Organic compound

Abstract

To provide a novel organic compound that is effective in improving element characteristics and reliability.SOLUTION: The present invention provides an organic compound represented by the following general formula (G1), having a dibenzobenzofuroquinoxaline skeleton or a dibenzobenzothienoquinoxaline skeleton (where, Q represents O or S, at least one of R1 to R12 represents a first group having a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring having 3 to 30 carbon atoms forming the ring, and the other or others of R1 to R12 each independently represent any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, and a group having 1 to 50 carbon atoms).SELECTED DRAWING: None

Description

[Technical field]

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. However, one aspect of the present invention is not limited thereto. Alternatively, one aspect of the present invention relates to a process, a manufacturing method, or a driving method. Composition of matter. Specific examples of the present invention include semiconductor devices, display devices, and liquid crystal display devices. can. [Background technology]

[0002] Light-emitting elements (also called organic EL elements) are thin, lightweight, and have an EL layer sandwiched between a pair of electrodes. This was applied because of its characteristics such as high-speed response to force signals and low power consumption. The display is attracting attention as the next generation flat panel display.

[0003] The light-emitting element is a device that emits light by applying a voltage between a pair of electrodes, and the electrons injected from each electrode are The electrons and holes recombine in the EL layer, and the luminescent material (organic compound) contained in the EL layer becomes excited. When the excited state returns to the ground state, light is emitted. , singlet excited state (S * ) and triplet excited states (T * ) and emission from the singlet excited state. The light emitted from the triplet excited state is called fluorescence, and the light emitted from the triplet excited state is called phosphorescence. The statistical generation ratio of these is S * :T * =1:3. From luminous materials The emission spectrum obtained is specific to the luminescent material, and different types of organic compounds emit By using it as a light-emitting material, light-emitting elements with various emission colors can be obtained.

[0004] Regarding such light-emitting elements, in order to improve their element characteristics, improvements in element structure and material development and the like are being actively carried out (for example, see Patent Document 1).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] In the development of light-emitting elements, organic compounds used in light-emitting elements are very important for enhancing their characteristics and reliability. Therefore, in one aspect of the present invention, a novel organic compound is provided. That is, a novel organic compound effective for enhancing element characteristics and reliability is provided. Also, in one aspect of the present invention, a novel organic compound that can be used in a light-emitting element is provided. Further, in one aspect of the present invention, a novel organic compound that can be used in the EL layer of a light-emitting element is provided. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc. Moreover, a novel high-efficiency and highly reliable light-emitting element using the novel organic compound according to one aspect of the present invention is provided. Also, a novel light-emitting device, a novel electronic device, or a novel lighting device is provided. It should be noted that the description of these problems does not prevent the existence of other problems. It should be noted that one aspect of the present invention does not necessarily need to solve all of these problems. It should be noted that other problems will become apparent from the descriptions in the specification, drawings, claims, etc., and it is possible to extract these other problems from the descriptions in the specification, drawings, claims, etc.

Means for Solving the Problem

[0007] One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0008]

Chemical Formula

[0009] However, in the general formula (G1), Q represents O or S, and at least one of R 1 ~R 12 is a first group having either a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 30 carbon atoms forming a ring, and the others each independently represent hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0010]

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

[0011]

Chemical Formula

[0012] However, in the general formula (G1), Q represents O or S, and at least one of R 1 ~R 12 is a first group having a hole-transporting skeleton with 3 to 30 carbon atoms forming a substituted or unsubstituted ring, and the others each independently represent hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or

[0013]

[0014]

[0014]

Chemical Formula

[0015] However, in the general formula (G1), Q represents O or S, and R 1 ~R 12 at least one of which is a full olene skeleton, phenanthrene skeleton, triphenylene skeleton, naphthalene skeleton, dibenzothio phene skeleton, dibenzofuran skeleton, or a first group having any of the carbazole skeletons and the others each independently represent hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or any of groups having 1 to 50 carbon atoms.

[0016] In addition, in each of the above configurations, it is preferable that the total number of carbon atoms of the first group is 3 to 100.

[0017] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0018]

Chemical formula

[0019] However, in the general formula (G1), Q represents O or S, and R 1 ~R 12 at least one of which is a first group to which a structure represented by any one of the following general formulas (A-1 ) to (A-21) is bonded via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms forming a ring or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring, and the others each independently represent hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or any of groups having 1 to 50 carbon atoms.

Chemical formula

[0020] ​​

[0021] However, in general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 represents each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. or an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0022] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0023]

Chemical formula

[0024] However, in general formula (G1), Q represents O or S, and at least one of R 1 ~R 12 is a first group represented by any one of the following general formulas (A-1) to (A-21), and the others are each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0025]

Chemical formula

[0026] However, in general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 represents each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. or an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0027] Moreover, another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0028]

Chemical formula

[0029] However, in the general formula (G1), Q represents O or S, and R 3 is a first group having either a substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring with 3 to 3 0 carbon atoms forming a ring, and R , R 1 , R 2 and R 4 ~R 12 each independently represents hydrogen, a halogeno group, a hydroxy xy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0030] Moreover, another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0031]

Chemical formula

[0032] However, in the general formula (G1), Q represents O or S, and R 3 is a first group having a hole-transporting skeleton with 3 to 3 0 carbon atoms forming a ring and being substituted or unsubstituted, and R 1 , R 2 and R 4 ~R 12 each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group , or a group having 1 to 50 carbon atoms.

[0033] Moreover, another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0034] [Chemical formula]

[0035] However, in the general formula (G1), Q represents O or S, and R 3 is a first group having any one of a fluorene skeleton, a phenanthrene skeleton, a triphenylene skeleton, a naphthalene skeleton, a dibenzothiophene skeleton, a dibenzof uran skeleton, or a carbazole skeleton, and R 1 , R 2 and R 4 ~R 12 each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0036] In addition, in each of the above configurations, the total number of carbon atoms of R 3 is preferably 3 to 100.

[0037] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0038] [Chemical formula]

[0039] However, in the general formula (G1), Q represents O or S, and R 3 is a first group in which a structure represented by any one of the following general formulas (A-1) to (A-21) is bonded via a substituted or unsubstituted arylene group having 6 to 2 4 carbon atoms forming a ring, or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring, and R 1 , R 2 and R 4 ~R 12 each independently represents Each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0040]

Chemical formula

[0041] However, in general formulas (A-1) to (A-21), Q’ represents O or S, and R 13 ~R 24 each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms that forms a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0042]

[0043]

Chemical formula

[0044] However, in general formula (G1), Q represents O or S, R 3 is a first group represented by any one of the following general formulas (A-1) to (A -21), and R 1 , R 2 and R 4 ~R 12 each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0045]

Chemical formula

[0046] ​In the general formulas (A-1) to (A-21), Q′ represents O or S, and R 13 ~R 24 teeth Each independently is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a substituent having 5 to 7 carbon atoms forming a ring. or an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or or an unsubstituted carbazolyl group.

[0047] In each of the above structures, the group having 1 to 50 carbon atoms is an alkyloxy group, an aryloxy group, an acyclic group, Amino groups substituted with alkyl groups, amino groups substituted with aryl groups, cyano groups, carboxy groups, etc. Substituted with silyl, alkyloxycarbonyl, aryloxycarbonyl, or alkyl groups silyl groups substituted with aryl groups, alkyl groups, cycloalkyl groups, hexamethylsilyl groups, cycloalkyl ... It is either a heteroaryl group or an aryl group.

[0048] Another embodiment of the present invention is an organic compound represented by structural formula (100) or structural formula (125). It is a compound.

[0049] [ka]

[0050] Another aspect of the present invention is a compound having a benzofuroquinoxaline skeleton or a benzothienoquinoxaline skeleton. This is a light-emitting element that uses an organic compound having a phosphorus skeleton. ]benzofuro[2,3-b]quinoxaline skeleton or dibenzo[f,h][1]benzothiamine Furthermore, the light-emitting device is a light-emitting device using an organic compound having an eno[2,3-b]quinoxaline skeleton. In addition to the above organic compounds, a substance that converts triplet excitation energy into luminescence, e.g. For example, a light-emitting element having a phosphorescent material or a TADF material containing an organometallic complex is also included in one aspect of the present invention. Included.

[0051] Another aspect of the present invention is a light-emitting element using the organic compound which is one aspect of the present invention described above. Note that a light-emitting element having an EL layer between a pair of electrodes or a light-emitting layer included in the EL layer formed using the organic compound which is one aspect of the present invention is also included in one aspect of the present invention. In addition to the light-emitting element, a light-emitting device having a transistor, a substrate, etc. is also included in the scope of the invention. Further, in addition to these light-emitting devices, an electronic device or a lighting device having a microphone, a camera, an operation button, an external connection part, a housing, a cover, a support base, or a speaker, etc. is also included in the scope of the invention. Note that a light-emitting element having an EL layer between a pair of electrodes or a light-emitting layer included in the EL layer formed using the organic compound which is one aspect of the present invention is also included in one aspect of the present invention. In addition to the light-emitting element, a light-emitting device having a transistor, a substrate, etc. is also included in the scope of the invention. Further, in addition to these light-emitting devices, an electronic device or a lighting device having a microphone, a camera, an operation button, an external connection part, a housing, a cover, a support base, or a speaker, etc. is also included in the scope of the invention. Further, in addition to these light-emitting devices, an electronic device or a lighting device having a microphone, a camera, an operation button, an external connection part, a housing, a cover, a support base, or a speaker, etc. is also included in the scope of the invention. Further, in addition to these light-emitting devices, an electronic device or a lighting device having a microphone, a camera, an operation button, an external connection part, a housing, a cover, a support base, or a speaker, etc. is also included in the scope of the invention. Included in the scope of the invention.

[0052] The organic compound which is one aspect of the present invention can be used as a light-emitting substance, but can be used in the light-emitting layer of a light-emitting element in combination with a light-emitting substance (phosphorescent compound) that emits phosphorescence. That is, since it is possible to obtain light emission from the triplet excited state in the light-emitting layer, the light-emitting element can be made highly efficient, which is very effective. Therefore, a light-emitting element using a combination of the organic compound which is one aspect of the present invention and a phosphorescent compound in the light-emitting layer is included in one aspect of the present invention. Further, in addition to the above, a configuration in which a third substance is added to the light-emitting layer may also be used. That is, since it is possible to obtain light emission from the triplet excited state in the light-emitting layer, the light-emitting element can be made highly efficient, which is very effective. Therefore, a light-emitting element using a combination of the organic compound which is one aspect of the present invention and a phosphorescent compound in the light-emitting layer is included in one aspect of the present invention. Further, in addition to the above, a configuration in which a third substance is added to the light-emitting layer may also be used. Further, in addition to the above, a configuration in which a third substance is added to the light-emitting layer may also be used. Good.

[0053] One aspect of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having the light-emitting device in the scope. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). Also, a connector, for example, an F One aspect of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having the light-emitting device in the scope. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). Modules with a PC (Flexible printed circuit) or TCP (Tape Carrier Package) attached, modules with a printed wiring board provided at the tip of the TCP, or modules with an IC (Integrated Circuit) directly mounted on a light-emitting element by the COG (Chip On Glas s) method are all included in the light-emitting device as well. Let it be so.

Advantages of the Invention

[0054] One aspect of the present invention can provide a novel organic compound. That is, it can provide a novel organic compound effective in enhancing device characteristics and reliability. Further, in one aspect of the present invention, it can provide a novel organic compound that can be used in a light-emitting element. Also in one aspect of the present invention, it can provide a novel organic compound that can be used in the EL layer of a light-emitting element. Further in one aspect of the present invention, it can provide a novel, highly efficient, and reliable light-emitting element using the novel organic compound. In addition, it can provide a novel light-emitting device, a novel electronic device, or a novel lighting device. 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 have all of these effects . Note that other effects will become 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. Note that one aspect of the present invention does not necessarily have all of these effects . Note that other effects will become 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. 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 have all of these effects. Note that other effects will become 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

[0055]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Figure 10

Figure 11

Figure 12

Figure 13

Figure 14

Figure 15

Figure 16

Figure 17

Embodiments for Carrying Out the Invention

[0056] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and its form and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention is not interpreted as being limited to the description of the embodiments shown below. ​

[0057] In addition, with regard to the position, size, range, etc. of each component shown in the drawings and the like, for the sake of simplicity of understanding, they may not represent the actual position, size, range, etc. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings and the like.

[0058] Also, in this specification and the like, when explaining the configuration of the invention using the drawings, the same reference numerals are commonly used among different drawings.

[0059] (Embodiment 1) In this embodiment, an organic compound which is one aspect of the present invention will be described.

[0060] The organic compound which is one aspect of the present invention is an organic compound having a structure represented by the following general formula (G1) having a dibenzobenzofuroquinoxaline skeleton or a dibenzobenzothienoquinoxaline skeleton.

[0061] [Chemical formula]

[0062] In the general formula (G1), Q represents O or S, and at least one of R 1 ~R 12 is , a first group having either a substituted or unsubstituted condensed aromatic ring or a condensed heteroaromatic ring having 3 to 30 carbon atoms forming a ring, and the others each independently represent hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or any of groups having 1 to 50 carbon atoms.

[0063] Also, in addition to the above configuration, the above general formula (G1) is "In the general formula (G1), Q represents O or S and R 1 ~R 12 ​​​​​​​At least one of them is a first group having a substituted or unsubstituted hole-transporting skeleton with 3 to 30 carbon atoms forming a ring, and the others are each independently hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. It may be stated as follows. It may also be stated as follows. "One of them is a first group having a substituted or unsubstituted hole-transporting skeleton with 3 to 30 carbon atoms forming a ring, and the others are each independently hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms."

[0064] In addition to the above configuration, the general formula (G1) may also be "In the general formula (G1), Q represents O or S, and at least one of R 1 ~R 12 is a first group having any one of a fluorene skeleton, a phenanthrene skeleton, a triphenylene skeleton, a naphthalene skeleton, a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton, and the others are each independently hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms." It may be stated as follows. It may also be stated as follows. "In addition to the above configuration, the general formula (G1) may also be "In the general formula (G1), Q represents O or S, and at least one of R

[0065] ~R is a first group having any one of a fluorene skeleton, a phenanthrene skeleton, a triphenylene skeleton, a naphthalene skeleton, a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton, and the others are each independently hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms."

[0066] In addition, it is preferable that the first group in each of the above-described configurations has a total carbon number of 3 to 100. It may be stated as follows. 1 ~R 12 In addition to the above configuration, the general formula (G1) may also be "In the general formula (G1), Q represents O or S, and at least one of R ~R is a first group to which a structure represented by any one of the following general formulas (A-1) to (A-21) is bonded via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms forming a ring or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring, and the others are each independently hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms."

[0067] It may be stated as follows.In addition to the above configuration, the general formula (G1) is "In the general formula (G1), Q represents O or S , R 1 ~R 12 At least one of them is a first group represented by any one of the following general formulas (A-1) to (A-21), and the others are each independently hydrogen, a halogeno group, a hydroxy group , an amino group, a nitro group, or any one of groups having 1 to 50 carbon atoms." may also be used.

[0068]

Chemical formula

[0069] In the general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0070] In addition to the above configuration, the general formula (G1) is "In the general formula (G1), Q represents O or S , R 3 is a first group having either a substituted or unsubstituted condensed aromatic ring or a substituted or unsubstituted condensed heteroaromatic ring having 3 to 30 carbon atoms forming a ring, and R 1 , R 2 and R 4 ~R 12 are each independently hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or any one of groups having 1 to 50 carbon atoms." may also be used.

[0071] In addition to the above configuration, the general formula (G1) is "In the general formula (G1), Q represents O or S , R3 is a first group having a substituted or unsubstituted hole-transporting backbone with 3 to 30 carbon atoms forming a ring and R 1 , R 2 and R 4 ~R 12 each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms . It may be stated as follows.

[0072] In addition to the above configuration, the general formula (G1) may also be stated as follows: "In the general formula (G1), Q represents O or S , and R 3 is a first group having any one of a fluorene backbone, a phenanthrene backbone, a triphenylene backbone, a naphtha lene backbone, a dibenzothiophene backbone, a dibenzofuran backbone, or a carbazole backbone, and R , R 1 , R 2 and R 4 ~R 12 each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms . It may be stated as follows.

[0073] In addition, R 3 in each of the above-described configurations preferably has a total carbon number of 3 to 100.

[0074] In addition to the above configuration, the general formula (G1) may also be stated as follows: "In the general formula (G1), Q represents O or S , and R 3 is a first group in which a structure represented by any one of the following general formulas (A-1) to (A-21) is bonded via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms forming a ring or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring, and R , R , R 1 , R 2 and R 4~R 12 Each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.」 It may also be good.

[0075] In addition to the above configuration, the general formula (G1) is 「In the general formula (G1), Q represents O or S , and R 3 is a first group represented by any one of the following general formulas (A-1) to (A-21) , and R 1 , R 2 and R 4 ~R 12 Each independently represents hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.」 It may also be good.

[0076]

Chemical formula

[0077] In the general formulas (A-1) to (A-21), Q’ represents O or S, and R 13 ~R 24 Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. or unsubstituted carbazolyl group.

[0078] In each of the above configurations, the group having 1 to 50 carbon atoms is an alkyloxy group, an aryloxy group, an amino group substituted with an alkyl group, an amino group substituted with an aryl group, a cyano group, a car boxyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, a silyl group substituted with an alkyl group, a silyl group substituted with an aryl group, an alkyl group, a cycloalkyl group substituted with an alkyl group, a silyl group substituted with an aryl group, an alkyl group, a cycloalkyl is preferably any one of a group, a heteroaryl group, or an aryl group. In addition, these specific examples include a methoxy group, an ethoxy group, a propoxy group, a tert-butoxy group, a phenoxy group, a 4-methylphenoxy group, a 3,5-dimethylphenoxy group, a 1-naphthoxy group, a 2-naphthoxy group, a methylamino group, an ethylamino group, a dimethylamino group, a diethyl amino group, a methylethylamino group, a phenylmethylamino group, a phenylamino group, a diphenyl amino group, a 1-naphthylamino group, a 2-naphthylamino group, an N-1-naphthyl-N -phenylamino group, an N-2-naphthyl-N-phenylamino group, a bis(biphenyl-4 -yl)amino group, an N,N-bis(p-terphenyl)amino group, a methoxycarbonyl group an ethoxycarbonyl group, a phenoxycarbonyl group, a trimethylsilyl group, a triphenyl silyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group a tert-butyl group, an n-hexyl group, a benzyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, a phenanthrenyl group, a triphenyl renyl group, a 9,9-dimethylfluorenyl group, a pyridyl group, a quinolyl group, a 9-carbazolyl group, a 9-phenyl-2-carbazolyl group, a 9-phenyl-3-carbazolyl group a dibenzofuranyl group, a dibenzothiophenyl group, etc. can be mentioned. In addition, spirofluorenyl groups and groups having 25 or fewer carbon atoms, such as an N,N-bis(p-biphenylyl)amino group, that is, groups having 1 to 25 carbon atoms are preferable in consideration of sublimability.

[0079] In the organic compound according to one aspect of the present invention, the hydrogen contained in the skeleton may be deuterium. It is also good.

[0080] In each of the above configurations, the substitution in the general formula (G1) or the general formulas (A-1) to (A-21) preferably refers to a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an s ec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, etc., having 1 to 6 carbon atoms alkyl group, or a phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 1- naphthyl group, 2-naphthyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group substitution by a substituent such as an aryl group having 6 to 12 carbon atoms. These substituents may be bonded to each other to form a ring. For example, when the arylene group is a 2,7-fluorenylene group having two phenyl groups at the 9-position as a substituent, the phenyl groups may be bonded to each other to form a spiro-9,9'-bifluorene-2,7-diyl group. It is also good. It is also good. It is also good.

[0081] In each of the above configurations, specific examples of the condensed aromatic ring or condensed heteroaromatic ring having 3 to 30 carbon atoms formed by R 1 ~R 12 represented in the general formula (G1) include a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a naphthalene ring, a benzothiophene ring, a benzofuran ring, an indole ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a dibenzothiophene ring, a benzonaphthothiophene ring, a dibenzofuran ring, a benzonaphthofuran ring a carbazole ring, a benzocarbazole ring, or a dibenzocarbazole ring, etc. are mentioned. are mentioned. a carbazole ring, a benzocarbazole ring, or a dibenzocarbazole ring, etc. are mentioned. are mentioned.

[0082] In addition, in each of the above configurations, R in the general formula (G1) 1 ~R 12 represents a specific example of a hole-transporting skeleton having 3 to 30 carbon atoms forming a ring, such as a naphthalene ring, a benzothiophene ring , a benzofuran ring, an indole ring, a fluorene ring, a phenanthrene ring, a triphenylene ring , a dibenzothiophene ring, a benzonaphthothiophene ring, a dibenzofuran ring, a benzonaphtho furan ring, a carbazole ring, a benzocarbazole ring, or a dibenzocarbazole ring, etc. can be mentioned.

[0083] In addition, in each of the above configurations, R in the general formula (G1) 1 ~R 12 represents a specific example of an arylene group having 6 to 24 carbon atoms forming a ring, such as a phenylene group, a naphthalenediyl group, a bi phenyldiyl group, a terphenyldiyl group, a fluorenediyl group, a phenanthrenediyl group, a triphenylenediyl group, etc. can be mentioned.

[0084] In addition, in each of the above configurations, R in the general formula (G1) 1 ~R 12 represents a specific example of a heteroarylene group having 3 to 24 carbon atoms forming a ring, such as a pyridinediyl group, a pyrazinediyl group, a pyrimidinediyl group, a triazinediyl group, a triazolediyl group, an oxadiaz ole diyl group, a thiadiazolediyl group, an oxazolediyl group, a thiazolediyl group, a thiophenediyl group, a pyrrolediyl group, a furandiyl group, a selenophenediyl group, a ben zothiophenediyl group, a benzopyrrolediyl group, a benzofurandiyl group, a quinolinediyl group, an isoquinolinediyl group, a dibenzothiophenediyl group, a carbazolediyl group, di benzofurandiyl group, etc. can be mentioned. ​​​​

[0085] Also, in each of the above configurations, R in general formulas (A-1) to (A-21) 13 ~R 24 represents , specific examples of the alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group, propyl group, iso propyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pent yl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, neohex yl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-di methylbutyl group, 2,3-dimethylbutyl group, and the like.

[0086] Also, in each of the above configurations, R in general formulas (A-1) to (A-21) 13 ~R 24 represents , specific examples of the cycloalkyl group having 5 to 7 carbon atoms forming a ring include cyclopentyl group , cyclohexyl group, cycloheptyl group, and the like.

[0087] Next, specific structural formulas of the organic compound which is one aspect of the present invention described above are shown below.

[0088] [Chemical formula]

[0089] [Chemical formula]

[0090] [Chemical formula]

[0091] [Chemical formula]

[0092]

Chem.

[0093]

Chem.

[0094]

Chem.

[0095] Note that the organic compounds represented by the above structural formulas (100) to (175) are an example included in the organic compound represented by the above general formula (G1), and the organic compound of one aspect of the present invention is not limited to this. but is not limited thereto.

[0096] Next, an example of a method for synthesizing an organic compound, which is one aspect of the present invention, represented by the general formula (G1) will be described.

[0097] First, an example of a method for synthesizing an organic compound, a dibenzobenzofuroquinoxaline derivative, or a dibenzobenzothienoquinoxaline derivative represented by the following general formula (G1) will be described.

[0098]

Chem.

[0099] In the general formula (G1), Q represents O or S, and R 1 ~R 12 each independently represents hydrogen , or a substituent, and at least one of R 1 ~R 12 has 3 to ​​​​Represents either a 30-substituted or unsubstituted condensed aromatic ring or condensed heteroaromatic ring.

[0100] ≪Synthesis method of halogen compound represented by general formula (G0)≫ First, a halogen compound (general formula (G 0)) used for the synthesis of a dibenzobenzofuroquinoxaline derivative or a dibenzobenzothienoquinoxaline derivative represented by the above general formula (G1) will be described.

[0101] The halogen compound represented by the following general formula (G0) can be easily synthesized, for example, by the synthesis methods shown below. Here, the first synthesis method and the second synthesis method are shown.

[0102]

Chemical formula

[0103] In the above general formula (G0), Q represents O or S, and R 31 ~R 42 each independently represents hydrogen or a substituent, and at least one of R 31 ~R 42 represents a halogen.

[0104] <First synthesis method> The halogen compound represented by the above general formula (G0) can be obtained by reacting a halogenated dibenzoquinoxaline derivative (A1) having a phenyl group substituted with a hydroxy group or a sulfanyl group with a base (A2) such as potassium carbonate as shown in the following synthesis scheme (A-1).

[0105]

Chemical formula

[0106] ​​​ In the synthesis scheme (A-1), Q represents O or S, X represents a halogen, R 31 ~R 42 each independently represents hydrogen or a substituent, and at least one of R 31 ~R 42 represents a halogen.

[0107] <Second Synthesis Method> The halogen compound represented by the above general formula (G0) can also be obtained by reacting a phenyl group substituted with a methyloxy group or a methylsulfanyl group, a dibenzoquinoxaline derivative (A1’) having an amino group, and tert-butyl nitrite as shown in the following synthesis scheme (A-1’).

[0108]

Chemical Formula

[0109] In the synthesis scheme (A-1’), Q represents O or S, and R 31 ~R 42 each independently represents hydrogen or a substituent, and at least one of R represents a halogen. 31 ~R 42

[0110] ≪Synthesis Method of Organic Compound Represented by General Formula (G1)≫ Next, a method for synthesizing the dibenzobenzofuroquinoxaline derivative or dibenzobenzothienoquinoxaline derivative represented by the above general formula (G1) will be described.

[0111] The dibenzobenzofuroquinoxaline derivative or dibenzobenzothienoquinoxaline derivative represented by the above general formula (G1) can be obtained as shown in the following synthesis scheme (A-2), from the above ​​​​​​ The halogen compound (G0) obtained by the scheme (A-1) or (A-1') and boron The compound (B1) can be obtained by coupling with the acid compound (B2).

[0112] [ka]

[0113] In the synthetic scheme (A-2), Q represents O or S, and R 1 ~R 12 , and R 31 ~R 42 each independently represents hydrogen or a substituent, and R 1 ~R 12 Few At least one of the rings is a substituted or unsubstituted condensed aromatic ring having 3 to 30 carbon atoms, or In addition, B 1 is a boronic acid or boronic ester or represents a cyclic triol borate salt, etc.

[0114] The above-mentioned compounds (A1) and (A1') are commercially available in various types or can be synthesized. Therefore, the dibenzobenzofuran represented by the general formula (G1) and which is one embodiment of the present invention can be obtained. There are many types of quinoxaline derivatives, or dibenzobenzothienoquinoxaline derivatives. Therefore, the organic compound according to one embodiment of the present invention can be synthesized in a variety of ways. It is characterized by being rich in

[0115] The specific structural formula of the above-mentioned compound (G0) is shown below.

[0116] [ka]

[0117] [Chemical formula]

[0118] Incidentally, the organic compounds represented by the above structural formulas (200) to (223) are an example included in the halogen compound represented by the above general formula (G0), but are not limited thereto. It is not limited to this, and may be synthesized by any other synthesis method.

[0119] As described above, an example of the method for synthesizing an organic compound, a dibenzobenzofuroquinoxaline derivative, or a dibenzobenzothienoquinoxaline derivative, which is one aspect of the present invention, has been described. However, the present invention is not limited to this, and may be synthesized by any other synthesis method. is not limited thereto, and may be synthesized by any other synthesis method.

[0120] Incidentally, the organic compound shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments.

[0121] Incidentally, the organic compound, which is one aspect of the present invention described above, has electron transporting properties and hole transporting properties. Therefore, it can be used as a host material for a light-emitting layer, or also for an electron transporting layer or a hole transporting layer. In addition, since the organic compound, which is one aspect of the present invention, can maintain a relatively high T1 level, it is preferably used as a host material in combination with a substance that emits phosphorescence (phosphorescent material). In addition, since it exhibits fluorescence emission, it can itself be used as a light-emitting substance of a light-emitting element. Therefore, a light-emitting element containing these organic compounds is also included in one aspect of the present invention.

[0122] In addition, the organic compound, which is one aspect of the present invention, has a low LUMO level and is suitable as a compound that easily accepts electrons. Therefore, it is preferably used as a host material for an electron transporting layer or a light-emitting layer. Preferably, the driving voltage of the light-emitting element can be reduced thereby.

[0123] In addition, by combining an organic compound which is one aspect of the present invention with an organic compound having a high HOMO level (specifically, -5.7 eV or higher) and being prone to receive holes, an exciplex can be formed, and the excitation energy can be efficiently transferred from this exciplex to a light-emitting substance, so that the efficiency, reliability, and driving voltage of the phosphorescent light-emitting element can be improved. Regarding specific examples of the organic compound (hole-transporting material and electron-transporting material) to be combined with the organic compound which is one aspect of the present invention, the materials shown in Embodiment 2 can be appropriately used. By using the organic compound which is one aspect of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high luminous efficiency can be realized. Also, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can be realized.

[0124] In addition, by using the organic compound which is one aspect of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high luminous efficiency can be realized. Also, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can be realized.

[0125] In this embodiment, one aspect of the present invention has been described. Also, in other embodiments, one aspect of the present invention will be described. However, one aspect of the present invention is not limited to these. That is, in this embodiment and other embodiments, various aspects of the invention are described, so one aspect of the present invention is not limited to a specific aspect. For example, as one aspect of the present invention, an example when applied to a light-emitting element has been shown, but one aspect of the present invention is not limited to this. Also, depending on the situation, one aspect of the present invention may be applied to things other than the light-emitting element. Also, depending on the situation, one aspect of the present invention may not be applied to the light-emitting element. Also, depending on the situation, one aspect of the present invention may be applied to things other than the light-emitting element. Also, depending on the situation, one aspect of the present invention may not be applied to the light-emitting element.

[0126] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments. This is possible.

[0127] (Embodiment 2) In this embodiment, a light-emitting element, which is one aspect of the present invention, will be described. Note that an organic compound, which is one aspect of the present invention, can be used for the light-emitting element described in this embodiment. This is possible.

[0128] ≪Basic Structure of Light-Emitting Element≫ FIG. 1(A) shows a light-emitting element in which an EL layer is sandwiched between a pair of electrodes. Specifically, it has a structure in which an EL layer 103 including a light-emitting layer is sandwiched between a first electrode 101 and a second electrode 102. This is possible. This is possible.

[0129] FIG. 1(B) shows a light-emitting element having a stacked structure (tandem structure) in which a plurality of (two layers in FIG. 1(B)) EL layers (103a, 103b) are provided between a pair of electrodes and a charge generation layer 104 is sandwiched between the EL layers. Such a light-emitting element having a tandem structure can realize a light-emitting device that can be driven at a low voltage and has low power consumption. This is possible. This is possible. This is possible.

[0130] Note that the charge generation layer 104 has a function of injecting electrons into one EL layer (103a or 103b) and holes into the other EL layer (103b or 103a) when a voltage is applied between the first electrode 101 and the second electrode 102. Therefore, in FIG. 1(B), when a voltage is applied so that the potential of the first electrode 101 is higher than that of the second electrode 102, electrons are injected from the charge generation layer 104 into the EL layer 103a, and holes are injected into the EL layer 103b. This is possible. This is possible. This is possible. This is possible.

[0131] The charge generation layer 104 has translucency with respect to visible light from the viewpoint of light extraction efficiency. Specifically, Preferably, the visible light transmittance of the charge generation layer 104 is 40% or more. Also, even if the charge generation layer 104 has a lower conductivity than the first electrode 101 or the second electrode 102, it can still function.

[0132] FIG. 1(C) shows the stacked structure of the EL layer 103. In FIG. 1(C), when the first electrode 101 functions as an anode, the EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are sequentially stacked on the first electrode 101. Even when there are multiple EL layers as in the tandem structure shown in FIG. 1(B), as shown in FIG. 1(D), each EL layer has a structure in which they are sequentially stacked in the above manner from the anode side. When the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.

[0133] Regarding the configuration in which multiple EL layers are stacked, as shown in FIG. 1(E), the EL layers may be stacked in three layers (103a, 103b, 103c) via charge generation layers (104a, 104b) respectively. However, the number of stacked layers is not limited to two or three layers, and a configuration in which four or more layers are stacked may also be acceptable. Also, the light emitting layers (113, 113a, 113b, 113c) included in the EL layers (103, 103a, 103b, 103c) each have a light emitting substance and a plurality of substances appropriately combined, and can be configured to obtain fluorescence emission or phosphorescence emission presenting a desired emission color. Also, when there are multiple light emitting layers 113 (113a, 113b, 113c), the emission colors of each light emitting layer may be different. In this case, the light emitting substances and other substances used for each stacked light emitting layer are different from each other. Any material can be used. For example, the light-emitting layer 113a can be blue, the light-emitting layer 113b can be any of red, green, or yellow, and the light-emitting layer 113c can be blue. However, the light-emitting layer 113a can also be red, the light-emitting layer 113b can be any of blue, green, or yellow, and the light-emitting layer 113c can be red. In addition, considering the luminance and color characteristics of multiple emissions, other combinations of emission colors can be appropriately used.

[0134] Moreover, in the light-emitting element which is one aspect of the present invention, a configuration in which the light emitted from the EL layer (103, 103a, 103b) is resonated between both electrodes to enhance the obtained light is also good. For example, in FIG. 1(C), by using the first electrode 101 as a reflective electrode and the second electrode 10 2 as a semi-transmissive / semi-reflective electrode, a microcavity structure can be formed, and the light emitted from the EL layer 103 can be enhanced.

[0135] Note that when the first electrode 101 of the light-emitting element is a reflective electrode composed of a laminated structure of a conductive material having reflectivity and a conductive material having translucency (transparent conductive film), optical adjustment can be performed by controlling the film thickness of the transparent conductive film. Specifically, it is preferable to adjust so that the electrode distance between the first electrode 101 and the second electrode 102 is in the vicinity of mλ / 2 (where m is a natural number) with respect to the wavelength λ of the light obtained from the light-emitting layer 113. (However, m is a natural number).

[0136] In addition, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical distance from the first electrode 101 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained, and the optical distance from the second electrode 102 to the region (light-emitting region) where the desired light of the light-emitting layer 113 is obtained ​​​​​, adjust them so that they are each in the vicinity of (2m’ + 1)λ / 4 (where m’ is a natural number). is preferred. Here, the light-emitting region refers to the recombination region of holes and electrons in the light-emitting layer 113.

[0137] By performing such optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed, and light emission with good color purity can be obtained.

[0138] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 is strictly the total thickness from the reflection region in the first electrode 101 to the reflection region in the second electrode 102. This can be achieved. However, since it is difficult to precisely determine the reflection regions in the first electrode 101 and the second electrode 102, it is assumed that any positions of the first electrode 101 and the second electrode 102 are reflection regions, and the above-described effects can be sufficiently obtained. Also, the optical distance between the first electrode 101 and the light-emitting layer from which the desired light is obtained is strictly the optical distance between the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which the desired light is obtained. However, since it is difficult to precisely determine the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which the desired light is obtained, it is assumed that any position of the first electrode 101 is the reflection region and any position of the light-emitting layer from which the desired light is obtained is the light-emitting region, and the above-described effects can be sufficiently obtained. This can be achieved. However, since it is difficult to precisely determine the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which the desired light is obtained, it is assumed that any position of the first electrode 101 is the reflection region and any position of the light-emitting layer from which the desired light is obtained is the light-emitting region, and the above-described effects can be sufficiently obtained. Since it is difficult to precisely determine the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer from which the desired light is obtained, by assuming any position of the first electrode 101 as the reflection region and any position of the light-emitting layer from which the desired light is obtained as the light-emitting region, it is assumed that the above-described effects can be sufficiently obtained.

[0139] When the light-emitting element shown in Fig. 1(C) has a microcavity structure, even if the EL layer is common, light (monochromatic light) of different wavelengths can be extracted. Therefore, different emission colors can be obtained. ​Coloring (e.g., RGB) is not required, enabling high definition. Also, a combination with a coloring layer (color filter) is also possible. Further, since it is possible to enhance the forward emission intensity of a specific wavelength, power consumption can be reduced.

[0140] In the light-emitting element which is one aspect of the present invention described above, at least one of the first electrode 101 and the second electrode 102 is an electrode having translucency (such as a transparent electrode, a semi-transmissive / semi-reflective electrode, etc.). When the electrode having translucency is a transparent electrode, the transmittance of visible light of the transparent electrode is 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the reflectance of visible light of the semi-transmissive / semi-reflective electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. Also, these electrodes preferably have a resistivity of 1×10 -2 Ωcm or less.

[0141] In the light-emitting element which is one aspect of the present invention described above, when one of the first electrode 101 and the second electrode 102 is an electrode having reflectivity (reflective electrode), the reflectance of visible light of the electrode having reflectivity is 40% or more and 100% or less, preferably 70% or more and 100% or less. Also, this electrode preferably has a resistivity of 1×10 -2 Ωcm or less.

[0142] ≪Specific Structure and Fabrication Method of Light-Emitting Element≫ Next, the specific structure and fabrication method of the light-emitting element which is one aspect of the present invention will be described. In FIGS. 1(A) to 1(D), when the reference signs are common, the description will also be common.

[0143] <First Electrode and Second Electrode> As materials for forming the first electrode 101 and the second electrode 102, in the above-described element structure If the functions of both electrodes can be satisfied, the materials shown below can be used in appropriate combinations. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. Specifically, indium-tin oxide (also referred to as ITO), indium-silicon- tin oxide (also referred to as ITSO), indium-zinc oxide, indium-tungsten-zinc oxide can be mentioned. In addition, metals such as aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn ), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga) , zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum ( Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (A g), yttrium (Y), neodymium (Nd), etc., and alloys containing these in appropriate combinations can also be used. In addition, elements belonging to Group 1 or Group 2 of the periodic table not exemplified above (for example, lithium (Li), cesium (Cs), calcium (Ca ), strontium (Sr)), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these in appropriate combinations, and other materials such as graphene can be used. )

[0144] In the light-emitting element shown in FIG. 1, when the EL layer 103 having a laminated structure as shown in FIG. 1(C) is provided and the first electrode 101 is an anode, a hole injection layer 111 and a hole transport layer 112 of the EL layer 103 are sequentially laminated and formed on the first electrode 101 by a vacuum deposition method. Further, as shown in FIG. 1(D), a plurality of EL layers (103a, 103b) having a laminated structure are laminated with a charge generation layer 104 interposed therebetween. When the first electrode 101 is an anode, the EL layer 103 is formed on the first electrode 101. The hole injection layer 111a and the hole transport layer 112a of a are sequentially formed by vacuum evaporation only Moreover, after the EL layer 103a and the charge generation layer 104 are sequentially formed, on the charge generation layer 10 4, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are similarly sequentially formed Thereby.

[0145] <Hole injection layer and hole transport layer> The hole injection layer (111, 111a, 111b) is a layer that injects holes from the first electrode 101, which is an anode, and the charge generation layer (104) into the EL layer (103, 103a, 103b), and is a layer containing a material with high hole injection property. It is a layer containing a material with high hole injection property.

[0146] Examples of materials with high hole injection property include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide , tungsten oxide, and manganese oxide. In addition, phthalocyanine -based compounds such as phthalocyanine (abbreviation: H2Pc) and copper phthalocyanine (abbreviation: CuPc) can be used. That is, compounds such as phthalocyanine-based compounds can be used.

[0147] Also, low molecular weight compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methyl phenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4 '-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl ( abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N' -phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD) , 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] , 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)- N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6- bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl carbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9- phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCz PCN1) and other aromatic amine compounds can be used.

[0148] Also, a polymer compound (oligomer, dendrimer, polymer, etc.), poly(N-vinyl carbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: P VTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl} N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine (abbreviation: Poly-TPD) and the like can be used. Or, poly(3,4-ethylene dioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (abbreviation: PAni / PSS) and other acid-added polymer compounds can also be used.

[0149] Also, as a material with high hole injection property, a composite material containing a hole transport material and an acceptor material (electron-accepting material) can also be used. In this case, electrons are drawn from the hole transport material by the acceptor material, and holes are formed in the hole injection layer (111, 111a, 111b). layer (111, 111a, 111b). occurs, and holes are injected into the light-emitting layer (113, 113 a, 113b, 113c) through the hole transport layer (112, 112a, 112b). Note that the hole injection layer (111, 111a, 111b) may be formed as a single layer composed of a composite material containing a hole transporting material and an acceptor material (electron accepting material), or may be formed by laminating the hole transporting material and the acceptor material (electron accepting material) as separate layers. The hole transport layer (112, 112a, 112b) is a layer that transports holes injected from the first electrode 101 or the charge generation layer 104 to the light-emitting layer (11 3, 113a, 113b, 113c) by the hole injection layer (111, 111a, 111

[0150] b). Note that the hole transport layer (112, 112a, 112b) is a layer containing a hole transporting material. The hole transporting material used for the hole transport layer (112, 112 a, 112b) preferably has the same or a nearly the same HOMO level as that of the hole injection layer (111, 111a, 111 b). As the acceptor material used for the hole injection layer (111, 111a, 111b), metal oxides belonging to Groups 4 to 8 in the periodic table of elements can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide can be mentioned. Among them, molybdenum oxide is preferred because it is stable even in the air, has low hygroscopicity, and is easy to handle. In addition, organic acceptors such as quinodimethane derivatives, chloranil derivatives, and hexaazatriphenylene derivatives can be used. Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetra

[0151] is, periodic table of the elements in Group 4 to Group 8 metal oxides can be used. Specifically, is, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, rhenium oxide. Among them, in particular, molybdenum oxide is stable in the atmosphere, low hygroscopicity, easy to handle, so preferred. In addition, quinodimethane derivatives, chloranil derivatives, hexaazatriphenylene derivatives and other organic acceptors can be used. Specifically, 7,7,8,8 - tetracyano - 2,3,5,6 - tetra is, Trifluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,1 0,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation : HAT-CN), etc. can be used. In particular, a compound in which an electron-withdrawing group is bonded to a condensed aromatic ring having a plurality of heteroatoms, such as HAT-CN, is thermally stable and preferable. Also a [3]radialene derivative having an electron-withdrawing group (especially a halogen group such as a fluoro group or a cyano group) is preferable because of its very high electron-accepting property. Specifically, α,α’,α’’-1 ,2,3-cyclopropanetriylidene tris[4-cyano-2,3,5,6-tetrafluoro benzeneacetonitrile], α,α’,α’’-1,2,3-cyclopropanetriylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl) benzeneacetonitrile], α,α’,α’’-1,2,3-cyclopropanetriylidene tris[2,3,4,5,6-pentafluorobenzeneacetonitrile], etc. can be mentioned

[0152] As the hole-transporting material used for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 11 2b), a substance having a hole mobility of 1×10 -6 cm 2 / Vs or more is preferable. In addition, as long as the substance has higher hole transportability than electrons, other substances can be used

[0153] As the hole-transporting material, a hole-transporting material such as a π-electron-excessive heteroaromatic compound (for example, a compound having a carbazole skeleton or a compound having a furan skeleton) or a compound having an aromatic amine skeleton is preferable ​​​​​​​​

[0154] Specific examples of the hole transporting material include 4,4'-bis[N-(1-naphthyl)-N-phenyl amino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methyl phenyl)-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-f luoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl -3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPA FLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-di methyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL) , N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)dip enylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N- phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl -4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9 H-carbazole (abbreviation: PCPPn), N-(4-biphenyl)-N-(9,9-dime thyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-f (2-Enyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoro rene-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phen yl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP) , 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)tri phenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9 -phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB ), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazol-3-yl)-N ,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N' '-triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl) benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phe nyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene -2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-amine ( abbreviation: PCBASF), 2-[N-(9-phenylcarbazol-3-yl)-N-phe nylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-bis[N -(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-biflu orene (abbreviation: DPA2SF), N-[4-(9H-carbazol-9-yl)phenyl -N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-bis 4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethyl aromatic amine compounds such as fluorene-2,7-diamine (abbreviation: YGA2F) can be used In addition, 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H -carbazole (abbreviation: PCPN), 4,4',4''-tris(carbazol-9-yl yl)triphenylamine (abbreviation: TCTA), 4,4',4''-tris[N-(1-naph thyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4, 4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDA TA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino triphenylamine (abbreviation: m-MTDATA), N,N'-di(p-tolyl)-N, N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DP AB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N, N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD ), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino benzene (abbreviation: DPA3B) and other compounds having an aromatic amine skeleton, 1,3-bis( N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)bip enyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenyl carbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole )(Abbreviation: PCCP), 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis [N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis [N-(4-diphenylaminophenyl)-N-( 1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 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: PCzPCA 2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris [4- (N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl -9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), etc. carbazole skeleton-containing compounds, 4,4’,4’’-(benzene-1,3,5-triyl )tris(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl )phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), etc. thiophene skeleton-containing compounds, 4,4’,4’’-(benzene-1,3,5-triyl )tris(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl -9H-fluoren-9-yl)phenyl]dibenzofuran (abbreviation: DBFFLP-II), 4-[4-(9-phenyl-9H-fluoren-9-yl )phenyl]-6-phenyldibenzofuran (abbreviation: DBFFLP-IV), etc. dibenzofuran skeleton-containing compounds, 4,4’,4’’-(benzene-1,3,5-triyl )tris(10-phenylphenoxazine) (abbreviation: DPO3P-II), 4-[4-(9-phenyl-9H-fluoren-9-yl )phenyl]-6-phenyldibenzofuran (abbreviation: DPOFLP-IV), etc. phenoxazine skeleton-containing compounds, 4,4’,4’’-(benzene-1,3,5-triyl )tris(dibenzothiophene) (abbreviation: DBT3P-II), 4-{3-[3-(9-phenyl {[9H-fluoren-9-yl]phenyl}phenyl dibenzofuran (abbreviation: mmD) Compounds having a furan skeleton such as BFFLBi-II) can be mentioned.

[0155] Furthermore, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenyl amine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenyl amino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide]( abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis (phenyl)benzidine] (abbreviation: Poly-TPD) and other polymer compounds can also be used. It is also possible.

[0156] However, the hole transporting material is not limited to the above, and various known materials can be used alone or in combination of one or more as a hole transporting material for the hole injection layer (111, 111a, 111b) and the positive hole transporting layer (112, 112a, 112b). Note that the hole transporting layer (1 12, 112a, 112b) may be formed from a plurality of layers respectively. That is, for example the first hole transporting layer and the second hole transporting layer may be laminated.

[0157] In the light emitting device shown in Fig. 1(D), the light emitting layer 1 13a is formed on the hole transporting layer 112a of the EL layer 103a by vacuum evaporation. Also, after the EL layer 103a and the charge generation layer 104 are formed, the light emitting layer 113b is formed on the hole transporting layer 112b of the EL layer 103b by vacuum evaporation method.

[0158] <Light emitting layer> The light emitting layer (113, 113a, 113b, 113c) is a layer containing a light emitting substance. Note that As the light-emitting substance, substances exhibiting light emission colors such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red are appropriately used. Also, by using different light-emitting substances in a plurality of light-emitting layers (113a, 113b, 113c), a configuration that exhibits different light emission colors (for example, white light emission obtained by combining light emission colors in a complementary color relationship) can be achieved. Furthermore, one light-emitting layer may have a laminated structure having different light-emitting substances.

[0159] In addition to the light-emitting substance (guest material), the light-emitting layer (113, 113a, 113b, 113c) may have one or more organic compounds (host material, assist material). Also, as the one or more organic compounds, one or both of the hole-transporting material and the electron-transporting material described in this embodiment can be used.

[0160] The light-emitting substance that can be used in the light-emitting layer (113, 113a, 113b, 113c) is not particularly limited, and a light-emitting substance that converts singlet excitation energy into light emission in the visible light region or a light-emitting substance that converts triplet excitation energy into light emission in the visible light region can be used. Since the organic compound which is one aspect of the present invention exhibits fluorescence emission, it can be used as a light-emitting substance that converts singlet excitation energy into light emission in the visible light region. In addition, examples of the other light-emitting substances include the following.

[0161] Examples of the light-emitting substance that converts singlet excitation energy into light emission include substances that emit fluorescence (fluorescent materials), such as pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, and dibenzofuran derivatives. ​​​​​​​​​​​​​​, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. can be mentioned. In particular, pyrene derivatives are preferred because of their high fluorescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi (dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbre viation: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N '-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( (pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura n)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-di yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbre viation: 1,6BnfAPrn-03), etc. can be mentioned.

[0162] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-(Anthryl)biphenyl-4-yl]-2,2’-bipyridine (abbreviation: PAPP2B Py), N,N’-bis[4-(9H-carbazol-9-yl)phenyl]-N,N’ -diphenylstilbene-4,4’-diamine (abbreviation: YGA2S), 4-(9H-carb azol-9-yl)-4’-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4’-(9,10-di phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbaz ol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4 ’-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4’-(9- phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA ), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP ), N,N’’-(2-tert-butylanthracene-9,10-diyl-di-4,1- phenylene)bis[N,N’,N’-triphenyl-1,4-phenylenediamine](abbre viation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-a ntryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N -[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N’,N’-tri phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), etc. can be used .

[0163] In addition, examples of the luminescent material that converts triplet excitation energy into luminescence include substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (Thermally activated delayed fluorescence: TADF) materials that exhibit thermally activated delayed fluorescence. Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), rare earth metal complexes, and the like. Since these exhibit different emission colors (emission peaks) for each substance, they are appropriately selected and used as needed.

[0164] Examples of phosphorescent materials that exhibit blue or green and have a peak wavelength of the emission spectrum in the range of 450 nm or more and 570 nm or less include the following substances. For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium

[0165] (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir

[0166] (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl -4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrp (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl -4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrp tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl -4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5 btz)3]), and other organometallic complexes having a 4H-triazole skeleton, tris[3- methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato Iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl -5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(II I) (abbreviation: [Ir(Prptz1-Me)3]) and other organometallic complexes having a 1H-triazole skeleton, fac-tris[1-(2,6-diisopropylphenyl)-2-f enyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3 ), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f] phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3 ), and other organometallic complexes having an imidazole skeleton, bis[2-(4’,6’-diflu orophenyl)pyridinato-N,C iridium(III) tetrakis(1-pyrazo 2’ lyl)borate (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl)py ridinato-N,C iridium(III) picolinate (abbreviation: Firpic), bi 2’ s{2-[3’,5’-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’ }iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) 2’ iridium (III) acetylacetonate (abbreviation: FIr(acac)), and other organometallic complexes having an electron-withdrawing group and using a phenylpyridine derivative as a ligand are exemplified. Examples include organometallic complexes and the like.

[0167] Phosphorescent materials that exhibit green or yellow and have a peak wavelength of the emission spectrum in the range of 495 nm or more and 590 nm or less include the following substances. Examples of such substances are as follows.

[0168] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation : [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i ridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bi s(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl pyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-pheni lylpyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac) ), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN 3 phenyl-κC}iridium(III) (abbreviation : [Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( acac)]), organometallic complexes having a pyrimidine skeleton such as (acetylacetonato) bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [I r(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopro pyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(m Organometallic complexes having a pyrazine skeleton such as ppr-iPr)2(acac)]), tri s(2-phenylpyridinato-N,C 2’ )iridium(III) (abbreviation: [Ir(pp y)3]), bis(2-phenylpyridinato-N,C 2’ )iridium(III) acetyl acetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quin olinato)iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(ac ac)]), tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir( bzq)3]), tris(2-phenylquinolinato-N,C 2’ )iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C 2’ )irid ium(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]) such as organometallic complexes having a pyridine skeleton, bis(2,4-diphenyl-1,3-oxazolato -N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir(dpo)2 (acac)]), bis{2-[4’-(perfluorophenyl)phenyl]pyridinato -N,C 2’}iridium(III) acetylacetonate (abbreviation: [Ir(p-PF- ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2’ )irid ium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac)]) and other organometallic complexes, and rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium (III) (abbreviation: [Tb(acac)3(Phen)]) are exemplified. ​

[0169] Exhibiting yellow or red color, with the peak wavelength of the emission spectrum being 570 nm or more and 750 nm or less Examples of the phosphorescent material include the following substances.

[0170] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmeth anato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III )(abbreviation: [Ir(d1npm)2(dpm)]) and other organic metal complexes having a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridi um(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-fluoro phenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2( acac)]) and other organic metal complexes having a pyrazine skeleton, tris(1-phenylisoquinolinato-N,C )iridium(III) (abbreviation: [Ir(piq)3]), bis (1-phenylisoquinolinato-N,C )iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]) and other organic metal complexes having a pyridine skeleton, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-por phine, etc. 2’ )iridium(III) (abbreviation: [Ir(piq)3]), bis (1-phenylisoquinolinato-N,C 2’ )iridium(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]) and other organic metal complexes having a pyridine skeleton, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-por phine, etc. phine, etc.​ Platinum complexes such as rufirinplatinum(II) (abbreviation: [PtOEP]), tris(1,3- Diphenyl-1,3-propanedionato)(monophenanthroline)europium(II) I) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)-3 ,3,3-Trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]).

[0171] The organic compounds (host materials, The host material has an energy gap larger than that of the light-emitting material (guest material). One or more materials having a gap may be selected and used. The hole transporting materials mentioned above and the electron transporting materials described below are also usable. Such an organic compound (host material, assist material) can also be used. One example of organic compounds is that they have a low LUMO level and are therefore used as host materials or assist materials. This allows the driving voltage to be reduced. The relatively high T1 level mentioned above is also a desired characteristic. When used as one of the pairs forming an exciplex, it also has a LUMO approximation. Because of its low molecular weight, it can be combined with many other materials. This paper will explain in detail the properties required for such organic compounds (host materials, assist materials).

[0172] When the light-emitting substance is a fluorescent material, the host material has an energy level of 100 nm in the singlet excited state. It is preferable to use an organic compound having a large molecular weight and a small energy level in the triplet excited state. In addition to the hole-transporting material and the electron-transporting material shown in this embodiment, a bipolar material can be used as the host material, but any substance that satisfies the above conditions is more preferable. For example, anthracene derivatives and tetracene derivatives are also suitable.

[0173] Therefore, as the host material combined with the fluorescent light-emitting substance, for example, 9-phenyl- 3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation : PCzPA), PCPN, CzPA, 7-[4-(10-phenyl-9-anthryl) phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6- [3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1 ,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phen yl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: F LPPA), 5,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl )tetracene, etc. can be mentioned.

[0174] When the light-emitting substance is a phosphorescent material, as the host material, an organic compound having a triplet excitation energy larger than the triplet excitation energy of the light-emitting substance ( energy difference between the ground state and the triplet excited state) can be selected. In addition to the hole-transporting material and the electron-transporting material shown in this embodiment, a bipolar material can be used as the host material, but any substance that satisfies the above conditions is more preferable. For example, condensed polycyclic aromatic compounds such as anthracene derivatives, phenanthrene derivatives , pyrene derivatives, chrysene derivatives, dibenzo[g,p]chrysene derivatives, etc. are also suitable.

[0175] Therefore, as the host material to be combined with the phosphorescent light-emitting material, for example, 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, 9-(4-{4’-[N-phenyl-N-(N-phenyl-3-carbazolyl)]amino}phenyl)phenyl-10-phenylanthracene (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 6,12-dimethoxy-5,11-diphenylchrysene, N,N,N’,N’,N’’,N’’,N’’,N’’,N’’’-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), CzPA, 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9’-bianthryl (abbreviation: BANT), 9,9’-(stilbene-3,3’-diyl)diphenanthrene (abbreviation: DPNS), 9,9’-(stilbene-4,4’-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), etc. can be mentioned. enylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10- phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: Cz A1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DP hPA), YGAPA, PCAPA, 9-(4-{4’-[N-phenyl-N-(N-f enyl-3-carbazolyl)]amino}phenyl)phenyl-10-phenylanthracene ne (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9- diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 6,12-dime thoxy-5,11-diphenylchrysene, N,N,N’,N’,N’’,N’’,N’’ ’,N’’’-octaphenyldibenzo[g,p]chrysene-2,7,10,15-tet raamine (abbreviation: DBC1), CzPA, 3,6-diphenyl-9-[4-(10-f enyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9, 10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10 -di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10 -di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9’-bianthryl (abbreviation: BANT), 9,9’-(stilbene-3,3’-diyl)diphenanthrene( abbreviation: DPNS), 9,9’-(stilbene-4,4’-diyl)diphenanthrene (abbre viation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3) etc. are mentioned.

[0176] In addition, when a plurality of organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c), In this case, it is preferable to use a compound that forms an exciplex in combination with a phosphorescent material. With this structure, the energy transfer from the exciplex to the luminescent material, Ex Using TET (Exciplex-Triplet Energy Transfer) In this case, various organic compounds can be used in combination to obtain a desired light emission. However, in order to efficiently form an exciplex, it is necessary to use a compound that easily accepts holes (hole By combining a compound that easily accepts electrons (electron transport material) with a compound that easily accepts electrons (electron transport material) is particularly preferred.

[0177] TADF materials are materials that convert triplet excited states into singlet excited states using a small amount of thermal energy. It is possible to convert the light into a singlet state (reverse intersystem crossing), and efficiently emit light (fluorescence) from the singlet excited state. The conditions for efficiently obtaining thermally activated delayed fluorescence are as follows: The energy difference between the doublet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably In addition, the delayed fluorescence in TADF materials is The light is an emission that has a spectrum similar to that of normal fluorescence, but has a significantly longer lifespan. The lifespan of is 1×10 -6 sec or more, preferably 1×10 -3 More than seconds.

[0178] Examples of TADF materials include fullerenes and their derivatives, and acridines such as proflavine. Derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), cadmium (Cd) Cd, Sn, Pt, In, or Palladium Examples of the metal-containing porphyrin include those containing (Pd) and the like. Examples of the metal-containing porphyrin include for example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (abbreviation: SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me)), octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP), and the like.

[0179] Examples of other TADF materials include 2-(biphenyl-4-yl)-4,6-bis(12- phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3 -yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3, 5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-1 0-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ- TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)ph enyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT) , 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthene-9- one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroac 10-Phenyl-10H,1 0’H-spiro[acridine-9,9’-anthracene]-10’-one (abbreviation: ACR SA), and other heterocyclic compounds having a π-electron-excessive heterocyclic aromatic ring and a π-electron-deficient heterocyclic aromatic ring can be used. 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 the donor property of the π-electron-excessive heterocyclic aromatic ring and the acceptor property of the π-electron-deficient heterocyclic aromatic ring enhanced, and the energy difference between the singlet excited state and the triplet excited state becomes small,

[0180] so it is particularly preferable.

[0181] By appropriately using the above materials, a light-emitting layer (113, 113a, 113b, 113c) can be formed. Further, the above materials can be used to form a light-emitting layer (113, 113a, 113b, 113c) by combining them with low-molecular materials or high-molecular materials.

[0182] In the light-emitting device shown in FIG. 1(D), an electron transport layer 114a is formed on the light-emitting layer 113a of the EL layer 103a. Further, after the EL layer 103a and the charge generation layer 104 are formed, an electron transport layer 114b is formed on the light-emitting layer 113b of the EL layer 103b.

[0183] <Electron transport layer> The electron transport layer (114, 114a, 114b) is a layer that transports electrons injected from the second electrode 102 to the light-emitting layer (113, 113a, 11 3b, 113c) by the electron injection layer (115, 115a, 11 b). Note that the electron transport layer (114, 114a, 114b ​) is a layer containing an electron transporting material. The electron transporting layer (114, 114a, 114b) uses an electron transporting material preferably having an electron mobility of 1×10 -6 cm 2 / Vs or more. As long as it is a material with higher electron transportability than holes, other materials can be used for this purpose. The organic compound which is one aspect of the present invention satisfies such requirements. In addition, since the low level of the LUMO level leads to a reduction in the driving voltage, it is preferable to use the organic compound which is one aspect of the present invention for the electron transporting layer. Other usable materials are shown below. As the electron transporting material, in addition to metal complexes having a quinoline skeleton, metal complexes having a benzoquinoline skeleton, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc., oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives,

[0184] thiazole derivatives, phenanthroline derivatives, quinoline derivatives having a quinoline ligand, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyridine derivatives, bipyridine derivatives, pyrimidine derivatives, and other electron transporting materials such as π - electron - deficient heteroaromatic compounds containing nitrogen - containing heteroaromatic compounds can be used. Specific examples of the electron transporting material include tris(8 - quinolinolato)aluminum(III) (abbreviation: Alq3), tris(4 - methyl - 8 - quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10 - hydroxybenzo[h]quinolinato)beryllium( II)(abbreviation: BeBq2), bis(2 - methyl - 8 - quinolinolato)(4 - phenylph

[0185] (abbreviation: Alq3), tris(4 - methyl - 8 - quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10 - hydroxybenzo[h]quinolinato)beryllium( II)(abbreviation: BeBq2), bis(2 - methyl - 8 - quinolinolato)(4 - phenylph ​​Ehnolato aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) (abbreviation: Znq), etc. Metal complexes having a quinoline skeleton or a benzoquinoline skeleton , bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO ), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ ), bis[2-(2-hydroxyphenyl)benzothiazolato]zinc(II) (abbreviation: Z n(BTZ)2), etc. Metal complexes having an oxazole skeleton or a thiazole skeleton, etc. are exemplified thereof.

[0186] In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl )-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl) phenyl]-9H-carbazole (abbreviation: CO11), etc. Oxadiazole derivatives, 3- (4’-tert-butylphenyl)-4-phenyl-5-(4’’-biphenyl)-1 ,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4 -(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), etc. Triazole derivatives, 2,2’,2’’-(1,3,5-ben zentriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) , 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-ben zimidazole (abbreviation: mDBTBIm-II), etc. Imidazole derivatives (benzimid (including a zole derivative) or 4,4'-bis(5-methylbenzoxazol-2-yl) Oxazole derivatives such as stilbene (abbreviation: BzOS), bathophenanthroline (abbreviation : Bphen), bathocuproin (abbreviation: BCP), 2,9-bis(naphthalen-2- yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), etc. Phenanthroline derivatives such as 2-[3-(dibenzothiophen-4-yl)phenyl]di benzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(di benzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazol-9-yl )biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq ), 2-[4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl]dibenzo [f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzo thiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBT PDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzo [f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) and other quinoxaline derivatives or dibenzoquinoxaline derivatives, 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 pyridine derivatives, 4,6- bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP 2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl) )phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), etc. of pyrimidine derivatives, 2-{ 4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9 -yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzP Tzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phen yl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTz n-02), etc. of triazine derivatives can be used.

[0187] Also, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl fluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF- Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2' -bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) such as polymer compounds can be used. It can also be used.

[0188] Also, the electron transport layer (114, 114a, 114b) may not only be a single layer, but also a structure in which two or more layers composed of the above substances are laminated. It may be a structure in which two or more layers composed of the above substances are laminated.

[0189] Next, in the light-emitting element shown in Fig. 1(D), an electron injection layer 115a is formed on the electron transport layer 114a of the EL layer 103a by vacuum evaporation. Then, the EL layer 103a and the charge generation layer 104 are formed, and after being formed up to the electron transport layer 114b of the EL layer 103b, an electron injection layer 115b is formed on it by vacuum evaporation. After that, the EL layer 103a and the charge generation layer 104 are formed, and after being formed up to the electron transport layer 114b of the EL layer 103b, an electron injection layer 115b is formed on it by vacuum evaporation. After being formed up to the electron transport layer 114b of the EL layer 103b, an electron injection layer 115b is formed on it by vacuum evaporation. After being formed up to the electron transport layer 114b of the EL layer 103b, an electron injection layer 115b is formed on it by vacuum evaporation.

[0190] <Electron injection layer> The electron injection layer (115, 115a, 115b) is a layer containing a substance with high electron injection properties. For the electron injection layer (115, 115a, 115b), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiO x ) and the like such alkali metals, alkaline earth metals, or their compounds can be used. Also, rare earth metal compounds such as erbium fluoride (ErF3) can be used. Also, an electride may be used for the electron injection layer (115, 115a, 115b). Examples of electrides include substances obtained by adding electrons to a mixed oxide of calcium and aluminum at a high concentration. Note that the substances constituting the above-described electron transport layer (114, 114a, 114b) can also be used.

[0191] In addition, a composite material formed by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer (115, 115a, 115b). Since electrons are generated in the organic compound by such an electron donor, it is excellent in electron injection properties and electron transport properties. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, the electron transport materials (metal complexes, heteroaromatic compounds, etc.) used for the above-described electron transport layer (114, 114a, 114b) can be used. As the electron donor, any substance that shows electron-donating properties to the organic compound may be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Also, alkali metal oxides and alkaline earth earths Metal oxides are preferred, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, a Lewis base such as magnesium oxide can also be used. Also, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

[0192] In the light-emitting element shown in FIG. 1(D), when amplifying the light obtained from the light-emitting layer 113b, it is preferable that the optical distance between the second electrode 102 and the light-emitting layer 113b is less than 1 / 4 of the wavelength λ of the light exhibited by the light-emitting layer 113b. In this case, it can be adjusted by changing the film thickness of the electron transport layer 1 114b or the electron injection layer 115b.

[0193] <Charge generation layer> In the light-emitting element shown in FIG. 1(D), when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102, the charge generation layer 104 has a function of injecting electrons into the EL layer 103a and injecting holes into the EL layer 103b. Note that the charge generation layer 104 may have a structure in which an electron acceptor is added to a hole transport material, or a structure in which an electron donor is added to an electron transport material. Also, both of these structures may be laminated. By forming the charge generation layer 104 using the materials described above, it is possible to suppress an increase in the driving voltage when the EL layer is laminated.

[0194] In the charge generation layer 104, when the structure is such that an electron acceptor is added to a hole transport material, as the hole transport material, the materials shown in this embodiment can be used. Also, as the electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinone Examples include dimethane (abbreviation: F4-TCNQ), chloranil, etc. Further, oxides of metals belonging to Groups 4 to 8 in the periodic table can be mentioned. Specifically, in the periodic table, oxides of metals belonging to Groups 4 to 8 can be mentioned. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc. can be mentioned.

[0195] In the charge generation layer 104, when the structure is such that an electron donor is added to the electron transporting material, as the electron transporting material, the materials shown in this embodiment can be used. Further, as the electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or a metal belonging to Groups 2 and 13 in the periodic table and its oxides and carbonates can be used. Specifically, it is preferable to use lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate etc. Further, an organic compound such as tetrathianaphthacene may be used as the electron donor.

[0196] <Substrate> The light-emitting element shown in this embodiment can be formed on various substrates. Note that the type of the substrate is not limited to a specific one. As an example of the substrate, a semiconductor substrate (e.g., a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate , a metal substrate, a stainless steel substrate, a substrate having a stainless steel foil, a tantalum substrate, a substrate having a tungsten foil, a flexible substrate, a laminated film, paper containing a fibrous material, or a base film, etc. can be mentioned.

[0197] As an example of the glass substrate, barium borosilicate glass, aluminoborosilicate glass, or soda lime glass can be mentioned. Further, as an example of the flexible substrate, the laminated film, the base film, etc., polyethylene terephthalate (PET), polyethylene naphthalate (PEN), plastics typified by polyethersulfone (PES), synthetic resins such as acrylic resin, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor-deposited film, or papers can be mentioned.

[0198] In addition, for the production of the light-emitting element shown in this embodiment, a vacuum process such as a vapor deposition method or a solution process such as a spin coating method or an inkjet method can be used. When using the vapor deposition method, a physical vapor deposition method (PVD method) such as a sputtering method, an ion plating method, an ion beam vapor deposition method, a molecular beam vapor deposition method, a vacuum vapor deposition method, or a chemical vapor deposition method (CVD method) can be used. In particular, for the functional layers (hole injection layers (111, 111a, 111b), hole transport layers (112, 112a, 112b), light- emitting layers (113, 113a, 113b, 113c), electron transport layers (114, 114a, 114b), electron injection layers (115, 115a, 115b)), and charge generation layers (104, 104a, 104b) included in the EL layer of the light-

[0199] Note that the EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are configured by each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a , 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114 , 114a, 114b), electron injection layer (115, 115a, 115b)) or charge generation layer ( 104, 104a, 104b) are not limited to the materials described above, and other materials can be used in combination as long as they can satisfy the functions of each layer. As an example , a polymer compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (a compound in the intermediate region between low molecules and polymers: molecular weight 400 to 4000), an inorganic compound (quantum dot material , etc.) can be used. Further, as the quantum dot material, a colloidal quantum dot material, an alloy-type quantum dot material, a core-shell type quantum dot material, a core-type quantum dot material, etc. can be used.

[0200] The configuration shown in this embodiment can be used in appropriate combination with the configuration shown in other embodiments.

[0201] (Embodiment 3) In this embodiment, a light-emitting device which is one aspect of the present invention will be described. Note that the light-emitting device shown in Fig. 2(A) is an active matrix type light-emitting device in which a transistor (FET) 202 and a light-emitting element (2 03R, 203G, 203B, 203W) on the first substrate 201 are electrically connected, and a plurality of light-emitting elements (203R, 203G, 203B, 203W) have a common EL layer 204, and according to the emission color of each light-emitting element, between the electrodes of each light-emitting element ​ It has a microcavity structure with an adjusted optical distance. Also, the light emitted from the EL layer 204 is an injection top-emission type light-emitting device that is emitted through color filters (206R, 206G, 206 B) formed on the second substrate 205.

[0202] The light-emitting device shown in Fig. 2(A) is formed such that the first electrode 207 functions as a reflective electrode. Also, the second electrode 208 is formed so as to function as a semi-transmissive / semi-reflective electrode. Note that as the electrode materials for forming the first electrode 207 and the second electrode 208, other embodiments may be referred to and used as appropriate.

[0203] Also, in Fig. 2(A), for example, when the light-emitting element 203R is a red light-emitting element, the light-emitting element 203 G is a green light-emitting element, the light-emitting element 203B is a blue light-emitting element, and the light-emitting element 203W is a white light-emitting element as shown in Fig. 2(B), the light-emitting element 203R is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200R, and the light-emitting element 203G is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200G. The light-emitting element 2 03B is adjusted so that the optical distance between the first electrode 207 and the second electrode 208 is 200B. As shown in Fig. 2(B), in the light-emitting element 203R, the conductive layer 210R is stacked on the first electrode 207, and in the light-emitting element 203G, the conductive layer 210G is stacked, whereby optical adjustment can be performed. On the second substrate 205, color filters (206R, 206G, 206B) are formed. Note that the color filters pass a specific wavelength range of visible light and block a specific wavelength range.

[0204] block a specific wavelength range of visible light. It is a filter for blocking. Therefore, as shown in Fig. 2(A), by providing a color filter 206R that allows only the red wavelength range to pass through at a position overlapping the light-emitting element 203R, red light emission can be obtained from the light-emitting element 203R. Also, by providing a color filter 206G that allows only the green wavelength range to pass through at a position overlapping the light-emitting element 203G, green light emission can be obtained from the light-emitting element 203G. Further, by providing a color filter 206B that allows only the blue wavelength range to pass through at a position overlapping the light-emitting element 203B, blue light emission can be obtained from the light-emitting element 203B. However, for the light-emitting element 203W, white light emission can be obtained without providing a color filter. Note that a black layer (black matrix) 209 may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material. At the position overlapping the light-emitting element 203R, a color filter 206R that allows only the red wavelength range to pass through is provided, so that red light emission can be obtained from the light-emitting element 203R. Also, at the position overlapping the light-emitting element 203G, a color filter 206G that allows only the green wavelength range to pass through is provided, so that green light emission can be obtained from the light-emitting element 203G. At the position overlapping the light-emitting element 203G, a color filter 206G that allows only the green wavelength range to pass through is provided, so that green light emission can be obtained from the light-emitting element 203G. Also, at the position overlapping the light-emitting element 203B, a color filter 206B that allows only the blue wavelength range to pass through is provided, so that blue light emission can be obtained from the light-emitting element 203B. At the position overlapping the light-emitting element 203B, a color filter 206B that allows only the blue wavelength range to pass through is provided, so that blue light emission can be obtained from the light-emitting element 203B. However, for the light-emitting element 203W, white light emission can be obtained without providing a color filter. Note that a black layer (black matrix) 209 may be provided at the end of one type of color filter. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material. Furthermore, the color filters (206R, 206G, 206B) and the black layer 209 may be covered with an overcoat layer made of a transparent material. In Fig. 2(A), a light-emitting device having a structure (top emission type) for extracting light emission on the second substrate 205 side is shown. However, as shown in Fig. 2(C), it may also be a light-emitting device having a structure (bottom emission type) for extracting light on the first substrate 201 side where the FET 202 is formed. In the case of a bottom emission type light-emitting device, the first electrode 207 is formed to function as a semi-transmissive and semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. Also, for the first substrate 201, at least a light-transmissive substrate is used. Also, the color filters (206R’, 206G’, 206B’) may be provided on the first substrate 201 side rather than the light-emitting elements (203R, 203G, 203B) as shown in Fig. 2(C).

[0205] In Fig. 2(A), a light-emitting device having a structure (top emission type) for extracting light emission on the second substrate 205 side is shown. However, as shown in Fig. 2(C), it may also be a light-emitting device having a structure (bottom emission type) for extracting light on the first substrate 201 side where the FET 202 is formed. Note that in the case of a bottom emission type light-emitting device, the first electrode 207 is formed to function as a semi-transmissive and semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode. Also, for the first substrate 201, at least a light-transmissive substrate is used. Also, the color filters (206R’, 206G’, 206B’) may be provided on the first substrate 201 side rather than the light-emitting elements (203R, 203G, 203B) as shown in Fig. 2(C). In Fig. 2(A), a light-emitting device having a structure (top emission type) for extracting light emission on the second substrate 205 side is shown. However, as shown in Fig. 2(C), it may also be a light-emitting device having a structure (bottom emission type) for extracting light on the first substrate 201 side where the FET 202 is formed. Note that in the case of a bottom emission type light-emitting device, the first electrode 207 is formed to function as a semi-transmissive and semi-reflective electrode, and the second electrode 208 is formed to function as a reflective electrode.

[0206] Also, in FIG. 2(A), the light-emitting element is shown in the case of a red light-emitting element, a green light-emitting element, a blue light-emitting element, and a white light-emitting element. However, the light-emitting element according to one aspect of the present invention is not limited to its configuration, and may have a configuration having a yellow light-emitting element or an orange light-emitting element. Note that in order to fabricate these light-emitting elements, materials used for the EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer, etc.) may be appropriately used by referring to the descriptions of other embodiments. In that case, it is also necessary to appropriately select a color filter according to the emission color of the light-emitting element.

[0207] By adopting the above configuration, a light-emitting device including a light-emitting element exhibiting a plurality of emission colors can be obtained.

[0208] Note that the configuration shown in this embodiment can be appropriately combined with the configuration shown in other embodiments and used.

[0209] (Embodiment 4) In this embodiment, a light-emitting device according to one aspect of the present invention will be described.

[0210] By applying the element configuration of the light-emitting element according to one aspect of the present invention, an active matrix type light-emitting device or a passive matrix type light-emitting device can be fabricated. Note that an active matrix type light-emitting device has a configuration in which a light-emitting element and a transistor (FET) are combined. Therefore, both a passive matrix type light-emitting device and an active matrix type light-emitting device are included in one aspect of the present invention. Note that the light-emitting element described in other embodiments can be applied to the light-emitting device shown in this embodiment.

[0211] In this embodiment, an active matrix light-emitting device will be described with reference to FIG. 3.

[0212] Note that FIG. 3(A) is a top view showing the light-emitting device 21, and FIG. 3(B) is a cross-sectional view taken along the chain line A -A' in FIG. 3(A). The active matrix light-emitting device includes a pixel portion 302, a driving circuit portion (source line driving circuit) 303, and a driving circuit portion 1 provided on the first substrate 30, and a driving circuit portion (gate line driving circuit) (304a, 304b). The pixel portion 302 and the driving circuit portion (303, 304a, 304b) are sealed between the first substrate 301 and the second substrate 306 by a sealing material 305.

[0213] In addition, a routing wiring 307 is provided on the first substrate 301. The routing wiring 307 is electrically connected to an FPC 308 which is an external input terminal. Note that the FPC 308 transmits external signals (for example, video signals, clock signals, start signals, reset signals, etc.) and potentials to the driving circuit portions (303, 304a, 304b). In addition, a printed wiring board (PWB) may be attached to the FPC 308. Note that the state in which these FPCs and PWBs are attached is included in the light-emitting device.

[0214]

[0215] Next, the cross-sectional structure of the light-emitting device is shown in FIG. 3(B). The pixel portion 302 is formed by a plurality of pixels each having an FET (switching FET) 311, an FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312. Note that the number of FETs included in each pixel is not particularly limited and can be appropriately provided as needed. ​​

[0216] The FETs 309, 310, 311, and 312 are not particularly limited, and for example, transistors such as the staggered type and the inverse staggered type can be applied. Also, a transistor structure such as a top gate type or a bottom gate type may be used. Moreover, the FETs 309, 310, 311, and 312 are not particularly limited in terms of the crystallinity of the semiconductor that can be used for them, and any of an amorphous semiconductor, a semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a crystalline region in part) may be used. Note that it is preferable to use a semiconductor having crystallinity because deterioration of transistor characteristics can be suppressed.

[0217] Furthermore, as these semiconductors, for example, group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, etc. can be used. Typically, semiconductors containing silicon, semiconductors containing gallium arsenic, oxide semiconductors containing indium, etc. can be applied.

[0218]

[0219]

[0220] The drive circuit section 303 includes FET 309 and FET 310. Note that FET 309 and F ET 310 may be formed of a circuit including a unipolar (either N-type or P-type only) transistor, or may be formed of a CMOS circuit including an N-type transistor and a P-type transistor. Also, it may be configured to have a drive circuit externally.

[0220] The end portion of the first electrode 313 is covered with an insulator 314. Note that the insulator 314 includes organic compounds such as negative photosensitive resin and positive photosensitive resin (acrylic resin), and acids Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride can be used. It is preferred that the upper or lower end of the insulator 314 has a curved surface with curvature. This can improve the coating property of the film formed on the upper layer of the insulator 314. The upper or lower end of the insulator 314 preferably has a curved surface with curvature. This can improve the coating property of the film formed on the upper layer of the insulator 314. Thereby, the coating property of the film formed on the upper layer of the insulator 314 can be made good.

[0221] An EL layer 315 and a second electrode 316 are laminated and formed on the first electrode 313. The EL layer 315 includes a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. has.

[0222] Note that the configuration of the light-emitting element 317 shown in this embodiment can be applied to the configurations and materials described in other embodiments. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal. Note that the configuration of the light-emitting element 317 shown in this embodiment can be applied to the configurations and materials described in other embodiments. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal. is electrically connected to the FPC 308 which is an external input terminal.

[0223] Also, in the cross-sectional view shown in FIG. 3(B), only one light-emitting element 317 is shown, but in the pixel portion 3 02, a plurality of light-emitting elements are arranged in a matrix. In the pixel portion 30 2, light-emitting elements capable of obtaining three types (R, G, B) of light emission are selectively formed respectively, and a light-emitting device capable of full-color display can be formed. Also, in addition to the light-emitting elements capable of obtaining three types (R, G, B) of light emission, for example, light-emitting elements capable of obtaining light emission such as white (W), yellow (Y), magenta (M ) cyan (C), etc. may be formed. For example, by adding light-emitting elements capable of obtaining several types of light emission described above to the light-emitting elements capable of obtaining three types (R, G, B) of light emission, effects such as improvement of color purity and reduction of power consumption can be obtained. Also, it may be a light-emitting device capable of full-color display by combining with a color filter. Note that by combining with a color filter, it may be a light-emitting device capable of full-color display. Note that by adding light-emitting elements capable of obtaining several types of light emission described above to the light-emitting elements capable of obtaining three types (R, G, B) of light emission, effects such as improvement of color purity and reduction of power consumption can be obtained. Also, it may be a light-emitting device capable of full-color display by combining with a color filter. Note that by combining with a color filter, it may be a light-emitting device capable of full-color display. Note , As types of color filters, red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), etc. can be used. And so on.

[0224] The FETs (309, 310, 311, 312) and the light-emitting elements 317 on the first substrate 301 are bonded together by a sealing material 305 to bond the second substrate 306 and the first substrate 301. As a result, a structure is provided in a space 318 surrounded by the first substrate 301, the second substrate 306, and the sealing material 305. Note that the space 318 may be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealing material 305).

[0225] For the sealing material 305, an epoxy resin or glass frit can be used. Note that it is preferable to use a material that hardly permeates moisture and oxygen for the sealing material 305. Also, the second substrate 306 can be used in the same manner as those that can be used for the first substrate 301. Therefore, various substrates described in other embodiments can be used as appropriate. As the substrate, in addition to a glass substrate and a quartz substrate, a plastic substrate made of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, or acrylic resin can be used. When using glass frit as the sealing material, from the viewpoint of adhesiveness, the first substrate 301 and the second substrate 306 are preferably glass substrates.

[0226] As described above, an active matrix light-emitting device can be obtained.

[0227] Also, when forming an active matrix light-emitting device on a flexible substrate, on the flexible substrate An FET and a light-emitting element may be directly formed, or after forming an FET and a light-emitting element on another substrate having a release layer, the FET and the light-emitting element may be peeled off at the release layer by applying heat, force, laser irradiation, etc., and further transferred onto a flexible substrate for fabrication. As the release layer, for example, a laminate of inorganic films such as a tungsten film and a silicon oxide film, or an organic resin film such as polyimide can be used. As the flexible substrate, in addition to a substrate on which a transistor can be formed, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a cloth substrate (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or regenerated fibers (acetate, cupra, rayon, regenerated polyester), etc.), a leather substrate, or a rubber substrate can be mentioned. By using these substrates, excellent durability and heat resistance can be achieved, and weight reduction and thinning can be realized. Moreover, the configuration shown in this embodiment can be used by appropriately combining the configurations shown in other embodiments. (Embodiment 5) In this embodiment, an example of various electronic devices and automobiles completed by applying a light-emitting element which is one aspect of the present invention and a light-emitting device having a light-emitting element which is one aspect of the present invention will be described. Note that the light-emitting device can be mainly applied to the display section in the electronic devices described in this embodiment. The electronic device shown in FIGS. 4(A) to 4(C) includes a housing 7000, a display section 7001, a speaker 7003, an LED lamp 7004, and operation keys 7005 (power switch or operation switch

[0228]

[0229]

[0230] ​​​​​​​​​​​​​including), connection terminal 7006, sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity , rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage , power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays, etc.), microphone 7008, etc. can be included.

[0231] Figure 4(A) is a mobile computer, and in addition to the above-described components, it can have a switch 7009, a red external line port 7010, etc.

[0232] Figure 4(B) is a portable image playback device (e.g., a DVD playback device) equipped with a recording medium. In addition to the above-described components, it can have a second display unit 7002, a recording medium reading unit 7011, etc.

[0233] Figure 4(C) is a digital camera with a television receiving function. In addition to the above-described components, it can have an antenna 7014, a shutter button 7015, an imaging unit 7016, etc.

[0234] Figure 4(D) is a portable information terminal. The portable information terminal has a function of displaying information on three or more sides of the display unit 7001. Here, an example is shown where information 7052, information 7053, and information 7054 are respectively displayed on different sides. For example, the user can confirm the information 7053 displayed at a position where it can be observed from above the portable information terminal while the portable information terminal is stored in the breast pocket of the clothes. The user can also confirm the display without taking the portable information terminal out of the pocket and, for example, determine whether to answer a call.

[0235] Figure 4(E) is a portable information terminal (including a smartphone). On the housing 7000, there is a display unit 7 001. It can have operation keys 7005, etc. Note that the portable information terminal may have a speaker , connection terminals, sensors, etc. The portable information terminal can also display character and image information on its multiple surfaces. Here, an example of displaying three icons 7050 is shown . Information 7051 shown by a dashed rectangle can also be displayed on other surfaces of the display unit 7001 . As an example of the information 7051, there are notifications of incoming calls such as e-mail, SNS, and phone calls, titles of e-mail and SNS, sender names, dates, times, remaining battery levels, antenna reception strength, etc. Or, icons 7050 or the like may be displayed at the position where the information 7051 is displayed .

[0236] FIG. 4(F) shows a large television device (also referred to as a TV or television receiver), which can have a housing 7000, a display unit 7001, etc. Here, a configuration in which the housing 7000 is supported by a stand 7018 is shown . The operation of the television device can be performed by a separate remote control operation unit 7111, etc. Note that the display unit 7 001 may be provided with a touch sensor, and it may be operated by touching the display unit 7001 with a finger or the like . The remote control operation unit 7111 may have a display unit for displaying information output from the remote control operation unit 7111 . The operation keys or touch panel provided in the remote control operation unit 7111 can be used to operate the channel and volume, and the image displayed on the display unit 7001 can be operated .

[0237] The electronic devices shown in FIGS. 4(A) to 4(F) can have various functions. For example , functions of displaying various information (such as still images, moving images, text images) on the display unit, touch panel Functions such as displaying calendars, dates, or times, and various software (programs) The function of controlling processing by the wireless communication function, It has a function to connect to a data network, and a wireless communication function to transmit or receive various data. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. Furthermore, in an electronic device having a plurality of display units, One display section is used primarily to display image information, and the other display section is used primarily to display text information. Or, a function to display images that take parallax into account on multiple displays to create a stereoscopic image. Furthermore, in electronic devices having an image receiving unit, Functions for taking still images, shooting videos, and automatically or manually correcting captured images Function, function to save the captured image to a recording medium (external or built-in to the camera), function to save the captured image The display unit can have a function of displaying the above-mentioned information on the display unit. The functions that the electronic device shown in the figure can have are not limited to these, and the electronic device may have a variety of functions. can be done.

[0238] FIG. 4(G) shows a wristwatch-type mobile information terminal that can be used, for example, as a smart watch. This wristwatch-type mobile information terminal is made up of a housing 7000, a display unit 7001, and operation buttons. Tan 7022, 7023, Connection terminal 7024, Band 7025, Microphone 7026 The display unit 7001 has a curved display surface. This allows the display to be displayed along the curved display surface. For example, hands-free conversation is possible by communicating with a wireless headset. Yes. The connection terminal 7024 can perform data transmission with other information terminals and also perform charging. The charging operation can also be performed by wireless power supply.

[0239] The display unit 7001 mounted on the housing 7000 that also serves as the bezel portion has a non-rectangular display area. The display unit 7001 can display an icon 7027 representing time, other icons 702 8, etc. Further, the display unit 7001 may be a touch panel (input / output device) equipped with a touch sensor (input device).

[0240] Note that the smartwatch shown in FIG. 4(G) can have various functions. For example, it has a function of displaying various information (such as still images, moving images, text images, etc.) on the display unit, a touch panel function, a function of displaying a calendar, date, or time, etc., a function of controlling processing by various software (programs), a wireless communication function, a function of connecting to various computer networks using the wireless communication function, a function of transmitting or receiving various data using the wireless communication function, a function of reading a program or data recorded on a recording medium and displaying it on the display unit, etc.

[0241] Also, inside the housing 7000, there can be a speaker, a sensor (including functions for measuring force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, current, voltage, electric power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays), a microphone, etc.

[0242] Note that the light-emitting device which is one aspect of the present invention and the display having the light-emitting element which is one aspect of the present invention​​​​ The device can be used for each display portion of the electronic device shown in this embodiment, and has a long life. This can be achieved.

[0243] In addition, as an electronic device to which a light-emitting device is applied, a folding type electronic device as shown in FIG. FIG. 5A shows a portable information terminal 93 in an unfolded state. 10. Also, FIG. 5(B) shows the state of the unfolded or folded state. FIG. 5C shows the mobile information terminal 9310 in the process of changing to the folded state. The portable information terminal 9310 in a folded state is shown. The portable information terminal 9310 in a folded state is shown. When unfolded, it has excellent portability, and when unfolded, it has a seamless, wide display area that allows for easy viewing of the display. Excellent.

[0244] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). The display unit 9311 may be connected to two housings via a hinge 9313. By bending the gap between the terminals 9315, the portable information terminal 9310 can be folded from the unfolded state. The light-emitting device of one embodiment of the present invention can be reversibly transformed into a display state. The display portion 9311 can be used as a display unit. In addition, a long-life electronic device can be realized. The display area 9312 in FIG. 1 is located on the side of the portable information terminal 9310 in the folded state. The display area 9312 displays information icons and frequently used apps and programs. You can display shortcuts to programs, check information, and launch apps. It can be done smoothly.

[0245] In addition, an automobile to which the light-emitting device is applied is shown in FIGS. 6(A) and 6(B). That is, the light-emitting device can be provided integrally with the automobile. Specifically, for the automobile shown in FIG. 6(A), the outer lights 5101 (including the rear part of the vehicle body), the wheels 5102 of the tires, and the doors 5103 can be applied to a part or the whole thereof. Further, for the interior display part 5104, the steering wheel 5105, the shift lever 5106, the seat 5107, the inner rearview mirror 5108, etc. shown in FIG. 6(B) of the automobile can be applied. In addition, it may be applied to a part of the glass window.

[0246] As described above, an electronic device or an automobile to which the light-emitting device or the display device according to one aspect of the present invention is applied can be obtained. In that case, a long-life electronic device can be realized. Note that the applicable electronic devices and automobiles are not limited to those shown in this embodiment, and can be applied in any field.

[0247] Note that the configuration shown in this embodiment can be used in appropriate combination with the configuration shown in other embodiments.

[0248] (Embodiment 6) In this embodiment, the configuration of a lighting device manufactured by applying the light-emitting device which is one aspect of the present invention, or a light-emitting element which is a part thereof

[0249] will be described with reference to FIG. 7. FIGS. 7(A) and 7(B) show an example of a cross-sectional view of the lighting device. Note that FIG. 7(A) is a bottom emission type lighting device that emits light from the substrate side, and FIG.

[0250] The lighting device 4000 shown in Fig. 7(A) has a light-emitting element 4002 on a substrate 4001. Also, it has a substrate 4003 with irregularities on the outside of the substrate 4001. The light-emitting element 4002 has a first electrode 4004, an EL layer 4005, and a second electrode 4006.

[0251] The first electrode 4004 is electrically connected to an electrode 4007, and the second electrode 4006 is electrically connected to an electrode 4 008. Also, an auxiliary wiring 4009 electrically connected to the first electrode 4004 may be provided. An insulating layer 4010 is formed on the auxiliary wiring 4009.

[0252] Also, the substrate 4001 and the sealing substrate 4011 are adhered with a sealing material 4012. Also, it is preferable that a desiccant 4013 is provided between the sealing substrate 4011 and the light-emitting element 4002. Since the substrate 4003 has irregularities as shown in Fig. 7(A), the extraction efficiency of the light generated by the light-emitting element 40 02 can be improved.

[0253] The lighting device 4200 in Fig. 7(B) has a light-emitting element 4202 on a substrate 4201. The light-emitting element 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206.

[0254] The first electrode 4204 is electrically connected to an electrode 4207, and the second electrode 4206 is electrically connected to an electrode 4 208. Also, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. Also, an insulating layer 4210 may be provided below the auxiliary wiring 4209.

[0255] The substrate 4201 and the sealing substrate 4211 with irregularities are adhered with a sealing material 4212. Also, A barrier film 4213 and a planarizing film 4214 may be provided between the sealing substrate 4211 and the light-emitting element 4202. Since the sealing substrate 4211 has irregularities as shown in Fig. 7(B), the extraction efficiency of the light generated by the light-emitting element 4202 can be improved.

[0256] In addition, as an application example of these lighting devices, a ceiling light for indoor lighting can be cited. Ceiling lights include surface-mounted ceiling types and recessed ceiling types. Such lighting devices are configured by combining a light-emitting device with a housing or a cover.

[0257] In addition, it can also be applied to a footlight that irradiates the floor surface to enhance the safety of the feet. A footlight is effective, for example, in a bedroom, on a staircase, or in a passageway. In that case, the size and shape can be appropriately changed according to the size and structure of the room. It is also possible to form a stationary lighting device configured by combining a light-emitting device and a support base.

[0258] It can also be applied as a sheet-shaped lighting device (sheet-shaped lighting). Since the sheet-shaped lighting is attached to a wall surface for use, it can be used for a wide range of applications without taking up much space. In addition, it is easy to increase the area. It can also be used for a wall surface or a housing having a curved surface.

[0259] In addition to the above, a light-emitting device according to one aspect of the present invention, or a light-emitting element which is a part thereof, can be applied to a part of furniture provided indoors to form a lighting device having a function as furniture.

[0260] As described above, various lighting devices to which the light-emitting device is applied can be obtained. These lighting devices ​​​​​​​​is included in one aspect of the present invention.

[0261] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible. EXAMPLES

[0262] <Synthesis Example 1> In this example, an organic compound represented by structural formula (100) in Embodiment 1, which is one embodiment of the present invention, is used. Compound, 13-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h][ 1) Synthesis of benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq) The method is explained below. The structure of 13mDBtPBfdbq is shown below.

[0263] [ka]

[0264] <Step 1: 1,4-Dihydrophenanthro[9,10-b]pyrazine-2,3-di ... Synthesis of 5.97 g of phenanthrene-9,10-diamine hydrochloride and 16.51 g of sodium bicarbonate g, 230 mL of diethyl oxalate was placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was filled with nitrogen. The mixture was then stirred at 130°C for 23 hours to react. 1 L of water was added to the mixture and stirred at room temperature for 30 minutes. The desired pyrazine derivative was obtained by washing with methanol (ochre powder, yield 3.91 g). The synthesis scheme of step 1 is shown in the following formula (a-1).

[0265] [ka]

[0266] <Step 2: Synthesis of 2,3-dichlorodibenzo[f,h]quinoxaline> Next, 3.91 g of 1,4-dihydrophenanthro[9,10-b]pyrazine-2,3-dione obtained in Step 1 above and 60 mL of dehydrated DMF were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. After the flask was cooled in ice, 5.4 mL of phosphoryl chloride was added, and the mixture was stirred at 100 °C for 7.5 hours. After a predetermined time had elapsed, the resulting mixture was poured into 130 mL of 1 M aqueous sodium hydroxide solution and then suction filtered. The obtained solid was washed with water and ethanol and then dissolved in toluene and filtered through celite. By concentrating the obtained filtrate, the target quinoxaline derivative was obtained (yellowish-white powder, yield 1.00 g, yield 22%). The synthesis scheme of Step 2 is shown in the following formula (a-2). -2,3-dione and 60 mL of dehydrated DMF were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. After the flask was cooled in ice, 5.4 mL of phosphoryl chloride was added, and the mixture was stirred at 100 °C for 7.5 hours. The inside of the flask was purged with nitrogen. After the flask was cooled in ice, 5.4 mL of phosphoryl chloride was added, and the mixture was stirred at 100 °C for 7.5 hours. After a predetermined time had elapsed, the resulting mixture was poured into 130 mL of 1 M aqueous sodium hydroxide solution and then suction filtered. The obtained solid was washed with water and ethanol and then dissolved in toluene and filtered through celite. By concentrating the obtained filtrate, the target quinoxaline derivative was obtained (yellowish-white powder, yield 1.00 g, yield 22%). The synthesis scheme of Step 2 is shown in the following formula (a-2). The synthesis scheme of Step 2 is shown in the following formula (a-2).

[0267]

Chemical formula

[0268] <Step 3: Synthesis of 2-chloro-3-(5-chloro-2-methoxyphenyl)quinoxaline> Synthesis> Next, 1.85 g of 2,3-dichlorodibenzo[f,h]quinoxaline obtained in Step 2 above, 1.16 g of 5-chloro-2-methoxyphenylboronic acid, 0.66 g of sodium carbonate, 27 mL of ethylene glycol dimethyl ether (abbreviation: DME), and 27 mL of water were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. After stirring and degassing the inside of the flask under reduced pressure, 0.48 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added, and the mixture was stirred at 100 °C for 20.5 hours to cause a reaction. After a predetermined time had elapsed, 1.85 g of 2,3-dichlorodibenzo[f,h]quinoxaline, 1.16 g of 5-chloro-2-methoxyphenylboronic acid, 0.66 g of sodium carbonate, 27 mL of ethylene glycol dimethyl ether (abbreviation: DME), and 27 mL of water were placed in a three-necked flask equipped with a reflux tube, and the inside was purged with nitrogen. After stirring and degassing the inside of the flask under reduced pressure, 0.48 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added, and the mixture was stirred at 100 °C for 20.5 hours to cause a reaction. The inside of the flask was purged with nitrogen. After stirring and degassing the inside of the flask under reduced pressure, 0.48 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added, and the mixture was stirred at 100 °C for 20.5 hours to cause a reaction. After a predetermined time had elapsed, 0.48 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added, and the mixture was stirred at 100 °C for 20.5 hours to cause a reaction. After that, water was added thereto, and the solid obtained by suction filtration was dissolved in dichloromethane and filtered. The filtrate was concentrated. The obtained solid was purified by silica gel column chromatography using toluene:hexane = 1:2 as the developing solvent to obtain the target quinoxaline derivative ([[]]END]] white powder, yield 1.86 g, yield 74%). The synthesis scheme of Step 3 is shown in the following formula (a-3 ).

[0269]

Chemical formula

[0270] <Step 4: Synthesis of 2-chloro-3-(5-chloro-2-hydroxyphenyl)quinoxaline > Next, 2.56 g of 2-chloro-3-(5-chloro-2-methoxyphenyl) quinoxaline obtained in Step 3 above and 70 mL of dehydrated dichloromethane were placed in a three-necked flask, and the inside was purged with nitrogen. After cooling the flask to -20 °C, 13 mL of boron tribromide (1 M dichloromethane solution ) was added dropwise, and the mixture was stirred at room temperature for 16 hours. After a predetermined time had elapsed, water was added, and extraction with dichloromethane was carried out. The solid obtained by the operation was purified by silica gel column chromatography using dichloromethane as the developing solvent to obtain the target quinoxaline derivative (yellow powder, yield 2.12 g, yield 84%). The synthesis scheme of Step 4 is shown in the following formula (a -4).

[0271]

Chemical formula

[0272] <Step 5: Synthesis of 13-chlorodibenzo[f,h][1]benzofuro[2,3-b]quinoxaline > Next, 2-chloro-3-(5-chloro-2-hydroxyphenyl) quinoxaline (2.12 g) obtained in Step 4 above , and 27 mL of dehydrated N-methyl-2-pyrrolidone (abbreviation: NMP) were placed in a three-necked flask equipped with a reflux condenser, and the inside was purged with nitrogen. 1.5 1 g of potassium carbonate was added, and the mixture was stirred at 120 °C for 8 hours. After a predetermined time elapsed, water was added, and the resulting mixture was suction filtered. The obtained solid was washed with ethanol to obtain the target quinoxaline derivative (pale yellow powder, yield 1.56 g, yield 84%). The synthesis scheme of Step 5 is shown in the following formula (a-5). is shown in the following formula (a-5).

[0273]

Chemical formula

[0274] <Step 6: Synthesis of 13-[3-(dibenzothiophen-4-yl)phenyl]dibenzof ,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq ) Furthermore, 0.78 g of 13-chlorodibenzof[h][1]benzofuro[2,3-b]quinoxaline obtained in Step 5 above, 1.10 g of (dibenzothiophen-4-yl)phenyl-3-boronic acid, 1.26 g of cesium fluoride, and 44 mL of mesitylene were placed in a three-necked flask equipped with a reflux condenser, and the inside was purged with nitrogen. The inside of the flask was degassed by stirring under reduced pressure and then 0.075 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba) 3) and 0.059 g of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added, and the mixture was stirred at 120 °C for 17.5 hours. After a predetermined time elapsed, the resulting mixture was obtained 3), and 0.059 g of 2'-(dicyclohexylphosphino)acetophenone ethylene ketal were added, and the mixture was stirred at 120 °C for 17.5 hours. After a predetermined time elapsed, the resulting mixture Ethanol was added to the compound, and the mixture was suction filtered and washed with water and ethanol. The obtained solid was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). It was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). It was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). It was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). It was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). It was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). It was dissolved in toluene and filtered through a filter aid composed of celite, alumina, and celite stacked in that order. After concentration to dryness, the target product was obtained by recrystallization from toluene (yellowish-white powder, yield 0.71 g, yield 56%). 0.70 g of the obtained yellowish-white powder was sublimation purified by the train sublimation method. The sublimation purification conditions were as follows: at a pressure of 2.7 Pa, while flowing argon gas at a flow rate of 10.5 mL / min, the solid was heated at 330 °C. After sublimation purification, the yellowish-white solid of the target product was obtained with a yield of 0.56 g and a yield of 80%. The synthesis scheme of Step 6 is shown in the following formula (a-6). ) is shown below.

[0275]

Chemical formula

[0276] The analysis results of the yellowish-white solid obtained in Step 6 above by nuclear magnetic resonance spectroscopy (1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 8. From these results, in this example, it was found that the organic compound, which is one aspect of the present invention represented by the above structural formula (100), 13mD BtPBfdbq was obtained. 1 The analysis results of the yellowish-white solid obtained in Step 6 above by nuclear magnetic resonance spectroscopy (1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 8. From these results, in this example, it was found that the organic compound, which is one aspect of the present invention represented by the above structural formula (100), 13mD BtPBfdbq was obtained. The analysis results of the yellowish-white solid obtained in Step 6 above by nuclear magnetic resonance spectroscopy (1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 8. From these results, in this example, it was found that the organic compound, which is one aspect of the present invention represented by the above structural formula (100), 13mD BtPBfdbq was obtained. 1 The analysis results of the yellowish-white solid obtained in Step 6 above by nuclear magnetic resonance spectroscopy (1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 8. From these results, in this example, it was found that the organic compound, which is one aspect of the present invention represented by the above structural formula (100), 13mD BtPBfdbq was obtained. The analysis results of the yellowish-white solid obtained in Step 6 above by nuclear magnetic resonance spectroscopy (1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 8. From these results, in this example, it was found that the organic compound, which is one aspect of the present invention represented by the above structural formula (100), 13mD BtPBfdbq was obtained. The analysis results of the yellowish-white solid obtained in Step 6 above by nuclear magnetic resonance spectroscopy (1H-NMR) are shown below. Also, the 1H-NMR chart is shown in Figure 8. From these results, in this example, it was found that the organic compound, which is one aspect of the present invention represented by the above structural formula (100), 13mD BtPBfdbq was obtained.

[0277] 1 1H-NMR.δ(CDCl3):7.49-7.51(m,2H),7.63-7.64(m,2H),7.71(t,1H),7.80-7.89(m,8H),8.06(d,1H),8.16(s,1H),8.22-8.25(m,2H),8.70-8.74(m,3H),9.36(d,1H),9.49-9.51(m,1H). 1H-NMR.δ(CDCl3):7.49-7.51(m,2H),7.63-7.64(m,2H),7.71(t,1H),7.80-7.89(m,8H),8.06(d,1H),8.16(s,1H),8.22-8.25(m,2H),8.70-8.74(m,3H),9.36(d,1H),9.49-9.51(m,1H). 1H-NMR.δ(CDCl3):7.49-7.51(m,2H),7.63-7.64(m,2H),7.71(t,1H),7.80-7.89(m,8H),8.06(d,1H),8.16(s,1H),8.22-8.25(m,2H),8.70-8.74(m,3H),9.36(d,1H),9.49-9.51(m,1H). 1H-NMR.δ(CDCl3):7.49-7.51(m,2H),7.63-7.64(m,2H),7.71(t,1H),7.80-7.89(m,8H),8.06(d,1H),8.16(s,1H),8.22-8.25(m,2H),8.70-8.74(m,3H),9.36(d,1H),9.49-9.51(m,1H).

[0278] Next, the ultraviolet-visible absorption spectra and emission spectra of the toluene solution and solid thin film of 13mDBtPBfdbq (hereinafter simply referred to as "absorption spectra") were measured.

[0279] For the measurement of the absorption spectrum in the toluene solution, an ultraviolet-visible spectrophotometer (model V550, manufactured by JASCO Corporation) was used. Also, for the measurement of the emission spectrum in the toluene solution, a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.) was used. The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown in Fig. 9(A). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0280] From the results in Fig. 9(A), in the toluene solution of 13mDBtPBfdbq, absorption peaks were observed at around 281 nm and 397 nm, and an emission wavelength peak was observed at around 405 nm (excitation wavelength 372 nm).

[0281] For the measurement of the absorption spectrum of the solid thin film, a solid thin film prepared by vacuum evaporation on a quartz substrate was used, and measured using an ultraviolet-visible spectrophotometer (U4100 model, manufactured by Hitachi High-Technologies Corporation). Also, for the measurement of the emission spectrum of the solid thin film, the same solid thin film as above was used, and measured using a fluorescence photometer (FS920, manufactured by Hamamatsu Photonics K.K.). The measurement results of the absorption spectrum and emission spectrum of the obtained solid thin film are shown in Fig. 9(B). The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0282] From the results in Fig. 9(B), in the solid thin film of 13mDBtPBfdbq, absorption peaks were observed at around 383 nm and 403 nm, and an emission wavelength peak was observed at around 511 nm (excitation wavelength 380 nm).

[0283] In addition, differential scanning calorimetry was performed on 13mDBtPBfdbq. The measurement was performed using a measuring device (Pyris 1, manufactured by PerkinElmer Japan Co., Ltd.). The temperature was raised from 10°C to 350°C at a rate of 40°C / min, and then held at 350°C for 1 minute. After that, the temperature was lowered from 350°C to -10°C at a rate of 100°C / min. This was counted as one cycle. In this example, three cycles were measured. The glass transition temperature (Tg) was 141°C from the results of the second heating cycle. Therefore, 13mDBtPBfdbq synthesized in this example is very heat-resistant. It was found to be an excellent material. EXAMPLES

[0284] In this embodiment, the 13-[3- (Dibenzothiophene-4-yl)phenyl]dibenzo[f,h][1]benzofuro[2 ,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq) (structural formula (100)) was developed. The light-emitting element 1 used in the optical layer and the light-emitting element for comparison were 2-[3-(3'-dibenzyl) 2-benzothiophene-4-yl)biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2m Regarding comparative light-emitting element 2, which uses DBTBPDBq-II) (structural formula (200)) in the light-emitting layer, The device structure, the manufacturing method, and the characteristics will be described below. The element structure is shown in FIG. 10, and the specific configuration is shown in Table 1. The chemical formula of the material used is shown below:

[0285] [Table 1]

[0286] [Chemical]

[0287] ≪Fabrication of Light-Emitting Element≫ The light-emitting element shown in this example has a structure in which a first electrode 9 is formed on a substrate 900 as shown in Fig. 10. On 01, a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914, and an electron injection layer 915 are sequentially laminated, and a second electrode 903 is laminated on the electron injection layer 915. It has.

[0288] First, a first electrode 901 was formed on the substrate 900. The electrode area was 4 mm 2 (2 mm × 2 mm). Also, a glass substrate was used for the substrate 900. The first electrode 901 was formed by sputtering indium tin oxide (ITSO) containing silicon oxide to a film thickness of 70 nm .

[0289] Here, as a pretreatment, the surface of the substrate was washed with water, baked at 200 °C for 1 hour, and then UV ozone treatment was performed for 370 seconds. Then, 10 -4 Pa or less, the substrate was introduced into a vacuum evaporation apparatus with the inside evacuated, and in the heating chamber of the vacuum evaporation apparatus, vacuum baking was performed at 170 °C for 30 minutes . After that, the substrate was allowed to cool for about 30 minutes. It was performed and then the substrate was allowed to cool for about 30 minutes.

[0290] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was vacuum evaporated The pressure in the apparatus was reduced to 1 × 10 -4 Pa, and then 4,4’,4’’-(benzene-1,3,5 -triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide with DBT3P-II: molybdenum oxide = 2:1 (mass ratio) and a film thickness of 70 nm, formed by co-evaporation. formed by co-evaporation to have a film thickness of 70 nm.

[0291] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was formed by evaporation using 4,4 '-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenyl lamine (abbreviation: PCBBi1BP) to have a film thickness of 20 nm. formed by evaporation to have a film thickness of 20 nm.

[0292] Next, a light-emitting layer 913 was formed on the hole transport layer 912.

[0293] In the case of the light-emitting element 1, the light-emitting layer 913 used, as a host material, an organic compound which is an aspect of the present invention, 13mDBtPBfdbq, and as an assist material, PCBBiF, and as a guest material ( phosphorescent material), bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl- κC](2,4-pentanedionato-κ O,O')iridium(III) (abbreviation: [I 2 r(dmpqn)2(acac)]), and was co-evaporated so that the weight ratio was 13mDBtPBfdbq:PC BBiF:[Ir(dmpqn)2(acac)] = 0.75:0.25:0.1. The film thickness was 40 nm. BBiF:[Ir(dmpqn)2(acac)] = 0.75:0.25:0.1. formed by co-evaporation. The film thickness was 40 nm.

[0294] In the case of the comparative light-emitting element 2, the light-emitting layer 913 used, as a host material, 2mDBTBPDBq-I I, and as an assist material, PCBBiF, and as a guest material (phosphorescent material), [Ir(d mpqn)2(acac)], and was co-evaporated so that the weight ratio was 2mDBTBPDBq-II:PCBBi F:[Ir(dmpqn)2(acac)] = 0.75:0.25:0.1. formed by co-evaporation. The film thickness was 40 nm.

[0295] Next, an electron transport layer 914 was formed on the light-emitting layer 913. The electron transport layer 914 is 9-[3- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl carbazole (abbreviation: mPCCzPTzn-02) with a film thickness of 3 0 nm and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phen anthroline (abbreviation: NBphen) were sequentially deposited so that the film thickness became 15 nm to form it.

[0296] Next, an electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was formed by depositing lithium fluoride (LiF) so that the film thickness became 1 nm.

[0297] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was formed of aluminum by vapor deposition so that the film thickness became 200 nm. In this example, the second electrode 903 functions as a cathode.

[0298] Through the above steps, a light-emitting element in which an EL layer is sandwiched between a pair of electrodes was formed on the substrate 900. Note that the hole injection layer 911, the hole transport layer 912, the light-emitting layer 913, the electron transport layer 914, and the electron injection layer 915 described in the above steps are functional layers constituting the EL layer in one aspect of the present invention. Also, in the vapor deposition process in the manufacturing method described above, all vapor deposition methods using the resistance heating method were used.

[0299] Also, the light-emitting element manufactured as described above is sealed with another substrate (not shown). Note that when sealing with another substrate (not shown), it is performed in a glove box under a nitrogen atmosphere. Next, another substrate (not shown) coated with a sealant that cures by ultraviolet light was placed on substrate 900. The substrates were fixed such that the sealant adhered to the periphery of the light-emitting element formed on substrate 900. At the time of sealing, ultraviolet light with a wavelength of 365 nm was irradiated at 6 J / cm². 2 to cure the sealant, and the sealant was stabilized by heat treatment at 80 °C for 1 hour.

[0300] ≪Operating Characteristics of Light-Emitting Element≫ The operating characteristics of each fabricated light-emitting element were measured. The measurements were performed at room temperature (in an atmosphere maintained at 25 °C). The results are shown in FIGS. 11 to 14.

[0301] The following Table 2 shows the main initial characteristic values of each light-emitting element near 1000 cd / m². 2

[0302]

Table 2

[0303] In the above results, it can be seen that the light-emitting element 1 fabricated in this example exhibits better current-voltage characteristics than the comparative light-emitting element 2. This is because 13mDBtPBfdbq, which is one aspect of the present invention used in the light-emitting layer of the light-emitting element 1, has a deep LUMO level due to its structure fused with a five-membered ring having oxygen. Based on the results of cyclic voltammetry (CV) reduction potential measurements, the LUMO level of 2mDBTBPDBq-II was -2.94 eV, whereas the LUMO level of 13mDBtPBfdbq was -3.17 eV.

[0304] Also, a current was passed through the light-emitting element 1 and the comparative light-emitting element 2 at a current density of 2.5 mA / cm². 2 The actual emission spectrum is shown in Fig. 15. As shown in Fig. 15, the emission spectra of the light-emitting element 1 and the comparative light-emitting element 2 have peaks around 628 nm, both of which are derived from the emission of the organometallic complex, [Ir(dmpqn)2(acac)], contained in the light-emitting layer 913. This is thus suggested.

[0305] Next, reliability tests were conducted on the light-emitting element 1 and the comparative light-emitting element 2. The results of the reliability test are shown in Fig. 16. In Fig. 16, the vertical axis indicates the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates the driving time (h) of the element. The reliability test was carried out with the current density set at 75 m A / cm 2 to drive the light-emitting element.

[0306] From the results of the reliability test, it was found that the light-emitting element 1 exhibits higher reliability than the comparative light-emitting element 2. This can be regarded as an effect of using the organic compound, 13mDBtPBfdbq (structural formula (100)), which is one aspect of the present invention, in the light-emitting layer of the light-emitting element 1. That is, 13mDBtPBfdbq has a structure in which the 2-position and 3-position of the dibenzoquinoxaline skeleton are condensation positions and are condensed with a five-membered ring having oxygen, so, unlike 2mDBTBPDBq-II (structural formula (200)), the substituted phenylene group at the 2-position of the dibenzoquinoxaline skeleton does not twist due to steric repulsion with the hydrogen at the 3-position, and has the characteristic of improving the firmness and stability of the molecule. In Table 2, the fact that the light-emitting element 1 showed better current-voltage characteristics than the comparative light-emitting element 2 suggests that the element structure has a narrow carrier recombination region in the light-emitting layer and is prone to local deterioration. ​​​​​​​​​However, as shown in Fig. 16, it was possible to improve the reliability, which is one aspect of the present invention. In a certain organic compound, in addition to having the characteristic of small steric hindrance, it can be understood that it has good fastness and stability. That is, in one aspect of the present invention a certain organic compound can be said to be a material that overcomes the trade-off phenomenon, which is often seen in light-emitting elements, that the reliability decreases as the driving voltage decreases.

[0307] Furthermore, the organic compound 13mDBtPBfdbq, which is one aspect of the present invention, not only improves the reliability by having the above-described molecular structure, but also minimizes the decrease in the T1 level, which becomes a problem when forming a polycyclic condensed molecular structure, by having a structure condensed with a five-membered ring having oxygen. Specifically, when the T1 level was determined to correspond to the short-wavelength side peak of the phosphorescence spectrum observed at the liquid nitrogen temperature (77K), the T1 level of 2mDBTBPDB q-II was 515 nm, while the T1 level of 13mDBtPBfdbq was suppressed to 538 nm, a red-shift of approximately 20 nm. Therefore, using the organic compound 13mDBtPBfdbq (structural formula (100)), which is one aspect of the present invention, in the EL layer of a light-emitting element is useful not only for improving the reliability of the light-emitting element but also for maintaining the T1 level to some extent.

Example

[0308] ≪Synthesis Example 2≫ In this example, the organic compound, which is one aspect of the present invention represented by the structural formula (101) of Embodiment 1, 13-[3-(dibenzofuran-4-yl)phenyl]dibenzof [f,h][1] Synthesis method of benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBfPBfdbq) will be described. The structure of 13mDBfPBfdbq is shown below.

[0309] [Chemical formula]

[0310] [Synthesis of 13mDBfPBfdbq] 13mDBfPBfdbq shown in this example is synthesized using the method shown in the following synthesis scheme (b-1) in the same manner as the synthesis method of 13mDBtPBfd bq described in Example 1.

[0311] [Chemical formula]

[0312] Thus, the organic compound, 13mDBfPBfdbq, which is one aspect of the present invention, can be obtained. [Examples]

[0313] [Synthesis Example 3] In this example, the synthesis method of the organic compound, 13-[3-(9H-carbazol-9-yl)phenyl]dibenzof[f,h] 1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mCzPBfdbq), which is one aspect of the present invention represented by the structural formula (102) of Embodiment 1, will be described. The structure of 13mCzPBfdbq is shown below.

[0314] [Chemical formula]

[0315] [Synthesis of 13mCzPBfdbq] ​​​The 13mCzPBfdbq shown in this example is synthesized using the method shown in the following synthesis scheme (c-1) in the same manner as the synthesis method of 13mDBtPBfdbq described in Example 1.

[0316]

Chemical formula

[0317] Thus, the organic compound 13mCzPBfdbq, which is one aspect of the present invention, can be obtained.

Example

[0318] ≪Synthesis Example 4≫ In this example, a method for synthesizing an organic compound 13-[3-(triphenylene-2-yl)phenyl]dibenzof[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13mTpPBfdbq), which is one aspect of the present invention represented by the structural formula (110) of Embodiment 1, will be described. The structure of 13mTpPBfdbq is shown below.

[0319]

Chemical formula

[0320] <Synthesis of 13mTpPBfdbq> The 13mTpPBfdbq shown in this example is synthesized using the method shown in the following synthesis scheme (d-1) in the same manner as the synthesis method of 13mDBtPBfdbq described in Example 1.

[0321]

Chemical formula

[0322] Thus, the organic compound 13mTpPBfdbq, which is one aspect of the present invention, can be obtained. ​​​​​​It can be cut.

Example

[0323] ≪Synthesis Example 5≫ In this example, an organic compound which is an aspect of the present invention represented by the structural formula (123) of Embodiment 1, 13-[3-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl) phenyl]dibenzof[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 1 3mPCCzPBfdbq) synthesis method will be described. The structure of 13mPCCzPBf dbq is shown below.

[0324]

Chemical formula

[0325] <Synthesis of 13mPCCzPBfdbq> 13mPCCzPBfdbq shown in this example is synthesized using the method shown in the following synthesis scheme (e-1) in the same manner as the synthesis method of 13mDBtPBf dbq described in Example 1.

[0326]

Chemical formula

[0327] Thus, an organic compound which is an aspect of the present invention, 13mPCCzPBfdbq, can be obtained. It is possible.

Example

[0328] ≪Synthesis Example 6≫ In this example, an organic compound which is an aspect of the present invention represented by the structural formula (125) of Embodiment 1, 13-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)diben zo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13PCCzBfd​​ The synthesis method of bq) will be described. The structure of 13PCCzBfdbq is shown below .

[0329] [Chemical formula]

[0330] [Synthesis of 13PCCzBfdbq] 0.78 g of 13-chlorodibenzo[f,h][1]benzofuro[2, 3-b]quinoxaline, 0.90 g of 9'-phenyl-3,3'-bi-9H-carbazole and 22 mL of mesitylene were placed in a three-necked flask equipped with a reflux condenser, and the inside was purged with nitrogen. After degassing by stirring under reduced pressure in the flask, 0.42 g of sodium tert-butoxide, 0.013 g of bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd(dba)2), and 0.018 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (abbreviation: S-Phos) were added, and the mixture was stirred at 150 °C for 13 hours. After a predetermined time had elapsed, ethanol was added to the resulting mixture, and the mixture was suction filtered and washed with water and ethanol.

[0331] The obtained solid was purified by silica gel column chromatography using toluene as the developing solvent, and then recrystallized from toluene to obtain the target product (yellow solid, yield 0.56 g, yield 35%). The synthesis scheme of the synthesis method shown in this example is shown in the following formula (f-1) . .

[0332] [Chemical formula]

[0333] The nuclear magnetic resonance spectroscopy of the yellow solid obtained above1 The analysis results by (1H-NMR) are shown below. Also, 1 The 1H-NMR chart is shown in FIG. 17. From these results, in this example, the organic compound, 13PCCzBfdbq, which is one aspect of the present invention represented by the above structural formula (125), was obtained. It was found that

[0334] 1 1H-NMR.δ(CDCl3): 7.33 (t, 1H), 7.39 (t, 1H), 7. 45 - 7.56 (m, 6H), 7.62 - 7.69 (m, 5H), 7.79 - 7.90 ( m, 6H), 7.95 (d, 1H), 8.06 (d, 1H), 8.27 (d, 1H), 8 .32 (d, 1H), 8.56 (d, 2H), 8.70 - 8.76 (m, 3H), 9.3 6 (d, 1H), 9.44 (d, 1H).

Explanation of symbols

[0335] 101 First electrode 102 Second electrode 103 EL layer 103a, 103b EL layer 104 Charge generation layer 111, 111a, 111b Hole injection layer 112, 112a, 112b Hole transport layer 113, 113a, 113b Light emitting layer 114, 114a, 114b Electron transport layer 115, 115a, 115b Electron injection layer 200R, 200G, 200B Optical distance 201 First substrate 202 Transistor (FET) 203R, 203G, 203B, 203W Light emitting element 204 EL layer 205 Second substrate 206R, 206G, 206B Color filter 206R’, 206G’, 206B’ color filters 207 First electrode 208 Second electrode 209 Black layer (black matrix) 210R, 210G Conductive layers 301 First substrate 302 Pixel portion 303 Driving circuit section (source line driving circuit) 304a, 304b Driving circuit sections (gate line driving circuits) 305 Sealing material 306 Second substrate 307 Wiring harness 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulator 315 EL layer 316 Second electrode 317 Light emitting element 318 Space 900 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Light emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting device 4001 Substrate 4002 Light emitting element 4003 Substrate 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulating layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffusion plate 4200 Lighting device 4201 Substrate 4202 Light-emitting element 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffusion plate 5101 Light 5102 Wheel 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rearview mirror 7000 Housing 7001 Display section 7002 Second display section 7003 Speaker 7004 LED lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading section 7012 Support section 7013 Earphone 7014 Antenna 7015 Shutter button 7016 Image receiving section 7018 Stand 7020 Camera 7021 External connection section Operation buttons 7022 and 7023 Connection terminal 7024 Band 7025 Microphone 7026 Icon representing time 7027 Other icons 7028 Sensor 7029 Speaker 7030 Information 7052, 7053, and 7054 Mobile information terminal 9310 Display unit 9311 Display area 9312 Hinge 9313 Housing 9315

Claims

1. An organic compound represented by general formula (G1): 【Chemistry 1】 (Wherein, Q represents O, R １ ~R １２ at least one of the groups is a first group having a substituted or unsubstituted condensed aromatic ring having 3 to 30 carbon atoms forming a ring or a substituted or unsubstituted condensed heteroaromatic ring having 3 to 30 carbon atoms forming a ring, and the others each independently represent any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

2. An organic compound represented by general formula (G1): 【Chemistry 2】 (Wherein, Q represents O, R １ ~R １２ At least one of the groups is a first group having a fluorene skeleton, a phenanthrene skeleton, a triphenylene skeleton, a naphthalene skeleton, a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton, and the others each independently represent a hydrogen atom, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

3. In claim 1 or 2, The organic compound has a total carbon number of the first group of 3 to 100.

4. An organic compound represented by general formula (G1): 【Chemistry 3】 (Wherein, Q represents O, R １ ~R １２ at least one of the groups is a first group having a structure represented by any one of the following general formulas (A-1) to (A-21) bonded via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms forming a ring or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring, and the others each independently represent any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. 【Chemistry 4】 (In the formula, Q′ represents O or S, and R １３ ~R ２４ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted carbazolyl group.

5. An organic compound represented by general formula (G1): 【Chemistry 5】 (Wherein, Q represents O, R １ ~R １２ At least one of the groups is a first group represented by any one of the following general formulas (A-1) to (A-21), and the others each independently represent any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. 【Chemistry 6】 (In the formula, Q′ represents O or S, and R １３ ~R ２４ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted carbazolyl group.

6. In any one of claims 1 to 5, R ３ is the first group, an organic compound.

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