Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device

Abstract

One embodiment of the present invention provides a novel organic compound. In other words, provided is a novel organic compound which is superior in improving element characteristics and reliability. One embodiment of the present invention is an organic compound represented by formula (G1). # imgabs0 # (In the formula, Ar represents an unsubstituted arylene group having 6 to 13 carbon atoms. Cz represents an unsubstituted carbazolyl group or a carbazolyl group substituted at the 9-position by a phenyl group; r5 represents an unsubstituted phenyl group or an unsubstituted naphthyl group; r16 represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an unsubstituted carbazolyl group or a carbazolyl group substituted at the 9-position by a phenyl group; each of R11 to R15 and R17 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; in addition, each of R1 to R4 and R6 to R9 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ).

Description

This application is a divisional application of the Chinese patent application titled “Organic compounds, light-emitting elements, light-emitting devices, electronic devices and lighting devices” with national application number 201880010759.4 after the PCT international application with international application number PCT / IB2018 / 050474 and international application date January 26, 2018 entered the Chinese stage. 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. One embodiment of the present invention is not limited to the above-mentioned technical field. That is, one embodiment of the present invention relates to an object, a method, a manufacturing method, or a driving method. In addition, one embodiment of the present invention relates to a process, a machine, a product, or a composition of matter. In addition, specifically, as an example, a semiconductor device, a display device, a liquid crystal display device, etc. can be cited. Background Art

[0002] Since a light-emitting element having an EL layer sandwiched between a pair of electrodes (also called an organic EL element) has characteristics such as thinness and lightness, high-speed response to input signals, and low power consumption, a display using such a light-emitting element is expected to be used as a next-generation flat panel display.

[0003] In a light-emitting element, a voltage is applied between a pair of electrodes, and electrons and holes injected from each electrode recombine in the EL layer, and the light-emitting substance (organic compound) contained in the EL layer becomes an excited state. When the excited state returns to the ground state, light is emitted. In addition, as the types of excited states, there are singlet excited states (S * ) and triplet excited state (T * ), where light emission from a singlet excited state is called fluorescence, and light emission from a triplet excited state is called phosphorescence. In addition, in a light-emitting element, the statistical generation ratio of a singlet excited state and a triplet excited state is considered to be S * :T * = 1: 3. The emission spectrum obtained from a light-emitting substance is unique to the light-emitting substance, and by using different kinds of organic compounds as the light-emitting substance, a light-emitting element exhibiting various light-emitting colors can be obtained.

[0004] In order to improve the device characteristics of the above-mentioned light-emitting devices, improvements in device structures, development of materials, etc. are being actively carried out (for example, refer to Patent Document 1). [Prior technical literature] [Patent Document]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 2010-182699 Summary of the invention Technical problem to be solved by the invention

[0006] In the development of light-emitting elements, organic compounds used in light-emitting elements are very important in improving the characteristics and reliability of light-emitting elements. One embodiment of the present invention provides a novel organic compound. That is, a novel organic compound that is effective in improving element characteristics and reliability is provided. In addition, one embodiment of the present invention provides a novel organic compound that can be used in a light-emitting element. In addition, one embodiment of the present invention provides a novel organic compound that can be used in an EL layer of a light-emitting element. In addition, one embodiment of the present invention provides a novel light-emitting element with high efficiency and high reliability using the novel organic compound of one embodiment of the present invention. In addition, one embodiment of the present invention provides a novel light-emitting device, a novel electronic device or a novel lighting device. Note that the description of these purposes does not prevent the existence of other purposes. Note that one embodiment of the present invention does not need to achieve all of the above purposes. In addition, purposes other than the above purposes can be clearly seen from the description of the specification, drawings, claims, etc., and purposes other than the above purposes can be extracted from the description of the specification, drawings, claims, etc. Solutions to technical problems

[0007] One embodiment of the present invention is an organic compound having an anthracene skeleton and a carbazole skeleton and represented by the following general formula (G1).

[0008] [Chemical formula 1]

[0009] Note that in the general formula (G1), Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R 1 To R 9 and R 11 To R 17 Each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of the rings may be a fused ring.

[0010] Another embodiment of the present invention is an organic compound in which the 9-position, 3-position or 2-position of the carbazole skeleton represented by Cz in the general formula (G1) is bonded to the carbazole skeleton.

[0011] Another embodiment of the present invention is an organic compound in which Ar in the general formula (G1) is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group.

[0012] In another embodiment of the present invention, R in the above general formula (G1) 5 An organic compound which is a substituted or unsubstituted aromatic group having 6 to 13 carbon atoms.

[0013] The organic compound of one embodiment of the present invention has an anthracene skeleton and a carbazole skeleton. A plurality of organic compounds having an anthracene skeleton have been developed as bipolar fluorescent host materials, but since the organic compound of one embodiment of the present invention has not only an anthracene skeleton but also a carbazole skeleton, the organic compound of one embodiment of the present invention is a fluorescent host material exhibiting good hole transport properties compared to organic compounds consisting only of an anthracene skeleton.

[0014] In addition, an organic compound of one embodiment of the present invention is a fluorescent host material having an anthracene skeleton and a bicarbazole skeleton. Note that in the case of such an organic compound, the organic compound having a HOMO orbital located in the bicarbazole skeleton tends to have a shallower HOMO energy level than the case where the HOMO orbital is located in the anthracene skeleton. When such a fluorescent host material having a shallower HOMO energy level is used for the light-emitting layer, the difference between the HOMO energy level of the light-emitting layer and the HOMO energy level of the hole transport layer in contact with the light-emitting layer is reduced, thereby easing the injection barrier of holes from the hole transport layer to the light-emitting layer and improving the injectability of holes from the hole transport layer to the light-emitting layer. Thus, it is possible to reduce the driving voltage or improve the luminous efficiency.

[0015] In addition, the organic compound of one embodiment of the present invention has an anthracene skeleton and a carbazole skeleton. By setting the 2-position of the first carbazole skeleton bonded to the anthracene skeleton and the bonding position of the second carbazole skeleton bonded thereto to the desired position, the Stokes shift is smaller than the case where the 3-position of the first carbazole skeleton and the second carbazole skeleton are bonded, and the energy level of the singlet excited state can be higher, so it is easy to achieve energy transfer to a shorter wavelength guest material. Thus, the luminous efficiency of the light-emitting element can be improved. In addition, the reliability of the element can be improved. Note that in the organic compound of one embodiment of the present invention, the 2-position of the first carbazole skeleton bonded to the anthracene skeleton and the 9-position, 3-position or 2-position of the second carbazole skeleton are bonded, so it is easy to synthesize, so it is preferred.

[0016] Another embodiment of the present invention is an organic compound represented by Structural Formula (200), Structural Formula (220), Structural Formula (221), Structural Formula (252) or Structural Formula (253).

[0017] [Chemical formula 2]

[0018] Another embodiment of the present invention is a light-emitting device using an organic compound having an anthracene skeleton and a carbazole skeleton. In addition, the present invention also includes a light-emitting device including the above organic compound and a guest material.

[0019] Another embodiment of the present invention is a light-emitting element using an organic compound of one embodiment of the present invention. In addition, the present invention also includes a light-emitting element in which an EL layer between a pair of electrodes or a light-emitting layer in the EL layer contains an organic compound of one embodiment of the present invention. In addition to the light-emitting element, a light-emitting device including a transistor or a substrate is also included in the scope of the invention. In addition, in addition to the above-mentioned light-emitting device, electronic devices and lighting devices including microphones, cameras, operation buttons, external connection parts, housings, covers, support tables or speakers are also included in the scope of the invention.

[0020] In addition, one embodiment of the present invention includes not only a light-emitting device having a light-emitting element, but also a lighting device having a light-emitting device. Therefore, the light-emitting device in this specification refers to an image display device or a light source (including a lighting device). In addition, the light-emitting device also includes the following modules: a module that connects a connector such as an FPC (Flexible Printed Circuit) or TCP (Tape Carrier Package) to the light-emitting device; a module that sets a printed circuit board at the end of a TCP; or a module that directly mounts an IC (integrated circuit) on a light-emitting element by a COG (Chip On Glass) method. Effects of the Invention

[0021] One embodiment of the present invention can provide a novel organic compound. That is, a novel organic compound that is effective in improving device characteristics or reliability can be provided. In addition, one embodiment of the present invention can provide a novel organic compound that can be used for a light-emitting element. In addition, one embodiment of the present invention can provide a novel organic compound that can be used for the EL layer of a light-emitting element. In addition, one embodiment of the present invention can provide a novel light-emitting element with high efficiency and high reliability using the novel organic compound of one embodiment of the present invention. In addition, one embodiment of the present invention can provide a novel light-emitting device, a novel electronic device, or a novel lighting device. Note that the description of these effects does not prevent the existence of other effects. One embodiment of the present invention does not need to achieve all of the above effects. In addition, effects other than these effects can be clearly seen from the description of the specification, drawings, claims, etc., and effects other than these effects can be extracted from the description of the specification, drawings, claims, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] [ Fig. 1 ] A diagram illustrating the structure of a light-emitting element. [Fig. 2] A diagram illustrating a light-emitting device. [Fig. 3] A diagram illustrating a light-emitting device. [Fig. 4] A diagram illustrating an electronic device. [Fig. 5] A diagram illustrating an electronic device. [Fig. 6] A diagram illustrating a car. [Fig. 7] A diagram illustrating a lighting device. [ Figure 8 ]A diagram illustrating a lighting device. [Figure 9] Organic compound represented by structural formula (200) 1 H-NMR spectrum. [ Figure 10 ] The UV-visible absorption spectrum and emission spectrum of the organic compound represented by structural formula (200). [Figure 11] Organic compound represented by structural formula (221) 1 H-NMR spectrum. [Figure 12] The UV-visible absorption spectrum and emission spectrum of the organic compound represented by structural formula (221). [ Fig.13 ]A diagram illustrating the structure of a light-emitting element. [ Fig.14 ] shows a graph of the current density-brightness characteristics of light-emitting element 1 and comparative light-emitting element 2. [ Fig.15 ] is a graph showing the voltage-luminance characteristics of light-emitting element 1 and comparison light-emitting element 2. [ Fig.16] is a graph showing the brightness-current efficiency characteristics of light-emitting element 1 and comparative light-emitting element 2. [ Fig.17 ] is a graph showing the voltage-current characteristics of light-emitting element 1 and comparative light-emitting element 2. [ Fig.18 ] shows the emission spectra of light-emitting element 1 and comparison light-emitting element 2. [ Fig.19 ] is a diagram showing the reliability of light-emitting element 1 and comparison light-emitting element 2. [Figure 20] Organic compound represented by structural formula (252) 1 H-NMR spectrum. [Figure 21] The UV-visible absorption spectrum and emission spectrum of the organic compound represented by structural formula (252). [Figure 22] Organic compound represented by structural formula (253) 1 H-NMR spectrum. [Figure 23] UV-visible absorption spectrum and emission spectrum of the organic compound represented by structural formula (253). [Figure 24] Organic compound represented by structural formula (220) 1 H-NMR spectrum. [ Fig. 25 ] The UV-visible absorption spectrum and emission spectrum of the organic compound represented by structural formula (220). [ Fig.26 ] is a graph showing the current density-luminance characteristics of light-emitting element 3. [ Fig. 27 ] is a graph showing the voltage-luminance characteristics of light-emitting element 3. [ Fig.28 ] is a graph showing the brightness-current efficiency characteristics of light-emitting element 3. [ Fig.29 ] is a diagram showing the voltage-current characteristics of light-emitting element 3. [ Fig.30 ] is a diagram showing the emission spectrum of light-emitting element 3. [Figure 31] 9-chloro-7H-benzo[c]carbazole 1 H-NMR spectrum. [Figure 32] PCcBCz 1 H-NMR spectrum. [Figure 33] PCcBCz-02 1 H-NMR spectrum. Modes for Carrying Out the Invention

[0023] The following is a detailed description of the embodiments of the present invention using the accompanying drawings. Note that the present invention is not limited to the following description, and its mode and details can be transformed into various forms without departing from the purpose and scope of the present invention. Therefore, the present invention should not be interpreted as being limited to the contents recorded in the embodiments shown below.

[0024] In addition, for ease of understanding, the position, size, range, etc. of each structure shown in the drawings and the like may not represent its actual position, size, range, etc. Therefore, the disclosed invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings and the like.

[0025] Note that in this specification and the like, when describing the configuration of the invention using drawings, reference numerals may be used in common to indicate the same components in different drawings.

[0026] (Implementation Method 1) In this embodiment, an organic compound which is one embodiment of the present invention is described.

[0027] The organic compound described in this embodiment has a structure including an anthracene skeleton and a carbazole skeleton represented by the following general formula (G1).

[0028] [Chemical formula 3]

[0029] Note that in the general formula (G1), Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R 1 To R 9 and R 11 To R 17 Each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of the rings may be a fused ring.

[0030] Note that in the above general formula (G1), when any of the substituted or unsubstituted arylene group having 6 to 13 carbon atoms, the substituted or unsubstituted carbazole skeleton, the substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, the substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and the substituted or unsubstituted aryl group having 6 to 13 carbon atoms has a substituent, the substituent may be alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl, cycloalkyl groups having 5 to 7 carbon atoms such as cyclopentyl, cyclohexyl, cycloheptyl, 1-bornyl and 2-bornyl, and aryl groups having 6 to 12 carbon atoms such as phenyl and biphenyl.

[0031] In addition, in the above general formula (G1), specific examples of substituted or unsubstituted aromatic groups having 6 to 13 carbon atoms include phenylene, 2,5-dimethyl-1,4-phenylene, naphthalene diyl, biphenyl diyl, 9,9-dimethylfluorene diyl, 9,9-diphenylfluorene diyl, 9,9'-spirobifluorene diyl, etc.

[0032] In addition, in the above general formula (G1), specific examples of substituted or unsubstituted carbazole skeletons include benzo[a]carbazole, benzo[b]carbazole, benzo[c]carbazole, dibenzo[a,c]carbazole, dibenzo[a,g]carbazole, dibenzo[c,g]carbazole, dibenzo[b,g]carbazole, naphtho[2,3-c]carbazole, naphtho[1,2-c]carbazole, etc.

[0033] In addition, in the above general formula (G1), specific examples of substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, hexyl, isohexyl, sec-hexyl, tert-hexyl, neohexyl, 3-methylpentyl, 2-methylpentyl, 2-ethylbutyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, and the like.

[0034] In addition, specific examples of substituted or unsubstituted aromatic groups having 6 to 13 carbon atoms in the above general formula (G1) include phenyl, naphthyl (1-naphthyl, 2-naphthyl), tolyl (o-tolyl, m-tolyl, p-tolyl), biphenyl (biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl), etc. The organic compound of one embodiment of the present invention represented by the general formula (G1) has an anthracene skeleton and a carbazole skeleton. Note that a plurality of materials have been developed as bipolar fluorescent host materials of organic compounds having an anthracene skeleton, but since the organic compound represented by the general formula (G1) has an anthracene skeleton and a carbazole skeleton, the organic compound represented by the general formula (G1) is a fluorescent host material exhibiting good hole (hole) transport properties compared to organic compounds composed only of an anthracene skeleton. In addition, the organic compound of one embodiment of the present invention shown in the general formula (G1) is a fluorescent host material having an anthracene skeleton and a bicarbazole skeleton. Note that in the case of such an organic compound, the organic compound in which the HOMO orbit is located in the bicarbazole skeleton tends to have a shallower HOMO energy level than the case in which the HOMO orbit is located in the anthracene skeleton. When such a fluorescent host material with a shallower HOMO energy level is used for the light-emitting layer, the difference between the HOMO energy level of the light-emitting layer and the HOMO energy level of the hole transport layer in contact with the light-emitting layer is reduced, thereby easing the injection barrier of holes from the hole transport layer to the light-emitting layer, and improving the injectability of holes from the hole transport layer to the light-emitting layer. Thus, it is possible to reduce the driving voltage or improve the luminous efficiency.

[0037] In addition, an organic compound of one embodiment of the present invention has an anthracene skeleton and a carbazole skeleton, and by setting the 3-position of the first phenylcarbazole bonded to the anthracene skeleton and the bonding position of the second phenylcarbazole to a desired position, the luminous efficiency or the reliability of the light-emitting element using the compound can be improved. Note that the bonding position of the second phenylcarbazole bonded to the 3-position of the first phenylcarbazole is preferably the 2-position of the second phenylcarbazole represented by the general formula (G1).

[0038] Next, specific structural formulas of the organic compounds according to one embodiment of the present invention are shown below. Note that the present invention is not limited thereto.

[0039] [Chemical formula 4]

[0040] [Chemical formula 5]

[0041] [Chemical formula 6]

[0042] [Chemical formula 7]

[0043] [Chemical formula 8]

[0044] [Chemical formula 9]

[0045] [Chemical formula 10]

[0046] [Chemical formula 11]

[0047] The organic compounds represented by the structural formulae (200) to (260) are examples of the organic compound represented by the general formula (G1), and the organic compound of one embodiment of the present invention is not limited thereto.

[0048] Next, an example of a method for synthesizing an organic compound represented by General Formula (G1) according to one embodiment of the present invention is described.

[0049] 《Method for synthesizing an organic compound represented by general formula (G1)》 First, an example of a method for synthesizing an organic compound represented by the following general formula (G1) is described.

[0050] [Chemical formula 12] In the general formula (G1), Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R 1 To R 9 and R 11 To R 17 Each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of the rings may be a fused ring.

[0052] The organic compound represented by the general formula (G1) can be synthesized by the synthesis scheme (A-1) shown below. That is, the organic compound represented by the general formula (G1) can be obtained by coupling a halogenated anthracene derivative (compound 1) and an organic boron compound or boric acid (compound 2) of a carbazole derivative or a fused polycyclic carbazole derivative using the Suzuki-Miyaura reaction.

[0053] [Chemical formula 13]

[0054] Note that in the above synthesis scheme (A-1), Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R 1 To R 9 and R 11 To R 17 Each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of them may be a fused ring. 50 and R 51 represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms. Note that R 50 and R 51 may be bonded to each other to form a ring. 1 represents a halogen or a triflate group.

[0055] As palladium catalysts that can be used in the above-mentioned synthesis scheme (A-1), palladium acetate (II), tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium (II) dichloride, etc. can be mentioned, but the palladium catalysts that can be used are not limited to this. As ligands of palladium catalysts that can be used in the synthesis scheme (A-1), tri (o-tolyl) phosphine, triphenylphosphine, tricyclohexylphosphine, etc. can be mentioned. However, the ligands of palladium catalysts that can be used are not limited to this. As bases that can be used in the synthesis scheme (A-1), organic bases such as sodium tert-butoxide, inorganic bases such as potassium carbonate and sodium carbonate, etc. can be mentioned, but the bases that can be used are not limited to this. As the solvent that can be used in the synthesis scheme (A-1), the following solvents can be cited: a mixed solvent of toluene and water; a mixed solvent of alcohols such as toluene and ethanol and water; a mixed solvent of xylene and water; a mixed solvent of alcohols such as xylene and ethanol and water; a mixed solvent of benzene and water; a mixed solvent of alcohols such as benzene and ethanol and water; a mixed solvent of ethers such as ethylene glycol dimethyl ether and water, etc. However, the solvent that can be used is not limited to this. In addition, preferably, a mixed solvent of toluene and water, or a mixed solvent of toluene, ethanol and water, or a mixed solvent of ethers such as ethylene glycol dimethyl ether and water.

[0056] In addition, as the compound 2 in the above-mentioned synthesis scheme (A-1), in addition to the organoboron compound or boric acid, an organoaluminum compound, an organozirconium compound, an organozinc compound, an organotin compound, etc. may be used.

[0057] In addition, as a coupling reaction other than the reaction shown in the synthesis scheme (A-1), the coupling reaction shown in the synthesis scheme (A-2) can be used. That is, in the coupling reaction shown in the synthesis scheme (A-2), the halogenated anthracene derivative (compound 3) and the carbazole derivative (compound 4) are coupled using a metal catalyst, a metal or a metal compound in the presence of a base, and an organic compound represented by the general formula (G1) can be obtained.

[0058] [Chemical formula 14]

[0059] Note that in the above synthesis scheme (A-2), Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and when the arylene group has a substituent, the substituents may be bonded to each other to form a ring. In addition, Cz represents a substituted or unsubstituted carbazole skeleton. In addition, R 1 To R 9 and R 11 To R 17 Each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 At least one of X may be a fused ring. 2 represents a halogen, and as the halogen, iodine, bromine and chlorine are more preferred.

[0060] In the case of the Hartwig-Buchwald reaction in the above-mentioned synthesis scheme (A-2), as palladium catalysts (II) that can be used, bis(dibenzylideneacetone)palladium(0), palladium acetate(II) and the like can be cited. Note that as ligands of the palladium catalyst that can be used in the synthesis scheme (A-2), tri(tert-butyl)phosphine, tri(n-hexyl)phosphine and tricyclohexylphosphine and the like can be cited. As bases that can be used in the synthesis scheme (A-2), organic bases such as sodium tert-butoxide, inorganic bases such as potassium carbonate and the like can be cited. In addition, as solvents that can be used in the synthesis scheme (A-2), toluene, xylene, benzene, tetrahydrofuran and the like can be cited. Note that in addition to the Hartwig-Buchwald reaction, the Ullmann reaction and the like can also be used, but are not limited to this.

[0061] Although the method for synthesizing the organic compound represented by the general formula (G1) according to one embodiment of the present invention has been described above, the present invention is not limited thereto, and the organic compound may be synthesized by other synthesis methods.

[0062] Because the organic compound of one embodiment of the present invention has electron transport and hole transport properties, it can be used as a main material of the light-emitting layer or for an electron transport layer or a hole transport layer. In addition, it is preferred to combine the organic compound of one embodiment of the present invention with a fluorescent substance (fluorescent material) and use it as a main material. In addition, since it exhibits fluorescent light emission, it can be directly used as a light-emitting substance of a light-emitting element. Therefore, a light-emitting element comprising these organic compounds is also included in the scope of one embodiment of the present invention.

[0063] In addition, by using the organic compound of one embodiment of the present invention, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high luminous efficiency can be realized. In addition, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with low power consumption can also be realized.

[0064] In this embodiment, one mode of the present invention is described. In addition, in other embodiments, one mode of the present invention will be described. However, one mode of the present invention is not limited to this. In other words, in this embodiment and other embodiments, various modes of the invention are recorded, so one mode of the present invention is not limited to a specific mode.

[0065] The structure described in this embodiment mode can be used in combination with the structures described in other embodiment modes as appropriate.

[0066] (Implementation Method 2) In this embodiment, refer to Figures 1A to 1E A light-emitting element using the organic compound described in Embodiment 1 will be described.

[0067] 《Basic structure of light-emitting elements》 First, the basic structure of a light emitting element will be described. Figure 1A A light-emitting element having an EL layer including a light-emitting layer between a pair of electrodes is shown. Specifically, the light-emitting element has a structure in which the EL layer 103 is sandwiched between a first electrode 101 and a second electrode 102 .

[0068] Figure 1B It is shown that there are multiple (in Figure 1B A light-emitting element having a stacked structure (tandem structure) including two EL layers (103a and 103b) and a charge generation layer 104 between the EL layers. A light-emitting element having a tandem structure can realize a light-emitting device that can be driven at a low voltage and consumes low power.

[0069] The charge generation layer 104 has a function of injecting electrons into one EL layer (103a or 103b) and injecting holes into the other EL layer (103b or 103a) when a voltage is applied to the first electrode 101 and the second electrode 102. Figure 1B In the embodiment, when a voltage is applied so that the potential of the first electrode 101 is higher than that of the second electrode 102, electrons and holes are injected from the charge generation layer 104 into the EL layer 103a and the EL layer 103b, respectively.

[0070] In terms of light extraction efficiency, the charge generation layer 104 preferably has light transmittance to visible light (specifically, the charge generation layer 104 has a visible light transmittance of 40% or more). The charge generation layer 104 can function even if its conductivity is lower than that of the first electrode 101 or the second electrode 102 .

[0071] Figure 1C FIG. 1 shows a stacked structure of the EL layer 103 of the light-emitting element of one embodiment of the present invention. Note that in this case, the first electrode 101 is used as an anode. The EL layer 103 has a structure in which a hole injection layer 111, a hole transport layer 112, a light-emitting layer 113, an electron transport layer 114, and an electron injection layer 115 are stacked in this order on the first electrode 101. Figure 1B When a plurality of EL layers are provided as in the tandem structure shown in the figure, the EL layers are stacked in order as described above from the anode side. When the first electrode 101 is a cathode and the second electrode 102 is an anode, the stacking order is reversed.

[0072] The light-emitting layer 113 in the EL layer (103, 103a, and 103b) can obtain fluorescent light and phosphorescent light of desired light color by appropriately combining light-emitting substances and multiple substances. In addition, the light-emitting layer 113 can also be a stacked structure with different light-emitting colors. In this case, different materials can be used as the light-emitting substances or other substances used in each stacked light-emitting layer. In addition, it is also possible to use Figure 1B The plurality of EL layers (103a and 103b) shown in the figure have a structure in which different luminescent colors are obtained. In this case, different materials may be used as the luminescent substance and other substances used in the respective luminescent layers.

[0073] In addition, in the light-emitting element of one embodiment of the present invention, for example, by using Figure 1C The first electrode 101 shown is a reflective electrode, the second electrode 102 is a semi-transmissive-semi-reflective electrode, and an optical microcavity resonator (microcavity) structure is adopted, so that the light obtained from the light-emitting layer 113 in the EL layer 103 can resonate between the above electrodes, thereby enhancing the light obtained through the second electrode 102.

[0074] In the case where the first electrode 101 of the light-emitting element is a reflective electrode composed of a laminated structure of a reflective conductive material and a light-transmitting conductive material (transparent conductive film), optical adjustment can be performed by adjusting the thickness of the transparent conductive film. Specifically, when the wavelength of light obtained from the light-emitting layer 113 is λ, it is preferred to adjust the inter-electrode distance between the first electrode 101 and the second electrode 102 to about mλ / 2 (note that m is a natural number).

[0075] In addition, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, it is preferable that the optical distance from the first electrode 101 to the region (light-emitting region) in the light-emitting layer 113 where the desired light can be obtained and the optical distance from the second electrode 102 to the region (light-emitting region) in the light-emitting layer 113 where the desired light can be obtained are adjusted to about (2m'+1)λ / 4 (note that m' is a natural number). Note that the "light-emitting region" described here refers to the region where holes and electrons in the light-emitting layer 113 recombine.

[0076] By performing the above optical adjustment, the spectrum of specific monochromatic light that can be obtained from the light-emitting layer 113 can be narrowed, thereby obtaining light emission with good color purity.

[0077] In addition, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 can be said to be the total thickness from the reflective region in the first electrode 101 to the reflective region in the second electrode 102. However, since it is difficult to accurately determine the positions of the reflective regions in the first electrode 101 and the second electrode 102, the above effect can be fully obtained by assuming that any position in the first electrode 101 and the second electrode 102 is a reflective region. In addition, strictly speaking, the optical distance between the first electrode 101 and the light-emitting layer that can obtain the desired light can be said to be the optical distance between the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that can obtain the desired light. However, since it is difficult to accurately determine the positions of the reflective region in the first electrode 101 and the light-emitting region in the light-emitting layer that can obtain the desired light, the above effect can be fully obtained by assuming that any position in the first electrode 101 is a reflective region and assuming that any position in the light-emitting layer that can obtain the desired light is a light-emitting region.

[0078] Figure 1C The light-emitting element shown has a microcavity structure, so even if the same EL layer is used, light of different wavelengths (monochromatic light) can be extracted. As a result, it is not necessary to coat separately (for example, coating as R, G, B) to obtain different luminous colors. As a result, high resolution is easily achieved. In addition, it can be combined with a coloring layer (color filter). In addition, the luminous intensity in the front direction with a specific wavelength can be enhanced, thereby achieving low power consumption.

[0079] Figure 1E The light emitting element shown is Figure 1B An example of a light-emitting element of a tandem structure shown in the figure has a structure in which three EL layers (103a, 103b, 103c) are stacked with charge generation layers (104a, 104b) sandwiched therebetween. The three EL layers (103a, 103b, 103c) respectively include light-emitting layers (113a, 113b, 113c), and the light-emitting colors of each light-emitting layer can be freely combined. For example, the light-emitting layer 113a and the light-emitting layer 113c can exhibit blue, and the light-emitting layer 113b can exhibit one of red, green, and yellow. In addition, for example, the light-emitting layer 113a and the light-emitting layer 113c can exhibit red, and the light-emitting layer 113b can exhibit one of blue, green, and yellow.

[0080] In addition, in the light-emitting element of one embodiment of the present invention, at least one of the first electrode 101 and the second electrode 102 is a light-transmitting electrode (transparent electrode, semi-transmitting-semi-reflecting electrode, etc.). In the case where the light-transmitting electrode is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or more. In addition, in the case where the electrode is a semi-transmitting-semi-reflecting electrode, the visible light reflectance of the semi-transmitting-semi-reflecting electrode is 20% or more and 80% or less, preferably 40% or more and 70% or less. In addition, the resistivity of these electrodes is preferably 1×10 -2 Ωcm or less.

[0081] In the light-emitting element of one embodiment of the present invention, when one of the first electrode 101 and the second electrode 102 is a reflective electrode (reflective electrode), the reflective electrode has a visible light reflectivity of 40% to 100%, preferably 70% to 100%. In addition, the resistivity of the electrode is preferably 1×10 -2 Ωcm or less.

[0082] 《Specific structure and manufacturing method of light-emitting element》 Next, refer to Figures 1A to 1E The specific structure and manufacturing method of the light emitting element of one embodiment of the present invention are described. Figure 1D Description Figure 1B The light-emitting element with a series structure and a microcavity structure is shown. Figure 1D In the case where the light-emitting element shown has a microcavity structure, a reflective electrode is formed as the first electrode 101, and a semi-transmissive-semi-reflective electrode is formed as the second electrode 102. Thus, the electrodes can be formed in a single layer or in a stacked layer using a desired electrode material alone or using a plurality of electrode materials. In addition, the second electrode 102 is formed by selecting a material in the same manner as described above after the EL layer 103b is formed. In addition, the electrodes can be formed by sputtering or vacuum evaporation.

[0083] <First Electrode and Second Electrode> As the material forming the first electrode 101 and the second electrode 102, if the functions of the above two electrodes can be satisfied, the following materials can be appropriately combined. For example, metals, alloys, conductive compounds and mixtures thereof can be appropriately used. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (also called ITSO), In-Zn oxide, In-W-Zn oxide can be cited. In addition to the above, aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), neodymium (Nd) and other metals and alloys appropriately combined therewith can also be cited. In addition to the above, elements belonging to Group 1 or Group 2 of the periodic table (for example, lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr)), rare earth metals such as europium (Eu), ytterbium (Yb), alloys appropriately combined therefrom, and graphene, etc. can be used.

[0084] exist Figure 1D In the light-emitting element shown in the figure, when the first electrode 101 is an anode, the hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are sequentially stacked on the first electrode 101 by vacuum evaporation. After the EL layer 103a and the charge generation layer 104 are formed, the hole injection layer 111b and the hole transport layer 112b of the EL layer 103b are sequentially stacked on the charge generation layer 104 in the same manner as described above.

[0085] <Hole Injection Layer and Hole Transport Layer> The hole injection layer (111, 111a, 111b) is a layer that injects holes from the anode first electrode 101 and the charge generation layer 104 into the EL layer (103, 103a, 103b), and contains a material with high hole injection properties.

[0086] As materials with high hole injection properties, transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide can be cited. In addition to the above, phthalocyanine compounds such as phthalocyanine (abbreviated as: H2Pc), copper phthalocyanine (CuPC), etc.; aromatic amine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as: DNTPD), etc.; or polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviated as: PEDOT / PSS), etc. can be used.

[0087] As a material with high hole injection property, a composite material including a hole transport material and an acceptor material (electron acceptor material) can also be used. In this case, the acceptor material extracts electrons from the hole transport material to generate holes in the hole injection layer (111, 111a, 111b), and the holes are injected into the light-emitting layer (113, 113a, 113b) through the hole transport layer (112, 112a, 112b). In addition, the hole injection layer (111, 111a, 111b) can be a single layer composed of a composite material including a hole transport material and an acceptor material (electron acceptor material), or a stack of layers formed using a hole transport material and an acceptor material (electron acceptor material) respectively.

[0088] The hole transport layer (112, 112a, 112b) is a layer that transports holes injected from the first electrode 101 and the charge generation layer 104 through the hole injection layer (111, 111a, 111b) to the light-emitting layer (113, 113a, 113b). In addition, the hole transport layer (112, 112a, 112b) is a layer containing a hole transport material. As the hole transport material used for the hole transport layer (112, 112a, 112b), it is particularly preferred to use a material having a HOMO energy level that is the same as or close to the HOMO energy level of the hole injection layer (111, 111a, 111b).

[0089] As an acceptor material for the hole injection layer (111, 111a, 111b), an oxide of a metal belonging to Group 4 to Group 8 in the periodic table can be used. Specifically, molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide can be cited. Molybdenum oxide is particularly preferably used because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle. In addition to the above, organic acceptors such as quinone dimethane derivatives, tetrachlorobenzoquinone derivatives, and hexaazatriphenylene derivatives can be cited. Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviated as: HAT-CN) and the like can be used. In particular, compounds such as HAT-CN, which have a fused aromatic ring with multiple heteroatoms and bonded to an electron-withdrawing group, are thermally stable and therefore are preferred. In addition, [3]radialene derivatives containing electron-withdrawing groups (especially halogen groups such as fluorine groups and cyano groups) are particularly preferred because they have very high electron accepting properties. Specifically, they include: α, α', α"-1,2,3-cyclopropane trimethylene tris[4-cyano-2,3,5,6-tetrafluorophenylacetonitrile], α, α', α"-1,2,3-cyclopropane trimethylene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenylacetonitrile], α, α', α"-1,2,3-cyclopropane trimethylene tris[2,3,4,5,6-pentafluorophenylacetonitrile], etc.

[0090] As the hole transport material used for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 112b), it is preferable to have 10 -6 cm 2 In addition, any substance other than the above may be used as long as the hole transport property is higher than the electron transport property.

[0091] As hole transport materials, it is preferred to use π-electron-rich heteroaromatic compounds (for example, carbazole derivatives or indole derivatives) or aromatic amine compounds, and specific examples are as follows: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as: TPD), 4,4'-bis[N-(spiro-9,9'-bifluorene-2 -yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[4-(9-phenanthrenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazole-3-amine (abbreviated as: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]- 9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl] Compounds having an aromatic amine skeleton such as 1,3-bis(N-carbazolyl)benzene (abbreviated as mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviated as CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviated as CzTP), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA) and the like; 4,4',4"-(benzene-1,3 The invention also includes compounds having a thiophene skeleton, such as 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), and 4-[4-(9-phenyl-9H-fluorene-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV); and compounds having a furan skeleton, such as 4,4',4"-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), and 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).

[0092] Furthermore, high molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD) can also be used.

[0093] Note that the hole transport material is not limited to the above materials, and a combination of one or more of various known materials can be used as a hole transport material for the hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 112b). In addition, the hole transport layer (112, 112a, 112b) can also be composed of a plurality of layers. That is, for example, a first hole transport layer and a second hole transport layer can also be stacked.

[0094] exist Figure 1D In the light-emitting element shown, the light-emitting layer 113a is formed on the hole-transporting layer 112a in the EL layer 103a by vacuum evaporation. After the EL layer 103a and the charge-generating layer 104 are formed, the light-emitting layer 113b is formed on the hole-transporting layer 112b in the EL layer 103b by vacuum evaporation.

[0095] <Luminous Layer> The light-emitting layer (113, 113a, 113b, 113c) is a layer containing a light-emitting substance. In addition, as the light-emitting substance, a substance that emits light of blue, purple, blue-purple, green, yellow-green, yellow, orange, red, etc. is appropriately used. In addition, by using different light-emitting substances in a plurality of light-emitting layers (113a, 113b, 113c), a structure that emits different light colors can be obtained (for example, light-emitting colors in a complementary color relationship can be combined to obtain white light). Furthermore, a stacked structure in which one light-emitting layer contains different light-emitting substances can also be used.

[0096] In addition, the light-emitting layer (113, 113a, 113b, 113c) may include one or more organic compounds (host material, auxiliary material) in addition to the light-emitting substance (guest material). In addition, as the one or more organic compounds, one or both of the hole transport material and the electron transport material described in this embodiment can be used.

[0097] In addition, as the light-emitting material that can be used for the light-emitting layer (113, 113a, 113b, 113c), a light-emitting material that converts singlet excitation energy into light in the visible light region or a light-emitting material that converts triplet excitation energy into light in the visible light region can be used.

[0098] In addition, as other light-emitting substances, for example, the following substances can be mentioned.

[0099] As the luminescent substance that converts the singlet excitation energy into luminescence, there can be mentioned substances that emit fluorescence (fluorescent materials), for example, pyrene derivatives, anthracene derivatives, triphenylene derivatives, fluorene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, phenanthrene derivatives, naphthalene derivatives, etc. In particular, pyrene derivatives are preferred because of their high luminescence quantum yield. Specific examples of pyrene derivatives include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N,N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bis(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N' -diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), etc.

[0100] In addition to the above, 5,6-bis[4-(10-phenyl-9-anthracenyl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-anthracenyl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: PAP2BPy) can be used. : YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviated as: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-diphenyl-2-anthracenyl)triphenylamine (abbreviated as: 2YGAPPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: PCAPA), 4-(10- triphenylamine (PCBAPA), 4-[4-(10-phenyl-9-anthracenyl)phenyl]-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBAPBA), perylene, 2,5,8,11-tetra-(tert-butyl) perylene (TBP), N,N"-(2-tert-butylanthracene-9,10-diyldiphenylamine -4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviated as: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviated as: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthracenyl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPAPPA), etc.

[0101] Examples of the light-emitting substance that converts triplet excitation energy into light emission include substances that emit phosphorescence (phosphorescent materials) and thermally activated delayed fluorescence (TADF) materials that exhibit thermally activated delayed fluorescence.

[0102] Examples of phosphorescent materials include organic metal complexes, metal complexes (platinum complexes), rare earth metal complexes, etc. Since these substances each exhibit a different emission color (emission peak), they are appropriately selected according to the needs.

[0103] Examples of phosphorescent materials that exhibit blue or green color and have an emission spectrum with a peak wavelength of 450 nm to 570 nm include the following.

[0104] 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-triazole)iridium(III) (abbreviation: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazole]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazole]iridium(III) (abbreviation: [Ir(iPrptz-3b)3], II) (abbreviated as [Ir(iPr5btz)3]), etc. having a 4H-triazole skeleton; tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole]iridium(III) (abbreviated as [Ir(Mptz1-mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazole)iridium(III) (abbreviated as [Ir(Prptz1-Me)3]), etc. having a 1H-triazole skeleton; fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviated as [Ir(iPrpmi)3]), tris[3- (2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviated as [Ir(dmpimpt-Me)3]) and other organic metal complexes having an imidazole skeleton; and bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2' ]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2' ]iridium(III) picolinate (abbreviated as FIrpic), bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinium-N,C 2' Iridium(III) picolinate (abbreviated as [Ir(CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyridinium-N,C 2' ]Organometallic complexes with phenylpyridine derivatives having electron-withdrawing groups as ligands, such as iridium (III) acetylacetonate (abbreviation: FIr(acac)).

[0105] Examples of phosphorescent materials that exhibit green or yellow color and have an emission spectrum with a peak wavelength of 495 nm to 590 nm include the following.

[0106] For example, tris(4-methyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-tert-butyl-6-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonate)bis(6-methyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (acetylacetonate)bis(6-tert-butyl-4-phenylpyrimidinyl)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (acetylacetonate)bis(6-(2-norbornyl)-4-phenylpyrimidinyl]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (acetylacetonate)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinyl]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ac)]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviated as [Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4,6-diphenylpyrimidinyl)iridium(III) (abbreviated as [Ir(dppm)2(acac)]), etc.; (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazine)iridium(III) (abbreviated as [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazine)iridium(III) (abbreviated as [Ir(mppr-iPr)2(acac)]), etc.; tri(2-phenylpyridinium-N,C 2' )iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinium-N,C 2' )iridium(III)acetylacetonate (abbreviated as [Ir(ppy)2(acac)]), bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as [Ir(bzq)2(acac)]), tris(benzo[h]quinoline)iridium(III) (abbreviated as [Ir(bzq)3]), tris(2-phenylquinoline-N,C 2′ )iridium(III) (abbreviation: [Ir(pq)3]), bis(2-phenylquinoline-N,C 2' ) iridium (III) acetylacetonate (abbreviated as [Ir(pq)2(acac)]), etc., organic metal iridium complexes with pyridine skeleton; bis(2,4-diphenyl-1,3-oxazole-N,C 2' ) iridium (III) acetylacetonate (abbreviated as [Ir(dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridine-N,C 2'Iridium(III) acetylacetonate (abbreviated as [Ir(p-PF-ph)2(acac)]), bis(2-phenylbenzothiazole-N,C 2' ) organic metal complexes such as iridium (III) acetylacetonate (abbreviated as [Ir(bt)2(acac)]), and rare earth metal complexes such as tris(acetylacetonate)(monophenanthroline)terbium (III) (abbreviated as [Tb(acac)3(Phen)]).

[0107] Examples of phosphorescent materials that exhibit yellow or red color and have an emission spectrum with a peak wavelength of 570 nm to 750 nm include the following.

[0108] For example, (diisobutyrylmethane)bis[4,6-bis(3-methylphenyl)pyrimidinyl]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinyl](dipivaloylmethane)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (dipivaloylmethane)bis[4,6-di(naphthalen-1-yl)pyrimidinyl]iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]) and the like can be mentioned. Organic metal complexes with pyrimidine skeletons; (acetylacetonato)bis(2,3,5-triphenylpyrazine)iridium(III) (abbreviated as [Ir(tppr)2(acac)]), bis(2,3,5-triphenylpyrazine)(dipivaloylmethane)iridium(III) (abbreviated as [Ir(tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedione-κ 2 O, O') iridium (III) (abbreviated as [Ir(dmdppr-P)2(dibm)]), bis{4,6-dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptanedione-κ 2 O, O') iridium (III) (abbreviated as [Ir(dmdppr-dmCP)2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalinato]-N, C 2’ ]iridium (III) (abbreviation: [Ir(mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoxalinato)-N,C 2’]iridium (III) (abbreviated as [Ir(dpq)2(acac)]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium (III) (abbreviated as [Ir(Fdpq)2(acac)]) and other organic metal complexes with a pyrazine skeleton; tris(1-phenylisoquinoline-N,C 2’ )iridium(III) (abbreviated as [Ir(piq)3]), bis(1-phenylisoquinoline-N,C 2' ) iridium (III) acetylacetonate (abbreviated as [Ir(piq)2(acac)]) and other organic metal complexes having a pyridine skeleton; 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum (II) (abbreviated as [PtOEP]) and other platinum complexes; and tris(1,3-diphenyl-1,3-propanedione (propanedionato))(monophenanthroline)europium (III) (abbreviated as [Eu(DBM)3(Phen)]), tris[1-(2-thiophenoyl)-3,3,3-trifluoroacetone](monophenanthroline)europium (III) (abbreviated as [Eu(TTA)3(Phen)] and other rare earth metal complexes.

[0109] As the organic compound (host material, auxiliary material) used for the light-emitting layer (113, 113a, 113b, 113c), one or more substances having a larger energy gap than the light-emitting substance (guest material) can be used.

[0110] When the luminescent material is a fluorescent material, it is preferred to use an organic compound with a large energy level of a singlet excited state and a small energy level of a triplet excited state as a host material. For example, an anthracene derivative or a tetracene derivative is preferably used. Specifically, 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as: CzPA), 7-[4-(10-phenyl-9-anthracenyl)phenyl]-7H-dibenzo[c , g] carbazole (abbreviated as: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthracenyl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviated as: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl-9H-fluorene-9-yl)-biphenyl-4'-yl}-anthracene (abbreviated as: FLPPA), 5,12-diphenyl tetracene, 5,12-bis(biphenyl-2-yl) tetracene, etc.

[0111] In the case where the luminescent material is a phosphorescent material, an organic compound whose triplet excitation energy is larger than the triplet excitation energy (energy difference between the ground state and the triplet excited state) of the luminescent material is selected as the host material. In this case, zinc or aluminum metal complexes, oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline derivatives, aromatic amines, carbazole derivatives, etc. can be used.

[0112] More specifically, as the host material, for example, the following hole transporting materials and electron transporting materials can be used.

[0113] As the main materials with high hole transport properties, for example, aromatic amine compounds can be mentioned, such as N,N'-di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviated as: DTDPPA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as: DPA3B), etc.

[0114] In addition, carbazole derivatives such as 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviated as PCzTPN2), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1), etc. can also be mentioned. Examples of carbazole derivatives include 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), and 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene.

[0115] In addition, as a host material with high hole transport properties, for example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4',4"-tri(carbazol-9-yl)triphenylamine (abbreviated as TCTA), 4,4',4"-tri[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviated as 1-TNATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4"-tri[N-(3- triphenylamine (abbreviation: m-MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL), N-( 9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4"-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4"-(9-phenyl-9H -carbazole-3-yl) triphenylamine (abbreviation: PCBNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazole-3-yl)amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazole-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N"-triphenyl-N,N',N"-tri(9-phenylcarbazole-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4- 9,9-dimethyl-9H-fluoren-2-amine (PCBBiF), 9,9-dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (PCBASF), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamine

[0063] Aromatic amine compounds such as N,N'-bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F) and the like. In addition, 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 3-[4-(9-phenanthrenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 3,6-bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), 4,4',4"-(benzene-1,3,5- Carbazole compounds, thiophene compounds, furan compounds, fluorene compounds, triphenylene compounds, phenanthrene compounds, etc. are included.

[0116] As a host material with high electron transport properties, metal complexes having a quinoline skeleton or a benzoquinoline skeleton can be cited, for example: tris(8-hydroxyquinoline)aluminum(III) (abbreviated as: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as: Znq), etc. In addition, metal complexes having oxazolyl-type or thiazole-type ligands such as bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as: ZnPBO) and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as: ZnBTZ) can also be used. Furthermore, in addition to the metal complex, oxadiazole derivatives such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl]-9H-carbazole (abbreviation: CO11); triazole derivatives such as 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ); 2,2',2"-(1,3,5-phenyltriyl)tri(1-phenyl- Compounds having an imidazole skeleton (especially benzimidazole derivatives) such as 1H-benzimidazole (abbreviated as TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II); compounds having an oxazole skeleton (especially benzoxazole derivatives) such as 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs); phenanthroline derivatives such as bathophenanthroline (abbreviated as Bphen), bathocuproin (abbreviated as BCP), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviated as NBphen); 2-[3-(1H-benzimidazole)-1H-benzimidazole (abbreviated as TPBI), 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviated as mDBTBIm-II); compounds having an oxazole skeleton (especially benzoxazole derivatives) such as 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs); 2-[(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2- [4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm) and the like; 2-{4-[3-(N-phenyl-9H- Heterocyclic compounds having a triazine skeleton, such as 3,5-bis[3-(9H-carbazole-9-yl)phenyl]pyridine (abbreviated as 35DCzPPy) and 1,3,5-tris[3-(3-pyridyl)phenyl]benzene (abbreviated as TmPyPB). In addition, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.

[0117] In addition, examples of the host material include anthracene derivatives, phenanthrene derivatives, pyrene derivatives, Derivatives, dibenzo[g,p] Condensed polycyclic aromatic compounds such as derivatives. Specifically, 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), 2PCAPA, 6,12-dimethoxy-5,11-diphenyl DBC1, 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as: t-BuDNA), 9,9'-bianthracene (abbreviated as: BANT), 9,9'-(stilbene-3,3'-diyl)phenanthrene (abbreviated as: DPNS), 9,9'-(stilbene-4,4'-diyl)phenanthrene (abbreviated as: DPNS2) and 1,3,5-tri(1-pyrenyl)benzene (abbreviated as: TPB3), etc.

[0118] In addition, when a plurality of organic compounds are used for the light-emitting layer (113, 113a, 113b, 113c), two compounds (a first compound and a second compound) and an organic metal complex that form an exciplex may also be combined. In this case, various organic compounds may be appropriately combined, but in order to efficiently form an exciplex, it is particularly preferred to combine a compound that easily receives holes (hole transport material) and a compound that easily receives electrons (electron transport material). In addition, as specific examples of hole transport materials and electron transport materials, the materials shown in this embodiment can be used. By adopting the above structure, high efficiency, low voltage and long life can be achieved at the same time.

[0119] TADF material refers to a material that can use tiny thermal energy to up-convert the triplet excited state to the singlet excited state (reverse intersystem crossing) and efficiently emit luminescence (fluorescence) from the singlet excited state. As a condition for efficiently obtaining thermally activated delayed fluorescence, for example, the energy difference between the triplet excited energy level and the singlet excited energy level can be 0 eV or more and 0.2 eV or less, preferably 0 eV or more and 0.1 eV or less. The delayed fluorescence emitted by the TADF material refers to luminescence with the same spectrum as general fluorescence but with a very long lifetime. Its lifetime is 10 -6More than 10 seconds, preferably 10 -3 seconds or more.

[0120] Examples of TADF materials include fullerene or its derivatives, acridine derivatives such as prussicin, eosin, etc. In addition, metal-containing porphyrins including magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd) can be cited. As metal-containing porphyrins, for example, protoporphyrin-tin fluoride complex (abbreviated as: SnF2(ProtoIX)), mesoporphyrin-tin fluoride complex (abbreviated as: SnF2(Meso IX)), hematoporphyrin-tin fluoride complex (abbreviated as: SnF2(Hemato IX)), coproporphyrin tetramethyl ester-tin fluoride complex (abbreviated as: SnF2(Copro III-4Me)), octaethylporphyrin-tin fluoride complex (abbreviated as: SnF2(OEP)), protoporphyrin-tin fluoride complex (abbreviated as: SnF2(Etio I)) and octaethylporphyrin-platinum chloride complex (abbreviated as: PtCl2OEP) can also be mentioned.

[0121] In addition to the above, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazole-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazole-3-yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl- The invention relates to heterocyclic compounds having π-electron-rich aromatic heterocycles and π-electron-deficient aromatic heterocycles, such as 3-(9,9-dimethyl-9H-acridin-10-yl)-9H-oxanthene-9-one (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroacridinium)phenyl]sulfone (abbreviation: DMAC-DPS), and 10-phenyl-10H,10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA). In addition, in a substance in which a π-electron-rich aromatic heterocycle and a π-electron-deficient aromatic heterocycle are directly bonded, the donor property of the π-electron-rich aromatic heterocycle and the acceptor property of the π-electron-deficient aromatic heterocycle are both strong, and the energy difference between the singlet excited state and the triplet excited state becomes small, so it is particularly preferred.

[0122] In addition, when using a TADF material, it can be combined with other organic compounds.

[0123] exist Figure 1DIn the light-emitting element shown, the electron-transporting layer 114a is formed on the light-emitting layer 113a in the EL layer 103a by vacuum evaporation. After the EL layer 103a and the charge-generating layer 104 are formed, the electron-transporting layer 114b is formed on the light-emitting layer 113b in the EL layer 103b by vacuum evaporation.

[0124] <Electron Transport Layer> The electron transport layer (114, 114a, 114b) is a layer that transports electrons injected from the second electrode 102 or the charge generation layer (104) through the electron injection layer (115, 115a, 115b) to the light-emitting layer (113, 113a, 113b). The electron transport layer (114, 114a, 114b) is a layer containing an electron transport material. The electron transport material used for the electron transport layer (114, 114a, 114b) preferably has a molecular weight of 1×10 -6 cm 2 In addition, any substance other than the above may be used as long as the electron transport property is higher than the hole transport property.

[0125] Examples of electron transporting materials include metal complexes having quinoline ligands, benzoquinoline ligands, oxazole ligands, thiazole ligands, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, pyridine derivatives, bipyridine derivatives, etc. In addition to the above, π-electron-deficient heteroaromatic compounds such as nitrogen-containing heteroaromatic compounds can also be used.

[0126] Specifically, metal complexes such as Alq3, tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]-quinoline)beryllium (abbreviated as BeBq2), BAlq, bis[2-(2-hydroxyphenyl)benzoxazole]zinc(II) (abbreviated as Zn(BOX)2), bis[2-(2-hydroxyphenyl)benzothiazole]zinc(II) (abbreviated as Zn(BTZ)2), 2-(4-biphenyl)benzothiazole)zinc(II) (abbreviated as Zn(BTZ)2) and the like can be used. 1,2,4-triazole (abbreviated as p-EtTAZ), 3-(4-tert-butylphenyl)-4-phenyl-5-(4"-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), 3-(4-tert-butylphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), OXD-7, 3-(4'-tert-butylphenyl)-4-phenyl-5-(4"-biphenylyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as Bphen), bathocuproin (abbreviated as Bphen), heteroaromatic compounds such as 4,4'-bis(5-methylbenzothiophene-2-yl)phenylethylene (abbreviated as BzOs), 2-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTPDBq-II), 2-[3'-(dibenzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviated as 2mDBTBPDBq-II), 2-[4-(3,6 -diphenyl-9H-carbazole-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 2CzPDBq-III), 7-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 7mDBTPDBq-II) and 6-[3-(dibenzothiophene-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviated as: 6mDBTPDBq-II) and other quinoxaline derivatives or dibenzoquinoxaline derivatives.

[0127] In addition, polymer compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can also be used.

[0128] In addition, the electron transport layer (114, 114a, 114b) may be a single layer or a stack of two or more layers containing the above-mentioned substances.

[0129] exist Figure 1DIn the light-emitting element shown, the electron injection layer 115a is formed on the electron transport layer 114a in the EL layer 103a by vacuum evaporation. Then, the EL layer 103a and the charge generation layer 104 are formed, and the electron injection layer 115b is formed by vacuum evaporation after the electron transport layer 114b in the EL layer 103b is formed.

[0130] <Electron Injection Layer> The electron injection layer (115, 115a, 115b) is a layer containing a substance with high electron injection properties. As the electron injection layer (115, 115a, 115b), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2) and lithium oxide (LiO x ) or other alkali metals, alkaline earth metals, or compounds of these metals. In addition, rare earth metal compounds such as erbium fluoride (ErF3) can be used. In addition, electron salts can also be used for the electron injection layer (115, 115a, 115b). As electron salts, for example, substances that add electrons to a mixed oxide of calcium and aluminum at a high concentration can be cited. In addition, the substances that constitute the electron transport layer (114, 114a, 114b) as described above can also be used.

[0131] In addition, a composite material formed by mixing an organic compound with an electron donor (donor) can also be used for the electron injection layer (115, 115a, 115b). This composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material with excellent performance in transporting the generated electrons. Specifically, for example, an electron transport material (metal complex, heteroaromatic compound, etc.) used for the electron transport layer (114, 114a, 114b) as described above can be used. As an electron donor, any substance that exhibits electron donating properties to organic compounds can be used. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferably used, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be mentioned. In addition, alkali metal oxides or alkaline earth metal oxides are preferably used, and lithium oxide, calcium oxide, barium oxide, etc. can be mentioned. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[0132] For example, in the case of amplifying light obtained from the light-emitting layer 113b, it is preferable to form the second electrode 102 and the light-emitting layer 113b in such a manner that the optical distance between the second electrode 102 and the light-emitting layer 113b is less than λ / 4 with respect to the wavelength of light emitted by the light-emitting layer 113b. In this case, the optical distance can be adjusted by changing the thickness of the electron transport layer 114b or the electron injection layer 115b.

[0133] <Charge Generation Layer> The charge generation layer 104 has the function of injecting electrons into the EL layer 103a and injecting holes into the EL layer 103b when a voltage is applied between the first electrode 101 (anode) and the second electrode 102 (cathode). The charge generation layer 104 may have a structure in which an electron acceptor (acceptor) is added to a hole transport material, or a structure in which an electron donor (donor) is added to an electron transport material. Alternatively, these two structures may be stacked. In addition, by using the above-mentioned materials to form the charge generation layer 104, the increase in the driving voltage when the EL layer is stacked can be suppressed.

[0134] In the case where the charge generation layer 104 has a structure in which an electron acceptor is added to a hole transport material, the material described in this embodiment can be used as the hole transport material. In addition, as the electron acceptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviated as: F4-TCNQ), chloranil, etc. can be cited. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be cited. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, etc. can be cited.

[0135] In the case where the charge generation layer 104 has a structure in which an electron donor is added to an electron transport material, the material shown in this embodiment can be used as an electron transport material. In addition, as an electron donor, an alkali metal, an alkaline earth metal, a rare earth metal, or a metal belonging to Group 2 or Group 13 in the periodic table and their oxides or carbonates can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, etc. are preferably used. In addition, organic compounds such as tetrathianaphthacene can also be used as electron donors.

[0136] Figure 1E The EL layer 103c in the embodiment may have the same structure as the above-mentioned EL layers (103, 103a, 103b). The charge generation layers 104a and 104b may have the same structure as the above-mentioned charge generation layer 104.

[0137] <Substrate> The light-emitting element shown in this embodiment can be formed on various substrates. Note that there is no particular limitation on the type of substrate. As an example of the substrate, a semiconductor substrate (for example, a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate including a stainless steel foil, a tungsten substrate, a substrate including a tungsten foil, a flexible substrate, a laminated film, a paper or a substrate film including a fibrous material, etc. can be cited.

[0138] Examples of glass substrates include barium borosilicate glass, aluminoborosilicate glass, soda-lime glass, etc. Examples of flexible substrates, laminated films, base films, etc. include plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES), synthetic resins such as acrylic resins, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyamide, polyimide, aramid, epoxy, inorganic vapor-deposited films, and paper.

[0139] In addition, when manufacturing the light-emitting element shown in this embodiment, a vacuum process such as evaporation or a solution process such as spin coating or inkjet can be used. As the evaporation method, a physical evaporation method (PVD method) such as sputtering, ion plating, ion beam evaporation, molecular beam evaporation, vacuum evaporation or a chemical vapor deposition method (CVD method) can be used. In particular, the functional layers (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)) and charge generation layer (104, 104a, 104b)) included in the EL layer of the light-emitting element can be formed by a method such as a vapor deposition method (vacuum vapor deposition method), a coating method (dip coating method, dye coating method, rod coating method, spin coating method, spray coating method, etc.), a printing method (inkjet method, screen printing (stencil printing) method, offset printing (lithography) method, flexographic printing (letterpress printing) method, gravure printing method, microcontact printing method, etc.).

[0140] In addition, the materials of the functional layers (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) and charge generation layer (104, 104a, 104b)) constituting the EL layer (103, 103a, 103b) of the light-emitting element shown in this embodiment are not limited thereto, and any material that can satisfy the functions of each layer can be used in combination. As an example, a polymer compound (oligomer, dendrimer, polymer, etc.), a medium molecular compound (a compound between a low molecule and a high molecule: a molecular weight of 400 to 4000), an inorganic compound (quantum dot material, etc.), etc. can be used. As the quantum dot material, a colloidal quantum dot material, an alloy type quantum dot material, a core shell type quantum dot material, a core type quantum dot material, or the like can be used.

[0141] The structure described in this embodiment mode can be used in combination with the structures described in other embodiment modes as appropriate.

[0142] (Implementation method 3) In this embodiment, a light-emitting device which is one embodiment of the present invention is described. Figure 2A The light-emitting device shown is an active matrix light-emitting device in which a transistor (FET) 202 and light-emitting elements (203R, 203G, 203B, 203W) formed on a first substrate 201 are electrically connected, a plurality of light-emitting elements (203R, 203G, 203B, 203W) share an EL layer 204, and a microcavity structure is used in which the optical distance between electrodes of each light-emitting element is adjusted according to the color of light emitted by each light-emitting element. In addition, a top emission light-emitting device is used in which light emitted from the EL layer 204 is emitted through a color filter (206R, 206G, 206B) formed on a second substrate 205.

[0143] exist Figure 2A In the light-emitting device shown, the first electrode 207 is used as a reflective electrode, and the second electrode 208 is used as a semi-transmissive-semi-reflective electrode. As electrode materials for forming the first electrode 207 and the second electrode 208, they can be used appropriately with reference to other embodiments.

[0144] In addition, Figure 2A For example, when the light emitting element 203R is used as a red light emitting element, the light emitting element 203G is used as a green light emitting element, the light emitting element 203B is used as a blue light emitting element, and the light emitting element 203W is used as a white light emitting element, Figure 2B As shown, the distance between the first electrode 207 and the second electrode 208 in the light emitting element 203R is adjusted to the optical distance 200R, the distance between the first electrode 207 and the second electrode 208 in the light emitting element 203G is adjusted to the optical distance 200G, and the distance between the first electrode 207 and the second electrode 208 in the light emitting element 203B is adjusted to the optical distance 200B. Figure 2B As shown, optical adjustment can be performed by stacking the conductive layer 207R on the first electrode 207 of the light-emitting element 203R and stacking the conductive layer 207G on the first electrode 207 of the light-emitting element 203G.

[0145] Color filters (206R, 206G, 206B) are formed on the second substrate 205. The color filters transmit visible light in a specific wavelength range and block visible light in a specific wavelength range. Figure 2AAs shown, by setting a color filter 206R that transmits only the red wavelength range at a position overlapping with the light-emitting element 203R, red light can be obtained from the light-emitting element 203R. In addition, by setting a color filter 206G that transmits only the green wavelength range at a position overlapping with the light-emitting element 203G, green light can be obtained from the light-emitting element 203G. In addition, by setting a color filter 206B that transmits only the blue wavelength range at a position overlapping with the light-emitting element 203B, blue light can be obtained from the light-emitting element 203B. Note that the light-emitting element 203W can obtain white light without setting a filter. In addition, a black layer (black matrix) 209 can also be provided at the end of each color filter. Furthermore, the color filters (206R, 206G, 206B) or the black layer 209 can also be covered by a protective layer composed of a transparent material.

[0146] Although in Figure 2A FIG. 2 shows a light emitting device having a structure (top emission type) in which light is extracted on the second substrate 205 side, but a structure such as Figure 2C As shown in FIG. 1 , a light emitting device (bottom emission type) is configured to extract light from the first substrate 201 side on which the FET 202 is formed. In the bottom emission type light emitting device, the first electrode 207 is used as a semi-transmissive-semi-reflective electrode, and the second electrode 208 is used as a reflective electrode. In addition, as the first substrate 201, at least a light-transmitting substrate is used. In addition, as shown in FIG. Figure 2C As shown, the color filters (206R', 206G', 206B') may be disposed on a side closer to the first substrate 201 than the light emitting elements (203R, 203G, 203B).

[0147] In addition, although Figure 2A In the figure, the light-emitting element is a red light-emitting element, a green light-emitting element, a blue light-emitting element, and a white light-emitting element, but the light-emitting element of one embodiment of the present invention is not limited to this structure, and a yellow light-emitting element or an orange light-emitting element may also be used. As the material for the EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, charge generation layer) used to manufacture these light-emitting elements, it can be appropriately used with reference to other embodiments. In this case, it is necessary to appropriately select a color filter according to the light-emitting color of the light-emitting element.

[0148] By adopting the above structure, a light-emitting device including a light-emitting element that emits light of multiple colors can be obtained.

[0149] The structure described in this embodiment mode can be used in combination with the structures described in other embodiment modes as appropriate.

[0150] (Implementation 4) In this embodiment, a light-emitting device which is one embodiment of the present invention is described.

[0151] By adopting the element structure of the light-emitting element of one embodiment of the present invention, an active matrix light-emitting device or a passive matrix light-emitting device can be manufactured. In addition, the active matrix light-emitting device has a structure in which a light-emitting element and a transistor (FET) are combined. Thus, both the passive matrix light-emitting device and the active matrix light-emitting device are included in one embodiment of the present invention. In addition, the light-emitting element described in other embodiments can be applied to the light-emitting device described in this embodiment.

[0152] In this embodiment, first refer to Figure 3A and Figure 3B An active matrix light-emitting device is described.

[0153] Figure 3A is a top view of the light emitting device, Figure 3B is along Figure 3A The active matrix light emitting device includes a pixel portion 302, a driving circuit portion (source line driving circuit) 303, and a driving circuit portion (gate line driving circuit) (304a, 304b) provided on a first substrate 301. The pixel portion 302 and the driving circuit portion (303, 304a, 304b) are sealed between the first substrate 301 and the second substrate 306 with a sealant 305.

[0154] A routing wiring 307 is provided on the first substrate 301. The routing wiring 307 is connected to an FPC 308 as an external input terminal. The FPC 308 is used to transmit external signals (for example, video signals, clock signals, start signals, or reset signals, etc.) or potentials to the drive circuit portion (303, 304a, 304b). In addition, the FPC 308 may also be mounted with a printed wiring board (PWB). The state in which these FPCs and PWBs are mounted may also be included in the light emitting device.

[0155] Figure 3B A cross-sectional structure is shown.

[0156] The pixel portion 302 includes a plurality of pixels including a FET (switching FET) 311, a FET (current control FET) 312, and a first electrode 313 electrically connected to the FET 312. The number of FETs in each pixel is not particularly limited, and may be appropriately set as required.

[0157] In addition, there is no particular limitation on the FETs 309, 310, 311, and 312, and for example, staggered transistors or inversely staggered transistors may be used. In addition, a top-gate transistor structure or a bottom-gate transistor structure may also be used.

[0158] In addition, there is no particular restriction on the crystallinity of the semiconductor that can be used for the above-mentioned FETs 309, 310, 311, and 312, and any one of an amorphous semiconductor and a crystalline semiconductor (a microcrystalline semiconductor, a polycrystalline semiconductor, a single crystal semiconductor, or a semiconductor having a crystalline region in part thereof) can also be used. By using a crystalline semiconductor, the degradation of transistor characteristics can be suppressed, so it is preferred.

[0159] As the semiconductor, for example, Group 14 elements, compound semiconductors, oxide semiconductors, organic semiconductors, etc. Typically, a semiconductor containing silicon, a semiconductor containing gallium arsenide, an oxide semiconductor containing indium, etc. can be used.

[0160] The driving circuit section 303 includes FET 309 and FET 310. FET 309 and FET 310 may be formed by a circuit including unipolar (either N-type or P-type) transistors, or may be formed by a CMOS circuit including N-type transistors and P-type transistors. Alternatively, a structure having an external driving circuit may be adopted.

[0161] The end of the first electrode 313 is covered by an insulator 314. The insulator 314 can be made of an organic compound such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin) or an inorganic compound such as silicon oxide, silicon oxynitride, or silicon nitride. The upper end or the lower end of the insulator 314 preferably has a curved surface with curvature. Thus, the film formed on the insulator 314 can have good coverage.

[0162] An EL layer 315 and a second electrode 316 are stacked over the first electrode 313. The EL layer 315 includes a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like.

[0163] As the structure of the light-emitting element 317 described in this embodiment, the structure or material described in other embodiments can be applied. Although not shown here, the second electrode 316 is electrically connected to the FPC 308 which is an external input terminal.

[0164] Although in Figure 3BOnly one light-emitting element 317 is shown in the cross-sectional view shown, but a plurality of light-emitting elements are arranged in a matrix in the pixel portion 302. By selectively forming light-emitting elements capable of obtaining light of three colors (R, G, B) in the pixel portion 302, a light-emitting device capable of full-color display can be formed. In addition, in addition to light-emitting elements capable of obtaining light of three colors (R, G, B), light-emitting elements capable of obtaining light of colors such as white (W), yellow (Y), magenta (M), and cyan (C) can also be formed. For example, by adding light-emitting elements capable of obtaining the above-mentioned multiple light-emitting elements to light-emitting elements capable of obtaining light of three colors (R, G, B), effects such as improving color purity and reducing power consumption can be obtained. In addition, a light-emitting device capable of full-color display can also be realized by combining with a color filter. Note that red (R), green (G), blue (B), cyan (C), magenta (M), yellow (Y), etc. can be used as color filters.

[0165] The second substrate 306 is bonded to the first substrate 301 by using the sealant 305, so that the FETs (309, 310, 311, 312) and the light-emitting element 317 on the first substrate 301 are located in a space 318 surrounded by the first substrate 301, the second substrate 306, and the sealant 305. In addition, the space 318 can be filled with an inert gas (such as nitrogen or argon), or can be filled with an organic substance (including the sealant 305).

[0166] An epoxy resin or glass frit can be used as the sealant 305. In addition, as the sealant 305, it is preferable to use a material that does not allow moisture and oxygen to pass through as much as possible. In addition, the second substrate 306 can use the same material as the first substrate 301. Thus, various substrates shown in other embodiments can be used. As a substrate, in addition to a glass substrate and a quartz substrate, a plastic substrate composed of FRP (Fiber-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic resin, etc. can also be used. From the viewpoint of adhesion, when glass frit is used as the sealant, it is preferable to use a glass substrate as the first substrate 301 and the second substrate 306.

[0167] As described above, an active matrix light-emitting device can be obtained.

[0168] In addition, when an active matrix light-emitting device is formed on a flexible substrate, FET and light-emitting elements can be directly formed on the flexible substrate, or FET and light-emitting elements can be formed on another substrate having a peeling layer, and then the FET and light-emitting elements can be peeled off from the peeling layer by applying heat, force, laser irradiation, etc., and then transferred to the flexible substrate. In addition, as a peeling layer, for example, a laminate of inorganic films such as tungsten film and silicon oxide film or an organic resin film such as polyimide can be used. In addition, as a flexible substrate, in addition to a substrate on which a transistor can be formed, paper substrates, glass paper substrates, aramid film substrates, polyimide film substrates, cloth substrates (including natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester) or regenerated fibers (acetate, cuprammonium fiber, rayon, regenerated polyester)), leather substrates, rubber substrates, etc. can also be cited. By using such a substrate, good durability and heat resistance as well as light weight and thinness can be achieved.

[0169] The structure described in this embodiment mode can be used in combination with the structures described in other embodiment modes as appropriate.

[0170] (Implementation method 5) In this embodiment, examples of various electronic devices or automobiles to which a light-emitting device of one embodiment of the present invention or a display device manufactured including a light-emitting element of one embodiment of the present invention is applied are described.

[0171] FIG. 4A to FIG. 4E The electronic device shown may include a frame 7000, a display portion 7001, a speaker 7003, an LED lamp 7004, an operation key 7005 (including a power switch or an operation switch), a connecting terminal 7006, a sensor 7007 (having the function of measuring the following factors: force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electricity, radiation, flow, humidity, inclination, vibration, smell or infrared), microphones 7008, 7019, etc.

[0172] Figure 4A A mobile computer is shown, which may include a switch 7009, an infrared port 7010, etc. in addition to the above.

[0173] Figure 4B A portable image reproduction device (for example, a DVD reproduction device) having a recording medium is shown. In addition to the above, the portable image reproduction device may include a second display portion 7002, a recording medium reading portion 7011, and the like.

[0174] Figure 4CA goggle-type display is shown, which may include a second display portion 7002, a support portion 7012, headphones 7013, and the like in addition to the above.

[0175] Figure 4D A digital camera having a television reception function is shown, and the digital camera may include an antenna 7014, a shutter button 7015, an image receiving unit 7016, and the like in addition to the above.

[0176] Figure 4E A mobile phone (including a smartphone) is shown, and a housing 7000 may include a display portion 7001 , a microphone 7019 , a speaker 7003 , a camera 7020 , an external connection portion 7021 , an operation button 7022 , and the like.

[0177] Figure 4F A large television device (also referred to as a television or a television receiver) is shown, and may include a housing 7000, a display portion 7001, speakers 7003, etc. In addition, a structure in which the housing 7000 is supported by a stand 7018 is shown.

[0178] 4A to 4F The electronic device shown may have various functions. For example, it may have the following functions: displaying various information (static images, dynamic images, text images, etc.) on the display unit; touch panel; displaying calendar, date or time, etc.; controlling processing by using various software (programs); performing wireless communications; connecting to various computer networks by using the wireless communication function; sending or receiving various data by using the wireless communication function; reading out programs or data stored in a recording medium to display them on the display unit, etc. Furthermore, in an electronic device having multiple display units, it may have the following functions: one display unit mainly displays image information, while another display unit mainly displays text information; or, images that take parallax into account are displayed on multiple display units to display stereoscopic images, etc. Furthermore, in an electronic device having an image receiving unit, it may have the following functions: shooting static images; shooting dynamic images; automatically or manually correcting the shot images; storing the shot images in a recording medium (external or built-in to the camera); displaying the shot images on the display unit, etc. Note that, 4A to 4F The functions that the electronic device shown may have are not limited to the above functions, but may have various functions.

[0179] Figure 4G 7000 , a display portion 7001 , an operation button 7022 , an operation button 7023 , a connection terminal 7024 , a strap 7025 , a strap buckle 7026 , and the like are shown.

[0180] The display panel 7001 installed in the frame 7000 which also serves as a frame (bezel) has a non-rectangular display area. The display unit 7001 can display an icon 7027 indicating the time and other icons 7028. In addition, the display unit 7001 can also be a touch screen (input-output device) equipped with a touch sensor (input device).

[0181] Figure 4G The smartwatch shown may have various functions. For example, it may have the following functions: display various information (static images, dynamic images, text images, etc.) on the display unit; touch panel; display calendar, date or time, etc.; control processing by using various software (programs); perform wireless communication; connect to various computer networks by using wireless communication functions; send or receive various data by using wireless communication functions; read programs or data stored in a recording medium and display them on the display unit, etc.

[0182] The interior of the frame 7000 may have a speaker, a sensor (with the function of measuring the following factors: force, displacement, position, speed, acceleration, angular velocity, rotation speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electricity, radiation, flow, humidity, inclination, vibration, odor or infrared), a microphone, etc.

[0183] Note that a light-emitting device according to one embodiment of the present invention and a display device including a light-emitting element according to one embodiment of the present invention can be used for each display portion of the electronic device described in this embodiment, and can achieve display with high color purity.

[0184] Electronic devices to which the light emitting device is applied include: FIG. 5A to FIG. 5C The portable information terminal shown is foldable. Figure 5A The portable information terminal 9310 is shown in the unfolded state. Figure 5B The portable information terminal 9310 is shown in a state in the process of changing from one of the unfolded state and the folded state to the other state. Figure 5C The portable information terminal 9310 is shown in a folded state. The portable information terminal 9310 is highly portable in the folded state, and has a large display area that is seamlessly connected and provides a high level of visibility in the unfolded state.

[0185] The display unit 9311 is supported by three frames 9315 connected by a hinge unit 9313. In addition, the display unit 9311 may also be a touch screen (input-output device) equipped with a touch sensor (input device). In addition, the display unit 9311 is bent at the connection portion of the two frames 9315 using the hinge unit 9313, thereby enabling the portable information terminal 9310 to be reversibly changed from an unfolded state to a folded state. A light-emitting device of one embodiment of the present invention may be applied to the display unit 9311. In addition, a display with good color purity can be achieved. The display area 9312 in the display unit 9311 is a display area located on the side of the portable information terminal 9310 in the folded state. Information icons or shortcuts to frequently used application software or programs can be displayed in the display area 9312, so that information confirmation or application software opening can be smoothly performed.

[0186] Fig. 6A and Figure 6B A car to which the light emitting device is applicable is shown. That is, the light emitting device can be formed integrally with the car. Specifically, it can be applied to Fig. 6A The exterior lights 5101 of the car shown (including the rear part of the car body), the wheel hub 5102 of the tire, a part or the whole of the door 5103, etc. Figure 6B The display unit 5104, steering wheel 5105, gear lever 5106, seat 5107, rearview mirror 5108, etc. inside the car are shown. In addition, it can also be applied to a part of the glass window.

[0187] As described above, an electronic device or automobile to which a light-emitting device or display device of one embodiment of the present invention is applicable can be obtained. In addition, in this case, a display with good color purity can be achieved. An electronic device or automobile to which a light-emitting device or display device of one embodiment of the present invention is applicable is not limited to the electronic device or automobile shown in this embodiment, but can be applied in various fields.

[0188] Note that the structure described in this embodiment can be used in combination with the structure described in other embodiment modes as appropriate. (Implementation method 6)

[0189] In this embodiment, refer to FIG. 7A to FIG. 7D The structure of a lighting device manufactured by applying the light-emitting device of one embodiment of the present invention or a light-emitting element which is a part thereof will be described.

[0190] FIG. 7A to FIG. 7D An example of a cross-sectional view of a lighting device is shown. Fig. 7A and Figure 7B It is a bottom-emitting lighting device that extracts light on the substrate side, Figure 7C and Fig.7D It is a top emission type lighting device that extracts light on the sealing substrate side.

[0191] Fig. 7A The lighting device 4000 shown includes a light-emitting element 4002 over a substrate 4001. In addition, the lighting device 4000 includes a substrate 4003 having projections and depressions on the outer side of the substrate 4001. The light-emitting element 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.

[0192] The first electrode 4004 is electrically connected to the electrode 4007, and the second electrode 4006 is electrically connected to the electrode 4008. In addition, an auxiliary wiring 4009 electrically connected to the first electrode 4004 may be provided. In addition, an insulating layer 4010 is formed over the auxiliary wiring 4009.

[0193] The substrate 4001 and the sealing substrate 4011 are bonded together with a sealant 4012. In addition, a desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting element 4002. Fig. 7A The unevenness as shown can improve the efficiency of extracting light generated in the light-emitting element 4002.

[0194] In addition, if Figure 7B As in the lighting device 4100 shown in the figure, a diffusion plate 4015 may be provided on the outer side of the substrate 4001 instead of the substrate 4003 .

[0195] Figure 7C The illustrated lighting device 4200 includes a light-emitting element 4202 over a substrate 4201. The light-emitting element 4202 includes a first electrode 4204, an EL layer 4205, and a second electrode 4206.

[0196] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. In addition, an auxiliary wiring 4209 electrically connected to the second electrode 4206 may be provided. In addition, an insulating layer 4210 may be provided under the auxiliary wiring 4209.

[0197] The substrate 4201 and the sealing substrate 4211 having projections and depressions are bonded together by a sealant 4212. A barrier film 4213 and a planarizing film 4214 may be provided between the sealing substrate 4211 and the light emitting element 4202. Figure 7C The unevenness as shown in the figure can improve the efficiency of extracting light generated in the light-emitting element 4202.

[0198] In addition, if Fig.7D As in the lighting device 4300 shown in the figure, a diffusion plate 4215 may be provided over the light emitting element 4202 instead of the sealing substrate 4211 .

[0199] In addition, as described in this embodiment, by applying a light-emitting device of one embodiment of the present invention or a light-emitting element which is a part thereof, a lighting device having desired chromaticity can be provided.

[0200] The structure described in this embodiment can be combined with the structure described in other embodiment modes as appropriate.

[0201] (Implementation 7) In this embodiment, refer to Figure 8 An application example of a lighting device manufactured by applying the light-emitting device of one embodiment of the present invention or a light-emitting element which is a part thereof will be described.

[0202] As an indoor lighting device, a ceiling spotlight 8001 can be used. As a ceiling spotlight 8001, there are direct installation types and embedded types. This lighting device is manufactured by combining a light-emitting device with a frame or a cover. In addition, it can also be applied to a lighting device of a chandelier (suspended from the ceiling with wires).

[0203] In addition, the foot lamp 8002 illuminates the ground, which can improve the safety of the foot. For example, it is very effective to use it in a bedroom, staircase or passage. In this case, the size or shape of the foot lamp can be appropriately changed according to the size or structure of the room. In addition, the foot lamp 8002 can also be a mounting type lighting device formed by combining a light emitting device and a bracket.

[0204] In addition, the sheet lighting 8003 is a thin film lighting device. Because it is attached to the wall and used, it does not take up space and can be applied to various purposes. In addition, it is easy to achieve a large area. In addition, it can also be attached to a wall or frame with a curved surface.

[0205] Alternatively, a lighting device 8004 may be used in which light from a light source is controlled so as to be emitted only in a desired direction.

[0206] By using the light-emitting device of one embodiment of the present invention or a light-emitting element which is a part thereof for a part of indoor furniture other than the above, a lighting device having the function of furniture can be provided.

[0207] As described above, various lighting devices to which the light emitting device is applied can be obtained. In addition, such lighting devices are included in one embodiment of the present invention.

[0208] The structure described in this embodiment mode can be implemented in combination with the structures described in other embodiment modes as appropriate. [Example 1]

[0209] 《Synthesis Example 1》 In this example, a method for synthesizing an organic compound 9'-phenyl-9'-[4-(10-phenyl-9-anthracenyl)phenyl]-2,3'-bi-9H-carbazole (abbreviated as PCCPA-02) which is one embodiment of the present invention and represented by the structural formula (200) of Embodiment 1 is described. Note that the structure of PCCPA-02 is shown below.

[0210] [Chemical formula 15]

[0211] 1.2 g (3.0 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.2 g (3.0 mmol) of 9'-phenyl-2,3'-bi-9H-carbazole, and 0.60 g (6.2 mmol) of sodium tert-butoxide were placed in a 200 mL three-necked flask, and the flask was purged with nitrogen. 30 mL of xylene was added to the mixture, and the mixture was stirred under reduced pressure for degassing. 0.4 mL of tri(tert-butyl)phosphine and 48 mg (83 μmol) of bis(dibenzylideneacetone)palladium(0) were added to the mixture, and the mixture was refluxed at 150°C for 6 hours under a nitrogen stream.

[0212] After stirring, water was added to the mixture and the aqueous layer was extracted with toluene. The obtained organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated saline solution, and the organic layer was dried with magnesium sulfate. The above mixture was gravity filtered and the filtrate was concentrated to obtain a solid. The toluene solution of the obtained oil was filtered through diatomaceous earth and alumina and the filtrate was concentrated to obtain a solid. The obtained solid was recrystallized with toluene, thereby obtaining 1.1 g of a light yellow solid of the target object with a yield of 49%. The following (a) shows the synthesis scheme of the above synthesis method.

[0213] [Chemical formula 16]

[0214] 1.1 g of the obtained light yellow solid was sublimated and purified by gradient sublimation. The sublimation purification conditions were as follows: 9'-phenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-2,3'-bi-9H-carbazole was heated at 335° C. at a pressure of 3.1 Pa and an argon gas flow rate of 5.0 mL / min. After sublimation purification, 1.0 g of a light yellow solid was obtained at a recovery rate of 92%.

[0215] The magnetic resonance spectroscopy of the obtained yellow solid is shown below ( 1 H-NMR) analysis results. Fig. 9A and Fig. 9B Show 1 H-NMR spectrum. Note that Fig. 9B Yes Fig. 9AThe spectrum is enlarged and shown in the range of 7.0 ppm to 9.0 ppm. From the results, it can be seen that the organic compound PCCPA-02 of one embodiment of the present invention represented by the above structural formula (200) was obtained in this example.

[0216] 1 H NMR (CDCl3, 300MHz): δ=7.29-7.81 (m, 27H), 7.85-7.94 (m, 5H), 8.24 (d, J=7.8Hz, 2H), 8.30 (d, J=7.8Hz, 1H), 8.48 (d, J=1.2Hz, 1H).

[0217] Next, the UV-visible absorption spectrum (hereinafter referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of PCCPA-02 were measured. A solid film was formed on a quartz substrate by vacuum evaporation. The absorption spectrum was measured using a UV-visible spectrophotometer (solution: V-550 manufactured by JASCO Corporation, film: U-4100 manufactured by Hitachi High-Technologies Corporation). Note that the absorption spectrum of the solution is calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz dish, and the absorbance (-log 10 The absorption spectrum of the film was calculated from [%T / (100-%R)]. Note that %T represents transmittance and %R represents reflectance. In addition, the emission spectrum was measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan).

[0218] Fig. 10A The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. In addition, Fig. 10B The measurement results of the absorption spectrum and emission spectrum of the solid film are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0219] according to Fig. 10A The results show that the toluene solution of PCCPA-02 has absorption peaks near 396nm, 376nm, 322nm, and 304nm, and has emission wavelength peaks at 422nm and 433nm (excitation wavelength 377nm). Fig. 10B The results showed that the solid film of PCCPA-02 had absorption peaks near 399nm, 377nm, 353nm, 325nm, and 304nm, and had a peak emission wavelength near 445nm (excitation wavelength 380nm).

[0220] In addition, it was confirmed that PCCPA-02 emits blue light. The organic compound PCCPA-02 of one embodiment of the present invention can be used as a luminescent material or a main body of a fluorescent luminescent material in the visible region. In addition, it is known that the film of PCCPA-02 has a good film quality that is not easy to condense in the atmosphere.

[0221] The HOMO level and LUMO level of PCCPA-02 were calculated by cyclic voltammetry (CV). The calculation method is shown below.

[0222] As a measuring device, an electrochemical analyzer (manufactured by BAS Inc., model: ALS model 600A or 600C) was used. In the solution for CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as a supporting electrolyte was dissolved at a concentration of 100 mmol / L, and the measurement object was dissolved at a concentration of 2 mmol / L to prepare.

[0223] A platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) was used as the working electrode, a platinum electrode (manufactured by BAS Co., Ltd., Pt counter electrode for VC-3 (5 cm)) was used as the auxiliary electrode, and an Ag / Ag electrode was used as the reference electrode. + Electrode (manufactured by BAS Corporation, RE7 non-aqueous reference electrode) The measurement was performed at room temperature (20° C. to 25° C.).

[0224] In addition, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] relative to the reference electrode were measured. Ea is the middle potential of the oxidation-reduction wave, and Ec is the middle potential of the reduction-oxidation wave. Here, since it is known that the potential energy of the reference electrode used in this embodiment relative to the vacuum energy level is -4.94 [eV], the HOMO energy level and the LUMO energy level can be calculated according to the formula of HOMO energy level [eV] -4.94-Ea, LUMO energy level [eV] -4.94-Ec.

[0225] Furthermore, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th measurement was compared with the oxidation-reduction wave in the first measurement to investigate the electrical stability of the compound.

[0225] The results show that the HOMO level of PCCPA-02 in the measurement of the oxidation potential Ea [V] is -5.69 eV. On the other hand, the LUMO level in the measurement of the reduction potential Ec [V] is -2.72 eV. In addition, in the repeated measurement of the oxidation-reduction wave, the waveforms after the first cycle and the 100th cycle were compared. Since 83% of the peak intensity was maintained in the Ea measurement and 87% of the peak intensity was maintained in the Ec measurement, it was confirmed that PCCPA-02 has excellent oxidation resistance and reduction resistance. [Example 2]

[0226] 《Synthesis Example 2》 In this example, a method for synthesizing an organic compound 9-phenyl-9'-[4-(10-phenyl-9-anthracenyl)phenyl]-2,2'-bi-9H-carbazole (abbreviated as PCCPA-03) which is one embodiment of the present invention and represented by the structural formula (221) of Embodiment 1 is described. Note that the structure of PCCPA-03 is shown below.

[0227] [Chemical formula 17]

[0228] 1.2 g (3.0 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.3 g (3.1 mmol) of 9-phenyl-2,2'-bi-9H-carbazole, and 0.59 g (6.1 mmol) of sodium tert-butoxide were placed in a 100 mL three-necked flask, and the interior of the flask was replaced with nitrogen. 30 mL of xylene was added to the mixture, and the mixture was stirred under reduced pressure for degassing. 0.4 mL of a 10 wt% hexane solution of tri(tert-butyl)phosphine and 85 mg (0.15 mmol) of bis(dibenzylideneacetone)palladium(0) were added to the mixture, and the mixture was refluxed at 140° C. for 6 hours under a nitrogen stream.

[0229] After stirring, the obtained mixture was washed with water, saturated sodium bicarbonate aqueous solution, and saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated. The obtained oil was purified by silica gel column chromatography (toluene: hexane 1: 2) and recrystallized with toluene to obtain 1.6 g of a light yellow solid of the target with a yield of 71%. The following (b) shows the synthesis scheme of the above-mentioned synthesis method.

[0230] [Chemical formula 18] 1.6 g of the obtained light yellow solid was sublimated and purified by gradient sublimation. In the sublimation purification, the mixture was heated at 320° C. for 18 hours under the conditions of a pressure of 3.2 Pa and an argon gas flow rate of 5.0 mL / min. After the sublimation purification, 1.4 g of a light yellow solid was obtained at a recovery rate of 93%.

[0232] The magnetic resonance spectroscopy of the obtained light yellow solid is shown below ( 1 H-NMR) analysis results. Fig.11A and Fig. 11B Show 1 H-NMR spectrum. Note that Fig. 11B Yes Fig.11A The spectrum is enlarged and shown in the range of 7.0 ppm to 8.5 ppm. From the results, it can be seen that the organic compound PCCPA-03 represented by the above structural formula (221) which is one embodiment of the present invention was obtained in this example.

[0233] 1 H NMR (1,1,2,2-tetrachloroethane-d2, 300 MHz): δ = 7.31-7.95 (m, 32H), 8.19 (d, J = 7.5 Hz, 1H), 8.23-8.28 (m, 3H). Next, the ultraviolet-visible absorption spectrum (hereinafter referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of PCCPA-03 were measured. A solid film was formed on a quartz substrate by vacuum evaporation. The absorption spectrum was measured using a spectrophotometer (solution: V-550 manufactured by JASCO Corporation, film: U-4100 manufactured by Hitachi High-Technologies Corporation). Note that the absorption spectrum of the solution is calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz dish, and the absorbance (-log 10 The absorption spectrum of the film was calculated from [%T / (100-%R)]. Note that %T represents transmittance and %R represents reflectance. In addition, the emission spectrum was measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan).

[0235] Fig. 12A The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. In addition, Fig. 12B The measurement results of the absorption spectrum and emission spectrum of the solid film are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0236] according to Fig. 12AThe results show that the toluene solution of PCCPA-03 has absorption peaks near 396nm, 375nm, and 326nm, and has a peak emission wavelength at 423nm (excitation wavelength 376nm). Fig. 12B The results showed that the solid film of PCCPA-03 had absorption peaks near 401 nm, 380 nm, 356 nm, and 335 nm, and had a peak emission wavelength near 446 nm (excitation wavelength 360 nm).

[0237] In addition, it was confirmed that PCCPA-03 emits blue light. The compound of one embodiment of the present invention can be used as a luminescent material or a main body of a fluorescent luminescent material in the visible region. In addition, it is known that the film of PCCPA-03 has a good film quality that is not easily condensed in the atmosphere. [Example 3]

[0238] In this embodiment, the element structure, manufacturing method and characteristics of light-emitting element 1 and comparative light-emitting element 2 are described. Light-emitting element 1 is a light-emitting element of one embodiment of the present invention, and PCCPA-02 (structural formula (200)) described in Example 1 is used in its light-emitting layer; comparative light-emitting element 2 used as a comparison uses a comparative organic compound PCCPA (structural formula (300)) in its light-emitting layer. Fig.13 The element structure of the light-emitting element used in this example is shown, and the specific structure is shown in Table 1. In addition, the chemical formulas of the materials used in this example are shown below.

[0239] [Table 1] *PCCPA-02:1,6mMemFLPAPrn(1:0.03 25nm) **PCCPA:1,6mMemFLPAPrn(1:0.03 25nm)

[0240] [Chemical formula 19]

[0241] 《Manufacturing of Light Emitting Components》 like Fig.13 As shown, the light-emitting element shown in this embodiment has the following structure: a hole injection layer 911, a hole transport layer 912, a light-emitting layer 913, an electron transport layer 914 and an electron injection layer 915 are stacked in sequence on a first electrode 901 formed on a substrate 900, and a second electrode 903 is stacked on the electron injection layer 915.

[0242] First, a first electrode 901 is formed on a substrate 900. The electrode area is 4 mm 2(2 mm×2 mm). In addition, a glass substrate is used as the substrate 900. First electrode 901 The indium tin oxide (ITSO) containing silicon oxide is formed to a thickness of 70 nm by a sputtering method.

[0243] Here, as a pretreatment, the substrate surface was cleaned with water, baked at 200°C for 1 hour, and then subjected to UV ozone treatment for 370 seconds. Then, the substrate was placed inside the chamber and the pressure was reduced to 10 -4 Pa in a vacuum evaporation device and in a heating chamber in the vacuum evaporation device, vacuum baking is performed at a temperature of 170° C. for 60 minutes, and then the substrate is cooled for about 30 minutes.

[0244] Next, a hole injection layer 911 is formed on the first electrode 901. The pressure in the vacuum evaporation device is reduced to 10 -4 After Pa, 3-[4-(9-phenanthrenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviated as: PCPPn) and molybdenum oxide are co-evaporated in a mass ratio of PCPPn:molybdenum oxide 4:2 and a thickness of 10 nm to form a hole injection layer 911.

[0245] Next, a hole transport layer 912 is formed on the hole injection layer 911. PCPPn is evaporated to a thickness of 30 nm to form the hole transport layer 912.

[0246] Next, a light-emitting layer 913 is formed on the hole transport layer 912.

[0247] In the light-emitting layer 913 of the light-emitting element 1, PCCPA-02 was used as a host material, and N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-pyrene-1,6-diamine (abbreviated as: 1,6mMemFLPAPrn) was used as a guest material, and co-evaporation was performed in a weight ratio of PCCPA-02:1,6mMemFLPAPrn 1:0.03. In addition, the film thickness was set to 25 nm.

[0248] The light-emitting layer 913 of the comparative light-emitting element 2 was formed by co-evaporation using PCCPA as a host material and 1,6 mMemFLPAPrn as a guest material at a weight ratio of PCCPA:1,6 mMemFLPAPrn=1:0.03. The film thickness was set to 25 nm.

[0249] Next, an electron transport layer 914 is formed on the light-emitting layer 913. In the light-emitting element 1, the electron transport layer 914 is formed by sequentially evaporating PCCPA-02 and bathophenanthroline (abbreviated as Bphen) to a thickness of 10 nm and 15 nm, respectively. In addition, in the comparative light-emitting element 2, the electron transport layer 914 is formed by sequentially evaporating PCCPA and bathophenanthroline to a thickness of 10 nm and 15 nm, respectively.

[0250] Next, the electron injection layer 915 is formed on the electron transport layer 914. The electron injection layer 915 is formed by evaporating lithium fluoride (LiF) to a thickness of 1 nm.

[0251] Next, the second electrode 903 is formed on the electron injection layer 915. The second electrode 903 is formed by evaporating aluminum to a thickness of 200 nm. In this embodiment, the second electrode 903 is used as a cathode.

[0252] 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, the electron transport layer 914, and the electron injection layer 915 described in the above steps are functional layers constituting the EL layer in one embodiment of the present invention. In addition, in the vapor deposition process of the above manufacturing method, the vapor deposition is performed by the resistance heating method.

[0253] In addition, another substrate (not shown) is used to seal the light-emitting element produced as described above. When another substrate (not shown) is used for sealing, another substrate (not shown) is fixed to the substrate 900 using a sealant in a glove box with a nitrogen atmosphere, and the sealant is applied around the light-emitting element formed on the substrate 900. During sealing, the sealant is heated at 6 J / cm 2 The film was irradiated with ultraviolet light of 365 nm and heated at 80° C. for 1 hour.

[0254] 《Operating characteristics of light-emitting elements》 The operating characteristics of each light-emitting element manufactured were measured. The measurements were performed at room temperature. Figures 14 to 17 The results are shown.

[0255] In addition, Table 2 below shows that 1000 cd / m 2 The main initial characteristic values ​​of each nearby light-emitting element.

[0256] [Table 2]

[0257] From the above results, it can be seen that the light-emitting element 1 manufactured in this embodiment has excellent current efficiency and high external quantum efficiency. From the results, it can be seen that by changing the bonding position of the first carbazole skeleton bonded to the anthracene skeleton and the second carbazole skeleton bonded to the first carbazole skeleton, the energy transfer of the light-emitting material is smoothly performed, and good element characteristics can be obtained.

[0258] in addition, Fig.18 Shown at 12.5 mA / cm 2 The emission spectra when the current density is made to flow through the light-emitting element 1 and the light-emitting element 2 are compared. Fig.18 It can be seen that the emission spectra of the light-emitting element 1 and the comparative light-emitting element 2 have a peak near 466 nm, and the peak is derived from the light emission of 1.6 mMemFLPAPrn contained in the light-emitting layer 913.

[0259] Next, reliability tests of the light emitting element 1 and the comparative light emitting element 2 were performed. Fig.19 The results of the reliability test are shown in Fig.19 In the figure, the vertical axis represents the normalized brightness (%) when the initial brightness is 100%, and the horizontal axis represents the driving time (h) of the element. As a reliability test, a constant current driving test was performed at 2 mA.

[0260] The results show that the light-emitting element (light-emitting element 1) of one embodiment of the present invention exhibits better characteristics than the comparison light-emitting element 2 in terms of current efficiency and external quantum efficiency, and is also superior in reliability. [Example 4]

[0261] 《Synthesis Example 3》 In this example, a method for synthesizing an organic compound 7-[4-(10-phenyl-9-anthracenyl)phenyl]-9-(9-phenyl-9H-carbazole-3-yl)-7H-benzo[c]carbazole (abbreviated as PCcBCzPA) which is one embodiment of the present invention represented by the structural formula (252) of Embodiment 1 is described. Note that the structure of PCcBCzPA is shown below.

[0262] [Chemical formula 20]

[0263] 1.8 g (4.4 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 2.0 g (4.4 mmol) of 9-(9-phenyl-9H-carbazole-3-yl)-7H-benzo[c]carbazole, and 0.85 g (8.8 mmol) of sodium tert-butoxide were placed in a 100 mL three-necked flask, and the flask was purged with nitrogen. 22 mL of xylene and 0.9 mL of a 10 wt% hexane solution of tri(tert-butyl)phosphine were added to the mixture, and the mixture was stirred under reduced pressure for degassing. 0.13 g (0.22 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was refluxed at 160°C for 6 hours under a nitrogen stream.

[0264] After stirring, water was added to the mixture and the solid was filtered. The toluene solution of the obtained solid was filtered through diatomaceous earth, alumina and magnesium silicate, and the filtrate was concentrated to obtain a solid. The obtained solid was purified by silica gel column chromatography (toluene) and recrystallized using toluene, thereby obtaining 2.2 g of a light yellow solid of the target product with a yield of 63%. The following formula (c) shows the synthesis scheme of the above synthesis method.

[0265] [Chemical formula 21]

[0266] The obtained 0.95 g of light yellow solid was purified by sublimation using gradient sublimation. -2 Pa, the light yellow solid was heated at 300° C. After sublimation purification, 0.74 g of a light yellow solid was obtained at a recovery rate of 78%.

[0267] The nuclear magnetic resonance spectroscopy of the obtained light yellow solid is shown below ( 1 H-NMR) analysis results. Fig. 20A and Fig. 20B Show 1 H-NMR spectrum. Note that Fig. 20B Yes Fig. 20A The spectrum is enlarged and shown in the range of 7.0 ppm to 9.0 ppm. From the results, it can be seen that the organic compound PCcBCzPA of one embodiment of the present invention represented by the above structural formula (252) was obtained in this example.

[0268] 1H NMR (CDCl3, 300MHz): δ=7.29-7.97 (m, 32H), 8.03 (d, J=1.5Hz, 1H), 8.08 (d, J=7.8Hz, 1H), 8.25 (d, J=7.8Hz, 1H), 8.51 (d, J=1.5Hz, 1H), 8.79 (d, J=8.4Hz, 1H), 8.95 (d, J=8.1Hz, 1H).

[0269] Next, the UV-visible absorption spectrum (hereinafter referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of PCcBCzPA were measured. A solid film was formed on a quartz substrate by vacuum evaporation. The absorption spectrum was measured using a UV-visible spectrophotometer (solution: V-550 manufactured by JASCO Corporation, film: U-4100 manufactured by Hitachi High-Technologies Corporation). Note that the absorption spectrum of the solution is calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz dish, and the absorbance (-log 10 The absorption spectrum of the film was calculated from [%T / (100-%R)]. Note that %T represents transmittance and %R represents reflectance. In addition, the emission spectrum was measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan).

[0270] Fig.21A The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. In addition, Fig. 21B The measurement results of the absorption spectrum and emission spectrum of the solid film are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0271] according to Fig.21A The results showed that the toluene solution of PCcBCzPA had absorption peaks near 396nm, 375nm, 355nm, and 341nm, and had emission wavelength peaks at 422nm and 434nm (excitation wavelength 375nm). Fig. 21B As a result, the solid film of PCcBCzPA has absorption peaks near 402nm, 380nm, 359nm, 345nm, and 305nm, and has a peak emission wavelength near 446nm (excitation wavelength 370nm).

[0272] In addition, it was confirmed that PCcBCzPA emits blue light. The organic compound PCcBCzPA of one embodiment of the present invention can be used as a luminescent material or a main body of a fluorescent luminescent material in the visible region. In addition, it is known that the thin film of PCcBCzPA has a good film quality that is not easy to condense in the atmosphere and has little morphological change.

[0273] The HOMO level and LUMO level of PCcBCzPA were calculated by CV measurement. The calculation method is shown below.

[0274] As a measuring device, an electrochemical analyzer (manufactured by BAS Inc., model: ALS model 600A or 600C) was used. In the solution for CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as a supporting electrolyte was dissolved at a concentration of 100 mmol / L, and the measurement object was dissolved at a concentration of 2 mmol / L to prepare.

[0275] A platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) was used as the working electrode, a platinum electrode (manufactured by BAS Co., Ltd., Pt counter electrode for VC-3 (5 cm)) was used as the auxiliary electrode, and an Ag / Ag electrode was used as the reference electrode. + Electrode (manufactured by BAS Corporation, RE7 non-aqueous reference electrode) The measurement was performed at room temperature (20° C. to 25° C.).

[0276] In addition, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] relative to the reference electrode were measured. Ea is the middle potential of the oxidation-reduction wave, and Ec is the middle potential of the reduction-oxidation wave. Here, since it is known that the potential energy of the reference electrode used in this embodiment relative to the vacuum energy level is -4.94 [eV], the HOMO energy level and the LUMO energy level can be calculated according to the formula of HOMO energy level [eV] -4.94-Ea, LUMO energy level [eV] -4.94-Ec.

[0277] Furthermore, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th measurement was compared with the oxidation-reduction wave in the first measurement to investigate the electrical stability of the compound. The results show that the HOMO level of PCcBCzPA was -5.64 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of PCcBCzPA was -2.73 eV in the measurement of the reduction potential Ec [V]. In addition, in the repeated measurement of the oxidation-reduction wave, the waveforms after the first cycle and the 100th cycle were compared. Since 85% of the peak intensity was maintained in the Ea measurement and 71% of the peak intensity was maintained in the Ec measurement, it was confirmed that PCcBCzPA had excellent oxidation resistance and reduction resistance. [Example 5]

[0278] 《Synthesis Example 4》 In this example, a method for synthesizing an organic compound 7-[4-(10-phenyl-9-anthracenyl)phenyl]-9-(9-phenyl-9H-carbazole-2-yl)-7H-benzo[c]carbazole (abbreviated as PCcBCzPA-02) which is one embodiment of the present invention and represented by the structural formula (253) of Embodiment 1 is described. Note that the structure of PCcBCzPA-02 is shown below.

[0279] [Chemical formula 22]

[0280] 0.80 g (2.0 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.90 g (2.0 mmol) of 9-(9-phenyl-9H-carbazole-2-yl)-7H-benzo[c]carbazole, and 0.38 g (4.0 mmol) of sodium tert-butoxide were placed in a 100 mL three-necked flask, and the interior of the flask was replaced with nitrogen. 10 mL of xylene and 0.4 mL of a 10 wt% hexane solution of tri(tert-butyl)phosphine were added to the mixture, and deaerated under reduced pressure. 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the mixture was refluxed at 150° C. for 6 hours under a nitrogen stream.

[0281] After stirring, the mixture was filtered and the solid was washed with water. The filtrate was washed with saturated brine and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated. The obtained oil and solid were purified by silica gel column chromatography (toluene: hexane = 1: 2) and recrystallized using toluene / hexane to obtain 0.70 g of a white solid of the target with a yield of 59%. The following (d) shows the synthesis scheme of the above-mentioned synthesis method.

[0282] [Chemical formula 23]

[0283] The obtained white solid (0.50 g) was purified by sublimation using a gradient sublimation method. The sublimation purification conditions were: a pressure of 3.2×10 -2 Pa, and heated at 300° C. After sublimation purification, 0.40 g of a yellow solid was obtained at a recovery rate of 80%.

[0284] The magnetic resonance spectroscopy of the obtained yellow solid is shown below ( 1 H-NMR) analysis results. Fig.22A and Fig. 22B Show 1 H-NMR spectrum. Note that Fig. 22B Yes Fig.22A The spectrum is enlarged and shown in the range of 7.0 ppm to 9.0 ppm. From the results, it can be seen that the organic compound PCcBCzPA-02 represented by the above structural formula (253) which is one embodiment of the present invention was obtained in this example.

[0285] 1 H NMR (CDCl3, 300MHz): δ=7.28-7.91 (m, 31H), 7.95 (d, J=9.3Hz, 1H), 7.99 (d, J=1.5Hz, 1H), 8.08 (d, J=7 .8Hz, 1H), 8.18 (d, J=7.5Hz, 1H), 8.26 (d, J=7.8Hz, 1H), 8.73 (d, J=8.1Hz, 1H), 8.91 (d, J=8.7Hz, 1H).

[0286] Next, the ultraviolet-visible absorption spectrum (hereinafter referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of PCcBCzPA-02 were measured. A solid film was formed on a quartz substrate by vacuum evaporation. The absorption spectrum was measured using a spectrophotometer (solution: V-550 manufactured by JASCO Corporation, film: U-4100 manufactured by Hitachi High-Technologies Corporation). Note that the absorption spectrum of the solution is calculated by subtracting the absorption spectrum measured by placing only toluene in a quartz dish, and the absorbance (-log 10 The absorption spectrum of the film was calculated from [%T / (100-%R)]. Note that %T represents transmittance and %R represents reflectance. In addition, the emission spectrum was measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan).

[0287] Fig.23A The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. In addition, Fig. 23B The measurement results of the absorption spectrum and emission spectrum of the solid film are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0288] according to Fig.23A The results show that the toluene solution of PCcBCzPA-02 has absorption peaks near 396nm, 376nm, 355nm, 343nm, and 320nm, and has a peak emission wavelength at 422nm (excitation wavelength 376nm). Fig. 23B The results showed that the solid film of PCcBCzPA-02 had absorption peaks near 401nm, 381nm, 358nm, 343nm, and 323nm, and had a peak emission wavelength near 445nm (excitation wavelength 370nm).

[0289] In addition, it was confirmed that PCcBCzPA-02 emits blue light. The compound of one embodiment of the present invention can be used as a luminescent material or a main body of a fluorescent material in the visible region. In addition, the thin film of PCcBCzPA-02 has a good film quality that is not easily condensed even in the atmosphere.

[0290] The HOMO level and LUMO level of PCcBCzPA-02 were calculated by CV measurement. The calculation method is shown below.

[0291] As a measuring device, an electrochemical analyzer (manufactured by BAS Inc., model: ALS model 600A or 600C) was used. In the solution for CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich Co., Ltd., 99.8%, catalog number: 22705-6) was used as a solvent, tetra-n-butylammonium perchlorate (n-Bu4NClO4) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) as a supporting electrolyte was dissolved at a concentration of 100 mmol / L, and the measurement object was dissolved at a concentration of 2 mmol / L to prepare.

[0292] A platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode) was used as the working electrode, a platinum electrode (manufactured by BAS Co., Ltd., Pt counter electrode for VC-3 (5 cm)) was used as the auxiliary electrode, and an Ag / Ag electrode was used as the reference electrode. + Electrode (manufactured by BAS Corporation, RE7 non-aqueous reference electrode) The measurement was performed at room temperature (20° C. to 25° C.).

[0293] In addition, the scanning speed during CV measurement was unified to 0.1 V / sec, and the oxidation potential Ea [V] and the reduction potential Ec [V] relative to the reference electrode were measured. Ea is the middle potential of the oxidation-reduction wave, and Ec is the middle potential of the reduction-oxidation wave. Here, since it is known that the potential energy of the reference electrode used in this embodiment relative to the vacuum energy level is -4.94 [eV], the HOMO energy level and the LUMO energy level can be calculated according to the formula of HOMO energy level [eV] -4.94-Ea, LUMO energy level [eV] -4.94-Ec.

[0294] Furthermore, CV measurement was repeated 100 times, and the oxidation-reduction wave in the 100th measurement was compared with the oxidation-reduction wave in the first measurement to investigate the electrical stability of the compound.

[0296] The results show that the HOMO level of PCcBCzPA-02 was -5.73 eV in the measurement of the oxidation potential Ea [V]. On the other hand, the LUMO level of PCcBCzPA-02 was -2.74 eV in the measurement of the reduction potential Ec [V]. In addition, in the repeated measurement of the oxidation-reduction wave, the waveforms after the first cycle and the 100th cycle were compared, and since 78% of the peak intensity was maintained in the Ea measurement, it was confirmed that PCcBCzPA-02 had excellent oxidation resistance. [Example 6]

[0295] 《Synthesis Example 5》 In this example, a method for synthesizing an organic compound 9-[4-(10-phenyl-9-anthracenyl)phenyl]-2,9'-bi-9H-carbazole (abbreviated as CzCzPA-02) which is one embodiment of the present invention and represented by the structural formula (220) of Embodiment 1 is described. Note that the structure of CzCzPA-02 is shown below.

[0296] [Chemical formula 24]

[0297] 0.65 g (1.6 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.54 g (1.6 mmol) of 2,9'-bi-9H-carbazole, and 0.32 g (3.3 mmol) of sodium tert-butoxide were placed in a 100 mL three-necked flask, and the flask was purged with nitrogen. 10 mL of xylene was added to the mixture, and the mixture was stirred under reduced pressure to degas. 0.4 mL of a 10 w% hexane solution of tri(tert-butyl)phosphine and 34 mg (59 μmol) of bis(dibenzylideneacetone)palladium(0) were added to the mixture, and the mixture was stirred at 120°C for 6 hours under a nitrogen stream.

[0298] After stirring, the obtained mixture was washed with water and saturated brine, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered and the filtrate was concentrated. The obtained oil was purified by silica gel column chromatography (toluene: hexane = 1: 2) and high performance liquid chromatography (developing solvent: chloroform), and recrystallized with toluene to obtain 0.66 g of the target white solid with a yield of 63%. The following (e) shows the synthesis scheme of the above synthesis method.

[0299] [Chemical formula 25] The obtained white solid (0.69 g) was purified by sublimation using a gradient sublimation method. During the sublimation purification, the mixture was heated at 300°C for 22 hours under the conditions of a pressure of 3.4 Pa and an argon gas flow rate of 5.0 mL / min. After the sublimation purification, 0.61 g of a light yellow solid was obtained at a recovery rate of 88%.

[0301] The magnetic resonance spectroscopy of the obtained light yellow solid is shown below ( 1 H-NMR) analysis results. Fig.24A and Fig. 24B Show 1 H-NMR spectrum. Note that Fig. 24B Yes Fig.24A The spectrum is enlarged and shown in the range of 7.0 ppm to 9.0 ppm. From the results, it can be seen that the organic compound CzCzPA-02 of one embodiment of the present invention represented by the above structural formula (220) was obtained in this example.

[0302] 1 H NMR (DMSO-d6, 300MHz): δ=7.31 (dt, J=0.9Hz, 7.8Hz, 2H), 7.40-7.76 (m, 23H), 7.82 (d, J=1.5Hz, 1H), 8.02 (d, J=8.4Hz, 2H), 8.28 (d, J=7.8Hz, 2H), 8.45 (d, J=7.5Hz, 1H), 8.61 (d, J=8.1Hz, 1H).

[0303] Next, the ultraviolet-visible absorption spectrum (hereinafter referred to as "absorption spectrum") and emission spectrum of the toluene solution and solid film of CzCzPA-02 were measured. A solid film was formed on a quartz substrate by vacuum evaporation. The absorption spectrum was measured using a spectrophotometer (solution: V-550 manufactured by JASCO Corporation, film: U-4100 manufactured by Hitachi High-Technologies Corporation). Note that the absorption spectrum of the solution is calculated by subtracting the absorption spectrum measured by placing only toluene in the quartz dish, and the absorbance (-log 10 The absorption spectrum of the film was calculated from [%T / (100-%R)]. Note that %T represents transmittance and %R represents reflectance. In addition, the emission spectrum was measured using a fluorescence photometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd., Japan).

[0304] Fig.25A The measurement results of the absorption spectrum and emission spectrum of the obtained toluene solution are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and the emission intensity. In addition, Fig.25B The measurement results of the absorption spectrum and emission spectrum of the solid film are shown. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0305] according to Fig.25A The results show that the toluene solution of CzCzPA-02 has absorption peaks near 396nm, 376nm, 356nm, 334nm, and 322nm, and has emission wavelength peaks at 419nm and 434nm (excitation wavelength 376nm). Fig.25B As a result, the solid film of CzCzPA-02 has absorption peaks near 402nm, 380nm, and 335nm, and has a peak of emission wavelength near 440nm (excitation wavelength 345nm).

[0306] In addition, it was confirmed that CzCzPA-02 emits blue light. The compound of one embodiment of the present invention can be used as a luminescent material or a main body of a fluorescent luminescent material in the visible region. In addition, it is known that the thin film of CzCzPA-02 has a good film quality that is not easily condensed even in the atmosphere. [Example 7]

[0307] In this example, as a light-emitting element of one embodiment of the present invention, a light-emitting element 3 was manufactured using CzCzPA-02 (structural formula (220)) described in Example 6 for a light-emitting layer, and the results of measuring its characteristics are shown.

[0308] The light emitting element used in this embodiment has the same structure as that shown in Embodiment 3. Fig.13 The structure of the light emitting element in the embodiment is the same as that of the light emitting element in the embodiment, and the specific structure of each layer constituting the element structure is shown in Table 3. In addition, the chemical formula of the material used in this embodiment is shown below.

[0309] [Table 3] *CzCzPA-02:1,6mMemFLPAPrn(1:0.03 25nm)

[0310] [Chemical formula 26]

[0311] 《Operating characteristics of light-emitting elements》 The operating characteristics of the manufactured light emitting element 3 were measured. The measurement was performed at room temperature. Figure 26 to Figure 29 The results are shown.

[0312] In addition, Table 4 below shows that 1000 cd / m 2 The main initial characteristic values ​​of each nearby light-emitting element.

[0313] [Table 4]

[0314] From the above results, it can be seen that the light-emitting element 3 manufactured in this example can be driven at a low voltage and can display blue with good chromaticity at high efficiency.

[0315] in addition, Fig.30 Shown at 12.5 mA / cm 2 The emission spectrum when the current density is such that the current flows through the light emitting element 3. Fig.30 It can be seen that the emission spectrum of the light-emitting element is derived from the light-emitting substance contained in the light-emitting layer 913. [Example 8]

[0316] In this example, methods for synthesizing 9-(9-phenyl-9H-carbazole-3-yl)-7H-benzo[c]carbazole (PCcBCz (structural formula (400))) used for the synthesis of PCcBCzPA (structural formula (252)) shown in Example 4 and 9-(9-phenyl-9H-carbazole-2-yl)-7H-benzo[c]carbazole (PCcBCz-02 (structural formula (401))) used for the synthesis of PCcBCzPA-02 (structural formula (253)) shown in Example 5 are described. Note that the structures of PCcBCz and PCcBCz-02 are shown below.

[0317] [Chemical formula 27]

[0318] <Step 1: Synthesis of 9-chloro-7H-benzo[c]carbazole> 2.9 g (10 mmol) of 1-(4-chlorophenyl)-2-nitronaphthalene and 11 g of triphenylphosphine (40 mmol) and 50 mL of o-dichlorobenzene were placed in a 200 mL three-necked flask and stirred at 180° C. for 10 hours under a nitrogen stream. After the reaction, the mixture was purified by silica gel column chromatography (toluene: hexane = 1: 1) Purification was performed to obtain a solid. The obtained solid was washed with hexane to obtain 2.0 g of a white solid of the target substance at a yield of 80%. The synthesis scheme of step 1 is shown in (f-1) below.

[0319] [Chemical formula 28]

[0320] The magnetic resonance spectroscopy of the obtained white solid is shown below ( 1 H-NMR) analysis results. Fig.31A and Fig.31B Show 1 H-NMR spectrum. Note that Fig.31B Yes Fig.31A The spectrum is shown in an enlarged form in the range of 7.0 ppm to 9.0 ppm. The results show that 9-chloro-7H-benzo[c]carbazole, the target compound in (f-1) above, was obtained.

[0321] 1 H NMR (CDCl3, 300MHz): δ=7.34 (dd, J1=9.0Hz, J2=1.8Hz, 1H), 7.47-7.52 (m, 1H), 7.54 (d, J=2.1Hz, 1H), 7.61 (d, J=8. 7Hz, 1H), 7.68-7.74 (m, 1H), 7.87 (d, J=8.7Hz, 1H), 8.00 (d, J=7.8Hz, 1H), 8.43-8.46 (m, 2H), 8.69 (d, J=8.4Hz, 1H).

[0322] <Step 2-1: Synthesis of PCcBCz> In this step 2-1, a method for synthesizing PCcBCz using 9-chloro-7H-benzo[c]carbazole synthesized in the above step 1 is described.

[0323] 1.8 g (7.1 mmol) of 9-chloro-7H-benzo[c]carbazole synthesized in the above step 1, 2.2 g (7.1 mmol) of 9-phenyl-9H-carbazole-3-boric acid, 0.25 g (0.70 mmol) of di(1-adamantane)-n-butylphosphine, 4.6 g (22 mmol) of tripotassium phosphate, 1.6 g (22 mmol) of tert-butyl alcohol and 35 mL of diethylene glycol dimethyl ether were placed in a 200-mL three-necked flask, and the mixture was deaerated while being stirred.

[0324] 79 mg (0.35 mmol) of palladium (II) acetate was added to the mixture, and stirred at 160°C for 13 hours under a nitrogen stream. After the reaction, the solid was removed from the mixture by suction filtration, and the obtained filtrate was purified by silica gel column chromatography (chloroform: hexane = 1: 2) to obtain a solid. The obtained solid was washed with hexane, thereby obtaining 2.0 g of a light brown solid of the target product with a yield of 61%. The following (f-2-1) shows the synthesis scheme of the above-mentioned synthesis method.

[0325] [Chemical formula 29]

[0326] The magnetic resonance spectroscopy of the obtained light brown solid is shown below ( 1 H-NMR) analysis results. Fig.32A and Fig.32B Show 1 H-NMR spectrum. Note that Fig.32B Yes Fig.32A The spectrum is enlarged and shown in the range of 7.0 ppm to 9.0 ppm. From the results, it can be seen that PCcBCz (structural formula (400)), which is the target substance in (f-2-1) above, was obtained.

[0327] 1 H NMR (CDCl3, 300MHz): δ=7.30-7.36 (m, 1H), 7.44-7.53 (m, 5H), 7.60-7.66 (m, 5H), 7.71-7.81 (m, 3H), 7.86-7.89 ( m, 2H), 8.02 (d, J=7.8Hz, 1H), 8.23-8.25 (m, 1H), 8.47-8.49 (m, 2H), 8.63 (d, J=8.1Hz, 1H), 8.82 (d, J=8.4Hz, 1H).

[0328] <Step 2-2: Synthesis of PCcBCz-02> In this Step 2-2, a method for synthesizing PCcBCz-02 using 9-chloro-7H-benzo[c]carbazole synthesized in Step 1 is described.

[0329] 1.0 g (4.0 mmol) of 9-chloro-7H-benzo[c]carbazole synthesized in the above step 1, 1.2 g (4.0 mmol) of 9-phenyl-9H-carbazole-2-boric acid, 29 mg (0.080 mmol) of di(1-adamantane)-n-butylphosphine, 2.5 g (12 mmol) of tripotassium phosphate, 0.90 g (12 mmol) of tert-butyl alcohol and 20 mL of diethylene glycol dimethyl ether were placed in a 200-mL three-necked flask, and the mixture was degassed while being stirred under reduced pressure.

[0330] 9.0 mg (0.040 mmol) of palladium (II) acetate was added to the mixture, and the mixture was stirred at 120°C for 20 hours under a nitrogen stream. After the reaction, the solid was removed from the mixture by suction filtration, and the obtained filtrate was purified by silica gel column chromatography (toluene: hexane = 1: 2) to obtain a solid. The obtained solid was washed with hexane, thereby obtaining 0.91 g of a light brown solid of the target product with a yield of 50%. The following (f-2-2) shows the synthesis scheme of the above-mentioned synthesis method.

[0331] [Chemical formula 30]

[0332] The magnetic resonance spectroscopy of the obtained light brown solid is shown below ( 1 H-NMR) analysis results. Fig.33A and Fig.33B Show 1 H-NMR spectrum. Note that Fig.33B Yes Fig.33A The spectrum is enlarged and shown in the range of 7.0 ppm to 9.0 ppm. From the results, it can be seen that the target compound PCcBCz-02 (structural formula (401)) was obtained.

[0333] 1 H NMR (CDCl3, 300MHz): δ=7.27-7.33 (m, 1H), 7.40-7.52 (m, 4H), 7.61-7.73 (m, 9H), 7.81 (d, J=1.5Hz, 1H), 7.86 (d, J=8.7Hz, 1H), 7.99 (d, J=8.4Hz, 1H), 8.17 (d, J=7.8Hz, 1H), 8.23 ​​(d, J=9.0Hz, 1H), 8.41 (s, 1H), 8.57 (d, J=8.4Hz, 1H), 8.77 (d, J=7.8Hz, 1H). [Explanation of symbols]

[0334] 101 first electrode 102 second electrode 103EL layer 103a, 103b EL layer 104 Charge generation layer 111, 111a, 111b hole injection layer 112, 112a, 112b hole transport layer 113, 113a, 113b light emitting layer 114, 114a, 114b electron transport layer 115, 115a, 115b electron injection layer 201 First Substrate 202 Transistor (FET) 203R, 203G, 203B, 203W light emitting elements 204EL layer 205 Second substrate 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 Pixels 303 driving circuit unit (source line driving circuit) 304a, 304b driving circuit unit (gate line driving circuit) 305 sealant 306 Second substrate 307 lead wiring 308FPC 309FET 310FET 311FET 312FET 313 first electrode 314 Insulation 315EL layer 316 second electrode 317 light emitting element 318 Space 900 substrate 901 first electrode 902EL layer 903 second electrode 911 Hole injection layer 912Hole transport layer 913 Luminous Layer 914 electron transport layer 915 electron injection layer 4000 lighting fixtures 4001 substrate 4002 light emitting element 4003 substrate 4004 first electrode 4005EL layer 4006 Second Electrode 4007 electrode 4008 electrode 4009 auxiliary wiring 4010 insulation layer 4011 Sealing Substrate 4012 sealant 4013 Desiccant 4015 loose board 4100 lighting fixtures 4200 lighting fixture 4201 substrate 4202 light emitting element 4204 first electrode 4205EL layer 4206 Second Electrode 4207 electrode 4208 electrode 4209 auxiliary wiring 4210 insulation layer 4211 Sealing Substrate 4212 sealant 4213 Barrier Film 4214 planarization film 4215 loose board 4300 lighting fixtures 5101 lamp 5102 wheel hub 5103 Car Door 5104 Display 5105 Steering Wheel 5106 gear lever 5107 seats 5108 rearview mirror 7000 frame 7001 Display unit 7002 Second display unit 7003 Speaker 7004LED Light 7005 operation keys 7006 connection terminal 7007 Sensor 7008 Microphone 7009 switch 7010 infrared port 7011 Recording medium reading unit 7012 support part 7013 Headphones 7014 Antenna 7015 shutter button 7016 Receiving Department 7018 bracket 7019 Microphone 7020 Camera 7021 External connection 7022, 7023 operation buttons 7024 connection terminal 7025 strap, 7026 strap buckle 7027 Icon indicating time 7028 Other icons 8001 lighting fixture 8002 lighting fixtures 8003 lighting device 8004 Lighting Device 9310 Portable Information Terminal 9311 Display 9312 display area 9313 hinge part 9315 frame

Claims

1. An organic compound represented by formula (G1), In the formula: Ar represents an unsubstituted arylene group having 6 to 13 carbon atoms; Cz represents a carbazolyl group which is unsubstituted or substituted by a phenyl group at the 9-position; R 5 represents an unsubstituted phenyl group or an unsubstituted naphthyl group; R 16 represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a carbazolyl group which is unsubstituted or substituted with a phenyl group at the 9-position; R 11 To R 15 and R 17 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms; And, R 1 To R 4 and R 6 To R 9 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms.

2. An organic compound represented by formula (G1), In the formula: Ar represents an unsubstituted arylene group having 6 to 13 carbon atoms; Cz represents a carbazolyl group which is unsubstituted or substituted by a phenyl group at the 9-position; R 5 represents an unsubstituted phenyl group or an unsubstituted naphthyl group; R 11 To R 17 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms; R 1 To R 4 and R 6 To R 9 Each independently represents any one of hydrogen and an alkyl group having 1 to 6 carbon atoms; And, R 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 at least one fused ring.

3. The organic compound according to claim 1 or 2, The bonding position of Cz to the carbazole ring in the formula (G1) is the 9-position, 3-position or 2-position of the carbazole group represented by Cz.

4. The organic compound according to claim 1 or 2, Wherein Ar in the formula (G1) is an unsubstituted phenylene group or an unsubstituted biphenyldiyl group.

5. The organic compound according to claim 1 or 2, Wherein R in formula (G1) 5 It is phenyl.

6. An organic compound represented by formula (200), formula (220), formula (221), formula (252) or formula (253):

7. A light-emitting element using the organic compound according to any one of claims 1, 2 or 6.

8. A light emitting element comprising an EL layer between a pair of electrodes, in, The EL layer includes the organic compound according to any one of claims 1 , 2 or 6 .

9. A light emitting element comprising an EL layer between a pair of electrodes, in, The EL layer includes a light emitting layer, The light-emitting layer includes the organic compound according to any one of claims 1, 2 or 6.

10. A light emitting device, comprising: The light-emitting element according to claim 7; as well as At least one of a transistor and a substrate.

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