the first sacrificial layer is etched to form a hole injection / transport layer 104R and a light emitting layer. Layer 105R and electron transport layer 108R may be processed into a predetermined shape. By these etching treatments, the shape shown in FIG. 6(A) is obtained.

[0362] Next, as shown in FIG. 6B, a first transport layer 104PS, an active layer 105PS, and a second transport layer 108PS are formed on the sacrificial layer 110B, the sacrificial layer 110G, the sacrificial layer 110R, and the electrode 551PS. do. In forming the first transport layer 104PS, for example, the materials shown for the hole injection layer and the hole transport layer in Embodiment 2 can be used. In addition, in active layer 105PS, the material shown in Embodiment 2 can be used as the material. Further, in forming the second transport layer 108PS, for example, the materials shown for the electron transport layer and the electron injection layer in Embodiment 2 can be used. A vacuum deposition method, for example, can be used to form the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS.

[0363] Next, as shown in FIG. 6(C), a sacrificial layer 110PS is formed on the second transport layer 108PS, a resist is applied on the sacrificial layer 110PS, and the resist is formed into a desired shape using photolithography. (resist mask: REG), a portion of the sacrificial layer 110PS that is not covered with the obtained resist mask REG is removed by etching, and after removing the resist mask REG, a first sacrificial layer 110PS that is not covered with the sacrificial layer 110PS is removed. Parts of the transport layer 104PS, the active layer 105PS, and the second transport layer 108PS are removed by etching to form a shape having a side surface (or a side surface exposed) on the electrode 551PS, or a strip shape extending in a direction intersecting the plane of the paper. Fabricate the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS to shape. Dry etching is preferable for the etching. Also, the sacrificial layer 110PS can use the same material as the sacrificial layer 110B. After part of the second sacrificial layer is etched by , the resist mask REG is removed, and using the second sacrificial layer as a mask, part of the first sacrificial layer is etched to form the first transport layer 104PS, the active Layer 105PS and second transport layer 108PS may be shaped into a predetermined shape. By these etching treatments, the shape of FIG. 6(D) is obtained.

[0364] Next, as shown in FIG. 7A, the insulating layer 107 is formed on the sacrificial layer 110B, the sacrificial layer 110G, the sacrificial layer 110R, and the sacrificial layer 110PS.

[0365] Note that the ALD method, for example, can be used to form the insulating layer 107 . In this case, the insulating layer 107 includes, as shown in FIG. , 108G, 108R), and are formed in contact with each side (each end) of the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light receiving device. As a result, it is possible to suppress the intrusion of oxygen, moisture, or these constituent elements from each side surface into the interior. Note that as a material used for the insulating layer 107, for example, aluminum oxide, magnesium oxide, hafnium oxide, gallium oxide, indium gallium zinc oxide, silicon nitride, or silicon nitride oxide can be used.

[0366] Next, as shown in FIG. 7(B), after removing the sacrificial layers (110B, 110G, 110R, 110PS), the insulating layers (107B, 107G, 107R, 107PS), the electron transport layers (108B, 108G, 108R) are removed. ), and form an electron injection layer 109 on the second transport layer 108PS. The insulating layers (107B, 107G, 107R, 107PS) are formed by partially removing the insulating layer 107 at the same time as removing the sacrificial layers (110B, 110G, 110R, 110PS). In forming the electron injection layer 109, the material shown in Embodiment 2 can be used as the material. Note that the electron injection layer 109 is formed using, for example, a vacuum deposition method. The electron injection layer 109 is formed on the electron transport layers (108B, 108G, 108R) and the second transport layer 108PS. Note that the electron injection layer 109 includes hole injection / transport layers (104B, 104G, 104R), light emitting layers (105B, 105G, 105R), and electron transport layers (108B, 108G, 108R) of each light emitting device. It has a structure in which insulating layers (107B, 107G, 107R, 107PS) are in contact with each side (each end) of the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the device.

[0367] Next, as shown in FIG. 7C, electrodes 552 are formed. Electrode 552 is formed using, for example, a vacuum deposition method. Note that the electrode 552 is formed on the electron injection layer 109 . The electrode 552 is connected to the hole injection / transport layers (104B, 104G, 104R), the light-emitting layers (105B, 105G, 105R), the light-emitting layers (105B, 105G, 105R), and electron transport layers (108B, 108G, 108R), and each side surface (each end) of the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light receiving device. As a result, the hole injection / transport layers (104B, 104G, 104R), the light emitting layers (105B, 105G, 105R), and the electron transport layers (108B, 108G, 108R) of each light emitting device, and the first Electrical short-circuiting between the transport layer 104PS, the active layer 105PS, the second transport layer 108PS and the electrode 552 can be prevented.

[0368] Through the above steps, EL layer 103B, EL layer 103G, EL layer 103R, and light-receiving layer 103PS in light-emitting device 550B, light-emitting device 550G, light-emitting device 550R, and light-receiving device 550PS can be separated.

[0369] In the separation process of these EL layers (EL layer 103B, EL layer 103G, EL layer 103R) and light-receiving layer 103PS, pattern formation is performed by photolithography, so a high-definition light-receiving and emitting device (display panel) can be obtained. can be made. In addition, the edges (side surfaces) of the EL layer processed by pattern formation by photolithography have substantially the same surface (or are positioned substantially on the same plane).

[0370] In addition, since the hole injection / transport layers (104B, 104G, 104R) in these EL layers and the first transport layer 104PS in the light-receiving layer are often highly conductive, they can be used as common layers between adjacent devices. If formed, it may cause crosstalk. Therefore, by separating the EL layers by patterning by photolithography as shown in this configuration example, it is possible to suppress the occurrence of crosstalk between adjacent devices.

[0371] Note that hole injection / transport layers (104B, 104G, 104R) and light emitting layers (105B, 105G, 105R), the electron transport layers (108B, 108G, 108R), and the light receiving layer 103PS of the light receiving device. Since the pattern is formed by lithography, the edges (side surfaces) of the processed EL layer have substantially the same surface (or are positioned substantially on the same plane).

[0372] Further, hole injection / transport layers (104B, 104G, 104R), light-emitting layers (105B, 105G, 105R), and electron transport layers (108B, 108G, 108R), and the first transport layer 104PS, the active layer 105PS, and the second transport layer 108PS of the light-receiving layer 103PS of the light-receiving device are separated by photolithography. Due to patterning, each processed edge (side) has a respective gap 580 between adjacent devices. In FIG. 7C, when the gap 580 is represented by SE as the distance between the EL layers of the adjacent devices, the smaller the distance SE, the higher the aperture ratio and the fineness. On the other hand, as the distance SE increases, the manufacturing yield can be increased because the influence of manufacturing process variations between adjacent devices can be tolerated. Since the light-emitting device manufactured according to the present specification is suitable for a miniaturization process, the distance SE between the EL layers or light-receiving layers of adjacent devices is 0.5 μm or more and 5 μm or less, preferably 1 μm or more and 3 μm or less, more preferably 1 μm or more and 3 μm or less. can be 1 μm or more and 2.5 μm or less, more preferably 1 μm or more and 2 μm or less. Note that, typically, it is preferable that the distance SE is 1 μm or more and 2 μm or less (for example, 1.5 μm or its vicinity).

[0373] In this specification and the like, a device manufactured using a metal mask or FMM (fine metal mask, high-definition metal mask) may be referred to as a device with an MM (metal mask) structure. In this specification and the like, a device manufactured without using a metal mask or FMM may be referred to as a device with an MML (metal maskless) structure.

[0374] Note that the island-shaped EL layer of the light receiving and emitting device having the MML structure is not formed using a fine metal mask, but is formed by processing the EL layer after it is formed. Therefore, it is possible to realize a light emitting / receiving device with higher definition or a higher aperture ratio than ever before. Furthermore, since the EL layer can be produced separately for each color, it is possible to realize a light emitting / receiving device with extremely vivid, high contrast, and high display quality. In addition, by providing the sacrificial layer over the EL layer, damage to the EL layer during the manufacturing process can be reduced, so that the reliability of the light-emitting device can be improved.

[0375] Note that in the light-emitting device 550B, the light-emitting device 550G, and the light-emitting device 550R shown in FIGS. 2A and 7C, the EL layers (103B, 103G, and 103R) are wider than the electrodes (551B, 551G, and 551R). In the light-receiving device 550PS, the width of the light-receiving layer 103PS is approximately equal to the width of the electrode 551PS, but one embodiment of the present invention is not limited to this.

[0376] In light-emitting device 550B, light-emitting device 550G, and light-emitting device 550R, the width of EL layers (103B, 103G, 103R) may be smaller than the width of electrodes (551B, 551G, 551R). Also, in the light receiving device 550PS, the width of the light receiving layer 103PS may be smaller than the width of the electrode 551PS. FIG. 7(D) shows an example in which the width of the EL layers (103B, 103G) is smaller than the width of the electrodes (551B, 551G) in the light emitting device 550B and the light emitting device 550G.

[0377] In light-emitting device 550B, light-emitting device 550G, and light-emitting device 550R, the width of EL layers (103B, 103G, 103R) may be greater than the width of electrodes (551B, 551G, 551R). Moreover, in the light receiving device 550PS, the width of the light receiving layer 103PS may be larger than the width of the electrode 551PS. FIG. 7(E) shows an example in which the width of the EL layer 103R is larger than the width of the electrode 551R in the connection portion 131 of the light emitting device 550R.

[0378] The structure described in this embodiment can be combined as appropriate with any of the structures described in other embodiments.

[0379] (Embodiment 4) In this embodiment, the device 720 will be described with reference to FIGS. 8 to 10. FIG. Note that the device 720 illustrated in FIGS. 8 to 10 is a light-emitting device because it includes the light-emitting device described in Embodiment 2, but the device 720 described in this embodiment can be applied to a display portion of an electronic device or the like. It can also be called a display panel or a display device. Further, when the light emitting device is used as a light source and a light receiving device capable of receiving light from the light emitting device is provided, it can be called a light receiving and emitting device. Note that the light-emitting device, the display panel, the display device, and the light-receiving and emitting device each have at least a light-emitting device.

[0380] Further, the light emitting device, display panel, display device, and light emitting / receiving device of this embodiment can be a high-resolution or large light emitting device, display panel, display device, and light emitting / receiving device. Therefore, the light-emitting device, the display panel, the display device, and the light-receiving device of the present embodiment can be used, for example, in television devices, desktop or notebook personal computers, monitors for computers, digital signage, pachinko machines, and the like. In addition to electronic devices with relatively large screens such as large game consoles, digital cameras, digital video cameras, digital photo frames, mobile phones, portable game consoles, smartphones, wristwatch terminals, tablet terminals, personal digital assistants, and audio equipment It can also be used for a display unit of a playback device or the like.

[0381] FIG. 8A shows a top view of these devices (including a light emitting device, a display panel, a display device, and a light receiving and emitting device) 720. FIG.

[0382] In FIG. 8A, a device 720 has a structure in which a substrate 710 and a substrate 711 are bonded together. The device 720 also includes a display area 701, a circuit 704, wiring 706, and the like. Note that the display region 701 has a plurality of pixels, and the pixel 703(i,j) shown in FIG. 8A is adjacent to the pixel 703(i,j) as shown in FIG. 8B. It has a pixel 703 (i+1,j).

[0383] Further, in the device 720, as shown in FIG. 8A, an example in which an IC (integrated circuit) 712 is provided on the substrate 710 by a COG (Chip On Glass) method, a COF (Chip On Film) method, or the like. indicates As the IC 712, for example, an IC having a scanning line driving circuit or a signal line driving circuit can be used. FIG. 8A shows a structure in which an IC having a signal line driver circuit is used as the IC 712 and a scanning line driver circuit is used as the circuit 704. FIG.

[0384] A wiring 706 has a function of supplying signals and power to the display area 701 and the circuit 704 . The signal and power are input to wiring 706 from the outside via FPC (Flexible Printed Circuit) 713 or input to wiring 706 from IC 712 . Note that the device 720 may be configured without an IC. Also, the IC may be mounted on the FPC by the COF method or the like.

[0385] FIG. 8B shows a pixel 703(i,j) and a pixel 703(i+1,j) in the display area 701. FIG. In other words, the pixel 703(i,j) can have a configuration in which a plurality of types of sub-pixels having light-emitting devices that emit light of different colors are provided. Alternatively, in addition to the above, a structure including a plurality of sub-pixels having light-emitting devices that emit light of the same color can also be used. For example, a pixel can be configured to have three types of sub-pixels. The three sub-pixels are red (R), green (G), and blue (B) sub-pixels, and yellow (Y), cyan (C), and magenta (M) sub-pixels. etc. Alternatively, the pixel can be configured to have four types of sub-pixels. Examples of the four sub-pixels include R, G, B, and white (W) sub-pixels and four R, G, B, and Y sub-pixels. Specifically, a pixel 703 ( i, j).

[0386] Also, the sub-pixel may be configured to have a light-receiving device in addition to the light-emitting device. Note that in the case of a configuration having a light receiving device in a sub-pixel, the device 720 is also referred to as a light receiving and emitting device.

[0387] Pixel 703(i,j) shown in FIGS. 8(C)-8(F) shows an example of various layouts including sub-pixel 702PS(i,j) having a light receiving device. Note that the pixel arrangement shown in FIG. 8C is a stripe arrangement, and the pixel arrangement shown in FIG. 8D is a matrix arrangement. In the pixel arrangement shown in FIG. 8(E), three sub-pixels (sub-pixel R, sub-pixel G, and sub-pixel PS) are vertically arranged next to one sub-pixel (sub-pixel B). configuration. In addition, the arrangement of pixels shown in FIG. 8(F) has vertically elongated sub-pixels G, sub-pixels B, and sub-pixels R, which are arranged horizontally. are arranged side by side. Although the wavelength of light detected by the sub-pixel 702PS(i,j) is not particularly limited, the light-receiving devices included in the sub-pixel 702PS(i,j) include the sub-pixel 702R(i,j), the sub-pixel 702G(i ,j), subpixel 702B(i,j), or subpixel 702IR(i,j). For example, it is preferable to detect one or more of light in wavelength ranges such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red, and light in an infrared wavelength range.

[0388] Further, as shown in FIG. 8(F), a sub-pixel 702IR(i,j) that emits infrared rays may be added to the above set as a pixel 703(i,j). Specifically, a sub-pixel that emits light including light having a wavelength of 650 nm or more and 1000 nm or less may be used for the pixel 703(i, j).

[0389] Note that the arrangement of sub-pixels is not limited to the configurations shown in FIGS. 8B to 8F, and various methods can be applied. Sub-pixel arrangements include, for example, a stripe arrangement, an S-stripe arrangement, a matrix arrangement, a delta arrangement, a Bayer arrangement, and a pentile arrangement.

[0390] Examples of top surface shapes of sub-pixels include triangles, quadrilaterals (including rectangles and squares), polygons such as pentagons, polygons with rounded corners, ellipses, and circles. The top surface shape of the sub-pixel here corresponds to the top surface shape of the light emitting region of the light emitting device.

[0391] Furthermore, in the case where a pixel has a light receiving device as well as a light emitting device, the pixel has a light receiving function, so that it is possible to detect contact or proximity of an object while displaying an image. For example, not only can an image be displayed by all the sub-pixels of the light-emitting device, but also some sub-pixels can emit light as a light source and an image can be displayed by the remaining sub-pixels.

[0392] Note that the light receiving area of ​​the sub-pixel 702PS(i,j) is preferably smaller than the light emitting area of ​​the other sub-pixels. The smaller the light-receiving area, the narrower the imaging range, which makes it possible to suppress the blurring of the imaging result and improve the resolution. Therefore, by using the sub-pixel 702PS(i,j), high-definition or high-resolution imaging can be performed. For example, the sub-pixels 702PS(i,j) can be used to capture images for personal authentication using fingerprints, palmprints, irises, pulse shapes (including vein shapes and artery shapes), faces, and the like.

[0393] Also, the sub-pixel 702PS(i, j) can be used for a touch sensor (also called a direct touch sensor) or a near-touch sensor (also called a hover sensor, hover touch sensor, non-contact sensor, or touchless sensor). For example, subpixel 702PS(i,j) preferably detects infrared light. This enables touch detection even in dark places.

[0394] Here, a touch sensor or near-touch sensor can detect the proximity or contact of an object (such as a finger, hand, or pen). A touch sensor can detect an object by direct contact between the light emitting / receiving device and the object. In addition, the near-touch sensor can detect the object even if the object does not touch the light emitting / receiving device. For example, it is preferable that the light emitting / receiving device can detect the object when the distance between the light emitting / receiving device and the object is 0.1 mm or more and 300 mm or less, preferably 3 mm or more and 50 mm or less. With this configuration, the light emitting / receiving device can be operated without direct contact with the object, in other words, the light emitting / receiving device can be operated without contact (touchless). With the above configuration, the risk of staining or scratching the light emitting / receiving device can be reduced, or the object can come into direct contact with dirt (for example, dust, bacteria, or viruses) adhering to the light emitting / receiving device. It is possible to operate the light emitting / receiving device without having to

[0395] Note that the sub-pixels 702PS(i,j) are preferably provided in all the pixels included in the light emitting / receiving device in order to perform high-definition imaging. On the other hand, when the sub-pixel 702PS(i,j) is used for a touch sensor or a near-touch sensor, high accuracy is not required compared to the case of imaging a fingerprint, etc. pixels. By making the number of sub-pixels 702PS(i,j) included in the light emitting / receiving device smaller than the number of sub-pixels 702R(i,j), etc., the detection speed can be increased.

[0396] Next, an example of a pixel circuit of a sub-pixel having a light emitting device will be described with reference to FIG. 9(A). A pixel circuit 530 illustrated in FIG. 9A includes a light-emitting device (EL) 550, a transistor M15, a transistor M16, a transistor M17, and a capacitor C3. A light-emitting diode can be used as the light-emitting device 550 . In particular, it is preferable to use the light emitting device described in Embodiment 2 as light emitting device 550 .

[0397] In FIG. 9A, the transistor M15 has a gate electrically connected to the wiring VG, one of the source and the drain electrically connected to the wiring VS, and the other of the source and the drain connected to one of the capacitors C3. It is electrically connected to the electrode and the gate of transistor M16. One of the source and drain of transistor M16 is electrically connected to line V4, and the other is electrically connected to the anode of light-emitting device 550 and one of the source and drain of transistor M17. The transistor M17 has a gate electrically connected to the wiring MS and the other of the source and the drain electrically connected to the wiring OUT2. A cathode of the light emitting device 550 is electrically connected to the wiring V5.

[0398] A constant potential is supplied to each of the wiring V4 and the wiring V5. The anode side of light emitting device 550 can be at a higher potential and the cathode side can be at a lower potential than the anode side. The transistor M15 is controlled by a signal supplied to the wiring VG and functions as a selection transistor for controlling the selection state of the pixel circuit 530. FIG. Transistor M16 also functions as a drive transistor that controls the current flowing through light emitting device 550 according to the potential supplied to its gate. When the transistor M15 is on, the potential supplied to the wiring VS is supplied to the gate of the transistor M16, and the light emission luminance of the light emitting device 550 can be controlled according to the potential. The transistor M17 is controlled by a signal supplied to the wiring MS, and has a function of outputting the potential between the transistor M16 and the light emitting device 550 to the outside through the wiring OUT2.

[0399] Note that the transistor M15, the transistor M16, and the transistor M17 included in the pixel circuit 530 in FIG. 9A and the transistor M11, the transistor M12, the transistor M13, and the transistor M14 included in the pixel circuit 531 in FIG. It is preferable to use a transistor using a metal oxide (oxide semiconductor) for a semiconductor layer in which a channel is formed.

[0400] A transistor using a metal oxide, which has a wider bandgap and a lower carrier density than silicon, can achieve extremely low off-state current. Therefore, the small off-state current can hold charge accumulated in the capacitor connected in series with the transistor for a long time. Therefore, it is preferable to use a transistor including an oxide semiconductor, particularly for the transistor M11, the transistor M12, and the transistor M15 which are connected in series to the capacitor C2 or the capacitor C3. Further, by using a transistor including an oxide semiconductor for other transistors, the manufacturing cost can be reduced.

[0401] Alternatively, transistors in which silicon is used as a semiconductor in which a channel is formed can be used for the transistors M11 to M17. In particular, it is preferable to use highly crystalline silicon such as single crystal silicon or polycrystalline silicon because high field-effect mobility can be achieved and high-speed operation is possible.

[0402] Alternatively, at least one of the transistors M11 to M17 may be formed using an oxide semiconductor, and the rest may be formed using silicon.

[0403] Next, an example of a pixel circuit of a sub-pixel having a light receiving device will be described with reference to FIG. 9(B). A pixel circuit 531 illustrated in FIG. 9B includes a light receiving device (PD) 560, a transistor M11, a transistor M12, a transistor M13, a transistor M14, and a capacitor C2. Here, an example using a photodiode as the light receiving device (PD) 560 is shown.

[0404] In FIG. 9B, a light receiving device (PD) 560 has an anode electrically connected to the wiring V1 and a cathode electrically connected to either the source or the drain of the transistor M11. The transistor M11 has its gate electrically connected to the wiring TX, and the other of its source and drain electrically connected to one electrode of the capacitor C2, one of the source and drain of the transistor M12, and the gate of the transistor M13. The transistor M12 has a gate electrically connected to the wiring RES and the other of the source and the drain electrically connected to the wiring V2. The transistor M13 has one of its source and drain electrically connected to the wiring V3, and the other of its source and drain electrically connected to one of its source and drain of the transistor M14. The transistor M14 has a gate electrically connected to the wiring SE1 and the other of the source and the drain electrically connected to the wiring OUT1.

[0405] A constant potential is supplied to each of the wiring V1, the wiring V2, and the wiring V3. When the light receiving device (PD) 560 is driven with a reverse bias, the wiring V2 is supplied with a higher potential than the wiring V1. The transistor M12 is controlled by a signal supplied to the wiring RES, and has a function of resetting the potential of the node connected to the gate of the transistor M13 to the potential supplied to the wiring V2. The transistor M11 is controlled by a signal supplied to the wiring TX, and has a function of controlling the timing at which the potential of the node changes according to the current flowing through the light receiving device (PD) 560. FIG. The transistor M13 functions as an amplifying transistor that outputs according to the potential of the node. The transistor M14 is controlled by a signal supplied to the wiring SE1, and functions as a selection transistor for reading an output corresponding to the potential of the node with an external circuit connected to the wiring OUT1.

[0406] Note that although the transistors are shown as n-channel transistors in FIGS. 9A and 9B, p-channel transistors can also be used.

[0407] A transistor included in the pixel circuit 530 and a transistor included in the pixel circuit 531 are preferably formed side by side over the same substrate. In particular, it is preferable that the transistors included in the pixel circuit 530 and the transistors included in the pixel circuit 531 are mixed in one region and arranged periodically.

[0408] In addition, one or a plurality of layers each having one or both of a transistor and a capacitor are preferably provided at positions overlapping with the light receiving device (PD) 560 or the light emitting device (EL) 550 . As a result, the effective area occupied by each pixel circuit can be reduced, and a high-definition light receiving section or display section can be realized.

[0409] Next, FIG. 9C shows an example of a specific structure of a transistor that can be applied to the pixel circuit described in FIGS. 9A and 9B. Note that as the transistor, a bottom-gate transistor, a top-gate transistor, or the like can be used as appropriate.

[0410] A transistor illustrated in FIG. 9C includes a semiconductor film 508, a conductive film 504, an insulating film 506, a conductive film 512A, and a conductive film 512B. A transistor is formed, for example, on the insulating film 501C. The transistor also includes an insulating film 516 (an insulating film 516A and an insulating film 516B) and an insulating film 518. FIG.

[0411] The semiconductor film 508 has a region 508A electrically connected to the conductive film 512A and a region 508B electrically connected to the conductive film 512B. Semiconductor film 508 has a region 508C between regions 508A and 508B.

[0412] The conductive film 504 has a region overlapping with the region 508C, and the conductive film 504 functions as a gate electrode.

[0413] The insulating film 506 has a region sandwiched between the semiconductor film 508 and the conductive film 504 . The insulating film 506 functions as a first gate insulating film.

[0414] The conductive film 512A has one of the function of the source electrode and the function of the drain electrode, and the conductive film 512B has the other of the function of the source electrode and the function of the drain electrode.

[0415] Also, the conductive film 524 can be used for a transistor. The conductive film 524 has a region that sandwiches the semiconductor film 508 with the conductive film 504 . The conductive film 524 functions as a second gate electrode. The insulating film 501D is sandwiched between the semiconductor film 508 and the conductive film 524 and functions as a second gate insulating film.

[0416] The insulating film 516 functions as a protective film covering the semiconductor film 508, for example. Examples of the insulating film 516 include a silicon oxide film, a silicon oxynitride film, a silicon nitride oxide film, a silicon nitride film, an aluminum oxide film, a hafnium oxide film, an yttrium oxide film, a zirconium oxide film, and a gallium oxide film. , a tantalum oxide film, a magnesium oxide film, a lanthanum oxide film, a cerium oxide film, or a neodymium oxide film can be used.

[0417] For the insulating film 518, a material having a function of suppressing diffusion of oxygen, hydrogen, water, alkali metals, alkaline earth metals, or the like is preferably used. Specifically, as the insulating film 518, for example, silicon nitride, silicon oxynitride, aluminum nitride, aluminum oxynitride, or the like can be used. Further, the number of oxygen atoms and the number of nitrogen atoms contained in each of silicon oxynitride and aluminum oxynitride are preferably larger than that of nitrogen atoms.

[0418] Note that a semiconductor film used for a driver circuit transistor can be formed in the step of forming the semiconductor film used for the pixel circuit transistor. For example, a semiconductor film having the same composition as a semiconductor film used for a transistor in a pixel circuit can be used for a driver circuit.

[0419] In addition, the semiconductor film 508 includes, for example, indium and M (M is gallium, aluminum, silicon, boron, yttrium, tin, copper, vanadium, beryllium, titanium, iron, nickel, germanium, zirconium, molybdenum, lanthanum, cerium , neodymium, hafnium, tantalum, tungsten, and magnesium) and zinc. In particular, M is preferably one or more selected from aluminum, gallium, yttrium, and tin.

[0420] In particular, an oxide containing indium (In), gallium (Ga), and zinc (Zn) (also referred to as IGZO) is preferably used for the semiconductor film 508 . Alternatively, an oxide containing indium, tin, and zinc is preferably used. Alternatively, oxides containing indium, gallium, tin, and zinc are preferably used. Alternatively, an oxide containing indium (In), aluminum (Al), and zinc (Zn) (also referred to as IAZO) is preferably used. Alternatively, an oxide containing indium (In), aluminum (Al), gallium (Ga), and zinc (Zn) (also referred to as IAGZO) is preferably used.

[0421] When the semiconductor film is an In--M--Zn oxide, the atomic ratio of In in the In--M--Zn oxide is preferably equal to or higher than the atomic ratio of M. The atomic number ratio of the metal elements of such In-M-Zn oxide is In:M:Zn=1:1:1 or its vicinity composition, In:M:Zn=1:1:1.2 or its vicinity. composition, In:M:Zn=1:3:2 or its neighborhood, In:M:Zn=1:3:4 or its neighborhood, In:M:Zn=2:1:3 or its neighborhood Nearby composition, In:M:Zn=3:1:2 or its near composition, In:M:Zn=4:2:3 or its near composition, In:M:Zn=4:2:4.1 or Composition in the vicinity thereof, In:M:Zn=5:1:3 or composition in the vicinity thereof, In:M:Zn=5:1:6 or composition in the vicinity thereof, In:M:Zn=5:1:7 or a composition in the vicinity thereof, In:M:Zn=5:1:8 or a composition in the vicinity thereof, In:M:Zn=6:1:6 or a composition in the vicinity thereof, In:M:Zn=5:2: 5 or a composition in the vicinity thereof, and the like. The composition in the neighborhood includes the range of ±30% of the desired atomic number ratio.

[0422] For example, when describing a composition with an atomic number ratio of In:Ga:Zn=4:2:3 or in the vicinity thereof, when In is 4, Ga is 1 or more and 3 or less, and Zn is 2 or more and 4 or less. Including if there is. In addition, when describing a composition with an atomic ratio of In:Ga:Zn=5:1:6 or in the vicinity thereof, where In is 5, Ga is greater than 0.1 and 2 or less, and Zn is 5 or more and 7 Including when: In addition, when the atomic number ratio is In:Ga:Zn=1:1:1 or a composition in the vicinity thereof, when In is 1, Ga is greater than 0.1 and 2 or less, and Zn is greater than 0.1. Including when it is 2 or less.

[0423] The crystallinity of the semiconductor material used for the transistor is not particularly limited, either an amorphous semiconductor or a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a partially crystalline region). may be used. It is preferable to use a crystalline semiconductor because deterioration of transistor characteristics can be suppressed.

[0424] A semiconductor layer of a transistor preferably includes a metal oxide (also referred to as an oxide semiconductor). Note that examples of oxide semiconductors having crystallinity include CAAC (c-axis-aligned crystalline)-OS, nc (nanocrystalline)-OS, and the like.

[0425] Alternatively, a transistor using silicon for a channel formation region (Si transistor) may be used. Examples of silicon include single crystal silicon (single crystal Si), polycrystalline silicon, amorphous silicon, and the like. In particular, a transistor including low temperature polysilicon (LTPS) in a semiconductor layer (hereinafter also referred to as an LTPS transistor) can be used. The LTPS transistor has high field effect mobility and good frequency characteristics.

[0426] By applying a Si transistor such as an LTPS transistor, a circuit that needs to be driven at a high frequency (for example, a source driver circuit) can be built on the same substrate as the display section. This makes it possible to simplify the external circuit mounted on the light-emitting device and reduce the component cost and the mounting cost.

[0427] OS transistors have extremely high field-effect mobility compared to transistors using amorphous silicon. In addition, an OS transistor has extremely low source-drain leakage current (hereinafter also referred to as an off-state current) in an off state, and can retain charge accumulated in a capacitor connected in series with the transistor for a long time. is possible. Further, by using an OS transistor, power consumption of the light-emitting device can be reduced.

[0428] In addition, the off current value of the OS transistor per 1 µm channel width at room temperature is 1aA (1 × 10 -18 A) or less, 1zA (1×10 -21 A) or less, or 1yA (1 x 10 -24 A) can be: Note that the off-current value of a Si transistor per 1 μm channel width at room temperature is 1 fA (1×10 -15 A) 1 pA (1 x 10 -12 A) below. Therefore, it can be said that the off-current of the OS transistor is about ten orders of magnitude lower than the off-current of the Si transistor.

[0429] Further, in order to increase the light emission luminance of the light emitting device included in the pixel circuit, it is necessary to increase the amount of current flowing through the light emitting device. For that purpose, it is necessary to increase the source-drain voltage of the drive transistor included in the pixel circuit. Since the OS transistor has a higher breakdown voltage between the source and the drain than the Si transistor, a high voltage can be applied between the source and the drain of the OS transistor. Therefore, by using an OS transistor as the driving transistor included in the pixel circuit, it is possible to increase the amount of current flowing through the light emitting device and increase the light emission luminance of the light emitting device.

[0430] Further, when the transistor operates in the saturation region, the OS transistor can reduce the change in the current between the source and the drain with respect to the change in the voltage between the gate and the source compared to the Si transistor. Therefore, by using an OS transistor as the drive transistor in the pixel circuit, the current flowing between the source and the drain can be finely determined according to the change in the voltage between the gate and the source. can be controlled. Therefore, the number of gradations in the pixel circuit can be increased.

[0431] In terms of the saturation characteristics of the current that flows when the transistor operates in the saturation region, the OS transistor flows a more stable current (saturation current) than the Si transistor, even when the source-drain voltage gradually increases. be able to. Therefore, by using the OS transistor as the driving transistor, a stable current can be supplied to the light-emitting device even if the current-voltage characteristics of the light-emitting device vary. That is, when the OS transistor operates in the saturation region, even if the voltage between the source and the drain is increased, the current between the source and the drain hardly changes, so that the luminance of the light emitting device can be stabilized.

[0432] As mentioned above, by using an OS transistor as the drive transistor in the pixel circuit, we are able to achieve various functions such as suppression of black floating, increase in emission brightness, multi-gradation, and suppression of variation in light-emitting devices. can be planned.

[0433] Alternatively, a semiconductor film used for a transistor in a driver circuit can be formed in the same process as a semiconductor film used for a transistor in a pixel circuit. Alternatively, the driver circuit can be formed over the same substrate as the substrate forming the pixel circuit. Alternatively, the number of parts constituting the electronic device can be reduced.

[0434] By using LTPS transistors for some of the transistors included in the pixel circuit and using OS transistors for other transistors, a light-emitting device with low power consumption and high driving capability can be realized. As a more preferable example, an OS transistor is preferably used as a transistor that functions as a switch for controlling conduction / non-conduction between wirings, and an LTPS transistor is preferably used as a transistor that controls current. Note that a configuration in which both the LTPS transistor and the OS transistor are combined is sometimes called LTPO. By using LTPO, a display panel with low power consumption and high driving capability can be realized.

[0435] For example, one of the transistors provided in the pixel circuit functions as a transistor for controlling current flowing through the light emitting device and can also be called a driving transistor. One of the source and drain of the driving transistor is electrically connected to the pixel electrode of the light emitting device. An LTPS transistor is preferably used as the driving transistor. This makes it possible to increase the current flowing through the light emitting device in the pixel circuit.

[0436] On the other hand, the other transistor provided in the pixel circuit functions as a switch for controlling selection / non-selection of the pixel and can also be called a selection transistor. The gate of the selection transistor is electrically connected to the gate line, and one of the source and the drain is electrically connected to the source line (signal line). An OS transistor is preferably used as the selection transistor. As a result, pixel gradation can be maintained even if the frame frequency is significantly reduced (for example, 1 fps or less), so power consumption can be reduced by stopping the driver when displaying a still image. can.

[0437] When an oxide semiconductor is used for the semiconductor film, the device 720 uses the oxide semiconductor for the semiconductor film and has a light-emitting device with an MML (metal maskless) structure. With this structure, leakage current that can flow through the transistor and leakage current that can flow between adjacent light-emitting devices (also referred to as lateral leakage current, side leakage current, or the like) can be extremely reduced. Further, with the above structure, when an image is displayed on the display device, an observer can observe any one or more of sharpness of the image, sharpness of the image, high saturation, and high contrast ratio. In addition, by adopting a configuration in which the leakage current that can flow through the transistor and the horizontal leakage current between light-emitting devices are extremely low, light leakage that can occur during black display (so-called black floating) is minimized (also known as pure black display). can be

[0438] In particular, among light-emitting devices having the MML structure, by applying the SBS structure shown above, a layer provided between light-emitting devices (for example, an organic layer commonly used between light-emitting devices, also referred to as a common layer) can be Since the structure is divided, a display with no side leakage or very little side leakage can be obtained.

[0439] Further, the structure of the transistor used in the display panel may be selected as appropriate according to the size of the screen of the display panel. For example, when a single-crystal Si transistor is used as a display panel transistor, it can be applied to a screen size with a diagonal size of 0.1 inch or more and 3 inches or less. Further, when LTPS transistors are used as transistors of the display panel, they can be applied to a screen size with a diagonal size of 0.1 inch or more and 30 inches or less, preferably 1 inch or more and 30 inches or less. Also, when LTPO (combination of LTPS transistors and OS transistors) is used for the display panel, the diagonal size should be 0.1 inch or more and 50 inches or less, preferably 1 inch or more and 50 inches or less. can be done. Further, when an OS transistor is used as a transistor of a display panel, it can be applied to a screen size with a diagonal size of 0.1 inch or more and 200 inches or less, preferably 50 inches or more and 100 inches or less.

[0440] It should be noted that it is very difficult to increase the size of a single-crystal Si transistor compared to the size of a single-crystal Si substrate. In addition, since the LTPS transistor uses a laser crystallizer in the manufacturing process, it is difficult to cope with an increase in size (typically, a screen size exceeding 30 inches in diagonal size). On the other hand, OS transistors are relatively large in area because they are not restricted to the use of laser crystallization equipment in the manufacturing process, or they can be manufactured at relatively low process temperatures (typically 450°C or less). (Typically, it is possible to correspond to a display panel of 50 inches or more and 100 inches or less in diagonal size). In addition, LTPO is applied to the size of the display panel in the area between the case of using LTPS transistors and the case of using OS transistors (typically, 1 inch or more and 50 inches or less in diagonal size). becomes possible.

[0441] Next, a cross-sectional view of the light emitting / receiving device is shown. FIG. 10 shows a cross-sectional view of the light emitting / receiving device shown in FIG. 8(A).

[0442] The cross-sectional view of FIG. 10 shows a cross-sectional view when a portion of the region including the FPC 713 and the wiring 706 and a portion of the display region 701 including the pixel 703(i,j) are cut.

[0443] In FIG. 10, the light emitting / receiving device 700 has a functional layer 520 between a first substrate 510 and a second substrate 770 . The functional layer 520 includes the transistors (M11, M12, M13, M14, M15, M16, M17) and capacitive elements (C2, C3) described in FIG. VG, V1, V2, V3, V4, V5), etc. Although FIG. 10 shows the functional layer 520 including the pixel circuit 530X(i,j), the pixel circuit 530S(i,j), and the circuit GD, it is not limited to this.

[0444] In addition, the pixel circuits formed on the functional layer 520 (for example, the pixel circuits 530X(i,j) and pixel circuits 530S(i,j) shown in FIG. 10) correspond to the light emitting device and the light receiving device formed on the functional layer 520. It is electrically connected to a device (for example, the light emitting device 550X(i,j) and the light receiving device 550S(i,j) shown in FIG. 10). Specifically, the light emitting device 550X(i,j) is electrically connected to the pixel circuit 530X(i,j) via the wiring 591X, and the light receiving device 550S(i,j) is electrically connected to the pixel circuit via the wiring 591S. It is electrically connected to 530S(i,j). An insulating layer 705 is provided over the functional layer 520, the light emitting device, and the light receiving device, and the insulating layer 705 has a function of bonding the second substrate 770 and the functional layer 520 together.

[0445] Note that a substrate provided with touch sensors in a matrix can be used as the second substrate 770 . For example, a substrate with capacitive touch sensors or optical touch sensors can be used for the second substrate 770 . Accordingly, the light emitting and receiving device of one embodiment of the present invention can be used as a touch panel.

[0446] Note that the structure described in this embodiment can be used in combination with any of the structures described in other embodiments as appropriate.

[0447] (Embodiment 5) In this embodiment, structures of electronic devices of one embodiment of the present invention will be described with reference to FIGS.

[0448] 11A to 13B are diagrams illustrating structures of electronic devices of one embodiment of the present invention. FIG. 11A is a block diagram of an electronic device, and FIGS. 11B to 11E are perspective views illustrating the configuration of the electronic device. 12(A) to 12(E) are perspective views illustrating the configuration of the electronic device. 13(A) and 13(B) are perspective views illustrating the configuration of the electronic device.

[0449] An electronic device 5200B described in this embodiment includes an arithmetic device 5210 and an input / output device 5220 (see FIG. 11A).

[0450] The computing device 5210 has a function of being supplied with operation information, and has a function of supplying image information based on the operation information.

[0451] The input / output device 5220 has a display unit 5230, an input unit 5240, a detection unit 5250, a communication unit 5290, a function of supplying operation information, and a function of receiving image information. Also, the input / output device 5220 has a function of supplying detection information, a function of supplying communication information, and a function of being supplied with communication information.

[0452] The input unit 5240 has a function of supplying operation information. For example, the input unit 5240 supplies operation information based on the user's operation of the electronic device 5200B.

[0453] Specifically, a keyboard, hardware buttons, pointing device, touch sensor, illuminance sensor, imaging device, voice input device, line-of-sight input device, posture detection device, or the like can be used for the input unit 5240 .

[0454] The display portion 5230 has a display panel and a function of displaying image information. For example, the display panel described in Embodiment 3 can be used for the display portion 5230. FIG.

[0455] The detection unit 5250 has a function of supplying detection information. For example, it has a function of detecting the surrounding environment in which the electronic device is used and supplying it as detection information.

[0456] Specifically, an illuminance sensor, an imaging device, a posture detection device, a pressure sensor, a motion sensor, or the like can be used for the detection unit 5250.

[0457] The communication unit 5290 has a function of receiving and supplying communication information. For example, it has a function of connecting to other electronic devices or communication networks by wireless communication or wired communication. Specifically, it has functions such as wireless local communication, telephone communication, and short-range wireless communication.

[0458] FIG. 11B shows an electronic device having an outer shape along a cylindrical pillar or the like. One example is digital signage. The display panel which is one embodiment of the present invention can be applied to the display portion 5230. Note that a function of changing the display method according to the illuminance of the usage environment may be provided. It also has a function of detecting the presence of a person and changing the display content. This allows it to be installed, for example, on a building pillar. Alternatively, advertisements, guidance, or the like can be displayed.

[0459] FIG. 11(C) shows an electronic device having a function of generating image information based on the trajectory of the pointer used by the user. Examples include electronic blackboards, electronic bulletin boards, electronic signboards, and the like. Specifically, a display panel with a diagonal length of 20 inches or more, preferably 40 inches or more, more preferably 55 inches or more can be used. Alternatively, a plurality of display panels can be arranged and used as one display area. Alternatively, a plurality of display panels can be arranged and used for a multi-screen.

[0460] FIG. 11D shows an electronic device that can receive information from another device and display it on the display portion 5230. FIG. One example is wearable electronic devices. Specifically, several options can be displayed or the user can select some of the options and send them back to the source of the information. Alternatively, for example, it has a function of changing the display method according to the illuminance of the usage environment. Thereby, for example, the power consumption of the wearable electronic device can be reduced. Alternatively, for example, an image can be displayed on a wearable electronic device so that it can be suitably used even in an environment with strong external light, such as outdoors on a sunny day.

[0461] FIG. 11E shows an electronic device having a display portion 5230 with a curved surface gently curved along the side surface of the housing. One example is a mobile phone. Note that the display portion 5230 includes a display panel, and the display panel has a function of displaying on the front, side, top, and back, for example. This allows, for example, information to be displayed not only on the front of the mobile phone, but also on the sides, top and back.

[0462] FIG. 12A shows an electronic device that can receive information from the Internet and display it on the display portion 5230. FIG. A smart phone etc. are mentioned as an example. For example, the created message can be confirmed on the display unit 5230. Or you can send the composed message to other devices. Alternatively, for example, it has a function of changing the display method according to the illuminance of the usage environment. As a result, power consumption of the smartphone can be reduced. Alternatively, for example, the image can be displayed on the smartphone so that it can be suitably used even in an environment with strong external light, such as outdoors on a sunny day.

[0463] FIG. 12B shows an electronic device whose input unit 5240 can be a remote controller. An example is a television system. Alternatively, information can be received from a broadcasting station or the Internet and displayed on the display unit 5230, for example. Alternatively, the detection unit 5250 can be used to photograph the user. Alternatively, the user's image can be transmitted. Alternatively, the user's viewing history can be acquired and provided to the cloud service. Alternatively, recommendation information can be acquired from a cloud service and displayed on the display unit 5230 . Alternatively, a program or video can be displayed based on the recommendation information. Alternatively, for example, it has a function of changing the display method according to the illuminance of the usage environment. As a result, images can be displayed on the television system so that it can be suitably used even when the strong external light that shines indoors on a sunny day strikes.

[0464] FIG. 12C shows an electronic device capable of receiving teaching materials from the Internet and displaying them on the display portion 5230. FIG. One example is a tablet computer. Alternatively, the input section 5240 can be used to enter a report and send it to the Internet. Alternatively, the correction result or evaluation of the report can be acquired from the cloud service and displayed on the display unit 5230. Alternatively, suitable teaching materials can be selected and displayed based on the evaluation.

[0465] For example, an image signal can be received from another electronic device and displayed on the display portion 5230. Alternatively, the display portion 5230 can be used as a sub-display by leaning it against a stand or the like. As a result, images can be displayed on the tablet computer so that the tablet computer can be suitably used even in an environment with strong external light, such as outdoors on a sunny day.

[0466] FIG. 12D shows an electronic device having multiple display portions 5230. FIG. An example is a digital camera. For example, an image can be displayed on the display unit 5230 while the detection unit 5250 captures an image. Alternatively, the captured image can be displayed on the detection unit. Alternatively, the input unit 5240 can be used to decorate the captured video. Or you can attach a message to the captured video. Or you can send it to the internet. Alternatively, it has a function of changing the shooting conditions according to the illuminance of the usage environment. As a result, the subject can be displayed on the digital camera so that it can be conveniently viewed even in an environment with strong external light, such as outdoors on a sunny day.

[0467] FIG. 12E shows an electronic device that can control the other electronic device by using another electronic device as a slave and using the electronic device of this embodiment as a master. One example is a portable personal computer. For example, part of the image information can be displayed on the display unit 5230, and the other part of the image information can be displayed on the display unit of another electronic device. Alternatively, an image signal can be supplied. Alternatively, the communication unit 5290 can be used to acquire information to be written from an input unit of another electronic device. As a result, a wide display area can be used, for example, by using a portable personal computer.

[0468] FIG. 13A shows an electronic device having a detection unit 5250 that detects acceleration or orientation. An example is a goggle-type electronic device. Alternatively, the sensing unit 5250 can provide information regarding the location of the user or the direction the user is facing. Alternatively, the electronic device can generate image information for the right eye and image information for the left eye based on the position of the user or the direction the user is facing. Alternatively, the display unit 5230 has a display area for the right eye and a display area for the left eye. As a result, for example, an image of a virtual reality space that provides a sense of immersion can be displayed on a goggle-type electronic device.

[0469] FIG. 13B shows an electronic device including an imaging device and a detection unit 5250 that detects acceleration or orientation. An example is a glasses-type electronic device. Alternatively, the sensing unit 5250 can provide information regarding the location of the user or the direction the user is facing. Alternatively, the electronic device can generate image information based on the location of the user or the direction the user is facing. As a result, for example, it is possible to attach information to a real landscape and display it. Alternatively, an image of the augmented reality space can be displayed on a glasses-type electronic device.

[0470] Note that this embodiment can be combined with any of the other embodiments described in this specification as appropriate.

[0471] (Embodiment 6) In this embodiment, a configuration using the light-emitting device described in Embodiment 2 as a lighting device will be described with reference to FIG. Note that FIG. 14(A) is a cross-sectional view taken along line ef in the top view of the lighting device shown in FIG. 14(B).

[0472] In the lighting device according to the present embodiment, a first electrode 401 is formed on a translucent substrate 400 which is a support. First electrode 401 corresponds to first electrode 101 in the second embodiment. When light is extracted from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

[0473] A pad 412 is formed on the substrate 400 for supplying voltage to the second electrode 404 .

[0474] An EL layer 403 is formed over the first electrode 401 . EL layer 403 corresponds to the configuration of EL layer 103 in the second embodiment. In addition, please refer to the said description about these structures.

[0475] A second electrode 404 is formed over the EL layer 403 . Second electrode 404 corresponds to second electrode 102 in the second embodiment. When light emission is extracted from the first electrode 401 side, the second electrode 404 is made of a highly reflective material. A voltage is supplied to the second electrode 404 by connecting it to the pad 412 .

[0476] As described above, the lighting device described in this embodiment includes the light-emitting device including the first electrode 401, the EL layer 403, and the second electrode 404. FIG. Since the light-emitting device has high emission efficiency, the lighting device in this embodiment can have low power consumption.

[0477] The substrate 400 on which the light emitting device having the above configuration is formed and the sealing substrate 407 are fixed and sealed using sealing materials (405, 406) to complete the lighting device. Either one of the sealing materials 405 and 406 may be used. A desiccant can also be mixed in the inner sealing material 406 (not shown in FIG. 14(B)), which can absorb moisture, leading to improved reliability.

[0478] Further, by extending a part of the pad 412 and the first electrode 401 outside the sealing materials 405 and 406, they can be used as external input terminals. Moreover, an IC chip 420 or the like having a converter or the like mounted thereon may be provided thereon.

[0479] (Embodiment 7) In this embodiment, application examples of a lighting device manufactured using a light-emitting device that is one embodiment of the present invention or a light-emitting device that is a part thereof will be described with reference to FIGS.

[0480] It can be applied as a ceiling light 8001 as an indoor lighting device. The ceiling light 8001 includes a ceiling direct type and a ceiling embedded type. Note that such a lighting device is configured by combining a light emitting device with a housing and a cover. In addition, application to a cord pendant type (a cord hanging type from the ceiling) is also possible.

[0481] Also, the foot light 8002 can illuminate the floor surface to enhance the safety of the foot. For example, it is effective for use in bedrooms, stairs, corridors, and the like. In that case, the size and shape can be changed as appropriate according to the size and structure of the room. In addition, a stationary lighting device configured by combining a light emitting device and a support base is also possible.

[0482] Also, the sheet-shaped lighting 8003 is a thin sheet-shaped lighting device. Since it is attached to the wall, it does not take up much space and can be used for a wide range of purposes. In addition, it is easy to increase the area. In addition, it can also be used for a wall surface having a curved surface, a housing, or the like.

[0483] Also, a lighting device 8004 in which light from a light source is controlled only in a desired direction can be used.

[0484] The desk lamp 8005 includes a light source 8006, and as the light source 8006, a light-emitting device that is one embodiment of the present invention or a part thereof can be used.

[0485] In addition to the above, by applying the light-emitting device of one embodiment of the present invention or a light-emitting device that is part of the light-emitting device of the present invention to a part of furniture provided in a room, a lighting device having a function as furniture can be obtained. can do.

[0486] As described above, various lighting devices to which the light-emitting device is applied can be obtained. Note that these lighting devices are included in one embodiment of the present invention.

[0487] Further, the structure described in this embodiment can be combined with any of the structures described in other embodiments as appropriate.

[0488] (Embodiment 8) In this embodiment, a light-emitting device and a light-receiving device that can be applied to the light-receiving and emitting device that is one embodiment of the present invention will be described with reference to FIGS.

[0489] A schematic cross-sectional view of a light-emitting device 805a and a light-receiving device 805b included in a light-receiving and emitting device 810 of one embodiment of the present invention is shown in FIG.

[0490] The light emitting device 805a has a function of emitting light (hereinafter also referred to as a light emitting function). Light-emitting device 805a has electrode 801a, EL layer 803a, and electrode 802a. The light-emitting device 805a is preferably a light-emitting device (organic EL device) using the organic EL shown in the second embodiment. Therefore, EL layer 803a sandwiched between electrode 801a and electrode 802 has at least a light-emitting layer. The light-emitting layer has a light-emitting material. By applying a voltage between the electrodes 801a and 802, light is emitted from the EL layer 803a. The EL layer 803a has various layers such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier (hole or electron) block layer, and a charge generation layer in addition to the light emitting layer. may be

[0491] The light receiving device 805b has a function of detecting light (hereinafter also referred to as a light receiving function). For the light receiving device 805b, for example, a pn-type or pin-type photodiode can be used. Light-receiving device 805b has electrode 801b, light-receiving layer 803b, and electrode 802. FIG. Light-receiving layer 803b sandwiched between electrode 801b and electrode 802 has at least an active layer. Note that the light-receiving layer 803b includes various layers (hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, carrier (hole or electron) blocking layer, (charge generation layer, etc.) can also be used. The light-receiving device 805b functions as a photoelectric conversion device, and can generate electric charge by light incident on the light-receiving layer 803b and extract it as a current. At this time, a voltage may be applied between the electrode 801b and the electrode 802. FIG. The amount of charge generated is determined based on the amount of light incident on the light receiving layer 803b.

[0492] The light receiving device 805b has a function of detecting visible light. Light receiving device 805b is sensitive to visible light. More preferably, the light receiving device 805b has a function of detecting visible light and infrared light. The light receiving device 805b is preferably sensitive to visible light and infrared light.

[0493] Note that the blue (B) wavelength region in this specification and the like is 400 nm or more and less than 490 nm, and the blue (B) light has at least one emission spectrum peak in this wavelength region. Also, the wavelength region of green (G) is 490 nm or more and less than 580 nm, and green (G) light has at least one emission spectrum peak in this wavelength region. Also, the red (R) wavelength region is from 580 nm to less than 700 nm, and the red (R) light has at least one emission spectrum peak in this wavelength region. In this specification and the like, the wavelength region of visible light is 400 nm or more and less than 700 nm, and visible light has at least one emission spectrum peak in this wavelength region. Also, the infrared (IR) wavelength range is from 700 nm to less than 900 nm, and infrared (IR) light has at least one emission spectrum peak in this wavelength range.

[0494] The active layer of light receiving device 805b comprises a semiconductor. Examples of the semiconductor include inorganic semiconductors such as silicon, organic semiconductors including organic compounds, and the like. As the light receiving device 805b, it is preferable to use an organic semiconductor device (or an organic photodiode) containing an organic semiconductor in the active layer. Organic photodiodes can be easily made thinner, lighter, and larger, and have a high degree of freedom in shape and design, so that they can be applied to various display devices. Further, by using an organic semiconductor, the EL layer 803a of the light-emitting device 805a and the light-receiving layer 803b of the light-receiving device 805b can be formed by the same method (for example, vacuum deposition), and a common manufacturing apparatus can be used. can be used. Note that an organic compound that is one embodiment of the present invention can be used for the light-receiving layer 803b of the light-receiving device 805b.

[0495] The display device of one embodiment of the present invention can preferably use an organic EL device as the light-emitting device 805a and an organic photodiode as the light-receiving device 805b. An organic EL device and an organic photodiode can be formed on the same substrate. Therefore, an organic photodiode can be incorporated in a display device using an organic EL device. A display device which is one embodiment of the present invention has one or both of an imaging function and a sensing function in addition to a function of displaying an image.

[0496] Electrode 801a and electrode 801b are provided on the same plane. FIG. 16A shows a structure in which an electrode 801a and an electrode 801b are provided over a substrate 800. FIG. Note that the electrodes 801a and 801b can be formed, for example, by processing a conductive film formed over the substrate 800 into an island shape. That is, the electrodes 801a and 801b can be formed through the same process.

[0497] As the substrate 800, a substrate having heat resistance that can withstand formation of the light-emitting device 805a and the light-receiving device 805b can be used. When an insulating substrate is used as the substrate 800, a glass substrate, a quartz substrate, a sapphire substrate, a ceramic substrate, an organic resin substrate, or the like can be used. Alternatively, a semiconductor substrate such as a single crystal semiconductor substrate, a polycrystalline semiconductor substrate, a compound semiconductor substrate made of silicon germanium or the like, or an SOI substrate can be used.

[0498] In particular, as the substrate 800, it is preferable to use the above insulating substrate or semiconductor substrate on which a semiconductor circuit including a semiconductor element such as a transistor is formed. The semiconductor circuit preferably constitutes, for example, a pixel circuit, a gate line driving circuit (gate driver), a source line driving circuit (source driver), and the like. Further, in addition to the above, an arithmetic circuit, a memory circuit, and the like may be configured.

[0499] Further, the electrode 802 is an electrode made of a layer common to the light emitting device 805a and the light receiving device 805b. Among these electrodes, a conductive film that transmits visible light and infrared light is used for the electrode on the side from which light is emitted or from which light is incident. A conductive film that reflects visible light and infrared light is preferably used for the electrode on the side from which light is not emitted or incident.

[0500] The electrode 802 in the display device of one embodiment of the present invention functions as one electrode of each of the light-emitting device 805a and the light-receiving device 805b.

[0501] FIG. 16B shows the case where the electrode 801a of the light-emitting device 805a has a higher potential than the electrode 802. FIG. At this time, electrode 801a functions as the anode of light-emitting device 805a, and electrode 802 functions as the cathode. Also, the electrode 801b of the light receiving device 805b has a lower potential than the electrode 802. FIG. Note that in FIG. 16B, a circuit symbol for a light-emitting diode is shown on the left side of the light-emitting device 805a, and a circuit symbol for a photodiode is shown on the right side of the light-receiving device 805b, in order to make it easier to understand the direction of current flow. Also, the direction of flow of carriers (electrons and holes) is schematically indicated by arrows in each device.

[0502] In the structure shown in FIG. 16B, the electrode 801a is supplied with the first potential through the first wiring, the electrode 802 is supplied with the second potential through the second wiring, and the electrode 801b is supplied with the second potential through the second wiring. When the third potential is supplied through the third wiring, the magnitude relationship of each potential is first potential>second potential>third potential.

[0503] 16C shows the case where the electrode 801a of the light-emitting device 805a has a lower potential than the electrode 802. FIG. At this time, electrode 801a functions as a cathode of light emitting device 805a, and electrode 802 functions as an anode. Also, the electrode 801b of the light receiving device 805b has a lower potential than the electrode 802 and a higher potential than the electrode 801a. Note that in FIG. 16C, a circuit symbol for a light-emitting diode is shown on the left side of the light-emitting device 805a, and a circuit symbol for a photodiode is shown on the right side of the light-receiving device 805b, in order to make it easier to understand the direction of current flow. Also, the direction of flow of carriers (electrons and holes) is schematically indicated by arrows in each device.

[0504] In the structure shown in FIG. 16C, the electrode 801a is supplied with the first potential through the first wiring, the electrode 802 is supplied with the second potential through the second wiring, and the electrode 801b is supplied with the second potential through the second wiring. When the third potential is supplied through the third wiring, the magnitude relationship of each potential is second potential>third potential>first potential.

[0505] FIG. 17A shows a light emitting / receiving device 810A that is a modification of the light emitting / receiving device 810. FIG. Light emitting and receiving device 810A differs from light emitting and receiving device 810 in that it has common layer 806 and common layer 807 . Common layer 806 and common layer 807 in light emitting device 805a function as part of EL layer 803a. Also, in light receiving device 805b, common layer 806 and common layer 807 function as part of light receiving layer 803b. Common layer 806 also includes, for example, a hole injection layer and a hole transport layer. Common layer 807 also includes, for example, an electron transport layer and an electron injection layer.

[0506] By adopting a configuration having common layer 806 and common layer 807, the light receiving device can be built in without greatly increasing the number of separate coatings, and the light receiving and emitting device 810A can be manufactured with high throughput.

[0507] FIG. 17B shows a light emitting / receiving device 810B that is a modification of the light emitting / receiving device 810A. The light emitting / receiving device 810B differs from the light emitting / receiving device 810A in that the EL layer 803a has layers 806a and 807a, and the light receiving layer 803b has layers 806b and 807b. Layers 806a and 806b are each composed of different materials and include, for example, a hole injection layer and a hole transport layer. Note that the layers 806a and 806b may each be made of a common material. Also, layers 807a and 807b are each composed of different materials and include, for example, an electron-transporting layer and an electron-injecting layer. Layer 807a and layer 807b may each be composed of a common material.

[0508] By selecting optimal materials for layers 806a and 807a to construct light-emitting device 805a, and optimal materials for layers 806b and 807b to construct light-receiving device 805b, the light receiving and emitting In apparatus 810B, the performance of each of light emitting device 805a and light receiving device 805b can be enhanced.

[0509] The resolution of the light-receiving device 805b shown in this embodiment is 100 ppi or more, preferably 200 ppi or more, more preferably 300 ppi or more, more preferably 400 ppi or more, still more preferably 500 ppi or more, and 2000 ppi or less. or less, or 600ppi or less, etc. In particular, by arranging the light receiving device 805b with a resolution of 200 ppi or more and 600 ppi or less, preferably 300 ppi or more and 600 ppi or less, it can be suitably used for fingerprint imaging. When fingerprint authentication is performed using the display device of one embodiment of the present invention, by increasing the definition of the light-receiving device 805b, for example, minutia of the fingerprint can be extracted with high accuracy, and the accuracy of fingerprint authentication can be improved. can be enhanced. In addition, when the resolution is 500 ppi or more, it is preferable because it can conform to standards such as the US National Institute of Standards and Technology (NIST). Assuming that the resolution of the light receiving device is 500 ppi, the size of each pixel is 50.8 μm, which is sufficient to capture the width of a fingerprint (typically, 300 μm or more and 500 μm or less). I understand.

[0510] Further, the structure described in this embodiment can be combined with any of the structures described in other embodiments as appropriate.

Example

[0511] ≪Synthesis Example 1≫ In this example, 4,8-bis[3-(dibenzothiophen-4-yl-1,2,3,6,7,8,9-d 7 ) phenyl-2,4,6-d 3 ]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm-d 20 ) will be specifically described.

[0512] [formation]

[0513] <Step 1-1; 4-(3-bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 Synthesis of> Molybdenum pentachloride (V) (abbreviation: MoCl 5 ), 1.4 g (5.0 mmol) of deuterated toluene (abbreviation: toluene-d 8 ) and 3.4 g (10 mmol) of 4-(3-bromophenyl)dibenzothiophene were added, and the mixture was stirred at 100° C. for 8 hours under a nitrogen stream. After the reaction, toluene and 1.0 mol / L hydrochloric acid were added to the mixture in the flask, and the precipitated solid was removed by suction filtration. The filtrate was extracted with toluene, and the obtained organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil. The resulting oil was purified by silica gel column chromatography (hexane) to give the desired 4-(3-bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 (clear oil) was obtained in 2.3 g with a yield of 67%. The synthesis scheme of step 1-1 is shown in formula (a-1) below.

[0514] [formation]

[0515] The 4-(3-bromophenyl-2,4,6-d obtained in step 1-1 above 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 nuclear magnetic resonance spectroscopy ( 1 1 H-NMR) analysis results are shown below. again, 1 18(A) and 18(B) show 1 H-NMR charts.

[0516] 1 H-NMR.δ(CDCl 3 ,300MHz): 7.38-7.40(m,1H).

[0517] In FIG. 18(B), signals around δ = 7.68 ppm to 7.71 ppm and δ = 8.17 ppm to 8.21 ppm, or other signals, indicate that deuteration did not proceed in the synthesis scheme (a-1). Presumed to be hydrogen. 4-(3-bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 The deuteration rate was estimated by referring to the proton number of 4-(3-bromophenyl)dibenzothiophene, a non-deuterated product of . Figure 19(A) shows 4-(3-bromophenyl)dibenzothiophene 1 The H-NMR chart is shown in Figure 19(B) for 4-(3-bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 An enlarged view of δ=7.30 ppm to 8.30 ppm comparing (sample 1-1) and 4-(3-bromophenyl)dibenzothiophene (reference 1-1) is shown. For these reasons, 4-(3-bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 was estimated to be around 86%.

[0518] <Step 1-2; 2-[3-(dibenzo[b,d]thiophen-4-yl-1,2,3,6,7,8,9-d 7 ) phenyl-2,4,6-d 3 ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane> 4-(3-Bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 2.3 g (6.7 mmol) of , 1.9 g (7.4 mmol) of bis(pinacolate)diboron, 2.2 g (22 mmol) of potassium acetate, and 35 mL of N,N-dimethylformamide (DMF) were added, and the flask was stirred under reduced pressure. Degassed. After that, the inside of the flask was heated to 60°C under a nitrogen stream, and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (abbreviation: Pd(dppf) 2 Cl 2 CH 2 Cl 2 ) was added (0.32 g (0.39 mmol)), and the mixture was heated to 100° C. and stirred for 5 hours. After the reaction, extraction with toluene was performed, and the obtained organic layer was washed with saturated brine and dried over magnesium sulfate. This mixture was separated by gravity filtration, and the filtrate was concentrated to obtain a black oil. The resulting oil was purified by silica gel column chromatography (toluene:hexane=1:1 to toluene:hexane=1:0) to give the desired pale blue oil, 2-[3-(dibenzo[b, d]thiophen-4-yl-1,2,3,6,7,8,9-d 7 ) phenyl-2,4,6-d 3 1.7 g of ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was obtained in a yield of 65%. The synthesis scheme of step 1-2 is shown in formula (a-2) below.

[0519] [formation]

[0520] 2-[3-(dibenzo[b,d]thiophen-4-yl-1,2,3,6,7,8,9-d obtained in step 1-2 7 ) phenyl-2,4,6-d 3 ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane nuclear magnetic resonance spectroscopy ( 1 1 H-NMR) analysis results are shown below. again, 1 1 H-NMR charts are shown in FIGS. 20(A) and 20(B).

[0521] 1 H-NMR.δ(CDCl 3 ,300MHz): 1.37(s,12H),7.52-7.54(m,1H).

[0522] In FIG. 20(B), around δ=7.4 ppm to 7.5 ppm, around δ=8.1 ppm to 8.2 ppm, and other signals in the region enclosed by the dashed line in the figure are deuterium It is presumed that the peak is derived from the hydrogen remaining without conversion.

[0523] <Step 1-3; 4,8-bis[3-(dibenzothiophen-4-yl-1,2,3,6,7,8,9-d 7 ) phenyl-2,4,6-d 3 ]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm-d 20)> 2-[3-(dibenzo[b,d]thiophen-4-yl-1,2,3,6,7,8,9-d 7 ) phenyl-2,4,6-d 3 ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1.7 g (4.3 mmol), 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine 0.47 g (2.0 mmol) ), 2.5 g (12 mmol) of tripotassium phosphate, 0.89 g (12 mmol) of tert-butyl alcohol (abbreviation: tBuOH), and 30 mL of diethylene glycol dimethyl ether (abbreviation: diglyme) were added, and the inside of the flask was stirred under reduced pressure to degas. . After that, the inside of the flask was heated to 60 ° C. under a nitrogen stream, and palladium(II) acetate (abbreviation: Pd(OAc) 2 ) and 0.29 g (0.81 mmol) of di(1-adamantyl)-N-butylphosphine (abbreviation: cataCxiumA) were added, and the mixture was heated to 110° C. and stirred for 3.5 hours. Furthermore, the temperature was raised to 130° C. and the mixture was stirred for 4.5 hours. Furthermore, the temperature was raised to 150° C. and the mixture was stirred for 1.5 hours. After the reaction, water was added to the mixture, suction filtration was performed, and the filtrate was washed with water and ethanol. The filtered substance obtained was dissolved by heating with toluene, and filtered through a filtering agent laminated in the order of celite, alumina, and celite. After concentrating the filtrate, it was recrystallized with toluene to obtain 0.70 g of a white solid with a yield of 51%. 0.70 g of the resulting white solid was purified by sublimation by the train sublimation method. The conditions for sublimation purification were that the solid was heated at 355° C. while flowing argon gas at a pressure of 3.2 Pa and a flow rate of 7 mL / min. After purification by sublimation, 0.54 g of the target pale yellow solid was obtained with a recovery rate of 77%. The synthesis scheme of step 1-3 is shown in formula (a-3) below.

[0524] [formation]

[0525] In addition, nuclear magnetic resonance spectroscopy of the pale yellow solid obtained in the above step ( 1 1 H-NMR) analysis results are shown below. again, 1 The 1 H-NMR chart is shown in FIG. 21(A). Therefore, in Synthesis Example 1, 4,8mDBtP2Bfpm-d, which is one embodiment of the present invention represented by the above structural formula (100), 20 was obtained.

[0526] 1 H-NMR.δ(CDCl 3 ,500MHz): 7.67-7.68(m,1H),7.79-7.81(m,1H),7.83(d,J=8.59Hz,1H),8.07(dd,J1=8.59Hz,J2=1.72Hz,1H) ,8.63(sd,J=1.72Hz,1H),9.33(s,1H).

[0527] Further, in FIG. 21(B), minute signals can be confirmed around δ=7.45 ppm to 7.55 ppm and around 9.50 ppm, or others. It is presumed that this is hydrogen remaining without being deuterated in the synthesis scheme (a-1).

[0528] Figure 22(A) shows 4,8mDBtP2Bfpm-d 20 of 4,8mDBtP2Bfpm, the non-deuterated product of 1 1 H-NMR chart. In addition, FIG. 22(B) shows 4,8mDBtP2Bfpm-d at δ = 7.45ppm to 7.55ppm. 20 and 4,8mDBtP2Bfpm. A signal around 7.45 ppm to 7.55 ppm is a signal derived from the dibenzothiophene skeleton, and the deuteration rate is estimated to be about 88%. 4-(3-bromophenyl-2,4,6-d with a deuteration rate of about 86% 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 4,8mDBtP2Bfpm-d synthesized using 20 4-(3-bromophenyl-2,4,6-d 3 ) dibenzothiophene-1,2,3,6,7,8,9-d 7 The deuteration rate of the partial structure derived from 4,8mDBtP2Bfpm-d 20 was maintained after the synthesis of

[0529] <4,8mDBtP2Bfpm-d 20 Characteristics> followed by 4,8mDBtP2Bfpm-d 20 The ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum of a toluene solution of An ultraviolet-visible spectrophotometer (V-770DS, manufactured by JASCO Corporation) was used to measure the absorption spectrum, and the toluene solution was placed in a quartz cell and the measurement was performed at room temperature. For the measurement of the emission spectrum, a spectrofluorometer (FP-8600DS manufactured by JASCO Corporation) was used, the toluene solution was placed in a quartz cell, and the measurement was performed at room temperature. FIG. 23 shows the measurement results of the obtained absorption spectrum and emission spectrum. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity. Note that the absorption spectrum shown in FIG. 23 shows the result of subtracting the absorption spectrum measured by putting only toluene in the quartz cell from the absorption spectrum measured by putting the toluene solution in the quartz cell.

[0530] 4,8mDBtP2Bfpm-d as shown in Figure 23 20 In a toluene solution of , it has absorption peaks around 286 nm, 317 nm and 331 nm, and an emission peak was observed around 389 nm (excitation wavelength: 300 nm).

[0531] Then 4,8mDBtP2Bfpm-d 20 Absorption and emission spectra of solid thin films were measured. A solid thin film was formed on a quartz substrate by a vacuum deposition method. In addition, the absorption spectrum of the thin film is the absorbance (-log 10 Calculated from [%T / (100-%R)]). Note that %T represents transmittance and %R represents reflectance. An ultraviolet-visible spectrophotometer (Model U4100, manufactured by Hitachi High-Technologies Corporation) was used to measure the absorption spectrum. A fluorescence spectrophotometer (FP-8600DS manufactured by JASCO Corporation) was used to measure the emission spectrum. FIG. 24 shows the measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film. The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0532] From the result of Fig. 24, 4,8mDBtP2Bfpm-d 20 The solid thin film has absorption peaks near 287 nm, 325 nm and 338 nm, and an emission peak near 416 nm (excitation wavelength: 326 nm).

[0533] Also thin film 4,8mDBtP2Bfpm-d 20 was measured in the atmosphere with a photoelectron spectrometer (AC-3, manufactured by Riken Keiki Co., Ltd.). As a result of converting the obtained ionization potential value into a negative value, 4,8mDBtP2Bfpm-d 20 The HOMO level of was -6.25 eV. In addition, 4,8mDBtP2Bfpm-d obtained from the Tauc plot assuming direct transition from the absorption spectrum data of the thin film 20 The absorption edge of was 3.45 eV. Therefore, 4,8mDBtP2Bfpm-d 20 The solid-state optical energy gap of is estimated to be 3.45 eV. 20 could be estimated to be -2.80 eV. Thus, 4,8mDBtP2Bfpm-d 20 is found to have a wide energy gap of 3.45 eV in the solid state.

[0534] 4,8mDBtP2Bfpm-d 20 The glass transition temperature (Tg) of was measured. Tg was measured using a differential scanning calorimeter (DSC8500, manufactured by PerkinElmer Japan Co., Ltd.) with the powder placed on an aluminum cell. As a result, 4,8mDBtP2Bfpm-d 20 The Tg of was 136°C.

[0535] Also 4,8mDBtP2Bfpm-d 20 were measured by cyclic voltammetry (CV). For the measurement, an electrochemical analyzer (ALS model 600A manufactured by BAS Co., Ltd.) was used, and dehydrated N,N-dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%) was used as a solvent. 22705-6), and tetra-n-butylammonium perchlorate (n-Bu 4 NClO 4 ) (manufactured by Tokyo Kasei Co., Ltd., catalog number: T0836) was dissolved to a concentration of 100 mmol / L, and the measurement target was dissolved to a concentration of 2 mmol / L.

[0536] In addition, a platinum electrode (BAS Co., Ltd., PTE platinum electrode) was used as the working electrode, and a platinum electrode (BAS Co., Ltd., Pt counter electrode (5 cm)) was used as the auxiliary electrode. , Ag / Ag as a reference electrode + An electrode (RE7 non-aqueous solvent-based reference electrode manufactured by BAS Co., Ltd.) was used. The measurement was performed at room temperature (20° C. or higher and 25° C. or lower).

[0537] In addition, the scanning speed during CV measurement was standardized to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea is the intermediate potential between oxidation-reduction waves, and Ec is the intermediate potential between reduction-oxidation waves. Here, since it is known that the potential energy with respect to the vacuum level of the reference electrode used in this example is -4.94 [eV], the HOMO level [eV] = -4.94-Ea, the LUMO level [eV ]=-4.94-Ec, the HOMO and LUMO levels can be obtained, respectively.

[0538] In addition, the CV measurement was repeated 100 times, and the electrical stability of the compound was investigated by comparing the oxidation-reduction wave at the 100th cycle measurement with the oxidation-reduction wave at the 1st cycle.

[0539] 4,8mDBtP2Bfpm-d 20 The HOMO level was found to be around -6.2 eV from the measurement results of the oxidation potential Ea [V] of . On the other hand, the LUMO level was found to be -3.02 eV from the measurement results of the reduction potential Ec[V]. From this, 4,8mDBtP2Bfpm-d 20 was found to have low LUMO and HOMO levels. In addition, from the results of repeated measurements of oxidation-reduction waves, when comparing the waveforms after the 1st cycle and after 100 cycles, 89% of the peak intensity was maintained in the Ec measurement, so 4,8mDBtP2Bfpm-d 20 was confirmed to have very good resistance to reduction.

Example

[0540] ≪Synthesis Example 2≫ In this example, 4,8-bis[3-(dibenzothiophen-4-yl-1,2,3,6,7,8,9-d 7 )phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm-d 14 ) will be specifically described.

[0541] [formation]

[0542] <Step 2-1; 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d 7 Synthesis of> Deuterated toluene (abbreviation: toluene-d 8 ) and 16 g (46 mmol) of 4-(3-bromophenyl)dibenzothiophene were added and dissolved, and the inside of the flask was replaced with nitrogen. Molybdenum (V) pentachloride (abbreviation: MoCl 5 ) was added, and the mixture was refluxed at 100° C. for 6 hours under a nitrogen stream. After the reaction, 1.0 mol / L hydrochloric acid was added to this mixture, and the precipitated solid was removed by suction filtration. The filtrate was extracted with toluene, and the resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate to obtain a mixture. The mixture was separated by gravity filtration, and the filtrate was concentrated to give a brown oil. The resulting oil was purified by silica gel column chromatography (hexane) to give the desired 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d. 7 was obtained in 8.00 g with a yield of 50%. The synthesis scheme of step 2-1 is shown in formula (b-1) below.

[0543] [formation]

[0544] 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d obtained in step 2-1 above 7 nuclear magnetic resonance spectroscopy ( 1 1 H-NMR) analysis results are shown below. again, 1 1 H-NMR charts are shown in FIGS. 25(A) and 25(B).

[0545] 1 H-NMR.δ(CDCl 3 ,300MHz): 7.34-7.42(m,1H), 7.56-7.61(m,1H), 7.68-7.71(m,1H), 7.88-7.89(m,1H).

[0546] As can be seen from (a-1) shown in Example 1 and (b-1) in this example, by changing the heating time in step 2-1, light hydrogen to be replaced with deuterium is controlled. It is possible to For example, by heating at 100° C. for 6 hours, deuterium bonded to the dibenzothiophene skeleton undergoes a substitution reaction to deuterium. Further, when the heating is continued, the deuterium substitution of the phenyl group bonded to the dibenzothiophene skeleton also progresses.

[0547] In FIG. 25(B), the signals seen near δ = 7.81 ppm to 7.86 ppm and δ = 8.16 ppm to 8.21 ppm, or others, remained undeuterated in the synthesis scheme (b-1). Presumed to be hydrogen. 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d based on the peak at 7.34-7.42ppm(m,1H) which is not deuterated 7 The deuteration rate was estimated by referring to the proton number of 4-(3-bromophenyl)dibenzothiophene, a non-deuterated product of . Figure 26(A) shows 4-(3-bromophenyl)dibenzothiophene 1 The H-NMR chart of 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d is shown in Fig. 26(B). 7 An enlarged view of δ=7.30 ppm to 8.30 ppm comparing (sample2-1) and 4-(3-bromophenyl)dibenzothiophene (reference2-1) is shown. From these facts, 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d 7 was estimated to be about 78%.

[0548] <Step 2-2; 2-[3-(dibenzo[b,d]thiophen-4-yl-1,2,3,6,7,8,9-d 7 )Synthesis of phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane> 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d obtained in step 2-1 was added to a 200 mL three-necked flask. 7 8.0 g (23 mmol) of , 7.4 g (29 mmol) of bis(pinacolate)diboron, 8.9 g (90 mmol) of potassium acetate, and 116 mL of N,N-dimethylformamide (DMF) are added, and the flask is stirred under reduced pressure to degas. bottom. After that, the inside of the flask was heated to 60°C under a nitrogen stream, and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (abbreviation: Pd(dppf) 2 Cl 2 CH 2 Cl 2 ) was added, and the mixture was heated to 100°C and stirred for 5 hours. After the reaction, extraction with toluene was performed, and the resulting organic layer was washed with saturated saline and dried over magnesium sulfate to obtain a mixture. The mixture was separated by gravity filtration, and the filtrate was concentrated to obtain a black oil. The resulting oil was purified by silica gel column chromatography (toluene:hexane=1:1 to toluene:hexane=1:0) to give the desired yellow-green oil, 2-[3-(dibenzo[b, d]thiophen-4-yl-1,2,3,6,7,8,9-d 7 )Phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was obtained in an amount of 7.2 g with a yield of 79%. The synthesis scheme of step 2-2 is shown in formula (b-2) below.

[0549] [formation]

[0550] The 2-[3-(dibenzo[b,d]thiophen-4-yl-1,2,3,6,7,8,9-d obtained in this step 2-2 7 )Phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane nuclear magnetic resonance spectroscopy ( 1 1 H-NMR) analysis results are shown below. again, 1 1 H-NMR charts are shown in FIGS. 27(A) and 27(B).

[0551] 1 H-NMR.δ(CDCl 3 ,300MHz): 1.37(s,12H), 7.51-7.56(m,1H), 7.87-7.91(m,2H), 8.12(s,1H).

[0552] In FIG. 27(B), signals around δ=7.4 ppm to 7.5 ppm and other signals in the region enclosed by the dashed line in the figure are the remaining undeuterated hydrogen in the above formula (b-2). It is presumed to be the origin peak.

[0553] <Step 2-3; 4,8mDBtP2Bfpm-d 14 Synthesis of> 2-[3-(dibenzo[b,d]thiophen-4-yl-1,2,3,6,7,8,9-d 7)Phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 7.2 g (18 mmol), 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine 2.0 g (8.2 mmol), 11 g (50 mmol) of tripotassium phosphate, 3.9 g (53 mmol) of tert-butyl alcohol (abbreviation: tBuOH), and 85 mL of diethylene glycol dimethyl ether (abbreviation: diglyme) were added, and the inside of the flask was stirred under reduced pressure to degas. . After that, the inside of the flask was heated to 60 ° C. under a nitrogen stream, and palladium(II) acetate (abbreviation: Pd(OAc) 2 ) and 1.0 g (2.8 mmol) of di(1-adamantyl)-N-butylphosphine (abbreviation: cataCxiumA) were added, then the mixture was heated to 110° C. and stirred at the same temperature for 2 hours. Furthermore, the temperature was raised to 130° C., and the mixture was stirred at the same temperature for 4 hours. Furthermore, the temperature was raised to 155° C., and the mixture was stirred at the same temperature for 3.5 hours. After the reaction, water was added to the mixture in the flask, suction filtration was performed, and the filtrate was washed with water and ethanol. The filtered substance obtained was dissolved by heating with toluene, and filtered through a filtering agent laminated in the order of celite, alumina, and celite. After concentrating the filtrate, it was recrystallized with toluene to obtain 2.4 g of the target yellowish white solid at a yield of 41%. 2.4 g of the obtained yellowish white solid was purified by sublimation by the train sublimation method. The conditions for sublimation purification were that the solid was heated at 355° C. while flowing argon gas at a pressure of 2.9 Pa and a flow rate of 15 mL / min. After purification by sublimation, 1.4 g of the target pale yellow solid was obtained with a recovery rate of 58%. The synthesis scheme of step 2-3 is shown in formula (b-3) below.

[0554] [formation]

[0555] In addition, nuclear magnetic resonance spectroscopy of the pale yellow solid obtained in the above step ( 1 1 H-NMR) analysis results are shown below. again, 1 The 1 H-NMR chart is shown in FIG. 28(A). Therefore, in Synthesis Example 2, 4,8mDBtP2Bfpm-d, which is one embodiment of the present invention represented by the above structural formula (101), 14 was obtained.

[0556] 1 H-NMR.δ(CDCl 3 ,500MHz): 7.64-7.69(m,1H),7.79-7.84(m,4H),7.98(d,J=7.45Hz,1H),8.07(dd,J1=8.59Hz,J2=1.72Hz,1H) ,8.10(s,1H),8.63(sd,J=1.72Hz,1H),8.72(d,J=8.02Hz,1H),9.05(s,1H),9.33(s,1H).

[0557] Further, in FIG. 28(B), minute signals can be confirmed around δ=7.45 ppm to 7.55 ppm and 8.20 ppm to 8.25 ppm, or others. It is presumed that this is hydrogen remaining without being deuterated in the synthesis scheme (b-1).

[0558] Figure 29(A) shows 4,8mDBtP2Bfpm-d 14 of 4,8mDBtP2Bfpm, the non-deuterated product of 1 1 H-NMR chart. In addition, FIG. 29(B) shows 4,8mDBtP2Bfpm-d at δ = 7.45ppm to 7.55ppm. 14 and 4,8mDBtP2Bfpm. A signal around 7.45 ppm to 7.55 ppm is a signal derived from the dibenzothiophene skeleton, and the deuteration rate is estimated to be about 75%. 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d with 78% deuteration 7 4,8mDBtP2Bfpm-d synthesized using 14 is 4-(3-bromophenyl)dibenzothiophene-1,2,3,6,7,8,9-d 7 The deuteration rate of the partial structure derived from was able to be maintained until the synthesis of the final product.

[0559] <4,8mDBtP2Bfpm-d 14 Characteristics> followed by 4,8mDBtP2Bfpm-d 14 The ultraviolet-visible absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectru...

Claims

1. An organic compound represented by general formula (G1): 【Chemical 1】 (However, in the above general formula (G1), Q １ represents sulfur or oxygen, R １ ~R ５ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; A １ represents a substituted or unsubstituted aryl group having 6 to 100 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 100 carbon atoms; R １ ~R ５ , and A １ At least one of the hydrogen atoms is replaced with deuterium.

2. An organic compound represented by general formula (G1): 【Chemistry 2】 (However, in the above general formula (G1), Q １ represents sulfur or oxygen, R １ , R ２ , R ４ , and R ５ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; A １ represents a substituted or unsubstituted aryl group having 6 to 100 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 100 carbon atoms; R ３ represents an aryl group having 6 to 100 carbon atoms and including a substituted or unsubstituted substituent, or a heteroaryl group having 2 to 100 carbon atoms and including a substituted or unsubstituted substituent; A １ At least one of the hydrogen atoms of R １ ~R ５ At least one of the hydrogen atoms is replaced with deuterium.

3. An organic compound represented by general formula (G2): 【Chemistry 3】 (However, in the above general formula (G2), Q １ represents sulfur or oxygen, R １ , R ２ , R ４ , and R ５ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms; m represents an integer of 0 to 4; A ２ represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R ３ represents a substituted or unsubstituted aryl group having 6 to 100 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 100 carbon atoms; ２ , and R ３ At least one of the hydrogen atoms is deuterium.

4. An organic compound represented by general formula (G2): 【Chemistry 4】 (In the above general formula (G2), Q 1 represents sulfur or oxygen; R 1 , R 2 , R 4 , and R 5 each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; each α independently represents any one of formulas (α-1) to (α-20); m represents an integer of 0 to 4; A 2 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; R 3 represents an aryl group having 6 to 100 carbon atoms which has a substituted or unsubstituted substituent, or a heteroaryl group having 2 to 100 carbon atoms which has a substituted or unsubstituted substituent, and at least one of the hydrogen atoms contained in α, A 2 , and R 3 is deuterium. 【Chemistry 5】

5. An organic compound represented by general formula (G3): 【Chemistry 6】 (However, in the above general formula (G3), Q １ represents sulfur or oxygen, R １ , R ２ , and R ４ ~R １４ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; A ３ represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; m represents an integer of 0 to 4; A ３ and hydrogen atoms held by R １ , R ２ , and R ４ ~R １４ At least one of the atoms is deuterium.)

6. An organic compound represented by general formula (G4): 【Chemistry 7】 (However, in the above general formula (G4), Q １ and Q ２ each independently represents sulfur or oxygen, R １ , R ２ , and R ４ ~R ２１ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted polycyclic alkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; m represents an integer of 0 to 4; R １ , R ２ , and R ４ ~R ２１ At least one of the atoms is deuterium.)

7. In any one of claims 1 to 6, The organic compound, wherein the aryl group having 6 to 30 carbon atoms and the heteroaryl group having 2 to 30 carbon atoms are each independently represented by any one of formulas (Ar-1) to (Ar-80): 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】

8. In claim 1 or claim 2, The above A １ and R ３ are organic compounds with the same structure.

9. In any one of claims 1 to 6, An organic compound in which one or more hydrogen atoms other than the hydrogen atom directly bonded to the benzofuropyrimidine skeleton are deuterium atoms.

10. In any one of claims 1 to 6, An organic compound in which all hydrogen atoms in the molecular structure are deuterium atoms.

11. An organic compound represented by structural formula (100), (101), or (128). 【Chemistry 11】

12. A light-emitting device using the organic compound according to any one of claims 1 to 11.

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