KR20210018142A - Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting device - Google Patents

Abstract

The present invention relates to a benzofuro-pyridizine derivative, which is a novel organic compound represented by chemical formula G1. In chemical formula G1: Q represents oxygen or sulfur; A represents a group having a total carbon number of 12-100, and has at least one of a heteroaromatic ring, including a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring and a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure; and each of R^1 to R^5 independently represents H, a C1-C6 alkyl group, substituted or non-substituted C5-C7 monocyclic saturated hydrocarbon, substituted or non-substituted C7-C10 polycyclic saturated hydrocarbon, substituted or non-substituted C6-C13 aryl group, or a substituted or non-substituted C3-C12 heteroaryl group.

Description

Organic compounds, light-emitting devices, light-emitting devices, electronic devices, and lighting devices {ORGANIC COMPOUND, LIGHT-EMITTING DEVICE, LIGHT-EMITTING APPARATUS, ELECTRONIC DEVICE, AND LIGHTING DEVICE}

One embodiment of the present invention relates to an organic compound, a light emitting device, a light emitting device, an electronic device, and a lighting device. However, one embodiment of the present invention is not limited to the above technical field. That is, one aspect of the present invention relates to an object, a method, a manufacturing method, or a driving method. In addition, one aspect of the present invention relates to a process, a machine, a manufacture, and a composition of matter. Moreover, a semiconductor device, a display device, a liquid crystal display device, etc. are specifically mentioned as an example.

Light-emitting devices including an EL layer between a pair of electrodes (also referred to as organic EL elements) are thin and light, have fast response to input signals, and low power consumption. Displays, including, are receiving great attention, and the speed of technology development is also accelerating.

In the light-emitting device, by applying a voltage between a pair of electrodes, electrons and holes injected from each electrode recombine in the EL layer, and the light-emitting material (organic compound) contained in the EL layer becomes an excited state, and the excited state is It glows when it returns to the ground state. In addition, as the type of excited state, there are a singlet excited state (S ^* ) and a triplet excited state (T ^* ), light emission from a singlet excited state is called fluorescence, and light emission from a triplet excited state is called phosphorescence. Further, it is considered that their statistical production ratio in the light emitting device is S ^* :T ^* = 1:3. The luminescence spectrum obtained from the luminescent substance is peculiar to the luminescent substance, and by using different kinds of organic compounds as the luminescent substance, light-emitting devices of various luminescent colors can be obtained.

In order to improve the device characteristics of such a light-emitting device, improvement of the device structure and development of materials are being actively conducted (see, for example, Patent Document 1).

Japanese Unexamined Patent Application Publication No. 2010-182699

Therefore, in one aspect of the present invention, a novel organic compound is provided. In addition, one aspect of the present invention provides a novel organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton. In addition, one embodiment of the present invention provides a novel organic compound that can be used in a light emitting device. In addition, one embodiment of the present invention provides a novel organic compound that can be used in the EL layer of a light emitting device. In addition, a novel light emitting device with high reliability using a novel organic compound as an embodiment of the present invention is provided. It also provides a new light emitting device, a new electronic device, or a new lighting device. In addition, description of these problems does not interfere with the existence of other problems. In addition, in one embodiment of the present invention, it is not necessary to achieve all of the above problems. In addition, problems other than these will become apparent from the description of the specification, drawings, claims, and the like, and other problems can be extracted from the description of the specification, drawings, and claims.

One embodiment of the present invention is a benzofuropyridazine derivative, and is an organic compound represented by the following general formula (G1). Further, the organic compound represented by the following general formula (G1) has a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton.

[Formula 1]

In the general formula (G1), Q represents oxygen or sulfur. In addition, A is a group having a total carbon number of 12 to 100, and a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, and a heteroaromatic ring including a dibenzofuran ring. It has any one or more of a ring, a hetero-aromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. In addition, R ¹ to R ⁵ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted Or an unsubstituted C6-C13 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group.

In addition, another aspect of the present invention is a benzofuropyridazine derivative, and is an organic compound represented by the following general formula (G2). Further, as represented by the following general formula (G2), it has a hole-transporting skeleton at the 3 position of the benzofuro[3,2-c]pyridazine skeleton or the benzothieno[3,2-c]pyridazine skeleton.

[Formula 2]

In the general formula (G2), Q represents oxygen or sulfur. Further, α represents a substituted or unsubstituted phenylene group, and n represents an integer of 0 to 4. In addition, Ht _uni represents a skeleton having hole transport properties. In addition, R ¹ to R ⁵ are hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 13 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

In addition, another embodiment of the present invention is a benzofuropyridazine derivative, and is an organic compound represented by the following general formula (G3). Further, as represented by the following general formula (G3), it has a hole-transporting skeleton at the 3 position of the benzofuro[3,2-c]pyridazine skeleton or the benzothieno[3,2-c]pyridazine skeleton.

[Formula 3]

In the general formula (G3), Q represents oxygen or sulfur. In addition, Ht _uni represents a skeleton having hole transport properties. In addition, R ¹ to R ⁵ are hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 13 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

In addition, Ht _uni in the general formulas (G2) and (G3) in each of the above configurations each independently has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure.

In addition, Ht _uni in the general formulas (G2) and (G3) in each of the above configurations is independently represented by any one of the following general formulas (Ht-1) to (Ht-26).

[Formula 4]

[Formula 5]

In addition, in the general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. Further, R ² to R ⁷¹ each represent a substituent of 1 to 4, and independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. In addition, Ar ¹ represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

In addition, another aspect of the present invention is an organic compound represented by any one of structural formula (100) and structural formula (101).

[Formula 6]

In addition, another aspect of the present invention is a light emitting device using the organic compound which is one aspect of the present invention described above. Further, in the present invention, in addition to the organic compound, a light emitting device having a guest material is also included.

Another aspect of the present invention is a light emitting device using the organic compound as one aspect of the present invention described above. Also included in the present invention is an EL layer provided between a pair of electrodes or a light emitting device in which a light emitting layer included in the EL layer is formed using an organic compound which is one embodiment of the present invention. In addition to the above light emitting device, a case in which a layer containing an organic compound (for example, a cap layer) is provided in contact with an electrode is also included in the light emitting device and is also included in the present invention. In addition to the light emitting device, a light emitting device having a transistor, a substrate, or the like is also included in the scope of the invention. In addition to the above light emitting device, electronic devices or lighting devices having a microphone, a camera, a button for operation, an external connection, a housing, a cover, a support, or a speaker are also included in the scope of the invention.

In addition, one embodiment of the present invention includes a light-emitting device having a light-emitting device and a lighting device having a light-emitting device in its category. Therefore, in this specification, the light emitting device refers to an image display device or a light source (including a lighting device). In addition, a module to which a connector such as FPC (Flexible Printed Circuit) or TCP (Tape Carrier Package) is connected to the light emitting device, a module provided with a printed wiring board at the end of the TCP, or integrated into the light emitting device by the COG (Chip On Glass) method. It is assumed that all modules in which the circuit (IC) is directly mounted are also included in the light emitting device.

In one embodiment of the present invention, a novel organic compound can be provided. Further, in one embodiment of the present invention, a novel organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton can be provided. Further, in one embodiment of the present invention, a novel organic compound that can be used in a light emitting device can be provided. Further, in one embodiment of the present invention, a novel organic compound that can be used in the EL layer of a light emitting device can be provided. In addition, a novel light emitting device with high reliability can be provided by using a novel organic compound as an embodiment of the present invention. In addition, it is possible to provide a new light emitting device, a new electronic device, or a new lighting device.

1A to 1E are views for explaining the structure of a light emitting device.
2A to 2C are views for explaining a light emitting device.
3A is a top view illustrating a light emitting device, and FIG. 3B is a cross-sectional view illustrating the light emitting device.
4A is a diagram illustrating a mobile computer, FIG. 4B is a diagram illustrating a portable image reproducing apparatus, and FIG. 4C is a diagram illustrating a digital camera. FIG. 4D is a diagram for explaining a portable information terminal, FIG. 4E is a diagram for explaining a portable information terminal, and FIG. 4F is a diagram for explaining a television device, 4G is a diagram illustrating a portable information terminal.
5A to 5C are diagrams for describing an electronic device.
6A and 6B are views for explaining an automobile.
7A and 7B are views for explaining a lighting device.
8 is a ¹ H-NMR chart of an organic compound represented by Structural Formula (100).
9 is an ultraviolet/visible absorption spectrum and emission spectrum of an organic compound represented by Structural Formula (100).
10 is a phosphorescence spectrum of an organic compound represented by structural formula (100).
11 is a ¹ H-NMR chart of an organic compound represented by Structural Formula (101).
12 is an ultraviolet/visible absorption spectrum and emission spectrum of an organic compound represented by structural formula (101).

An embodiment of the present invention will be described in detail below with reference to the drawings. However, the present invention is not limited to the description below, and the form and details of the present invention can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not to be interpreted as being limited to the description of the following embodiments.

In addition, the location, size, range, etc. of each component shown in the drawings may not indicate the actual location, size, range, etc. for easy understanding. Accordingly, the disclosed invention is not necessarily limited to the position, size, and range disclosed in the drawings and the like.

In addition, in describing the configuration of the invention with reference to the drawings in the present specification and the like, reference numerals indicating the same are commonly used between different drawings.

(Embodiment 1)

In this embodiment, an organic compound which is one embodiment of the present invention will be described. In addition, the organic compound as an embodiment of the present invention is an organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton represented by the following general formula (G1). to be.

[Formula 7]

In addition, in the general formula (G1), Q represents oxygen or sulfur. In addition, A is a group having a total carbon number of 12 to 100, and a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, and a heteroaromatic ring including a dibenzofuran ring. It has one or more of a ring, a hetero-aromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. In addition, R ¹ to R ⁵ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted Or an unsubstituted C6-C13 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group.

In addition, another aspect of the present invention is an organic compound represented by the following general formula (G2). In addition, as represented by the following general formula (G2), the organic compound of one embodiment of the present invention is a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton. It has a hole-transporting skeleton at 3 position.

[Formula 8]

In the general formula (G2), Q represents oxygen or sulfur. Further, α represents a substituted or unsubstituted phenylene group, and n represents an integer of 0 to 4. In addition, Ht _uni represents a skeleton having hole transport properties. In addition, R ¹ to R ⁵ are hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 13 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

Further, another aspect of the present invention is an organic compound represented by the following general formula (G3). In addition, as represented by the following general formula (G3), the organic compound of one embodiment of the present invention is a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton. It has a hole-transporting skeleton at 3 position.

[Formula 9]

In the general formula (G3), Q represents oxygen or sulfur. In addition, Ht _uni represents a skeleton having hole transport properties. In addition, R ¹ to R ⁵ are hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 13 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

In addition, Ht _uni in the general formulas (G2) and (G3) each independently has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure.

In addition, Ht _uni in the general formulas (G2) and (G3) are each independently represented by any one of the following general formulas (Ht-1) to (Ht-26).

[Formula 10]

[Formula 11]

In addition, in the general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. Further, R ² to R ⁷¹ each represent a substituent of 1 to 4, and independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. In addition, Ar ¹ represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

In addition, in the general formula (G1), general formula (G2), and general formula (G3), a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms When a hydrocarbon, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms has a substituent, the substituent is a methyl group, ethyl group, propyl group, isopropyl group, butyl group , An alkyl group having 1 to 7 carbon atoms such as isobutyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group, or cyclopentyl group, cyclohexyl group, cycloheptyl group, 8, 9, 10-trinovo 6 to 13 carbon atoms such as a cycloalkyl group having 5 to 7 carbon atoms such as a Nanyl group, an aryl group having 6 to 12 carbon atoms such as a phenyl group, a naphthyl group, and a biphenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, and a carbazolyl group Heteroaryl group of, etc. are mentioned.

In addition, as a specific example of the case where R ¹ to R ⁵ in the general formulas (G1), (G2), and (G3) represent a monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a cyclopentyl group, a cyclohexyl group A practical group, a 1-methylcyclohexyl group, a cycloheptyl group, etc. are mentioned.

In addition, specific examples of the case where R ¹ to R ⁵ in the general formulas (G1), (G2), and (G3) represent a polycyclic saturated hydrocarbon having 7 to 10 carbon atoms include a norbornyl group, an adamantyl group. , Decalin group, tricyclodecyl group, and the like.

Further, specific examples of the case where R ¹ to R ⁵ in the general formulas (G1), (G2), and (G3) represent an aryl group having 6 to 13 carbon atoms include a phenyl group, an o-tolyl group, and m-tol A reyl group, p-tolyl group, mesityl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, fluorenyl group, and the like.

In addition, specific examples of the case where R ¹ to R ⁵ in the general formulas (G1), (G2), and (G3) represent an alkyl group having 1 to 6 carbon atoms include 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-methyl Pentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, etc. are mentioned.

In addition, specific examples of the case where R ¹ to R ⁵ in the general formula (G1), general formula (G2), and general formula (G3) represent a heteroaryl group having 3 to 12 carbon atoms include triazinyl group, pyrazinyl group, and pyrimidine Diary, pyridinyl group, quinolinyl group, isoquinolinyl group, benzothienyl group, benzofuranyl group, indolyl group, dibenzothienyl group, dibenzofuranyl group, or carbazolyl group.

In addition, since R ¹ to R ⁵ in the general formula (G1), general formula (G2), and general formula (G3) have a group represented by the above-described specific example, the organic compound as an aspect of the present invention has high thermal stability and It has physicochemical stability. In particular, when R ³ has a group represented by the above-described specific example, thermal stability is improved due to its structure, and since LUMO has high electron resistance due to stabilization, it is highly reliable by manufacturing a light emitting device using this material. A light emitting device can be obtained.

Next, the specific structural formula of the organic compound which is one embodiment of the present invention described above is shown below. However, the present invention is not limited to these.

[Formula 12]

[Formula 13]

[Formula 14]

In addition, the organic compound represented by the structural formulas (100) to (121) is an example of the organic compound represented by the general formula (G1), but the organic compound as an embodiment of the present invention is not limited thereto.

<< Synthesis method of organic compound represented by general formula (G1) >>

Next, it is one embodiment of the present invention, and an organic compound having a benzofuro[3,2-c]pyridazine skeleton or a benzothieno[3,2-c]pyridazine skeleton represented by the following general formula (G1) The synthesis method of is described.

[Formula 15]

In the general formula (G1), Q represents oxygen or sulfur. In addition, A is a group having a total carbon number of 12 to 100, and a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, and a heteroaromatic ring including a dibenzofuran ring. It has one or more of a ring, a hetero-aromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. In addition, R ¹ to R ⁵ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted Or an unsubstituted C6-C13 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group.

The synthesis scheme (A) of the organic compound represented by the general formula (G1) is shown below. The organic compound represented by the general formula (G1) is a halogen compound (A1) having a benzofuropyridazine skeleton or a benzothienopyridazine skeleton, as shown in the synthetic scheme (A) below, and a boronic acid compound ( It can be obtained by making A2) and a boronic acid compound (A3) react.

[Formula 16]

In the synthesis scheme (A), Q represents oxygen or sulfur. In addition, A is a group having a total carbon number of 12 to 100, and a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, and a heteroaromatic ring including a dibenzofuran ring. It has one or more of a ring, a hetero-aromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure. In addition, R ¹ to R ⁵ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted Or an unsubstituted C6-C13 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group. Further, X ¹ and X ² represent halogen, and it is particularly preferable that they are chlorine, bromine, or iodine. Y ¹ and Y ² represent boronic acid, boronic acid ester, or cyclic triol borate salt. Further, as the cyclic triol borate salt, potassium salt and sodium salt may be used in addition to lithium salt.

Further, the halogen compound (A1) used in the above synthesis scheme (A) can be synthesized as shown in the following synthesis scheme (B) when R ¹ of the halogen compound (A1) is hydrogen. That is, a halogenated benzofuran-3-one derivative or a benzothiophen-3-one derivative (B1) and a glyoxylic acid ester (B2) were reacted to obtain an intermediate (B3), and then reacted with hydrazine monohydrate. An intermediate (B4) can be obtained. By reacting this intermediate (B4) with a halogenating agent, a halogen compound (A1) having a benzofuropyridazine skeleton or a benzothienopyridazine skeleton can be synthesized.

[Formula 17]

In the above synthesis scheme (B), Q represents oxygen or sulfur. Further, X ¹ and X ² represent halogen, and it is particularly preferable that they are chlorine, bromine, or iodine. In the formula, R ⁶ represents an alkyl group and is preferably a methyl group or an ethyl group. In addition, the glyoxylic acid ester (B2) may be prepared by using a solution or a polymer type may be used.

Further, the halogen compound (A1) used in the synthesis scheme (A) can also be synthesized by the method shown in the following synthesis scheme (C). That is, it can also be obtained by cyclizing an intermediate (C3) obtained by reacting a dihalogen compound (C1) with a pyridazine compound (C2) substituted with a hydroxyl group or a sulfanyl group.

[Formula 18]

In the synthetic scheme (C), Q represents oxygen or sulfur. Further, X ¹ to X ⁴ represent halogen, X ¹ to X ³ is preferably chlorine, bromine, or iodine, and X ⁴ is preferably fluorine or chlorine.

In addition, compound (A1), compound (A2), compound (A3), compound (B1), compound (B2), compound (B3), compound (C1) used in the above synthetic schemes (A) to (C) , As the compound (C2) and the compound (C3), since various types of compounds are commercially available or can be synthesized, numerous types of compounds can be synthesized as organic compounds represented by the general formula (G1). Therefore, the organic compound of one embodiment of the present invention is rich in variations.

So far, an example of a method for synthesizing the organic compound of one embodiment of the present invention has been described, but the present invention is not limited thereto, and may be synthesized by other synthesis methods.

The configuration shown in this embodiment can be used in appropriate combination with the configuration shown in the other embodiments.

(Embodiment 2)

In this embodiment, a light emitting device using the organic compound shown in the first embodiment will be described with reference to FIG. 1.

<<Basic structure of light emitting device>>

First, the basic structure of the light emitting device will be described. Fig. 1A shows an example of 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.

In addition, in Fig. 1(B), a stack having a plurality of (two layers in Fig. 1B) EL layers 103a and 103b between a pair of electrodes, and a charge generation layer 104 between the EL layers An example of a light emitting device having a structure (tandem structure) has been shown. In addition, the stacked EL layers are not limited to two layers, and may be three or more.

When a voltage is applied to the first electrode 101 and the second electrode 102, the charge generation layer 104 injects electrons into one EL layer 103a or 103b, and the other EL layer 103b or It has a function of injecting holes into 103a). Therefore, when a voltage is applied to the first electrode 101 so that the potential is higher than that of the second electrode 102 in FIG. 1B, electrons are injected from the charge generation layer 104 to the EL layer 103a, Holes are injected into the EL layer 103b.

In addition, it is preferable that the charge generation layer 104 has light transmittance to visible light (specifically, the transmittance of visible light to the charge generation layer 104 is 40% or more) from the viewpoint of light extraction efficiency. In addition, the charge generation layer 104 functions even if the conductivity is lower than that of the first electrode 101 or the second electrode 102.

In Fig. 1(C), the EL layer 103 shown in Fig. 1(A) (the case where the EL layers 103a and 103b of Fig. 1(B) has a lamination structure is not the same) is a lamination structure. An example of the case of having However, in this case, it is assumed that the first electrode 101 functions as an anode. The EL layer 103 includes a hole (hole) injection layer 111, a hole (hole) transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron injection layer 115 on the first electrode 101. It has a sequentially stacked structure. Further, even in the case of having a plurality of EL layers as in the tandem structure shown in Fig. 1B, each EL layer has a structure in which the EL layers are sequentially stacked as shown in Fig. 1D from the anode side. In addition, each EL layer in FIG. 1D is a hole (hole) injection layer 111a, 111b, a hole (hole) transport layer 112a, 112b, light emitting layers 113a, 113b, electron transport layers 114a, 114b, It has electron injection layers 115a and 115b, respectively. Further, when the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order of the EL layers is reversed.

The light-emitting layer 113 included in the EL layers 103, 103a, and 103b can have a light-emitting substance or a plurality of substances, respectively, in an appropriate combination, and can be configured to obtain fluorescent or phosphorescent light having a desired color of light. Further, the light-emitting layer 113 may have a laminated structure having different light emission colors. Further, in this case, different materials may be used for the light-emitting materials or other materials used in each of the stacked light-emitting layers. Further, a configuration in which different light emission colors are obtained from the plurality of EL layers 103a and 103b shown in Fig. 1B may be employed. Also in this case, a different material may be used for the light-emitting material or other material used in each light-emitting layer. In addition, an organic compound, which is one embodiment of the present invention, may be used for the light emitting layer 113.

Further, in the light emitting device of one embodiment of the present invention, the light emission obtained by the EL layers 103, 103a, and 103b may be resonated between electrodes to enhance the light emission obtained. For example, in Fig. 1C, a micro-light resonator (microcavity) structure is formed by using the first electrode 101 as a reflective electrode and the second electrode 102 as a transflective/reflective electrode. Light emission obtained from the layer 103 can be enhanced.

In addition, when the first electrode 101 of the light emitting device is a reflective electrode made of a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. I can. Specifically, the distance between the electrodes of the first electrode 101 and the second electrode 102 with respect to the wavelength λ of the light obtained from the light emitting layer 113 is adjusted to be in the vicinity of mλ/2 (however, m is a natural number). desirable.

In addition, 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) where the desired light is obtained from the light emitting layer 113, and the second electrode ( It is preferable to adjust the optical distance from 102) to the region (light emitting region) where desired light is obtained from the light emitting layer 113 to be in the vicinity of (2m'+1)λ/4 (however, m'is a natural number). In addition, the light emitting region here means a recombination region of holes (holes) and electrons in the light emitting layer 113.

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.

However, in the above-described case, the optical distance between the first electrode 101 and the second electrode 102 is, strictly speaking, from the reflective area of the first electrode 101 to the reflective area of the second electrode 102 Is the total thickness of However, since it is difficult to precisely determine the reflective area of the first electrode 101 or the second electrode 102, arbitrary positions of the first electrode 101 and the second electrode 102 are designated as the reflective area. It is assumed that the above-described effects can be sufficiently obtained. In addition, the optical distance between the first electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, the optical distance between the reflective region of the first electrode 101 and the light-emitting region in the light-emitting layer from which the desired light is obtained. However, since it is difficult to precisely determine the reflective area in the first electrode 101 or the light-emitting area in the light emitting layer from which the desired light is obtained, an arbitrary position of the first electrode 101 is used as the reflective area. It is assumed that the above-described effects can be sufficiently obtained by assuming an arbitrary position of the obtained light-emitting layer as a light-emitting region.

When the light emitting device shown in Fig. 1C has a microcavity structure, light having a different wavelength (single color light) can be extracted even if the EL layer is common. Accordingly, formation of divisions (eg, RGB) for obtaining different luminous colors becomes unnecessary, and high definition can be achieved. It can also be combined with a colored layer (color filter). In addition, since the light emission intensity of a specific wavelength in the front direction can be increased, power consumption can be reduced.

The light-emitting device shown in Fig. 1E is an example of a light-emitting device of the laminated structure (tandem structure) shown in Fig. 1B, and as shown in the drawing, the three EL layers 103a, 103b, and 103c are It has a structure that is stacked with the charge generation layers 104a and 104b interposed therebetween. In addition, the three EL layers 103a, 103b, and 103c each have light-emitting layers 113a, 113b, and 113c, and the light emission colors of each light-emitting layer can be freely combined. For example, the emission layer 113a may be blue, the emission layer 113b may be red, green, and yellow, and the emission layer 113c may be blue, but the emission layer 113a may be red, and the emission layer 113b. ) May be blue, green, and yellow, and the light emitting layer 113c may be red.

Further, in the light emitting device according to one embodiment of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is an electrode having light-transmitting properties (transparent electrode, semi-transmissive/reflective electrode, etc.). When the light-transmitting electrode is a transparent electrode, the transmittance of visible light of the transparent electrode is 40% or more. Further, in the case of a transflective/reflective electrode, the reflectance of visible light of the transflective/reflective electrode is set to 20% or more and 80% or less, preferably 40% or more and 70% or less. In addition, it is preferable that these electrodes have a resistivity of 1×10 ⁻² Ωcm or less.

In addition, in the light emitting device of one embodiment of the present invention described above, when one of the first electrode 101 and the second electrode 102 is an electrode (reflective electrode) having reflectivity, the reflectivity of visible light of the reflective electrode is 40 % Or more and 100% or less, preferably 70% or more and 100% or less. In addition, it is preferable that this electrode has a resistivity of 1×10 ^-2 Ωcm or less.

<<Specific structure and manufacturing method of light emitting device>>

Next, a specific structure and manufacturing method of the light emitting device shown in Fig. 1, which is one embodiment of the present invention, will be described. In addition, as shown in Fig. 1(A) and Fig. 1(C), not only the light emitting device in which the EL layer 103 has a single-layer structure, but also Fig. 1(B), (D), and (E) The described tandem light-emitting device is also described. Further, when each light emitting device shown in Fig. 1 has a microcavity structure, for example, the first electrode 101 may be formed as a reflective electrode, and the second electrode 102 may be formed as a transflective/reflective electrode. In addition, one or more desired electrode materials may be used to form a single layer or laminated. Further, after forming the EL layers 103 and 103b, the second electrode 102 is formed by selecting a material similarly to the above. In addition, sputtering or vacuum evaporation can be used to prepare these electrodes.

<First electrode and second electrode>

As the material for forming the first electrode 101 and the second electrode 102, the following materials may be appropriately combined and used as long as the functions of the electrodes described above can be satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be suitably used. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, and In-W-Zn oxide are mentioned. In addition, aluminum (Al), 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) , Metals such as yttrium (Y) and neodymium (Nd), and alloys containing these in appropriate combinations may also be used. In addition, elements belonging to Group 1 or Group 2 of the periodic table of elements not illustrated above (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), and ether Rare-earth metals such as bium (Yb), alloys containing appropriate combinations thereof, graphene, and the like can be used.

In the light emitting device shown in Fig. 1, when the EL layer 103 has a laminated structure as shown in Fig. 1C and the first electrode 101 is an anode, the EL layer 103 is formed on the first electrode 101. ) Of the hole injection layer 111 and the hole transport layer 112 are sequentially stacked by a vacuum deposition method. In addition, as shown in FIG. 1D, when a plurality of EL layers 103a and 103b having a stacked structure are stacked by sandwiching the charge generation layer 104 and the first electrode 101 is an anode, the first electrode ( 101) After the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are sequentially stacked by the vacuum deposition method, the EL layer 103a and the charge generation layer 104 are sequentially stacked. Likewise, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are sequentially stacked on the charge generation layer 104.

<Hole injection layer and hole transport layer>

The hole injection layers 111, 111a, 111b are layers for injecting holes (holes) into the EL layers 103, 103a, 103b from the first electrode 101 or the charge generation layer 104, which is an anode, and has hole injection properties. This is a layer containing high material.

Examples of the material having high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide and manganese oxide. In addition, phthalocyanine-based compounds such as phthalocyanine (abbreviation: H ₂ Pc) or copper phthalocyanine (abbreviation: CuPc) can be used.

In addition, 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris(N-(3-methylphenyl), which are low molecular weight compounds) -N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4' -Bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (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), 3-[N-(1- Aromatic amine compounds, such as naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and the like can be used.

In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{), which are high molecular compounds (oligomers, dendrimers, polymers, etc.) 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. Or poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (abbreviation: PEDOT/PSS), polyaniline/poly(styrenesulfonic acid) (abbreviation: PAni/PSS) A system compound or the like can also be used.

Further, as a material having high hole injection properties, a composite material containing a hole transport material and an acceptor material (electron-accepting material) can also be used. In this case, electrons are extracted from the hole transport material by the acceptor material to generate holes in the hole injection layers 111, 111a, 111b, and the light emitting layers 113, 113a, and through the hole transport layers 112, 112a, 112b. Holes are injected into 113b). In addition, the hole injection layers 111, 111a, 111b may be formed of a single layer made of a composite material including a hole transport material and an acceptor material (electron-accepting material), but a layer including a hole transport material and an acceptor material ( An electron accepting material) may be laminated and formed.

The hole transport layers 112, 112a, and 112b are layers that transport holes injected from the first electrode 101 by the hole injection layers 111, 111a, and 111b to the emission layers 113, 113a, and 113b. Further, the hole transport layers 112, 112a, 112b are layers containing a hole transport material. As the hole transport material used for the hole transport layers 112, 112a, 112b, it is particularly preferable to use one having the same HOMO level as the hole injection layers 111, 111a, 111b, or close to the HOMO level.

As the acceptor material used for the hole injection layers 111, 111a, 111b, an oxide of a metal belonging to groups 4 to 8 of the periodic table of the elements can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide are mentioned. Among these, molybdenum oxide is particularly preferable because it is stable in the atmosphere and has low hygroscopicity and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranyl derivatives, and hexaazatriphenylene derivatives can be used. As one having an electron withdrawing group (halogen group or cyano group), 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ) , Chloranyl, 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), etc. are mentioned. In particular, a compound in which an electron withdrawing group is bonded to a condensed aromatic ring having a plurality of hetero atoms, such as HAT-CN, is preferable because it is thermally stable. [3] Radialene derivatives having an electron withdrawing group (especially halogen groups such as fluoro groups or cyano groups) are preferred because of their very high electron acceptability. Specifically, α,α',α"-1,2,3 -Cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetri Ylidentris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α',α''-1,2,3-cyclopro Paint lylidene tris [2,3,4,5,6-pentafluorobenzeneacetonitrile], and the like.

As a hole transport material used for the hole injection layers 111, 111a, 111b and the hole transport layers 112, 112a, 112b, when the square root of the electric field strength [V/cm] is 600, the hole mobility is 1 × 10 ^A material of ^-6 cm ² /Vs or more is preferred. Further, materials other than these can be used as long as it is a material having higher hole transport properties than electron transport properties.

As the hole-transporting material, a material having high hole-transporting properties such as a π electron-excessive heteroaromatic compound (for example, a carbazole derivative or a furan derivative) or an aromatic amine (a compound having an aromatic amine skeleton) is preferable.

Examples of the carbazole derivatives (compounds having a carbazole skeleton) include bicarbazole derivatives (for example, 3,3'-bicarbazole derivatives), aromatic amines having a carbazolyl group, and the like.

As the bicarbazole derivative (eg, 3,3'-bicarbazole derivative), specifically, 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9' -Bis(1,1'-biphenyl-4-yl)-3,3'-bi-9H-carbazole, 9,9'-bis(1,1'-biphenyl-3-yl)-3, 3'-bi-9H-carbazole, 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. have.

In addition, as an aromatic amine having a carbazolyl group, specifically, 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), 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)triphenyl Amine (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-phenylcarba Zol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3- Yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bi Fluoren-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-diphenyl) Aminophenyl)-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-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9- Dimethylfluorene-2,7-diamine (abbreviation: YGA2F), 4,4',4''-tris (carbazol-9-yl) triphenylamine (abbreviation: TCTA), and the like.

As carbazole derivatives, in addition to those described 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.

As the furan derivative (a compound having a furan skeleton), 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-) Compounds having a thiophene skeleton such as 9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 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) etc. are mentioned.

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-diphenylamino Phenyl)-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), 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), etc. are mentioned.

As a hole-transporting material, 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) can also be used.

However, the hole-transporting material is not limited to the above, and a combination of one or a plurality of known various materials is used as a hole-transporting material for the hole injection layers 111, 111a, 111b and the hole transport layers 112, 112a, 112b. I can. Further, the hole transport layers 112, 112a, 112b may be formed of a plurality of layers, respectively. That is, for example, the first hole transport layer and the second hole transport layer may be laminated.

In the light emitting device shown in Fig. 1, light emitting layers 113 and 113a are formed on the hole transport layers 112 and 112a of the EL layers 103 and 103a by a vacuum evaporation method. In the case of the light emitting device of the tandem structure shown in Fig. 1D, after the EL layer 103a and the charge generating layer 104 are formed, the light emitting layer 113b is also formed on the hole transport layer 112b of the EL layer 103b. It is formed by this vacuum evaporation method.

<Light-emitting layer>

The emission layers 113, 113a, 113b, and 113c are layers including a light emitting material. In addition, as the light-emitting material, a material exhibiting light-emitting colors such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red is appropriately used. In addition, by using different light-emitting materials for the plurality of light-emitting layers 113a, 113b, and 113c, a configuration that exhibits different light emission colors (for example, white light emission obtained by combining light emission colors having a complementary color relationship) can be obtained. Further, one light-emitting layer may have a stacked structure in which different light-emitting materials are formed.

Further, the light-emitting layers 113, 113a, 113b, and 113c may have one or more types of organic compounds (host materials, etc.) in addition to the light-emitting material (guest material). In addition, as one type or a plurality of types of organic compounds, one or both of the organic compound as an embodiment of the present invention and the hole-transport material and electron-transport material described in the present embodiment can be used.

The light-emitting material that can be used for the light-emitting layers 113, 113a, 113b, and 113c is not particularly limited, and a light-emitting material that converts singlet excitation energy into light emission in the visible region, or triplet excitation energy (ground state and triplet excitation A light-emitting material that converts the energy difference in the state) into light emission in the visible light region may be used.

Moreover, as another light emitting substance, the following are mentioned, for example.

As a light-emitting substance that converts singlet excitation energy into light emission, a substance that emits fluorescence (a fluorescent material) is exemplified, for example, a pyrene derivative, an anthracene derivative, a triphenylene derivative, a fluorene derivative, a carbazole derivative, and a dibenzo. Thiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, and the like. In particular, pyrene derivatives are preferred because of their high light emission quantum yield. As a specific example of the pyrene derivative, N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-dia Min (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(dibenzothiophen-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), etc. are mentioned.

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)triphenyl Amine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl) triphenylamine (abbreviation: 2YGAPPA), N,9-di Phenyl-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: 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-butyl) perylene (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-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10 -Diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) and the like can be used.

Further, as a light-emitting material that converts triplet excitation energy into light emission, for example, a material that emits phosphorescence (a phosphorescent material) or a material that emits thermally activated delayed fluorescence (TADF) may be mentioned.

Examples of the phosphorescent material include organic metal complexes, metal complexes (platinum complexes), and rare earth metal complexes. These materials exhibit different luminescence colors (luminescence peaks) for each substance, so they are appropriately selected and used as necessary.

Examples of the phosphorescent material exhibiting blue or green color and having a peak wavelength of 450 nm or more and 570 nm or less in the emission spectrum include the following materials.

For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-кN2]phenyl-кC}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 ]) organometallic complexes having a 4H-triazole skeleton, 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: [ Organometallic complexes having a 1H-triazole skeleton such as 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]phenanthridineto]iridium(III) (Abbreviation: [Ir(dmpimpt-Me) ₃ ]) Organometallic complexes having an imidazole skeleton, bis[2-(4',6'-difluorophenyl)pyridinato-N,C ^2' ]Iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C ^2' ]iridium(III ) Picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C ^2' }iridium(III)picolinate (abbreviation : [Ir(CF ₃ ppy) ₂ (pic)]), bis[2-(4',6'-difluorophenyl)pyridinato-N,C ^2' ]iridium(III)acetylacetonate ( Abbreviation: FIr(acac)) And organometallic complexes in which a phenylpyridine derivative having such an electron withdrawing group is used as a ligand.

Examples of the phosphorescent material exhibiting green or yellow color and having a peak wavelength of 495 nm or more and 590 nm or less in the emission spectrum include the following materials.

For example, tris (4-methyl-6-phenylpyrimidineto) 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)]), (acetylacetonone To)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-di Methyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-кN3]phenyl-кC}iridium(III) (abbreviation: [Ir(dmppm-dmp) ₂ (acac)]), ( Organometallic iridium complex having a pyrimidine skeleton such as acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm) ₂ (acac)]), (acetyl Acetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me) ₂ (acac)]), (acetylacetonato)bis(5 Organometallic iridium complex having a pyrazine skeleton such as -isopropyl-3-methyl-2-phenylpyrazinato)iridium (III) (abbreviation: [Ir(mppr-iPr) ₂ (acac)]), tris(2- Phenylpyridinato-N,C ^2' ) Iridium (III) (abbreviation: [Ir (ppy) ₃ ]), Bis (2-phenylpyridinato-N, C ^2' ) Iridium (III) acetylaceto Nate (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-phenylquinol) Linato-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-кN)phenyl-кC][2-(4-phenyl-2-pyridinyl-кN)phenyl-кC]iridium ( III) (abbreviation: [Ir(ppy) ₂ (4dppy)]), bis[2-(2-pyridinyl-кN)phenyl-кC][2-(4-methyl-5-phenyl-2-pyridinyl- Organometallic iridium complex having a pyridine skeleton such as кN)phenyl-кC], 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)) ]), as well as rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac) ₃ (Phen)]).

Examples of the phosphorescent material exhibiting yellow or red color and having a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum include the following substances.

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)]), (dipivaloyl meta Organometallic complexes having a pyrimidine skeleton such as naito)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-triphenyl Pyrazinato) (dipivaloylmethanato) iridium (III) (abbreviation: [Ir(tppr) ₂ (dpm)]), bis(4,6-dimethyl-2-[3-(3,5) -Dimethylphenyl)-5-phenyl-2-pyrazinyl-кN]phenyl-кC}(2,6-dimethyl-3,5-heptanedioneto-к 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-кN]phenyl-кC}(2,2,6,6-tetramethyl-3,5-heptanedioneto-к ² O,O') iridium (III) ( Abbreviation: [Ir(dmdppr-dmCP) 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)]), etc. Organometallic complexes having a pyrazine skeleton, tris(1-phenylisoquinolinato-N,C ^2' )iridium(III) (abbreviation: [Ir(piq) ₃ ]), bis(1-phenylisoquinoli) NATO-N,C ^2' ) Iridium (III) acetylacetone Acid (abbreviation: [Ir(piq) ₂ (acac)]), bis[4,6-dimethyl-2-(2-quinolinyl-кN)phenyl-кC](2,4-pentanedioneto- к ² O,O') Organometallic complex having a pyridine skeleton such as iridium (III), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum (II) ( Abbreviation: platinum complexes such as [PtOEP]), tris (1,3-diphenyl-1,3-propanedioneto) (monophenanthroline) europium (III) (abbreviation: [Eu(DBM) ₃ ( Phen)]), tris[1-(2-tenoyl)-3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: [Eu(TTA) ₃ (Phen )]) and other rare-earth metal complexes.

As the organic compound (host material, etc.) used in the light-emitting layers 113, 113a, 113b, and 113c, one or more materials having an energy gap larger than that of the light-emitting material (guest material) may be selected and used.

Therefore, when the light-emitting material used in the light-emitting layers 113, 113a, 113b, 113c is a fluorescent material, it is an organic compound (host material) used in combination with the light-emitting material, and has a large energy level in a singlet excited state, and triplet excitation It is preferable to use an organic compound having a small energy level in the state. In addition, as an organic compound (host material) used in combination with a light-emitting substance, the organic compound as an embodiment of the present invention shown in Embodiment 1, a hole transport material (described above) or an electron transport material (described later) shown in this embodiment In addition, a bipolar material or the like can be used. By using the organic compound as one embodiment of the present invention shown in Embodiment 1 for the light emitting layer (particularly by using it as a host material), it is possible to suppress initial deterioration of the light emitting device and improve reliability.

Although partially overlapping with the above-described specific example, a specific example of an organic compound preferably in combination with a light-emitting material (a fluorescent material, a phosphorescent material) is shown below.

When the light-emitting material is a fluorescent material, organic compounds (host materials) that can be used in combination with the light-emitting material include anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene. Condensed polycyclic aromatic compounds, such as a derivative, are mentioned. Moreover, it is preferable to use the organic compound which is one embodiment of this invention shown in Embodiment 1.

In addition, as a specific example of an organic compound (host material) used in combination with a fluorescent light emitting substance, 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 (abbreviation: DBC1), 9-[4 -(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: 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), 9,9'-Bianthryl (abbreviation: BANT), 9,9'-(Stilben-3,3'-diyl) diphenanthrene (abbreviation: DPNS), 9,9'- (Stilben-4,4'-diyl) diphenanthrene (abbreviation: DPNS2), 1,3,5-tri (1-pyrenyl) benzene (abbreviation: TPB3), 5,12-diphenyltetracene, 5,12-bee S(biphenyl-2-yl) tetracene, etc. are mentioned.

In addition, when the light-emitting material is a phosphorescent material, as the organic compound (host material) used in combination with the light-emitting material, an organic compound having a triplet excitation energy higher than the triplet excitation energy of the light-emitting material may be selected. Particularly, the organic compound which is one embodiment of the present invention shown in Embodiment 1 is suitable. In addition, when a plurality of organic compounds (for example, a first host material and a second host material (or assist material), etc.) are used in combination with a light emitting material to form an excited complex, the plurality of organic compounds are phosphorescent. It is preferable to use it in combination with the material.

By setting it as such a structure, light emission using ExTET (Exciplex-Triplet Energy Transfer), which is energy transfer from the excited composite to the light-emitting material, can be efficiently obtained. In addition, as a combination of a plurality of organic compounds, it is preferable that an excited complex is easily formed, and it is particularly preferable to combine a compound that is easy to receive holes (a hole transporting material) and a compound that is easily to receive electrons (an electron transporting material). In addition, the organic compound as an embodiment of the present invention described in Embodiment 1 is suitable as a host material in the case where the light emitting material is a phosphorescent material because the triplet excited state is stable. In the case of forming an excited composite as described above, it is suitable as an electron transport material. In addition, it is particularly suitable for use in combination with a phosphorescent material that emits green light because of its triplet excitation energy level.

In addition, when the light-emitting material is a phosphorescent material, organic compounds (host material, assist material) that can be used in combination with the light-emitting material include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, zinc or aluminum-based Metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, etc. I can.

In addition, as a specific example of the aromatic amine (a compound having an aromatic amine skeleton) which is an organic compound having high hole transport properties among the above, the same examples of the hole transport material described above can be mentioned.

Moreover, as a specific example of the carbazole derivative which is an organic compound with high hole-transport property, the same thing as the specific example of the above-mentioned hole-transport material can be mentioned.

Further, specific examples of dibenzothiophene derivatives and dibenzofuran derivatives, which are organic compounds with high hole transport properties, include 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzo Furan (abbreviation: mmDBFFLBi-II), 4,4',4''-(benzene-1,3,5-triyl) tri(dibenzofuran) (abbreviation: DBF3P-II), 1,3,5- Tri(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzo Thiophene (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.

Further, specific examples of zinc or aluminum-based metal complexes, which are organic compounds with high electron transport properties, are 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), such as a quinoline skeleton or a metal complex having a benzoquinoline skeleton. I can.

In addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ) Metal complexes having an oxazole-based or thiazole-based ligand such as such may be used.

In addition, specific examples of the oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, and phenanthroline derivatives, which are organic compounds with high electron transport properties, 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), vasophenanthroline (abbreviation: Bphen ), vasocuproin (abbreviation: BCP), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 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]quinox Saline (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), and the like.

Further, specific examples of the heterocyclic compound having a diazine skeleton, a heterocyclic compound having a triazine skeleton, and a heterocyclic compound having a pyridine skeleton, which are organic compounds having high electron transport properties, include 4,6-bis[3-(phenanthrene- 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-triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis[3-(9H-carbazole- 9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB), and the like. Moreover, the organic compound which is one embodiment of this invention especially shown in Embodiment 1 can also be used.

Moreover, as an organic compound with high electron transport property, poly(2,5-pyridindiyl) (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'-bipyridin-6,6 A high molecular compound such as'-diyl)] (abbreviation: PF-BPy) may also be used.

In addition, when a plurality of organic compounds are used in the light emitting layers 113, 113a, 113b, 113c, two kinds of compounds (first compound and second compound) forming an excited complex and an organic metal complex may be mixed and used. good. In this case, various organic compounds can be appropriately combined and used, but in order to efficiently form an excited complex, it is particularly desirable to combine a compound that is easy to receive holes (hole transport material) and a compound that is easy to receive electrons (electron transport material). desirable. Further, as the hole-transporting material and the electron-transporting material, the material specifically shown in the present embodiment can be used. With this configuration, high efficiency, low voltage, and long life can be simultaneously realized.

The TADF material refers to a material capable of up-converting (crossing between reverse terms) a triplet excited state to a singlet excited state by a trace amount of thermal energy and efficiently exhibiting light emission (fluorescence) from a singlet excited state. Further, 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, and preferably 0 eV or more and 0.1 eV or less. In addition, delayed fluorescence in the TADF material refers to light emission that has the same spectrum as that of ordinary fluorescence and has a remarkably long lifetime. Its lifetime is 10 ^-6 seconds or more, preferably 10 ^-3 seconds or more.

Examples of the TADF material include fullerene and its derivatives, acridine derivatives such as proflavin, and eosin. Further, a metal-containing porphyrin including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), and the like may be mentioned. Examples of the metal-containing porphyrin include protoporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Proto IX)), mesoporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Meso IX)), hematoporphyrin-fluoro. Tin rinide complex (abbreviation: SnF ₂ (Hemato IX)), coproporpyrintetramethylester-tin fluoride complex (abbreviation: SnF ₂ (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF ₂ (OEP)), an ethioporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Etio I)), an octaethyl porphyrin-platinum chloride complex (abbreviation: PtCl ₂ OEP), and the like.

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-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ- TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT ), 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthene-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'-anthracene]-10'-one ( Abbreviation: ACRSA) and other heterocyclic compounds having a π electron-excessive hetero-aromatic ring and a π electron-deficient hetero-aromatic ring can be used. In addition, the material in which the π electron-excessive hetero-aromatic ring and the π electron-deficient hetero-aromatic ring are directly bonded to each other strengthens both the donority of the π electron-excessive hetero-aromatic ring and the acceptor property of the π electron-deficient hetero-aromatic ring. It is particularly preferable because the energy difference between the state and the triplet excited state becomes small.

In addition, when a TADF material is used, it may be used in combination with other organic compounds. In particular, it is preferable to use the organic compound as a host material for the TADF material, which can be combined with the above-described host material, hole transport material, and electron transport material, and is one embodiment of the present invention shown in the first embodiment.

Further, the material can be used to form the light emitting layers 113, 113a, 113b by combining with a low molecular weight material or a polymer material. In addition, a known method (evaporation method, coating method, printing method, etc.) can be appropriately used for film formation.

In the light emitting device shown in Fig. 1, electron transport layers 114 and 114a are formed on the light emitting layers 113 and 113a of the EL layers 103 and 103a. In the case of the light emitting device of the tandem structure shown in Fig. 1D, after the EL layer 103a and the charge generating layer 104 are formed, the electron transport layer 114b is also formed on the light emitting layer 113b of the EL layer 103b. Is formed.

<Electron transport layer>

The electron transport layers 114, 114a, and 114b are layers that transport electrons injected from the second electrode 102 by the electron injection layers 115, 115a, and 115b to the emission layers 113, 113a, and 113b. Further, the electron transport layers 114, 114a, 114b are layers containing an electron transport material. As the electron transport material used for the electron transport layers 114, 114a, 114b, when the square root of the electric field strength [V/cm] is 600, a material having an electron mobility of 1×10 ^-6 cm ² /Vs or more is preferable. . Further, materials other than these can be used as long as it is a material having higher electron transport properties than hole transport properties. Moreover, since the organic compound which is one embodiment of this invention shown in Embodiment 1 is excellent in electron transport property, it can be used also as an electron transport layer.

As the electron transporting material, in addition to a metal complex having a quinoline skeleton, a metal complex having a benzoquinoline skeleton, a metal complex having an oxazole skeleton, a metal complex having a thiazole skeleton, etc., oxadiazole derivatives, triazole derivatives, imidazole derivatives , Oxazole derivatives, thiazole derivatives, phenanthroline derivatives, quinoline derivatives having a quinoline ligand, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing Materials having high electron transport properties, such as a π electron deficient heteroaromatic compound including a heteroaromatic compound, can be used.

Specific examples of the electron transporting material include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq ₃ ), tris(4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis( 10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq) , A metal complex having a quinoline skeleton or a benzoquinoline skeleton such as bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (Abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), and the like, and other metal complexes having an oxazole skeleton or a thiazole skeleton.

In addition to the metal complex, 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-oxadiazole- 2-yl)phenyl]-9H-carbazole (abbreviation: CO11) and other oxadiazole derivatives, 3-(4'-tert-butylphenyl)-4-phenyl-5-(4''-biphenyl)- 1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4- Triazole derivatives such as 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: mDBTBIm-II) and other imidazole derivatives (benzimidazole derivatives) ) B, oxazole derivatives such as 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), vasophenanthroline (abbreviation: Bphen), vasocuproin (abbreviation : BCP), phenanthroline derivatives such as 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), 2-[3-(di Benzothiophen-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 Quinoxaline derivatives such as [f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), or dibenzoquinoxaline derivatives, 3,5-bis[3-(9H-carbazole-9) -Yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB) and other pyridine derivatives, 4,6-bis[3-( Phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), Pyrimidine derivatives such as 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{4-[3-(N-phenyl-9H-) Triazine derivatives such as carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) can be used. Moreover, the organic compound which is one embodiment of this invention shown in Embodiment 1 can also be used.

Also poly(2,5-pyridindiyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridin-3,5-diyl)] (Abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridin-6,6'-diyl)] (abbreviation : Polymer compounds such as PF-BPy) can also be used.

In addition, the electron transport layers 114, 114a, and 114b may have a structure in which two or more layers of the material are stacked, as well as a single layer.

Next, in the light emitting device shown in Fig. 1D, an electron injection layer 115a is formed on the electron transport layer 114a of the EL layer 103a by a vacuum evaporation method. Thereafter, the EL layer 103a and the charge generation layer 104 are formed, and after the electron transport layer 114b of the EL layer 103b is formed, an electron injection layer 115b is formed thereon by a vacuum evaporation method.

<Electron injection layer>

The electron injection layers 115, 115a, 115b are layers containing a material having high electron injection properties. The electron injection layers 115, 115a, 115b include alkali metals such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), and lithium oxide (LiO _x ), alkaline earth metals, or Compounds can be used. In addition, rare earth metal compounds such as erbium fluoride (ErF ₃ ) can be used. Further, an electron may be used for the electron injection layers 115, 115a, 115b. Examples of the electronic product include substances in which electrons are added at a high concentration to a mixed oxide of calcium and aluminum. In addition, a material constituting the electron transport layers 114, 114a, and 114b described above may be used.

Further, for the electron injection layers 115, 115a, 115b, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used. Such a composite material is excellent in 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 having excellent transport of generated electrons. Specifically, for example, an electron transporting material (metal complex or heteroaromatic compound) used for the above-described electron transport layers 114, 114a, 114b You can use The electron donor may be a substance that exhibits electron donation to an organic compound. Specifically, an alkali metal, alkaline earth metal, or rare earth metal is preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like are exemplified. Further, an alkali metal oxide or an alkaline earth metal oxide is preferable, and lithium oxide, calcium oxide, barium oxide, and the like are exemplified. Further, Lewis bases such as magnesium oxide can also be used. Further, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

Further, in the light emitting device shown in Fig. 1D, when amplifying light obtained from the light emitting layer 113b, the optical distance between the second electrode 102 and the light emitting layer 113b is the wavelength of light indicated by the light emitting layer 113b It is preferably formed to be less than 1/4 of λ. In this case, it can be adjusted by changing the film thickness of the electron transport layer 114b or the electron injection layer 115b.

<Charge generation layer>

In the light emitting device shown in Fig. 1D, when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102, the charge generation layer 104 is the EL layer ( It has a function of injecting electrons into 103a) and injecting holes into the EL layer 103b. In addition, the charge generation layer 104 may have a configuration in which an electron acceptor (acceptor) is added to a hole transport material, or may be a configuration in which an electron donor (donor) is added to the electron transport material. Further, both of these configurations may be laminated. Further, by forming the charge generation layer 104 using the above-described material, it is possible to suppress an increase in the driving voltage when the EL layer is laminated.

In the case where the electron acceptor is added to the hole transport material in the charge generation layer 104, the material shown in the present embodiment can be used as the hole transport material. Moreover, as an electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ), chloranyl, etc. are mentioned. Further, oxides of metals belonging to groups 4 to 8 of the periodic table of the elements may be mentioned. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, and the like may be mentioned.

In the case where the charge generating layer 104 has an electron donor added to the electron transport material, the material shown in the present embodiment can be used as the electron transport material. Further, as the electron donor, an alkali metal or alkaline earth metal or rare earth metal, or a metal belonging to groups 2 and 13 of the periodic table of the elements, and oxides and carbonates thereof can be used. Specifically, it is preferable to use lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, and the like. Further, an organic compound such as tetrathianapthacene may be used as the electron donor.

Further, the EL layer 103c of Fig. 1E may have the same configuration as the above-described EL layers 103, 103a, and 103b. Further, the charge generation layers 104a and 104b may also have the same configuration as the charge generation layer 104 described above.

<Substrate>

The light emitting device shown in this embodiment can be formed on various substrates. In addition, the type of the substrate is not limited to a specific one. Examples of the substrate include a semiconductor substrate (e.g., a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having a stainless steel foil, a tungsten substrate, and a tungsten foil. The eggplant may be a substrate, a flexible substrate, a bonding film, a paper containing a fibrous material, or a base film.

Further, examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, or soda-lime glass. In addition, examples of flexible substrates, bonding films, and base films include plastics typified by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), synthetic resins such as acrylic resins, and polypropylene. , Polyester, polyvinyl fluoride, or polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor deposition film, or paper.

In addition, a vacuum process such as a vapor deposition method or a solution process such as a spin coating method or an inkjet method can be used to manufacture the light emitting device shown in this embodiment. In the case of using the vapor deposition method, a physical vapor deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam vapor deposition method, a molecular beam vapor deposition method, and a vacuum vapor deposition method, or a chemical vapor deposition method (CVD method) can be used. In particular, functional layers (hole injection layers 111, 111a, 111b), hole transport layers 112, 112a, 112b, light emitting layers 113, 113a, 113b, 113c, and electron transport layers 114 included in the EL layer of the light emitting device 114a, 114b), electron injection layers 115, 115a, 115b, and charge generation layers 104, 104a, 104b), evaporation (vacuum evaporation, etc.), coating (dip coating, die coating, bar coating) Method, spin coating method, spray coating method, etc.), printing method (ink jet method, screen (stencil printing) method, offset (flat plate printing) method, flexo (steel plate printing) method, gravure method, micro contact method, nanoimprint method And the like).

In addition, each functional layer (hole injection layers 111, 111a, 111b) constituting the EL layers 103, 103a, 103b of the light emitting device shown in this embodiment, hole transport layers 112, 112a, 112b, light emitting layer 113, 113a, 113b, 113c), electron transport layers 114, 114a, 114b, electron injection layers 115, 115a, 115b, and charge generation layers 104, 104a, 104b) are not limited to the above-described materials, and Other materials can be used in combination as long as they can satisfy the function of each layer. As an example, a high molecular compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (a compound in the intermediate region between a low molecule and a polymer: molecular weight 400 to 4000), an inorganic compound (a quantum dot material, etc.) can be used. . In addition, 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, and the like can be used.

It is assumed that the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in the other embodiments.

(Embodiment 3)

In this embodiment, a light emitting device according to an embodiment of the present invention will be described. In addition, the light emitting device shown in Fig. 2A is an active matrix type light emitting device in which a transistor (FET) 202 on the first substrate 201 and the light emitting devices 203R, 203G, 203B, and 203W are electrically connected. , The plurality of light emitting devices 203R, 203G, 203B, and 203W have a common EL layer 204, and have a microcavity structure in which the optical distance between electrodes of each light emitting device is adjusted according to the light emission color of each light emitting device. Further, it is a top emission type light emitting device in which light emission obtained from the EL layer 204 is emitted through the color filters 206R, 206G, and 206B formed on the second substrate 205.

The light emitting device shown in Fig. 2A is formed so that the first electrode 207 functions as a reflective electrode. Further, the second electrode 208 is formed to function as a transflective/reflective electrode. In addition, as an electrode material for forming the first electrode 207 and the second electrode 208, it may be appropriately used with reference to the description of other embodiments.

In Fig. 2A, for example, the light-emitting device 203R is a red light-emitting device, the light-emitting device 203G is a green light-emitting device, the light-emitting device 203B is a blue light-emitting device, and the light-emitting device 203W. In the case of a white light emitting device, as shown in Fig. 2B, the light emitting device 203R is adjusted so that the distance between the first electrode 207 and the second electrode 208 becomes the optical distance 200R, The light emitting device 203G is adjusted so that the distance between the first electrode 207 and the second electrode 208 becomes an optical distance 200G, and the light emitting device 203B includes the first electrode 207 and the second electrode 208 It is adjusted so that the distance becomes the optical distance 200B. In addition, as shown in Fig. 2B, in the light emitting device 203R, a conductive layer 210R is stacked on the first electrode 207, and in the light emitting device 203G, a conductive layer 210G is deposited on the first electrode ( 207), optical adjustment can be performed.

Color filters 206R, 206G, and 206B are formed on the second substrate 205. In addition, the color filter is a filter that transmits light in a specific wavelength range in visible light and blocks light in a specific wavelength range. Accordingly, as shown in Fig. 2A, by providing a color filter 206R that transmits only light in a red wavelength region at a position overlapping with the light emitting device 203R, red light emission from the light emitting device 203R is provided. Can be obtained. Further, by providing a color filter 206G that transmits only light in a green wavelength region at a position overlapping with the light emitting device 203G, green light emission can be obtained from the light emitting device 203G. Further, by providing a color filter 206B that transmits only light in a blue wavelength region at a position overlapping with the light emitting device 203B, blue light emission can be obtained from the light emitting device 203B. However, the light emitting device 203W can obtain white light emission even without providing a color filter. Further, a black layer (black matrix) 209 may be provided at the end of one type of color filter. Further, the color filters 206R, 206G, 206B and the black layer 209 may be covered with an overcoat layer made of a transparent material.

2A shows a light emitting device having a structure (top emission type) that extracts light emission toward the second substrate 205, but the FET 202 is formed as shown in FIG. 2C. 1 A light emitting device having a structure (bottom emission type) that extracts light toward the substrate 201 may be used. Further, in the case of the bottom emission type light emitting device, the first electrode 207 is formed to function as a transflective/reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. In addition, at least a light-transmitting substrate is used for the first substrate 201. Further, the color filters 206R', 206G', and 206B' may be provided on the side of the first substrate 201 rather than the light emitting devices 203R, 203G, and 203B, as shown in Fig. 2C.

Further, in Fig. 2A, the case where the light emitting device is a red light emitting device, a green light emitting device, a blue light emitting device, and a white light emitting device is shown, but the light emitting device of one embodiment of the present invention is not limited to its configuration, A configuration including a light emitting device or an orange light emitting device may be used. In addition, as a material used for the EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer, etc.) in order to manufacture these light-emitting devices, referring to the description of other embodiments, it may be appropriately used. . Further, in that case, it is necessary to appropriately select a color filter according to the light emission color of the light emitting device.

By setting it as the above-described configuration, it is possible to obtain a light-emitting device having a light-emitting device displaying a plurality of luminous colors.

In addition, the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in the other embodiments.

(Embodiment 4)

In this embodiment, a light emitting device according to an embodiment of the present invention will be described.

By applying the element configuration of a light emitting device according to one embodiment of the present invention, an active matrix light emitting device or a passive matrix light emitting device can be manufactured. Further, the active matrix type light emitting device has a configuration in which a light emitting device and a transistor (FET) are combined. Therefore, both the passive matrix type light emitting device and the active matrix type light emitting device are included in one embodiment of the present invention. Further, the light emitting device shown in the other embodiments can be applied to the light emitting device according to the present embodiment.

In this embodiment, an active matrix light emitting device will be described with reference to FIG. 3.

In addition, (A) of FIG. 3 is a top view showing a light emitting device, and (B) of FIG. 3 is a cross-sectional view of (A) of FIG. 3 taken along a chain line A-A'. The active matrix type light emitting device has a pixel portion 302 provided on a first substrate 301, a driving circuit portion (source line driving circuit) 303, and driving circuit portions (gate line driving circuits) 304a and 304b. The pixel portion 302 and the driving circuit portions 303, 304a, 304b are sealed between the first substrate 301 and the second substrate 306 by the seal material 305.

Further, a lead wiring 307 is provided on the first substrate 301. The lead wiring 307 is electrically connected to the FPC 308 which is an external input terminal. In addition, the FPC 308 transfers external signals (eg, video signals, clock signals, start signals, reset signals, etc.) or potentials to the driving circuit units 303, 304a, 304b. Further, the FPC 308 may be provided with a printed wiring board (PWB). In addition, the state provided with these FPCs or PWBs is included in the category of light emitting devices.

Next, a cross-sectional structure is shown in Fig. 3B.

The pixel portion 302 includes a plurality of pixels having an FET (switching FET) 311, an FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312. . Further, the number of FETs each pixel has is not particularly limited, and can be appropriately provided as needed.

The FETs 309, 310, 311, and 312 are not particularly limited, and transistors such as a staggered type or an inverted staggered type can be applied. Further, a transistor structure such as a top gate type or a bottom gate type may be used.

In addition, the crystallinity of the semiconductors that can be used in these FETs 309, 310, 311, 312 is not particularly limited, and an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a part of a crystal region) Eggplant semiconductor) may be used. Further, by using a semiconductor having crystallinity, deterioration of transistor characteristics can be suppressed, which is preferable.

Further, as these semiconductors, for example, group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, and the like can be used. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, and the like can be applied.

The driving circuit part 303 has an FET 309 and an FET 310. Further, the driving circuit portion 303 may be formed of a circuit including a unipolar (only one of the N-type and P-type) transistors, or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. Further, it may be configured to have a drive circuit externally.

The end of the first electrode 313 is covered with an insulating material 314. In addition, organic compounds such as negative photosensitive resin and positive photosensitive resin (acrylic resin), and inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride may be used for the insulating material 314. It is preferable to have a surface having a curvature at the upper end or the lower end of the insulating material 314. Thereby, the coating property of the film formed on the insulating material 314 can be made favorable.

An EL layer 315 and a second electrode 316 are stacked on the first electrode 313 and formed. The EL layer 315 has a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like.

Further, to the configuration of the light emitting device 317 shown in the present embodiment, the configurations and materials shown in the other embodiments can be applied. Further, although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.

In the cross-sectional view of Fig. 3B, only one light-emitting device 317 is shown, but in the pixel portion 302, it is assumed that a plurality of light-emitting devices are arranged in a matrix. A light-emitting device capable of full-color display can be formed by selectively forming light-emitting devices in which three types of light emission (R, G, B) are obtained in the pixel portion 302, respectively. In addition, it is not limited to a light-emitting device that emits light of three types (R, G, B), for example, a light-emitting device that emits light such as white (W), yellow (Y), magenta (M), and cyan (C). May be formed. For example, by adding the above-described light emitting device from which various kinds of light emission are obtained to the light emitting device from which light emission of three types (R, G, B) is obtained, effects such as improvement of color purity and reduction of power consumption can be obtained. Further, by combining with a color filter, a light emitting device capable of full color display may be obtained. In addition, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), and the like can be used as the type of color filter.

By bonding the second substrate 306 and the first substrate 301 by the actual material 305, the FETs 309, 310, 311, 312 on the first substrate 301 and the light emitting device 317 are The substrate 301, the second substrate 306, and the region 318 surrounded by the actual material 305 are provided. Further, the region 318 may be filled with an inert gas (such as nitrogen or argon) or an organic material (including the actual material 305).

Epoxy resin or glass frit can be used for the seal material 305. In addition, it is preferable to use a material that does not allow moisture or oxygen to permeate as much as possible for the actual material 305. In addition, for the second substrate 306, what can be used for the first substrate 301 can be used similarly. Therefore, it is assumed that the various substrates described in the other embodiments can be appropriately used. As the substrate, in addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, or acrylic resin can be used. When a glass frit is used as an actual material, it is preferable that the first substrate 301 and the second substrate 306 are glass substrates from the viewpoint of adhesiveness.

Thereby, an active matrix type light emitting device can be obtained.

In addition, when the active matrix type light emitting device is formed on a flexible substrate, the FET and the light emitting device may be directly formed on the flexible substrate, but after forming the FET and the light emitting device on another substrate having a peeling layer, heat and power are applied. The FET and the light emitting device may be peeled off from the peeling layer by applying or performing laser irradiation or the like, and transferred to a flexible substrate. Further, as the release layer, for example, an inorganic film lamination of a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. In addition, as a flexible substrate, in addition to a substrate on which a transistor can be formed, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a textile substrate (natural fiber (silk), cotton, hemp) ), synthetic fibers (nylon, polyurethane, polyester), or recycled fibers (including acetate, cupra, rayon, recycled polyester, etc.), leather substrates, or rubber substrates. By using these substrates, durability and heat resistance become excellent, and weight reduction and thickness reduction can be achieved.

In addition, the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in the other embodiments.

(Embodiment 5)

In this embodiment, examples of various electronic devices and automobiles completed by applying the light emitting device of one embodiment of the present invention and the light emitting device having the light emitting device of one embodiment of the present invention will be described. Further, the light-emitting device can be mainly applied to a display unit in the electronic device according to the present embodiment.

The electronic devices shown in FIGS. 4A to 4E include a housing 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, an operation key 7005 (a power switch or an operation switch). ), connection terminal 7006, sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical, sound, time, hardness, Including a function of measuring electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell, or infrared light), a microphone 7008, and the like.

4A illustrates a mobile computer, and may have a switch 7009 and an infrared port 7010 in addition to the above.

4B shows a portable image reproducing apparatus (for example, a DVD reproducing apparatus) having a recording medium, and may have a second display unit 7002, a recording medium reading unit 7011, etc. in addition to the above. .

4C shows a digital camera having a television receiving function, and may have an antenna 7014, a shutter button 7015, a receiving unit 7016, and the like in addition to the above.

4D shows a portable information terminal. The portable information terminal has a function of displaying information on three or more surfaces of the display unit 7001. Here, an example in which information 7052, information 7053, and information 7054 are displayed on different sides has been shown. For example, the user may check the information 7053 displayed at a position that can be observed from above the portable information terminal while putting the portable information terminal in the breast pocket of the clothes. The user can check the display without taking the portable information terminal out of the pocket and, for example, determine whether to answer a phone call.

4E is a portable information terminal (including a smartphone), and may have a display portion 7001, an operation key 7005, and the like in the housing 7000. Further, a speaker 9003, a connection terminal 7006, a sensor 9007, and the like may be provided to the portable information terminal. In addition, the portable information terminal can display text or image information on a plurality of surfaces. Here, an example in which three icons 7050 are displayed is shown. In addition, information 7051 indicated by a broken line rectangle may be displayed on the other side of the display portion 7001. Examples of the information 7051 include incoming notifications such as e-mail, SNS, telephone, etc., title and sender name, date and time, time, remaining battery capacity, antenna reception strength, and the like of e-mail or SNS. Alternatively, an icon 7050 or the like may be displayed at a position where the information 7051 is displayed.

4F shows a large-sized television device (also referred to as a television or television receiver), and may have a housing 7000, a display portion 7001, and the like. In addition, a configuration in which the housing 7000 is supported by a stand 7018 is shown here. Further, the television device can be operated by a separate remote controller 7111 or the like. Further, a touch sensor may be provided on the display portion 7001, or operation may be performed by touching the display portion 7001 with a finger or the like. The remote controller 7111 may have a display section that displays information output from the remote controller 7111. Channels can be manipulated, volume can be adjusted, and images displayed on the display unit 7001 can be manipulated by operation keys or touch panels of the remote controller 7111.

The electronic devices shown in FIGS. 4A to 4F may have various functions. For example, a function to display various information (still images, moving pictures, text images, etc.) on the display unit, a touch panel function, a function to display a calendar, date or time, etc., a function to control processing by various software (programs), The wireless communication function, the function of connecting to various computer networks using the wireless communication function, the function of transmitting and receiving various data using the wireless communication function, the function of reading programs or data recorded in the recording medium and displaying them on the display unit, etc. Can have. In addition, in an electronic device having a plurality of display units, a three-dimensional image is displayed by displaying image information mainly on one display unit and mainly character information on another display unit, or by displaying an image in consideration of parallax on a plurality of display units. It may have a function of displaying. In addition, in an electronic device having a receiving unit, a function to shoot a still image, a function to shoot a video, a function to automatically or manually correct the captured image, a function to store the captured image in a recording medium (external or built-in camera), It may have a function of displaying a captured image on the display unit. In addition, the functions that the electronic devices shown in FIGS. 4A to 4F may have are not limited to these, and may have various functions.

4G is a wristwatch type portable information terminal, which can be used as a smart watch, for example. This wristwatch type portable information terminal includes a housing 7000, a display portion 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a microphone 7026, a sensor 7029, and a speaker ( 7030), etc. The display portion 7001 has a curved display surface and may display a display along the curved display surface. In addition, this portable information terminal can make a hands-free call by mutually communicating with a headset capable of wireless communication, for example. In addition, through the connection terminal 7024, data can be exchanged or charged with other information terminals. The charging operation can also be performed by wireless power supply.

The display portion 7001 mounted on the housing 7000 that also serves as a bezel portion has a non-rectangular display area. The display unit 7001 may display an icon 7027 representing a time, other icons 7028, and the like. Further, the display portion 7001 may be a touch panel (input/output device) on which a touch sensor (input device) is mounted.

In addition, the smart watch shown in (G) of FIG. 4 may have various functions. For example, a function to display various information (still images, moving pictures, text images, etc.) on the display unit, a touch panel function, a function to display a calendar, date or time, etc., a function to control processing by various software (programs), The wireless communication function, the function of connecting to various computer networks using the wireless communication function, the function of transmitting and receiving various data using the wireless communication function, the function of reading programs or data recorded in the recording medium and displaying them on the display unit, etc. Can have.

In addition, the speaker and sensors (force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical, voice, time, hardness, electric field, current, voltage) inside the housing 7000 , Power, radiation, flow rate, humidity, gradient, vibration, smell, or including the function of measuring infrared light), a microphone, and the like.

In addition, the light emitting device of one embodiment of the present invention and the display device having the light emitting device of one embodiment of the present invention can be used in each display portion of the electronic device shown in the present embodiment, thereby realizing an electronic device with a long life.

Further, as an electronic device to which a light emitting device is applied, the foldable portable information terminal shown in Figs. 5A to 5C is exemplified. 5A shows the portable information terminal 9310 in an open state. In addition, FIG. 5B shows the portable information terminal 9310 in a state in the middle of changing from one of an open state and a folded state to the other. In addition, FIG. 5C shows the portable information terminal 9310 in a folded state. The portable information terminal 9310 is excellent in portability in the folded state, and has a wide display area without a seam in the unfolded state, so that the visibility of the display is excellent.

The display portion 9311 is supported by three housings 9315 connected by hinges 9313. Further, the display portion 9311 may be a touch panel (input/output device) on which a touch sensor (input device) is mounted. In addition, the display unit 9311 can be reversibly deformed from the open state to the folded state by bending between the two housings 9315 using the hinge 9313. Further, the light emitting device of one embodiment of the present invention can be used for the display portion 9311. In addition, it is possible to realize a long life electronic device. The display area 9312 of the display unit 9311 is a display area positioned on the side when the portable information terminal 9310 is folded. In the display area 9312, it is possible to display an information icon, a shortcut to a frequently used application or program, and the like, so that it is possible to smoothly check information and start an application.

Further, a vehicle to which a light emitting device is applied is shown in FIGS. 6A and 6B. That is, the light emitting device can be provided integrally with the automobile. Specifically, it can be applied to a light 5101 (including the rear part of the vehicle body) on the exterior of the vehicle shown in Fig. 6A, a wheel 5102 of a tire, a part or all of the door 5103, and the like. Further, it can be applied to the display portion 5104 on the inside of the vehicle shown in Fig. 6B, the steering wheel 5105, the shift lever 5106, the seat seat 5107, the inner rearview mirror 5108, and the like. In addition, it may be applied to a part of the window pane.

Thereby, an electronic device or automobile to which the light emitting device or display device of one embodiment of the present invention is applied can be obtained. Further, in that case, an electronic device with a long life can be realized. In addition, the applicable electronic devices and automobiles are not limited to those shown in the present embodiment, and can be applied in various fields.

In addition, the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in the other embodiments.

(Embodiment 6)

In this embodiment, a configuration of a lighting device manufactured by applying the light emitting device of one embodiment of the present invention or a light emitting device that is a part thereof will be described with reference to FIG. 7.

7A and 7B show an example of a cross-sectional view of a lighting device. In addition, FIG. 7A shows a bottom emission type lighting device that extracts light toward the substrate, and FIG. 7B illustrates a top emission type lighting device that extracts light toward the sealing substrate.

The lighting device 4000 shown in FIG. 7A has a light emitting device 4002 on a substrate 4001. In addition, a substrate 4003 having irregularities is provided outside the substrate 4001. The light emitting device 4002 has a first electrode 4004, an EL layer 4005, and a second electrode 4006.

The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. Further, an auxiliary wiring 4009 that is electrically connected to the first electrode 4004 may be provided. In addition, an insulating layer 4010 is formed on the auxiliary wiring 4009.

Further, the substrate 4001 and the sealing substrate 4011 are bonded by the seal material 4012. It is also preferred that a desiccant 4013 is provided between the sealing substrate 4011 and the light emitting device 4002. Further, since the substrate 4003 has the unevenness as shown in FIG. 7A, the extraction efficiency of light generated from the light emitting device 4002 can be improved.

The lighting device 4200 shown in FIG. 7B has a light emitting device 4202 on a substrate 4201. The light emitting device 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206.

The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. Further, an auxiliary wiring 4209 that is electrically connected to the second electrode 4206 may be provided. Further, an insulating layer 4210 may be provided under the auxiliary wiring 4209.

The substrate 4201 and the sealing substrate 4211 having irregularities are bonded to each other by the seal material 4212. Further, a barrier film 4213 and a planarization film 4214 may be provided between the sealing substrate 4211 and the light emitting device 4202. Further, since the sealing substrate 4211 has the unevenness as shown in Fig. 7B, the extraction efficiency of light generated by the light emitting device 4202 can be improved.

Further, examples of applications of these lighting devices include indoor lighting ceiling lamps. Ceiling lamps include direct ceiling type or embedded ceiling type. Further, such a lighting device is configured by combining a light emitting device with a housing or a cover.

In addition, it can be applied as a footlight that can increase safety by irradiating light on the floor to illuminate the feet. It is effective to use a footlight, for example, in a bedroom, a staircase, or a passage. In this case, the size or shape can be appropriately changed according to the area or structure of the room. Further, it may be a stationary lighting device configured by combining a light emitting device and a support.

It can also be applied as a sheet-type lighting device (sheet-type lighting). Because sheet-type lighting is used by attaching it to the wall, it can be used in a wide range of applications without taking up space. Also, it is easy to increase the area. It can also be used on a wall or housing having a curved surface.

In addition to the above, a light emitting device of one embodiment of the present invention or a light emitting device that is a part of the light emitting device of the present invention can be applied to a part of furniture installed indoors to obtain a lighting device having a function as a furniture.

As described above, various lighting devices to which a light emitting device is applied can be obtained. In addition, these lighting devices are assumed to be included in one embodiment of the present invention.

In addition, the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in the other embodiments.

(Example 1)

<<Synthesis Example 1>>

In this example, the organic compound of one embodiment of the present invention represented by the structural formula (100) of the first embodiment, 3-[(3-dibenzothiophen-4-yl)phenyl]-7-phenyl[1]benzo A method for synthesizing puro[3,2-c]pyridazine (abbreviation: 7Ph-3mDBtPBfpd) will be described. In addition, the structure of 7Ph-3mDBtPBfpd is shown below.

[Formula 19]

<Step 1; Synthesis of ethyl 2-(6-chloro-3-oxo-1-benzofuran-2-yl)-2-hydroxyacetate>

First, 24 mL of ethyl glyoxylate (polymer type) (47% toluene solution) was placed in a three-necked flask, the inside of the flask was purged with nitrogen, and 230 mL of toluene was added. In an ice bath, 0.54 g (4.7 mmol) of trifluoroacetic acid was added to the mixture and stirred at 0° C. for 30 minutes. To this, 30 g (178 mmol) of 6-chlorobenzofuran-3-one was added, the temperature was raised to 50° C., and heated and stirred for 39 hours. After the lapse of a predetermined time, the precipitated solid was suction filtered, and the solid was washed with water, ethanol, and toluene to obtain 7.2 g of a white solid as the target substance. Water was added to the filtrate obtained here, and the aqueous layer and the oil-fat layer were separated.

The organic layer was washed with saturated brine, anhydrous magnesium sulfate was added and dried, followed by natural filtration. The obtained filtrate was concentrated, and the obtained solid was washed with toluene to obtain 4.0 g of a white solid as the target substance. The filtrate obtained here was purified by silica gel column chromatography. Toluene was first used as the developing solvent, and finally, the polarity was gradually increased by increasing the amount of ethyl acetate added so that the ratio of toluene:ethyl acetate = 2:1. The obtained fraction was concentrated, and the obtained solid was washed with toluene to obtain 5.4 g of a white solid as the target substance (total 17 g, yield 52%). The synthesis scheme of step 1 is shown in Equation (a-1) below.

[Formula 20]

<Step 2; Synthesis of 7-chloro[1]benzofuro[3,2-c]pyridazin-3-one>

Next, ethyl 2-(6-chloro-3-oxo-1-benzofuran-2-yl)-2-hydroxyacetate 22 g (81 mmol) obtained in step 1 and 340 mL of ethanol were added to a three-necked flask, and thereto Hydrazine monohydrate 12 g (240 mmol) was added, stirred at room temperature overnight, and then heated to reflux for 40 hours. The obtained reaction mixture was poured into water and stirred at room temperature. The mixture was filtered with suction, and the solid was washed with ethanol to obtain 5.5 g of a light orange solid as the target substance in a yield of 30%. The synthesis scheme of step 2 is shown in Equation (a-2) below.

[Formula 21]

<Step 3; Synthesis of 3,7-dichloro[1]benzofuro[3,2-c]pyridazine>

Next, 5.5 g (25 mmol) of 7-chloro[1]benzofuro[3,2-c]pyridazin-3-one obtained in step 2 and 80 mL of toluene were added to a three-necked flask, and phosphoryl chloride 19g (125mmol) and 0.1 mL of dimethylformamide were added and heated to reflux for 12 hours.

The obtained reaction mixture was neutralized by adding little by little to an aqueous sodium hydroxide solution in an ice bath. The aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene. The obtained organic layer was washed with a saline solution, and dried by adding anhydrous magnesium sulfate. The obtained mixture was filtered naturally, and the filtrate was concentrated to obtain a solid. This solid was dissolved in heated toluene, and filtered with suction through a filter medium stacked in the order of celite, alumina, and celite. The obtained filtrate was concentrated, and the solid was washed with ethanol to obtain 3.7 g of a white solid as a target substance in a yield of 63%. The synthesis scheme of step 3 is shown in the following equation (a-3).

[Formula 22]

<Step 4; Synthesis of 7-chloro-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine>

Next, 3.1 g (13 mmol) of 3,7-dichloro[1]benzofuro[3,2-c]pyridazine obtained in step 3, 3-(dibenzothiophen-4-yl)phenylboronic acid 4.4g (14mmol), tripotassium phosphate 9.1g (43mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-phos) 0.22g (0.52mmol), xylene 130mL It was put into a reaction container, and the inside of the reaction container was degassed, and nitrogen substitution was carried out. 63mg (0.28mmol) of palladium (II) acetate was added to the mixture, followed by heating and stirring at 120°C for 12 hours. S-phos 0.22g (0.52mmol) and palladium (II) acetate 63mg (0.28mmol) were added, followed by heating and stirring at 130°C for 8.5 hours. 3-(dibenzothiophen-4-yl)phenylboronic acid 0.95g (3.1mmol), tripotassium phosphate 2.0g (9.4mmol), S-phos 0.21g (0.52mmol), palladium (II) 59mg (0.27 mmol) was further added, followed by heating and stirring at 130° C. for 14 hours. Here, 3-(dibenzothiophen-4-yl)phenylboronic acid 0.95g(3.1mmol), tripotassium phosphate 2.0g(9.4mmol), S-phos 0.21g(0.52mmol), palladium(II) acetate 54mg (0.24mmol) was further added and heated and stirred at 130° C. for 7 hours. Here, 3-(dibenzothiophen-4-yl)phenylboronic acid 0.95g(3.1mmol), tripotassium phosphate 1.9g(9.0mmol), S-phos 0.23g(0.56mmol), palladium(II) acetate 71mg (0.32mmol) was further added, followed by heating and stirring at 130°C for 4 hours. The obtained reaction mixture was suction filtered, and the solid was washed with water and ethanol. This solid was dissolved in heated toluene, 90 g of alumina was added, followed by heating and stirring at 90°C. The mixture was suction filtered through celite and washed with heated toluene. The obtained filtrate was concentrated to obtain a brown solid. This solid was recrystallized using toluene to obtain 1.6 g of a white solid as the target substance in a yield of 27%. The synthesis scheme of step 4 is shown in Equation (a-4) below.

[Formula 23]

<Step 5; Synthesis of 3-[3-dibenzothiophen-4-yl]phenyl]-7-phenyl[1]benzofuro[3,2-c]paridazine (abbreviation: 7Ph-3mDBtPBfpd)>

Next, 0.53 g (1.1 mmol) of 7-chloro-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine obtained in step 4, Phenylboronic acid 0.18 g (1.4 mmol), cesium fluoride 0.62 g (4.1 mmol), and xylene 30 mL were placed in a reaction vessel, and the inside of the vessel was purged with nitrogen. After the mixture was heated to 60° C. while stirring, tris(dibenzylideneacetone)dipalladium(0)27mg(0.029mmol), 2'-(dicyclohexylphosphino)acetophenoneethylene ketal 25mg(0.069mmol) Was added, the temperature was raised to 110° C., and heated and stirred for 23 hours.

After a predetermined period of time, tris (dibenzylideneacetone) dipalladium (0) 25 mg (0.029 mmol), 2'- (dicyclohexylphosphino) acetophenone ethylene ketal 26 mg (0.069 mmol) was added to the mixture, It was heated and stirred at 120° C. for 39 hours.

After a predetermined period of time, the mixture was added to this mixture: 0.086 g (0.70 mmol) of phenylboronic acid, 0.3 g (2.0 mmol) of cesium fluoride, tris (dibenzylideneacetone) dipalladium (0) 12 mg (0.013 mmol), 2'- (Dicyclohexylphosphino) acetophenoneethylene ketal 13mg (0.036mmol) was added, followed by heating and stirring for 13 hours.

Water was added to the obtained mixture, suction filtered, and the solid was washed with ethanol. This solid was dissolved in heated toluene, and filtered with suction through a filter medium stacked in the order of celite, alumina, and celite. The obtained filtrate was concentrated to obtain a solid. This solid was recrystallized using toluene to obtain a white solid as a target substance in 0.23 g and a yield of 40%. The synthesis scheme of step 5 is shown in the following equation (a-5).

[Formula 24]

The analysis results of the white solid obtained in step 5 by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) are shown below. In addition, the ¹ H-NMR chart is shown in FIG. 8. From this result, it was found that in this Example, an organic compound, 7Ph-3mDBtPBfpd, which is one embodiment of the present invention represented by the above-described structural formula (100), was obtained.

¹ H-NMR.δ(CDCl ₃ ): 7.44-7.55 (m, 5H), 7.60-7.64 (m, 2H), 7.71-7.76 (m, 3H), 7.80 (dd, 1H), 7.86-7.88 (m) , 2H), 7.92 (ddd, 1H), 8.05 (s, 1H), 8.21-8.24 (m, 2H), 8.32 (d, 1H), 8.51 (d, 1H), 8.57 (dd, 1H).

<<About the properties of 7Ph-3mDBtPBfpd>>

Next, the ultraviolet-visible absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and emission spectrum of the toluene solution of 7Ph-3mDBtPBfpd were measured. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, V550 type) was used. In addition, for the measurement of the emission spectrum, a fluorescence photometer (manufactured by Hamamatsu Photonics K.K., FS920) was used. Fig. 9 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity.

From the results of Fig. 9, in the toluene solution of 7Ph-3mDBtPBfpd, absorption peaks were observed in the vicinity of 333 nm and 281 nm, and the emission wavelength peak was observed in the vicinity of 449 nm.

Next, the phosphorescence spectrum of the toluene solution of 7Ph-3mDBtPBfpd was measured. The phosphorescence spectrum was obtained by using an absolute PL quantum yield measuring device (manufactured by Hamamatsu Photonics KK, C11347-01), and a toluene deoxygenated solution in a glove box (manufactured by Bright Co., Ltd., LABstarM13 (1250/780)) under nitrogen atmosphere. Was placed in a quartz cell and measured at liquid nitrogen temperature in a manner of sealing. Fig. 10 shows the measurement results of the obtained phosphorescence spectrum. The horizontal axis represents the wavelength, and the vertical axis represents the emission intensity.

From the results of Fig. 10, in the toluene solution of 7Ph-3mDBtPBfpd at liquid nitrogen temperature, a phosphorescence spectrum was observed at 479 nm.

The organic compound, 7Ph-3mDBtPBfpd, which is one embodiment of the present invention, has a high T1 level and can be said to be a suitable host material for a phosphorescent material (guest material) emitting light in the vicinity of green. In addition, the organic compound, 7Ph-3mDBtPBfpd, which is one embodiment of the present invention can be used as a host material or a light-emitting material of a visible phosphorescent light-emitting material.

(Example 2)

<<Synthesis Example 2>>

In this example, the organic compound of one embodiment of the present invention represented by the structural formula (101) of the first embodiment, 7-(1,1'-biphenyl-3-yl)-3-[3-(dibenzothione A method for synthesizing ofen-4-yl)phenyl][1]benzofuro[3,2-c]pyridazine (abbreviation: 7mBP-3mDBtPBfpd) will be described. In addition, the structure of 7mBP-3mDBtPBfpd is shown below.

[Formula 25]

<Step 1; Synthesis of 7mBP-3mDBtPBfpd>

7-chloro-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2-c]pyrried obtained in step 4 of Example 1 (Synthesis Example 1) described above Chopped 1.6 g (3.5 mmol), 3-biphenylboronic acid 0.71 g (3.5 mmol), tripotassium phosphate 2.2 g (11 mmol), diglyme 35 mL, tert-butanol 0.79 g (11 mmol) were added to the reaction vessel, The inside of the container was degassed and replaced with nitrogen.

The mixture was heated to 60°C, and palladium (II) acetate 16 mg (0.070 mmol), di (1-adamantyl) -n-butylphosphine (cataCXium (registered trademark) A) 50 mg (0.14 mmol) were added, It was heated and stirred at 90° C. for 6.5 hours. Here, palladium (II) acetate 8 mg (0.035 mmol) and cataCXium A 25 mg (0.070 mmol) were further added, followed by heating and stirring at 90° C. for 8 hours. Water was added to the obtained reaction mixture, and the solid was suction filtered and washed with ethanol. This solid was dissolved in heated toluene, and filtered with suction through a filter medium in which Celite, alumina, and Celite were laminated.

The obtained filtrate was concentrated to obtain an oily substance. This oily substance was purified by silica gel column chromatography. Toluene was first used as the developing solvent, and then a mixed solvent of toluene:ethyl acetate = 9:1 was used. Ethanol was added to the oily substance obtained by concentrating the obtained fraction, followed by irradiation with ultrasonic waves to precipitate a solid. By suction filtration of this solid, a white solid as the target substance was obtained in 1.45 g and a yield of 71%. The synthesis scheme of step 1 is shown in Equation (b-1) below.

[Formula 26]

1.4 g of the obtained white solid was purified by sublimation by a train sublimation method. The conditions for sublimation purification were heating the solid at a pressure of 2.13 Pa and a heating temperature of 325°C. After sublimation purification, 0.72 g of the recovered white solid was sublimated and purified again. Conditions for sublimation purification were carried out at a pressure of 2.45 Pa and a heating temperature of 310°C. After sublimation purification, the target substance, 7-(1,1'-biphenyl-3-yl)-3-[3-(dibenzothiophen-4-yl)phenyl][1]benzofuro[3,2 -c]pyridazine (abbreviation: 7mBP-3mDBtPBfpd) was obtained in a yield of 0.57 g (white solid, recovery rate 79%).

The analysis results of the white solid obtained in step 1 by nuclear magnetic resonance spectroscopy ( ¹ H-NMR) are shown below. In addition, a ¹ H-NMR chart is shown in FIG. 11. From this result, it was found that in this Example, an organic compound, 7mBP-3mDBtPBfpd, which is one embodiment of the present invention represented by the above-described structural formula (101), was obtained.

¹ H-NMR.δ(CD ₂ Cl ₂ ): 7.39-7.42 (m, 1H), 7.49-7.54 (m, 4H), 7.60-7.79 (m, 8H), 7.89-7.91 (m, 2H), 7.93 (ddd, 1H), 7.97-7.98(m, 2H), 8.10(s, 1H), 8.25-8.27(m, 2H), 8.31(d, 1H), 8.52(d, 1H), 8.60(t, 1H) ).

<<About the properties of 7mBP-3mDBtPBfpd>>

Next, the ultraviolet and visible absorption spectrum (hereinafter simply referred to as'absorption spectrum') and emission spectrum of the toluene solution of 7mBP-3mDBtPBfpd were measured. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, V550 type) was used. In addition, for the measurement of the emission spectrum, a fluorescence photometer (manufactured by JASCO Corporation, FP8600) was used. Fig. 12 shows the measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity.

From the results of Fig. 12, in the toluene solution of 7mBP-3mDBtPBfpd, absorption peaks were observed around 333 nm and 281 nm, and peaks of emission wavelength were observed around 368 nm.

The organic compound, 7mBP-3mDBtPBfpd, which is one embodiment of the present invention, has a high T1 level and can be said to be a suitable host material for a phosphorescent material (guest material) emitting light in the vicinity of green. In addition, the organic compound, 7mBP-3mDBtPBfpd, which is one embodiment of the present invention can be used as a host material or a light-emitting material of a phosphorescent light-emitting material in a visible region.

101: first electrode
102: second electrode
103: EL layer
103a, 103b: EL layer
104: charge generation layer
111, 111a, 111b: hole injection layer
112, 112a, 112b: hole transport layer
113, 113a, 113b: light emitting layer
114, 114a, 114b: electron transport layer
115, 115a, 115b: electron injection layer
200R, 200G, 200B: optical distance
201: first substrate
202: transistor (FET)
203R, 203G, 203B, 203W: light emitting device
204: EL layer
205: second substrate
206R, 206G, 206B: Color filter
206R', 206G', 206B': color filter
207: first electrode
208: second electrode
209: black layer (black matrix)
210R, 210G: conductive layer
301: first substrate
302: pixel portion
303: driving circuit unit (source line driving circuit)
304a, 304b: driving circuit portion (gate line driving circuit)
305: Reality
306: second substrate
307: lead wiring
308: FPC
309: FET
310: FET
311: FET
312: FET
313: first electrode
314: insulation
315: EL layer
316: second electrode
317: light emitting device
318: area
900: substrate
901: first electrode
902: EL layer
903: second electrode
911: hole injection layer
912: hole transport layer
913: light emitting layer
914: electron transport layer
915: electron injection layer
4000: lighting device
4001: substrate
4002: light emitting device
4003: substrate
4004: first electrode
4005: EL layer
4006: second electrode
4007: electrode
4008: electrode
4009: auxiliary wiring
4010: insulating layer
4011: sealing substrate
4012: Reality
4013: desiccant
4015: diffuser plate
4200: lighting device
4201: substrate
4202: light emitting device
4204: first electrode
4205: EL layer
4206: second electrode
4207: electrode
4208: electrode
4209: auxiliary wiring
4210: insulating layer
4211: sealing substrate
4212: Reality
4213: barrier membrane
4214: planarization film
4215: diffuser plate
5101: light
5102: wheel cover
5103: Doa
5104: display
5105: handle
5106: shift lever
5107: seat seat
5108: rearview mirror
7000: housing
7001: display
7002: second display unit
7003: speaker
7004: LED lamp
7005: operation keys
7006: connection terminal
7007: sensor
7008: microphone
7009: switch
7010: infrared port
7011: recording medium reading unit
7014: antenna
7015: shutter button
7016: award
7018: stand
7020: camera
7022, 7023: control button
7024: connection terminal
7025: band
7026: microphone
7029: sensor
7030: speaker
7052, 7053, 7054: information
9310: portable information terminal
9311: display
9312: display area
9313: hinge
9315: housing

Claims (15)

Organic compound represented by general formula (G1):
[Formula 1]

In the above general formula (G1)
Q represents oxygen or sulfur,
A is a group having a total carbon number of 12 to 100, and a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, and a heteroaromatic ring including a dibenzofuran ring , Has any one or more of a hetero-aromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure,
R ¹ to R ⁵ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, or It represents an unsubstituted C6-C13 aryl group, or a substituted or unsubstituted C3-C12 heteroaryl group. Organic compound represented by general formula (G2):
[Formula 2]

In the above general formula (G2)
Q represents oxygen or sulfur,
α represents a substituted or unsubstituted phenylene group,
n represents an integer of 0 to 4,
Ht _uni represents a skeleton having hole transport properties,
R ¹ to R ⁵ are hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted It represents a C6-C13 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group. Organic compound represented by general formula (G3):
[Formula 3]

In the above general formula (G3)
Q represents oxygen or sulfur,
Ht _uni represents a skeleton having hole transport properties,
R ¹ to R ⁵ are hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, a substituted or unsubstituted It represents a C6-C13 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group. The method according to claim 2 or 3,
The Ht _uni has any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure, an organic compound. The method according to any one of claims 2 to 4,
The Ht _uni is an organic compound represented by any one of the following general formulas (Ht-1) to (Ht-26):
[Formula 4]

[Formula 5]

In the above general formula (Ht-1) to general formula (Ht-26)
Q represents oxygen or sulfur,
R ² to R ⁷¹ each represents a substituent of 1 to 4, independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, and any one of a substituted or unsubstituted phenyl group,
Ar ¹ represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. An organic compound represented by any one of structural formula (100) and structural formula (101).
[Formula 6]

As a light emitting device,
A light emitting device using the organic compound according to any one of claims 1 to 6. As a light emitting device,
Have an EL layer between a pair of electrodes,
The light emitting device, wherein the EL layer has the organic compound according to any one of claims 1 to 6. As a light emitting device,
Have an EL layer between a pair of electrodes,
The EL layer has a light emitting layer,
A light-emitting device, wherein the light-emitting layer has the organic compound according to any one of claims 1 to 6. As a light emitting device,
Have an EL layer between a pair of electrodes,
The EL layer has a light emitting layer,
A light-emitting device comprising the organic compound according to any one of claims 1 to 6 and a phosphorescent material. As a light emitting device,
Have an EL layer between a pair of electrodes,
The EL layer has a light emitting layer,
A light emitting device comprising the organic compound according to any one of claims 1 to 6, a phosphorescent material, and a carbazole derivative. The method of claim 11,
The carbazole derivative is a bicarbazole derivative, a light emitting device. As a light emitting device,
The light emitting device according to any one of claims 7 to 12, and
At least one of a transistor and a substrate
Having, a light-emitting device. As an electronic device,
The light emitting device according to claim 13,
At least one of a microphone, a camera, a button for operation, an external connection, and a speaker
With, electronic device. As a lighting device,
The light emitting device according to any one of claims 7 to 12, and
At least one of a housing, a cover, and a support
With, lighting device.

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