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

Abstract

To provide a novel organic compound, a novel organic compound having hole transport properties, a novel hole transport material, a novel light-emitting element, a light-emitting element with a good lifetime, and a light-emitting element with good luminous efficiency.SOLUTION: The present invention provides an organic compound having a substituted or unsubstituted benzonaphthofuran skeleton, a substituted or unsubstituted carbazole skeleton, and a substituted or unsubstituted amine skeleton, or a light-emitting element using the hole transport material.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] One embodiment of the present invention relates to a light-emitting element, a display module, a lighting module, a display device, a light-emitting element, a display module ... The present invention relates to an optical device, an electronic device, and a lighting device. The technical field of one embodiment of the invention disclosed in the present specification and the like is an object, a method, or a manufacturing method. Alternatively, one aspect of the present invention relates to a process, a machine, a manufacturing method, It is about Cha, or composition of matter. More specifically, the technical field of one embodiment of the present invention disclosed in this specification is a semiconductor device, a display display devices, liquid crystal display devices, light-emitting devices, lighting devices, power storage devices, storage devices, imaging devices, and A driving method or a manufacturing method thereof can be given as an example. [Background technology]

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting elements (organic electroluminescence (EL) elements) that utilize the luminescence element is progressing. The basic structure of the device is a pair of electrodes sandwiching an organic compound layer (EL layer) containing a light-emitting material. A voltage is applied to this element to inject carriers, and the recombination energy of the carriers is By utilizing this, light can be emitted from the light-emitting material.

[0003] Since these light-emitting elements are self-luminous, they have higher visibility than LCDs. The display using such a light-emitting element is suitable for use as a pixel in a display. Another major advantage is that it does not require a backlight and can be made thin and lightweight. Another feature is the fast response time.

[0004] In addition, since these light-emitting elements can form a light-emitting layer continuously in two dimensions, light emission can be obtained in a planar form. This is a characteristic that is difficult to achieve with point light sources typified by incandescent bulbs and LEDs, or linear light sources typified by fluorescent lamps. Therefore, as a planar light source that can be applied to lighting and the like, it has high utility value.

[0005] Displays and lighting devices using such light-emitting elements are suitable for use in various electronic devices, but research and development are being advanced to obtain light-emitting elements with better efficiency and longer lifespan.

[0006] The characteristics of light-emitting elements have improved remarkably, but it still has to be said that they are insufficient to meet the high demands for all characteristics, including efficiency and durability.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] Therefore, an object of one aspect of the present invention is to provide a novel organic compound. Or, an object of one aspect of the present invention is to provide a novel organic compound having hole-transporting properties. Or, one aspect of the present invention aims to provide a novel hole-transporting material. Or, it is an object to provide a novel light-emitting element. Or, it is an object to provide a light-emitting element with good lifespan. Or, it is an object to provide a light-emitting element with good luminous efficiency. Or, An object is to provide an element in which the voltage change associated with the accumulation of the driving time is small.

[0009] Or, in another aspect of the present invention, an object is to provide a highly reliable light-emitting device, an electronic device, and a display device, respectively. Or, in another aspect of the present invention, an object is to provide a light-emitting device, an electronic device, and a display device, respectively, that consume little power. Or, in another aspect of the present invention, an object is to provide a highly reliable light-emitting device, an electronic device, and a display device, respectively. Or, in another aspect of the present invention, an object is to provide a light-emitting device, an electronic device, and a display device, respectively, that consume little power. Or, in another aspect of the present invention, an object is to provide a highly reliable light-emitting device, an electronic device, and a display device, respectively. Or, in another aspect of the present invention, an object is to provide a light-emitting device, an electronic device, and a display device, respectively, that consume little power.

[0010] The present invention only needs to solve any one of the above problems.

Means for Solving the Problems

[0011] One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0012]

Chemical formula

[0013] However, in the general formula (G1), one of R 0 to R 9 is a group represented by the following general formula (g1), and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0014]

Chemical formula

[0015] In the general formula (g1), Cz represents a substituted or unsubstituted carbazolyl group. Also, Ar 4is either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, or a substituted or unsubstituted carb azolyl group. Also, Ar 5 , Ar 6 each independently represents either a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, n represents any one of integers from 1 to 3 , and m represents any one of integers from 0 to 3. However, when Ar 4 is a carb azolyl group, m is any one of integers from 1 to 3. Note that Ar 5 or Ar 6 may have multiple cases depending on the numerical values of n or m. In such cases, the multiple Ar 5 or the multiple A r 6 each independently represents either a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, the sum of the number of carbon atoms of Cz and Ar , and the sum of the number of carbon atoms of Ar 5 and Ar 4 and Ar 6 are each 60 or less.

[0016] Alternatively, another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0017]

Chemical formula

[0018] However, in the general formula (G1), one of R 0 to R 9 is a group represented by the following general formula (g1), and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. represents either one of them.

[0019]

Chem.

[0020] In general formula (g1), Cz represents a group represented by the following general formula (g2). Also, Ar 4 represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, or one of the groups represented by the following general formula (g3) . Also, Ar 5 , Ar 6 each independently represents either a substituted or un substituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, n represents any one of the integers from 1 to 3, and m represents any one of the integers from 0 to 3, provided that when Ar 4 is a carbazolyl group, m is any one of the integers from 1 to 3. Note that Ar 5 or Ar 6 may have multiple cases depending on the numerical values of n or m, and the plurality of Ar 5 or the plurality of Ar 6 each independently represents either a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms . Also, the sum of the number of carbon atoms of Cz and Ar 5 , and the sum of the number of carbon atoms of Ar 4 and Ar 6 are each 60 or less.

[0021]

Chem.

[0022] In general formula (g2), one of R 10 to R 18 represents a bond that binds to Ar 5 , The remainder each independently represents hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

Chem.

[0023] represents a bond that binds to Ar

[0024] and the remainder each independently represents hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. 20 to R 28 represents a bond that binds to Ar 6 and the remainder each independently represents hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. represents a bond that binds to Ar and the remainder each independently represents hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms. represents a bond that binds to Ar and the remainder each independently represents hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0025] Alternatively, another aspect of the present invention is an organic compound in the above configuration, wherein R 0 or R 9 is a group represented by the general formula (g1 ).

[0026] Alternatively, another aspect of the present invention is an organic compound in the above configuration, wherein n is any one of integers from 1 to 3. is an organic compound.

[0027] Alternatively, another aspect of the present invention is an organic compound in the above configuration, wherein Ar 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0028] Alternatively, another aspect of the present invention is an organic compound in the above configuration, wherein Ar4 is a phenyl group which may be substituted or unsubstituted organic compound.

[0029] Or, another aspect of the present invention is that, in the above configuration, Ar 5 and Ar 6 is a phenyl group which may be substituted or unsubstituted organic compound.

[0030] Or, another aspect of the present invention is that, in the above configuration, R in the general formula (G1) 0 is a general group represented by the formula (g1) organic compound.

[0031] Or, another aspect of the present invention is that, in the above configuration, R in the general formula (G1) 9 is a general group represented by the formula (g1) organic compound.

[0032] Or, another aspect of the present invention is that, in the above configuration, R in the general formula (G1) 9 is a substituted or unsubstituted phenyl group organic compound.

[0033] Or, another aspect of the present invention is that, in the above configuration, R in the general formula (g2) 10 is a bond hand organic compound.

[0034] Or, another aspect of the present invention is that, in the above configuration, R in the general formula (g2) 16 is a bond hand organic compound.

[0035] Or, another aspect of the present invention is that, in the above configuration, the R 10 is a substituted or unsubstituted flu enyl group organic compound.

[0036] Or, another aspect of the present invention has an anode, a cathode, and an EL layer, and the EL layer is the anode A light-emitting element that is located between an anode and the cathode and in which the EL layer contains the organic compound described above .

[0037] Alternatively, another aspect of the present invention is a light-emitting device having a light-emitting element having the above configuration, a transistor, or a substrate.

[0038] Alternatively, another aspect of the present invention is an electronic device having the above light-emitting device and at least one of a sensor, an operation button, a speaker, and a microphone.

[0039] Alternatively, another aspect of the present invention is a lighting device having the above light-emitting device and a housing.

[0040] Note that the light-emitting device in this specification includes an image display device using a light-emitting element. In addition, a module in which a connector, for example, an anisotropic conductive film or a TCP (Tape Carrier Package), is attached to the light-emitting element, a module in which a printed wiring board is provided at the tip of the TCP, or a module in which an IC (integrated circuit) is directly mounted on the light-emitting element by a COG (Chip On Glass) method may also be included in the light-emitting device. Furthermore, lighting fixtures and the like may have a light-emitting device. [[Effect of the Invention]]

[0041] In one aspect of the present invention, a novel organic compound can be provided. Alternatively, a novel organic compound having hole-transporting properties can be provided. Alternatively, a novel hole-transporting material can be provided. Alternatively, a novel light-emitting element can be provided. Alternatively, a light-emitting element with good durability can be provided. Alternatively, a light-emitting element with good luminous efficiency can be provided ​​​​​​​​​Alternatively, a light-emitting element with a low driving voltage can be provided. Alternatively, an element with a small voltage change associated with the accumulation of driving time can be provided.

[0042] Alternatively, in another aspect of the present invention, a highly reliable light-emitting device, electronic device, and display device can be provided respectively. Alternatively, in another aspect of the present invention, a light-emitting device, electronic device, and display device with low power consumption can be provided respectively.

[0043] Note that the description of these effects does not prevent the existence of other effects. Note that one aspect of the present invention does not necessarily need to have all of these effects. Note that other effects will be naturally apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other effects from the descriptions in the specification, drawings, claims, etc.

Brief Description of the Drawings

[0044]

Figure 1

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Figure 42

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Figure 44

Figure 45

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Figure 47

Figure 48

Figure 49

Figure 50

Embodiments for Carrying Out the Invention

[0045] 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 those skilled in the art can easily understand that the form and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not to be construed as being limited to the description of the embodiments shown below.

[0046] (Embodiment 1) An organic compound according to one aspect of the present invention is an organic compound represented by the following general formula (G1).

[0047]

Chemical formula

[0048] However, in the organic compound represented by the general formula (G1), R 0 to R 9 one of which is a group represented by the following general formula (g1), and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

[0049] Among the organic compounds represented by the above general formula (G1), when R 0 or R 9 is a group represented by the following general formula ( g1), the organic compound has a relatively deep HOMO level, so it is preferable because the hole injection property into the host material contained in the light-emitting layer with a deep HOMO level is improved. In particular, when R is a group represented by the following general formula (g1), a hole transport material having a high T1 level can be provided. 0 In this case, when R 9 is hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, or a haloalkyl group having 1 to 6 carbon atoms, it is preferable because the T1 level is high. Also, when it is a substituted or unsubstituted phenyl group, it is preferable because an element having high reliability can be provided. A hole transport material having a high T1 level can be suitably used for the host material in the phosphorescent light-emitting layer and the material constituting the hole transport layer adjacent to the phosphorescent light-emitting layer.

[0050]

Chemical formula

[0051] In the general formula (g1), Cz represents a substituted or unsubstituted carbazolyl group. By having the carbazolyl group at this position, the light-emitting element using the organic compound of one embodiment of the present invention can be made into a light-emitting element with good luminous efficiency. Note that Cz may be a group represented by the following general formula (g2).

[0052]

Chemical formula

[0053] In the general formula (g2), one of R 10 to R 18 represents a bond that binds to Ar in the group represented by the above general formula (g1). Note that the bond is preferably R 5 or R 10 or R 16 because it can provide an organic compound having high hole transportability. When the bond is R it is preferably R 16 because it can provide an organic compound having high hole transportability and R 10 is a substituted or unsubstituted phenyl group. Among R to R 10 to R 1 8 those other than the one that is a bond each independently represent hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, respectively.

[0054] Also, in the general formula (g1), Ar 4 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms ​​​​​​Represents any one of a hydrocarbon group and a substituted or unsubstituted carbazolyl group. The carbazolyl group may be a group represented by the following general formula (g3). Here, Ar 4 is substituted or unsubstituted and is an aromatic hydrocarbon group having 6 to 60 carbon atoms, which is preferable because it can provide an organic compound having high hole transportability and a relatively deep HOMO level. By using an organic compound having high hole transportability and a relatively deep HOMO level in the hole transport layer adjacent to the light-emitting layer it is possible to improve the hole injection property into the light-emitting layer and provide a device with high luminous efficiency. Also Ar is more preferably a substituted or unsubstituted phenyl group, particularly an unsubstituted phenyl group, in order to provide an organic compound having high hole transportability. Ar 4 is more preferably a substituted or unsubstituted phenyl group, particularly an unsubstituted phenyl group, in order to provide an organic compound having high hole transportability. In general formula (g3), one of R

[0055]

Chemical formula

[0056] to R 20 to R 28 represents a bond that binds to Ar in the group represented by the above general formula (g1). Here, the bond is preferably R 6 or R 20 or R 26 in order to provide an organic compound having high hole transportability. When the bond is R R 26 it is preferably a substituted or unsubstituted phenyl group in order to provide an organic compound having high hole transportability. R 20 to R to R 20 to R 2 8 among them, those other than the bond are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms A cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen , a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, respectively.

[0057] In the group represented by the general formula (g1), Ar 5 , Ar 6 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Note that Ar 5 , Ar 6 is preferably a substituted or unsubstituted phenylene group because it can provide an organic compound having high hole transportability and a relatively deep HOMO level. Using an organic compound having high hole transportability and a relatively deep HOMO level in the hole transport layer adjacent to the light-emitting layer can improve the hole injection property into the light-emitting layer and provide a device with high luminous efficiency. Further, Ar , Ar 5 , Ar 6 is more preferably an unsubstituted phenylene group because it can provide an organic compound having high hole transportability.

[0058] Here, n in the group represented by the general formula (g1) represents any one of integers from 1 to 3 , and m represents any one of integers from 0 to 3. However, when Ar 4 is a carbazolyl group , m is any one of integers from 1 to 3. Note that Ar 5 or Ar 6 may have multiple cases depending on the numerical values of n or m, but the multiple Ar or the multiple Ar 5 each independently represents any one of substituted or unsubstituted divalent aromatic hydrocarbon groups having 6 to 54 carbon atoms 6 .

[0059] Also, in order to provide an organic compound having high hole transportability, the sum of the number of carbon atoms of Cz and Ar 5 is added, and the sum of the number of carbon atoms of Ar and Ar 4 and Ar 6 shall each be 60 or less.

[0060] The substituents applicable to the general formulas R 0 to R 9 , R 10 to R 18 and R 20 to R 28 specifically include substituents represented by the following structural formulas (1-1) to (1-40) or substituents represented by the following structural formulas (2-1) to (2-13) and the like. Note that the substitution positions of the following structural formulas (2-1) to (2-13) are not limited, and these may further have substituents.

[0061]

Chemical formula

[0062]

Chemical formula

[0063] Ar 4 represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a substituted or unsubstituted carbazolyl group. Specific examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms include substituents represented by the following structural formulas (2-1) to (2-13) and the like. Note that the substitution positions of the following structural formulas (2-1) to (2-13) are not limited. Also, these may further have substituents.

[0064] ​​​​ [Chemical formula]

[0065] In addition, Cz represents a substituted or unsubstituted carbazolyl group, and Ar 4 may be a substituted or unsubstituted carbazolyl group. However, as for the Cz and Ar 4 , specifically, substituents represented by the following structural formulas (3-1) to (3-24) and the like can be cited. Note that these may further have substituents. .

[0066] [Chemical formula]

[0067] In addition, Ar 5 , Ar 6 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. As the substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms, specifically, for example, groups represented by the following structural formulas (2-1) to (2-13) can be used. Note that the substitution positions of the following structural formulas (2-1) to (2-13) are not questioned. Also, these may further have substituents. .

[0068] [Chemical formula]

[0069] R 0 to R 9 , R 10 to R 18 and R 20 to R 28 are aromatic hydrocarbon groups, and when they have two substituents, and also Ar 4 , Cz, Ar5 and Ar 6 further has a substituent In the case, examples of the substituent include an aromatic hydrocarbon group having 6 to 10 carbon atoms, a carbon hydrogen group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group , a halogen, and any one or more of haloalkyl groups having 1 to 6 carbon atoms are, as specific examples of the hydrocarbon group having 1 to 6 carbon atoms, the cyclic hydrocarbon group having 3 to 6 carbon atoms, the alkoxy group having 1 to 6 carbon atoms, the cyano group, the halogen, and the haloalkyl group having 1 to 6 carbon atoms , those represented by the following structural formulas (1-1) to (1-40) can be mentioned . Further, examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenyl group, a naphthyl group, etc. can be mentioned .

[0070]

Chemical formula

[0071] Specific examples of the organic compound having the above configuration are shown below

[0072]

Chemical formula

[0073]

Chemical formula

[0074]

Chemical formula

[0075]

Chemical formula

[0076] [Chemistry]

[0077] [Chemistry]

[0078] [Chemistry]

[0079] [Chemistry]

[0080] [Chemistry]

[0081] [Chemistry]

[0082] [Chemistry]

[0083] [Chemistry]

[0084] [Chemistry]

[0085] [Chemistry]

[0086] [Chemistry]

[0087]

Chem.

[0088]

Chem.

[0089]

Chem.

[0090]

Chem.

[0091]

Chem.

[0092]

Chem.

[0093]

Chem.

[0094]

Chem.

[0095]

Chem.

[0096]

Chem.

[0097] [Chemical]

[0098] [Chemical]

[0099] [Chemical]

[0100] The organic compounds as described above can be synthesized by the following synthetic scheme or the like.

[0101] Here, in the above general formula (G1), when the group represented by the general formula (g1) is bonded to R 9 and when the group represented by (g1) is bonded to R 0 , taking these cases as examples, the synthesis method of the general formula (G1) will be described. In the above general formula (G1), when the group represented by the general formula (g1 ) is bonded to R 9 , it can be represented by the following general formula (G1-1). When the group represented by the general formula (g1) in the above general formula (G 1) is bonded to R 0 , it can be represented by the following general formula ( G1-2). Note that Cz, R to R 0 to R 9 , A r 4 , Ar 5 , Ar 6 , n and m in the organic compound represented by the following general formula (G1-1) and the organic compound represented by the following general formula (G1-2) are the same as the descriptions for the above general formula (G1), and thus the description will be omitted. For this reason, the description is omitted.

[0102] [Chemical]

[0103]

Chem.

[0104] As methods for synthesizing the organic compounds represented by general formulas (G1-1) and (G1-2), various reactions can be applied. For example, by performing the synthesis reactions shown below, the organic compounds represented by general formulas ( G1-1) and (G1-2) can be synthesized.

[0105] <Synthesis Method of Organic Compound Represented by General Formula (G1-1)> The organic compound represented by general formula (G1-1) of the present invention can be synthesized as shown in the following synthesis schemes (a-1) to (a-3).

[0106] That is, by coupling a benzonaphthofuran compound (Compound 1) and a diarylamine (Compound 2), a benzonaphthofuranylamino compound (G1-1) can be obtained. Or, by coupling a benzonaphthofuranylamine (Compound 3) and a compound having an aryl skeleton (Compound 4), a benzonaphthofuranylamino compound (G1-1) can be obtained. Or, by coupling a benzonaphthofuranylamine (Compound 5) and a compound having an aryl skeleton (Compound 6), a benzonaphthofuranylamino compound (G1-1) can be obtained. The following shows the synthesis schemes ( a-1) to (a-3). a-1) to (a-3).

[0107]

Chem.

[0108]

Chem.

[0109] [ka]

[0110] In the synthetic schemes (a-1) to (a-3), R 0 ~R 8 are each independently hydrogen a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, Alkoxy group, cyano group, halogen, haloalkyl group having 1 to 6 carbon atoms, and substituted or unsubstituted Cz represents any one of substituted aromatic hydrocarbon groups having 6 to 60 carbon atoms; represents a substituted carbazolyl group. 4 is a substituted or unsubstituted aromatic compound having 6 to 60 carbon atoms. represents any one of an aromatic hydrocarbon group, a substituted or unsubstituted carbazolyl group, and Ar 5 , A r 6 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. In addition, n represents any one of integers from 1 to 3, and m represents any one of integers from 0 to 3. represents, but Ar 4 When is a carbazolyl group, m is any one of integers 1 to 3. In addition, Ar 5 or Ar 6 may be multiple depending on the value of n or m, Number of Ar 5 or multiple Ar 6 each independently represents a substituted or unsubstituted 2-alkyl group having 6 to 54 carbon atoms; represents a 1-valent aromatic hydrocarbon group. 5 The number of carbon atoms in A is added to the total number of carbon atoms in A. r 4 and Ar 6 The sum of the carbon numbers of these is 60 or less.

[0111] In synthetic schemes (a-1) to (a-3), X 1 and X 4 and X 6 each independently represents chlorine, bromine, iodine, a triflate group, etc., and X 2 and X 3 and X 5 each independently represents hydrogen, an organotin group, etc.

[0112] When the reaction represented by synthetic schemes (a-1) to (a-3) is carried out by the Buchwald-Hartwig reaction using a palladium catalyst, palladium compounds such as bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), allylpalladium(II) chloride (dimer), etc. are used as catalysts and ligands such as tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohexylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, tri(ortho-tolyl)phosphine, (S)-(6,6′-dimethoxybiphenyl-2,2′-diyl)bis(diisopropylphosphine) (abbreviation: cBRIDP), etc. can be used. In this reaction (0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene palladium(II) dichloride, tetrakis(triphenylphosphine)palladium( 0), allylpalladium(II) chloride (dimer), etc. are used as catalysts , and organic bases such as sodium tert-butoxide and inorganic bases such as potassium carbonate, cesium carbonate , sodium carbonate, etc. can be used. In this reaction, solvents such as toluene , xylene, benzene, tetrahydrofuran, dioxane, etc. can be used. Note that the reagents that can be used in this reaction are not limited to the above-mentioned reagents. In addition, the reagents that can be used in this reaction are not limited to the above-mentioned reagents. In addition, the reagents that can be used in this reaction are not limited to the above-mentioned reagents. In addition, the reagents that can be used in this reaction are not limited to the above-mentioned reagents. In addition, the reagents that can be used in this reaction are not limited to the above-mentioned reagents. Note that the reagents that can be used in this reaction are not limited to the above-mentioned reagents.

[0113] In addition, in the reactions of the synthesis schemes (a-1) to (a-3), a urethane derivative using copper or a copper compound is used. When applying the Mann reaction, X 1 and X 4 and X 6 Each independently represents chlorine, bromine, and iodine. Represents X 2 and X 3 and X 5 represents hydrogen. In this reaction, copper or a copper compound is used. The base used can be an inorganic base such as potassium carbonate. The solvent that can be used in the reaction is 1,3-dimethyl-3,4,5,6-tetrahydrofuran. -2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc. In the Ullmann reaction, the desired product can be obtained in a shorter time and in a higher yield at a reaction temperature of 100°C or higher. Therefore, it is preferable to use DMPU and xylene, which have high boiling points. Since a higher temperature of 150°C or more is more preferable, it is more preferable to use DMPU. In the reaction, the reagents that can be used are not limited to those mentioned above. stomach.

[0114] <Method for synthesizing organic compound represented by general formula (G1-2)> The organic compound represented by the general formula (G1-2) can be synthesized by the following synthesis schemes (b-1) to (b-3) ) can be synthesized as follows.

[0115] That is, benzonaphthofuran compounds (compound 11) and diarylamines (compound 12) The benzonaphthofuranylamino compound (G1-2) is obtained by coupling with Alternatively, benzonaphthofuranylamine (compound 13) and an aryl skeleton can be used to obtain By coupling with a compound having the formula (Compound 4), a benzonaphthofuranyl a Alternatively, benzonaphthofuranylamine (compound G1-2) can be obtained. Compound 15) is coupled with a compound having an aryl skeleton (compound 6) to obtain The benzonaphthofuranylamino compound (G1-2) can be obtained. Schemes (b-1) to (b-3) are shown.

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] In the synthetic schemes (b-1) to (b-3), R 1 ~R 9 are each independently hydrogen a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, Alkoxy group, cyano group, halogen, haloalkyl group having 1 to 6 carbon atoms, and substituted or unsubstituted Cz represents any one of substituted aromatic hydrocarbon groups having 6 to 60 carbon atoms; represents a substituted carbazolyl group. 4 is a substituted or unsubstituted aromatic compound having 6 to 60 carbon atoms. Ar represents any one of an aromatic hydrocarbon group, a substituted or unsubstituted carbazolyl group, and 5 , A r 6 each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Represents any one of them. Also, n represents any one of the integers from 1 to 3, and m represents any one of the integers from 0 to 3 However, when Ar 4 is a carbazolyl group, m is any one of the integers from 1 to 3 Note that Ar 5 or Ar 6 There may be multiple cases depending on the numerical values of n or m. However, the plurality of Ar or the plurality of Ar 5 or the plurality of Ar 6 each independently represents any one of a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, the sum of the number of carbon atoms of Cz and Ar 5 and the sum of the number of carbon atoms of Ar 4 and Ar 6 are each 60 or less shall be.

[0120] In synthetic schemes (b-1) to (b-3), X 11 , X 4 and X 6 each independently represents chlorine, bromine, iodine, or a triflate group, and X 12 , X 13 and X 15 each independently represents hydrogen, an organotin group, etc.

[0121] When the reaction represented by synthetic schemes (b-1) to (b-3) is carried out by a Buchwald-Hartwig reaction using a palladium catalyst, palladium compounds such as bis(dibenzylideneacetone)palladium( 0), palladium(II) acetate, [1,1-bis(diphenylphosphino)ferrocene] palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0 ), allylpalladium(II) chloride (dimer), etc. are used as catalysts, and tri(tert-butyl)phosphine, tri(n-hexyl)phosphine, tricyclohe ​Xylylphosphine, di(1-adamantyl)-n-butylphosphine, 2-dicyclohex sylphosphino-2’,6’-dimethoxybiphenyl, tri(ortho-tolyl)phosphi ne, (S)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diisopro pylphosphine) (abbreviation: cBRIDP (registered trademark)), etc. can be used as ligands. In this reaction, organic bases such as sodium tert-butoxide, and inorganic bases such as potassium carbonate, cesium carbonate, sodium carbonate, etc. can be used. In this reaction, solvents such as toluene, xylene, benzene, tetrahydrofuran, dioxane, etc. can be used. The reagents that can be used in this reaction are not limited to the above-mentioned reagents. .

[0122] Also, when applying the Ullmann reaction using copper or a copper compound to the synthetic schemes (b-1) to (b-3), X 11 , X 4 and X 6 each independently represent chlorine, bromine, or iodine, X 12 , X 13 and X 15 represent hydrogen. In this reaction, copper or a copper compound can be used. Examples of the base used include inorganic bases such as potassium carbonate. In this reaction, solvents that can be used include 1,3-dimethyl-3,4,5,6-tetrahydro- 2(1H)pyrimidinone (DMPU), toluene, xylene, benzene, etc. In the Ullmann reaction, it is preferable to use DMPU or xylene with a high boiling point because a reaction temperature of 100 °C or higher can obtain the target product in a shorter time and with a higher yield. Moreover, since a higher temperature of 150 °C or higher is more preferable for the reaction temperature, it is more preferable to use DMPU. ​ In this reaction, the reagents that can be used are not limited to those mentioned above. .

[0123] In the above general formula (G1), (g1) is R 9 and the general formula (G In 1), (g1) is R 0 This is an explanation of the synthesis method of the general formula when the compound is bonded to one In the general formula (G1), (g1) is R 1 ~R 8 The same applies to the case where the That is, a method of synthesizing a benzonaphthofuran compound and an amine compound can be used. or a coupling reaction between a benzonaphthofuranylamine compound and a compound having an aryl group. The compound of general formula (G1) is synthesized by coupling reaction with the compound The synthesis method of the compound represented by the general formula (G1) is not limited to these. It is not.

[0124] Examples of amines that can be used in the synthesis of an organic compound according to one embodiment of the present invention are shown below. Among them, (700) to (739), (817) to (848), and (884) to (926) correspond to the above-mentioned compound 2 and compound 12, (740) to (816), and (849) to (883), and (927) to (945) are the above compounds 3 and Compound 5, Compound 13, and Compound 15 are equivalent to coupling with an appropriate organic compound. An organic compound that can synthesize an organic compound of one embodiment of the present invention by carrying out a reaction. It is an object.

[0125] [ka]

[0126]

Chem.

[0127]

Chem.

[0128]

Chem.

[0129]

Chem.

[0130]

Chem.

[0131]

Chem.

[0132]

Chem.

[0133]

Chem.

[0134]

Chem.

[0135]

Chem.

[0136]

Chem.

[0137]

Chem.

[0138]

Chem.

[0139]

Chem.

[0140] (Embodiment 2) FIG. 1 shows a diagram representing a light-emitting element according to an aspect of the present invention. The light-emitting element according to an aspect of the present invention has a first electrode 101, a second electrode 102, and an EL layer 103, and the above-described organic compound is included in the EL layer.

[0141] The EL layer 103 has a light-emitting layer 113, and may also have a hole injection layer 111, a hole transport layer 112, an electron transport layer 114, an electron injection layer 115, and the like. The organic compound according to an aspect of the present invention has hole-transporting properties and is therefore suitable for the hole injection layer 111, the hole transport layer 112, and the light-emitting layer 1 13.

[0142] The organic compound can also be used as a host material included in the light-emitting layer 113. Further by co-evaporating with an electron transport material, a structure that forms an exciplex with the electron transport material may be used. By forming an exciplex having an appropriate emission wavelength, effective energy transfer to the light-emitting material is realized, and it becomes possible to provide a light-emitting element having high efficiency and good lifetime.

[0143] ​​​​In addition, since the above hole transport material has good hole transport properties, it is effective to use it for the hole injection layer 111 and the hole transport layer 112. In particular, when a hole injection layer 111 is provided between the hole transport layer 112 and the first electrode 101, and an acceptor organic compound that facilitates hole injection from the electrode is used in the hole injection layer 111, it is suitable. When hole injection is performed using an acceptor organic compound, the compound contained in the hole transport layer 112 in contact with the hole injection layer 111 is preferably a hole transport material having a relatively shallow HOMO level in order to facilitate electron extraction by the acceptor organic compound. However, since it is difficult to inject holes into the light emitting layer 113 with a hole transport material having a shallow HOMO level, when the hole transport layer 112 made of such a hole transport material having a shallow HOMO level and the light emitting layer 113 are formed in contact with each other, carrier accumulation occurs at the interface, which may cause a decrease in the lifetime and efficiency of the light emitting device. Here, by providing a layer containing the organic compound described in Embodiment 1 between the hole transport material having a shallow HOMO level and the light emitting layer 113, it becomes possible to perform smooth hole injection into the light emitting layer, and an improvement in the lifetime and efficiency of the light emitting device is realized. That is, the above hole transport layer 112 has a first hole transport layer 112-1 and a second hole transport layer 112-2 from the hole injection layer 111 side. The first hole transport layer contains a first hole transport material, and the second hole transport layer contains the organic compound described in Embodiment 1. A light emitting device in which the HOMO level of the organic compound described in Embodiment 1 is deeper than the HOMO level of the first hole transport material can be a light emitting device having good lifetime and efficiency, and thus is a preferable configuration.

[0144] When hole injection is performed using an acceptor organic compound, the compound contained in the hole transport layer 112 in contact with the hole injection layer 111 is preferably a hole transport material having a relatively shallow HOMO level in order to facilitate electron extraction by the acceptor organic compound. However, since it is difficult to inject holes into the light emitting layer 113 with a hole transport material having a shallow HOMO level, when the hole transport layer 112 made of such a hole transport material having a shallow HOMO level and the light emitting layer 113 are formed in contact with each other, carrier accumulation occurs at the interface, which may cause a decrease in the lifetime and efficiency of the light emitting device. Here, by providing a layer containing the organic compound described in Embodiment 1 between the hole transport material having a shallow HOMO level and the light emitting layer 113, it becomes possible to perform smooth hole injection into the light emitting layer, and an improvement in the lifetime and efficiency of the light emitting device is realized. That is, the above hole transport layer 112 has a first hole transport layer 112-1 and a second hole transport layer 112-2 from the hole injection layer 111 side. The first hole transport layer contains a first hole transport material, and the second hole transport layer contains the organic compound described in Embodiment 1. A light emitting device in which the HOMO level of the organic compound described in Embodiment 1 is deeper than the HOMO level of the first hole transport material can be a light emitting device having good lifetime and efficiency, and thus is a preferable configuration.

[0145] That is, the above hole transport layer 112 has a first hole transport layer 112-1 and a second hole transport layer 112-2 from the hole injection layer 111 side. The first hole transport layer contains a first hole transport material, and the second hole transport layer contains the organic compound described in Embodiment 1. A light emitting device in which the HOMO level of the organic compound described in Embodiment 1 is deeper than the HOMO level of the first hole transport material can be a light emitting device having good lifetime and efficiency, and thus is a preferable configuration. ​​​​​​​ It should be noted that when the HOMO level of the first hole transport material is -5.4 eV or more, it is a preferable configuration because it is easy to extract electrons from the organic compound having an acceptor property.

[0146] In addition, the difference between the HOMO level of the first hole transport material and the HOMO level of the organic compound described in Embodiment 1 is 0.3 eV or less, more preferably 0.2 eV or less, which is preferable because it facilitates the injection of holes from the first hole transport layer 112-1 to the second hole transport layer 112-2.

[0147] In addition, the hole transport layer 112 may further have a third hole transport layer 112-3 between the second hole transport layer 112-2 and the light-emitting layer, and the third hole transport layer 112-3 may contain a third hole transport material. In this case, it is preferable that the HOMO level of the third hole transport material is deeper than the HOMO level of the organic compound described in Embodiment 1 contained in the second hole transport layer 112-2. Also, the difference between the HOMO level of the third hole transport material and the HOMO level of the organic compound described in Embodiment 1 contained in the second hole transport layer 112-2 is preferably 0.3 eV or less, more preferably 0.2 eV or less.

[0148] In addition, it is more preferable that the HOMO level of the third hole transport material is the same as or deeper than the HOMO level of the host material, because holes are moderately transported into the light-emitting layer, resulting in good lifetime and efficiency.

[0149] It should be noted that when the HOMO level of the light-emitting material is shallower (higher) than the HOMO level of the host material. In such a case, depending on the HOMO level of the hole transport layer, the injection of holes into the light-emitting material increases, and furthermore since holes are trapped in the light-emitting material, a decrease in lifetime due to the bias in the light-emitting region may be caused. In such a case, the application of the configuration of the above-described light-emitting device is suitable. As an example of a configuration that tends to be like this, a blue fluorescent device can be cited. The configuration of the present invention can be particularly preferably applied to an aromatic diamine compound that emits good blue fluorescence, particularly a pyrenediamine compound, a naphthobisbenzofluorene compound, etc., and a light-emitting device having good lifetime, efficiency, and chromaticity can be obtained.

[0150] Subsequently, detailed structures and examples of materials of the above-described light-emitting device will be described. The light-emitting device according to one aspect of the present invention has an EL layer 103 composed of a plurality of layers between a pair of electrodes of the first electrode 101 and the second electrode 102 as described above, and the EL layer 103 contains at least an organic compound according to one aspect of the present invention. Note that the layers included in the EL layer 103 are not particularly limited, and various layer structures such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a carrier blocking layer, an exciton blocking layer, and a charge generation layer can be applied.

[0151] The first electrode 101 is preferably formed using a metal, an alloy, a conductive compound having a large work function (specifically, 4.0 eV or more), and a mixture thereof. Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide , indium oxide-zinc oxide containing tungsten oxide and zinc oxide (IWZO), etc. can be cited. . These conductive metal oxide films are usually formed by sputtering, but may also be fabricated by applying methods such as the sol-gel method. As an example of the fabrication method, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 20 wt% of zinc oxide is added to indium oxide. There are also methods such as this. Further, indium oxide containing tungsten oxide and zinc oxide (IWZO) has tungsten oxide in an amount of 0. 5 to 5 wt% and zinc oxide in an amount of 0.1 to 1 wt% with respect to indium oxide, and can also be formed by sputtering using a target. In addition to this, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Co), copper (Cu), palladium (Pd), or nitrides of metal materials (for example, titanium nitride ) etc. can be mentioned. Graphene can also be used. By using it for the layer in contact with the first electrode 101 in the EL layer 103, regardless of the work function, the electrode material can be selected. Regarding the stacked structure of the EL layer 103, in the present embodiment, as shown in FIG. 1(A), in addition to the hole injection layer 111, hole transport layer 112, and light emitting layer 113, a configuration having an electron transport layer 114 and an electron injection layer

[0152] 115, and as shown in FIG. 1(B), in addition to the hole injection layer 111, hole transport layer 112, and light emitting layer 113, a configuration having an electron transport layer 114, an electron injection layer 115, and a charge generation layer 1 16 will be described for two types of configurations. The materials constituting each layer will be specifically shown below. The hole injection layer 111 is a layer containing a substance having acceptor properties. The configuration of one aspect of the present invention will be described for two types of configurations having a structure including an electron transport layer 114 and an electron injection layer 115 in addition to the hole injection layer 111, hole transport layer 112, and light emitting layer 113, and a structure including an electron transport layer 114, an electron injection layer 115, and a charge generation layer 116 in addition to the hole injection layer 111, hole transport layer 112, and light emitting layer 113 as shown in FIG. 1(B). The materials constituting each layer will be specifically shown below. Specifically shown below.

[0153] The hole injection layer 111 is a layer containing a substance having acceptor properties. The configuration of one aspect of the present invention When an organic compound having acceptor properties is used, it is a more suitable and appropriate configuration. As substances having acceptor properties, compounds having an electron-withdrawing group (halogen group or cyano group) can be used. 7,7,8,8-Tetracyano-2,3,5,6-tetrafluorobenzoquinodimethane (abbreviation: F4-TCNQ), 3,6-difluoro-2,5,7,7, 8,8-hexacyanoquinodimethane, chloranil, 2,3,6,7,10,11-hexa cyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) , 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ), etc. can be used. As the organic compound having acceptor properties, compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms, such as HAT-CN, are thermally stable and preferable. In addition, [3]radialene derivatives having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) are preferably used because they have very high electron acceptability. Specifically, α,α’,α’’-1,2,3-cyclopropanetriylidene tris 4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile], α,α’,α ’’-1,2,3-cyclopropanetriylidene tris[2,6-dichloro-3,5-di fluoro-4-(trifluoromethyl)benzeneacetonitrile], α,α’,α’’- 1,2,3-cyclopropanetriylidene tris[2,3,4,5,6-pentafluoro benzeneacetonitrile], etc. can be mentioned. As substances having acceptor properties, in addition to the organic compounds described above, molybdenum oxide, vanadium oxide, ruthenium oxide, etc. In addition to the organic compounds described above, substances having acceptor properties also include molybdenum oxide, vanadium oxide, ruthenium oxide, Tungsten oxide, manganese oxide, etc. can be used. In addition, phthalocyanine (abbreviation: H2Pc), phthalocyanine-based complex compounds such as copper phthalocyanine (CuPC), , 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), etc. of aromatic amine compounds, or poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. of polymers, etc., can also form the hole injection layer 111. The acceptor material can extract electrons from the adjacent hole transport layer (or hole transport material) by applying an electric field .

[0154] When an organic compound having acceptor properties is not used for the hole injection layer 111, as the material having acceptor properties, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, phthalocyanine (abbreviation : H2Pc), phthalocyanine-based compounds such as copper phthalocyanine (CuPC), 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: D NTPD), etc. of aromatic amine compounds, or poly(3,4-ethylenedioxythiophene) ) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. of polymers, etc., can also be used for hole injection . ​An implantation layer 111 can be formed.

[0155] In addition, the hole-injecting layer 111 may be formed by adding an acceptor substance to a substance having a hole-transporting property. A composite material containing an acceptor substance can also be used. By using a composite material with this structure, it is possible to select a material for forming the electrode regardless of its work function. That is, not only a material with a large work function but also a material with a small work function can be used for the first electrode 101. The acceptor materials in question are 7,7,8 ,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TC NQ), Chloranil, 1,3,4,5,7,8-Hexafluorotetracyano-naphthyl Acceptor organic compounds such as dimethyl ether (F6-TCNNQ) and transition metals In addition, the oxides of metals belonging to groups 4 to 8 of the periodic table can be used. The oxides of metals belonging to groups 4 to 8 of the periodic table can also be used. The oxides include vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, and molybdenum oxide. tungsten oxide, manganese oxide, rhenium oxide, etc. are preferred due to their high electron-accepting properties. Among them, molybdenum oxide is particularly suitable because it is stable in the air, has low hygroscopicity, and is easy to handle. This is preferable.

[0156] As hole transporting substances used in the composite material, aromatic amine compounds and carbazole derivatives are , aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. The following organic compounds can be used as hole transporting substances for the composite material: , 10 -6 cm 2Preferably, it is a substance having a hole mobility of 1 / Vs or more. In addition, the organic compound of one aspect of the present invention can also be preferably used. Hereinafter, organic compounds that can be used as hole transporting substances in the composite material will be specifically listed. The organic compounds of one aspect of the invention can also be preferably used. Hereinafter, organic compounds that can be used as hole transporting substances in the composite material will be specifically listed. Hereinafter, organic compounds that can be used as hole transporting substances in the composite material will be specifically listed.

[0157] Examples of aromatic amine compounds that can be used in the composite material include N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4' -bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl} -N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl amino]benzene (abbreviation: DPA3B), and the like. Examples of carbazole derivatives include, specifically, 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl amino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl carbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1 ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri s[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), and the like. Examples of carbazole derivatives include, specifically, 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), and the like. 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenyl Benzene or the like can be used. Examples of the aromatic hydrocarbon include 2-tert- butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-te rt-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5- diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9,1 0-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10- di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth ), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2 -tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tet ramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl -9,10-di(2-naphthyl)anthracene, 9,9’-bianthryl, 10,10’ -diphenyl-9,9’-bianthryl, 10,10’-bis(2-phenylphenyl) -9,9’-bianthryl, 10,10’-bis[(2,3,4,5,6-pentaphen yl)phenyl]-9,9’-bianthryl, anthracene, tetracene, rubrene, pery lene, 2,5,8,11-tetra(tert-butyl)perylene and the like. In addition, pentacene, coronene and the like can also be used. It may have a vinyl skeleton . Examples of the aromatic hydrocarbon having a vinyl group include 4,4’-bis(2,2-di (Phenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-di (phenylvinyl)phenyl]anthracene (abbreviation: DPVPA), etc. may be mentioned. Incidentally, The organic compound of one embodiment of the present invention can also be used.

[0158] Also, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenyl lamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino )phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis( (phenyl)benzidine] (abbreviation: Poly-TPD), etc., high molecular compounds can also be used.

[0159] By forming the hole injection layer 111, the injectability of holes becomes good, and a light emitting element with a small driving voltage can be obtained. In addition, the organic compound having an acceptor property is easy to deposit and easy to form a film, so it is a material that is easy to use.

[0160] The hole transport layer 112 is formed including a hole transport material. As the hole transport material, 1×1 0 -6 cm 2 / Vs or more hole mobility is preferably provided. It is preferable that the hole transport layer 112 contains the hole transport material of one embodiment of the present invention. By including the organic compound of one embodiment of the present invention described in Embodiment 1 in the hole transport layer 112, a light emitting element with a long life and good efficiency can be obtained.

[0161] In particular, when an organic compound having an acceptor property is used as the hole injection layer 111, at least ​The hole transport layer 112 may also be formed of two layers, a first hole transport layer 112-1 and a second hole transport layer 112-2. The first hole transport layer 112-1 is formed of a first hole transport material having a relatively shallow HOMO level, and the second hole transport layer 112-2 has a structure containing the organic compound described in Embodiment 1. By doing so, a light-emitting device with a long lifespan and high efficiency can be obtained. Since the difference between the LUMO level of the acceptor organic compound and the HOMO level of the first hole transport material varies depending on the strength of the acceptor property of the acceptor organic compound, although not particularly limited, generally, if the level difference is about 1 eV or less, holes can be injected. When HAT-CN is used as the acceptor organic compound, the LUMO level of HAT-CN is estimated to be -4.41 eV from cyclic voltammetry measurements, and the HOMO level of the first hole transport material is preferably -5.4 eV or higher. However, if the HOMO level of the first hole transport material becomes too high, the hole injection property into the second hole transport material deteriorates. Also, since the work function of an anode such as ITO is around -5 eV, using a first hole transport material with a higher HOMO level is disadvantageous. Therefore, the HOMO level of the first hole transport material is preferably -5.0 eV or lower. A third hole transport layer 112-3 may be further formed between the second hole transport layer and the light-emitting layer. The third hole transport layer 112-3 contains a third hole transport material. The first hole transport layer 112-1, the second hole transport layer 112-2, and the third hole transport layer 112

[0162] The difference between the LUMO level of the acceptor organic compound and the HOMO level of the first hole transport material varies depending on the strength of the acceptor property of the acceptor organic compound. Therefore, although not particularly limited, generally, if the level difference is about 1 eV or less, holes can be injected. When HAT-CN is used as the acceptor organic compound, the LUMO level of HAT-CN is estimated to be -4.41 eV from cyclic voltammetry measurements. and the HOMO level of the first hole transport material is preferably -5.4 eV or higher. However, if the HOMO level of the first hole transport material becomes too high, the hole injection property into the second hole transport material deteriorates. Also, since the work function of an anode such as ITO is around -5 eV, using a first hole transport material with a higher HOMO level is disadvantageous. Therefore, the HOMO level of the first hole transport material is preferably -5.0 eV or lower. In addition, a third hole transport layer 112-3 may be further formed between the second hole transport layer and the light-emitting layer. The third hole transport layer 112-3 contains a third hole transport material. The first hole transport layer 112-1, the second hole transport layer 112-2, and the third hole transport layer 112

[0163] In addition, a third hole transport layer 112-3 may be further formed between the second hole transport layer and the light-emitting layer. The third hole transport layer 112-3 contains a third hole transport material.

[0164] -1, and the third hole transport layer 112 ​Regarding -3, since the explanation has been given above, the repetitive explanation will be omitted. Note that for each Regarding the hole transport material contained in , from the materials having hole transport properties described above, or from among various other materials having hole transport properties, a material that matches the relationship between the layers may be

[0165] The light - emitting layer 113 is a layer containing a light - emitting material. The light - emitting material may be a fluorescent light - emitting substance, a phosphorescent light - emitting substance, a substance showing thermally activated delayed fluorescence (TADF), or any other light - emitting material. Also, it may be a single layer or may be composed of a plurality of layers containing different light - emitting materials. Note that one aspect of the present invention is that the light - emitting layer 113 is a layer that exhibits fluorescent light emission, and particularly, it can be more preferably applied when it is a layer that exhibits blue fluorescent light emission.

[0166] In the light - emitting layer 113, examples of the materials that can be used as the fluorescent light - emitting substance include, for example, the following. Also, fluorescent light - emitting substances other than these can also be used.

[0167] 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’ - diphenyl - N,N’ - bis[4-(9 - phenyl - 9H - fluoren - 9 - yl )phenyl]pyrene - 1,6 - diamine (abbreviation: 1,6FLPAPrn), N,N’ - bi s(3 - methylphenyl)-N,N’ - bis[3-(9 - phenyl - 9H - fluoren - 9 - yl)phenyl]pyrene - 1,6 - diamine (abbreviation: 1,6mMemFLPAPrn ), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-di phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbaz ol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)tri phenylamine (abbreviation: 2YGAPPA), N,9-diphenyl-N-[4-(10 -phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl )triphenylamine (abbreviation: PCBAPA), N,N''-(2-tert-butyl anthracene-9,10-diyl-di-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: 2DPAP PA), N,N,N',N',N'',N'',N''',N'''-octaphenyldibenz[g,p]chryse ne-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N -(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3- amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-y l)phenyl]- N-[2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation : 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N’,N ’-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,1 0-bis(1,1’-biphenyl-2-yl)-2-anthryl]-N,N’,N’-t riphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1’-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)ph enyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N ,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA) Coumarin 545 T, N,N’-diphenylquinacridone, (abbreviation: DPQd), Rubrene, 5,12-bis (1,1’-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl yl-6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoliz in-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N’,N’-tetrakis(4-methylphenyl)tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N’,N’ -tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizin -9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-te trahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pi ran-4-ylidene}propanedinitrile (abbreviation: BisDCJTM), N,N’-(pi rene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d] furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), etc. are mentioned. In particular , condensed aromatic diamine compounds typified by pyrenediamine compounds such as 1,6FLPAPrn, 1,6mMemFLPAPrn, and 1,6BnfAPrn-03 are preferable because they have high hole transport properties and are excellent in luminous efficiency and reliability. In the light-emitting layer 113, examples of materials that can be used as the phosphorescent material include

[0168] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H The following are mentioned.

[0169] tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium(III )(abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4-diphenyl -4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mpt z)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3 b)3]) and other organometallic iridium complexes having a 4H-triazole skeleton, tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-tri azolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1 -methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (abbreviation: [Ir(Prptz1-Me)3]) and other organometallic iridium complexes having a 1H-triazole skeleton, fac-tris[1-(2,6-diisopropyl phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), tris[3-(2,6-dimethylphenyl)-7-methylimi (dazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmp impt-Me)3]) and other organometallic iridium complexes having an imidazole skeleton, bis[2-(4’,6’-difluorophenyl)pyridinato-N,C iridium( 2’ iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4’ ,6’-difluorophenyl)pyridinato-N,C iridium(III) picolinate 2’ iridium(III) picolinate -to (abbreviation: FIrpic), bis{2-[3’,5’-bis(trifluoromethyl)ph enyl]pyridinato-N,C 2’}iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4’,6’-difluorophenyl)pyr dinato-N,C 2’ iridium(III) acetylacetonate (abbreviation: FIr(ac ac)) and other organometallic ir idium complexes having a phenylpyridine derivative having an electron-withdrawing group as a ligand are exemplified. These are compounds that exhibit blue phosphorescent emission and are compounds having a peak of emission from 440 nm to 520 nm.

[0170] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)iri dium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpy rimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) Organometallic iridium complexes having a pyrimidine skeleton such as (abbreviation: [Ir(dppm)2(acac)]), and organometallic iridium complexes having a pyrazine skeleton such as (acetylacetonato)bis(3,5-dimethyl-2-phenyl pyridazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyr idazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]), and organometallic iridium complexes having a pyridine skeleton such as tris(2-phenylpyrid 2’ nato-N,C )iridium(III) (abbreviation: [Ir(ppy)3]), bis(2- 2’ phenylpyridinato-N,C )iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium(I II) acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(be nzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris (2-phenylquinolinato-N,C 2’ )iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ )iridium(III) acetylacet onate (abbreviation: [Ir(pq)2(acac)]). In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)ter bium(III) (abbreviation: [Tb(acac)3(Phen)]) are included. These are mainly compounds that exhibit green phosphorescent emission and have an emission peak at 500 nm to 6 00 nm. Note that organometallic iridium complexes having a pyrimidine skeleton The body is particularly preferable because it is outstanding in terms of reliability and luminous efficiency.

[0171] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( [naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]) and other organometallic iridium complexes having a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-triphenylpyrazinato )iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(F dpq)2(acac)]) and other organometallic iridium complexes having a pyrazine skeleton, and tris(1-phenylisoquinolinato-N,C )iridium(III) (abbreviation: [I r(piq)3]), bis(1-phenylisoquinolinato-N,C )iridium(II II) acetylacetonate (abbreviation: [Ir(piq)2(acac)]) and other organometallic iridium complexes having a pyrazine skeleton, and in addition, 2,3,7,8,12,13,17,1 2’ )iridium(III) (abbreviation: [I r(piq)3]), bis(1-phenylisoquinolinato-N,C 2’ )iridium(II II) acetylacetonate (abbreviation: [Ir(piq)2(acac)]) and other organometallic iridium complexes having a pyrazine skeleton, and in addition, 2,3,7,8,12,13,17,1 8-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as, tris(1,3-diphenyl-1,3-propanedionato)(mono phenanthroline)europium(III)(abbreviation: [Eu(DBM)3(Phen)]) , tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophen anthroline)europium(III)(abbreviation: [Eu(TTA)3(Phen)]) and the like of rare earth metal complexes can be mentioned. These are compounds that exhibit red phosphorescent emission and have an emission peak at 6 00 nm to 700 nm. In addition, organometallic iridium complexes having a pyrazine skeleton can obtain red emission with good chromaticity.

[0172] In addition to the phosphorescent compounds described above, known phosphorescent materials can also be selected and used.

[0173] As the TADF material, fullerenes and their derivatives, acridines and their derivatives, eosin derivatives, etc. can be used. In addition, metal-containing porphyrins containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d), etc. can be mentioned. Examples of the metal-containing porphyrin include, for example, protoporphyrin-tin fluoride complex (SnF2(Pro to IX)), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), etioporphyrin -tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -tin fluoride complex (SnF2(OEP)), etioporphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin - Examples also include platinum chloride complex (PtCl2OEP), etc.

[0174]

Chemical formula

[0175] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-f enylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine( Abbreviation: PIC-TRZ), 9-(4,6-diphenyl-1,3,5-triazin-2- yl)-9’-phenyl-9H,9’H-3,3’-bicarbazole (abbreviation: PCCzT zn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-c arbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbre viation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl -4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4 -(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5- diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-di methyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACR XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10’H-spiro[a cridine-9,9’-anthracene]-10’-one (abbreviation: ACRSA), etc. Heterocyclic compounds having both an π-electron excessive type heteroaromatic ring and an π-electron deficient type heteroaromatic ring can also be used. It is possible. Since the heterocyclic compound has a π-electron-excessive heterocyclic aromatic ring and a π-electron-deficient heterocyclic aromatic ring, it has both high electron transportability and hole transportability, which is preferable. Note that a substance in which a π-electron-excessive heterocyclic aromatic ring and a π-electron-deficient heterocyclic aromatic ring are directly bonded has both strong donor properties of the π-electron-excessive heterocyclic aromatic ring and acceptor properties of the π-electron-deficient heterocyclic aromatic ring, and the energy gap between the S1 level and the T1 level becomes small. Therefore, it is particularly preferable because thermally activated delayed fluorescence can be efficiently obtained. Note that instead of the π-electron-deficient heterocyclic aromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used. Since it has, it is both highly electron transporting and hole transporting, which is preferable. A substance in which a π-electron-excessive heterocyclic aromatic ring and a π-electron-deficient heterocyclic aromatic ring are directly bonded has both strong donor properties of the π-electron-excessive heterocyclic aromatic ring and acceptor properties of the π-electron-deficient heterocyclic aromatic ring, and the energy gap between the S1 level and the T1 level becomes small, so thermally activated delayed fluorescence can be efficiently obtained, which is particularly preferable. Note that instead of the π-electron-deficient heterocyclic aromatic ring, an aromatic ring to which an electron-withdrawing group such as a cyano group is bonded may be used.

[0176]

Chemical formula

[0177] As the host material of the light-emitting layer, various carrier transport materials such as materials having electron transportability and materials having hole transportability can be used.

[0178] Examples of the material having hole transportability include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), 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), 4-phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine ( Abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carb azole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naph thyl)-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), 9,9-dime thyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl amine (abbreviation: PCBAF), N-phenyl-N-[4-(9- phenyl-9H-carbazole-3-yl)phenyl]spiro-9,9'-bifluorene -2-amine (abbreviation: PCBASF), etc. Compounds having an aromatic amine skeleton, 1,3 -bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl yl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9- phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carb azole)(abbreviation: PCCP), etc. Compounds having a carbazole skeleton, 4,4',4 ''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT 3P-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-phenyldibenzothiop hene (abbreviation: DBTFLP-IV), etc. Compounds having a thiophene skeleton, 4,4', 4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3 P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), etc., having a furan skeleton Compounds are exemplified. Among those described above, compounds having an aromatic amine skeleton or a carbazole skeleton are preferred because they have good reliability, high hole transportability, and contribute to reducing the driving voltage. Also, the organic compounds described in Embodiment 1 can also be preferably used as well. It is possible.

[0179] Examples of materials having electron transporting properties include, for example, bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenylphenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenylphenolato]zinc(II) (abbreviation: ZnBTZ), etc., metal complexes, and 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation : PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2-[3’-(9,9-dimethyl-9H-fluoren-2-yl)-1,1’-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation : OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)- yl]fluorene (abbreviation: FODPA), etc. 9-[3-(Dibenzothiophen-4-yl)phenyl]-9H-carbazole (abbreviation: CO11), 2,2’,2’’-(1,3 ,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl- 1H-benzimidazole (abbreviation: mDBTBIm-II), 2-{4-[9,10-di (naphthalen-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benz imidazole (abbreviation: ZADN), and other heterocyclic compounds having a polyazole skeleton, 2- [3-(dibenzothiophen-4-yl)phenyl]dibenz[f,h]quinoxaline( abbreviation: 2mDBTPDBq-II), 2-[3’-(dibenzothiophen-4-yl)bi phenyl-3-yl]dibenz[f,h]quinoxaline (abbreviation: 2mDBTBPDBq- II), 2-[3’-(9H-carbazol-9-yl)biphenyl-3-yl]dibenz zo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phena thren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6- bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2 Pm-II), and other heterocyclic compounds having a diazine skeleton, 3,5-bis[3-(9H- carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5 -tri[3-(3-pyridyl)-phenyl]benzene (abbreviation: TmPyPB), and other heterocyclic compounds having a pyr idine skeleton. Among the above, heterocyclic compounds having a diazine skeleton and heterocyclic compounds having a pyridine skeleton are preferred because of their good reliability. In particular ​Heterocyclic compounds with a diazine (pyrimidine or pyrazine) skeleton have high electron transport properties. It also contributes to reducing the driving voltage.

[0180] When a fluorescent substance is used as a light-emitting material, the host material is a material having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used in the form of an anthraquinone, it is possible to realize a light-emitting layer having excellent light-emitting efficiency and durability. Since many materials having a Cene skeleton have a deep HOMO level, one embodiment of the present invention is preferably applied to The host material may be a dianthracene skeleton material. Substances with a phenylanthracene skeleton, especially a 9,10-diphenylanthracene skeleton, It is preferable because it is chemically stable. In addition, when the host material has a carbazole skeleton, This is preferable because it enhances the hole injection and transport properties, but the benzene ring is further condensed to the carbazole. In the case of the benzocarbazole skeleton, the HOMO is shallower than that of carbazole by about 0.1 eV. In particular, the host material is preferably dibenzocarbazo When the carbazole skeleton is included, the HOMO is shallower by about 0.1 eV than that of carbazole, and holes can enter. This is preferable because it is easy to form the hole transport layer, has excellent hole transport properties, and has high heat resistance. Further, preferred host materials include those having a 9,10-diphenylanthracene skeleton and Carbazole skeleton (or benzocarbazole skeleton or dibenzocarbazole skeleton) From the viewpoint of the hole injection and transport properties, the carbazole skeleton is Alternatively, a benzofluorene skeleton or a dibenzofluorene skeleton may be used. An example of a substance is 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl] Ru-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)phenyl -9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phen yl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7- [4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carb azole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anth ryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA ), 9-phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphe nyl-4’-yl}anthracene (abbreviation: FLPPA), etc. can be mentioned. In particular, CzPA , cgDBCzPA, 2mBnfPPA, PCzPA show very good characteristics, so they are preferred choices.

[0181] In addition, the light-emitting element of one aspect of the present invention is particularly preferably applied to a light-emitting element that exhibits blue fluorescence emission.

[0182] Note that the host material may be a material in which a plurality of substances are mixed. When using the mixed host material , it is preferable to mix a material having electron-transporting properties and a material having hole-transporting properties. By mixing a material having electron-transporting properties and a material having hole-transporting properties , the transport properties of the light-emitting layer 113 can be easily adjusted, and the control of the recombination region can also be easily performed. The ratio of the content of the material having hole-transporting properties to the material having electron-transporting properties may be hole-transporting material: electron-transporting material = 1:9 to 9:1.

[0183] In addition, an exciplex may be formed between these mixed materials. The exciplex is a luminescent material that forms an exciplex exhibiting luminescence that overlaps with the wavelength of the absorption band on the lowest energy side of the luminescent material . By selecting such a combination, energy transfer becomes smooth and efficient luminescence can be obtained, which is preferable. Also, using this configuration is preferable because the driving voltage is also reduced.

[0184] The electron transport layer 114 is a layer containing a substance having electron transporting properties. As the substance having electron transporting properties, those mentioned as the substance having electron transporting properties that can be used for the above host material can be used.

[0185] Between the electron transport layer 114 and the second electrode 102, as an electron injection layer 115, lithium fluoride (LiF), lithium 8-hydroxyquinolinate (abbreviation: Liq), cesium fluoride (CsF), calcium fluoride (CaF2), etc., a layer containing an alkali metal or an alkaline earth metal or a compound thereof may be provided. The electron injection layer 115 is obtained by incorporating an alkali metal or an alkaline earth metal or a compound thereof into a layer made of a substance having electron transporting properties, or an electride may be used. Examples of the electride include a substance obtained by adding electrons to a mixed oxide of calcium and aluminum at a high concentration.

[0186] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Fig. 1(B)). The charge generation layer 116 is a layer that can inject holes into the layer in contact with the cathode side of the layer and electrons into the layer in contact with the anode side by applying a potential. The charge generation layer 116 includes at least a P-type layer 117. The P-type layer 117 constitutes the above-mentioned hole injection layer 111. It is preferable to form using the composite material listed as the material that can be used. Also, P-type layer 1 17 may be configured by laminating a film containing the acceptor material described above as the material constituting the composite material and a film containing a hole transport material . By applying a potential to the P-type layer 117, electrons are injected into the electron transport layer 114 and holes are injected into the second electrode 102 which is the cathode, and the light-emitting element operates .

[0187] Note that the charge generation layer 116 preferably has either or both of an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117.

[0188] The electron relay layer 118 contains at least a substance having electron transporting properties and has a function of preventing the interaction between the electron injection buffer layer 1 19 and the P-type layer 117 and smoothly transferring electrons. The LUMO level of the substance having electron transporting properties contained in the electron relay layer 118 is preferably between the LUMO level of the acceptor substance in the P-type layer 117 and the LUMO level of the substance contained in the layer in contact with the charge generation layer 116 in the electron transport layer 114 . The specific energy level of the LUMO level of the substance having electron transporting properties used in the electron relay layer 11 8 is preferably -5.0 eV or more, more preferably -5.0 eV or more and -3.0 eV or less. Note that as the substance having electron transporting properties used in the electron relay layer 118, it is preferable to use a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand. The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and these compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate, etc.))

[0189] ​​(including carbonates such as thium and cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates), or compounds of rare earth metals (including oxides, halides, carbonates)) and other substances with high electron injection properties can be used. (including oxides, halides, carbonates), or compounds of rare earth metals (including oxides, halides, carbonates)) It is possible to use substances with high electron injection properties such as

[0190] In addition, when the electron injection buffer layer 119 is formed by including a substance having electron transporting properties and a donor substance, as the donor substance, alkali metals, alkaline earth metals, rare earth metals, and their compounds (alkali metal compounds (including oxides such as lithium oxide, halides, carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (including oxides, halides, carbonates), or compounds of rare earth metals (including oxides, halides, carbonates)), in addition to organic compounds such as tetrathianaphthacene (abbreviation: TTN), nickelocene, decamethyl nickelocene can also be used. Note that as the substance having electron transporting properties, it can be formed using the same materials as those constituting the electron transport layer 114 described above.

[0191] As the substance for forming the second electrode 102, metals, alloys, electroconductive compounds, and mixtures thereof having a small work function (specifically, 3.8 eV or less) can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs), and elements belonging to Group 1 or Group 2 of the periodic table such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing these (MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, etc. However, between the second electrode 102 and the electron transport layer, ​ By providing an electron injection layer, various conductive materials such as Al, Ag, ITO, indium tin oxide containing silicon or silicon oxide can be used as the second electrode 102 regardless of the work function. These conductive materials can be formed into a film using dry methods such as vacuum evaporation and sputtering, inkjet method, spin coating method, etc. Also, it may be formed by a wet method using the sol-gel method, or may be formed by a wet method using a paste of a metal material.

[0192] In addition, as a method for forming the EL layer 103, various methods can be used regardless of dry or wet methods. For example, vacuum evaporation method, gravure printing method, offset printing method, screen printing method, inkjet method or spin coating method can be used.

[0193] Also, each of the above electrodes or layers may be formed using different film formation methods.

[0194] Note that the configuration of the layer provided between the first electrode 101 and the second electrode 102 is not limited to the above. However, in order to suppress quenching caused by the proximity of the light emitting region to the electrodes and the metal used in the carrier injection layer, a configuration in which a light emitting region where holes and electrons recombine is provided at a site distant from the first electrode 101 and the second electrode 1 02 is preferable. 02.

[0195] In addition, the hole transport layer or electron transport layer in contact with the light emitting layer 113, particularly the carrier transport layer close to the recombination region in the light emitting layer 113, suppresses energy transfer from the excitons generated in the light emitting layer. Therefore, its band gap is the light emitting material constituting the light emitting layer or the light emitting contained in the light emitting layer It is preferable that the material is made of a substance having a larger band gap than the material. I wish.

[0196] Next, we developed a light-emitting device having a structure in which multiple light-emitting units are stacked (a stacked type device, a tandem type device, etc.). The embodiment of the light-emitting device (also referred to as a "light-emitting device") will be described with reference to FIG. 1(C). A light-emitting element having a plurality of light-emitting units between the light-emitting element and the light-emitting device. 1C). The device is a light-emitting element having a plurality of light-emitting units, and is the light-emitting element shown in FIG. 1(A) or FIG. 1(B). An optical element can be said to be a light-emitting element having one light-emitting unit.

[0197] In FIG. 1C, a first light-emitting unit is disposed between a first electrode 501 and a second electrode 502. The first light-emitting unit 511 and the second light-emitting unit 512 are stacked. A charge generating layer 513 is provided between the first electrode 5 and the second light-emitting unit 512. 1A and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 02, and the same as that described in the explanation of FIG. 1(A) can be applied. The first light emitting unit 511 and the second light emitting unit 512 may have the same configuration or different configurations. It may be composed of

[0198] The charge generating layer 513 generates a charge when a voltage is applied between the first electrode 501 and the second electrode 502. It has the function of injecting electrons into one light-emitting unit and injecting holes into the other light-emitting unit. That is, in FIG. 1(C), the potential of the anode is set higher than the potential of the cathode. When a voltage is applied, the charge generating layer 513 injects electrons into the first light-emitting unit 511, Any device that injects holes into the second light-emitting unit 512 may be used.

[0199] The charge generation layer 513 is formed with the same configuration as the charge generation layer 116 described in FIG. 1(B). This is preferable. Since the composite material of the organic compound and the metal oxide is excellent in carrier injection property and carrier transport property, low-voltage driving and low-current driving can be realized. When the surface on the anode side of the light-emitting unit is in contact with the charge generation layer 513, the charge generation layer 513 can also serve as the hole injection layer of the light-emitting unit, so the light-emitting unit may not be provided with a hole injection layer. In addition, when an electron injection buffer layer 119 is provided in the charge generation layer 513, since the electron injection buffer layer 119 serves as the electron injection layer in the light-emitting unit on the anode side, it is not always necessary to form an electron injection layer in the light-emitting unit on the anode side. In FIG. 1(C), a light-emitting element having two light-emitting units has been described, but the same can be similarly applied to a light-emitting element in which three or more light-emitting units are stacked. By arranging a plurality of light-emitting units between a pair of electrodes with the charge generation layer 513 as a partition as in the light-emitting element according to the present embodiment, high-brightness light emission can be enabled while keeping the current density low, and furthermore, a long-life element can be realized. In addition, a light-emitting device that enables low-voltage driving and has low power consumption can be realized. Moreover, by making the emission colors of the respective light-emitting units different, light emission of a desired color can be obtained for the entire light-emitting element. For example, in a light-emitting element having two light-emitting units, if the emission colors of the two light-emitting units are made different, light emission of a desired color can be obtained for the entire light-emitting element.

[0200] When an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer layer 119 serves as the electron injection layer in the light-emitting unit on the anode side, so it is not always necessary to form an electron injection layer in the light-emitting unit on the anode side. When an electron injection buffer layer 119 is provided in the charge generation layer 513, since the electron injection buffer layer 119 serves as the electron injection layer in the light-emitting unit on the anode side, it is not always necessary to form an electron injection layer in the light-emitting unit on the anode side. When an electron injection buffer layer 119 is provided in the charge generation layer 513, since the electron injection buffer layer 119 serves as the electron injection layer in the light-emitting unit on the anode side, it is not always necessary to form an electron injection layer in the light-emitting unit on the anode side.

[0201] In FIG. 1(C), a light-emitting element having two light-emitting units has been described, but the same can be similarly applied to a light-emitting element in which three or more light-emitting units are stacked. By arranging a plurality of light-emitting units between a pair of electrodes with the charge generation layer 513 as a partition as in the light-emitting element according to the present embodiment, high-brightness light emission can be enabled while keeping the current density low, and furthermore, a long-life element can be realized. In addition, a light-emitting device that enables low-voltage driving and has low power consumption can be realized. Moreover, by making the emission colors of the respective light-emitting units different, light emission of a desired color can be obtained for the entire light-emitting element. For example, in a light-emitting element having two light-emitting units, if the emission colors of the two light-emitting units are made different, light emission of a desired color can be obtained for the entire light-emitting element.

[0202] Moreover, by making the emission colors of the respective light-emitting units different, light emission of a desired color can be obtained for the entire light-emitting element. For example, in a light-emitting element having two light-emitting units, In this case, a red and green emission color is obtained from the first light-emitting unit, and a blue emission color is obtained from the second light-emitting unit. By doing so, it is also possible to obtain a light-emitting element that emits white light as the entire light-emitting element.

[0203] Further, each layer such as the above-described EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and the charge generation layer and the electrodes can be formed, for example, by methods such as vapor deposition (including vacuum vapor deposition), droplet discharge method (also called inkjet method), coating method, gravure printing method, etc. They can be formed using methods such as the inkjet method (also called the droplet discharge method), coating method, gravure printing method, etc. Further, they may contain a low molecular weight material, a medium molecular weight material (including oligomers and dendrimers), or a high molecular weight material. They may also contain a low molecular weight material, a medium molecular weight material (including oligomers and dendrimers), or a high molecular weight material.

[0204] (Embodiment 3) In this embodiment, a light-emitting device using the light-emitting element described in Embodiment 2 will be described.

[0205] In this embodiment, a light-emitting device manufactured using the light-emitting element described in Embodiment 2 will be described with reference to FIG. 2. Note that FIG. 2(A) is a top view showing the light-emitting device, and FIG. 2(B) is a cross-sectional view of FIG. 2 (A) cut along A-B and C-D. This light-emitting device includes a drive circuit portion (source line drive circuit) 601, a pixel portion 602, and a drive circuit portion (gate line drive circuit) 603, which are indicated by dotted lines, for controlling the light emission of the light-emitting element. Further, 604 is a sealing substrate , and 605 is a sealing material. The inside surrounded by the sealing material 605 is a space 607. .

[0206] Note that the routing wiring 608 is a wiring for transmitting signals input to the source line drive circuit 601 and the gate line drive circuit 603, and is a flexible printed circuit (FPC) that serves as an external input terminal. Video signals, clock signals, start signals, reset signals, etc. are input from 609 to the source line drive circuit 601 and the gate line drive circuit 603. Although only the FPC is shown here, the FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself, but also the state in which an FPC or PWB is attached to it. do.

[0207] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601 and a pixel portion are formed. 6, one pixel in the pixel area 602 is shown.

[0208] The element substrate 610 may be made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of resin such as fluoride, polyester or acrylic resin. It is sufficient to manufacture it.

[0209] The structure of the transistors used in the pixels and the driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium, etc., can be used. Alternatively, indium, such as In-Ga-Zn based metal oxides, Alternatively, an oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0210] The crystallinity of the semiconductor material used in the transistor is not particularly limited. Any semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or semiconductor having a crystalline region in part) may be used. Using a semiconductor having crystallinity is preferable because deterioration of transistor characteristics can be suppressed. Here, in addition to the transistors provided in the pixel and the drive circuit, it is preferable to apply an oxide semiconductor to semiconductor devices such as transistors used for a touch sensor described later. Particularly, it is preferable to apply an oxide semiconductor having a wider bandgap than silicon. By using an oxide semiconductor having a wider bandgap than silicon, the current in the off state of the transistor can be reduced.

[0211] Here, in addition to the transistors provided in the above pixel and drive circuit, it is preferable to apply an oxide semiconductor to semiconductor devices such as transistors used for a touch sensor described later. Particularly, it is preferable to apply an oxide semiconductor having a wider bandgap than silicon. By using an oxide semiconductor having a wider bandgap than silicon, the current in the off state of the transistor can be reduced. The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). Further, it is more preferable that the oxide semiconductor is an oxide semiconductor containing an oxide represented by In-M-Zn-based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf). Particularly, as the semiconductor layer, it is preferable to use an oxide semiconductor film having a plurality of crystal parts, wherein the c-axis of the crystal part is oriented perpendicular to the surface to be formed of the semiconductor layer or the upper surface of the semiconductor layer, and there is no grain boundary between adjacent crystal parts. By using such a material as the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized.

[0212] Further, the transistor having the above semiconductor layer can hold the charge accumulated in the capacitor through the transistor for a long period of time due to its low off-current. Here, in addition to the transistors provided in the above pixel and drive circuit, it is preferable to apply an oxide semiconductor to semiconductor devices such as transistors used for a touch sensor described later. Particularly, it is preferable to apply an oxide semiconductor having a wider bandgap than silicon. By using an oxide semiconductor having a wider bandgap than silicon, the current in the off state of the transistor can be reduced. The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). Further, it is more preferable that the oxide semiconductor is an oxide semiconductor containing an oxide represented by In-M-Zn-based oxide (M is a metal such as Al, Ti, Ga, Ge, Y, Zr, Sn, La, Ce or Hf).

[0213] Particularly, as the semiconductor layer, it is preferable to use an oxide semiconductor film having a plurality of crystal parts, wherein the c-axis of the crystal part is oriented perpendicular to the surface to be formed of the semiconductor layer or the upper surface of the semiconductor layer, and there is no grain boundary between adjacent crystal parts. By using such a material as the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized. Further, the transistor having the above semiconductor layer can hold the charge accumulated in the capacitor through the transistor for a long period of time due to its low off-current.

[0214] By using such a material as the semiconductor layer, fluctuations in electrical characteristics are suppressed, and a highly reliable transistor can be realized. Further, the transistor having the above semiconductor layer can hold the charge accumulated in the capacitor through the transistor for a long period of time due to its low off-current.

[0215] Further, the transistor having the above semiconductor layer can hold the charge accumulated in the capacitor through the transistor for a long period of time due to its low off-current. Here, in addition to the transistors provided in the above pixel and drive circuit, it is preferable to apply an oxide semiconductor to semiconductor devices such as transistors used for a touch sensor described later. By applying a transistor to a pixel, it is possible to stop the drive circuit while maintaining the gradation of the image displayed in each display area. As a result, an electronic device with extremely low power consumption can be realized. For stabilizing the characteristics of the transistor and the like, it is preferable to provide an underlying film. As the underlying film, an inorganic insulating film such as a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a silicon nitride oxide film can be used, and it can be formed as a single layer or by lamination. The underlying film can be formed by a sputtering method, a CVD (Chemical Vapor Deposition) method (such as a plasma CVD method, a thermal CVD method, an MOCVD (Metal Organic CVD) method, etc.), an ALD (Atomic Layer Deposition) method, a coating method, a printing method, or the like. Note that the underlying film may not be provided if it is not necessary.

[0216]

[0217] Note that FET623 indicates one of the transistors formed in the drive circuit section 601. The drive circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In the present embodiment, a driver integrated type in which a drive circuit is formed on a substrate is shown, but this is not necessarily required, and the drive circuit can also be formed outside the substrate instead of on the substrate.

[0218] The pixel section 602 is formed of a plurality of pixels including a switching FET611, a current control FET612, and a first electrode 613 electrically connected to the drain thereof, but is not limited thereto, and a pixel section combining three or more FETs and a capacitive element may also be used.

[0219] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive acrylic resin film of a mold.

[0220] In order to improve the coverage of the EL layer and the like to be formed later, the upper end of the insulator 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic resin is used, the radius of curvature ( It is preferable that the insulating material 614 has a curved surface having a thickness of 0.2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0221] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function of It is desirable to use a material with a large capacitance. For example, an ITO film or an indium tin oxide film containing silicon. Indium tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, In addition to single-layer films such as ROM film, tungsten film, Zn film, and Pt film, titanium nitride film and aluminum film are also available. A titanium nitride film and an aluminum-based film are laminated together. In addition, a three-layer structure with a silicon film can be used. The resistance is low, good ohmic contact can be achieved, and the material can also function as an anode. .

[0222] The EL layer 616 is formed by deposition using a deposition mask, inkjet printing, or spin coating. The EL layer 616 is formed by the structure described in the first embodiment. It also contains a certain amount. As other materials constituting the EL layer 616, low molecular compounds or polymer compounds (including oligomers and dendrimers) may also be used.

[0223] Furthermore, the material used for the second electrode 617 that is formed on the EL layer 616 and functions as a cathode is preferably a material with a small work function (such as Al, Mg, Li, Ca, or alloys and compounds of these (MgAg, MgIn, AlLi, etc.)). When the light generated in the EL layer 616 passes through the second electrode 617, it is preferable to use a laminate of a thin metal film with a reduced thickness and a transparent conductive film (such as ITO, indium tin oxide containing 2 - 20 wt% zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), etc.) as the second electrode 617.

[0224] Note that a light - emitting element is formed by the first electrode 613, the EL layer 616, and the second electrode 617. The light - emitting element is the light - emitting element described in Embodiment 2. The pixel portion is formed of a plurality of light - emitting elements. In the light - emitting device of this embodiment, both the light - emitting element described in Embodiment 2 and light - emitting elements having other configurations may be included.

[0225] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, a structure is formed in which the light - emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealing material 605. Note that the space 607 is filled with a filling material. In addition to the case where an inert gas (such as nitrogen or argon) is filled, there is also a case where it is filled with a sealing material. A recess is formed in the sealing substrate, and a drying material is provided therein to suppress deterioration due to the influence of moisture. ​​​​​It can be manufactured and is a preferable configuration.

[0226] Note that it is preferable to use an epoxy resin or glass frit for the sealing material 605. Also these materials are desirably materials that hardly permeate moisture and oxygen. Also, as materials for the sealing substrate 604, in addition to glass substrates and quartz substrates, FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester or plastic substrates made of acrylic resin or the like can be used.

[0227] Although not shown in FIG. 2, a protective film may be provided on the second electrode. The protective film may be formed of an organic resin film or an inorganic insulating film. Also, the protective film may be formed so as to cover the exposed portion of the sealing material 605. Also, the protective film can be provided so as to cover the exposed side surfaces of the surfaces and sides of the pair of substrates, the sealing layer, the insulating layer, etc.

[0228] For the protective film, a material that hardly permeates impurities such as water can be used. Therefore, it is possible to effectively suppress the diffusion of impurities such as water from the outside to the inside.

[0229] As materials constituting the protective film, oxides, nitrides, fluorides, sulfides, ternary compounds, metals or polymers or the like can be used. For example, materials containing aluminum oxide, hafnium oxide, hafnium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide cerium oxide, scandium oxide, erbium oxide, vanadium oxide or indium oxide or the like, and materials containing aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, nitride​​​ including titanium oxide, niobium nitride, molybdenum nitride, zirconium nitride, gallium nitride, etc. materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and sulfides containing strontium, oxides containing erbium and aluminum, yttrium oxides containing lithium and zirconium, etc. can be used.

[0230] The protective film is preferably formed using a film formation method with good step coverage. One such technique is the atomic layer deposition (ALD) method. Materials that can be formed using the ALD method are preferably used for the protective film. By using the ALD method, a dense protective film with reduced defects such as cracks and pinholes or a uniform thickness can be formed. Also, the damage to the processing member during the formation of the protective film can be reduced.

[0231] For example, by forming the protective film using the ALD method, a protective film that is uniform and has few defects can be formed on the surface with a complex uneven shape, the upper surface, side surfaces, and back surface of the touch panel.

[0232] In the above manner, a light-emitting device manufactured using the light-emitting element described in Embodiment 2 can be obtained.

[0233] Since the light-emitting device in this embodiment uses the light-emitting element described in Embodiment 2, a light-emitting device with favorable characteristics can be obtained. Specifically, the light emission described in Embodiment 2 Since the element is a light-emitting element with a long lifespan, a light-emitting device with good reliability can be obtained. Also, since the light-emitting device using the light-emitting element described in Embodiment 2 has good luminous efficiency, it is possible to obtain a light-emitting device with low power consumption.

[0234] Fig. 3 shows an example of a light-emitting device that forms a light-emitting element exhibiting white light emission and is made full-color by providing a coloring layer (color filter) or the like. In Fig. 3(A), there are shown a substrate 1001, an underlying insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, a pixel portion 1040, a driving circuit portion 1041, first electrodes 1024W, 1024R, 1024G, 102 4B of the light-emitting element, a partition 1025, an EL layer 1028, a second electrode 1029 of the light-emitting element, a sealing substrate 103 1, a sealing material 1032, etc. are illustrated.

[0235] Also, in Fig. 3(A), the coloring layers (a red coloring layer 1034R, a green coloring layer 1034G, a blue coloring layer 1034B) are provided on a transparent base material 1033. Further, a black matrix 1 035 may be further provided. The transparent base material 1 033 provided with the coloring layer and the black matrix is aligned and fixed to the substrate 1001. Note that the coloring layer and the black matrix 1035 are covered with an overcoat layer 1036. Also, in Fig. 3(A), there are a light-emitting layer where light does not pass through the coloring layer and exits to the outside, and a light-emitting layer where light passes through the coloring layers of each color and exits to the outside. Since the light that does not pass through the coloring layer is white, and the light that passes through the coloring layer is red, green, or blue, an image can be represented by four-color pixels.

[0236] In FIG. 3(B), an example is shown in which the colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B) are formed between the gate insulating film 1003 and the first interlayer insulating film 1020. Thus, the colored layers may be provided between the substrate 1001 and the sealing substrate 1031.

[0237] In addition, in the light-emitting device described above, the light-emitting device has a structure (bottom emission type) in which light is extracted from the side of the substrate 1001 on which the FET is formed. However, a light-emitting device having a structure (top emission type) in which light is extracted from the side of the sealing substrate 1031 may also be used. A cross-sectional view of the top emission type light-emitting device is shown in FIG. 4. In this case, the substrate 1001 can be a substrate that does not transmit light. Until a connection electrode connecting the FET and the anode of the light-emitting element is fabricated, it is formed in the same manner as the bottom emission type light-emitting device. Thereafter, the third interlayer insulating film 1037 is formed to cover the electrode 1022. This insulating film may serve as a planarization layer. The third interlayer insulating film 1037 can be formed using the same material as the second interlayer insulating film or other known materials.

[0238] The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes here, but they may be cathodes. Further, in the case of a top emission type light-emitting device as shown in FIG. 4, it is preferable that the first electrode is a reflective electrode. The configuration of the EL layer 1028 is the same as the configuration described for the EL layer 103 in Embodiment 1, and the element structure is such that white light emission can be obtained.

[0239] In the top emission structure as shown in FIG. 4, the colored layers (red colored layer 1034R, green colored ​​​​​​​​​​​​​​Sealing is performed using a sealing substrate 1031 provided with color layers (a red color layer 1034R, a green color layer 1034G, and a blue color layer 1034B). A black matrix 1035 may be provided on the sealing substrate 1031 so as to be positioned between pixels. The color layers (the red color layer 1034R, the green color layer 1034G, and the blue color layer 1034B) and the black matrix may be covered with an overcoat layer 1036. Note that a substrate having translucency is used as the sealing substrate 1031. In addition, although an example of full-color display using four colors of red, green, blue, and white has been shown here, it is not particularly limited, and full-color display may be performed using four colors of red, yellow, green, and blue or three colors of red, green, and blue. In a top emission type light-emitting device, application of a microcavity structure can be suitably performed. A light-emitting element having a microcavity structure can be obtained by using a first electrode as a reflective electrode and a second electrode as a semi-transmissive / semi-reflective electrode.

[0240] At least an EL layer is provided between the reflective electrode and the semi-transmissive / semi-reflective electrode, and at least a light-emitting layer serving as a light-emitting region is provided.

[0241] Note that the reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%, and a film having a resistivity of 1×10 -2 Ωcm or less. In addition, the semi-transmissive / semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%,

[0242] and a film having a resistivity of 1×10 -2 Ωcm or less.

[0243] Light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transmissive / semi-reflective electrode and resonates.

[0243] ​By changing the thickness of the transparent conductive film, the above-mentioned composite material, the carrier transport material, etc. of the light-emitting element, the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed. As a result, between the reflective electrode and the semi-transmissive / semi-reflective electrode, light of the resonant wavelength can be enhanced, and light of non-resonant wavelength can be attenuated.

[0244] Note that the light (first reflected light) reflected back by the reflective electrode causes significant interference with the light (first incident light) directly incident on the semi-transmissive · semi-reflective electrode from the light-emitting layer. Therefore, it is preferable to adjust the optical distance between the reflective electrode and the light-emitting layer to (2n - 1)λ / 4 (where n is a natural number of 1 or more, and λ is the wavelength of the amplified emitted light). By adjusting the optical distance, the phases of the first reflected light and the first incident light can be matched to further amplify the light emitted from the light-emitting layer.

[0245] In the above configuration, whether the EL layer has a structure with a plurality of light-emitting layers or a structure with a single light-emitting layer is acceptable. For example, in combination with the configuration of the tandem-type light-emitting element described above, a charge generation layer is sandwiched between a plurality of EL layers in one light-emitting element, and a single or a plurality of light-emitting layers may be formed in each EL layer.

[0246] By having a microcavity structure, it is possible to enhance the forward emission intensity of a specific wavelength, so that power consumption can be reduced. In the case of a light-emitting device that displays an image with four sub-pixels of red, yellow, green, and blue, in addition to the luminance improvement effect due to yellow light emission, a microcavity structure adapted to the wavelength of each color can be applied to all the sub-pixels, resulting in a light-emitting device with good characteristics.

[0247] ​​​​ Since the light-emitting device according to this embodiment uses the light-emitting element described in Embodiment 2, a light-emitting device with good characteristics can be obtained. Specifically, since the light-emitting element described in Embodiment 2 has a long lifespan, a highly reliable light-emitting device can be achieved. Also, since the light-emitting device using the light-emitting element described in Embodiment 2 has good luminous efficiency, it is possible to make a light-emitting device with low power consumption.

[0248] So far, the active matrix type light-emitting device has been described. From here on, the passive matrix type light-emitting device will be described. Fig. 5 shows a passive matrix type light-emitting device fabricated by applying the present invention. Note that Fig. 5(A) is a perspective view showing the light-emitting device, and Fig. 5( B) is a cross-sectional view of Fig. 5(A) cut along the X-Y plane. In Fig. 5, on the substrate 951, an EL layer 955 is provided between the electrode 952 and the electrode 956. The end of the electrode 952 is covered with an insulating layer 953. And a partition layer 954 is provided on the insulating layer 953. The side walls of the partition layer 954 have an inclination such that the gap between one side wall and the other side wall becomes narrower as it approaches the substrate surface. That is, the cross-section of the partition layer 954 in the short side direction is a trapezoidal shape, and the bottom side (oriented in the same direction as the surface direction of the insulating layer 953 and in contact with the insulating layer 953) is shorter than the upper side (oriented in the same direction as the surface direction of the insulating layer 953 and not in contact with the insulating layer 953). ) By providing the partition layer 954 in this way, defects of the light-emitting element caused by static electricity or the like can be prevented. Also, in the passive matrix type light-emitting device as well, the light-emitting element described in Embodiment 2 is used, and a highly reliable light-emitting device or a light-emitting device with low power consumption can be achieved. ​​​​

[0249] As described above, since the light-emitting device can control each of a large number of minute light-emitting elements arranged in a matrix, it is a light-emitting device that can be suitably used as a display device for displaying an image.

[0250] Also, this embodiment can be freely combined with other embodiments.

[0251] (Embodiment 4) In this embodiment, an example in which the light-emitting element described in Embodiment 2 is used as an illumination device will be described with reference to FIG. 6. FIG. 6(B) is a top view of the illumination device, and FIG. 6(A) is an e-f cross-sectional view taken along the line in FIG. 6(B).

[0252] In the illumination device according to this embodiment, a first electrode 401 is formed on a light-transmissive substrate 400 that is a support. The first electrode 401 corresponds to the first electrode 101 in Embodiment 1. When extracting light from the side of the first electrode 401, the first electrode 401 is formed of a material having light-transmittance.

[0253] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400.

[0254] An EL layer 403 is formed on the first electrode 401. The EL layer 403 corresponds to the configuration of the EL layer 103 in Embodiment 1, or the combined configuration of the light-emitting units 511 and 512 and the charge generation layer 513. For these configurations, refer to the relevant description.

[0255] The second electrode 404 is formed to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in Embodiment 1. When extracting light from the side of the first electrode 401, the second ​​​​​​​​​​ The electrode 404 is formed of a material with high reflectivity. The second electrode 404 is connected to the pad 412 to supply voltage.

[0256] As described above, the lighting device shown in this embodiment has a light-emitting element including the first electrode 401, the EL layer 403, and the second electrode 404. Since the light-emitting element has high luminous efficiency, the lighting device in this embodiment can be a lighting device with low power consumption.

[0257] A substrate 400 on which a light-emitting element having the above configuration is formed and a sealing substrate 407 are fixed and sealed using sealing materials 4 05 and 406 to complete the lighting device. Either of the sealing materials 40 5 and 406 may be used. Also, a desiccant can be mixed into the inner sealing material 406 (not shown in FIG. 6(B)), which can adsorb moisture and lead to improved reliability.

[0258] Also, by extending a part of the pad 412 and the first electrode 401 outside the sealing materials 405 and 406, they can be used as external input terminals. Also, an IC chip 420 with a converter or the like mounted thereon may be provided.

[0259] As described above, the lighting device described in this embodiment uses the light-emitting element described in Embodiment 2 for the EL element, and can be a light-emitting device with good reliability. Also, it can be a light-emitting device with low power consumption.

[0260] (Embodiment 5) In this embodiment, an example of an electronic device including the light-emitting element described in Embodiment 2 in a part thereof will be described. The light-emitting element described in the second embodiment has a long life and is a highly reliable light-emitting element. As a result, the electronic device described in this embodiment has a highly reliable light-emitting portion. It may be an electronic device.

[0261] As an example of an electronic device to which the light-emitting element is applied, a television set (television, (also called revision receivers), computer monitors, digital cameras, digital Video cameras, digital photo frames, mobile phones (also called mobile phones or mobile phone devices) ), portable game machines, personal digital assistants, audio playback devices, pachinko machines and other large game machines, etc. Specific examples of these electronic devices are shown below.

[0262] FIG. 7A shows an example of a television device. The television device includes a housing 710. A display unit 7103 is built into the display unit 1. Also, in this embodiment, a stand 7105 is used to support the display unit 1. The display unit 7103 can display images. The display portion 7103 has the light-emitting elements described in Embodiment 2 arranged in a matrix. It is composed.

[0263] The television device can be operated using an operation switch provided on the housing 7101 or a separate remote control. The remote control device 7110 includes an operation key 7109. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the image forming apparatus may be provided.

[0264] The television device has a configuration including a receiver, a modem, etc. The receiver can receive general television broadcasts, and can further connect to a wired or wireless communication network via the modem to perform one-way (sender to receiver) or two-way (between sender and receiver, or between receivers, etc.) information communication.

[0265] Figure 7(B1) shows a computer, which includes a main body 7201, a housing 7202, a display unit 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, etc. This computer is manufactured by arranging the light-emitting elements described in Embodiment 2 in a matrix and using them for the display unit 7203. The computer in Figure 7(B1) may have a form as shown in Figure 7(B2). The computer in Figure 7(B2) has a second display unit 7210 provided instead of the keyboard 720 4 and the pointing device 7206. The second display unit 7210 is a touch panel type, and input can be performed by operating the input display shown on the second display unit 7210 with a finger or a dedicated pen. In addition, the second display unit 7210 can display not only input displays but also other images. The display unit 7203 may also be a touch panel. By connecting the two screens with a hinge, it is possible to prevent problems such as damaging or breaking the screens during storage or transportation. Figure 7(C) shows an example of a mobile terminal. The mobile phone includes, in addition to a display unit 7402

[0266] incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 740 ​​5. It is equipped with a microphone 7406, etc. The mobile phone 7400 has a display unit 7402 manufactured by arranging the light-emitting elements described in Embodiment 2 in a matrix form.

[0267] The mobile terminal shown in Fig. 7(C) can also be configured such that information can be input by touching the display unit 7402 with a finger or the like. In this case, operations such as making a call or creating an email can be performed by touching the display unit 7402 with a finger or the like.

[0268] The screen of the display unit 7402 mainly has three modes. The first is a display mode mainly for displaying images, the second is an input mode mainly for inputting information such as characters, and the third is a display + input mode in which the two modes of the display mode and the input mode are mixed.

[0269] For example, when making a call or creating an email, the display unit 7402 can be set to the character input mode mainly for character input, and an input operation of the characters displayed on the screen can be performed. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402.

[0270] In addition, by providing a detection device having sensors such as a gyro and an acceleration sensor inside the mobile terminal to detect the inclination, the orientation (vertical or horizontal) of the mobile terminal can be determined, and the screen display of the display unit 7402 can be automatically switched.

[0271] In addition, the switching of the screen mode is performed by touching the display unit 7402 or operating the operation button 7403 of the housing 7401. Also, depending on the type of image displayed on the display unit 7402 Therefore, it can also be switched. For example, if the image signal to be displayed on the display unit is video data, it is switched to the display mode, and if it is text data, it is switched to the input mode.

[0272] Also, in the input mode, the signal detected by the optical sensor of the display unit 7402 is detected, and when there is no input by the touch operation of the display unit 7402 for a certain period, the screen mode may be controlled to be switched from the input mode to the display mode.

[0273] The display unit 7402 can also function as an image sensor. For example, by touching the display unit 74 02 with a palm or a finger and imaging the palm print, fingerprint, etc., personal authentication can be performed. Also by using a backlight that emits near-infrared light or a sensing light source that emits near-infrared light on the display unit, finger veins, palm veins, etc. can also be imaged.

[0274] Note that the configuration shown in this embodiment can be used by appropriately combining the configurations shown in Embodiments 1 to 4.

[0275] As described above, the application range of the light-emitting device including the light-emitting element described in Embodiment 2 is extremely wide, and this light-emitting device can be applied to electronic devices in all fields. By using the light-emitting element described in Embodiment 2, a highly reliable electronic device can be obtained.

[0276] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0277] The cleaning robot 5100 has a display 5101 arranged on the upper surface, a plurality of cameras 5102 arranged on the side surface, a brush 5103, and operation buttons 5104. Also, as shown ​​​However, the bottom surface of the cleaning robot 5100 is equipped with tires, suction ports, etc. The cleaning robot 5100 is also equipped with various sensors such as infrared sensors, ultrasonic sensors, acceleration sensors, piezo sensors, optical sensors, and gyro sensors. In addition, the cleaning robot 5 100 is equipped with wireless communication means.

[0278] The cleaning robot 5100 can move autonomously, detect dust 5120, and suck up the dust from the suction port provided on the bottom surface.

[0279] In addition, the cleaning robot 5100 can analyze the images captured by the camera 5102 and determine the presence or absence of obstacles such as walls, furniture, or steps. Also, when an object that is likely to get entangled in the wiring 5103, etc. is detected by image analysis, the rotation of the brush 5103 can be stopped.

[0280] The display 5101 can display the remaining battery level, the amount of dust sucked up, etc. The cleaning robot 5100 can also display the path it has traveled on the display 5101. Also, the display 5101 can be used as a touch panel, and the operation buttons 5104 can be provided on the display 5101.

[0281] The cleaning robot 5100 can communicate with a mobile electronic device 5140 such as a smartphone. The images captured by the camera 5102 can be displayed on the mobile electronic device 5140. Therefore, the owner of the cleaning robot 5100 can know the condition of the room even when away from home. Also, the display on the display 5101 can be confirmed on a mobile electronic device such as a smartphone.

[0282] ​​​​​​​​​​​The light-emitting device according to one aspect of the present invention can be used for the display 5101.

[0283] The robot 2100 shown in FIG. 8(B) includes an arithmetic unit 2110, an illuminance sensor 2101, a microphone lophone 2102, an upper camera 2103, a speaker 2104, a display 2105, a lower part camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.

[0284] The microphone 2102 has a function of detecting the user's voice, ambient sound, etc. Also the speaker 2104 has a function of emitting sound. The robot 2100 can communicate with the user using the microphone 2102 and the speaker 2104. It is possible.

[0285] The display 2105 has a function of displaying various information. The robot 2100 can display the information desired by the user on the display 2105. The display 2105 may be equipped with a touch panel. Also, the display 2105 may be a removable information terminal, and by installing it at a fixed position of the robot 2100, charging and data transfer are possible.

[0286] The upper camera 2103 and the lower camera 2106 have a function of imaging the surroundings of the robot 2100. Also, the obstacle sensor 2107 can detect the presence or absence of obstacles in the traveling direction when the robot 210 0 moves forward. The robot 21 00 can recognize the surrounding environment and move safely using the upper camera 2103, the lower camera 2106, and the obstacle sensor 2107. The light-emitting device according to one aspect of the present invention is It can be used for the display 2105.

[0287] FIG. 8(C) is a diagram showing an example of a goggle-type display. The goggle-type display includes, for example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, operation keys 5005 (including a power switch or an operation switch), connection terminals 5006, a sen sor 5007 (including a function of measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature chemical substance, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient vibration, odor, or infrared rays), a microphone 5008, a display unit 5002, a support unit 5012, earphones 5013, etc. The light-emitting device according to one aspect of the present invention can be used for the display unit 5001 and the second display unit 5002.

[0288] It can be used for the display unit 5001 and the second display unit 5002. It can be used.

[0289] FIG. 9 shows an example in which the light-emitting element described in Embodiment 2 is used in an electric stand which is a lighting device. The electric stand shown in FIG. 9 has a housing 2001 and a light source 2002. As for the light source 2002 The lighting device described in Embodiment 3 may be used.

[0290] FIG. 10 shows an example in which the light-emitting element described in Embodiment 2 is used as an indoor lighting device 3001. Since the light-emitting element described in Embodiment 2 is a highly reliable light-emitting element, a lighting device with good reliability can be obtained. Also, since the light-emitting element described in Embodiment 2 can be made large in area it can be used as a large-area lighting device. Further, since the light-emitting element described in Embodiment 2 is thin it can be used as a thin lighting device.

[0291] The light-emitting element described in Embodiment 2 can also be mounted on the windshield or dashboard of an automobile. FIG. 11 shows an aspect in which the light-emitting element described in Embodiment 2 is used for the windshield or dashboard of an automobile. The display areas 5200 to 5203 are displays provided using the light-emitting element described in Embodiment 2.

[0292] The display area 5200 and the display area 5201 are display devices equipped with the light-emitting element described in Embodiment 2 provided on the windshield of the automobile. The light-emitting element described in Embodiment 2 can be made into a so-called see-through display device in which the opposite side can be seen through by fabricating the first electrode and the second electrode with light-transmissive electrodes. In the case of a see-through display, even if it is installed on the windshield of an automobile, it can be installed without obstructing the view. When providing a transistor or the like for driving, it is preferable to use a light-transmissive transistor such as an organic transistor made of an organic semiconductor material or a transistor using an oxide semiconductor.

[0293] The display area 5202 is a display device equipped with the light-emitting element described in Embodiment 2 provided on the pillar portion. By projecting the video from the imaging means provided on the vehicle body onto the display area 5202, the view blocked by the pillar can be supplemented. Similarly, the display area 5203 provided on the dashboard portion can supplement the view blocked by the vehicle body by projecting the video from the imaging means provided outside the automobile, thereby compensating for the blind spot and enhancing safety. By projecting the video so as to supplement the invisible part, it is possible to perform safety confirmation more naturally without a sense of discomfort.

[0294] The display area 5203 can also provide various other information by displaying navigation information, speedometers, tachometers, travel distances, fuel gauges, gear states, air conditioner settings, etc. The display can appropriately change the display items and layout according to the user's preferences. Note that this information can also be provided in the display areas 5200 to 5202. In addition, the display areas 5200 to 5203 can also be used as lighting devices.

[0295] Also, FIGS. 12(A) and (B) show a foldable portable information terminal 5150. The foldable portable information terminal 5150 has a housing 5151, a display area 5152, and a bending portion 515 3. FIG. 12(A) shows the portable information terminal 5150 in an unfolded state. FIG. 12( B) shows the portable information terminal in a folded state. Despite having a large display area 5152, the portable information terminal 5150 is compact and highly portable when folded.

[0296] The display area 5152 can be folded in half by the bending portion 5153. The bending portion 515 3 is composed of a stretchable member and a plurality of support members. When folding, the stretchable member extends. The bending portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more, and is folded.

[0297] Note that the display area 5152 may be a touch panel (input / output device) that controls a touch sensor (input device). The light-emitting device according to an aspect of the present invention can be used for the display area 5152.

[0298] Also, FIGS. 13(A) to (C) show a foldable portable information terminal 9310. FIG. 13 (A) shows the portable information terminal 9310 in a deployed state. FIG. 13(B) shows the portable information terminal 9310 in a deployed state or in a state changing from one of the deployed or folded states to the other. FIG. 13(C) shows the portable information terminal 9310 in a folded state. The portable information terminal 9310 is excellent in portability in the folded state and has an excellent display listability with a wide display area without seams in the deployed state.

[0299] The display panel 9311 is supported by three housings 9315 connected by a hinge 9313 and is a touch panel (input / output device) equipped with a touch sensor (input device). Further, the display panel 9311 can be reversibly deformed from the deployed state to the folded state of the portable information terminal 9310 by bending between the two housings 9315 through the hinge 9313. The light-emitting device according to one aspect of the present invention can be used for the display panel 9311.

[0300]

Example

[0300] In this example, the synthesis method of N-[4'-(9H-carbazol- 9-yl)-1,1'-biphenyl-4-yl]-N-(1,1'-biphenyl-4-yl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: YG BBiBnf), which is an organic compound according to one aspect of the present invention, will be described in detail. The structural formula of YGBBiBnf is shown below.

[0301]

Chemical formula

[0302] <Step 1: Synthesis of 4'-(9H-carbazol-9-yl)bis(1,1'-biphenyl- 4-yl)amine> 1.6 g (5.0 mmol) of N-(4-bromophenyl) -4-biphenylamine, 1.4 g (5.0 mmol) of 4-(9H-carbazol- 9-yl)benzeneboronic acid, 46 mg (0.15 mmol) of tri(ortho-tolyl )phosphine, 7.5 mL of aqueous potassium carbonate solution (2.0 mmol / L), and 20 mL of toluene and 5 mL of ethanol were placed in a 200 mL three-necked flask. After degassing the mixture under reduced pressure, the inside of the flask was purged with nitrogen . After heating this mixture to 60 °C, 11 mg (50 μmol) of palladium(II) acetate was added, and the mixture was stirred at 80 °C for 7.5 hours. After stirring, the precipitated solid was collected by suction filtration and the obtained solid was washed with toluene, ethanol, and water. The washed solid was extracted with toluene using a Soxhlet extractor, and the obtained solution was concentrated to give 1.5 g of a white solid in a yield of 63%. The synthesis scheme of Step 1 is shown below .

[0303]

Chemical formula

[0304] <Step 2: Synthesis of N-[4'-(9H-carbazol-9-yl)-1,1'-biphenyl -4-yl]-N-(1,1'-biphenyl-4-yl)-6-phenylbenzo[b]naphtho [1,2-d]furan-8-amine (abbreviation: YGBBiBnf)> To a 200 mL three-necked flask, 1.4 g (2.9 mmol) of 4'- (9H-carbazol-9-yl)bis(1,1'-biphenyl-4-yl)amine obtained in Step 1 was added,​ 1.2 g (2.9 mmol) of 8-iodo-6-phenylbenzo[b]naphtho[1,2- d]furan, 0.10 g (0.25 mmol) of 2-dicyclohexylphosphino-2 ’,6’-dimethoxybiphenyl (abbreviation: s-phos), 0.59 g (6.1 mmo l) of sodium tert-butoxide, and 30 mL of xylene were placed. After subjecting this mixture to vacuum degassing, the system was purged with nitrogen. 71 mg (0.12 mmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred at 80 °C for 13 hours. After stirring, the precipitated solid was removed by suction filtration, and the obtained filtrate was filtered through alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 066-05265), and Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-02305). The solid obtained by concentrating the obtained filtrate was recrystallized from toluene to obtain 1.5 g of a white solid in a yield of 65%. The synthesis scheme for Step 2 is shown below.

[0305]

[0306]

Chemical formula

[0307] The 1 1H NMR data of the obtained solid are shown in Figure 14, and the numerical data are shown below. From this, it was found that N-[4’-(9H-carbazol-9-yl)-1,1’-biphenyl-4-yl]- N-(1,1’-biphenyl-4-yl)-6-phenylbenzo[b]naphtho[1,2- d]furan-8-amine (abbreviation: YGBBiBnf) was obtained.

[0307] 1 1H NMR (dichloromethane-d2, 500 MHz): δ = 7.18 - 7.23 (m, 3H),7.25-7.29(m,6H),7.31(t,J=7.5Hz,1H),7 .37(d,J=8.0Hz,1H),7.40-7.52(m,9H),7.58-7 .64(m,7H),7.68(d,J=8.5Hz,2H),7.75(td,J1= 7.5Hz,J2=1.0Hz,1H),7.85(d,J=8.5Hz,2H),8. 04(s,1H),8.08(d,J=8.0Hz,1H),8.14(d,J=7.5 Hz,2H)8.28(dd,J1=8.0Hz,J2=1Hz,1H),8.69(d ,J=8.0Hz,1H)

[0308] The obtained solid was purified by sublimation. The sublimation purification was carried out under an argon flow rate of 10 mL / min and a pressure of The solid was heated to 340 to 350°C under 2.2 Pa. After purification by sublimation, The compound was obtained as a pale yellow solid in a yield of 1.2 g and a recovery rate of 84%.

[0309] Next, the absorption and emission spectra of a toluene solution of YGBBiBnf were measured. The results are shown in Figure 15. The absorption spectrum and emission spectrum of the thin film are shown in Figure 16. The solid thin film was prepared on a quartz substrate by vacuum deposition. The measurement was performed using an ultraviolet-visible spectrophotometer (V550 model, manufactured by JASCO Corporation) and only toluene was measured. The absorption spectrum of the thin film was also subtracted from that of the quartz cell. A spectrophotometer (Hitachi High-Technologies Corporation, Spectrophotometer U4100) was used for the measurement. The emission spectrum was measured using a fluorometer (FS92 manufactured by Hamamatsu Photonics, Ltd.). 0) was used.

[0310] As shown in Figure 15, the toluene solution of YGBBiBnf shows an absorption peak at around 344 nm. The peak of the emission wavelength was 421 nm (excitation wavelength 344 nm). Also, from Fig. 16, Y The thin film of GBBiBnf has absorption peaks around 347 nm, 330 nm, 298 nm, and 252 nm, and the peak of the emission wavelength is around 430 nm and 449 nm (excitation wavelength 360 nm) was observed. From these results, it was confirmed that YGBBiBnf emits blue light, and it was found that it can also be used as a host for luminescent materials and fluorescent materials in the visible region.

[0311] Also, the thin film of YGBBiBnf was found to be less likely to aggregate even in air, with little change in morphology and good film quality.

[0312] Subsequently, the results of calculating the HOMO level and LUMO level of YGBBiBnf based on cyclic voltammetry (CV) measurements are shown. The calculation method is shown below.

[0313] As the measuring device, an electrochemical analyzer (manufactured by BAS Inc., model number: ALS model 600A or 600C) was used. The solution for CV measurement used dehydrated dimethyl formamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 227 05-6) as the solvent, and tetra-n-butylammonium perchlorate (n-B u4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) was dissolved to a concentration of 100 mmol / L, and the measurement target was further dissolved to a concentration of 2 mmol / L to prepare. As the working electrode, a platinum electrode (manufactured by BAS Inc., PT E platinum electrode) was used, as the auxiliary electrode, a platinum electrode (manufactured by BAS Inc., VC-3 used P t counter electrode (5 cm)) was used, and as the reference electrode, an Ag / Ag+ electrode (manufactured by BAS Inc.,​​ Manufactured by Sumitomo Chemical Co., Ltd., RE7 non-aqueous solvent-based reference electrode) was used respectively. The measurement was carried out at room temperature (20~ 25°C). Also, the scan rate during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and reduction potential Ec [V] with respect to the reference electrode were measured. Ea was taken as the intermediate potential of the oxidation-reduction wave, and Ec was taken as the intermediate potential of the reduction-oxidation wave. Here, the potential energy with respect to the vacuum level of the reference electrode used in this example is -4.94 [eV]. Since this is known, the HOMO level [eV] = -4.94 - Ea and the LUMO level [eV = -4.94 - Ec, and the HOMO level and LUMO level can be obtained respectively from these formulas.

[0314] The CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th cycle measurement was compared with the oxidation-reduction wave in the 1st cycle to examine the electrical stability of the compound.

[0315] As a result, it was found that the HOMO level of YGBBiBnf is -5.56 eV and the LUMO level is -2.5 1 eV. From this measurement result, it became clear that YGBBiBnf is an organic compound with a relatively deep HOMO level. Therefore, even when an organic compound with a deep HOMO level is used as the host material of the light-emitting layer, good hole injection properties into the host material can be exhibited. Also, when comparing the waveforms in the 1st cycle and after 100 cycles in the repeated measurement of the oxidation-reduction wave, 81% of the peak intensity was maintained in the measurement of the oxidation potential Ea [V], and 95% of the peak intensity was maintained in the reduction potential Ec [eV]. From this, it was confirmed that YGBBiBnf has very good resistance to oxidation and reduction.

[0316] ​​​​​​​​​In addition, differential scanning calorimetry (DSC) of YGBBiBnf was performed using a Pyris 1 DSC manufactured by PerkinElmer, Inc. The differential scanning calorimetry was carried out at a heating rate of 40 °C / min from -10 °C to 320 °C, then held at the same temperature for 3 minutes, and then cooled to -10 °C at a cooling rate of 100 °C / min and held at -10 °C for 3 minutes. This operation was continuously performed twice. From the DSC measurement results of the second cycle, it was revealed that the glass transition point of YGBBiBnf is 159 °C, indicating that it is a substance with very high heat resistance.

[0317] Furthermore, thermogravimetry - differential thermal analysis (TG - DTA) of YGBBiBnf was performed. For the measurement, a high - vacuum differential thermogravimetric balance (TG - DTA2410SA manufactured by Bruker AXS K.K.) was used. The measurement was carried out at atmospheric pressure under the conditions of a heating rate of 10 °C / min and a nitrogen gas flow (flow rate: 200 mL / min). In the thermogravimetry - differential thermal analysis of YGBBiBnf, it was found that the temperature at which the weight determined from the thermogravimetry measurement becomes -5% of the initial weight (decomposition temperature) is 500 °C or higher, indicating that it is a substance with high heat resistance.

Example

[0318] In this example, N - [4'' - (9H - carbazol - 9 - yl)1,1':4',1'' - terphenyl - 4 - yl] - N - (1,1' - biphenyl - 4 - yl) - 6 - phenylbenzo[b]naphtho[1,2 - d]furan - 8 - amine, an organic compound of one aspect of the present invention, was used. The synthesis method of Min (abbreviation: YGTBiBnf) will be described in detail. YGTBiBnf The structural formula of is shown below.

[0319]

Chemical formula

[0320] <Step 1: Synthesis of N-(1,1'-biphenyl-4-yl)-4''-(9H-carbazol-9-yl)(1,1';4',1''-terphenyl-4-yl)amine> > Into a 200 mL three-necked flask, add 1.6 g (5.0 mmol) of N-(4-bromophenyl) -4-biphenylamine, 1.8 g (5.0 mmol) of 4'-(9H-carbazol-9-yl)-1,1'-biphenyl-4-boronic acid, 46 mg (0.15 mmol) of tri(ortho-tolyl)phosphine, 7.5 mL of aqueous potassium carbonate solution (2.0 mmol / L), 40 mL of toluene, and 10 mL of ethanol. After degassing this mixture under reduced pressure , the inside of the flask was purged with nitrogen. After heating this mixture to 60 °C, 12 mg (5 0 μmol) of palladium(II) acetate was added, and this mixture was stirred at 80 °C for 12 hours . After stirring, the precipitated solid was collected by suction filtration, and the obtained solid was washed with toluene, ethanol, and water . The washed solid was washed with toluene using a Soxhlet extractor, and thus, 1.8 g of the target light gray solid was obtained with a yield of 63%. The synthesis scheme of Step 1 is shown as follows . as follows.

[0321]

Chemical formula

[0322] <Step 2: Synthesis of N-[4’’-(9H-carbazol-9-yl)-1,1’:4’,1’ ’-terphenyl-4-yl]-N-(1,1’-biphenyl-4-yl)-6-phenyl benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: YGTBiBnf) > Into a 200 mL three-necked flask, add 1.8 g (3.2 mmol) of N-( 1,1’-biphenyl-4-yl)-4’’-(9H-carbazol-9-yl)(1, (1’,1’’;4’,1’’’-terphenyl-4-yl)amine obtained in Step 1, 1.3 g (3.2 mmol) of 8-iodo-6-phenylbenzo[b]naphtho[1,2-d]furan, 0.13 g ( 0.32 mmol) of 2-dicyclohexylphosphine-2’,6’-dimethoxybiphe nyl (abbreviation: s-phos), 0.62 g (6.4 mmol) of sodium tert butoxide, and 32 mL of xylene. After degassing this mixture under reduced pressure, the inside of the flask was purged with nitrogen. To this mixture, add 92 mg (0.16 mmol) of palladium(II) acetate and stir this mixture at 80 °C for 3 hours. After stirring, when the reaction was confirmed by thin-layer chromatography it was confirmed that raw materials remained. To this mixture, add 67 mg (0 .16 mmol) of s-phos and 90 mg (0.16 mmol) of palladium (II) acetate, and heat and stir at 100 °C for an additional 13 hours. Remove the precipitated solid by suction filtration and filter the resulting filtrate through alumina, Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 0 66-05265), and Celite (Wako Pure Chemical Industries, Ltd., catalog number: 537-023 05). Concentrate the resulting filtrate. The solid obtained after concentration can be dissolved in any solvent Purified by silica gel chromatography using [relevant substance], 1.5 g of the solid of the target product was obtained. The synthesis scheme of Step 2 is shown below.

[0323]

Chemical formula

[0324] The 1 1H NMR data of the obtained solid are shown in Figure 17, and the numerical data are shown below. From this, N-[4''-(9H-carbazol-9-yl)-1,1':4',1''-terphenyl -4-yl]-N-(1,1'-biphenyl-4-yl)-6-phenylbenzo[b] naphtho[1,2-d]furan-8-amine (abbreviation: YGTBiBnf) was obtained. It was found.

[0325] 1 1H NMR (dichloromethane-d2, 500 MHz): δ = 7.16 - 7.23 (m, 3H), 7.25 - 7.33 (m, 7H), 7.35 (d, J = 8.0 Hz, 1H), 7 .42 (tt, J1 = 7.0, J2 = 1.0 Hz, 4H), 7.46 - 7.51 (m, 5 H), 7.57 - 7.63 (m, 5H), 7.66 (d, J = 8.5 Hz, 4H), 7. 74 - 7.80 (m, 5H), 7.90 (d, J = 8.5 Hz, 2H), 8.03 (s, 1H), 8.08 (d, J = 8.0 Hz, 1H), 8.15 (d, J = 8.0 Hz, 2H ), 8.28 (dd, J1 = 8.5 Hz, J2 = 1.5 Hz, 1H), 8.69 (d, J = 8.0 Hz, 1H)

[0326] The obtained 1.5 g of solid was subjected to sublimation purification. The sublimation purification was carried out at a pressure of 1.8×10 -2 Pa Under these conditions, the solid was heated to 370 °C. After sublimation purification, a pale yellow solid of the target compound was collected in an amount of 1.0 g with a recovery rate of 69%.

[0327] Next, the absorption spectrum and emission spectrum of the toluene solution of YGTBiBnf were measured and the results are shown in FIGS. 18 and 19. The measurement was carried out in the same manner as in Example 1.

[0328] From FIG. 18, the toluene solution of YGTBiBnf showed an absorption peak around 345 nm, and the peak of the emission wavelength was 416 nm (excitation wavelength 345 nm). Also, from FIG. 19, the thin film of Y GTBiBnf showed absorption peaks around 368 nm, 348 nm, 325 nm, 297 nm, and 257 nm and the peaks of the emission wavelengths were around 430 nm and 448 nm (excitation wavelength 360 nm). From these results, it was confirmed that YGTBiBnf emits blue light and it was found that it can also be used as a host for luminescent materials and fluorescent luminescent materials in the visible region.

[0329] Also, the thin film of YGTBiBnf was found to be difficult to aggregate even in air, with little change in morphology and good film quality.

[0330] Subsequently, the results of calculating the HOMO level and LUMO level of YGTBiBnf based on cyclic voltammetry (CV) measurement are shown. The calculation method is the same as in Example 1.

[0331] As a result, it was found that the HOMO level of YGTBiBnf was -5.55 eV and the LUMO level was -2.5 1 eV. From this measurement result, it became clear that YGTBiBnf is an organic compound with a relatively deep HOMO level. Therefore, as a host material for the light-emitting layer it is clear that YGTBiBnf is an organic compound with a relatively deep HOMO level. Therefore, as a host material for the light-emitting layer Even when an organic compound with a deep HOMO level is used, good hole injection properties into the host material of the light-emitting layer can be exhibited. Moreover, in the repeated measurement of the oxidation-reduction wave, when compared with the waveform after the first cycle and 1 00 cycles, in the measurement of the oxidation potential Ea [V], 81% of the peak intensity was maintained, and in the reduction potential Ec [eV], 93% of the peak intensity was maintained. From this, it was confirmed that Y GTBiBnf has very good resistance to oxidation and reduction.

[0332] In addition, DSC measurement of YGTBiBnf was performed. The DSC measurement was carried out in the same manner as in Example 1 . From the DSC measurement results of the second cycle, it became clear that the glass transition point of YGTBiBnf is 167 °C , indicating that it is a substance with very high heat resistance.

[0333] In addition, TG-DTA of YGTBiBnf was performed. The measurement was carried out in the same manner as in Example 1. From this , it was found that for YGTBiBnf, the temperature at which the weight obtained from the thermogravimetric measurement becomes -5% of that at the start of the measurement (decomposition temperature) is 500 °C or higher, indicating that it is a substance with high heat resistance.

Example

[0334] In this example, the synthesis method of N-(1,1'-biphenyl-4-yl)-6 -phenyl-N-[4-(9-phenylcarbazol-3-yl)phenyl]benzo[b naphtho[d]furan-8-amine (abbreviation: PCBBiBnf), which is an organic compound of the present invention, will be described in detail. The structural formula of PCBBiBnf is shown below.

[0335]

Chemical formula

[0336] <Step 1: Synthesis of N-(1,1'-biphenyl-4-yl)-6-phenyl-N-[4-( 9-phenylcarbazol-3-yl)phenyl]benzo[b]naphtho[d]furan-8 -amine (abbreviation: PCBBiBnf)> 13 g (30 mmol) of 8-iodo-6-phenylbenzo[b]naphtho[1,2-d] furan, 15 g (32 mmol) of 4-(9-phenyl-9H-carbazol-3-yl )-4'-phenyldiphenylamine, 7.8 g (0.14 mol) of potassium hydroxide and 2.4 g (1.2 mmol) of tri(t-butyl)phosphine 10 wt% toluene solution, 210 mL of toluene, and 0.17 g (0.30 mmol) of bis(dibenzylidene acetone)palladium(II) were placed in a 500 mL four-necked flask equipped with a reflux condenser , and the system was purged with nitrogen. The mixture was stirred at 110 °C for 29 hours. Toluene was added to the mixture to dissolve the solid, and the resulting organic layer was washed with water. Activated carbon was added to the resulting organic layer, and the mixture was filtered by suction. The resulting filtrate was concentrated to obtain a brown solid. The obtained solid was dissolved in toluene , and isopropyl alcohol was added dropwise to obtain a pale yellow solid. The solid was dissolved in toluene , and isopropyl alcohol was added dropwise to obtain crystals. As a result, 20 g of pale yellow crystals of the target product were obtained in a yield of 86%. The synthesis scheme of Step 1 is shown below.

[0337]

Chemical formula

[0338] The 1 1H NMR data of the obtained solid are shown in Figure 20, and the numerical data are shown below. From this, N -(1,1'-Biphenyl-4-yl)-6-phenyl-N-[4-(9-phenylcarb azol-3-yl)phenyl]benzo[b]naphtho[d]furan-8-amine (abbreviation: PCBBiBnf) was found to be obtained. The 1 measurement results of 1H NMR are shown below.

[0339] 1 1H NMR (dichloromethane-d2, 500 MHz): δ = 7.15 - 7.19 (m, 3H), 7.25 (d, J = 8.5 Hz, 2H) 7.26 - 7.29 (m, 3H), 7. 31 (dt, J1 = 7.5 Hz, J2 = 1 Hz, 1H), 7.35 (dd, J1 = 8.0 Hz, J2 = 1 Hz, 1H), 7.39 - 7.50 (m, 9H), 7.57 - 7.64 ( m, 9H), 7.69 (dd, J1 = 8.0 Hz, J2 = 1.5 Hz, 1H), 7.70 (d, J = 8.5 Hz, 2H), 7.76 (td, J1 = 7.0 Hz, J2 = 1.5 Hz , 1H), 8.02 (s, 1H), 8.07 (d, J = 8.5 Hz, 1H), 8.17 ( d, J = 7.5 Hz, 1H), 8.26 (dd, J1 = 8.0 Hz, J2 = 1.5 Hz, 1H), 8.38 (sd, J = 1.0 Hz, 1H), 8.69 (d, J = 8.0 Hz, 1 H)

[0340] The obtained 17 g of solid was subjected to sublimation purification. The sublimation purification was carried out by heating the solid at a pressure of 2.0 Pa and 300 °C for 1 hour and 10 minutes, and then heating the solid at 360 °C for 2 hours and 40 minutes. After sublimation purification, 15.5 g of the target light yellow solid was obtained with a recovery rate of 91%.

[0341] Next, the absorption spectrum and emission spectrum of a toluene solution of PCBBiBnf were measured, and the results are shown in FIGS. 21 and 22. The measurement was carried out in the same manner as in Example 1.

[0342] As shown in FIG. 21, the toluene solution of PCBBiBnf has an absorption peak near 341 nm, and the peak of the emission wavelength was 432 nm (excitation wavelength 341 nm). Also, from FIG. 22, P the thin film of CBBiBnf has absorption peaks near 376 nm, 336 nm, 272 nm, and 254 nm, and the peaks of the emission wavelengths are near 430 nm and 449 nm (excitation wavelength 360 nm). From these results, it was confirmed that PCBBiBnf emits blue light, and it was found that it can also be used as a host for light-emitting materials and fluorescent light-emitting materials in the visible region.

[0343] Also, the thin film of PCBBiBnf was found to be less likely to aggregate even in air, with little change in morphology and good film quality.

[0344] Subsequently, the results of calculating the HOMO level and LUMO level of PCBBiBnf based on cyclic voltammetry (CV) measurements are shown. The calculation method is the same as in Example 1. The results of the calculation are shown. The calculation method is the same as in Example 1.

[0345] As a result, it was found that the HOMO level of PCBBiBnf is -5.47 eV and the LUMO level is -2.5 0 eV. From these measurement results, it became clear that PCBBiBnf is an organic compound with a relatively deep HOMO level. Therefore, when an organic compound with a deep HOMO level is used as the host material of the light-emitting layer, good hole injection properties into the host material can also be exhibited. Also, when comparing the waveforms of the first cycle and after 100 cycles in the repeated measurement of the oxidation-reduction wave, 90% of the peak intensity was maintained in the measurement of the oxidation potential Ea [V], and 94% of the peak intensity was maintained at the reduction potential Ec [eV]. Therefore, PCBBiBnf has good stability in the oxidation-reduction cycle. potential Ec [eV], it was found that 94% of the peak intensity was maintained. From this, PCBBiBnf has good stability in the oxidation-reduction cycle. It was confirmed that it has very good resistance to oxidation and reduction.

[0346] In addition, DSC measurement of PCBBiBnf was performed. The DSC measurement was carried out in the same manner as in Example 1. From the DSC measurement results of the second cycle, the glass transition point of PCBBiBnf was found to be 153 °C, indicating that it is a substance with very high heat resistance.

[0347] In addition, TG-DTA of PCBBiBnf was performed. The measurement was carried out in the same manner as in Example 1. From this, it was found that the temperature at which the weight obtained from the thermogravimetric measurement becomes -5% of that at the start of the measurement (decomposition temperature) of PCBBiBnf is 492 °C, indicating that it is a substance with high heat resistance.

Example

[0348] In this example, the light-emitting element 1 and the light-emitting element 2 of one aspect of the present invention described in Embodiment 2 will be described. The structural formulas of the organic compounds used in the light-emitting element 1 and the light-emitting element 2 are shown below.

[0349]

Chemical formula

[0350] (Method for manufacturing the light-emitting element 1) First, indium tin oxide (ITSO) containing silicon oxide was formed into a film on a glass substrate by sputtering to form the first electrode 101. The film thickness was 70 nm, and the electrode area was 2 mm × 2 mm.

[0351] Next, as a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200 °C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

[0352] Subsequently, the substrate was introduced into a vacuum deposition apparatus whose interior had been evacuated to about 10 -4 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0353] Next, with the surface on which the first electrode 101 was formed facing downward, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in the vacuum deposition apparatus. On the first electrode 101, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN) represented by the above structural formula (i) was deposited to a thickness of 5 nm by a deposition method using resistance heating to form a hole injection layer 111.

[0354] Next, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) represented by the above structural formula (ii) was deposited on the hole injection layer 111 to a film thickness of 20 nm to form a first hole transport layer 112-1. On the first hole transport layer 112-1, N-[4'-(9H-carbazol-9-yl)-1,1'-biphenyl-4-yl]-N-(1,1'-biphenyl-4-yl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: YGBBiBnf) represented by the above structural formula (iii) was deposited to a film thickness of 10 nm to form a second hole transport layer 112-2.

[0355] Subsequently, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenyl) Nilbenzo[b]naphtho[1,2-d]furan)-8-amine (abbreviation: 1,6BnfA Prn-03) and were co-evaporated at a weight ratio of 1:0.03 (= cgDBCzPA:1,6BnfAPrn -03) to form the light-emitting layer 113 with a thickness of 25 nm.

[0356] Thereafter, on the light-emitting layer 113, 2-[3'-(dibenzothio phen-4-yl)biphenyl-3-yl]dibenz[f,h]quinoxaline (abbreviation: 2 mDBTBPDBq-II) was evaporated to a thickness of 15 nm, and then the above structural formula (vi i) represented 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10 -phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0357] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby fabricating the light-emitting device 1 of this example.

[0358] (Fabrication method of the light-emitting device 2) The light-emitting device 2 used YGBBiBnf in the second hole transport layer 112-2, and the above structural formula (v iii) represented N-[4''-(9H-carbazol-9-yl)1,1':4', 1''-terphenyl-4-yl]-N-(1,1'-biphenyl-4-yl)-6-f enylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: YGTBiBnf ) was fabricated in the same manner as the light-emitting device 1 except for the change.

[0359] (Fabrication method of the comparative light-emitting device 1) The comparative light-emitting element 1 was fabricated in the same manner as the light-emitting element 1, except that YGBBiBnf used in the second hole transport layer 112-2 was replaced with 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine (abbreviation: YGTBi1BP) represented by the formula (ix). 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl-4-yl]triphenylamine represented by the formula (ix) was changed to otherwise fabricated in the same manner as the light-emitting element 1.

[0360] The element structures of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1 are summarized in the following table.

[0361]

Table 1

[0362] After the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 1 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting elements were not exposed to the atmosphere (a sealing material was applied around the elements, and UV treatment and heat treatment were performed at 80 °C for 1 hour during sealing), the initial characteristics and reliability of these light-emitting elements were measured. The measurements were performed at room temperature. The luminance-current density characteristics, current efficiency-luminance characteristics, luminance-voltage characteristics, current-voltage characteristics, external quantum efficiency-luminance characteristics, and emission spectra of the light-emitting element 1, the light-emitting element 2, and the comparative light-emitting element 2 are shown in FIGS. 23, 24, 25, 26, 27, and 28, respectively. Also, the main characteristics of each light-emitting element near 1000 cd / m² are shown in Table 2.

[0363] 000 cd / m 2

[0364]

Table 2

[0365] ​​​​​​From FIGS. 23 to 28 and Table 2, it was found that the light-emitting elements 1 and 2, which are one aspect of the present invention, are blue light-emitting elements having good characteristics such as driving voltage and luminous efficiency.

[0366] Also, a graph showing the change in luminance with respect to the driving time at a current density of 50 mA / cm 2 is shown in FIG. 29. As shown in FIG. 29, the light-emitting elements 1 and 2, which are light-emitting elements of one aspect of the present invention, have a smaller decrease in luminance with the accumulation of driving time than the comparative light-emitting element 1, and use an organic compound of one aspect of the present invention in which the biphenyl group substituted with an amine is a benzonaphthofuranyl group. It was found that a light-emitting element with good lifetime was obtained.

Example

[0367] In this example, the light-emitting elements 3 and 4 of one aspect of the present invention described in Embodiment 2 will be described. The structural formulas of the organic compounds used in the light-emitting elements 3 and 4 are shown below.

[0368]

Chemical formula

[0369] (Method for manufacturing the light-emitting element 3) First, indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by sputtering to form the first electrode 101. The film thickness was 70 nm, and the electrode area was 2 mm × 2 mm.

[0370] Next, as a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water, baked at 200 °C for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

[0371] Thereafter, 10-4 The substrate was introduced into a vacuum evaporation apparatus whose interior was depressurized to the Pa level, and vacuum evaporation was performed in the heating chamber within the evaporation apparatus at 170 °C for 30 minutes. After that, the substrate was allowed to cool for about 30 minutes .

[0372] Next, with the surface on which the first electrode 101 was formed facing downward, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided within the vacuum evaporation apparatus. Onto the first electrode 101, by means of a vapor deposition method using resistance heating, 2,3,6,7,10,11 -hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT -CN) was vapor deposited to a thickness of 5 nm to form the hole injection layer 111.

[0373] Next, onto the hole injection layer 111, 4,4’-bis[N-(1 -naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) represented by the above structural formula (ii) was vapor deposited to a film thickness of 20 nm to form the first hole transport layer 112-1. Onto the first hole transport layer 112-1 N-[4’-(9H-carbazol-9-yl)-1 ,1’-biphenyl-4-yl]-N-(1,1’-biphenyl-4-yl)-6-phenyl benzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: YGBBiBnf) represented by the above structural formula (iii) was vapor deposited to a film thickness of 10 nm to form the second hole transport layer 112-2.

[0374] Subsequently, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) and the above N,N’-(pyrene-1,6-diyl)bis[(6,N-diphenyl Nilbenzo[b]naphtho[1,2-d]furan)-8-amine (abbreviation: 1,6BnfA Prn-03) and were co-evaporated at a weight ratio of 1:0.03 (= cgDBCzPA:1,6BnfAPrn -03) to form the light-emitting layer 113 with a thickness of 25 nm.

[0375] Thereafter, on the light-emitting layer 113, 2-[3'-(dibenzothio phen-4-yl)biphenyl-3-yl]dibenz[f,h]quinoxaline (abbreviation: 2 mDBTBPDBq-II) was evaporated to a thickness of 15 nm, and then the above structural formula (vi i) represented 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10 -phenanthroline (abbreviation: NBPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0376] After forming the electron transport layer 114, lithium fluoride (LiF) was evaporated to a thickness of 1 nm to form the electron injection layer 115, and then aluminum was evaporated to a thickness of 200 nm to form the second electrode 102, thereby fabricating the light-emitting device 1 of this example.

[0377] (Fabrication method of the light-emitting device 4) The light-emitting device 4 was fabricated in the same manner as the light-emitting device 3, except that YGBBiBnf used in the second hole transport layer 112-2 was changed to N-[4''-(9H-carbazol-9-yl)1,1':4', 1''-terphenyl-4-yl]-N-(1,1'-biphenyl-4-yl)-6-f enylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation: YGTBiBnf ). )

[0378] (Fabrication method of the comparative light-emitting device 2) The comparative light-emitting element 2 is the same as the light-emitting element 3 except that YGBBiBnf used in the second hole transport layer 112-2 is changed to N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho [1,2-d]furan-8-amine (abbreviation: BBABnf) represented by formula (x). It was fabricated in the same manner as the light-emitting element 3.

[0379] The device structures of the light-emitting element 3, the light-emitting element 4, and the comparative light-emitting element 2 are summarized in the following table.

[0380]

Table 3

[0381] The light-emitting element 3, the light-emitting element 4, and the comparative light-emitting element 2 were placed in a glove box under a nitrogen atmosphere and sealed with a glass substrate so that the light-emitting elements were not exposed to the air (a sealing material was applied around the elements, and UV treatment and heat treatment were performed at 80 °C for 1 hour during sealing). After that, the initial characteristics of these light-emitting elements were measured. The measurements were performed at room temperature. The luminance-current density characteristics of the light-emitting element 3, the light-emitting element 4, and the comparative light-emitting element 2 are shown in FIG. 30, the current efficiency-luminance characteristics are shown in FIG. 31, the luminance-voltage characteristics are shown in FIG. 32, the current-voltage characteristics are shown in FIG. 33, the external quantum efficiency-luminance characteristics are shown in FIG. 34, and the emission spectrum is shown in FIG. 35. In addition, the main characteristics of each light-emitting element around 1000 cd / m

[0382] are shown in Table 4. 2

[0383]

Table 4

[0384] From FIGS. 30 to 35 and Table 4, the light-emitting element 3 and the light-emitting element 4, which are one aspect of the present invention, ​​​​​​​It was found that it is a blue light-emitting element with good characteristics such as driving voltage and luminous efficiency. The amine skeleton not only has a benzonaphthofuranyl group, but also an organic compound in which a carbazolyl group is substituted is used as a hole transport material to improve carrier balance and enable the production of a highly efficient element was found.

Example

[0385] In this example, the light-emitting element 5 of one aspect of the present invention and the comparative light-emitting element 3 will be described. The structural formulas of the organic compounds used in the light-emitting element 5 and the comparative light-emitting element 3 are shown below.

[0386]

Chemical formula

[0387] (Method for manufacturing the light-emitting element 5) First, indium tin oxide (ITSO) containing silicon oxide was formed on a glass substrate by sputtering to form the first electrode 101. The film thickness was 70 nm, and the electrode area was 2 mm × 2 mm.

[0388] Next, as a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water and baked at 200 °C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

[0389] After that, the substrate was introduced into a vacuum deposition apparatus whose internal pressure was reduced to about 10 -4 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum deposition apparatus, and then the substrate was allowed to cool for about 30 minutes and cooled.

[0390] Next, with the surface on which the first electrode 101 is formed facing downward, the first electrode 101 is formed The obtained substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and on the first electrode 101, N-(1,1'-biphenyl-4-yl)-6-phenyl-N-[4-(9-phenylcarbazol-3-yl)phenyl]benzo[b]naphtho[d]furan-8-amine (abbreviation: PCBBiBnf) represented by the above structural formula (xi) and NDP-9 (Analytical Laboratory Co., Ltd., material serial number: 1S20170124) were co-evaporated at a weight ratio of 1:0.1 (= PCBBiBnf: NDP-9) to form a hole injection layer 111 with a thickness of 10 nm.

[0391] Next, on the hole injection layer 111, PCBBiBnf was evaporated to a thickness of 20 nm as the first hole transport layer 112-1, and then N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-aminop-terphenyl (abbreviation: DBfBB1TP) represented by the above structural formula (xii) was evaporated to a thickness of 10 nm as the second hole transport layer 112-2 to form a hole transport layer 112.

[0392] Subsequently, 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03) represented by the above structural formula (v) were co-evaporated at a weight ratio of 1:0.03 (= cgDBCzPA: 1,6BnfAPrn-03) to form a light-emitting layer 113 with a thickness of 25 nm.

[0393] ​​​​​​​​​​​​​Subsequently, on the light-emitting layer 113, 2-[3’-(9,9- dimethyl-9H-fluoren-2-yl)-1,1’-biphenyl-3-yl]-4,6 -diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) was deposited to a film thickness of 10 nm. After that, 2-{4-[9,10-di(naphthalen-2-yl)-2-anthryl]phenyl}-1 -phenyl-1H-benzimidazole (abbreviation: ZADN) represented by the above structural formula (xiv) and 8-hydroxyquinolinolato-lithium (abbreviation: Liq) represented by the above structural formula (xv) were co-deposited at a weight ratio of 1:1 (=Z ADN:Liq) to a thickness of 15 nm to form the electron transport layer 114. After forming the electron transport layer 114, Liq was deposited to a film thickness of 1 nm to form the electron injection layer 1

[0394] 15, and then aluminum was deposited to a film thickness of 200 nm to form the second electrode 102, thereby fabricating the light-emitting device 3 of this example.

[0395] (Fabrication method of Comparative Light-Emitting Device 3) Comparative Light-Emitting Device 3 was fabricated in the same manner as Light-Emitting Device 5, except that PCBBiBnf in Light-Emitting Device 5 was replaced with N-(1,1’-biphenyl-4-yl)-9,9-dimethyl-N-[4-(9- enyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine ( abbreviation: PCBBiF) represented by the above structural formula (xvi).

[0396] The device structures of Light-Emitting Device 5 and Comparative Light-Emitting Device 3 are summarized in the following table.

[0397]

Table 5

[0398] The light-emitting element 5 and the comparative light-emitting element 3 were placed in a glove box with a nitrogen atmosphere. The process of sealing the element with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is applied around the element). After the encapsulation, UV treatment and heat treatment at 80°C for 1 hour were performed, The characteristics and reliability were measured at room temperature.

[0399] FIG. 36 shows the luminance vs. current density characteristics of the light-emitting element 5 and the comparative light-emitting element 3, and FIG. 37 shows the current efficiency vs. luminance characteristics of the light-emitting element 5 and the comparative light-emitting element 3. The luminance-voltage characteristics are shown in Fig. 37, the current-voltage characteristics are shown in Fig. 39, and the external quantum efficiency-luminance characteristics are shown in Fig. 40. The luminance characteristics are shown in FIG. 40 and the emission spectrum is shown in FIG. 41. m 2 The main characteristics of the area are shown in Table 6.

[0400] [Table 6]

[0401] 36 to 41 and Table 6, the light-emitting element 5 of one embodiment of the present invention is similar to the comparative light-emitting element 3. It was found that the blue light emitting device had the same excellent characteristics.

[0402] In addition, the current density is 50mA / cm 2 The graph shows the change in brightness with respect to the operating time. As shown in FIG. 42, the light-emitting element 5 which is a light-emitting element of one embodiment of the present invention is a comparative light-emitting element. The decrease in luminance due to the accumulation of driving time is smaller than that of the optical element 3, and the light emitting element has a long life. I realized that. EXAMPLES

[0403] In this example, a light-emitting element 6 of one embodiment of the present invention and a comparative light-emitting element 4 will be described. The structural formulas of the organic compounds used in the element 6 and the comparative light-emitting element 4 are shown below.

[0404] [Chemical formula]

[0405] (Method for manufacturing the light-emitting element 6) First, indium tin oxide (ITSO) containing silicon oxide was deposited on a glass substrate by sputtering to form the first electrode 101. The film thickness was 70 nm, and the electrode area was 2 mm × 2 mm.

[0406] Next, as a pretreatment for forming a light-emitting element on the substrate, the substrate surface was washed with water and baked at 200 °C for 1 hour, and then UV ozone treatment was performed for 370 seconds.

[0407] Thereafter, the substrate was introduced into a vacuum evaporation apparatus whose internal pressure was reduced to about 10 -4 Pa, and vacuum baking was performed at 170 °C for 30 minutes in the heating chamber of the vacuum evaporation apparatus, and then the substrate was allowed to cool for about 30 minutes and cooled.

[0408] Next, with the surface on which the first electrode 101 was formed facing downward, the substrate on which the first electrode 101 was formed was fixed to a substrate holder provided in the vacuum evaporation apparatus, and on the first electrode 101, by a vapor deposition method using resistance heating, N-(1,1'-biphenyl -4-yl)-6-phenyl-N-[4-(9-phenylcarbazol-3-yl)phenyl]benzo[b]naphtho[d]furan-8-amine (abbreviation: PCBBiBnf) represented by the above structural formula (xi), and NDP-9 (Analytical Factory Co., Ltd., Material Serial Number: 1S20170124) were co-evaporated at a weight ratio of 1:0.1 (= PCBBiBnf: NDP-9) to a thickness of 10 nm. The positive hole injection layer 111 was formed.

[0409] Next, on the positive hole injection layer 111, as the first positive hole transport layer 112-1, PCBBiBnf was evaporated to a thickness of 20 nm, and then, as the second positive hole transport layer 112-2, the N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p-terphenyl (abbreviation: DBfBB1TP) represented by the above structural formula (x ii) was evaporated to a thickness of 10 nm to form the positive hole transport layer 112.

[0410] Subsequently, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA) represented by the above structural formula (iv), and the above N,N’-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6Bnf APrn-03) represented by the structural formula (v) were co-evaporated at a weight ratio of 1:0.03 (=cgDBCzPA:1,6BnfAPr n-03) to a thickness of 25 nm to form the light-emitting layer 113.

[0411] Thereafter, on the light-emitting layer 113, 2-[3’-(9,9-dimethyl-9H-fluoren-2-yl)-1,1’-biphenyl-3-yl]-4,6 -diphenyl-1,3,5-triazine (abbreviation: mFBPTzn) represented by the above structural formula (xiii) was evaporated to a film thickness of 10 nm, and then 2-{4-[9,10-di(naphtha lene-2-yl)-2-anthryl]phenyl}-1-phenyl-1H-benzimidazole (abbreviation: ZADN) represented by the above structural formula (xiv) and 8-hydroxyquinolinolato- represented by the above structural formula (xv) Lithium (abbreviation: Liq) was co-evaporated at a weight ratio of 1:1 (= ZADN: Liq) to form an electron transport layer 114 with a thickness of 1 5 nm.

[0412] After forming the electron transport layer 114, Liq was evaporated to a thickness of 1 nm to form an electron injection layer 1 15. Subsequently, aluminum was evaporated to a thickness of 200 nm to form a second electrode 102, and the light-emitting device 3 of this example was fabricated.

[0413] (Fabrication method of comparative light-emitting device 4) Comparative light-emitting device 4 was fabricated in the same manner as light-emitting device 6, except that PCBBiBnf in light-emitting device 5 was replaced with N,N-bis(4-biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]fura n-8-amine (abbreviation: BBABnf).

[0414] The device structures of light-emitting device 5 and comparative light-emitting device 3 are summarized in the following table.

[0415]

Table 7

[0416] Light-emitting device 6 and comparative light-emitting device 4 were sealed with a glass substrate in a nitrogen atmosphere glove box so that the light-emitting device was not exposed to the atmosphere (a sealing material was applied around the device, and UV treatment and heat treatment at 80 °C for 1 hour were performed during sealing). After that, the initial characteristics and reliability of these light-emitting devices were measured. The measurements were performed at room temperature. The luminance-current density characteristics of light-emitting device 6 and comparative light-emitting device 4 are shown in Fig. 43, the current efficiency-luminance characteristics are shown in Fig. 44, the luminance-voltage characteristics are shown in Fig. 45, the current-voltage characteristics are shown in Fig. 46, and the external quantum efficiency-luminance

[0417] characteristics are shown in Fig. 47, and the current-voltage characteristics are shown in Fig. 48. characteristics are shown in Fig. 44, the luminance-voltage characteristics are shown in Fig. 45, the current-voltage characteristics are shown in Fig. 46, and the external quantum efficiency-luminance characteristics are shown in Fig. 47, and the current-voltage characteristics are shown in Fig. 48. The luminance characteristics are shown in FIG. 47, and the emission spectrum is shown in FIG. 48. m 2 The main characteristics of the area are shown in Table 6.

[0418] [Table 8]

[0419] 43 to 48 and Table 8, the light-emitting element 6 of one embodiment of the present invention is similar to the comparative light-emitting element 4. It was found that this was a blue light-emitting element with a relatively low driving voltage and good luminous efficiency.

[0420] In addition, the current density is 50mA / cm 2 The graph shows the change in brightness with respect to the operating time. 49, a graph showing the change in voltage is shown in FIG. 50. As shown in FIG. 49, The change in luminance of the light-emitting element 6 was similar to that of the comparative light-emitting element 4. As shown, the voltage change is small in the light-emitting element 6, and the light-emitting element 6 is a light-emitting element with good reliability. Understood. [Explanation of symbols]

[0421] 101: first electrode, 102: second electrode, 103: EL layer, 111: hole injection layer, 11 2: hole transport layer, 112-1: first hole transport layer, 112-2: second hole transport layer, 11 2-3: third hole transport layer, 113: light emitting layer, 114: electron transport layer, 115: electron injection layer 116: charge generation layer, 117: P-type layer, 118: electron relay layer, 119: electron injection bag 400: substrate; 401: first electrode; 403: EL layer; 404: second electrode; 05: sealing material, 406: sealing material, 407: sealing substrate, 412: pad, 420: IC Chip, 501: First electrode, 502: Second electrode, 511: First light-emitting unit, 51 2: Second light-emitting unit, 513: Charge generation layer, 601: Driving circuit section (source line driving circuit ), 602: Pixel section, 603: Driving circuit section (gate line driving circuit), 604: Sealing substrate, 6 05: Sealing material, 607: Space, 608: Wiring, 609: FPC (Flexible Printed Circuit), 610: Element substrate, 611: Switching FET, 612: Current control FET, 613: First electrode, 614: Insulator, 616: EL layer, 617: Second electrode, 618: Light-emitting element, 951: Substrate, 952: Electrode, 953: Insulating layer, 954: Partition layer, 9 55: EL layer, 956: Electrode, 1001: Substrate, 1002: Underlying insulating film, 1003: Gate Insulating film, 1006: Gate electrode, 1007: Gate electrode, 1008: Gate electrode, 10 20: First interlayer insulating film, 1021: Second interlayer insulating film, 1022: Electrode, 1024W: First electrode, 1024R: First electrode, 1024G: First electrode, 1024B: First elect rode, 1025: Partition, 1028: EL layer, 1029: Second electrode, 1031: Sealing substrate, 1032: Sealing material, 1033: Transparent base material, 1034R: Red coloring layer, 1034G: Green coloring layer, 1034B: Blue coloring layer, 1035: Black matrix, 1036: Overcoat layer, 1037: Third interlayer insulating film, 1040: Pixel section, 1041: Driving cir cuit section, 1042: Peripheral section, 2001: Housing, 2002: Light source, 2100: Robot, 21 10: Arithmetic unit, 2101: Illuminance sensor, 2102: Microphone, 2103: Upper ca mera, 2104: Speaker, 2105: Display, 2106: Lower camera, 2107 : Obstacle sensor, 2108: Moving mechanism, 3001: Lighting device, 5000: Housing, 5001 : Display unit, 5002: Second display unit, 5003: Speaker, 5004: LED lamp, 5 005: Operation key, 5006: Connection terminal, 5007: Sensor, 5008: Microphone , 5012: Support part, 5013: Earphone, 5100: Cleaning robot, 5101: Dis player, 5102: Camera, 5103: Brush, 5104: Operation button, 5150: Portable information terminal, 5151: Housing, 5152: Display area, 5153: Bending part, 5120: Dust, 5200: Display area, 5201: Display area, 5202: Display area, 5203: Display area, 7101: Housing, 7103: Display unit, 7105: Stand, 7107: Display unit, 7109 : Operation key, 7110: Remote control operation unit, 7201: Main body, 7202: Housing, 7203: Display unit, 7204: Keyboard, 7205: External connection port, 7206: Pointing device, 7210: Second display unit, 7401: Housing, 7402: Display unit, 7403: Op eration button, 7404: External connection port, 7405: Speaker, 7406: Mic, 740 0: Mobile phone, 9310: Portable information terminal, 9311: Display panel, 9313: Hinge, 9315: Housing

Claims

1. A light-emitting device having a light-emitting layer between an anode and a cathode, and having an organic compound represented by the following general formula (G1) between the anode and the light-emitting layer. 【Chemical 1】 (However, in the general formula (G1), R ０ is a group represented by the following general formula (g1), and R １ to R ９ are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.) [Chemical Formula 2] (In general formula (g1), Cz represents a group represented by the following general formula (g2). Also, Ar ４ represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a group represented by the following general formula (g3). Also, Ar ５ , Ar ６ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, n represents any one of integers from 1 to 3, and m represents any one of integers from 0 to 3, provided that when Ar ４ is a carbazolyl group, m is any one of integers from 1 to 3. Note that Ar ５ or Ar ６ may have multiple cases depending on the numerical values of n or m, and the plurality of Ar ５ or the plurality of Ar ６ each independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, the sum of the number of carbon atoms of Cz and Ar ５ , and the sum of the number of carbon atoms of Ar ４ and Ar ６ are each 60 or less.) [Chemical Formula 3] (In the general formula (g2), R １０ to R １８ among them, R １６ represents a bond that binds to Ar ５ , and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.) 【Chemical Formula 4】 (In the general formula (g3), one of R ２０ to R ２８ represents a bond that binds to Ar ６ , and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.)

2. In Claim 1, R １０ An organic compound having a light-emitting element having a phenyl group which is substituted or unsubstituted.

3. A light-emitting device having a light-emitting layer between an anode and a cathode, and having an organic compound represented by the following general formula (G1) between the anode and the light-emitting layer. 【Chemical Formula 5】 (However, in the general formula (G1), R ０ is a group represented by the following general formula (g1), and R １ to R ９ each independently represents any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.) 【Chemical Formula 6】 (In general formula (g1), Cz represents a group represented by the following general formula (g2). Also, Ar ４ represents either a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a group represented by the following general formula (g3). Also, Ar ５ , Ar ６ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, n represents any one of integers from 1 to 3, and m represents any one of integers from 0 to 3, provided that when Ar ４ is a carbazolyl group, m is any one of integers from 1 to 3. Note that Ar ５ or Ar ６ may have multiple cases depending on the numerical values of n or m, and the plurality of Ar ５ or the plurality of Ar ６ each independently represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 54 carbon atoms. Also, the sum of the number of carbon atoms of Cz and Ar ５ and the sum of the number of carbon atoms of Ar ４ and Ar ６ are each 60 or less.) 【Chemical Formula 7】 (In the general formula (g2), R １０ to R １８ among them, R １０ represents a bond that binds to Ar ５ , and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, respectively.) 【Chemical Formula 8】 (In the general formula (g3), one of R ２０ to R ２８ represents a bond that binds to Ar ６ , and the rest are each independently hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a halogen, a haloalkyl group having 1 to 6 carbon atoms, and any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.)

4. In any one of Claims 1 to 3, A light-emitting device having an organic compound in which n is any one of integers from 1 to 3.

5. In any one of Claims 1 to 4, Ar ４ An organic compound having a light-emitting element having a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms.

6. In any one of Claims 1 to 4, Ar ４ An organic compound having a light-emitting element having a phenyl group which is substituted or unsubstituted.

7. In any one of Claims 1 to 6, Ar ５ A light-emitting device having an organic compound in which Ar is a substituted or unsubstituted phenylene group.

8. In any one of Claims 1 to 7, Ar ６ An organic compound having a light-emitting element, wherein Ar is a substituted or unsubstituted phenylene group.

9. In any one of Claims 1 to 8, R １ to R ８ A light-emitting device having an organic compound that is hydrogen, respectively, independently.

10. A light-emitting device according to any one of Claims 1 to 9, and having at least one of a transistor and a substrate.

11. An electronic device having the light-emitting device according to Claim 10, and having at least one of a sensor, an operation button, a speaker, and a microphone.

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