JP2021024863A - Organic compound, light-emitting device, light-emitting apparatus, electronic device and lighting device - Google Patents

Abstract

To provide a novel benzofuropyridazine derivative and to provide a light-emitting device using the compound, and the like.SOLUTION: There is provided an organic compound represented by the following formula. In the formula, Q represents O or S; A is a group having the total carbon number of 12 to 100 and is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring or the like; and R1 to R5 each independently represent H, a 1-6C alkyl group, a 5-7C monocyclic saturated hydrocarbon, a 7-10C polycyclic saturated hydrocarbon, a 6-13C aryl group or a 3-12C heteroaryl group.SELECTED DRAWING: None

Description

One aspect of the present invention relates to organic compounds, light emitting devices, light emitting devices, electronic devices, and lighting devices. However, one aspect of the present invention is not limited to the above technical fields. That is, one aspect of the present invention relates to an object, a method, a manufacturing method, or a driving method. Alternatively, one aspect of the invention relates to a process, machine, manufacture, or composition (composition of matter). Further, specifically, a semiconductor device, a display device, a liquid crystal display device, and the like can be mentioned as an example.

A light emitting device (also called an organic EL element) having an EL layer sandwiched between a pair of electrodes has characteristics such as thinness and light weight, high-speed response to an input signal, and low power consumption. Therefore, a display to which these are applied is available. , The speed of technological development is fast, and it is attracting a lot of attention.

In the light emitting device, by applying a voltage between a pair of electrodes, the electrons and holes injected from each electrode are recombined in the EL layer, and the luminescent substance (organic compound) contained in the EL layer is excited. It emits light when the excited state returns to the ground state. There are two types of excited states: singlet excited state (S ^* ) and triplet excited state (T ^* ). Emission from the singlet excited state is fluorescence, and emission from the triplet excited state is phosphorescence. being called. Moreover, it is considered that their statistical generation ratio in the light emitting device is S ^* : T ^* = 1: 3. The emission spectrum obtained from a luminescent substance is unique to that luminescent substance, and by using different types of organic compounds as the luminescent substance, luminescent devices having various luminescent colors can be obtained.

With respect to such a light emitting device, in order to improve the element characteristics, improvement of the element structure, material development and the like are actively carried out (see, for example, Patent Document 1).

Japanese Unexamined Patent Publication No. 2010-182699

Therefore, in one aspect of the present invention, a novel organic compound is provided. Further, in one aspect of the present invention, a novel organic compound having a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton is provided. Further, in one aspect of the present invention, a novel organic compound that can be used for a light emitting device is provided. Further, in one aspect of the present invention, a novel organic compound that can be used for the EL layer of a light emitting device is provided. Further, a novel highly reliable light emitting device using a novel organic compound which is one aspect of the present invention is provided. It also provides new light emitting devices, new electronic devices, or new lighting devices. The description of these issues does not prevent the existence of other issues. It should be noted that one aspect of the present invention does not necessarily have to solve all of these problems. Issues other than these are naturally clarified from the description of the description, drawings, claims, etc., and it is possible to extract issues other than these from the description of the description, drawings, claims, etc. Is.

One aspect of the present invention is a benzoflopyridazine derivative, which is an organic compound represented by the following general formula (G1). The organic compound represented by the following general formula (G1) has a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton.

In the above general formula (G1), Q represents oxygen or sulfur. Further, A is a group having a total carbon number of 12 to 100, and contains a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, and a carbazole. It has one or more of a heteroaromatic ring including a ring, a benzoimidazole ring, and a triphenylamine structure. In addition, R ^{1 to} R ⁵ are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, and a substituted or unsubstituted carbon number 7 to 7. It represents 10 polycyclic saturated hydrocarbons, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms.

Another aspect of the present invention is a benzoflopyridazine derivative, which 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 a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton.

In the above 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 a hole transporting property. Further, 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, and a large number of substituted or unsubstituted carbon atoms 7 to 10. Represents a cyclic saturated 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.

Another aspect of the present invention is a benzoflopyridazine derivative, which 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 a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton.

In the above general formula (G3), Q represents oxygen or sulfur. In addition, Ht _uni represents a skeleton having a hole transporting property. Further, 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, and a large number of substituted or unsubstituted carbon atoms 7 to 10. Represents a cyclic saturated 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.

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

_{Further, in each of the above configurations, Ht uni} in the above general formulas (G2) and (G3) is independently represented by any one of the following general formulas (Ht-1) to (Ht-26).

In the above general formulas (Ht-1) to (Ht-26), Q represents oxygen or sulfur. Further, R ^{2 to} R ⁷¹ each represent 1 to 4 substituents, and independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group. Further, 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 the structural formulas (100) and (101).

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, a light emitting device having a guest material in addition to the above organic compound is also included in the present invention.

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. The present invention also includes an EL layer held between a pair of electrodes and a light emitting device formed by using an organic compound according to an aspect of the present invention in a light emitting layer contained in the EL layer. Further, in addition to the above-mentioned light emitting device, a case where a layer having an organic compound (for example, a cap layer) in contact with an electrode is included in the light emitting device is also included in the present invention. Further, in addition to the light emitting device, a light emitting device having a transistor, a substrate and the like is also included in the category of the invention. Further, in addition to these light emitting devices, electronic devices and lighting devices having a microphone, a camera, an operation button, an external connection portion, a housing, a cover, a support base, a speaker, or the like are also included in the scope of the invention.

Further, one aspect of the present invention includes a light emitting device having a light emitting device, and further includes a lighting device having a light emitting device in the category. Therefore, the light emitting device in the present specification refers to an image display device or a light source (including a lighting device). Further, a module in which a connector such as FPC (Flexible printed circuit) or TCP (Tape Carrier Package) is attached to the light emitting device, a module in which a printed wiring board is provided at the end of TCP, or a COG (Chip On) in the light emitting device. The light emitting device also includes all modules in which an IC (integrated circuit) is directly mounted by the Glass) method.

In one aspect of the invention, a novel organic compound can be provided. Further, in one aspect of the present invention, it is possible to provide a novel organic compound having a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton. Moreover, in one aspect of the present invention, it is possible to provide a novel organic compound that can be used for a light emitting device. Moreover, in one aspect of the present invention, it is possible to provide a novel organic compound that can be used for the EL layer of a light emitting device. Further, by using a novel organic compound which is one aspect of the present invention, a highly reliable novel light emitting device can be provided. It is also possible to provide a new light emitting device, a new electronic device, or a new lighting device.

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

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

Note that the positions, sizes, ranges, etc. of each configuration shown in the drawings and the like may not represent the actual positions, sizes, ranges, etc. for the sake of easy understanding. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings and the like.

Further, in the present specification and the like, in explaining the structure of the invention using drawings, reference numerals indicating the same thing are commonly used among different drawings.

(Embodiment 1)
In the present embodiment, the organic compound which is one aspect of the present invention will be described. The organic compound according to one aspect of the present invention is an organic compound having a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton represented by the following general formula (G1). is there.

In the general formula (G1), Q represents oxygen or sulfur. Further, A is a group having a total carbon number of 12 to 100, and contains a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, and a carbazole. It has one or more of a heteroaromatic ring including a ring, a benzoimidazole ring, and a triphenylamine structure. In addition, R ^{1 to} R ⁵ are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, and a substituted or unsubstituted carbon number 7 to 7. It represents 10 polycyclic saturated hydrocarbons, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms.

Further, another aspect of the present invention is an organic compound represented by the following general formula (G2). The organic compound according to one aspect of the present invention is located at the 3-position of a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton as represented by the following general formula (G2). Has a hole-transporting skeleton.

In the above 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 a hole transporting property. Further, 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, and a large number of substituted or unsubstituted carbon atoms 7 to 10. Represents a cyclic saturated 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.

Further, another aspect of the present invention is an organic compound represented by the following general formula (G3). The organic compound according to one aspect of the present invention is located at the 3-position of a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton as represented by the following general formula (G3). Has a hole-transporting skeleton.

In the above general formula (G3), Q represents oxygen or sulfur. In addition, Ht _uni represents a skeleton having a hole transporting property. Further, 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, and a large number of substituted or unsubstituted carbon atoms 7 to 10. Represents a cyclic saturated 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.

_{The Ht uni} in the general formulas (G2) and (G3) independently have any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure.

_{Further, Ht uni} in the above general formulas (G2) and (G3) is independently represented by any one of the following general formulas (Ht-1) to (Ht-26).

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

In the above general formulas (G1), (G2), and (G3), a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms and a plurality of substituted or unsubstituted monocyclic saturated hydrocarbons having 7 to 10 carbon atoms. When a cyclic saturated 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. Alkyl groups having 1 to 7 carbon atoms such as ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group, cyclopentyl group, cyclohexyl group and cyclo Cycloalkyl groups with 5 to 7 carbon atoms such as heptyl group, 8,9,10-trinorbornanyl group, aryl groups with 6 to 12 carbon atoms such as phenyl group, naphthyl group and biphenyl group, and Examples thereof include a heteroaryl group having 6 to 13 carbon atoms such as a dibenzothiophenyl group, a dibenzofuranyl group and a carbazolyl group.

Similarly, the general formula (G1), specific examples of when referring to (G2), and ^{R 1} to ^{R 5} in (G3), a monocyclic saturated hydrocarbon 5-7 carbon atoms, cyclopentyl, cyclohexyl Groups, 1-methylcyclohexyl groups, cycloheptyl groups and the like can be mentioned.

Similarly, the general formula (G1), specific examples of when referring to (G2), and ^{R 1} to ^{R 5} in (G3), polycyclic saturated hydrocarbon having 7 to 10 carbon atoms, norbornyl group, adamantyl Examples include a group, a decalin group, and a tricyclodecyl group.

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

^{Further, specific examples of the case where R 1 to} R ⁵ in the above general formulas (G1), (G2), and (G3) represent an alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, and a propyl group. , Isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, 3-methylpentyl group. , 2-Methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, and the like.

^{Further, specific examples of the case where R 1 to} R ⁵ in the above general formulas (G1), (G2), and (G3) represent a heteroaryl group having 3 to 12 carbon atoms include a triazinyl group, a pyrazinyl group, and a pyrimidinyl group. Examples thereof include a group, a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a benzothienyl group, a benzofuranyl group, an indolyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, and the like.

In addition, the organic compound which is one aspect of the present invention is obtained by the fact that ^{R 1 to} R ⁵ in the above general formulas (G1), (G2), and (G3) have a group represented by the above-mentioned specific example. It has high thermal stability and physicochemical stability. Among them, when R ³ has a group represented by the above-mentioned specific example, the thermal stability is improved due to its structure, and LUMO is stabilized to have high electron resistance. By manufacturing a light emitting device using this material, a highly reliable light emitting device can be obtained.

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

The organic compounds represented by the structural formulas (100) to (121) are examples of the organic compounds represented by the general formula (G1), but the organic compound according to one aspect of the present invention is the same. Not limited to.

<< Method for synthesizing an organic compound represented by the general formula (G1) >>
Next, a method for synthesizing an organic compound having a benzoflo [3,2-c] pyridazine skeleton or a benzothieno [3,2-c] pyridazine skeleton, which is one aspect of the present invention and is represented by the following general formula (G1). Will be described.

In the general formula (G1), Q represents oxygen or sulfur. Further, A is a group having a total carbon number of 12 to 100, and contains a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, and a carbazole. It has one or more of a heteroaromatic ring including a ring, a benzoimidazole ring, and a triphenylamine structure. In addition, R ^{1 to} R ⁵ are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, and a substituted or unsubstituted carbon number 7 to 7. It represents 10 polycyclic saturated hydrocarbons, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms.

The synthesis scheme (A) of the organic compound represented by the general formula (G1) is shown below. As shown in the synthetic scheme (A) below, the compound represented by the general formula (G1) is a halogen compound (A1) having a benzoflopyridazine skeleton or a benzothienopyridazine skeleton, a boronic acid compound (A2), and a boronic acid compound. It is obtained by reacting with (A3).

In synthetic scheme (A), Q represents oxygen or sulfur. Further, A is a group having a total carbon number of 12 to 100, and contains a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a heteroaromatic ring containing a dibenzofuran ring, and a carbazole. It has one or more of a heteroaromatic ring including a ring, a benzoimidazole ring, and a triphenylamine structure. In addition, R ^{1 to} R ⁵ are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms, and a substituted or unsubstituted carbon number 7 to 7. It represents 10 polycyclic saturated hydrocarbons, substituted or unsubstituted aryl groups having 6 to 13 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms. Further, X ¹ and X ² represent halogen, and chlorine, bromine or iodine is preferable. Y ¹ and Y ² represent boronic acid, boronic acid ester, cyclic triol borate salt and the like. Further, as the cyclic triol borate salt, a potassium salt or a sodium salt may be used in addition to the lithium salt.

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 in the halogen compound (A1) is hydrogen.} That is, an intermediate (B3) is obtained by reacting a halogenated benzofuran-3-one derivative or a benzothiophene-3-one derivative (B1) with a glyoxylic acid ester (B2), and then hydrazine monohydrate. The intermediate (B4) can be obtained by reacting with. By reacting this intermediate (B4) with a halogenating agent, a halogen compound (A1) having a benzoflopyridazine skeleton or a benzothienopyridazine skeleton can be synthesized.

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

The halogen compound (A1) used in the synthesis scheme (A) can also be synthesized by the method shown in the synthesis scheme (C) below. 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.

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

The compounds (A1), (A2), (A3), (B1), (B2), (B3), (C1), (C2), and compounds used in the above synthesis schemes (A) to (C), and Since various types of (C3) are commercially available or can be synthesized, many types of the organic compound represented by the general formula (G1) can be synthesized. Therefore, the organic compound of one aspect of the present invention is rich in variation.

Although an example of the method for synthesizing an organic compound according to one aspect of the present invention has been described above, the present invention is not limited to this, and may be synthesized by any other synthetic method.

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

(Embodiment 2)
In the present embodiment, the light emitting device using the organic compound shown in the first embodiment will be described with reference to FIG.

≪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.

Further, FIG. 1B has a plurality of EL layers (103a, 103b) between the pair of electrodes (two layers in FIG. 1B), and has a charge generation layer 104 between the EL layers. An example of a light emitting device having a laminated structure (tandem structure) is shown. The EL layers to be laminated are not limited to two layers, and may be three or more layers.

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

The charge generation layer 104 may be transparent to visible light from the viewpoint of light extraction efficiency (specifically, the transmittance of visible light to the charge generation layer 104 is 40% or more). preferable. Further, the charge generation layer 104 functions even if the conductivity is lower than that of the first electrode 101 and the second electrode 102.

Further, in FIG. 1C, the EL layer 103 shown in FIG. 1A (the same applies when the EL layers (103a, 103b) of FIG. 1B have a laminated structure) has a laminated structure. An example of the case is shown. However, in this case, the first electrode 101 functions as an anode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially laminated on the first electrode 101. Has. Even when a plurality of EL layers are provided as in the tandem structure shown in FIG. 1 (B), the EL layers are sequentially laminated from the anode side as shown in FIG. 1 (D). In addition, in FIG. 1D, each EL layer has a hole injection layer (111a, 111b), a hole transport layer (112a, 112b), a light emitting layer (113a, 113b), and electron transport. It has layers (114a, 114b) and electron injection layers (115a, 115b), respectively. 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 contained in the EL layer (103, 103a, 103b) may have a light emitting substance or a plurality of substances in an appropriate combination, respectively, and may be configured to obtain fluorescent light emission or phosphorescent light emission exhibiting a desired light emitting color. it can. Further, the light emitting layer 113 may have a laminated structure having different light emitting colors. In this case, different materials may be used for the luminescent substance and other substances used for the laminated light emitting layers. Further, different emission colors may be obtained from the plurality of EL layers (103a and 103b) shown in FIG. 1B. In this case as well, the luminescent substance and other substances used for each light emitting layer may be different materials. The organic compound according to one aspect of the present invention can be used for the light emitting layer 113.

Further, in the light emitting device according to one aspect of the present invention, the light emission obtained by the EL layer (103, 103a, 103b) may be resonated between both electrodes to enhance the obtained light emission. For example, in FIG. 1C, a micro-optical resonator (microcavity) structure is formed by using the first electrode 101 as a reflective electrode and the second electrode 102 as a semi-transmissive / semi-reflective electrode, and forming an EL layer. The light emission obtained from 103 can be enhanced.

When the first electrode 101 of the light emitting device is a reflective electrode having a laminated structure of a conductive material having reflectivity and a conductive material having translucency (transparent conductive film), a film of the transparent conductive film. Optical adjustment can be performed by controlling the thickness. Specifically, the distance between the first electrode 101 and the second electrode 102 is close to mλ / 2 (where m is a natural number) with respect to the wavelength λ of the light obtained from the light emitting layer 113. It is preferable to adjust so as to.

Further, 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 of the light emitting layer 113 can be obtained, and the first. Adjust the optical distance from the electrode 102 of 2 to the region (light emitting region) where the desired light of the light emitting layer 113 is obtained so as to be close to (2 m'+ 1) λ / 4 (however, m'is a natural number). It is preferable to do so. The light emitting region referred to here refers to a recombination region of holes and electrons in the light emitting layer 113.

By performing such optical adjustment, the spectrum of a 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 case, the optical distance between the first electrode 101 and the second electrode 102 is, strictly speaking, the total thickness from the reflection region of the first electrode 101 to the reflection region of the second electrode 102. it can. However, since it is difficult to precisely determine the reflection region of the first electrode 101 and the second electrode 102, it is assumed that arbitrary positions of the first electrode 101 and the second electrode 102 are reflection regions. It is assumed that the above-mentioned effect can be sufficiently obtained. Further, the optical distance between the first electrode 101 and the light emitting layer from which the desired light can be obtained is, strictly speaking, the optical distance between the reflection region at the first electrode 101 and the light emitting region at the light emitting layer where the desired light can be obtained. It can be said that it is a distance. However, since it is difficult to precisely determine the reflection region in the first electrode 101 and the light emission region in the light emitting layer where desired light can be obtained, an arbitrary position of the first electrode 101 can be set as the reflection region, which is desired. It is assumed that the above-mentioned effect can be sufficiently obtained by assuming that an arbitrary position of the light emitting layer from which light is obtained is a light emitting region.

When the light emitting device shown in FIG. 1C has a microcavity structure, light having a different wavelength (monochromatic light) can be extracted even if the EL layer is common. Therefore, it is not necessary to separately paint (for example, RGB) to obtain different emission colors, and high definition can be achieved. It can also be combined with a colored layer (color filter). In addition, since it is possible to increase the emission intensity in the front direction of a specific wavelength, it is possible to reduce power consumption.

The light emitting device shown in FIG. 1 (E) is an example of a light emitting device having a laminated structure (tandem structure) shown in FIG. 1 (B), and as shown in the figure, three EL layers (103a, 103b, 103c). Have a structure in which charges are laminated with the charge generation layers (104a, 104b) interposed therebetween. The three EL layers (103a, 103b, 103c) each have a light emitting layer (113a, 113b, 113c), and the emission colors of the light emitting layers can be freely combined. For example, the light emitting layer 113a may be blue, the light emitting layer 113b may be red, green, or yellow, and the light emitting layer 113c may be blue, but the light emitting layer 113a may be red and the light emitting layer 113b may be blue, green, or yellow. Either of the above, the light emitting layer 113c can be made red.

In the light emitting device according to one aspect of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is a translucent electrode (transparent electrode, semitransparent / semireflecting electrode, etc.). To do. When the electrode having translucency is a transparent electrode, the transmittance of visible light of the transparent electrode is 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the reflectance of visible light of the semi-transmissive / semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Further, these electrodes preferably have a resistivity of 1 × 10 ^-2 Ωcm or less.

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

≪Specific structure and manufacturing method of light emitting device≫
Next, a specific structure and a manufacturing method of the light emitting device shown in FIG. 1, which is one aspect of the present invention, will be described. Here, not only the light emitting device having the EL layer 103 having a single layer structure as shown in FIGS. 1 (A) and 1 (C), but also FIGS. 1 (B), 1 (D) and 1 (FIG. 1). The tandem structure light emitting device shown in E) will also be described collectively. 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 semitransmissive / semireflective electrode. Further, a desired electrode material may be used in a single layer or in a plurality of layers, and the electrode material can be formed in a single layer or laminated. Further, after forming the EL layer (103, 103b), the second electrode 102 is formed by selecting a material in the same manner as described above. Further, a sputtering method or a vacuum vapor deposition method can be used for producing these electrodes.

<1st electrode and 2nd electrode>
As the material for forming the first electrode 101 and the second electrode 102, the following materials can be appropriately combined and used as long as the functions of both electrodes described above can be satisfied. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be appropriately used. Specific examples thereof include In—Sn oxide (also referred to as ITO), In—Si—Sn oxide (also referred to as ITSO), In—Zn oxide, and In—W—Zn oxide. 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), Tantal (Ta), Tungsten (W), Palladium (Pd), Gold (Au), Platinum (Pt), Silver (Ag), Ittrium (Y) ), Metals such as neodymium (Nd), and alloys containing these in appropriate combinations can also be used. Other elements belonging to Group 1 or Group 2 of the Periodic Table of Elements not illustrated above (eg, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), europium (Eu), ytterbium Rare earth metals such as (Yb), alloys containing these in appropriate combinations, and other graphenes can be used.

In the light emitting device shown in FIG. 1, when the EL layer 103 having a laminated structure as shown in FIG. 1C and the first electrode 101 is an anode, the positive EL layer 103 is positively placed on the first electrode 101. The hole injection layer 111 and the hole transport layer 112 are sequentially laminated and formed by a vacuum vapor deposition method. Further, as shown in FIG. 1D, when a plurality of EL layers (103a, 103b) having a laminated structure are laminated with the charge generation layer 104 interposed therebetween and the first electrode 101 is an anode, the first electrode Not only the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are sequentially laminated and formed on the 101 by the vacuum deposition method, but also the EL layer 103a and the charge generation layer 104 are sequentially laminated and then charged. The hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are similarly laminated and formed on the layer 104 in the same manner.

<Hole injection layer and hole transport layer>
The hole injection layer (111, 111a, 111b) is a layer for injecting holes into the EL layer (103, 103a, 103b) from the first electrode 101 or the charge generation layer (104), which is the anode. , A layer containing a material with high hole injection properties.

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

In addition, low molecular weight compounds such as 4,4', 4''-tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4', 4''-tris [N- (3) -Methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 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-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation) : PCzPCA1), 3,6-bis [N- (9-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl)- Aromatic amine compounds such as N- (9-phenylcarbazole-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) can be used.

In addition, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4), which are polymer compounds (oligoforms, 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: Polymer-TPD) and the like can be used. Alternatively, a polymer system to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (abbreviation: PEDOT / PSS) or polyaniline / poly (styrene sulfonic acid) (Pani / PSS) is added. Compounds, etc. can also be used.

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

The hole transport layer (112, 112a, 112b) transports the holes injected from the first electrode 101 to the light emitting layer (113, 113a, 113b) by the hole injection layer (111, 111a, 111b). It is a layer. The hole transport layer (112, 112a, 112b) is a layer containing a hole transport material. As the hole transporting material used for the hole transporting layer (112, 112a, 112b), a material having the same or close HOMO level as the HOMO level of the hole injecting layer (111, 111a, 111b) should be used. Is preferable.

As the acceptor material used for the hole injection layers (111, 111a, 111b), oxides of metals belonging to Group 4 to Group 8 in the Periodic Table of the Elements can be used. Specific examples thereof include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide and rhenium oxide. Of these, molybdenum oxide is particularly preferable because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. As having an electron-withdrawing group (a halogen group or a cyano group) is _{7,7,8,8-(abbreviation:} F 4 -TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), 1,3,4,5,7,8-hexa Fluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ) and the like can be mentioned. In particular, a compound such as HAT-CN in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of complex atoms is thermally stable and preferable. Further, the [3] radialene derivative having an electron-withdrawing group (particularly a halogen group such as a fluoro group or a cyano group) is preferable because it has very high electron acceptability, and specifically, α, α', α''-. 1,2,3-Cyclopropanetriylidentris [4-cyano-2,3,5,6-tetrafluorobenzene acetonitrile], α, α', α''-1,2,3-cyclopropanetriiridentris [2,6-dichloro-3,5-difluoro-4- (trifluoromethyl) benzene acetonitrile], α, α', α''-1,2,3-cyclopropanetriylidentris [2,3,4 , 5,6-Pentafluorobenzene acetonitrile] and the like.

As the hole transporting material used for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 112b), the hole mobility at a square root of the electric field strength [V / cm] of 600 is A substance having a hole mobility of 1, 1 × 10 ^-6 cm ^{2 / Vs or more is preferable.} Any substance other than these can be used as long as it is a substance having a higher hole transport property than electrons.

As the hole transporting material, a material having a high hole transporting property such as a π-electron excess type 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 derivative (compound having a carbazole skeleton) include a carbazole derivative (for example, a 3,3'-bicarbazole derivative), an aromatic amine having a carbazolyl group, and the like.

Specific examples of the bicarbazole derivative (for example, 3,3'-bicarbazole derivative) include 3,3'-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), 9,9'. -Bis (1,1'-biphenyl-4-yl) -3,3'-bi-9H-carbazole, 9,9'-bis (1,1'-biphenyl-3-yl) -3,3'- Be-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 can be mentioned.

Specific examples of the aromatic amine having a carbazolyl group include 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBA1BP) and N- (4). -Biphenyl) -N- (9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazole-3-amine (abbreviation: PCBiF), N- (1,1'-biphenyl-4 -Il) -N- [4- (9-phenyl-9H-carbazole-3-yl) phenyl] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl -4''- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- (1-naphthyl) -4'-(9-phenyl-9H-carbazole-3-yl) ) Triphenylamine (abbreviation: PCBANB), 4,4'-di (1-naphthyl) -4''- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBNBB), 4- Phenyldiphenyl- (9-phenyl-9H-carbazole-3-yl) amine (abbreviation: PCA1BP), N, N'-bis (9-phenylcarbazole-3-yl) -N, N'-diphenylbenzene-1, 3-Diamine (abbreviation: PCA2B), N, N', N''-triphenyl-N, N', N''-tris (9-phenylcarbazole-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-carbazole-3-yl) phenyl] Spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 3- [N- (9-phenylcarbazole-) 3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (Abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9-phenylcarbazole-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), 3- [N- (4- (4-yl) Diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PC zDPA1), 3,6-bis [N- (4-diphenylaminophenyl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis [N- (4-diphenylaminophenyl) -N- (1-naphthyl) amino] -9-Phenylcarbazole (abbreviation: PCzTPN2), 2- [N- (9-Phenylcarbazole-3-yl) -N-Phenylamino] Spiro-9,9'-bifluorene (Abbreviation: PCASF), N- [4- (9H-carbazole-9-yl) phenyl] -N- (4-phenyl) phenylaniline (abbreviation: YGA1BP), N, N'-bis [4- (carbazole-) 9-Il) Phenyl] -N, N'-Diphenyl-9,9-Dimethylfluorene-2,7-Diamine (abbreviation: YGA2F), 4,4', 4''-Tris (carbazole-9-yl) tri Phenylamine (abbreviation: TCTA), and the like can be mentioned.

Examples of the carbazole derivative include 3- [4- (9-phenanthryl) -phenyl] -9-phenyl-9H-carbazole (abbreviation: PCPPn) and 3- [4- (1-naphthyl) -phenyl] in addition to the above. -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 can be mentioned.

Specific examples of the furan derivative (compound having a furan skeleton) include 4,4', 4''- (benzene-1,3,5-triyl) tri (dibenzothiophene) (abbreviation: DBT3P-II). ), 2,8-Diphenyl-4- [4- (9-phenyl-9H-fluorene-9-yl) phenyl] dibenzothiophene (abbreviation: DBTFLP-III), 4- [4- (9-phenyl-9H-) Fluorene-9-yl) phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and other compounds with a thiophene skeleton, 4,4', 4''-(benzene-1,3,5-triyl) tri (Dibenzofuran) (abbreviation: DBF3P-II), 4- {3- [3- (9-phenyl-9H-fluorene-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II) and the like can be mentioned.

Specific examples of the aromatic amines include 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD) and N, N'-bis. (3-Methylphenyl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine (abbreviation: TPD), 4,4'-bis [N- (spiro-9,9) '-Bifluoren-2-yl) -N-phenylamino] Biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl -3'-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP), N- (9,9-dimethyl-9H-fluoren-2-yl) -N- {9,9-dimethyl- 2- [N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl) amino] -9H-fluoren-7-yl} phenylamine (abbreviation: DFLADFL), N- (9, 9-Dimethyl-2-diphenylamino-9H-fluoren-7-yl) diphenylamine (abbreviation: DPNF), 2- [N- (4-diphenylaminophenyl) -N-phenylamino] spiro-9,9'-bifluorene (Abbreviation: DPASF), 2,7-bis [N- (4-diphenylaminophenyl) -N-phenylamino] -spiro-9,9'-bifluorene (abbreviation: DPA2SF), 4,4', 4'' -Tris [N- (1-naphthyl) -N-phenylamino] triphenylamine (abbreviation: 1'-TNATA), 4,4', 4''-tris (N, N-diphenylamino) triphenylamine ( Abbreviation: TDATA), 4,4', 4''-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: m-MTDATA), N, N'-di (p- Trill) -N, N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N , N'-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine (abbreviation: DNTPD), 1 , 3,5-Tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B) and the like.

Examples of the hole transporting material include poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), and poly [N- (4- {N'-[4- (4-Diphenylamino) phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) ) Benzidine] (abbreviation: Poly-TPD) and other high molecular compounds can also be used.

However, the hole-transporting material is not limited to the above, and the hole-injecting layer (111, 111a, 111b) and the hole-transporting layer can be combined as one or a plurality of known various materials as the hole-transporting material. It can be used for (112, 112a, 112b). The hole transport layers (112, 112a, 112b) may be formed from 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, a light emitting layer (113, 113a) is formed on the hole transport layer (112, 112a) of the EL layer (103, 103a) by a vacuum vapor deposition method. In the case of the light emitting device having the tandem structure shown in FIG. 1 (D), after the EL layer 103a and the charge generation layer 104 are formed, the light emitting layer 113b is also vacuumed on the hole transport layer 112b of the EL layer 103b. It is formed by a vapor deposition method.

<Light emitting layer>
The light emitting layer (113, 113a, 113b, 113c) is a layer containing a light emitting substance. As the luminescent substance, a substance exhibiting a luminescent color such as blue, purple, bluish purple, green, yellowish green, yellow, orange, and red is appropriately used. Further, by using different light emitting substances for a plurality of light emitting layers (113a, 113b, 113c), it is possible to obtain a configuration (for example, white light emission obtained by combining light emitting colors having complementary colors). .. Further, one light emitting layer may have a laminated structure having different light emitting substances.

Further, the light emitting layer (113, 113a, 113b, 113c) may have one or more kinds of organic compounds (host material, etc.) in addition to the light emitting substance (guest material). Further, as one or more kinds of organic compounds, one or both of the organic compound which is one aspect of the present invention and the hole transporting material and the electron transporting material described in the present embodiment can be used. ..

The luminescent material that can be used for the light emitting layer (113, 113a, 113b, 113c) is not particularly limited, and is a luminescent material that converts singlet excitation energy into light emission in the visible light region, or triplet excitation energy (basal state and triplet). A luminescent material that changes the energy difference from the term excited state) to luminescence in the visible light region can be used.

Examples of other luminescent substances include the following.

Examples of the luminescent substance that converts the single-term excitation energy into light emission include a substance that emits fluorescence (fluorescent material), and examples thereof include pyrene derivative, anthracene derivative, triphenylene derivative, fluorene derivative, carbazole derivative, dibenzothiophene derivative, dibenzofuran derivative, and dibenzo. Examples thereof include quinoxalin derivatives, quinoxalin derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, and naphthalene derivatives. In particular, the pyrene derivative is preferable because it has a high emission quantum yield. Specific examples of the pyrene derivative include N, N'-bis (3-methylphenyl) -N, N'-bis [3- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6. -Diamine (abbreviation: 1,6 mM FLPAPrn), N, N'-diphenyl-N, N'-bis [4- (9-phenyl-9H-fluoren-9-yl) phenyl] pyrene-1,6-diamine (abbreviation) : 1,6FLPAPrn), N, N'-bis (dibenzofuran-2-yl) -N, N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N, N'-bis (dibenzothiophene) -2-yl) -N, N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAprn), N, N'-(pyrene-1,6-diyl) bis [(N-phenylbenzo [b] ] Naft [1,2-d] furan) -6-amine] (abbreviation: 1,6BnfAPrn), N, N'-(pyrene-1,6-diyl) bis [(N-phenylbenzo [b] naphtho [b] naphtho [b] 1,2-d] furan) -8-amine] (abbreviation: 1,6BnfAPrn-02), N, N'-(pyrene-1,6-diyl) bis [(6, N-diphenylbenzo [b] naphtho) [1,2-d] furan) -8-amine] (abbreviation: 1,6BnfAPrn-03) and the like can be 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-carbazole-9-yl) phenyl] -N, N'-diphenyl Stillben-4,4'-diamine (abbreviation: YGA2S), 4- (9H-carbazole-9-yl) -4'-(10-phenyl-9-anthril) triphenylamine (abbreviation: YGAPA), 4- ( 9H-carbazole-9-yl) -4'-(9,10-diphenyl-2-anthryl) triphenylamine (abbreviation: 2YGAPPA), N, 9-diphenyl-N- [4- (10-phenyl-9-) Anthryl) phenyl] -9H-carbazole-3-amine (abbreviation: PCAPA), 4- (10-phenyl-9-anthril) -4'-(9-phenyl-9H-carbazole-3-yl) triphenylamine ( Abbreviation: PCBAPA), 4- [4- (10-phenyl-9-anthryl) phenyl] -4'-(9-phenyl-9H-carbazole-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- Carbazole-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.

Examples of the luminescent substance that converts triplet excitation energy into light emission include a substance that emits phosphorescence (phosphorescent material) and a thermally activated delayed fluorescence (TADF) material that exhibits thermally activated delayed fluorescence. ..

Examples of the phosphorescent material include an organometallic complex, a metal complex (platinum complex), and a rare earth metal complex. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as necessary.

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

For example, Tris {2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl) -4H-1,2,4-triazole-3-yl-κN2] phenyl-κC} iridium (III) ) (Abbreviation: [Ir (mpptz-dmp) ₃ ]), Tris (5-methyl-3,4-diphenyl-4H-1,2,4-triazolat) Iridium (III) (Abbreviation: [Ir (Mptz) _3] ]), Tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1,2,4-triazolate] iridium (III) (abbreviation: [Ir (iPrptz-3b) ₃ ]), Tris 4H-triazole skeleton such as [3- (5-biphenyl) -5-isopropyl-4-phenyl-4H-1,2,4-triazolate] iridium (III) (abbreviation: [Ir (iPr5btz) _3]). Tris [3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1,2,4-triazolat] iridium (III) (abbreviation: [Ir (Mptz1-mp) ₃₎ ]), 1H-triazole such as tris (1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolate) iridium (III) (abbreviation: [Ir (Prptz1-Me) _3]) Organic metal complex with skeleton, fac-tris [1- (2,6-diisopropylphenyl) -2-phenyl-1H-imidazole] iridium (III) (abbreviation: [Ir (iPrpmi) ₃ ]), tris [3- Organic with an imidazole skeleton such as (2,6-dimethylphenyl) -7-methylimidazole [1,2-f] phenanthridinato] iridium (III) (abbreviation: [Ir (dmimpt-Me) _3]) Metal complex, 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) Acetylacet Examples thereof include an organometallic complex having a phenylpyridine derivative having an electron-withdrawing group as a ligand, such as nat (abbreviation: FIR (acac)).

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

For example, tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) ₃ ]), tris (4-t-butyl-6-phenylpyrimidinato) iridium (III). (Abbreviation: [Ir (tBuppm) ₃ ]), (Acetylacetone) bis (6-methyl-4-phenylpyrimidinato) Iridium (III) (Abbreviation: [Ir (mppm) ₂ (acac)]), ( Acetylacetone) bis (6-tert-butyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (tBuppm) ₂ (acac)]), (acetylacetonato) bis [6- (2-) Norbornyl) -4-phenylpyrimidineat] iridium (III) (abbreviation: [Ir (nbppm) ₂ (acac)]), (acetylacetonato) bis [5-methyl-6- (2-methylphenyl) -4 -Phenylpyrimidinato] iridium (III) (abbreviation: [Ir (mpmppm) ₂ (acac)]), (acetylacetonato) bis {4,6-dimethyl-2- [6- (2,6-dimethylphenyl) ) -4-Pyrimidinyl-κN3] phenyl-κC} iridium (III) (abbreviation: [Ir (dmppm-dmp) ₂ (acac)]), (acetylacetonato) bis (4,6-diphenylpyrimidinato) iridium (III) (Abbreviation: [Ir (dppm) ₂ (acac)]), an organic metal iridium complex having a pyrimidine skeleton, (acetylacetonato) bis (3,5-dimethyl-2-phenylpyrazinato) iridium. (III) (abbreviation: [Ir (mppr-Me) ₂ (acac)]), (acetylacetone) bis (5-isopropyl-3-methyl-2-phenylpyrazinato) iridium (III) (abbreviation: [ An organic metal iridium complex having a pyrazine skeleton such as 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) acetylacetoneate (abbreviation: [Ir (ppy) ₂ (acac)]), bis (benzo [h] quinolinato) Iridium (III) Acetylacetoneate (abbreviation: [Ir (bzq) ₂ (acac)]), Tris (benzo [h] quinolinato) Iridium (III) (abbreviation: [Ir (abbreviation) bzq) ₃ ]), Tris (2- ^{phenylquinolinato-N, C 2'} ) Iridium (III) (abbreviation: [Ir (pq) ₃ ]), Bis (2-phenylquinolinato-N, C ^2' ) Iridium (III) Acetylacetoneate (abbreviation: [Ir (pq) ₂ (acac)]), Bis [2- (2-pyridinyl-κN) phenyl-κC] [2- (4-phenyl-2-pyridinyl-κN) ) Phenyl-κC] iridium (III) (abbreviation: [Ir (ppy) ₂ (4dppy)]), bis [2- (2-pyridinyl-κN) phenyl-κC] [2- (4-methyl-5-phenyl) -2-Pyridinyl-κN) phenyl-κC] -like organic metal iridium complex with a pyridine skeleton, 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) acetylacetoneate (abbreviation: [Ir) (P-PF-ph) ₂ (acac)]), bis (2-phenylbenzothiazolato-N, C ^2' ) iridium (III) acetylacetoneate (abbreviation: [Ir (bt) ₂ (acac)]] ) And other organic metal complexes, as well as rare earth metal complexes such as tris (acetylacetonato) (monophenanthrolin) terbium (III) (abbreviation: [Tb (acac) _{3 (Phen)]).}

Examples of the phosphorescent material having a yellow or red color and 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 (divm)]), bis [4,6-bis ( 3-Methylphenyl) pyrimidinato] (dipivaloylmethanato) iridium (III) (abbreviation: [Ir (5mdppm) ₂ (dpm)]), (dipivaloylmethanato) bis [4,6-di (naphthalene-) 1-yl) pyrimidinato] Iridium (III) (abbreviation: [Ir (d1npm) ₂ (dpm)]), an organic metal complex having a pyrimidine skeleton, (acetylacetonato) bis (2,3,5-triphenyl) Pyrazinenate) Iridium (III) (abbreviation: [Ir (tppr) ₂ (acac)]), bis (2,3,5-triphenylpyrazinato) (dipivaloylmethanato) iridium (III) (abbreviation : [Ir (tppr) ₂ (dpm)]), bis {4,6-dimethyl-2- [3- (3,5-dimethylphenyl) -5-phenyl-2-pyrazinyl-κN] phenyl-κC} ( 2,6-Dimethyl-3,5-Heptandionato-κ ² O, O') Iridium (III) (abbreviation: [Ir (dmdppr-P) ₂ (divm)]), bis {4,6-dimethyl-2- [5- (4-Cyano-2,6-dimethylphenyl) -3- (3,5-dimethylphenyl) -2-pyrazinyl-κN] phenyl-κC} (2,2,6,6-tetramethyl-3) , 5-Heptandionato-κ ² O, O') Iridium (III) (abbreviation: [Ir (dmdppr-dmCP) ₂ (dpm)]), (Acetylacetonato) bis [2-methyl-3-phenylquinoxarinato -N, C ^2' ] Iridium (III) (abbreviation: [Ir (mpq) ₂ (acac)]), (acetylacetonato) bis (2,3-diphenylquinoxarinato-N, C2 ^' ) iridium ( III) (abbreviation: [Ir (dpq) ₂ (acac)]), (acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III) (abbreviation: [Ir (Fdpq) ₂₎ (Acac)]) organic metal complexes with a pyrazine skeleton, tris (1-phenylisoquinolinato-N, C ^2' ) iridium (III) (abbreviation: [Ir (piq) ₃ ]), bis ( 1-Phenylisoquinolinato-N, C ^2' ) Iridium (III) ) Acetylacetonate (abbreviation: [Ir (piq) ₂ (acac)]), bis [4,6-dimethyl-2- (2-quinolinyl-κN) phenyl-κC] (2,4-pentandionato-κ) ² O, O') Organic metal complex having a pyridine skeleton such as iridium (III), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation) : [PtOEP]), platinum complex, tris (1,3-diphenyl-1,3-propanedionat) (monophenanthroline) europium (III) (abbreviation: [Eu (DBM) ₃ (Phen)]), Rare earth metal complexes such as tris [1- (2-tenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: [Eu (TTA) _{3 (Phen)])} Can be mentioned.

As the organic compound (host material, etc.) used for the light emitting layer (113, 113a, 113b, 113c), one or a plurality of substances having an energy gap larger than the energy gap of the light emitting substance (guest material) may be selected and used. Good.

Therefore, when the luminescent material used for the light emitting layer (113, 113a, 113b, 113c) is a fluorescent material, the energy level in the singlet excited state is large and triplet as the organic compound (host material) used in combination with the luminescent material. It is preferable to use an organic compound having a small energy level in the term excited state. Examples of the organic compound (host material) used in combination with the luminescent material include the organic compound according to one aspect of the present invention shown in the first embodiment and the hole transporting material (described above) shown in the present embodiment. And electron-transporting materials (described later), bipolar materials and the like can be used. By using the organic compound which is one aspect of the present invention shown in the first embodiment in the light emitting layer (particularly by using it as a host material), the initial deterioration of the light emitting device can be suppressed and the reliability can be improved. ..

Although some overlap with the above specific examples, specific examples of organic compounds are shown below from the viewpoint of a preferable combination with a luminescent substance (fluorescent material, phosphorescent material).

When the luminescent material is a fluorescent material, the organic compounds (host materials) that can be used in combination with the luminescent material include anthracene derivatives, tetracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, and dibenzo [g, p] chrysene derivatives. Such as condensed polycyclic aromatic compounds. Moreover, it is preferable to use the organic compound which is one aspect of the present invention shown in the first embodiment.

Specific examples of the organic compound (host material) used in combination with a fluorescent luminescent substance include 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: 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-carbazole -3-Amin (abbreviation: CzA1PA), 4- (10-phenyl-9-anthril) triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N, 9-diphenyl-N- {4- [4- (10) −Phenyl-9-anthryl) phenyl] phenyl} -9H-carbazole-3-amine (abbreviation: PCAPBA), N- (9,10-diphenyl-2-anthril) -N, 9-diphenyl-9H-carbazole-3 -Amin (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylcrisen, N, N, N', N', N'', N'', N''', N'''-octa Phenyldibenzo [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-anthril) phenyl] -7H-dibenzo [c, g] carbazole (abbreviation: cgDBCzPA), 6- [3- (9,10-diphenyl-2-anthril) phenyl] -Benzo [b] naphtho [1,2-d] furan (abbreviation: 2 mbnfPPA), 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'-(stillben-3,3'-diyl) diphenanthrene (abbreviation: t-BuDNA) Abbreviation: DPNS), 9,9'-(Stillbe) -4,4'-diyl) diphenanthrene (abbreviation: DPNS2), 1,3,5-tri (1-pyrenyl) benzene (abbreviation: TPB3), 5,12-diphenyltetracene, 5,12-bis (biphenyl) -2-yl) Tetracene and the like can be mentioned.

When the luminescent material is a phosphorescent material, an organic compound having a triplet excitation energy larger than the triplet excitation energy of the luminescent material may be selected as the organic compound (host material) used in combination with the luminescent material. In particular, the organic compound which is one aspect of the present invention shown in the first embodiment is suitable. When a plurality of organic compounds (for example, a first host material and a second host material (or an assist material)) are used in combination with a light emitting substance in order to form an excitation complex, these plurality of organic compounds are used. Is preferably mixed with a phosphorescent material.

With such a configuration, it is possible to efficiently obtain light emission using ExTET (Exciplex-Triplet Energy Transfer), which is an energy transfer from an excited complex to a luminescent substance. As a combination of a plurality of organic compounds, a compound that easily forms an excitation complex is preferable, and a compound that easily receives holes (hole transporting material) and a compound that easily receives electrons (electron transporting material) are combined. Is particularly preferred. The organic compound according to one aspect of the present invention shown in the first embodiment is suitable as a host material when the luminescent material is a phosphorescent material because the triplet excited state is stable. When forming the excitation complex as described above, it is suitable as an electron transporting material. Further, it is particularly suitable when used in combination with a phosphorescent material that emits green light due to its triplet excitation energy level.

When the luminescent material is a phosphorescent material, the organic compounds (host material, assist material) that can be used in combination with the luminescent material include aromatic amines, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, zinc and aluminum derivatives. Examples thereof include metal complexes, oxadiazole derivatives, triazole derivatives, benzoimidazole derivatives, quinoxalin derivatives, dibenzoquinoxalin derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives and the like.

Among the above, specific examples of aromatic amines (compounds having an aromatic amine skeleton), which are organic compounds having high hole transport properties, are the same as the specific examples of the hole transport materials shown above. Can be mentioned.

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

Specific examples of the dibenzothiophene derivative and the dibenzofuran derivative, which are organic compounds having high hole transport properties, include 4-{3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl] phenyl}. Dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4', 4''-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 1,3,5-tri (dibenzo) Thiophen-4-yl) -benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] dibenzothiophene (abbreviation: DBTFLP-III) ), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), 4- [3- (triphenylene-2-yl) phenyl] Examples thereof include dibenzothiophene (abbreviation: mDBTPTp-II).

Specific examples of zinc and aluminum-based metal complexes, which are organic compounds having high electron transport properties, include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq) and tris (4-methyl-8-quinolinolato). ) Aluminum (III) (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] _{quinolinato) berylium (II) (abbreviation: BeBq 2} ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) ) Aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq) and the like, metal complexes having a quinoline skeleton or a benzoquinoline skeleton and the like can be mentioned.

In addition, oxazoles such as bis [2- (2-benzothazolyl) phenolato] zinc (II) (abbreviation: ZnPBO) and bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) A system, a metal complex having a thiazole-based ligand, or the like can also be used.

Specific examples of the oxaziazole derivative, the triazole derivative, the benzoimidazole derivative, the quinoxalin derivative, the dibenzoquinoxalin derivative, and the phenanthroline derivative, which are organic compounds having high electron transport properties, are 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-Il] 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) -Benzene triyl) Tris (1-phenyl-1H-benzoimidazole) (abbreviation: TPBI), 2- [3- (dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzoimidazole (abbreviation: mDBTBIm) -II), 4,4'-bis (5-methylbenzoxazole-2-yl) stilben (abbreviation: BzOs), vasophenantroline (abbreviation: Bphenyl), vasocuproin (abbreviation: BCP), 2,9-bis (naphthalene) -2-yl) -4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphenyl), 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxalin (abbreviation: 2mDBTPDBq- II), 2- [3'-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- [3'-(9H-carbazole-9) -Il) biphenyl-3-yl] dibenzo [f, h] quinoxalin (abbreviation: 2mCzBPDBq), 2- [4- (3,6-diphenyl-9H-carbazole-9-yl) phenyl] dibenzo [f, h] Kinoxalin (abbreviation: 2CzPDBq-III), 7- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxalin (abbreviation: 7mDBTPDBq-II), and 6- [3- (dibenzothiophen-4). -Il) phenyl] dibenzo [f, h] quinoxalin (abbreviation: 6mDBTPDBq-II) and the like can be mentioned.

Specific examples of the heterocyclic compound having a diazine skeleton, the heterocyclic compound having a triazine skeleton, and the heterocyclic compound having a pyridine skeleton, which are organic compounds having high electron transport properties, are 4,6-bis [3- ( Phenantren-9-yl) phenyl] pyrimidine (abbreviation: 4,6 mPnP2Pm), 4,6-bis [3- (4-dibenzothienyl) phenyl] pyrimidine (abbreviation: 4,6 mDBTP2Pm-II), 4,6-bis [ 3- (9H-carbazole-9-yl) phenyl] pyrimidine (abbreviation: 4.6 mCzP2Pm), 2- {4- [3- (N-phenyl-9H-carbazole-3-yl) -9H-carbazole-9- Il] phenyl} -4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 9- [3- (4,6-diphenyl-1,3,5-triazine-2-yl) phenyl] -9'-Phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02), 3,5-bis [3- (9H-carbazole-9-yl) phenyl] pyridine (abbreviation: 35DCzPPy), Examples thereof include 1,3,5-tri [3- (3-pyridyl) phenyl] benzene (abbreviation: TmPyPB). In particular, the organic compound which is one aspect of the present invention shown in the first embodiment can also be used.

Examples of organic compounds having high electron transport properties include poly (2,5-pyridinediyl) (abbreviation: PPy) and poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3). , 5-Diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2'-bipyridine-6,6'-diyl)] ( A polymer compound such as abbreviation: PF-BPy) can also be used.

When a plurality of organic compounds are used in the light emitting layer (113, 113a, 113b, 113c), two kinds of compounds (first compound and second compound) forming an excitation complex and an organic metal complex are mixed. May be used. In this case, various organic compounds can be appropriately combined and used, but in order to efficiently form an excitation complex, a compound that easily receives holes (hole transporting material) and a compound that easily receives electrons (electrons) can be used. It is particularly preferable to combine it with a transportable material). As specific examples of the hole transporting material and the electron transporting material, the materials shown in the present embodiment can be used. With this configuration, high efficiency, low voltage, and long life can be realized at the same time.

A TADF material is a material that can up-convert a triplet excited state into a singlet excited state (intersystem crossing) with a small amount of thermal energy, and efficiently exhibits light emission (fluorescence) from the singlet excited state. That is. Further, as a condition for efficiently obtaining thermally activated delayed fluorescence, the energy difference between the triplet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. Can be mentioned. In addition, delayed fluorescence in TADF materials refers to emission that has a spectrum similar to that of normal fluorescence but has a significantly long lifetime. Its life is ^10-6 seconds or longer, preferably ^10-3 seconds or longer.

Examples of the TADF material include fullerenes and derivatives thereof, acridine derivatives such as proflavine, and eosin. Examples thereof include metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd) and the like. 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)), and hematoporphyrin-tin fluoride. Complex (abbreviation: SnF ₂ (Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF ₂ (Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF ₂ (OEP)) )), Etioporphyrin-tin fluoride complex (abbreviation: SnF ₂ (Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl ₂ OEP) and the like.

In addition, 2- (biphenyl-4-yl) -4,6-bis (12-phenylindro [2,3-a] carbazole-11-yl) -1,3,5-triazine (abbreviation: PIC) -TRZ), 2- {4- [3- (N-phenyl-9H-carbazole-3-yl) -9H-carbazole-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-dihydroacridin) phenyl] sulfone (abbreviation: DMAC-DPS), Π-electron-rich heteroaromatic rings and π-electron-deficient heteroaromatic rings such as 10-phenyl-10H, 10'H-spiro [acrindin-9,9'-anthracene] -10'-on (abbreviation: ACRSA), etc. A heterocyclic compound having can be used. A substance in which a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded has a stronger donor property of the π-electron-rich heteroaromatic ring and a stronger acceptability of the π-electron-deficient heteroaromatic ring. , It is particularly preferable because the energy difference between the singlet excited state and the triplet excited state becomes small.

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

Further, the above-mentioned material can be used for forming a light emitting layer (113, 113a, 113b) by combining with a low molecular weight material or a high molecular weight material. Further, 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, an electron transport layer (114, 114a) is formed on the light emitting layer (113, 113a) of the EL layer (103, 103a). In the case of the light emitting device having the tandem structure shown in FIG. 1 (D), after the EL layer 103a and the charge generation layer 104 are formed, the electron transport layer 114b is also formed on the light emitting layer 113b of the EL layer 103b. To.

<Electron transport layer>
The electron transport layer (114, 114a, 114b) is a layer that transports the electrons injected from the second electrode 102 to the light emitting layer (113, 113a, 113b) by the electron injection layer (115, 115a, 115b). .. The electron transport layer (114, 114a, 114b) is a layer containing an electron transport material. The electron-transporting material used for the electron-transporting layers (114, 114a, 114b) has an electron mobility of 1 × ^10-6 cm ² / Vs or more when the square root of the electric field strength [V / cm] is 600. The substance to have is preferable. Any substance other than these can be used as long as it is a substance having a higher electron transport property than holes. Further, since the organic compound which is one aspect of the present invention shown in the first embodiment has excellent electron transportability, it can also be used as an electron transport layer.

Examples of the electron-transporting material include 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, and the like, as well as oxazole derivatives, triazole derivatives, and imidazole derivatives. Π electron deficiency including oxazole derivative, thiazole derivative, phenanthroline derivative, quinoline derivative having quinoline ligand, benzoquinoline derivative, quinoxalin derivative, dibenzoquinoxalin derivative, pyridine derivative, bipyridine derivative, pyrimidine derivative, and other nitrogen-containing heteroaromatic compounds A material having high electron transport property such as a type 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 ), and bis (10-hydroxy). Benzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) ) (Abbreviation: Znq) or other metal complex having a quinoline skeleton or a benzoquinoline skeleton, bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-) Benzothiazolyl) phenolat] Examples thereof include a metal complex having an oxazole skeleton or a thiazole skeleton such as zinc (II) (abbreviation: ZnBTZ).

In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- ( p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 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 (abbreviation:: Triazole derivatives such as p-EtTAZ), 2,2', 2''-(1,3,5-benzenetriyl) tris (1-phenyl-1H-benzoimidazole) (abbreviation: TPBI), 2- [3 -(Dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzoimidazole (abbreviation: mDBTBIm-II) and other imidazole derivatives (including benzoimidazole derivatives) and 4,4'-bis (5-methyl) Oxazole derivatives such as benzoxazole-2-yl) stilben (abbreviation: BzOs), vasophenantroline (abbreviation: Bphenyl), vasocuproin (abbreviation: BCP), 2,9-bis (naphthalen-2-yl) -4,7- Phenantroline derivatives such as diphenyl-1,10-phenylene (abbreviation: NBphenyl), 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[ 3'-(dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxalin (abbreviation: 2mDBTBPDBq-II), 2- [3'-(9H-carbazole-9-yl) biphenyl-3 -Il] dibenzo [f, h] quinoxalin (abbreviation: 2mCzBPDBq), 2- [4- (3,6-diphenyl-9H-carbazole-9-yl) phenyl] dibenzo [f, h] quinoxalin (abbreviation: 2CzPDBq-) III), 7- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxalin (abbreviation: 7mDBTPDBq-II), and 6- [3- (dibenzothiophen-4-yl) phenyl] Benzene Kinoxalin derivatives such as nzo [f, h] quinoxalin (abbreviation: 6mDBTPDBq-II), or dibenzoquinoxalin 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), 4,6-bis [3- (9H-carbazole-9-yl) phenyl ] Pyrimidine derivatives such as pyrimidine (abbreviation: 4.6 mCzP2Pm), 2- {4- [3- (N-phenyl-9H-carbazole-3-yl) -9H-carbazole-9-yl] phenyl} -4,6 A triazine derivative such as −diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) can be used. In particular, the organic compound which is one aspect of the present invention shown in the first embodiment can also be used.

In addition, poly (2,5-pyridinediyl) (abbreviation: PPy), poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF). -Py), poly [(9,9-dioctylfluorene-2,7-diyl) -co- (2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) Molecular compounds can also be used.

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

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 vapor deposition method. After that, the EL layer 103a and the charge generation layer 104 are formed, the electron transport layer 114b of the EL layer 103b is formed, and then the electron injection layer 115b is formed on the EL layer 103b by a vacuum vapor deposition method.

<Electron injection layer>
The electron injection layer (115, 115a, 115b) is a layer containing a substance having a high electron injection property. The electron injection layer (115, 115a, 115b) contains an alkali metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiO _x ), or an alkali. Earth metals, or compounds thereof, can be used. In addition, rare earth metal compounds such as erbium fluoride (ErF _{3) can be used.} Further, an electlide may be used for the electron injection layer (115, 115a, 115b). Examples of the electride include a substance in which a high concentration of electrons is added to a mixed oxide of calcium and aluminum. In addition, the substance constituting the above-mentioned electron transport layer (114, 114a, 114b) can also be used.

Further, a composite material formed by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer (115, 115a, 115b). Such a composite material is excellent in electron injection property and electron transport property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting generated electrons, and specifically, for example, an electron transporting material (metal complex) used for the above-mentioned electron transport layer (114, 114a, 114b). , Complex aromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium and the like can be mentioned. Further, alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxides, calcium oxides, barium oxides and the like can be mentioned. A Lewis base such as magnesium oxide can also be used. Further, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

In the light emitting device shown in FIG. 1D, when the light obtained from the light emitting layer 113b is amplified, the optical distance between the second electrode 102 and the light emitting layer 113b is the light emitted by the light emitting layer 113b. It is preferably formed so as to be less than 1/4 of the wavelength 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. 1 (D), the charge generation layer 104 receives electrons in the EL layer 103a when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. Has a function of injecting holes into the EL layer 103b. The charge generation layer 104 may have a structure in which an electron acceptor (acceptor) is added to the hole transporting material, or an electron donor (donor) added to the electron transporting material. Good. Moreover, both of these configurations may be laminated. By forming the charge generation layer 104 using the above-mentioned material, it is possible to suppress an increase in the drive voltage when the EL layers are laminated.

When the charge generation layer 104 has a structure in which an electron acceptor is added to the hole transporting material, the material shown in the present embodiment can be used as the hole transporting material. Further, as the electron acceptor, _{7,7,8,8-(abbreviation:} F 4 -TCNQ), chloranil, and the like can be given. In addition, oxides of metals belonging to Group 4 to Group 8 in the Periodic Table of the Elements can be mentioned. Specific examples thereof include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and renium oxide.

When the charge generating layer 104 has a configuration in which an electron donor is added to the electron transporting material, the material shown in the present embodiment can be used as the electron transporting material. Further, as the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, a metal belonging to the second or thirteenth group in the periodic table of elements, an oxide thereof, or a carbonate 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 tetrathianaphthalene may be used as an electron donor.

The EL layer 103c of FIG. 1 (E) may have the same configuration as the EL layer (103, 103a, 103b) described above. Further, the charge generation layers 104a and 104b may have the same configuration as the charge generation layer 104 described above.

<Board>
The light emitting device shown in this embodiment can be formed on various substrates. The type of substrate is not limited to a specific one. Examples of substrates include semiconductor substrates (for example, single crystal substrates or silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates, metal substrates, stainless steel substrates, substrates with stainless still foils, tungsten substrates, etc. Examples include a substrate having a tungsten foil, a flexible substrate, a laminated film, a paper containing a fibrous material, or a base film.

Examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, and soda lime glass. Further, as an example of a flexible substrate, a laminated film, a base film, etc., plastics typified by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), acrylic resins, etc. Examples thereof include synthetic resins, polypropylene, polyesters, polyvinyl fluorides, or polyvinyl chlorides, polyamides, polyimides, aramid resins, epoxy resins, inorganic vapor-deposited films, and papers.

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 fabricate the light emitting device shown in the present embodiment. When the vapor deposition method is used, 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 deposition method, or a vacuum vapor deposition method, or a chemical vapor deposition method (CVD method) is used. be able to. In particular, functional layers (hole injection layers (111, 111a, 111b), hole transport layers (112, 112a, 112b), light emitting layers (113, 113a, 113b, 113c), electron transport) included in the EL layer of the light emitting device. For the layers (114, 114a, 114b), electron injection layers (115, 115a, 115b), and charge generation layers (104, 104a, 104b)), a vapor deposition method (vacuum vapor deposition method, etc.) and a coating method (dip coating method) , Die coat method, bar coat method, spin coat method, spray coat method, etc.), printing method (ink ink method, screen (hole plate printing) method, offset (flat plate printing) method, flexo (letter plate printing) method, gravure method, microcontact It can be formed by a method such as a method, a nanoimprint method, etc.).

Each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a, 112b)) constituting the EL layer (103, 103a, 103b) of the light emitting device shown in the present embodiment. , The light emitting layer (113, 113a, 113b, 113c), the electron transporting layer (114, 114a, 114b), the electron injecting layer (115, 115a, 115b) and the charge generating layer (104, 104a, 104b)) are described above. The material is not limited, and other materials can be used in combination as long as they can satisfy the functions of each layer. As an example, high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (compounds in the intermediate region between low molecular weight and high molecular weight: molecular weight 400 to 4000), inorganic compounds (quantum dot materials, etc.) may be used. it can. As the quantum dot material, a colloidal quantum dot material, an alloy type quantum dot material, a core / shell type quantum dot material, a core type quantum dot material, or the like can be used.

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

(Embodiment 3)
In the present embodiment, a light emitting device which is one aspect of the present invention will be described. 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 a light emitting device (203R, 203G, 203B, 203W) are electrically connected. It is an apparatus, and a plurality of light emitting devices (203R, 203G, 203B, 203W) have a common EL layer 204, and the optical distance between the electrodes of each light emitting device is increased according to the light emitting color of each light emitting device. It has a tuned microcavity structure. Further, it is a top emission type light emitting device in which light emitted from the EL layer 204 is emitted through a color filter (206R, 206G, 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 reflecting electrode. Further, the second electrode 208 is formed so as to function as a semi-transmissive / semi-reflective electrode. As the electrode material for forming the first electrode 207 and the second electrode 208, it may be used as appropriate with reference to the description of other embodiments.

Further, in FIG. 2A, for example, when 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 is a white light emitting device, FIG. ), The light emitting device 203R is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200R, and the light emitting device 203G is the first electrode 207 and the second electrode. The distance between the light emitting device 203B and the first electrode 207 is adjusted to be 200 G, and the distance between the light emitting device 203B and the second electrode 208 is adjusted to be 200 B. As shown in FIG. 2B, the conductive layer 210R is laminated on the first electrode 207 in the light emitting device 203R, and the conductive layer 210G is laminated on the first electrode 207 in the light emitting device 203G for optical adjustment. It can be performed.

Color filters (206R, 206G, 206B) are formed on the second substrate 205. The color filter is a filter that allows visible light to pass through a specific wavelength range and blocks the specific wavelength range. Therefore, as shown in FIG. 2A, red light can be obtained from the light emitting device 203R by providing the color filter 206R that allows only the red wavelength region to pass at a position overlapping the light emitting device 203R. Further, by providing a color filter 206G that allows only the green wavelength region to pass at a position overlapping 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 allows only the blue wavelength region to pass at a position overlapping 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 without providing a color filter. 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 using a transparent material.

FIG. 2A shows a light emitting device having a structure (top emission type) that extracts light emission on the side of the second substrate 205, but as shown in FIG. 2C, the first substrate on which the FET 202 is formed is formed. It may be a light emitting device having a structure (bottom emission type) that extracts light to the 201 side. In the case of a bottom emission type light emitting device, the first electrode 207 is formed so as to function as a semitransmissive / semi-reflective electrode, and the second electrode 208 is formed so as to function as a reflective electrode. Further, as the first substrate 201, at least a translucent substrate is used. Further, the color filters (206R', 206G', 206B') may be provided on the first substrate 201 side of the light emitting devices (203R, 203G, 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 according to one aspect of the present invention is limited to the configuration thereof. It may be configured to have a yellow light emitting device or an orange light emitting device. 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.) for manufacturing these light emitting devices, other embodiments It may be used as appropriate with reference to the description in. In that case, it is also necessary to appropriately select a color filter according to the emission color of the light emitting device.

With the above configuration, it is possible to obtain a light emitting device including a light emitting device exhibiting a plurality of light emitting colors.

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

(Embodiment 4)
In the present embodiment, a light emitting device which is one aspect of the present invention will be described.

By applying the element configuration of the light emitting device according to one aspect of the present invention, an active matrix type light emitting device and a passive matrix type light emitting device can be manufactured. 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 aspect of the present invention. It is possible to apply the light emitting device described in another embodiment to the light emitting device shown in this embodiment.

In the present embodiment, the active matrix type light emitting device will be described with reference to FIG.

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

Further, a routing wiring 307 is provided on the first substrate 301. The routing wiring 307 is electrically connected to the FPC 308 which is an external input terminal. The FPC 308 transmits an external signal (for example, a video signal, a clock signal, a start signal, a reset signal, etc.) and an electric potential to the drive circuit unit (303, 304a, 304b). Further, a printed wiring board (PWB) may be attached to the FPC 308. The state in which these FPCs and PWBs are attached is included in the light emitting device.

Next, FIG. 3B shows a cross-sectional structure.

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

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

The crystallinity of the semiconductors that can be used for these FETs 309, 310, 311 and 312 is not particularly limited, and amorphous semiconductors and crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single crystal semiconductors, etc.) Alternatively, any of (semiconductors having a crystal region in part) may be used. It is preferable to use a semiconductor having crystallinity because deterioration of transistor characteristics can be suppressed.

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 drive circuit unit 303 has an FET 309 and an FET 310. The drive circuit unit 303 may be formed of a circuit including a unipolar (only one of N-type or P-type) transistors, or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. May be done. Further, the configuration may have an external drive circuit.

The end of the first electrode 313 is covered with an insulator 314. As the insulator 314, an organic compound such as a negative type photosensitive resin or a positive type photosensitive resin (acrylic resin), or an inorganic compound such as silicon oxide, silicon oxide nitride, or silicon nitride can be used. .. It is preferable that the upper end portion or the lower end portion of the insulator 314 has a surface having a curvature. Thereby, the covering property of the film formed on the upper layer of the insulator 314 can be improved.

The EL layer 315 and the second electrode 316 are laminated and formed on the first electrode 313. 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.

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

Further, although only one light emitting device 317 is shown in the cross-sectional view shown in FIG. 3 (B), it is assumed that a plurality of light emitting devices are arranged in a matrix in the pixel unit 302. A light emitting device capable of obtaining three types of light emission (R, G, B) can be selectively formed on the pixel unit 302 to form a light emitting device capable of full-color display. In addition to the light emitting devices that can obtain three types of light emission (R, G, B), for example, light emission that can obtain light emission of white (W), yellow (Y), magenta (M), cyan (C), etc. Devices may be formed. For example, by adding a light emitting device that can obtain the above-mentioned several types of light emission to a light emitting device that can obtain three types (R, G, B) of light emission, effects such as improvement of color purity and reduction of power consumption can be obtained. Can be done. Further, it may be a light emitting device capable of full-color display by combining with a color filter. As the type of color filter, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y) and the like can be used.

The FETs (309, 310, 311 and 312) and the light emitting device 317 on the first substrate 301 are the first substrate by bonding the second substrate 306 and the first substrate 301 with the sealing material 305. It has a structure provided in a region 318 surrounded by 301, a second substrate 306, and a sealant 305. The region 318 may be filled with an inert gas (nitrogen, argon, etc.) or an organic substance (including the sealing material 305).

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

As described above, an active matrix type light emitting device can be obtained.

Further, 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 the FET and the light emitting device may be formed on another substrate having a peeling layer. After forming the FET, the FET and the light emitting device may be peeled off by a peeling layer by applying heat, force, laser irradiation, or the like, and further reprinted on a flexible substrate. As the release layer, for example, a laminate of an inorganic film of a tungsten film and a silicon oxide film, an organic resin film such as polyimide, or the like can be used. The flexible substrate includes a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a cloth substrate (natural fiber (silk, cotton, linen), synthetic fiber (natural fiber (silk, cotton, linen)), in addition to a substrate capable of forming a transistor. Nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester), leather substrates, rubber substrates and the like. By using these substrates, it is possible to achieve excellent durability and heat resistance, and to reduce the weight and thickness.

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

(Embodiment 5)
In the present embodiment, an example of various electronic devices and automobiles completed by applying a light emitting device according to an aspect of the present invention and a light emitting device having a light emitting device according to the present invention will be described. The light emitting device can be mainly applied to the display unit in the electronic device described in the present embodiment.

The electronic devices shown in FIGS. 4 (A) to 4 (E) include a housing 7000, a display unit 7001, a speaker 7003, an LED lamp 7004, an operation key 7005 (including a power switch or an operation switch), a connection terminal 7006, and the like. Sensor 7007 (force, displacement, position, speed, acceleration, angular speed, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, voice, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity , Including the ability to measure tilt, vibration, odor, or infrared rays), microphone 7008, and the like.

FIG. 4A is a mobile computer, which may have a switch 7009, an infrared port 7010, and the like, in addition to those described above.

FIG. 4B is a portable image playback device (for example, a DVD playback device) provided with a recording medium, which may have a second display unit 7002, a recording medium reading unit 7011, and the like in addition to those described above. it can.

FIG. 4C is a digital camera with a television image receiving function, which may have an antenna 7014, a shutter button 7015, an image receiving unit 7016, and the like in addition to those described above.

FIG. 4 (D) is a mobile information terminal. The mobile information terminal has a function of displaying information on three or more surfaces of the display unit 7001. Here, an example is shown in which information 7052, information 7053, and information 7054 are displayed on different surfaces. For example, the user can check the information 7053 displayed at a position that can be observed from above the mobile information terminal with the mobile information terminal stored in the chest pocket of the clothes. The user can check the display without taking out the mobile information terminal from the pocket, and can determine, for example, whether or not to receive a call.

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

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

The electronic devices shown in FIGS. 4 (A) to 4 (F) can have various functions. For example, a function to display various information (still images, moving images, 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). , Wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read program or data recorded on recording medium It can have a function of displaying on a display unit, and the like. Further, in an electronic device having a plurality of display units, a function of mainly displaying image information on one display unit and mainly displaying character information on another display unit, or parallax is considered on a plurality of display units. It is possible to have a function of displaying a three-dimensional image by displaying the image. Further, in an electronic device having an image receiving unit, a function of shooting a still image, a function of shooting a moving image, a function of automatically or manually correcting a shot image, and a function of recording the shot image as a recording medium (external or built in a camera). It can have a function of saving, a function of displaying a captured image on a display unit, and the like. The functions that the electronic devices shown in FIGS. 4A to 4F can have are not limited to these, and can have various functions.

FIG. 4 (G) is a wristwatch-type personal digital assistant, which can be used as, for example, a smart watch. This wristwatch-type portable information terminal has a housing 7000, a display unit 7001, operation buttons 7022 and 7023, a connection terminal 7024, a band 7025, a microphone 7026, a sensor 7029, a speaker 7030, and the like. The display surface of the display unit 7001 is curved, and display can be performed along the curved display surface. In addition, this personal digital assistant can make a hands-free call by, for example, mutual communication with a headset capable of wireless communication. The connection terminal 7024 can also be used for data transmission and charging with other information terminals. The charging operation can also be performed by wireless power supply.

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

The smart watch shown in FIG. 4 (G) can have various functions. For example, a function to display various information (still images, moving images, 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). , Wireless communication function, function to connect to various computer networks using wireless communication function, function to transmit or receive various data using wireless communication function, read program or data recorded on recording medium It can have a function of displaying on a display unit, and the like.

In addition, inside the housing 7000, speakers, sensors (force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, voice, time, hardness, electric field, current , Includes the ability to measure voltage, power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), microphones and the like.

A light emitting device according to an aspect of the present invention and a display device having a light emitting device according to the present invention can be used for each display unit of the electronic device shown in the present embodiment and has a long life. Can be realized.

Further, examples of the electronic device to which the light emitting device is applied include a foldable portable information terminal as shown in FIGS. 5A to 5C. FIG. 5 (A) shows the mobile information terminal 9310 in the deployed state. Further, FIG. 5B shows a mobile information terminal 9310 in a state of being changed from one of the unfolded state or the folded state to the other. Further, FIG. 5C shows a mobile information terminal 9310 in a folded state. The mobile information terminal 9310 is excellent in portability in the folded state, and is excellent in display listability due to a wide seamless display area in the unfolded state.

The display unit 9311 is supported by three housings 9315 connected by a hinge 9313. The display unit 9311 may be a touch panel (input / output device) equipped with a touch sensor (input device). Further, the display unit 9311 can reversibly deform the mobile information terminal 9310 from the unfolded state to the folded state by bending between the two housings 9315 via the hinge 9313. The light emitting device of one aspect of the present invention can be used for the display unit 9311. In addition, a long-life electronic device can be realized. The display area 9312 in the display unit 9311 is a display area located on the side surface of the folded mobile information terminal 9310. Information icons, frequently used application and program shortcuts, and the like can be displayed in the display area 9312, and information can be confirmed and applications can be started smoothly.

Further, the automobile to which the 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 the light 5101 (including the rear part of the vehicle body) on the outside of the automobile shown in FIG. 6A, the wheel 5102 of the tire, a part or the whole of the door 5103, and the like. Further, it can be applied to the display unit 5104, the steering wheel 5105, the shift lever 5106, the seat seat 5107, the inner rear view mirror 5108, and the like shown in FIG. 6B. In addition, it may be applied to a part of a glass window.

As described above, an electronic device or an automobile to which a light emitting device or a display device according to an aspect of the present invention is applied can be obtained. In that case, a long-life electronic device can be realized. The applicable electronic devices and automobiles are not limited to those shown in the present embodiment, and can be applied in all fields.

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

(Embodiment 6)
In the present embodiment, a configuration of a light emitting device according to an aspect of the present invention or a lighting device manufactured by applying a light emitting device which is a part thereof will be described with reference to FIG. 7.

7 (A) and 7 (B) show an example of a cross-sectional view of a lighting device. Note that FIG. 7A is a bottom emission type lighting device that extracts light to the substrate side, and FIG. 7B is a top emission type lighting device that extracts light to the sealing substrate side.

The lighting device 4000 shown in FIG. 7A has a light emitting device 4002 on a substrate 4001. Further, it has a substrate 4003 having irregularities on the outside of 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 electrically connected to the first electrode 4004 may be provided. An insulating layer 4010 is formed on the auxiliary wiring 4009.

Further, the substrate 4001 and the sealing substrate 4011 are adhered with a sealing material 4012. Further, it is preferable that a desiccant 4013 is provided between the sealing substrate 4011 and the light emitting device 4002. Since the substrate 4003 has irregularities as shown in FIG. 7A, it is possible to improve the efficiency of extracting light generated by the light emitting device 4002.

The illumination device 4200 of 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 electrically connected to the second electrode 4206 may be provided. Further, the insulating layer 4210 may be provided below the auxiliary wiring 4209.

The substrate 4201 and the uneven sealing substrate 4211 are adhered to each other with a sealing material 4212. Further, a barrier film 4213 and a flattening film 4214 may be provided between the sealing substrate 4211 and the light emitting device 4202. Since the sealing substrate 4211 has irregularities as shown in FIG. 7B, it is possible to improve the efficiency of extracting light generated by the light emitting device 4202.

Further, as an application example of these lighting devices, there is a ceiling light for indoor lighting. Ceiling lights include a ceiling-mounted type and a ceiling-embedded type. It should be noted that such a lighting device is configured by combining a light emitting device with a housing or a cover.

In addition, it can be applied to foot lights that can illuminate the floor surface to improve the safety of the feet. It is effective to use the foot light in a bedroom, stairs, aisles, etc., for example. In that case, the size and shape can be appropriately changed according to the size and structure of the room. It is also possible to make a stationary lighting device configured by combining a light emitting device and a support base.

It can also be applied as a sheet-shaped lighting device (sheet-shaped lighting). Since the sheet-shaped lighting is used by being attached to a wall surface, it can be used for a wide range of purposes without taking up space. It is also easy to increase the area. It can also be used for a wall surface or a housing having a curved surface.

In addition to the above, a light emitting device according to an aspect of the present invention or a light emitting device which is a part thereof is applied to a part of furniture provided in a room to obtain a lighting device having a function as furniture. Can be done.

As described above, various lighting devices to which the light emitting device is applied can be obtained. It should be noted that these lighting devices are included in one aspect of the present invention.

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

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

<Step 1; Synthesis of Ethyl2- (6-Chloro-3-oxo-1-benzofuran-2-yl) -2-hydroxyacetate>
First, 24 mL of ethyl glyoxylate (polymer type) (47% toluene solution) was added to a three-necked flask, the inside of the flask was replaced 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 this mixture, and the mixture was 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 the mixture was heated and stirred for 39 hours. After a 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 the target white solid. Water was added to the filtrate obtained here, and the aqueous layer and the organic layer were separated.

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

<Step 2; Synthesis of 7-chloro [1] benzoflo [3,2-c] pyridazine-3-one>
Next, 22 g (81 mmol) of ethyl2- (6-chloro-3-oxo-1-benzofuran-2-yl) -2-hydroxyacetate obtained in step 1 above and 340 mL of ethanol were added to the three-necked flask, and the mixture was added thereto. 12 g (240 mmol) of hydrazine monohydrate was added, the mixture was stirred overnight at room temperature, and then heated under reflux for 40 hours. The resulting reaction mixture was poured into water and stirred at room temperature. The mixture was suction filtered and the solid was washed with ethanol to obtain 5.5 g of the desired pale orange solid in a yield of 30%. The synthesis scheme of step 2 is shown in (a-2).

<Step 3; Synthesis of 3,7-dichloro [1] benzoflo [3,2-c] pyridazine>
Next, 5.5 g (25 mmol) of 7-chloro [1] benzoflo [3,2-c] pyridazine-3-one and 80 mL of toluene obtained in step 2 above were added to a three-necked flask, and 19 g of phosphoryl chloride (19 g) was added thereto. 125 mmol) and 0.1 mL of dimethylformamide were added, and the mixture was heated under reflux for 12 hours.

The obtained reaction mixture was neutralized by adding little by little to 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 saturated brine, added anhydrous magnesium sulfate, and dried. The resulting mixture was naturally filtered and the filtrate was concentrated to give a solid. This solid was dissolved in heated toluene, and suction filtration was performed through a filter medium in which Celite, Alumina, and Celite were laminated in this order. The obtained filtrate was concentrated, and the solid was washed with ethanol to obtain 3.7 g of the desired white solid in a yield of 63%. The synthesis scheme of step 3 is shown in (a-3).

<Step 4; Synthesis of 7-chloro-3- [3- (dibenzothiophen-4-yl) phenyl] [1] benzoflo [3,2-c] pyridazine>
Next, 3.1 g (13 mmol) of 3,7-dichloro [1] benzoflo [3,2-c] pyridazine obtained in step 3 above, 4.4 g of 3- (dibenzothiophen-4-yl) phenylboronic acid. (14 mmol), 9.1 g (43 mmol) of tripotassium phosphate, 0.22 g (0.52 mmol) of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (S-phos), and 130 mL of xylene were placed in a reaction vessel. , The inside of the reaction vessel was degassed and replaced with nitrogen. 63 mg (0.28 mmol) of palladium (II) acetate was added to this mixture, and the mixture was heated and stirred at 120 ° C. for 12 hours. To this, 0.22 g (0.52 mmol) of S-phos and 63 mg (0.28 mmol) of palladium (II) acetate were added, and the mixture was heated and stirred at 130 ° C. for 8.5 hours. Here, further 3- (dibenzothiophen-4-yl) phenylboronic acid 0.95 g (3.1 mmol), tripotassium phosphate 2.0 g (9.4 mmol), S-phos 0.21 g (0.52 mmol), 59 mg (0.27 mmol) of palladium (II) acetate was added, and the mixture was heated and stirred at 130 ° C. for 14 hours. Here, further 3- (dibenzothiophen-4-yl) phenylboronic acid 0.95 g (3.1 mmol), tripotassium phosphate 2.0 g (9.4 mmol), S-phos 0.21 g (0.52 mmol), 54 mg (0.24 mmol) of palladium (II) acetate was added, and the mixture was heated and stirred at 130 ° C. for 7 hours. Here, further 3- (dibenzothiophen-4-yl) phenylboronic acid 0.95 g (3.1 mmol), tripotassium phosphate 1.9 g (9.0 mmol), S-phos 0.23 g (0.56 mmol), 71 mg (0.32 mmol) of palladium (II) acetate was added, and the mixture was heated and stirred 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, and the mixture was heated and stirred 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 from toluene to obtain 1.6 g of the target white solid in a yield of 27%. The synthesis scheme of step 4 is shown in (a-4).

<Step 5; Synthesis of 3- [3- (dibenzothiophen-4-yl) phenyl] -7-phenyl [1] benzoflo [3,2-c] pyridazine (abbreviation: 7Ph-3mDBtPBfpd)>
Next, 0.53 g (1.1 mmol) of 7-chloro-3- [3- (dibenzothiophen-4-yl) phenyl] [1] benzoflo [3,2-c] pyridazine obtained in step 4 above, 0.18 g (1.4 mmol) of phenylboronic acid, 0.62 g (4.1 mmol) of cesium fluoride, and 30 mL of xylene were placed in a reaction vessel, and the inside of the vessel was replaced with nitrogen. After heating the mixture to 60 ° C. with stirring, 27 mg (0.029 mmol) of tris (dibenzylideneacetone) dipalladium (0) and 25 mg (0.069 mmol) of 2'-(dicyclohexylphosphino) acetophenone ethylene ketal were added. In addition, the temperature was raised to 110 ° C. and the mixture was heated and stirred for 23 hours.

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

After a lapse of time, 0.086 g (0.70 mmol) of phenylboronic acid, 0.3 g (2.0 mmol) of cesium fluoride, 12 mg (0.013 mmol) of tris (dibenzylideneacetone) dipalladium (0), were added to this mixture. 13 mg (0.036 mmol) of 2'-(dicyclohexylphosphino) acetophenone ethylene ketal was added, and the mixture was heated and stirred for 13 hours.

Water was added to the obtained mixture, suction filtration was performed, and the solid was washed with ethanol. This solid was dissolved in heated toluene and suction filtered through a filter medium laminated in the order of Celite, Alumina, and Celite. The obtained filtrate was concentrated to obtain a solid. This solid was recrystallized from toluene to obtain 0.23 g of the target white solid in a yield of 40%. The synthesis scheme of step 5 is shown in the following formula (a-5).

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

^{1 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 physical characteristics of 7Ph-3mDBtPBfpd≫
Next, the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of 7Ph-3mDBtPBfpd were measured. An ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used for the measurement of the absorption spectrum. A fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used for the measurement of the emission spectrum. The measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents wavelength and the vertical axis represents absorption intensity.

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

Next, the phosphorescence spectrum of a toluene solution of 7Ph-3mDBtPBfpd was measured. An absolute PL quantum yield measuring device (C11347-01 manufactured by Hamamatsu Photonics Co., Ltd.) was used to measure the phosphorescence spectrum, and the glove box (LABstar M13 (1250/780) manufactured by Bright Co., Ltd.) was used in a nitrogen atmosphere. The toluene deoxidized solution was placed in a quartz cell, sealed, and measured at the temperature of liquid nitrogen. The measurement result of the obtained phosphorescence spectrum is shown in FIG. The horizontal axis represents wavelength and the vertical axis represents emission intensity.

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

It can be said that the organic compound 7Ph-3mDBtPBfpd, which is one aspect of the present invention, is a host material suitable for a phosphorescent material (guest material) that has a high T1 level and emits light in the vicinity of green. The organic compound 7Ph-3mDBtPBfpd, which is one aspect of the present invention, can also be used as a host material or a luminescent substance for a phosphorescent substance in the visible region.

≪Synthesis example 2≫
In this example, the organic compound, 7- (1,1'-biphenyl-3-yl) -3- [3- (, which is one aspect of the present invention represented by the structural formula (101) of Embodiment 1. A method for synthesizing dibenzothiophene-4-yl) phenyl] [1] benzoflo [3,2-c] pyridazine (abbreviation: 7mBP-3mDBtPBfpd) will be described. The structure of 7mBP-3mDBtPBfpd is shown below.

<Step 1; Synthesis of 7mBP-3mDBtPBfpd>
7-Chloro-3- [3- (dibenzothiophen-4-yl) phenyl] [1] benzoflo [3,2-c] pyridazine 1 obtained in step 4 of Example 1 (Synthesis 1) above. .6 g (3.5 mmol), 0.71 g (3.5 mmol) 3-biphenylboronic acid, 2.2 g (11 mmol) tripotassium phosphate, 35 mL diglyme, 0.79 g (11 mmol) tert-butanol were placed in the reaction vessel. , The inside of the container was degassed and replaced with nitrogen.

The mixture was heated to 60 ° C., 16 mg (0.070 mmol) of palladium (II) acetate and 50 mg (0.14 mmol) of di (1-adamantyl) -n-butylphosphine (cataCXiumA) were added, and 6.5 at 90 ° C. It was heated and stirred for hours. To this, 8 mg (0.035 mmol) of palladium (II) acetate and 25 mg (0.070 mmol) of cataCXiumA were further added, and the mixture was heated and stirred at 90 ° C. for 8 hours. Water was added to the resulting reaction mixture, the solid was suction filtered and washed with ethanol. This solid was dissolved in heated toluene and suction filtered through a filter medium in which Celite, Alumina, and Celite were laminated.

The obtained filtrate was concentrated to obtain an oil. The oil was purified by silica gel column chromatography. As the developing solvent, toluene was first used, and then a mixed solvent of toluene: ethyl acetate = 9: 1 was used. Ethanol was added to the oil obtained by concentrating the obtained fraction, and ultrasonic waves were irradiated to precipitate a solid. This solid was suction-filtered to obtain 1.45 g of the target white solid in a yield of 71%. The synthesis scheme of step 1 is shown in the following formula (b-1).

1.4 g of the obtained white solid was sublimated and purified by the train sublimation method. The sublimation purification conditions were such that the solid was heated 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. The conditions for sublimation purification were a pressure of 2.45 Pa and a heating temperature of 310 ° C. After sublimation purification, the target product, 7- (1,1'-biphenyl-3-yl) -3- [3- (dibenzothiophen-4-yl) phenyl] [1] benzoflo [3,2-c] pyridazine. (Abbreviation: 7 mBP-3 mDBtPBfpd) 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. Moreover, ¹ H-NMR chart is shown in FIG. From this result, it was found that, in this example, 7mBP-3mDBtPBfpd, an organic compound which is one aspect of the present invention represented by the above-mentioned structural formula (101), was obtained.

^{1 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 physical characteristics of 7mBP-3mDBtPBfpd≫
Next, the ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and the emission spectrum of the toluene solution of 7mBP-3mDBtPBfpd were measured. An ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used for the measurement of the absorption spectrum. A fluorometer (FP8600 manufactured by JASCO Corporation) was used for the measurement of the emission spectrum. The measurement results of the absorption spectrum and the emission spectrum of the obtained toluene solution are shown in FIG. The horizontal axis represents wavelength and the vertical axis represents absorption intensity.

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

It can be said that the organic compound 7mBP-3mDBtPBfpd, which is one aspect of the present invention, is a host material suitable for a phosphorescent material (guest material) that has a high T1 level and emits light in the vicinity of green. The organic compound 7mBP-3mDBtPBfpd, which is one aspect of the present invention, can also be used as a host material or a luminescent substance for a phosphorescent substance in the 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 layers 115, 115a, 115b Electron injection layers 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 unit 303 Drive circuit unit (source line drive circuit)
304a, 304b drive circuit section (gate line drive circuit)
305 Sealing material 306 Second substrate 307 Route 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 Region 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 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Drying agent 4015 Diffusing 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 Insulation layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Flattening film 4215 Diffuse Board 5101 Light 5102 Wheel 5103 Door 5104 Display 5105 Handle 5106 Shift lever 5107 Seat seat 5108 Inner rear view mirror 7000 Housing 7001 Display 7002 Second display 7003 Speaker 7004 LED lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7022, 7023 Operation button 7024 Connection terminal 7025 Band 7026 Microphone 7029 Sensor 7030 Speaker 7052, 7053, 7054 Information 9310 Mobile information terminal 9311 Display unit 9312 Display area 9313 Hinge 9315 Housing

Claims (15)

An organic compound represented by the general formula (G1).

(In the formula, Q represents oxygen or sulfur. Further, A is a group having a total carbon number of 12 to 100 and contains a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, and a dibenzothiophene ring. It has one or more of an aromatic ring, a heteroaromatic ring containing a dibenzofuran ring, a heteroaromatic ring containing a carbazole ring, a benzoimidazole ring, and a triphenylamine structure. Further, R ^{1 to} R ⁵ are independently hydrogen, respectively. Alkyl groups with 1 to 6 carbon atoms, substituted or unsubstituted monocyclic saturated hydrocarbons with 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons with 7 to 10 carbon atoms, substituted or unsubstituted Represents an aryl group having 6 to 13 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. An organic compound represented by the general formula (G2).

(In the formula, Q represents oxygen or sulfur, α represents a substituted or unsubstituted phenylene group, n represents an integer of 0 to 4, and Ht _uni represents a hole-transporting skeleton. Further, 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, and a substituted or unsubstituted carbon number 7 to 10 carbon atoms. Represents a polycyclic saturated 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). An organic compound represented by the general formula (G3).

(In the formula, Q represents oxygen or sulfur, Ht _uni represents a hole-transporting skeleton, and R ^{1 to} R ⁵ are hydrogens, alkyl groups having 1 to 6 carbon atoms, substitutions or absences. Substituted monocyclic saturated hydrocarbons with 5 to 7 carbon atoms, substituted or unsubstituted polycyclic saturated hydrocarbons with 7 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 13 carbon atoms, or substituted or substituted Represents an unsubstituted heteroaryl group having 3 to 12 carbon atoms.) In claim 2 or 3,
The Ht _uni is an organic compound having any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure. In 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).


(In formula (I), Q represents an oxygen or sulfur. In addition, R ² to R ⁷¹ represents 1 to 4 substituents each and independently hydrogen, alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted Represents any one of the phenyl groups, and Ar ¹ represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.) An organic compound represented by any one of the structural formulas (100) and (101).
A light emitting device using the organic compound according to any one of claims 1 to 6. It has an EL layer between the pair of electrodes and has an EL layer.
The EL layer is a light emitting device having the organic compound according to any one of claims 1 to 6. It has an EL layer between the pair of electrodes and has an EL layer.
The EL layer has a light emitting layer and has a light emitting layer.
The light emitting layer is a light emitting device having the organic compound according to any one of claims 1 to 6. It has an EL layer between the pair of electrodes and has an EL layer.
The EL layer has a light emitting layer and has a light emitting layer.
The light emitting layer is a light emitting device having the organic compound according to any one of claims 1 to 6 and a phosphorescent material. It has an EL layer between the pair of electrodes and has an EL layer.
The EL layer has a light emitting layer and has a light emitting layer.
The light emitting layer is a light emitting device having the organic compound according to any one of claims 1 to 6, a phosphorescent material, and a carbazole derivative. 11.
The carbazole derivative is a luminescent device that is a carbazole derivative. The light emitting device according to any one of claims 7 to 12.
With at least one of the transistors, or boards,
A light emitting device having. The light emitting device according to claim 13,
With at least one of the microphone, camera, operating buttons, external connections, or speakers,
Electronic equipment with. The light emitting device according to any one of claims 7 to 12.
With at least one of the housing, cover, or support
Lighting device with.