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 an optical substance, it is possible to obtain light-emitting elements that emit light of various colors.

[0004] Regarding such light-emitting devices, in order to improve the device characteristics, improvements in the device structure and material development have been carried out. Developments in this field are being actively pursued (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2010-182699 A Summary of the Invention [Problem to be solved by the invention]

[0006] In the development of light-emitting devices, the organic compounds used in the light-emitting devices are Therefore, in one aspect of the present invention, a novel organic compound is provided. That is, the present invention provides a novel organic compound that is effective in improving device characteristics and reliability. In one embodiment of the present invention, a novel organic compound that can be used in a light-emitting element is provided. In one embodiment, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. In addition, a novel highly efficient and reliable emitter using a novel organic compound according to one embodiment of the present invention is The present invention also provides a novel light emitting device, a novel electronic device, or a novel lighting device. The description of these issues does not preclude the existence of other issues. An embodiment of the invention does not necessarily have to solve all of these problems. Other problems will be obvious from the description, drawings, claims, etc. It is possible to extract other issues from the detailed description, drawings, claims, etc. [Means for solving the problem]

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

[0008] [ka]

[0009] In the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of the rings The compound forms a substituted or unsubstituted condensed aromatic ring or a condensed heteroaromatic ring having 3 to 30 carbon atoms. The others are each independently a hydrogen atom, a halogeno group, a hydroxyl group, A group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0010] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0011] [ka]

[0012] In the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of the rings A first group having a substituted or unsubstituted hole-transporting skeleton having 3 to 30 carbon atoms. The others are each independently a hydrogen atom, a halogeno group, a hydroxyl group, an amino group, a nitro group, or or a group having 1 to 50 carbon atoms.

[0013] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0014] [ka]

[0015] In the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of the following is full Olene skeleton, phenanthrene skeleton, triphenylene skeleton, naphthalene skeleton, dibenzothio a first group having either a phene skeleton, a dibenzofuran skeleton, or a carbazole skeleton; and the others are each independently a hydrogen atom, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0016] In each of the above structures, the first group preferably has 3 to 100 carbon atoms in total.

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

[0018] [ka]

[0019] In the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of the rings A substituted or unsubstituted arylene group having 6 to 24 carbon atoms, or a carbon atom forming a ring A compound represented by the following general formula (A-1) is formed via a substituted or unsubstituted heteroarylene group having 3 to 24 prime numbers. ) to (A-21) are bonded to a first group, and the others are each Independently, hydrogen, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms represents any one of the groups

[0020] [ka]

[0021] 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.

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

[0023] [ka]

[0024] In the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of the following: A first group represented by any one of general formulas (A-1) to (A-21), and the others are each Independently, hydrogen, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms represents any one of the groups

[0025] [ka]

[0026] 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.

[0027] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0028] [ka]

[0029] In the general formula (G1), Q represents O or S, and R 3 The number of carbon atoms forming the ring is 3 to 3 A first compound having 0 substituted or unsubstituted fused aromatic rings or fused heteroaromatic rings is a group, R 1 , R 2 and R 4 ~R 12 are each independently a hydrogen atom, a halogen atom, a hydrochloride group, It represents an oxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0030] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0031] [ka]

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

[0033] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0034] [ka]

[0035] In the general formula (G1), Q represents O or S, and R 3 is a fluorene skeleton, phenanthrene phenylene skeleton, triphenylene skeleton, naphthalene skeleton, dibenzothiophene skeleton, dibenzofuran skeleton a first group having either an ortho group or a carbazole group; R 1 , R 2 Oh BiR 4 ~R 12 each independently represents a hydrogen atom, a halogeno group, a hydroxyl group, an amino group, or a nitro group. group, or a group having 1 to 50 carbon atoms.

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

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

[0038] [ka]

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

[0040] [ka]

[0041] 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.

[0042] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0043] [ka]

[0044] In the general formula (G1), Q represents O or S, and R 3 is represented by the following general formulas (A-1) to (A -21), wherein R 1 , R 2 and R 4 ~R 12 That Each independently represents a hydrogen atom, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 1 carbon atoms. It represents any of 50 groups.

[0045] [ka]

[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 containing an organometallic complex or a TADF material is also an embodiment of the present invention. include.

[0051] Another embodiment of the present invention is a light-emitting element using the organic compound according to any one of the above embodiments of the present invention. The EL layer between the pair of electrodes and the light-emitting layer contained in the EL layer may include one of the elements of the present invention. A light-emitting element formed using the organic compound according to the embodiment is also included in one embodiment 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. In addition to these light-emitting devices, microphones, cameras, operation buttons, external connections The scope of the invention also includes electronic devices and lighting devices having a unit, housing, cover, support base, or speaker, etc. Include in.

[0052] The organic compound according to one embodiment of the present invention can be used as a light-emitting substance, and can also emit phosphorescence. The compound can be used in combination with a light-emitting substance (phosphorescent compound) that has a phosphorescent effect, for use in the light-emitting layer of a light-emitting element. That is, it is possible to obtain light emission from the triplet excited state in the light-emitting layer. This is very effective since it enables the efficiency of the element to be increased. A light-emitting element in which an organic compound and a phosphorescent compound are used in combination in a light-emitting layer is one embodiment of the present invention. In addition to the above, a third substance may be added to the light-emitting layer. good.

[0053] Note that one embodiment 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. Therefore, the term "light-emitting device" in this specification includes a light-emitting device such as an image display device. It also refers to a light source (including lighting equipment) that has a connector, such as F PC (Flexible printed circuit) or TCP (Tape A module with a Carrier Package attached, and a printer at the end of the TCP A module with a printed wiring board or a light-emitting element with COG (Chip On Glass) s) All modules in which an IC (integrated circuit) is directly mounted using this method are included in the light-emitting device. Let us assume that. Effect of the Invention

[0054] One embodiment of the present invention can provide a novel organic compound. It is possible to provide a novel organic compound that is effective in improving the reliability of the present invention. In this manner, a novel organic compound that can be used in a light-emitting element can be provided. In one embodiment of the present invention, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. In addition, a highly efficient and reliable photocatalytic reaction can be achieved by using a novel organic compound according to one embodiment of the present invention. It is possible to provide a novel light emitting element having high reliability. In addition, the description of these effects may be used in other applications. However, this does not necessarily prevent the existence of the effects of the above. It is not necessary for the invention to have all of the above effects. Effects other than these effects may be included in the description, drawings, claims, etc. These will become apparent from the description, drawings, claims, etc. It is possible to extract effects other than those mentioned above. [Brief description of the drawings]

[0055] [Figure 1] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 2] 1A and 1B are diagrams illustrating a light-emitting device. [Diagram 3] 1A and 1B are diagrams illustrating a light-emitting device. [Figure 4] 1A to 1C are diagrams illustrating electronic devices. [Diagram 5] 1A to 1C are diagrams illustrating electronic devices. [Figure 6] FIG. [Figure 7] 1A and 1B are diagrams illustrating a lighting device. [Figure 8] 1H-NMR chart of the organic compound shown in structural formula (100). [Figure 9] UV-visible absorption and emission spectra of the organic compound represented by structural formula (100). [Figure 10] 1A to 1C are diagrams illustrating light-emitting elements. [Figure 11] FIG. 13 shows current density-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 12] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 13] FIG. 13 shows luminance-current efficiency characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 14] FIG. 13 shows voltage-current characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 15] FIG. 1 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 16] 13 shows the reliability of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 17] 1H-NMR chart of the organic compound shown in structural formula (125). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0056] Hereinafter, the embodiment of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details are not limited thereto without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the above embodiment. It is not to be construed as being limited to the following:

[0057] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily the same as in the actual embodiment, for ease of understanding. Therefore, the disclosed invention may not necessarily represent the actual position, size, range, etc. The present invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings.

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

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

[0060] The organic compound according to one embodiment of the present invention has a dibenzobenzofuroquinoxaline skeleton or a dibenzo A compound having a structure represented by the following general formula (G1) having a benzothienoquinoxaline skeleton. It is a mechanical compound.

[0061] [ka]

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

[0063] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 1 ~R 12At least one of the rings is a substituted or unsubstituted ring having 3 to 30 carbon atoms. A first group having an unsubstituted hole transporting skeleton, and the others are each independently hydrogen, halogen, or the like. represents any of the following: a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. ." is also acceptable.

[0064] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 1 ~R 12 At least one of the above is a fluorene skeleton, a phenanthrene skeleton, or a triflate skeleton. a phenylene skeleton, a naphthalene skeleton, a dibenzothiophene skeleton, a dibenzofuran skeleton, or a first group having a carbazole skeleton, and the others are each independently hydrogen, halo, Represents either a phenyl group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. " It is also possible to say.

[0065] In addition, the first group in each of the above structures preferably has a total carbon number of 3 to 100. stomach.

[0066] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 1 ~R 12 At least one of the rings is a substituted or unsubstituted ring having 6 to 24 carbon atoms. Unsubstituted arylene group, or substituted or unsubstituted aryl group having 3 to 24 carbon atoms in a ring Represented by any one of the following general formulas (A-1) to (A-21) via a tert-arylene group: The first group is a group having the structure bonded thereto, and the others are each independently a hydrogen atom, a halogeno group, or a hydroxyl group. represents any one of an amino group, a nitro group, or a group having 1 to 50 carbon atoms."

[0067] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 1 ~R 12 At least one of the above is represented by any one of the following general formulae (A-1) to (A-21): or a first group represented by the formula (1), and the others are each independently a hydrogen atom, a halogen atom, or a hydroxyl group. represents any one of an amino group, a nitro group, or a group having 1 to 50 carbon atoms."

[0068] [ka]

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

[0070] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 3 The ring may be a substituted or unsubstituted fused aromatic ring or a fused aromatic ring having 3 to 30 carbon atoms. or a fused heteroaromatic ring; R 1 , R 2 and R 4 ~R 12 each independently represents a hydrogen atom, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a carbon atom; represents any one of the groups having the numbers 1 to 50.

[0071] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R3 is a substituted or unsubstituted hole-transporting skeletal compound having 3 to 30 carbon atoms in a ring. It is the first group with a case, R 1 , R 2 and R 4 ~R 12 are each independently hydrogen, halo A halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. " can also be used.

[0072] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 3 The fluorene skeleton, phenanthrene skeleton, triphenylene skeleton, naphthalene skeleton, The skeleton of the compound is a benzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton. 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 a group having 1 to 50 carbon atoms It can also be written as ".

[0073] In addition, R in each of the above configurations 3 The total number of carbon atoms is preferably 3 to 100.

[0074] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is O or S. R 3 represents a substituted or unsubstituted arylene group having 6 to 24 carbon atoms forming a ring, or via a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring and a first group having a structure represented by any one of the following general formulas (A-1) to (A-21) bonded thereto: and R 1 , R 2 and R 4~R 12 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, represents any one of a silyl group, an amino group, a nitro group, and a group having 1 to 50 carbon atoms. stomach.

[0075] In addition to the above-mentioned structure, the above-mentioned general formula (G1) can also be expressed by the following formula: "In the general formula (G1), Q is 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 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, represents any one of a silyl group, an amino group, a nitro group, and a group having 1 to 50 carbon atoms. stomach.

[0076] [ka]

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

[0078] In each of the above structures, the group having 1 to 50 carbon atoms is an alkyloxy group, an aryloxy group, group, amino group substituted with alkyl group, amino group substituted with aryl group, cyano group, carboxyl group, carboxyl group, alkyloxycarbonyl group, aryloxycarbonyl group, alkyl group substituted silyl groups, aryl substituted silyl groups, alkyl groups, cycloalkyl It is preferable that the aryl group is a aryl group, a heteroaryl group, or an aryl group. Specific examples of the aryl group include a methoxy group, an ethoxy group, a propoxy group, a tert-butoxy group, Phenoxy group, 4-methylphenoxy group, 3,5-dimethylphenoxy group, 1-naphthoxy group 2-naphthoxy group, methylamino group, ethylamino group, dimethylamino group, diethylamino group amino group, methylethylamino group, phenylmethylamino group, phenylamino group, diphenylamino group, phenylamino group, 1-naphthylamino group, 2-naphthylamino group, N-1-naphthyl-N -phenylamino group, N-2-naphthyl-N-phenylamino group, bis(biphenyl-4 -yl)amino group, N,N-bis(p-terphenyl)amino group, methoxycarbonyl group , ethoxycarbonyl group, phenoxycarbonyl group, trimethylsilyl group, triphenyl Silyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group , tert-butyl group, n-hexyl group, benzyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, phenyl group, 1-naphthyl group, 2-naphthyl group group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, phenanthrenyl group, phenylenyl group, 9,9-dimethylfluorenyl group, pyridyl group, quinolyl group, 9-capryl group, Carbazolyl group, 9-phenyl-2-carbazolyl group, 9-phenyl-3-carbazolyl group , dibenzofuranyl group, dibenzothiophenyl group, etc. The carbon number is 25 or less, such as olefinyl group and N,N-bis(p-biphenylyl)amino group. That is, groups having 1 to 25 carbon atoms are preferred in consideration of sublimability.

[0079] Note that in the organic compound of one embodiment of the present invention, hydrogen contained in the skeleton is deuterium. is also good.

[0080] In the above-mentioned structures, in the general formula (G1) or the general formulas (A-1) to (A-21), The substitution is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a s Carbon numbers such as ec-butyl, tert-butyl, n-pentyl, and n-hexyl groups Alkyl groups with 1 to 6 carbon atoms, phenyl groups, o-tolyl groups, m-tolyl groups, p-tolyl groups, 1- Naphthyl group, 2-naphthyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group These groups each represent a substitution by a substituent such as an aryl group having 6 to 12 carbon atoms. The substituents may be bonded to each other to form a ring. For example, the arylene group may be When the phenyl group is a 2,7-fluorenylene group having two phenyl groups at the 9-position as the phenyl group, The fluorene groups may be bonded to each other to form a spiro-9,9'-bifluorene-2,7-diyl group. stomach.

[0081] In each of the above structures, R in general formula (G1) 1 ~R 12 The carbon atoms forming the ring are represented by Specific examples of the condensed aromatic ring or condensed heteroaromatic ring having 3 to 30 rings include a quinoline ring, an isoxa quinazoline ring, quinoxaline ring, naphthalene ring, benzothiophene ring, benzo Furan ring, indole ring, fluorene ring, phenanthrene ring, triphenylene ring, diphenylene ring Zothiophene ring, benzonaphthothiophene ring, dibenzofuran ring, benzonaphthofuran ring , a carbazole ring, a benzocarbazole ring, or a dibenzocarbazole ring. do.

[0082] In each of the above structures, R in general formula (G1) 1 ~R 12 The carbon atoms forming the ring are represented by Specific examples of the hole transporting skeleton having 3 to 30 rings include a naphthalene ring and a benzothiophene ring. , benzofuran ring, indole ring, fluorene ring, phenanthrene ring, triphenylene ring , dibenzothiophene ring, benzonaphthothiophene ring, dibenzofuran ring, benzonaphtho Examples of the ring include a furan ring, a carbazole ring, a benzocarbazole ring, and a dibenzocarbazole ring. Can be obtained.

[0083] In each of the above structures, R in general formula (G1) 1 ~R 12 The carbon atoms forming the ring are represented by Specific examples of the arylene group having 6 to 24 carbon atoms include a phenylene group, a naphthalenediyl group, and a biphenyl group. Phenyldiyl group, terphenyldiyl group, fluorenediyl group, phenanthrenediyl group group, triphenylenediyl group, and the like.

[0084] In each of the above structures, R in general formula (G1) 1 ~R 12 The carbon atoms forming the ring are represented by Specific examples of the heteroarylene group having 3 to 24 carbon atoms include a pyridinediyl group, a pyrazinediyl group, and a pyridinediyl group. pyrimidinediyl group, triazinediyl group, triazolediyl group, oxadiazolyl group, an aryldiyl group, a thiadiazolediyl group, an oxazolediyl group, a thiazoldiyl group, Thiophenediyl group, pyrrolediyl group, furandiyl group, selenophenediyl group, benzoyl group benzothiophenediyl group, benzopyrrolediyl group, benzofurandiyl group, quinolinediyl group diphenyl group, isoquinolinediyl group, dibenzothiophenediyl group, carbazolediyl group, diphenyl group, Examples thereof include a benzofuran diyl group.

[0085] In each of the above structures, 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 a methyl group, an ethyl group, a propyl group, and an isopropyl group. Propyl, butyl, sec-butyl, isobutyl, tert-butyl, butyl pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, Hexyl, isohexyl, sec-hexyl, tert-hexyl, neohexyl 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-diphenyl Examples include a methylbutyl group and a 2,3-dimethylbutyl group.

[0086] In each of the above structures, 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 in the ring include a cyclopentyl group. , cyclohexyl group, cycloheptyl group, and the like.

[0087] Next, specific structural formulas of the organic compounds according to embodiments of the present invention will be shown below.

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] The organic compounds represented by the above structural formulas (100) to (175) are represented by the above general formula (G1) The organic compound according to one embodiment of the present invention is an example of the organic compound represented by the formula: Not limited to.

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

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

[0098] [ka]

[0099] In the general formula (G1), Q represents O or S, and R 1 ~R 12 are each independently hydrogen or a substituent, and R 1 ~R 12 At least one of the rings has 3 to 4 carbon atoms. 30 represents either a substituted or unsubstituted fused aromatic ring or a fused heteroaromatic ring.

[0100] <Method for synthesizing halogen compound represented by general formula (G0)> First, a dibenzobenzofuroquinoxaline derivative represented by the above general formula (G1), or A halogen compound (general formula (G This section explains how to synthesize 0).

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

[0102] [ka]

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

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

[0105] [ka]

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

[0107] <Second synthesis method> The halogen compound represented by the above general formula (G0) can be prepared by the following synthesis scheme (A-1′). As shown above, a phenyl group substituted with a methyloxy group or a methylsulfanyl group and an amino group are Reacting the dibenzoquinoxaline derivative (A1') having a group with tert-butyl nitrite You can also get it by doing this.

[0108] [ka]

[0109] In the synthetic scheme (A-1′), Q represents O or S, and R 31 ~R 42 Haso each independently represents hydrogen or a substituent, and R 31 ~R 42 At least one of the Represents Gen.

[0110] <Method for synthesizing organic compound represented by general formula (G1)> Next, a dibenzobenzofuroquinoxaline derivative represented by the above general formula (G1), or A method for synthesizing a dibenzobenzothienoquinoxaline derivative will be described.

[0111] The dibenzobenzofuroquinoxaline derivative or dibenzo The benzothienoquinoxaline derivative can be synthesized by the synthesis of the above compound as shown in the following synthesis scheme (A-2). 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] [ka]

[0118] The organic compounds represented by the above structural formulas (200) to (223) are represented by the above general formula (G0) This is an example of a halogen compound represented by the formula (I), but the halogen compound is not limited to this.

[0119] As described above, the organic compound, the dibenzobenzofuroquinoxaline derivative, and An example of a method for synthesizing a dibenzobenzothienoquinoxaline derivative has been described above. The light is not limited to this, and may be synthesized by any other synthesis method.

[0120] Note that the organic compound described in this embodiment mode may be appropriately combined with the structures described in other embodiment modes. It can be used.

[0121] Note that the organic compound according to one embodiment of the present invention has an electron-transport property and a hole-transport property. Therefore, it can be used as a host material in the light-emitting layer, or in the electron transport layer or hole transport layer. In addition, the organic compound according to one embodiment of the present invention can maintain a relatively high T1 level. To achieve this, they are used as a host material in combination with a phosphorescent material. In addition, since it exhibits fluorescent emission, it can be used as a light-emitting material for a light-emitting element. Therefore, a light-emitting element including such an organic compound is also included in one embodiment of the present invention. .

[0122] In addition, the organic compound according to one embodiment of the present invention has a low LUMO level and is a compound that easily accepts electrons. Therefore, it is preferable to use it as a host material in an electron transport layer or a light emitting layer. This preferably enables the driving voltage of the light emitting element to be reduced.

[0123] Note that the organic compound of one embodiment of the present invention has a high HOMO level (specifically, −5.7e V or higher) and an organic compound that easily accepts holes to form an exciplex. The excitation energy can be efficiently transferred from the exciplex to the luminescent material. It is possible to improve the efficiency and reliability of phosphorescent light-emitting devices and reduce their driving voltage. The organic compound (hole transport material and electron transport material) to be combined with the organic compound according to one embodiment of the present invention As specific examples of the material, the materials described in Embodiment 2 can be used as appropriate.

[0124] In addition, by using the organic compound which is one embodiment of the present invention, a light-emitting element and a light-emitting In addition, a light emitting device having low power consumption can be realized. It is possible to realize a device, a light-emitting device, an electronic device, or a lighting device.

[0125] Note that one embodiment of the present invention has been described in this embodiment. In the following, one embodiment of the present invention will be described. However, the present invention is not limited to the above. That is, various inventive aspects are described in this and other embodiments. Therefore, one embodiment of the present invention is not limited to a specific embodiment. Although an example in which the present invention is applied to a light-emitting element has been described, one embodiment of the present invention is not limited thereto. Depending on the situation, one embodiment of the present invention may be applied to devices other than light-emitting elements. Depending on the situation, one embodiment of the present invention does not necessarily need to be applied to a light-emitting element.

[0126] The configuration described in this embodiment may be used in appropriate combination with the configurations described in other embodiments. can be done.

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

[0128] <Basic structure of light-emitting element> FIG. 1A shows a light-emitting element having an EL layer sandwiched between a pair of electrodes. The device 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. do.

[0129] FIG. 1B shows a structure in which a plurality of EL layers (two layers in FIG. 1B) (103a, 103b) are disposed between a pair of electrodes. 03b), and a charge generating layer 104 is sandwiched between the EL layers (tandem structure). Such a light-emitting element having a tandem structure can be driven at a low voltage and consumes little power. It is possible to realize a light emitting device with low

[0130] When a voltage is applied between the first electrode 101 and the second electrode 102, the charge generating layer 104 In this case, electrons are injected into one of the EL layers (103a or 103b) and the other EL layer (103b or 103a). Therefore, in FIG. 1B, the first When a voltage is applied to the electrode 101 so that the potential is higher than that of the second electrode 102, a charge is generated. Electrons are injected from layer 104 into EL layer 103a, and holes are injected into EL layer 103b.

[0131] The charge generating layer 104 is transparent to visible light from the viewpoint of light extraction efficiency. In general, it is preferable that the transmittance of visible light through the charge generating layer 104 is 40% or more. In addition, the charge generating layer 104 has a lower conductivity than the first electrode 101 and the second electrode 102. It also works.

[0132] FIG. 1C shows a stacked structure of the EL layer 103. When the first electrode 101 functions as an anode, the EL layer 103 has holes (holes) on the first electrode 101. hole injection layer 111, hole transport layer 112, light emitting layer 113, electron transport layer 114, The electron injection layer 115 is laminated in this order. When the device has multiple EL layers, each EL layer is arranged in the above-mentioned order from the anode side as shown in FIG. The first electrode 101 is a cathode, and the second electrode 102 is a cathode. When the anode is used, the stacking order is reversed.

[0133] In addition, in the case of a structure in which multiple EL layers are stacked, the EL layers are charged as shown in FIG. Three layers (103a, 103b, 103b) are laminated via the generation layers (104a, 104b). However, the number of layers is not limited to two or three. Alternatively, four or more layers may be laminated. The light-emitting layers (113, 113a, 113b, 113c) included in the Each of these has a light-emitting material or a combination of multiple materials, and emits a fluorescent light of a desired color. The light-emitting layer 113 (113a, 113b) can be configured to emit light or phosphorescent light. When a plurality of light emitting layers (113b, 113c) are provided, the light emitting layers may be configured to emit light of different colors. In this case, the luminescent materials and other materials used in each of the laminated luminescent layers are different from each other. For example, the light-emitting layer 113a may be blue, the light-emitting layer 113b may be red, green, or yellow, and light-emitting layer 113c can be blue, while light-emitting layer 113a The light-emitting layer 113b is blue, green, or yellow, and the light-emitting layer 113c is red. It is also possible to use other emission colors appropriately, taking into consideration the luminance and color characteristics of multiple emissions. A combination of the following can be used.

[0134] In the light-emitting element of one embodiment of the present invention, the EL layer (103, 103a, 103b) The light emission obtained by resonating between the two electrodes can be strengthened. For example, in FIG. 1C, the first electrode 101 is a reflective electrode, and the second electrode 10 By using 2 as a semi-transmissive / semi-reflective electrode, a micro-optical resonator (microcavity) structure is formed. This can enhance the light emission from the EL layer 103.

[0135] The first electrode 101 of the light-emitting element is made of a conductive material having reflectivity and a conductive material having light-transmitting property. In the case of a reflective electrode having a laminated structure with a conductive material (transparent conductive film), the thickness of the transparent conductive film is controlled. Specifically, the light emitting layer 113 can be optically adjusted by controlling the light emitting layer 113. The distance between the first electrode 101 and the second electrode 102 is mλ / 2, where λ is the wavelength of light. It is preferable to adjust the value so that it is close to m (where m is a natural number).

[0136] In order to amplify the desired light (wavelength: λ) obtained from the light emitting layer 113, the first electrode the optical distance from 101 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, and the optical distance from the electrode 102 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, , are adjusted to be close to (2m'+1)λ / 4 (where m' is a natural number). The light-emitting region here is preferably a region in which holes in the light-emitting layer 113 and The recombination region with electrons is shown.

[0137] By carrying out such optical adjustment, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be adjusted. This narrows the line width and allows light emission with good color purity to be obtained.

[0138] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is The total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102 is called However, it is necessary to strictly define the reflection area of ​​the first electrode 101 or the second electrode 102. Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, It is assumed that the above-mentioned effect can be obtained by assuming the ray domain. The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 101 / 100 . The optical distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained is called the optical distance. However, it is possible to change the reflecting area of ​​the first electrode 101 and the emitting area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light source is assumed to be the reflection region, and any position on the light-emitting layer where the desired light is obtained is assumed to be the light-emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0139] When the light-emitting element shown in FIG. 1C has a microcavity structure, the EL layer is common. Therefore, it is possible to obtain different emission colors. This eliminates the need for separate coloring (e.g., RGB) for the color layers, enabling high definition. It is also possible to combine it with a color filter. The emission intensity of a specific wavelength in the front direction is Since it is possible to strengthen the signal strength, it is possible to reduce power consumption.

[0140] In the light-emitting element according to one embodiment of the present invention, the first electrode 101 and the second electrode At least one of the electrodes 102 is a light-transmitting electrode (transparent electrode, semi-transmitting / semi-reflective electrode, etc.). When the electrode having light transmission is a transparent electrode, the visible light transmittance of the transparent electrode shall be 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the visible light reflectance of the semi-transmissive / semi-reflective electrode is The ratio is 20% or more and 80% or less, preferably 40% or more and 70% or less. , resistivity is 1×10 -2 It is preferable to set it to Ωcm or less.

[0141] In the above-described light-emitting element which is one embodiment of the present invention, the first electrode 101 and the second electrode When one of the electrodes 102 is a reflective electrode, the possibility of the reflective electrode The reflectance of visible light is set to 40% or more and 100% or less, and preferably 70% or more and 100% or less. In addition, this electrode has a resistivity of 1×10 -2 It is preferable to set it to Ωcm or less.

[0142] <Specific structure and manufacturing method of light-emitting element> Next, a specific structure and a manufacturing method of the light-emitting element which is one embodiment of the present invention will be described. In addition, in Figs. 1(A) to 1(D), when the reference symbols are common, the explanations are also common.

[0143] <First Electrode and Second Electrode> The materials for forming the first electrode 101 and the second electrode 102 are the same as those for the above-mentioned element structure. If the functions of both electrodes can be met, the following materials can be used in appropriate combination. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. Specifically, In-Sn oxide (also called ITO), In-Si- These include Sn oxide (also called ITSO), In-Zn oxide, and In-W-Zn oxide. Other elements include 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), and other metals, as well as combinations of these In addition, alloys containing the above-mentioned elements of Group 1 or Elements in group 2 (e.g., lithium (Li), cesium (Cs), calcium (Ca ), strontium (Sr), europium (Eu), ytterbium (Yb), etc. Use of rare earth metals and alloys containing them in appropriate combination, as well as graphene, etc. can be done.

[0144] The light-emitting element shown in FIG. 1 has an EL layer 103 having a laminated structure as shown in FIG. When the first electrode 101 is an anode, the hole injection layer of the EL layer 103 is disposed on the first electrode 101. 111 and a hole transport layer 112 are successively formed by vacuum deposition. As shown in FIG. 1, a charge generating layer 104 is sandwiched between a plurality of EL layers (103a, 103b) having a laminated structure. 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 are sequentially formed by vacuum deposition. In addition, after the EL layer 103a and the charge generating layer 104 are formed in this order, the charge generating layer 10 4, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are similarly laminated in this order. will be done.

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

[0146] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. Examples of transition metal oxides include oxides of tungsten, manganese, and other oxides. Phthalocyanine (abbreviation: HPc) and copper phthalocyanine (abbreviation: CuPc) Nin-based compounds, etc. can be used.

[0147] In addition, the low molecular weight compound 4,4',4''-tris(N,N-diphenylamino)trimethylsilyl Triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methyl 4,4-phenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA) '-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl( Abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N' -phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD) , 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)- N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6- Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl Nylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9- [Phenylcarbazol-3-yl]amino]-9-phenylcarbazole (abbreviation: PCz Aromatic amine compounds such as PCN1) and the like can be used.

[0148] In addition, poly(N-vinylidene) compounds, which are polymeric compounds (oligomers, dendrimers, polymers, etc.), Poly(4-vinyltriphenylamine) (abbreviation: P VTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl] N-Nyl-N'-phenylamino}phenyl) methacrylamide (abbreviation: PTPDMA), Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] ] (abbreviation: Poly-TPD), etc. can be used. PEDOT / PSS) Adding acids such as polyaniline / poly(styrene sulfonic acid) (abbreviation: PAni / PSS) Polymer compounds such as those mentioned above can also be used.

[0149] In addition, materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptors). A composite material containing an acceptor material can also be used. In this case, the positive Electrons are extracted from the hole transport material and holes are transported in the hole injection layer (111, 111a, 111b). are generated and are transported through the hole transport layers (112, 112a, 112b) to the light emitting layers (113, 113 Holes are injected into the hole injection layers (111, 111a, 113b, 113c). 111b) is a composite material containing a hole transport material and an acceptor material (electron accepting material). It may be formed as a single layer consisting of a hole transport material and an acceptor material (electron acceptor material). The material) may be laminated as separate layers.

[0150] The hole transport layer (112, 112a, 112b) is The holes injected from the first electrode 101 and the charge generating layer 104 are transported to the light emitting layer (11 3, 113a, 113b, 113c). The hole transport layers (112a, 112b) are layers containing a hole transport material. The hole transporting material used in the hole injection layer (111, 111a, 111b) is particularly It is preferable to use a material having a HOMO level equal to or close to the HOMO level of b). It is nice.

[0151] The acceptor material used in the hole injection layer (111, 111a, 111b) is an element Oxides of metals belonging to Groups 4 to 8 of the periodic table can be used. are molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tantalum oxide. Among them, molybdenum oxide is particularly It is preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. The organic acceptors, such as chloranil derivatives and hexaazatriphenylene derivatives, Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetracyano Trafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,1 0,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation In particular, HAT-CN, which contains multiple heteroatoms, can be used. Compounds having a condensed aromatic ring to which an electron-withdrawing group is bonded are preferred because they are thermally stable. In addition, the [3]radia having electron-withdrawing groups (especially halogen groups such as fluoro groups and cyano groups) The olefin derivatives are preferred because they have a very high electron-accepting property. ,2,3-Cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluoroethylene] Fluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetrimethyl Ylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl) Benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidene [2,3,4,5,6-pentafluorobenzeneacetonitrile] and can be.

[0152] The hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 11 The hole transport material used in 2b) is 1×10 -6 cm 2 / Vs or more hole mobility In addition, other than these, any other material having a higher hole transporting property than an electron transporting property is also preferable. The following can be used.

[0153] As the hole transport material, a π-electron-rich heteroaromatic compound (e.g., a compound having a carbazole skeleton) can be used. Compounds with a furan skeleton, compounds with an aromatic amine skeleton, etc. A material with high transmittance is preferred.

[0154] A specific example of the hole transport material is 4,4'-bis[N-(1-naphthyl)-N-phenyl] N,N'-bis(3-methylamino)biphenyl (abbreviation: NPB or α-NPD), 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-phenyl (phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl mBPA FLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-di Methyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2-yl] 9H-fluoren-7-yl)amino]phenylamine (abbreviation: DFLADFL) , N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)difluor N-(4-diphenylaminophenyl)-N-phenylamine (abbreviation: DPNF), 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-dimethyl (9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl) (phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoro PCBBiF, 4,4'-diphenyl-4''-(9-phenyl (9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP) , 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)trimethyl 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-phenyl N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorenyl PCBAF, N-phenyl-N-[4-(9-phenyl-9H -carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine ( Abbreviation: PCBASF), 2-[N-(9-phenylcarbazol-3-yl)-N-phenyl nylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-bis[N -(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluor 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 Using aromatic amine compounds such as fluorene-2,7-diamine (abbreviation: YGA2F), In addition, 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H -Carbazole (abbreviation: PCPN), 4,4',4''-tris(carbazole-9-yl) N-(1-phenyl)triphenylamine (TCTA), 1'-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 (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 with aromatic amine skeletons, 1,3-bis( N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl 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-phenyla 3,6-bis[N-(4 -diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation Name: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-( 1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 3-[ N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol Carbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole -3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA 2) 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amine No]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4- (N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl CzPA, etc. Compounds with a rutile skeleton, 4,4',4''-(benzene-1,3,5-triyl ) tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene ( Abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluorene-9-yl (phenyl)-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Thiophene skeleton compound, 4,4',4''-(benzene-1,3,5-triyl )tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl 1H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmD Examples of compounds having a furan skeleton include compounds having a furan skeleton such as BFFLBi-II.

[0155] In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylphosphine) nylamine) (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. It is also possible.

[0156] However, the hole transport material is not limited to the above, and one or more of various known materials may be used. In combination, the hole injection layer (111, 111a, 111b) and the hole transport layer (111, 111a, 111b) serve as hole transport materials. It can be used for the hole transport layer (112, 112a, 112b). Each of the layers 112, 112a, and 112b may be formed of multiple layers. For example, a first hole transport layer and a second hole transport layer may be laminated.

[0157] In the light-emitting element shown in FIG. 1D, a light-emitting layer 1 is formed on the hole transport layer 112a of the EL layer 103a. The EL layer 103a and the charge generating layer 104 are formed by vacuum deposition. After the formation, the light-emitting layer 113b is formed on the hole transport layer 112b of the EL layer 103b by vacuum deposition. is formed.

[0158] <Light-emitting layer> The light-emitting layers (113, 113a, 113b, 113c) are layers containing a light-emitting substance. Luminescent materials include blue, purple, blue-purple, green, yellow-green, yellow, orange, and red. In addition, a material exhibiting different properties is appropriately used for the light-emitting layers (113a, 113b, 113c). By using luminescent materials having different luminescent colors (for example, complementary colors), It is possible to obtain white light by combining different luminescent colors. A laminated structure having different light emitting materials may also be used.

[0159] The light-emitting layers (113, 113a, 113b, 113c) are made of a light-emitting material (guest material). In addition, one or more organic compounds (host material, assist material) may be included. In addition, the one or more organic compounds may be a hole-transporting compound described in this embodiment. Either or both of a conductive material and an electron transporting material can be used.

[0160] As a luminescent material that can be used in the luminescent layer (113, 113a, 113b, 113c), The light-emitting material is not particularly limited, and may be a light-emitting material that converts singlet excitation energy into light in the visible light region, or The present invention can use a luminescent material that converts triplet excitation energy into light emission in the visible light region. The organic compound according to one embodiment of the present invention exhibits fluorescence, and therefore has singlet excitation energy in the visible light region. It can be used as a luminescent material that changes the light emitted from the other regions. Examples of such measures include the following:

[0161] Luminescent materials that convert singlet excitation energy into light include fluorescent materials. Examples of such derivatives include pyrene derivatives, anthracene derivatives, triphenylene derivatives, and fluoro derivatives. Oleno derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives In particular, pyrene derivatives are The photon yield is high, which is preferable. 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'-biphenyl (dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation Name: 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,N'-(pyrene-1,6-diamine) (abbreviation: 1,6BnfAPrn), 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] (abbreviation :1,6BnfAPrn-03).

[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-cal 4'-(10-phenyl-9-anthryl)-4'-(10-phenyl-9-benzol-9-yl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl Phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo 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-diyldi-4,1- phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviation Name: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-phenyl] N-(2-phenyl)-9H-carbazol-3-amine (abbreviation: 2PCAPPA), -[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) etc. can be used. do.

[0163] In addition, examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials. Materials that exhibit thermally activated delayed fluorescence (thermally activated delayed fluorescence) tivated delayed fluorescence (TADF) materials are can be.

[0164] Phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since each substance has a different emission color (emission peak), it is necessary to select the appropriate one as needed. Select and use.

[0165] Blue or green, with a peak wavelength of 450 nm or more and 570 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0166] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrPrp tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl [Ir(iPr5 btz)3]), organometallic complexes with 4H-triazole skeletons such as tris[3- Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato ]Iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl 1H-1,2,4-triazolato)iridium(II I) (abbreviation: [Ir(Prptz1-Me)3]) Organometallic complexes, fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl] [Ir(iPrpmi)3 ]), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f] [Ir(dmpimpt-Me)3 Organometallic complexes with imidazole skeletons such as bis[2-(4',6'-difluorophenyl] (O-phenyl)pyridinato-N,C 2’ ]Iridium(III) tetrakis(1-pyrazo aryl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pi Lysinato-N,C 2’ ]Iridium(III) picolinate (abbreviation: Firpic), S(2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’ }Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) , bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium (III) Acetylacetonate (abbreviation: FIr(acac)) Examples of such a complex include an organometallic complex having a phenylpyridine derivative as a ligand.

[0167] It has a green or yellow color and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0168] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i Lithium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bi Bis(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-phenyl Rupyrimidinato]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( Organometallic complexes with pyrimidine skeletons such as (acetylacetonato) Bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [I r(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl Pyr-3-methyl-2-phenylpyrazinate)iridium(III) (abbreviation: [Ir(m ppr-iPr)2(acac)]), an organometallic complex having a pyrazine skeleton, S(2-phenylpyridinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pp y)3]), bis(2-phenylpyridinato-N,C 2’ ) Iridium(III) acetyl Ir(ppy)2(acac) 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’ ) Iridium Ir(III) acetylacetonate (abbreviation: [Ir(pq)2(acac)]) 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’ ) Iridi Ir(bt)2(acac) and other In addition to organometallic complexes, tris(acetylacetonato)(monophenanthroline)terbium (III) (abbreviation: [Tb(acac)3(Phen)]) Can be obtained.

[0169] Yellow or red, with a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0170] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinium] dinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), S[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloyl Thanato)bis[4,6-di(naphthalene-1-yl)pyrimidinato]iridium(III ) (abbreviation: [Ir(d1npm)2(dpm)]) Metal Complex, (acetylacetonato)bis(2,3,5-triphenylpyrazinate)iridide Ir(tppr)2(acac)], bis(2,3,5-trimethylammonium bromide) Triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir (tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-fluoro (fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2( Organometallic complexes with pyrazine skeletons such as tris(1-phenylisocyanide) and tris(1-phenylisocyanide). Sokinorinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(piq)3]), Bi S(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) acetylacetonate Organogold compounds with pyridine skeletons such as Ir(piq)2(acac) Complexes of 2,3,7,8,12,13,17,18-octaethyl-21H,23H-poly 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 However, any material that satisfies the above conditions is more preferred. For example, anthracene derivatives and tetracene derivatives are also suitable.

[0173] Thus, examples of host materials that can be combined with fluorescent emitting materials include 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-phenyl nyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: F LPPA), 5,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl) )Tetracene, etc.

[0174] When the emitting material is a phosphorescent material, the host material is a material that has triplet excitation energy ( Organic compounds with triplet excited energy greater than the energy difference between the ground state and the triplet excited state It is to be noted that the hole transporting material and the electron transporting material shown in this embodiment mode may be used. In addition to the above materials, bipolar materials can be used as the host material. For example, anthracene derivatives and phenanthrene derivatives are preferable. , pyrene derivatives, chrysene derivatives, dibenzo[g,p]chrysene derivatives, and other condensed polycyclic aromatic Aromatic compounds and the like are also suitable.

[0175] Therefore, examples of the host material to be combined with the phosphorescent emitting material include 9,10-difluorophenyl ether. Phenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10- Cz A1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DP hPA), YGAPA, PCAPA, 9-(4-{4'-[N-phenyl-N-(N-phenyl phenyl-3-carbazolyl)]amino}phenyl)phenyl-10-phenylanthracene PCAPBA, N-(9,10-diphenyl-2-anthryl)-N,9- Diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-dimethyl Toxo-5,11-diphenylchrysene, N,N,N',N',N'',N'',N'' ',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetrahydrofuran DBC1, CzPA, 3,6-diphenyl-9-[4-(10-phenyl) Nyl-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 ( Abbreviated as DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as DPNS2), 1,3,5-tri(1-pyrenyl)benzene (TPB3), etc. Some examples include:

[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 metal-containing porphyrins include those containing Pd. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hematopoietin Lufirin-Tin Fluoride Complex (abbreviation: SnF2 (Hemato IX)), Coproporf Fluorine 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)), octaethylene Examples include thylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0179] 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-carbazole-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)phenyl phenyl-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT) , 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-xanthene-9- ACRXTN, bis[4-(9,9-dimethyl-9,10-dihydroacrylamide 10-phenyl-10H,1-lysine)phenyl]sulfone (abbreviation: DMAC-DPS) 0'H-spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACR Heterocyclic compounds having π-electron rich heteroaromatic rings and π-electron deficient heteroaromatic rings such as ... In addition, when a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded to each other, The bonded substances have the donor properties of the π-electron rich heteroaromatic ring and the access properties of the π-electron deficient heteroaromatic ring. The difference in energy between the singlet and triplet excited states becomes smaller. Therefore, it is particularly preferred.

[0180] In addition, when using a TADF material, it can also be used in combination with other organic compounds.

[0181] By appropriately using the above materials, the light-emitting layers (113, 113a, 113b, 113c) The above materials can also be combined with low molecular weight materials and polymeric materials. This can be used to form the light-emitting layers (113, 113a, 113b, 113c). do.

[0182] In the light-emitting device shown in FIG. 1D, an electron transport layer is provided on the light-emitting layer 113a of the EL layer 103a. After the EL layer 103a and the charge generating 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 b) converts the electrons injected from the second electrode 102 into the light-emitting layers (113, 113a, 113b). 3b, 113c). ) is a layer containing an electron transporting material. The electron transport material used is 1×10 -6 cm 2 A material having an electron mobility of 1000 nm or more is preferred. It is preferable to use a material other than the above as long as it has a higher electron transporting property than a hole transporting property. The organic compound according to one embodiment of the present invention satisfies these requirements. Since a low level leads to a reduction in the driving voltage, the electron transport layer is preferably provided with a It is preferable to use organic compounds. Other possible materials are listed below.

[0184] As the electron transporting material, there are metal complexes having a quinoline skeleton, Metal complexes, metal complexes having an oxazole skeleton, metal complexes having a thiazole skeleton, etc. , oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives Conductors, thiazole derivatives, phenanthroline derivatives, quinoline derivatives with quinoline ligands Conductors, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, pyrimidine These include aryl, bipyridine, pyrimidine, and other nitrogen-containing heteroaromatic compounds. For example, a material having a high electron transporting property, such as a π-electron deficient heteroaromatic compound, can be used.

[0185] A specific example of an electron transport material is 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-phenylphenyl) (Enolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc (II) Metal complexes having a quinoline skeleton or a benzoquinoline skeleton, such as Znq , 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) and other metal complexes having an oxazole or thiazole skeleton. can be done.

[0186] In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl) 1,3-bis[5-(p-tetraphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 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) and other oxadiazole derivatives, 3- (4'-tert-butylphenyl)-4-phenyl-5-(4''-biphenyl)-1 ,2,4-Triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4 -(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation Triazole derivatives such as p-EtTAZ, 2,2',2''-(1,3,5-benzo[a]pyridine, Zentriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) , 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzo Imidazole derivatives such as benzoimidazole (abbreviation: mDBTBIm-II) (including benzoxazole derivatives) and 4,4'-bis(5-methylbenzoxazol-2-yl) Stilbene (abbreviation: BzOS) and other oxazole derivatives, bathophenanthroline (abbreviation: : Bphen), Bathocuproine (abbreviation: BCP), 2,9-bis(naphthalene-2- yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), etc. The phenanthroline derivative, 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]dibe Benzo[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]dibenzyl Quinoxaline derivatives such as quinoxaline[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) or dibenzoquinoxaline derivatives, 3,5-bis[3-(9H-carbazole-9 -yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3 pyridine derivatives such as 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 pyrimidine derivatives such as 2-{ 4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazole-9 -yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzP Tzn), 9-[3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl mPCCzPTz n-02) and other triazine derivatives can be used.

[0187] In addition, 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) You can also be there.

[0188] In addition, the electron transport layer (114, 114a, 114b) may be a single layer or may be made of the above-mentioned material. The layer may have a structure in which two or more layers made of the above are laminated.

[0189] Next, in the light-emitting element shown in FIG. 1(D), an electrode was formed on the electron transport layer 114a of the EL layer 103a. The electron injection layer 115a is formed by vacuum deposition. Then, the EL layer 103a and the charge generating layer 115b are After the green layer 104 is formed and the electron transport layer 114b of the EL layer 103b is formed, The child injection layer 115b is formed by vacuum deposition.

[0190] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing a substance with high electron injection properties. The electron injection layers (115, 115a, 115b) are made of lithium fluoride (LiF), cerium fluoride (CeF), CsF, Calcium Fluoride (CaF2), Lithium Oxide (LiO x ) etc. Such alkali metals, alkaline earth metals, or compounds thereof can be used. In addition, rare earth metal compounds such as erbium fluoride (ErF3) can be used. In addition, an electride may be used for the electron injection layer (115, 115a, 115b). For example, a mixed oxide of calcium and aluminum with high electron doping is used as a tritride. In addition, the above-mentioned electron transport layer (114, 114a, 114b) It is also possible to use a substance constituting the above.

[0191] In addition, the electron injection layer (115, 115a, 115b) contains an organic compound and an electron donor (donor A composite material containing the above-mentioned compound may be used. Since electrons are generated in the organic compound, the organic compound has excellent electron injection and transport properties. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons. Specifically, for example, the electron transporting layer (114, 114a, 114b) described above may be used Materials such as metal complexes and heteroaromatic compounds can be used as electron donors. Any substance that exhibits electron donating properties to organic compounds is acceptable. The lithium earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, Erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metals Metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like. Alternatively, a Lewis base such as magnesium oxide can be used. Organic compounds such as thiafulvalene (abbreviation: TTF) can also be used.

[0192] In the light-emitting element shown in FIG. 1D, the light obtained from the light-emitting layer 113b is amplified. In this case, the optical distance between the second electrode 102 and the light-emitting layer 113b is It is preferable that the electron transport layer 1 is formed so that the wavelength λ of the light to be transmitted is less than ¼. This can be adjusted by changing the film thickness of 14b or the electron injection layer 115b.

[0193] <Charge generation layer> In the light-emitting element shown in FIG. 1D, the charge generating layer 104 is When a voltage is applied between the second electrode (cathode) 102, electrons are injected into the EL layer 103a. The charge generating layer 104 has a function of injecting holes into the EL layer 103b. Even if an electron acceptor is added to the electron transport material, An electron donor may be added. The charge generation layer 104 may be formed using the above-mentioned materials. This makes it possible to suppress an increase in driving voltage when EL layers are stacked.

[0194] In the case where the charge generating layer 104 is configured such that an electron acceptor is added to a hole transporting material, As the hole transporting material, the material shown in this embodiment mode can be used. The receptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinoline. Examples include dimethane (abbreviation: F4-TCNQ), chloranil, etc. Examples of the oxides of metals belonging to Groups 4 to 8 in the table include: Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide Examples of the oxide include tin, manganese oxide, and rhenium oxide.

[0195] In the case where the charge generating layer 104 has a structure in which an electron donor is added to an electron transporting material, As the electron transporting material, the materials shown in this embodiment mode can be used. The donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or an element of the periodic table. Metals belonging to Groups 2 and 13 in the table and their oxides and carbonates can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium Ca, Yb, In, Lithium oxide, Cesium carbonate It is preferable to use organic compounds such as tetrathianaphthalene. It may also be used as a donor.

[0196] <Substrate> The light-emitting element shown in this embodiment mode can be formed on various substrates. The type of substrate is not limited to a specific one. An example of the substrate is a semiconductor substrate (e.g. Single crystal substrate or silicon substrate), SOI substrate, glass substrate, quartz substrate, plastic substrate , metal substrate, stainless steel substrate, substrate with stainless steel foil, tantalum Tungsten substrate, substrate with tungsten foil, flexible substrate, lamination film, Examples of the material include paper containing fibrous materials and base films.

[0197] Examples of the glass substrate include barium borosilicate glass and aluminoborosilicate glass. Glass or soda lime glass. Flexible substrates, lamination films, etc. Examples of base films include polyethylene terephthalate (PET), polyethylene Plastics such as polyolefin naphthalate (PEN) and polyethersulfone (PES) Synthetic resins such as acrylic resin, polypropylene, polyester, polyvinyl fluoride, Polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic deposition film Examples of materials that can be used include glass, plastic, or paper.

[0198] Note that the light-emitting element shown in this embodiment mode can be manufactured by a vacuum process such as a deposition method or a spin-coil method. Solution processes such as the inkjet method and the ink-jet method can be used. In this case, sputtering, ion plating, ion beam deposition, molecular beam deposition, Physical vapor deposition (PVD) methods such as air vapor deposition and chemical vapor deposition (CVD) methods can be used. In particular, the functional layer (hole injection layer (111, 111a, 111)) included in the EL layer of the light-emitting element can be formed. b), hole transport layer (112, 112a, 112b), light emitting layer (113, 113a, 113 b, 113c), electron transport layer (114, 114a, 114b), electron injection layer (115, 1 15a, 115b), and the charge generating layer (104, 104a, 104b), Vacuum deposition method (vacuum deposition method, etc.), coating method (dip coating method, die coating method, bar coating method, stripping method, etc.) Pin coat method, spray coat method, etc.), printing method (inkjet method, screen (stencil printing offset (lithographic printing), flexography (letterpress printing), gravure, microcompression The insulating layer can be formed by a method such as a contact method or a nanoimprint method.

[0199] The EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are 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)), charge generation layer ( 104, 104a, 104b) are not limited to the above-mentioned materials and may be other materials. However, as long as the functions of each layer can be fulfilled, they can be used in combination. The following compounds are considered to be suitable for use: high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (low molecular weight compounds, Compounds in the intermediate range between polymers and molecules: molecular weight 400-4000), inorganic compounds (quantum dot materials As the quantum dot material, colloidal quantum dots can be used. Materials, alloy-type quantum dot materials, core-shell-type quantum dot materials, core-type quantum dot materials, etc. etc. can be used.

[0200] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments. It is possible.

[0201] (Embodiment 3) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described. The light emitting device shown in FIG. 1 comprises a transistor (FET) 202 and a light emitting element (2 03R, 203G, 203B, 203W) are electrically connected to form an active matrix. A light-emitting device of the type having a plurality of light-emitting elements (203R, 203G, 203B, 203W) 204, and the electrodes of each light-emitting element are electrically connected to each other according to the color of the light emitted by each light-emitting element. The optical path length of the EL layer 204 is adjusted to obtain a microcavity structure. The emitted light is reflected by the color filters (206R, 206G, 206 It is a top-emission type light-emitting device in which light is emitted through a

[0202] In the light-emitting device shown in FIG. 2A, the first electrode 207 is formed to function as a reflective electrode. In addition, the second electrode 208 is formed so as to function as a semi-transmissive and semi-reflective electrode. In other embodiments, the electrode material for forming the first electrode 207 and the second electrode 208 may be Please refer to the description and use it as appropriate.

[0203] In addition, in FIG. 2A, for example, the light emitting element 203R is a red light emitting element, and 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. In this case, the light-emitting element 203R has a first electrode 207 and a second electrode 208 as shown in FIG. The light emitting element 203G is adjusted so that the optical distance between the light emitting element 203G and the pole 208 is 200R. The optical distance between the first electrode 207 and the second electrode 208 is adjusted to 200G. 03B is arranged so that the optical distance between the first electrode 207 and the second electrode 208 is 200B. As shown in FIG. 2B, the conductive layer 210R in the light-emitting element 203R is adjusted. A conductive layer 210G is laminated on the first electrode 207 in the light emitting element 203G. This allows optical adjustment.

[0204] Color filters (206R, 206G, 206B) are formed on the second substrate 205. A color filter allows a specific wavelength range of visible light to pass through and blocks a specific wavelength range. Therefore, as shown in FIG. 2A, the filter overlaps with the light emitting element 203R. A color filter 206R that passes only the red wavelength region is provided at the position Red light can be obtained from the light emitting element 203R. By providing a color filter 206G that transmits only the wavelength range of the light emitting element 203 Green light can be obtained from G. Also, a blue wavelength region is obtained at a position overlapping with the light emitting element 203B. By providing a color filter 206B that transmits only blue light, the light emitting element 203B However, the light emitting element 203W does not need to be provided with a color filter. It is possible to obtain white light emission. A color filter (206R) may be provided. , 206G, 206B) and the black layer 209 are covered with an overcoat layer made of a transparent material. It is okay if it is.

[0205] In FIG. 2A, a structure (top emission type) in which light is extracted on the second substrate 205 side is used. A light emitting device is shown, but as shown in FIG. 2(C), a first substrate on which a FET 202 is formed The light emitting device may have a structure in which light is extracted from the 201 side (bottom emission type). In the case of a bottom emission type light emitting device, the first electrode 207 is a semi-transmissive and semi-reflective electrode. The first electrode 206 is formed to function as a reflecting electrode, and the second electrode 208 is formed to function as a reflecting electrode. The first substrate 201 is at least a light-transmitting substrate. (206R', 206G', 206B') are light emitting elements (203 R, 203G, and 203B) on the first substrate 201 side.

[0206] In addition, in FIG. 2(A), the light emitting elements are red light emitting elements, green light emitting elements, blue light emitting elements, Although the case of a white light-emitting element has been described, the light-emitting element which is one embodiment of the present invention is not limited to this structure. The light emitting element may be a yellow light emitting element or an orange light emitting element. In order to manufacture these light-emitting devices, EL layers (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, etc.) are For the materials used in the layer (e.g., the electron injection layer, the charge generation layer, etc.), see the description of other embodiments. In this case, the color filter may be appropriately selected according to the color of the light emitted by the light emitting element. The filter must be selected appropriately.

[0207] By adopting the above-mentioned configuration, a light-emitting device having light-emitting elements that emit light of a plurality of colors can be obtained. can be obtained.

[0208] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiments. It is possible to do so.

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

[0210] By applying the element configuration of the light-emitting element according to one embodiment of the present invention, It is possible to manufacture a light-emitting device or a passive matrix type light-emitting device. A matrix type light emitting device is a device that combines light emitting elements and transistors (FETs). Therefore, the light emitting device may be a passive matrix type light emitting device or an active matrix type light emitting device. Note that the light-emitting device described in this embodiment can also include other The light emitting element described in the embodiment can be applied.

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

[0212] 3A is a top view showing the light emitting device 21, and FIG. 3B is a top view showing the light emitting device 21 along the dashed line A in FIG. The active matrix type light emitting device is a sectional view taken along the line -A'. A pixel portion 302, a driving circuit portion (source line driving circuit) 303, and a driving circuit portion (Gate line driving circuits) (304a, 304b). Pixel section 302 and driving circuit section (303, 304a, 304b) are connected to the first substrate 301 and the second substrate 302 by a sealing material 305. The substrate 306 is sealed therebetween.

[0213] Moreover, on the first substrate 301, a lead wiring 307 is provided. The driver is electrically connected to the FPC 308, which is an external input terminal. An external signal (e.g., a video signal, a clock signal, etc.) is input to the driving circuit unit (303, 304a, 304b). The FPC308 also transmits signals such as the lock signal, start signal, and reset signal, as well as electrical potential. A printed wiring board (PWB) may be attached. The state in which B is attached is included in the light emitting device.

[0214] Next, a cross-sectional structure of the light-emitting device is shown in FIG.

[0215] The pixel section 302 includes a FET (switching FET) 311 and a FET (current control FET). 312, and a plurality of pixels having a first electrode 313 electrically connected to the FET 312. The number of FETs in each pixel is not particularly limited, and may be any number. It can be provided appropriately as needed.

[0216] The FETs 309, 310, 311, and 312 are not particularly limited, and may be, for example, staggered. In addition, top-gate and bottom-gate transistors can be used. The transistor may have a structure such as a Tom-gate type.

[0217] The semiconductors that can be used for these FETs 309, 310, 311, and 312 are The crystallinity is not particularly limited, and may be an amorphous semiconductor, a semiconductor having crystallinity (a microcrystalline semiconductor, Any of polycrystalline semiconductors, single crystal semiconductors, and semiconductors having crystalline regions in some parts may be used. By using a crystalline semiconductor, deterioration of transistor characteristics can be suppressed. This is preferable.

[0218] In addition, these semiconductors include, for example, Group 14 elements, compound semiconductors, and oxide semiconductors. , organic semiconductors, etc. can be used. Representative examples include semiconductors containing silicon, gallium, etc. A semiconductor containing arsenic, an oxide semiconductor containing indium, or the like can be used.

[0219] The driving circuit section 303 includes a FET 309 and a FET 310. The ET310 is a circuit that contains transistors of one polarity (either N-type or P-type only). Alternatively, the transistor may be a CMOS circuit including an N-type transistor and a P-type transistor. Alternatively, a configuration having an external driver circuit may be used.

[0220] The end of the first electrode 313 is covered with an insulator 314. , organic compounds such as negative photosensitive resins and positive photosensitive resins (acrylic resins), and acids. Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride can be used. It is preferable that the upper end or the lower end of the edge 314 has a curved surface having a curvature. This allows the film formed on the upper layer of the insulator 314 to have good coverage.

[0221] An EL layer 315 and a second electrode 316 are stacked on the first electrode 313. 315 is 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. Yes.

[0222] Note that the structure of the light-emitting element 317 in this embodiment mode may be the same as that described in the other embodiment modes or materials. Although not shown here, the second electrode 316 is connected to an external input. It is electrically connected to the terminal FPC308.

[0223] In addition, although only one light emitting element 317 is shown in the cross-sectional view shown in FIG. 02, a plurality of light emitting elements are arranged in a matrix. 2, light-emitting elements capable of emitting three kinds of light (R, G, B) are selectively formed, and It is possible to form a light-emitting device capable of displaying three colors (R, G, B). In addition to the light-emitting element from which light is obtained, for example, white (W), yellow (Y), magenta (M For example, a light-emitting element that can emit light of three colors (R, A light-emitting element capable of emitting the above-mentioned several types of light is added to a light-emitting element capable of emitting the light of G and B. This can improve color purity and reduce power consumption. By combining it with a filter, a light emitting device capable of full color display may be formed. The color filters are red (R), green (G), blue (B), cyan (C), and magenta. Colors such as ink (M), yellow (Y), etc. can be used.

[0224] The FETs (309, 310, 311, 312) and the light-emitting element 317 on the first substrate 301 are The second substrate 306 and the first substrate 301 are bonded together with a sealant 305. A space 318 surrounded by the first substrate 301, the second substrate 306, and the sealant 305 is formed. The space 318 is filled with an inert gas (nitrogen, argon, etc.) It may be filled with an organic material (including a sealant 305).

[0225] The sealing material 305 can be made of epoxy resin or glass frit. It is preferable to use a material that is as impermeable to moisture and oxygen as possible for the insulating material 305. The second substrate 306 may be made of the same material as the first substrate 301. Therefore, it is possible to use various substrates described in other embodiments as appropriate. In addition to glass and quartz substrates, FRP (Fiber-Reinforced Plastics) is also used as the substrate. d Plastics), PVF (Polyvinyl fluoride), polyester or acrylic A plastic substrate made of a resin such as glass frit can be used as a sealing material. When using a glass substrate, the first substrate 301 and the second substrate 306 are preferably made of glass from the viewpoint of adhesiveness. It is preferably a substrate.

[0226] In this manner, an active matrix light emitting device can be obtained.

[0227] In addition, when an active matrix type light emitting device is formed on a flexible substrate, The FET and the light emitting element may be formed directly, or the FET and the light emitting element may be formed on a separate substrate having a release layer. After forming the semiconductor, the FET and the light emitting element are separated from each other by applying heat, force, laser irradiation, etc. The peeling layer may be, for example, a thin film. Inorganic films such as tungsten and silicon oxide films, and organic resin films such as polyimide are used. In addition, a substrate on which a transistor can be formed can be used as the flexible substrate. In addition to plates, paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, Fabric substrates (natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester, etc.) , leather substrate, or rubber substrate. By using these substrates, durability It has excellent heat resistance and can be made lighter and thinner.

[0228] Note that the structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible.

[0229] (Embodiment 5) In this embodiment, a light-emitting element which is one embodiment of the present invention, Examples of various electronic devices and automobiles to which the light emitting device is applied will be described. Note that the light-emitting device is mainly used for a display portion in the electronic device described in this embodiment mode. This can be done.

[0230] The electronic device shown in FIG. 4A to FIG. 4C includes a housing 7000, a display portion 7001, a speaker 7003, LED lamp 7004, operation key 7005 (power switch or operation switch ), a connection terminal 7006, a sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity , rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage , power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared measurement functions. ), a microphone 7008, etc.

[0231] FIG. 4A shows a mobile computer, which includes, in addition to the above, a switch 7009, a red It may have an outside line port 7010, etc.

[0232] FIG. 4B shows a portable image reproducing device (for example, a DVD reproducing device) equipped with a recording medium. In addition to the above, it has a second display unit 7002, a recording medium reading unit 7011, etc. This can be done.

[0233] Figure 4(C) shows a digital camera with a television receiving function, which, in addition to the above, has an antenna 7014, a shutter button 7015, an image receiving unit 7016, etc.

[0234] FIG. 4D shows a portable information terminal. The portable information terminal displays information on three or more screens of a display unit 7001. In this example, information 7052, information 7053, and information 7054 are For example, the user may carry a mobile information terminal in his / her breast pocket. Information displayed in a position that can be observed from above the mobile information terminal when the terminal is stored. The user can check the display without taking the mobile information terminal out of his pocket. and can decide, for example, whether to answer the phone or not.

[0235] FIG. 4E shows a portable information terminal (including a smartphone), in which a display unit 7000 is mounted on a housing 7000. 001, operation keys 7005, etc. The portable information terminal may have a speaker, The portable information terminal may be provided with a connection terminal, a sensor, etc. It can be displayed on the surface of the number. Here is an example showing three icons 7050. Also, information 7051 shown in a dashed rectangle can be displayed on another surface of the display unit 7001. Examples of information 7051 include notifications of incoming e-mails, SNS, and phone calls, etc. Subject of e-mail or SNS, sender name, date and time, battery level, antenna reception Or, the location where the information 7051 is displayed may have an icon 7050 or the like. Any of the above may be displayed.

[0236] Figure 4(F) shows a large television set (also called a television or television receiver). The electronic device may have a housing 7000, a display unit 7001, and the like. The housing 7000 is supported by a support 7018. The operation of the display unit 7111 can be performed by a separate remote control unit 7111. The display unit 7001 may be provided with a touch sensor, and the operation can be performed by touching the display unit 7001 with a finger or the like. The remote control unit 7111 may output information The remote control 7111 may have a display unit that displays the operation keys or buttons. The channel and volume can be controlled by the touch panel, and the display unit 7001 displays The image displayed can be manipulated.

[0237] The electronic devices shown in FIGS. 4A to 4F can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display unit, 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. In addition, the connection terminal 7024 can be used to transmit data to and from other information terminals. Charging can also be performed by wireless power supply.

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

[0240] The smart watch shown in FIG. 4G can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display unit, 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. It may have the function of

[0241] In addition, a speaker, a sensor (force, displacement, position, velocity, acceleration, angular velocity, degree, rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, Includes functions to measure pressure, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays. ), a microphone, etc.

[0242] Note that a light-emitting device according to one embodiment of the present invention and a display device having a light-emitting element according to one embodiment 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 a light emitting device is applied is shown in FIG. The device can be integrated with the automobile. Outer lights 5101 (including the rear of the vehicle), tire wheels 5102, doors 5103 It can be applied to a part or the whole of the car. A display unit 5104, a handle 5105, a shift lever 5106, a seat 5107, an inner - It can be applied to rear view mirrors 5108, etc. It can also be applied to some glass windows. You may do so.

[0246] As described above, electronic devices and automobiles to which the light-emitting device or the display device according to one embodiment of the present invention is applied can be used. In this case, it is possible to realize a long-life electronic device. The electronic devices and automobiles that can be used are not limited to those shown in the present embodiment, but can be used in any field. It is possible to apply

[0247] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0248] (Embodiment 6) In this embodiment, a light-emitting device according to one embodiment of the present invention or a light-emitting element which is a part of the light-emitting device is used. The structure of a lighting device manufactured using this will be described with reference to FIG.

[0249] 7(A) and (B) are cross-sectional views of an example of a lighting device. Note that FIG. 7(A) shows a light source on the substrate side. The bottom emission type lighting device extracts light from the encapsulation substrate side. It is a top-emission lighting device that emits light.

[0250] A lighting device 4000 shown in FIG. 7A has a light-emitting element 4002 on a substrate 4001. The light emitting element 4002 has a substrate 4003 having projections and recesses on the outer side of the substrate 4001. It has a first electrode 4004 , an EL layer 4005 , and a second electrode 4006 .

[0251] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. 008. An auxiliary wiring electrically connected to the first electrode 4004. An insulating layer 4010 may be formed on the auxiliary wiring 4009. There are.

[0252] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light emitting element 4002. It is preferable that the substrate 4003 has the unevenness as shown in FIG. This can improve the efficiency of extracting the light generated in 02.

[0253] A lighting device 4200 in FIG. 7B has a light-emitting element 4202 over a substrate 4201. The 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 the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. 208. The auxiliary wiring 4 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0255] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 421 are provided between the sealing substrate 4211 and the light emitting element 4202. 4 may be provided. Note that since the sealing substrate 4211 has projections and recesses as shown in FIG. The extraction efficiency of the light generated by the light emitting element 4202 can be improved.

[0256] An example of the application of these lighting devices is a ceiling light for indoor lighting. There are two types of ceiling lights: ceiling-mounted and ceiling-embedded. Such an illumination device is constructed by combining a light-emitting device with a housing or a cover.

[0257] Other applications include footlights that can illuminate the floor and increase safety at your feet. It is also possible to use a footlight in a bedroom, on stairs, or in a hallway. In the case of , the size and shape can be changed appropriately according to the size and structure of the room. It is also possible to combine the device with a support stand to create a stationary lighting device. .

[0258] It can also be used as a sheet-shaped lighting device (sheet-shaped lighting). The lighting is attached to the wall, so it doesn't take up much space and can be used for a wide range of purposes. It is also easy to make it larger. It can also be used on curved walls and housings.

[0259] In addition to the above, a light-emitting device according to one embodiment of the present invention may be attached to a part of furniture in a room. By applying the light-emitting element, which is a part of the device, it is possible to create a lighting device that also functions as furniture. Cut.

[0260] As described above, various lighting devices using the light-emitting device can be obtained. 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, 1,4-dihydrophenanthro[9,10-b]pyrazine obtained in step 1 above is 3.91 g of α-2,3-dione and 60 mL of dehydrated DMF were placed in a three-neck flask equipped with a reflux condenser. The inside of the flask was replaced with nitrogen. After cooling the flask on ice, 5.4 mL of phosphoryl chloride was added and 1 The mixture was stirred at 00°C for 7.5 hours. After the specified time had elapsed, the resulting mixture was diluted with 1M sodium hydroxide solution After pouring into 130 mL of the solution, it was filtered by suction. The solid obtained was washed with water and ethanol, The mixture was dissolved in toluene and filtered through Celite. The filtrate was concentrated to give The desired quinoxaline derivative was obtained (yellowish white powder, yield 1.00 g, 22%). The synthesis scheme of compound 2 is shown in the following formula (a-2).

[0267] [ka]

[0268] Step 3: 2-chloro-3-(5-chloro-2-methoxyphenyl)quinoxaline Synthesis> Next, 2,3-dichlorodibenzo[f,h]quinoxaline 1.8 obtained in step 2 above was 5g, 5-chloro-2-methoxyphenylboronic acid 1.16g, sodium carbonate 0.66 g, 27 mL of ethylene glycol dimethyl ether (abbreviation: DME), and 27 mL of water were The contents were placed in a three-neck flask equipped with a flow tube, and the inside of the flask was replaced with nitrogen. The contents of the flask were stirred under reduced pressure. After degassing, tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(P 0.48 g of Ph3) and 4) were added, and the mixture was stirred at 100°C for 20.5 hours to react. After filtration, water was added to the mixture, and the solid obtained by suction filtration was dissolved in dichloromethane and filtered. The filtrate was concentrated. The resulting solid was extracted with toluene:hexane=1:2 as a developing solvent. The product was purified by silica gel column chromatography to obtain the desired quinoxaline derivative ( White powder, yield 1.86 g, 74% yield). The synthesis scheme of step 3 is shown in the following formula (a-3 ) as shown in

[0269] [ka]

[0270] <Step 4: 2-Chloro-3-(5-chloro-2-hydroxyphenyl)quinoxaline Synthesis of > Next, 2-chloro-3-(5-chloro-2-methoxyphenyl) Put 2.56 g of quinoxaline and 70 mL of dehydrated dichloromethane into a three-neck flask and fill it with nitrogen. The flask was cooled to -20°C, and then boron tribromide (1M dichloromethane solution) was added. After the specified time had elapsed, water was added, and dichloromethane was added. The solid obtained by the operation was extracted with dichloromethane as a developing solvent. The desired quinoxaline derivative was obtained by purifying the product using silica gel column chromatography. The synthesis scheme of step 4 is shown in the following formula (a -4).

[0271] [ka]

[0272] <Step 5: 13-Chlorodibenzo[f,h][1]benzofuro[2,3-b]quinox Synthesis of Sarin> Next, the 2-chloro-3-(5-chloro-2-hydroxyphenyl) 2.12 g of quinoxaline and 27 mL of dehydrated N-methyl-2-pyrrolidone (abbreviation: NMP) The mixture was placed in a three-neck flask equipped with a reflux condenser and the inside of the flask was replaced with nitrogen. After adding 1g of 10 ... The solid was filtered off with suction. The solid was washed with ethanol to obtain the target quinoxalate. The compound was obtained as a pale yellow powder (yield: 1.56 g, 84%). The formula is shown in formula (a-5) below.

[0273] [ka]

[0274] < Step 6: 13-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h][1]Benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq Synthesis of Furthermore, the 13-chlorodibenzo[f,h][1]benzofuro[2, 3-b]quinoxaline 0.78g, (dibenzothiophen-4-yl)phenyl-3-borate 1.10 g of sucrose, 1.26 g of cesium fluoride, and 44 mL of mesitylene were added to a flask equipped with a reflux condenser. The contents of the flask were stirred under reduced pressure to degas the contents. After that, tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba) 3) 0.075g, 2'-(dicyclohexylphosphino)acetophenone ethylene dimethyl 0.059 g of alcohol was added and stirred at 120°C for 17.5 hours. Ethanol was added to the mixture, which was then suction filtered and washed with water and ethanol. Dissolve in ethylene and filter through a filter aid consisting of layers of celite, alumina, and celite. The product was obtained by recrystallization from toluene (yellowish white powder, yield: 0.71 g, yield 56%). 0.70 g of the resulting yellowish white powder was subjected to train sublimation. The sublimation purification was carried out using the argon gas method. The conditions for the sublimation purification were a pressure of 2.7 Pa and an argon gas flow rate of 10. The solid was heated at 330°C while flowing at 5mL / min. After purification by sublimation, the target yellowish white product The solid was obtained in an amount of 0.56 g and a yield of 80%. The synthesis scheme of step 6 is shown in the following formula (a-6 ) as shown in

[0275] [ka]

[0276] Nuclear magnetic resonance spectroscopy of the yellow-white solid obtained in step 6 above ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in FIG. In the present invention, the organic compound represented by the above structural formula (100) is 13mD It was found that BtPBfdbq was obtained.

[0277] 1 H-NMR.δ(CDCl3):7.49-7.51(m,2H),7.63-7.6 4(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 UV-visible absorption spectra of the toluene solution and solid thin film of 13mDBtPBfdbq were The absorption spectrum (hereinafter simply referred to as "absorption spectrum") and emission spectrum were measured.

[0279] The absorption spectrum in toluene solution was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation). The emission spectrum in the toluene solution was measured using a fluorometer. The absorption spectrum of the obtained toluene solution was The results of the measurements of the absorption and emission spectra are shown in Fig. 9(A). The horizontal axis is the wavelength, and the vertical axis is the absorption intensity. and luminescence intensity.

[0280] From the results of Figure 9(A), in the toluene solution of 13mDBtPBfdbq, the peaks at 281 nm and Absorption peaks are seen around 397 nm and 405 nm (excitation wavelength 372 nm). Wavelength peaks were observed.

[0281] To measure the absorption spectrum of a solid thin film, a solid thin film was prepared by vacuum deposition on a quartz substrate. The measurements were performed using a UV-Vis spectrophotometer (Hitachi High-Technologies U4100). The emission spectrum of the solid thin film was measured using the same solid thin film as above, and the fluorescence The absorption of the obtained solid thin film was measured using a spectrophotometer (FS920, manufactured by Hamamatsu Photonics, Inc.). The measurement results of the spectrum and the emission spectrum are shown in FIG. 9(B). The horizontal axis is the wavelength, and the vertical axis is the absorption The absorption and emission intensities are shown.

[0282] From the results of FIG. 9(B), the solid thin film of 13mDBtPBfdbq has a peak at 383 nm and 40 An absorption peak is seen around 3 nm, and an emission peak is seen around 511 nm (excitation wavelength 380 nm). A peak was seen.

[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] [ka]

[0287] <Fabrication of light-emitting element> The light emitting device shown in this embodiment has a first electrode 9 formed on a substrate 900 as shown in FIG. 01, a hole injection layer 911, a hole transport layer 912, a light emitting layer 913, an electron transport layer 914, and an electron A structure in which an electron injection layer 915 is laminated in this order, and a second electrode 903 is laminated on the electron injection layer 915. has.

[0288] First, a first electrode 901 was formed on a substrate 900. The electrode area was 4 mm 2 (2mm x 2 The thickness of the first electrode 901 was 1 mm. The substrate 900 was a glass substrate. , Indium tin oxide containing silicon oxide (ITSO) was sputtered to a thickness of 70 nm. The film was formed to a thickness of 100 nm.

[0289] As a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0290] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed by vacuum evaporation. 1×10 -4 After depressurizing to 100 Pa, 4,4',4''-(benzene-1,3,5 -triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide The ratio of DBT3P-II to molybdenum oxide was 2:1 (mass ratio), and the film thickness was 70 nm. The film was formed by co-evaporation so as to form a

[0291] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was '-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenyl The film was formed by vapor deposition of PCBBi1BP to a thickness of 20 nm. did.

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

[0293] In the case of the light-emitting element 1, the light-emitting layer 913 contains, as a host material, the organic compound according to one embodiment of the present invention. The material, 13mDBtPBfdbq, was used as the assist material, and PCBBiF and guest material ( Phosphorescent material) Bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl- κC](2,4-pentanedionato-κ 2 O,O') Iridium(III) (abbreviation: [I r(dmpqn)2(acac)]) with a weight ratio of 13mDBtPBfdbq:PC BBiF:[Ir(dmpqn)2(acac)]=0.75:0.25:0.1 The film thickness was set to 40 nm.

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

[0295] Next, the electron transport layer 914 was formed on the light emitting layer 913. The electron transport layer 914 was formed of 9-[3- (4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl The thickness of the film of ruthenium-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02) is 3 0 nm, 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenyl The film was then deposited in a thickness of 15 nm on the anthroline (NBphen) layer. Ta.

[0296] Next, the electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was made of fluoride. Lithium (LiF) was used and the film was formed by vapor deposition to a thickness of 1 nm.

[0297] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was made of aluminum. The aluminum was deposited by vapor deposition to a thickness of 200 nm. Thus, the second electrode 903 functions as a cathode.

[0298] Through the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 900. In addition, the hole injection layer 911, the hole transport layer 912, the light emitting layer 913, and the electrode layer 914 described in the above steps were The electron transport layer 914 and the electron injection layer 915 are functional layers constituting the EL layer in one embodiment of the present invention. In addition, in the deposition process in the above-mentioned manufacturing method, the deposition method is all performed by resistance heating. Used.

[0299] Moreover, the light emitting element manufactured as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the sealing is performed in a glove box with a nitrogen atmosphere. Then, another substrate (not shown) coated with a sealant that is hardened by ultraviolet light is placed on the substrate 900. The substrates are fixed together so that the sealant adheres to the periphery of the light emitting element formed on the substrate 900. During sealing, 365 nm ultraviolet light was applied at 6 J / cm. 2 Irradiate the sealant to solidify it. The sealant was stabilized by heat treatment at 80° C. for 1 hour.

[0300] <Operation characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting devices were measured. The measurements were performed at room temperature (25°C). The results are shown in Figs. 11 to 14.

[0301] Table 2 below shows 1000cd / m 2 The main initial characteristic values ​​of each light-emitting element in the vicinity are shown.

[0302] [Table 2]

[0303] In addition, in the above results, the light-emitting element 1 fabricated in this example exhibited better performance than the comparative light-emitting element 2. This shows that the light-emitting element 1 has excellent current-voltage characteristics. In one embodiment of the present invention, 13mDBtPBfdbq is fused with a five-membered ring having oxygen. This is because the cyclic structure of the cyclic BOF has a deep LUMO level. The reduction potential of 2mDBTBPDBq-II was measured by CV. The MO level of 13mDBtPBfdbq is -2.94 eV, while the LUMO level of 13mDBtPBfdbq is was -3.17 eV.

[0304] Furthermore, the light-emitting element 1 and the comparative light-emitting element 2 were subjected to an electric current of 2.5 mA / cm 2 A current was passed with a current density of The emission spectra at that time are shown in FIG. 15. As shown in FIG. 15, the light-emitting element 1 and the comparative light-emitting element The emission spectrum of molecule 2 has a peak at around 628 nm. The emission from the organometallic complex, [Ir(dmpqn)2(acac)], This suggests that...

[0305] Next, a reliability test was performed on the light-emitting element 1 and the comparative light-emitting element 2. Results of the reliability test The results are shown in FIG. 16. In FIG. 16, the vertical axis represents the normalized brightness (%) when the initial brightness is 100%. The horizontal axis indicates the operation time (h) of the element. The reliability test was performed at a current density of 75m A / cm 2 The light emitting element was driven by setting the voltage at

[0306] The results of the reliability test showed that the light-emitting element 1 exhibited higher reliability than the comparative light-emitting element 2. This is the organic compound 13mDBtPBfdbq (structure 13mDBtPBfdbq) which is one embodiment of the present invention. This can be seen as an effect of using the compound (100) in the light-emitting layer of the light-emitting element 1. That is, 13mDBtPBfdbq is, as described in the first embodiment, a dibenzoquinone. The 2nd and 3rd positions of the sarin skeleton are condensed with an oxygen-containing five-membered ring. Therefore, dibenzoquinoxaline, such as 2mDBTBPDBq-II (structural formula (200)), The substituted phenylene group at the 2-position of the phenylene skeleton is twisted due to steric repulsion with the hydrogen at the 3-position. The absence of the above-mentioned problems improves the robustness and stability of the molecule. The fact that the light-emitting element 1 showed better current-voltage characteristics than the comparative light-emitting element 2 indicates that the light-emitting layer This suggests that the recombination region of the carriers in the device is narrow and that localized degradation is likely to occur. However, the reliability was improved as shown in FIG. 16, which is one aspect of the present invention. In some organic compounds, in addition to being characterized by low steric hindrance, they also have good robustness. This can be understood to be because the compound has good properties and stability. A certain organic compound is not suitable for use in light-emitting devices because the reliability decreases when the driving voltage decreases. It can be said that this material overcomes the trade-off phenomenon that is often seen in materials.

[0307] Furthermore, the organic compound 13mDBtPBfdbq according to one embodiment of the present invention is By adopting this structure, not only is reliability improved, but the five-membered ring containing oxygen is condensed. By having this structure, the decrease in the T1 level, which is a problem when a polycyclic condensed molecular structure is used, is minimized. Specifically, the T1 level was observed at the liquid nitrogen temperature (77K). The calculated value corresponds to the short-wavelength peak of the phosphorescence spectrum, and is 2mDBTBPDB The T1 level of q-II is 515 nm, while the T1 level of 13mDBtPBfdbq The wavelength shift was suppressed to 538 nm, which is a long wavelength shift of about 20 nm. The organic compound 13mDBtPBfdbq (structural formula (100)) is used as the EL layer of the light-emitting device. The use of ZnO in this case not only improves the reliability of the light-emitting device, but also helps maintain the T1 level to some extent. It can be said that it is useful in that it can EXAMPLES

[0308] <Synthesis Example 2> In this example, an organic compound represented by structural formula (101) in Embodiment 1, which is one embodiment of the present invention, Compound, 13-[3-(dibenzofuran-4-yl)phenyl]dibenzo[f,h][1] Method for synthesizing benzofuro[2,3-b]quinoxaline (abbreviation: 13mDBfPBfdbq) The structure of 13mDBfPBfdbq is shown below.

[0309] [ka]

[0310] <Synthesis of 13mDBfPBfdbq> The 13mDBfPBfdbq shown in this embodiment is the 13mDBtPBfd described in the first embodiment. Similar to the synthesis method for bq, it is synthesized by the method shown in the following synthesis scheme (b-1).

[0311] [ka]

[0312] As a result, the organic compound 13mDBfPBfdbq, which is one embodiment of the present invention, can be obtained. can. EXAMPLES

[0313] <Synthesis Example 3> In this example, an organic compound represented by structural formula (102) in Embodiment 1, which is one embodiment of the present invention, Compound, 13-[3-(9H-carbazol-9-yl)phenyl]dibenzo[f,h][ 1] Synthesis of benzofuro[2,3-b]quinoxaline (abbreviation: 13mCzPBfdbq) The structure of 13mCzPBfdbq is shown below.

[0314] [ka]

[0315] <Synthesis of 13mCzPBfdbq> The 13mCzPBfdbq shown in this embodiment is the 13mDBtPBfdb described in the first embodiment. The compound is synthesized by the method shown in the following synthetic scheme (c-1), similarly to the synthetic method for compound q.

[0316] [ka]

[0317] As a result, the organic compound 13mCzPBfdbq, which is one embodiment of the present invention, can be obtained. Cut. EXAMPLES

[0318] <Synthesis Example 4> In this example, an organic compound represented by structural formula (110) in Embodiment 1, which is one embodiment of the present invention, is used. Compound, 13-[3-(triphenylen-2-yl)phenyl]dibenzo[f,h][1] A method for synthesizing benzofuro[2,3-b]quinoxaline (abbreviation: 13mTpPBfdbq) The structure of 13mTpPBfdbq is shown below.

[0319] [ka]

[0320] <Synthesis of 13mTpPBfdbq> The 13mTpPBfdbq shown in this embodiment is the 13mDBtPBfdb described in the first embodiment. The compound is synthesized by the method shown in the following synthetic scheme (d-1) in the same manner as in the synthetic method of q.

[0321] [ka]

[0322] As a result, the organic compound 13mTpPBfdbq, which is one embodiment of the present invention, can be obtained. Cut. EXAMPLES

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

[0324] [ka]

[0325] <Synthesis of 13mPCCzPBfdbq> The 13mPCCzPBfdbq shown in this embodiment is the 13mDBtPBf described in the first embodiment. The compound is synthesized by the method shown in the following synthetic scheme (e-1), similarly to the synthetic method for dbq.

[0326] [ka]

[0327] As a result, the organic compound 13mPCCzPBfdbq, which is one embodiment of the present invention, can be obtained. can be done. EXAMPLES

[0328] <Synthesis Example 6> In this example, an organic compound represented by structural formula (125) in Embodiment 1, which is one embodiment of the present invention, Compound, 13-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)dibenzoyl Zo[f,h][1]benzofuro[2,3-b]quinoxaline (abbreviation: 13PCCzBfd The synthesis method of 13PCCzBfdbq is explained below. The structure of 13PCCzBfdbq is shown below. .

[0329] [ka]

[0330] <Synthesis of 13PCCzBfdbq> 13-Chlorodibenzo[f,h][1]benzofuro[2, 3-b]quinoxaline 0.78g, 9'-phenyl-3,3'-bi-9H-carbazole 0.90g and 22mL of mesitylene were placed in a three-neck flask equipped with a reflux condenser, and the inside was purged with nitrogen. The flask was degassed by stirring under reduced pressure, and then sodium tert-butoxy 0.42 g of bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd(db a) 2) 0.013g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.018 g of phenyl (abbreviation: S-Phos) was added, and the mixture was stirred at 150° C. for 13 hours.

[0331] After a certain time has elapsed, ethanol is added to the resulting mixture, which is then suction filtered and washed with water and ethanol. The solid obtained was purified by silica gel column chromatography using toluene as a developing solvent. After purifying with toluene, the target product was obtained by recrystallization from toluene (yellow solid, yield The synthesis scheme of the synthesis method shown in this example is shown in the following formula (f-1): As shown in.

[0332] [ka]

[0333] The yellow solid obtained above was analyzed by nuclear magnetic resonance spectroscopy (1 The results of the analysis using H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in FIG. The organic compound represented by the above structural formula (125) according to one embodiment of the present invention, 13PCCz It was found that Bfdbq was obtained.

[0334] 1 H-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 generating 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 Board 206R, 206G, 206B Color Filters 206R', 206G', 206B' Color filters 207 First Electrode 208 Second Electrode 209 Black layer (black matrix) 210R, 210G conductive layer 301 First Substrate 302 Pixel section 303 Driver circuit section (source line driver circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Second Board 307 Wiring 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulation 315 EL layer 316 Second Electrode 317 Light-emitting element 318 Space 900 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting Equipment 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 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4200 Lighting Equipment 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 Diffuser 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rear view mirror 7000 Chassis 7001 Display section 7002 2nd 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 unit 7012 Support part 7013 Earphones 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7021 External connection part 7022, 7023 Operation buttons 7024 Connection terminal 7025 band, 7026 Microphone 7027 Time Icon 7028 Other Icons 7029 Sensor 7030 Speaker 7052, 7053, 7054 Information 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 Case

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 3 to 100 in the first group.

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.

Images