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

Abstract

Organic compound represented by the general formula (G1), where in the formula: Q Oxygen or sulfur; A 1 and A 2 each independently of each other a substituted or unsubstituted polycyclic aromatic hydrocarbon; m is an integer from 0 to 4; n is an integer from 1 to 4; and R 1 to R 12 Each independently of one another hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

Description

Technical field

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. It should be noted that an embodiment of the present invention is not limited to the aforementioned technical field. That is to say, an embodiment of the present invention relates to an object, a process, a manufacturing process, or an operating method. Another embodiment of the present invention relates to a process, a machine, a product, or a composition (composition of a material). In particular, examples include a semiconductor device, a display device, a liquid crystal display device, and the like. State of the art

[0002] A light-emitting element that incorporates an EL layer between a pair of electrodes (also known as an organic EL element) has properties such as thinness and lightness, a high response speed to input signals, and low power consumption; therefore, a display incorporating such a light-emitting element has attracted attention as a next-generation flat panel display.

[0003] In a light-emitting atom, a voltage applied between a pair of electrodes causes recombination of electrons and holes injected by the electrodes in an EL layer, and a light-emitting substance (organic compound) contained in the EL layer is excited to a specific state. Light is emitted when the light-emitting substance returns from the excited state to its ground state. It should be noted that the excited state can be a singlet excitation state (S*) or a triplet excitation state (T*). Light emission from a singlet excitation state is called fluorescence, and light emission from a triplet excitation state is called phosphorescence. The statistical production ratio of these phenomena in a light-emitting atom is generally assumed to be S*:T* = 1:3.Since the spectrum of light emitted by a light-emitting substance depends on the light-emitting substance itself, light-emitting elements with different colors can be obtained by using different types of organic compounds as light-emitting substances.

[0004] To improve the elemental properties of such a light-emitting element, improvements to the elemental structure, the development of a material, and the like have been actively carried out (see, for example, patent document 1). [Reference][Patent document] [Patent Document 1] Japanese Patent Publication No. 2010-182699

[0005] JP 2017119682 A concerns the provision of a highly reliable connection and light-emitting element.

[0006] KR 1020180022608 A relates to a compound and an organic light-emitting diode containing it.

[0007] US 20170352447 A1 relates to an organic heterocyclic compound and an organic light-emitting diode containing it.

[0008] The compounds of JP 2017119682 A, KR 1020180022608 and US 20170352447 A1 exhibit structural differences compared to the claimed compounds. Summary of the invention Problem to be solved by the invention

[0009] The present invention is described in the independent claims. Advantageous embodiments are specified in the dependent claims. In one embodiment of the present invention, a novel organic compound comprising a benzofuropyrimidine framework or a benzothienopyrimidine framework and a polycyclic aromatic hydrocarbon is provided. In another embodiment of the present invention, a benzofuropyrimidine derivative or a benzothienopyrimidine derivative is provided, which is a novel organic compound. In a further embodiment of the present invention, a novel organic compound is provided that can be used in a light-emitting element. In a further embodiment of the present disclosure, a novel organic compound is provided that can be used in an EL layer of a light-emitting element.Furthermore, a highly reliable and novel light-emitting element is provided, in which a novel organic compound of an embodiment of the present invention is used. A novel light-emitting device, a novel electronic device, or a novel lighting device is also provided. It should be noted that the description of these problems does not preclude the existence of further problems. It should be noted that an embodiment of the present invention need not necessarily fulfill all of these problems. It should be noted that further problems will become apparent from the explanation of the description, the drawings, the claims, and the like, and further problems may be derived from the explanation of the description, the drawings, the claims, and the like. Means to solve the problem

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

[0011] In the above general formula (G1), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0012] Another embodiment of the present invention is an organic compound represented by the general formula (G2) below.

[0013] In the above general formula (G2), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0014] Another embodiment of the present invention is an organic compound represented by the general formula (G3) below.

[0015] In the above general formula (G3), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0016] It should be noted that in each of the above structures A 1 and A2 Each is independently a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group.

[0017] Furthermore, in each of the above structures A 1 and A 2 each independently one of the following general formulas (A-1) to (A-14).

[0018] In the above general formulas (A-1) to (A-14) R A1 to R A15 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0019] Another embodiment of the present invention is an organic compound represented by the general formula (G4) below.

[0020] In the general formula above (G4), Q represents oxygen or sulfur. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 30 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0021] Another embodiment of the present invention is an organic compound represented by the general formula (G5) below.

[0022] In the general formula above (G5), Q represents oxygen or sulfur. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 30 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0023] Another embodiment of the present invention is an organic compound represented by a structural formula (100).

[0024] Another embodiment of the present invention is a light-emitting element comprising the aforementioned organic compound of an embodiment of the present invention. It should be noted that the present disclosure also includes a light-emitting element that utilizes the organic compound of an embodiment of the present invention for an EL layer between a pair of electrodes and a light-emitting layer within the EL layer. In addition to the light-emitting element, a light-emitting device comprising a transistor, a substrate, and the like is also included within the scope of the invention.Furthermore, the scope of protection of the invention includes, in addition to the light-emitting device, an electronic device and a lighting device comprising a microphone, a camera, an operating button, an external connection section, a housing, a cover, a bracket, a loudspeaker and the like.

[0025] Furthermore, the scope of protection of one embodiment of the present invention includes a light-emitting device comprising a light-emitting element and a lighting device comprising the light-emitting device. The light-emitting device in this description therefore refers to an image display device or a light source (including a lighting device). The light-emitting device also includes the following within its category: a module in which a connector, such as a flexible printed circuit (FPC) or a tape carrier package (TCP), is mounted on a light-emitting device; a module in which a printed circuit board is provided at the end of a TCP; and a module in which an integrated circuit (IC) is mounted directly on a light-emitting element by a chip-on-glass (COG) method. Effect of the invention

[0026] In one embodiment of the present invention, a novel organic compound comprising a benzofuropyrimidine framework or a benzothienopyrimidine framework and a polycyclic aromatic hydrocarbon is provided. In another embodiment of the present invention, a benzofuropyrimidine derivative or a benzothienopyrimidine derivative is provided, which is a novel organic compound. In a further embodiment of the present invention, a novel organic compound is provided that can be used in a light-emitting element. In a further embodiment of the present invention, a novel organic compound is provided that can be used in an EL layer of a light-emitting element.Furthermore, a highly reliable and novel light-emitting element is provided, in which a novel organic compound of an embodiment of the present invention is used. A novel light-emitting device, a novel electronic device, or a novel lighting device is also provided. It should be noted that the description of these effects does not preclude the existence of further effects. It should be noted that an embodiment of the present invention need not necessarily fulfill all of these effects. It should be noted that further effects may become apparent from the explanation of the description, the drawings, the claims, and the like, and further effects may be derived from the explanation of the description, the drawings, the claims, and the like. Brief description of the drawings [ Fig. 1] Representations depicting the structures of light-emitting elements. [ Fig. 2] Illustrations depicting light-emitting devices. [ Fig. 3] Illustrations depicting a light-emitting device. [ Fig. 4] Illustrations depicting electronic devices. [ Fig. 5] Illustrations depicting an electronic device. [ Fig. 6] Illustrations depicting a vehicle. [ Fig. 7] Illustrations depicting lighting devices. [ Fig. 8] a 1 H-NMR diagram of an organic compound represented by the structural formula (100). [ Fig. 9] Representations showing a UV-VIS absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (100). [ Fig. 10] a representation that depicts a light-emitting element. [ Fig. 11] a representation showing the current density-luminance properties of a light-emitting element 1 and a light-emitting comparison element 2. [ Fig. 12] a representation showing the voltage-luminance properties of the light-emitting element 1 and the light-emitting comparison element 2. [ Fig. 13] a representation showing the luminance-current efficiency properties of the light-emitting element 1 and the light-emitting comparison element 2. [ Fig. 14] a representation showing the voltage-current characteristics of the light-emitting element 1 and the light-emitting comparison element 2. [ Fig. 15] a representation showing the emission spectra of the light-emitting element 1 and the light-emitting comparison element 2. [ Fig. 16] a representation showing the reliability of the light-emitting element 1 and the light-emitting comparison element 2. [ Fig. 17] a representation that a 1 H-NMR diagram of an organic compound represented by the structural formula (130). [ Fig. 18] Representations showing a UV-VIS absorption spectrum and an emission spectrum of the organic compound represented by the structural formula (130). [ Fig. 19] a representation that depicts the current density-luminance properties of a light-emitting element 3. [ Fig. 20] a representation that depicts the voltage-luminance properties of a light-emitting element 3. [ Fig. 21] a representation showing the luminance-current efficiency properties of the light-emitting element 3. [ Fig. 22] a representation that depicts the voltage-current properties of the light-emitting element 3. [ Fig. 23] a representation showing an emission spectrum of the light-emitting element 3. [ Fig. 24] a representation that shows the reliability of the light-emitting element 3. Best way to implement the invention

[0027] Embodiments of the present invention are described below with reference to the drawings. It should be noted that the present invention is not limited to the following description; the types and details of the present invention can be modified in various ways without departing from the basic concept and scope of protection of the present invention. Therefore, the present invention should not be considered as limited to the description of the following embodiments.

[0028] It should be noted that the position, size, area, or the like of each component shown in drawings and the like is, in some cases, not shown precisely for ease of understanding. The disclosed invention is therefore not necessarily limited to the position, size, area, or the like shown in the drawings and the like.

[0029] In the explanation of the embodiments of the present invention in this description and the like, based on the drawings, identical components in different drawings are generally provided with the same reference numeral. (Version 1)

[0030] In this embodiment, organic compounds of embodiments of the present invention are described. It should be noted that the organic compound of one embodiment of the present invention is a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, represented by the general formula (G1) below. It should be noted that the organic compound of one embodiment of the present invention is suitable as a host material for a phosphorescent material due to its high T1 level.

[0031] It should be noted that in the general formula (G1), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0032] Another embodiment of the present invention is an organic compound represented by the general formula (G2) below.

[0033] In the above general formula (G1), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0034] Another embodiment of the present invention is an organic compound represented by the general formula (G3) below.

[0035] In the above general formula (G3), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0036] A 1 and A 2 In the above general formula (G1), (G2) or (G3) each represent, independently of one another, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthrenyl group or a substituted or unsubstituted triphenylenyl group.

[0037] Furthermore, A 1 and A 2 In the above general formula (G1), (G2) or (G3), each is independently one of the following general formulas (A-1) to (A-14).

[0038] It should be noted that in the above general formulas (A-1) to (A-14) R A1 to R A15 Each can independently represent hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0039] Another embodiment of the present invention is an organic compound represented by the general formula (G4) below.

[0040] In the general formula above (G4), Q represents oxygen or sulfur. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 30Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0041] Another embodiment of the present invention is an organic compound represented by the general formula (G5) below.

[0042] In the general formula above (G5), Q represents oxygen or sulfur. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 30Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0043] It should be noted that in the case where the above general formula (G1), (G2), (G3), (G4) or (G5) contains a substituted or unsubstituted polycyclic aromatic hydrocarbon, the substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, the substituted or unsubstituted aryl group with 6 to 13 carbon atoms, the substituted or unsubstituted fluorenyl group, the substituted or unsubstituted spirofluorenyl group, the substituted or unsubstituted phenanthrenyl group or the substituted or unsubstituted triphenylenyl group, the following are given as examples of the substituent: an alkyl group with 1 to 7 carbon atoms, such asa methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group or a hexyl group; a cycloalkyl group with 5 to 7 carbon atoms, such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or an 8,9,10-trinorbornanyl group; and an aryl group with 6 to 12 carbon atoms, such as a phenyl group, a naphthyl group or a biphenyl group.

[0044] Specific examples of the polycyclic aromatic hydrocarbon in the above general formula (G1), (G2) or (G3) include a fluorenyl group, a spirofluorenyl group, a phenanthrenyl group or a triphenylenyl group. As shown, the organic compound of an embodiment of the present invention comprises a polycyclic aromatic hydrocarbon with the high T1 level.

[0045] Specific examples of the alkyl group with 1 to 6 carbon atoms in the above general formula (G1), (G2), (G3), (G4) or (G5) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-dimethylbutyl group and a 2,3-dimethylbutyl group.

[0046] Furthermore, specific examples of the cycloalkyl group with 3 to 7 carbon atoms in the above general formula (G1), (G2), (G3), (G4) or (G5) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-methylcyclohexyl group, a cycloheptyl group and a norbornanyl group.

[0047] Furthermore, specific examples of the aryl group with 6 to 13 carbon atoms in the above general formula (G1), (G2), (G3), (G4) or (G5) include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, a 1-naphthyl group, a 2-naphthyl group and a fluorenyl group.

[0048] Next, specific structural formulas of the aforementioned organic compounds from embodiments of the present invention are shown below. It should be noted that the present invention is not limited to these formulas.

[0049] It should be noted that the organic compounds represented by the preceding structural formulas (100) to (130) are examples of the organic compound represented by the preceding general formula (G1), (G2), (G3), (G4) or (G5). The organic compound of an embodiment of the present invention is not limited thereto.

[0050] Next, an example of a method for synthesizing an organic compound of an embodiment of the present invention, represented by the general formula (G1), will be described.

[0051] In the general formula (G1), Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each represents, independently of each other, a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms. < <Verfahren zum Synthetisieren der organischen Verbindung, die durch die allgemeine Formel (G1) dargestellt wird> >

[0052] Various reactions can be used for the synthesis of the organic compound represented by the general formula (G1) above. For example, the organic compound represented by the general formula (G1) can be synthesized by a simple procedure illustrated by synthesis schemes below.

[0053] First, as shown in the scheme (A) below, a dihalo compound (a1) reacts with boronic acid compounds (a2) and (a3) ​​to yield the organic compound represented by the general formula (G1). It should be noted that the dihalo compound (a1) comprises a substituted or unsubstituted benzofuropyrimidine skeleton or a substituted or unsubstituted benzothienopyrimidine skeleton. Furthermore, the boronic acid compounds (a2) and (a3) ​​comprise a substituted or unsubstituted polycyclic aromatic hydrocarbon.

[0054] It should be noted that in the above synthesis scheme (A), X represents a halogen and Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon. B 1 and B 2represent a boronic acid, a borosilicate ester, a cyclic triolborate salt, or the like. A lithium salt, a potassium salt, or a sodium salt can also be used as a cyclic triolborate salt. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0055] Furthermore, the organic compound represented by the general formula (G1) can also be obtained by reacting the dihalate (a1) with boronic compounds (b1) and (b2) to give an intermediate (d1), as shown in the scheme (B) below, and then reacting the intermediate (d1) with boronic compounds (b3) and (b4). It should be noted that the dihalate (a1) comprises a substituted or unsubstituted benzofuropyrimidine skeleton or a substituted or unsubstituted benzothienopyrimidine skeleton. Furthermore, the boronic compounds (b1) and (b2) comprise a substituted or unsubstituted phenyl group. Furthermore, the boronic compounds (b3) and (b4) comprise a substituted or unsubstituted polycyclic aromatic hydrocarbon group.

[0056] It should be noted that in the above synthesis scheme (B), X represents a halogen and Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon. B 1 to B 4 represent a boronic acid, a borosilicate ester, a cyclic triolborate salt, or the like. A lithium salt, a potassium salt, or a sodium salt can also be used as a cyclic triolborate salt. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0057] Furthermore, the organic compound represented by the general formula (G1) can also be obtained by reacting a halogen compound (c1) with the boronic acid compound (a2), as shown in the scheme (C) below. It should be noted that the halogen compound (c1) comprises a benzofuropyrimidine or benzothienopyrimidine framework containing a substituted or unsubstituted polycyclic aromatic hydrocarbon. The boronic acid compound (a2) further comprises a phenyl group containing a substituted or unsubstituted polycyclic aromatic hydrocarbon.

[0058] It should be noted that in the above synthesis scheme (C), X represents a halogen and Q represents oxygen or sulfur. Furthermore, A 1 and A 2 Each independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon. B 1represents a boronic acid, a borosilicate ester, a cyclic triolborate salt, or the like. A lithium salt, a potassium salt, or a sodium salt can also be used as the cyclic triolborate salt. Furthermore, m represents an integer from 0 to 4. Furthermore, n represents an integer from 1 to 4. Furthermore, R 1 to R 12 Each independently represents hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms.

[0059] It should be noted that many different benzofuropyrimidine derivatives or benzothienopyrimidine derivatives, represented by the general formula (G1), can be synthesized, since various types of the dihalate (a1), the boronic compounds (a2) and (a3), the boronic compounds (b1) and (b2), the boronic compounds (b3) and (b4), and the halogen (c1) used in the preceding synthesis schemes (A), (B), and (C) are commercially available or can be synthesized. Thus, the compound of an embodiment of the present invention is highly variable.

[0060] Although an example of the organic compound of an embodiment of the present invention and the method for preparing it have been described, the present invention is not limited thereto and can be synthesized using another synthesis method.

[0061] The structure described in this embodiment can optionally be used in combination with any of the structures described in the other embodiments. (Version 2)

[0062] In this embodiment, a light-emitting element containing any of the organic compounds described in embodiment 1 is used, based on Fig. 1 described. <<Grundlegende Struktur des Licht emittierenden Elements> >

[0063] First, a basic structure of a light-emitting element is described. Fig. Figure 1(A) represents an example of a light-emitting element that includes an EL layer with a light-emitting layer between a pair of electrodes. In particular, an EL layer 103 is provided between a first electrode 101 and a second electrode 102.

[0064] Fig. 1(B) represents an example of a light-emitting element having a multilayer structure (tandem structure) in which a plurality of EL layers (two EL layers 103a and 103b in Fig. 1 (B)) is provided between a pair of electrodes and a charge-generating layer 104 is provided between the EL layers. Using such a light-emitting tandem element, a light-emitting device with low power consumption that can be operated at a low voltage can be obtained.

[0065] The charge-generating layer 104 has a function for injecting electrons into one of the EL layers (103a or 103b) and for injecting holes into the other of the EL layers (103a or 103b) when a voltage is applied between the first electrode 101 and the second electrode 102. Therefore, injected into Fig. 1(B) the charge-generating layer 104 injects electrons into the EL layer 103a and injects holes into the EL layer 103b when a voltage is applied such that the potential of the first electrode 101 becomes higher than that of the second electrode 102.

[0066] It should be noted that, with regard to light extraction efficiency, the charge-generating layer 104 preferably has a visible light transmittance (in particular, the charge-generating layer 104 has a visible light transmittance of 40% or more). The charge-generating layer 104 functions even if it has a lower conductivity than the first electrode 101 or the second electrode 102.

[0067] In Fig. 1(C) presents an example in which the Fig. 1(A) shows that the EL layer 103 has a multilayer structure (the same applies in the case where the in Fig. The EL layers (103a, 103b) shown in Figure 1(B) have a multilayer structure. However, it should be noted that in this case, the first electrode 101 is considered to serve as the 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 arranged in that order over the first electrode 101. It should be noted that in the case where, as in Fig. 1(B) contains a plurality of EL layers, the EL layers are arranged sequentially on top of each other from the anode side. If the first electrode 101 is a cathode and the second electrode 102 is an anode, the arrangement order of the EL layers is reversed.

[0068] The light-emitting layer 113, contained within the EL layers (103, 103a, and 103b), contains a suitable combination of a light-emitting substance and a variety of other substances, such that fluorescence or phosphorescence of a desired emission color can be obtained. The light-emitting layer 113 can have a multilayered structure with different emission colors. In this case, the light-emitting substance and other substances are different between the stacked light-emitting layers. Alternatively, the numerous EL layers (103a and 103b) can be arranged in Fig. 1(B) exhibit their respective emission colors. In this case too, the light-emitting substance and other substances between the light-emitting layers are different.

[0069] The light-emitting element of an embodiment of the present invention may have an optical microresonator (microcavity) structure, for example, in Fig. 1(C) the first electrode 101 is a reflective electrode and the second electrode 102 is a transflective electrode. Therefore, light emission from the light-emitting layer 113 can be brought to resonance in the EL layer 103 between the electrodes, and light emission obtained via the second electrode 102 can be amplified.

[0070] It should be noted that if the first electrode 101 of the light-emitting element is a reflective electrode having a multilayer structure consisting of a reflective conductive material and a translucent conductive material (a transparent conductive film), optical adjustment can be achieved by controlling the thickness of the transparent conductive film. In particular, if the wavelength of the light obtained from the light-emitting layer 113 is λ, the distance between the first electrode 101 and the second electrode 102 is preferably set to approximately mλ / 2 (where m is a natural number).

[0071] To amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the optical path length from the first electrode 101 to a region of the light-emitting layer 113 where the desired light is obtained (light-emitting region), and the optical path length from the second electrode 102 to the region of the light-emitting layer 113 where the desired light is obtained (light-emitting region), are preferably set to approximately (2m'+1)λ / 4 (m' is a natural number). Here, the light-emitting region denotes a region of the light-emitting layer 113 where holes and electrons recombine.

[0072] By such optical adjustment, the spectrum of specific monochromatic light obtained from the light-emitting layer 113 can be narrowed and light emission with high color purity can be obtained.

[0073] In this case, the optical path length between the first electrode 101 and the second electrode 102 is more precisely the total thickness from a reflection region in the first electrode 101 to a reflection region in the second electrode 102. However, it is difficult to determine the reflection regions in the first electrode 101 and the second electrode 102 precisely; therefore, it is assumed that the aforementioned effect can be achieved sufficiently regardless of the location of the reflection regions in the first electrode 101 and the second electrode 102. Furthermore, the optical path length between the first electrode 101 and the light-emitting layer that emits the desired light is more precisely the optical path length between the reflection region in the first electrode 101 and the light-emitting region in the light-emitting layer that emits the desired light.However, it is difficult to precisely determine the reflection area in the first electrode 101 and the light-emitting area in the light-emitting layer that emits the desired light; therefore, it is assumed that the above effect can be sufficiently achieved regardless of where the reflection area and the light-emitting area are located in the first electrode 101 and the light-emitting layer that emits the desired light, respectively.

[0074] In the case where the light-emitting element is in Fig. Because 1(C) has a microcavity structure, light (monochromatic light) of different wavelengths can be extracted, even when using the same EL layer. Therefore, separate dyeing to obtain a variety of emission colors (e.g., red, green, and blue) is not necessary. Furthermore, high resolution can be easily achieved. Combination with color layers (color filters) is also possible. Additionally, the emission intensity of light with a specific wavelength can be increased in the forward direction, thereby reducing power consumption.

[0075] A in Fig. The light-emitting element shown in Figure 1(E) is an example of the one shown in Figure 1(E). Fig. Figure 1(B) shows a light-emitting element with a tandem structure, comprising, as depicted in the drawing, three EL layers (103a, 103b, and 103c) stacked on top of each other, with charge-generating layers (104a and 104b) positioned between them. Each of the three EL layers (103a, 103b, and 103c) contains light-emitting layers (113a, 113b, and 113c), and the emission colors of these layers are freely selectable. For example, light-emitting layer 113a can be blue, light-emitting layer 113b can be red, green, or yellow, and light-emitting layer 113c can be blue. Alternatively, light-emitting layer 113a can be red, light-emitting layer 113b can be blue, green, or yellow, and light-emitting layer 113c can be red.

[0076] In the light-emitting element of an embodiment of the present invention, the first electrode 101 and / or the second electrode 102 is a translucent electrode (e.g., a transparent electrode or a transflective electrode). In the case where the translucent electrode is a transparent electrode, the transparent electrode has a visible light transmittance of 40% or higher. In the case where the translucent electrode is a transflective electrode, the transflective electrode has a visible light reflectance of 20% or higher and 80% or lower, and preferably 40% or higher and 70% or lower. These electrodes preferably have a resistivity of 1 × 10⁻⁶ -2 Ωcm or less.

[0077] Furthermore, if the first electrode 101 or the second electrode 102 in the light-emitting element of an embodiment of the present invention is a reflective electrode, the reflectivity for visible light of the reflective electrode is greater than or equal to 40% and less than or equal to 100%, and preferably greater than or equal to 70% and less than or equal to 100%. These electrodes preferably have a resistivity of 1 × 10 -2 Ωcm or less. <<Spezifische Struktur und Herstellungsverfahren von Licht emittierenden Elementen> >

[0078] Next, specific structures and manufacturing processes of in Fig. Figure 1 describes the light-emitting elements of embodiments of the present invention. It should be noted that this does not refer to just one light-emitting element, as in Figure 1. Fig. 1(A) and Fig. 1(C) the EL layer 103 has a single-layer structure, but also a light-emitting element, which, as in Fig. 1(B), Fig. 1(D) and Fig. 1(E) exhibits a tandem structure and can be described collectively. It should be noted that in the case where the light-emitting elements in Fig. 1. Each electrode has a microcavity structure, for example, the first electrode 101 is configured as a reflective electrode and the second electrode 102 as a transflective electrode. Furthermore, a single-layer or multi-layer structure can be formed using one or more types of desired electrode materials. The second electrode 102 is further formed after the formation of the EL layers (103, 103b), using a material as described above. A sputtering process or a vacuum evaporation process can be used to fabricate these electrodes. <Erste Elektrode und zweite Elektrode>

[0079] Any of the following materials, in a suitable combination, can be used for the first electrode 101 and the second electrode 102, as long as the functions of the electrodes described above can be fulfilled. For example, a metal, an alloy, an electrically conductive compound, a mixture thereof, and the like can be used in a suitable manner. In particular, an In-Sn oxide (also known as ITO), an In-Si-Sn oxide (also known as ITSO), an In-Zn oxide, an In-W-Zn oxide, or the like can be used. Furthermore, a metal, such as…Aluminum (Al), titanium (Ti), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga), zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum (Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium (Y), or neodymium (Nd), or an alloy containing a suitable combination of any of these metals, may be used. An element of Group 1 or an element of Group 2 of the periodic table not described above (e.g., lithium (Li), cesium (Cs), calcium (Ca), or strontium (Sr)), a rare-earth metal such as europium (Eu) or ytterbium (Yb), an alloy containing a suitable combination of any of these elements, graphene, or the like may also be used.

[0080] If the first electrode 101 is an anode, hole injection layers (111, 111a) and hole transport layers (112, 112a) of the EL layers (103, 103a) are sequentially arranged over the first electrode 101 by a vacuum evaporation process. It should be noted that in the Fig. 1(D) light-emitting element with a tandem structure after the sequential formation of the EL layer 103a and the charge generation layer 104, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are formed sequentially on top of the charge generation layer 104 in a similar manner. <Lochinjektionsschicht und Lochtransportschicht>

[0081] The hole injection layers (111, 111a and 111b) inject holes from the first electrode 101, which is an anode, and the charge generation layer (104) into the EL layers (103, 103a and 103b) and each contain a material with a high hole injection property.

[0082] Examples of materials with high hole injection properties include transition metal oxides such as molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, and manganese oxide. Alternatively, any of the following materials can be used: phthalocyanine-based compounds, such as phthalocyanine (abbreviation: H₂Pc) and copper phthalocyanine (abbreviation: CuPC); aromatic amine compounds, such as 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB) and N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD); high-molecular-weight compounds, such as... B. Poly(3,4-ethylenedioxythiophene) / Poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS); and the like.

[0083] Alternatively, a composite material containing a hole transport material and an acceptor material (electron acceptor material) can be used as a material with high hole injection properties. In this case, the acceptor material extracts electrons from the hole transport material, so that holes are created in the hole injection layers (111, 111a and 111b) and the holes are injected through the hole transport layers (112, 112a and 112b) into the light-emitting layers (113, 113a and 113b).It should be noted that each of the hole injection layers (111, 111a and 111b) can be designed to have a single-layer structure using a composite material containing a hole transport material and an acceptor material (electron acceptor material), or a multi-layer structure in which a layer containing a hole transport material and a layer containing an acceptor material (electron acceptor material) are arranged on top of each other.

[0084] The hole transport layers (112, 112a, and 112b) transport the holes injected by the hole injection layers (111, 111a, and 111b) from the first electrode 101 and the charge generation layer (104) to the light-emitting layers (113, 113a, and 113b). It should be noted that the hole transport layers (112, 112a, and 112b) each contain a hole transport material. It is particularly preferred that the HOMO level of the hole transport material contained in the hole transport layers (112, 112a, and 112b) is equal to or close to that of the hole injection layers (111, 111a, and 111b).

[0085] Examples of the acceptor material used for the hole injection layers (111, 111a, and 111b) include an oxide of a metal belonging to one of groups 4 to 8 of the periodic table. Specific examples include molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tungsten oxide, manganese oxide, and rhenium oxide. Among these oxides, molybdenum oxide is particularly preferred because it is stable in air, has low hygroscopic properties, and is easy to handle. Alternatively, organic acceptors, such as a quinodimethane derivative, a chloranil derivative, and a hexaazatriphenylene derivative, can be used.Examples of compounds with an electron-withdrawing group (a halogen group or a cyano group) include 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT-CN), and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (abbreviation: F6-TCNNQ). A compound in which electron-withdrawing groups are bonded to a fused aromatic ring with a variety of heteroatoms, such as HAT-CN, is particularly preferred because of its thermal stability. A [3]radialene derivative comprising an electron-withdrawing group (in particular a cyano group or a halogen group, such as a fluorine group) exhibits a very high electron-accepting property and is therefore preferred.Specific examples include α,α',α''-1,2,3-cyclopropanetriylidentris[4-cyano-2,3,5,6-tetrafluorobenzolacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidentris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)benzolacetonitrile] and α,α',α''-1,2,3-cyclopropanetriylidentris[2,3,4,5,6-pentafluorobenzolacetonitrile].

[0086] The hole transport materials used for the hole injection layers (111, 111a and 111b) and the hole transport layers (112, 112a and 112b) are preferably substances with a hole mobility of greater than or equal to 10 -6 cm 2 / Vs. It should be noted that other substances can be used as long as the substances have a hole transport property that is higher than an electron transport property.

[0087] Preferred hole transport materials are π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives and indole derivatives) and aromatic amine compounds; specific examples include compounds with an aromatic amine skeleton, such as... B. 4,4'-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), 4-Phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-Phenyl-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[4-(9-Phenanthryl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn), N-(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-Diphenyl-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4"-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-Phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 4,4',4''-Tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA), 4,4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA) and 4,4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB); compounds with a carbazole skeleton, such as 1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-Bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-Bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-Tris[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB) and 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA); compounds with a thiophene skeleton, such as... B. 4,4',4"-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) and 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV); and compounds with 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-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II).,

[0088] A high molecular weight compound, such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA) or poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: poly-TPD), can also be used.

[0089] It should be noted that the hole transport material is not limited to the examples above and can be one of several known materials or a combination of several known materials and is used for the hole injection layers (111, 111a and 111b) and the hole transport layers (112, 112a and 112b). It should also be noted that the hole transport layers (112, 112a and 112b) can each be formed from a plurality of layers. That is, the hole transport layers can each have a multilayered structure consisting of a first hole transport layer and a second hole transport layer.

[0090] In the Fig. In the light-emitting elements shown in Figure 1, the light-emitting layers (113, 113a) are formed by a vacuum evaporation process over the hole transport layers (112, 112a) of the EL layers (103, 103a). It should be noted that in the Fig. 1(D) light-emitting element with a tandem structure, a light-emitting layer 113b is formed after the formation of the EL layer 103a and the charge generation layer 104 also over the hole transport layer 112b of the EL layer 103b by a vacuum evaporation process. <Licht emittierende Schicht>

[0091] The light-emitting layers (113, 113a, 113b, and 113c) each contain a light-emitting substance. It should be noted that the light-emitting substance used is a substance whose emission color is blue, violet, blue-violet, green, yellow-green, yellow, orange, red, or the like. If the multiple light-emitting layers (113a, 113b, and 113c) are formed using different light-emitting substances, different emission colors can be emitted (for example, complementary emission colors are combined to obtain white light emission). Furthermore, a multilayer structure can be used in which a light-emitting layer contains two or more types of light-emitting substances.

[0092] The light-emitting layers (113, 113a, 113b and 113c) can each contain, in addition to a light-emitting substance (guest material), one or more types of organic compounds (a host material and an auxiliary material). The hole transport material and / or the electron transport material described in this embodiment can be used as one or more types of organic compounds.

[0093] The light-emitting substance that can be used for the light-emitting layers (113, 113a, 113b and 113c) can be a light-emitting substance that converts singlet excitation energy into light emission in the visible light range, or a light-emitting substance that converts triplet excitation energy into light emission in the visible light range.

[0094] Examples of other light-emitting substances are given below.

[0095] As an example of a light-emitting substance that converts singlet excitation energy into light emission, a substance that emits fluorescence (fluorescent material) can be given. Examples of substances that emit fluorescence include a pyrene derivative, an anthracene derivative, a triphenylene derivative, a fluorene derivative, a carbazole derivative, a dibenzothiophene derivative, a dibenzofuran derivative, a dibenzoquinoxaline derivative, a quinoxaline derivative, a pyridine derivative, a pyrimidine derivative, a phenanthrene derivative, and a naphthalene derivative. A pyrene derivative is particularly preferred because it has a high emission quantum yield.Specific examples of the pyrene derivative include N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), (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) and N,N'-(pyrene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-03).

[0096] Furthermore, it is possible to obtain 5,6-Bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine (abbreviation: PAP2BPy), 5,6-Bis[4'-(10-phenyl-9-anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N,N'-Bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA), Perylene, 2,5,8,11-Tetra(tert-butyl)perylene (abbreviation: TBP), N,N''-(2-tert-Butylanthracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-Diphenyl-N-[4-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA), N-[4-(9,to use 10-Diphenyl-2-anthryl)phenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) or the like.

[0097] Examples of a light-emitting substance that converts triplet excitation energy into light emission include a substance that emits phosphorescence (phosphorescent material) and a thermally activated delayed fluorescent (TADF) material that exhibits thermally activated delayed fluorescence.

[0098] Examples of phosphorescent materials include a metal-organic complex, a metal complex (platinum complex), and a rare-earth metal complex. These substances exhibit their respective emission colors (emission peaks), and therefore any one of them is selected appropriately depending on the requirements.

[0099] Examples of phosphorescent materials that emit blue or green light and whose emission spectrum has a peak wavelength greater than or equal to 450 nm and less than or equal to 570 nm include the following substances.

[0100] For example, organometallic complexes with a 4H-triazole skeleton, such as Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN 2]phenyl-rC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Mptz)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPrptz-3b)3]) and Tris[3-(5-biphenyl)-5-isopropyl-4-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(iPr5btz)3]); organometallic complexes with a 1H-triazole skeleton, such as... B. Tris[3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1-mp)3]) and Tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]); organometallic complexes with an imidazole skeleton, such asfac-Tris[1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir(iPrpmi)3]) and Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]); organometallic complexes in which a phenylpyridine derivative with an electron-withdrawing group is a ligand, such as Bis[2-(4',6'-difluorophenyl)pyridinato-N,C. 2' ]iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]Iridium(III)picolinate (abbreviation: Firpic), Bis{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N, C 2'}iridium(II I)picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) and Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2' ]iridium(III)acetylacetonate (abbreviation: Flr(acac)); and the like.

[0101] Examples of phosphorescent materials that emit green or yellow light and whose emission spectrum has a peak wavelength greater than or equal to 495 nm and less than or equal to 590 nm include the following substances.

[0102] For example, organometallic iridium complexes with a pyrimidine framework, such as... B. Tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]), (Acetylacetonato)bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)2(acac)]), (Acetylacetonato)bis(6-tert-butyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(acac)]), (Acetylacetonato)bis[6-(2-norbornyl)-4-phenylpyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]), (Acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenylpyrimidinato]iridium(III) (Abbreviation: [Ir(mpmppm)2(acac)]), (Acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethylphenyl)-4-pyrimidinyl-κN 3]phenyl-rC}iridium(III) (abbreviation: [Ir(dmppm-dmp)2(acac)]) and (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2(acac)]); organometallic iridium complexes with a pyrazine framework, such as (acetylacetonato)bis(3,5-dimethyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac)]) and (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyrazinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]); organometallic iridium complexes with a pyridine framework, such as B. Tris(2-phenylpyridinato-N,C 2' )iridium(III) (abbreviation: [Ir(ppy)3]), Bis(2-phenylpyridinato-N, C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(ppy)2acac]), Bis(benzo[h]quinolinato)iridium(III)acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(benzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), Tris(2-phenylquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(pq)3]), Bis(2-phenylquinolinato-N,C 2')iridium(III)acetylacetonate (abbreviation: [Ir(pq)2(acac)]), [2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]bis[2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: Ir(ppy)2(4dppy)) and Bis[2-(2-pyridinyl-κN)phenyl-κC][2-(4-methyl-5-phenyl-2-pyridinyl-κM)phenyl-κC]; organometallic complexes, such as Bis(2,4-diphenyl-1,3-oxazolato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(dpo)2(acac)]), Bis{2-[4'-(perfluorophenyl)phenyl]pyridinato-N,C 2'}iridium(III)acetylacetonate (abbreviation: [Ir(p-PF-ph)2(acac)]) and bis(2-phenylbenzothiazolato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(bt)2(acac)]); and rare earth metal complexes, such as Tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [Tb(acac)3(Phen)]).

[0103] Examples of phosphorescent materials that emit yellow or red light and whose emission spectrum has a peak wavelength greater than or equal to 570 nm and less than or equal to 750 nm include the following substances.

[0104] For example, organometallic complexes with a pyrimidine backbone, such as (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridium(III) (abbreviation: [Ir(5mdppm)2(dpm)]) and (dipivaloylmethanato)bis[4,6-di(naphthalen-1-yl)pyrimidinato]iridium(III) (abbreviation: [Ir(d1npm)2(dpm)]); organometallic complexes with a pyrazine backbone, such as... B. (Acetylacetonato)bis(2,3,5-triphenylpyrazinato)iridium(III) (abbreviation: [Ir(tppr)2(acac)]), Bis(2,3,5-triphenylpyrazinato)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir(tppr)2(dpm)]), Bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ 2 O,O')iridium(III) (Abbreviation: [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-heptanedionato- 2O, O')iridium(III) (abbreviation: [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) (abbreviation: [Ir(dpq)2(acac)]) and (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]); organometallic complexes with a pyridine skeleton, such as Tris(1-phenylisoquinolinato-N,C 2' )iridium(III) (abbreviation: [Ir(piq)3]), Bis(1-phenylisoquinolinato-N,C 2' )iridium(III)acetylacetonate (abbreviation: [Ir(piq)2acac]) and bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2O,O')iridium(III); platinum complexes, such as 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatin(II) (abbreviation: [PtOEP]); and rare earth metal complexes, such as Tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: [Eu(DBM)3(Phen)]) and Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: [Eu(TTA)3(Phen)]).

[0105] The organic compounds (host material and auxiliary material) used in the light-emitting layers (113, 113a, 113b, and 113c) are one or more types of substances with a larger energy gap than the light-emitting substance (the guest material). In cases where a variety of organic compounds are used for the light-emitting layers (113, 113a, 113b, and 113c), compounds forming an exciplex are preferably used in combination with a phosphorescent light-emitting substance. In such a structure, light emission can be achieved through exciplex-triplet energy transfer (ExTET), which is the energy transfer from an exciplex to a light-emitting substance.In this case, although any of the various organic compounds can be used in a suitable combination to efficiently form an exciplex, the combination of a compound that readily accepts holes (a hole transport material) and a compound that readily accepts electrons (an electron transport material) is particularly preferred. The organic compound of an embodiment of the present invention has a low LUMO level and is therefore suitable for the compound that readily accepts electrons.

[0106] If the light-emitting substance is a fluorescent material, an organic compound is preferably used as the host material, exhibiting a high energy level in a singlet excitation state and a low energy level in a triplet excitation state. For example, an anthracene derivative or a tetracene derivative is preferably used. Specific examples of these include 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9-anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-Phenyl-10-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: FLPPA), 5,12-Diphenyltetracene and 5,12-Bis(biphenyl-2-yl)tetracene.

[0107] In cases where the light-emitting substance is a phosphorescent material, an organic compound with a triplet excitation energy (energy difference between a ground state and a triplet excitation state) higher than that of the light-emitting substance is preferably selected as the host material. In this case, it is possible to use a zinc- or aluminum-based metal complex, an oxadiazole derivative, a triazole derivative, a benzimidazole derivative, a quinoxaline derivative, a dibenzoquinoxaline derivative, a dibenzothiophene derivative, a dibenzofuran derivative, a pyrimidine derivative, a triazine derivative, a pyridine derivative, a bipyridine derivative, a phenanthroline derivative, an aromatic amine, a carbazole derivative, and the like.

[0108] In particular, any of the following hole transport materials and electron transport materials can be used as host materials.

[0109] Examples of host materials with high hole transport properties include aromatic amine compounds, such as N,N'-Di(p-tolyl)-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), N,N'-Bis{4-[bis(3-methylphenyl)amino]phenyl}-N,N'-diphenyl-(1, 1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD) and 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B).

[0110] Carbazole derivatives, such as 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) is also given. Further examples of the carbazole derivative 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.

[0111] Examples of host materials with high hole transport properties include aromatic amine compounds, such as... B. 4,4'-Bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4',4''-Tris(carbazol-9-yl)triphenylamine (abbreviation: TCTA), 4,4',4''-Tris[N-(1-naphthyl)-N-phenylamino]triphenylamine (abbreviation: 1-TNATA), 4,4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: m-MTDATA), 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-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-Diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-Naphthyl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB) 4-Phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA1BP), N,N'-Bis(9-phenylcarbazol-3-yl)-N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N''-Triphenyl-N,N',N''-tris(9-phenylcarbazol-3-yl)benzene-1,3,5-triamine (abbreviation: PCA3B), N-(4-Biphenyl)-N-(9,9-Dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N-(1,1'-Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 9,9-Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluoren-2-amine (abbreviation: PCBAF), N-Phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluoren-2-amine (abbreviation: PCBASF), 2-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation: DPA2SF), N-[4-(9H-carbazol-9-yl)phenyl]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP) and N,N'-Bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethylfluorene-2,7-diamine (abbreviation: YGA2F). Other examples include carbazole compounds, thiophene compounds, furan compounds, fluorene compounds, triphenylene compounds, phenanthrene compounds, and the like, such as 3-[4-(1-naphthyl)phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPN), 3-[4-(9-phenanthryl)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-triyl)tri(dibenzofuran) (abbreviation: DBF3P-II), 1,3,5-tri(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) and 4-[3-(Triphenylen-2-yl)phenyl]dibenzothiophene (abbreviation: mDBPTp-II).,

[0112] Examples of host materials with high electron transport properties include a metal complex with a quinoline or benzoquinoline framework, such as tris(8-quinolinolato)aluminium(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminium(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]-quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(III) (abbreviation: BAlq), or bis(8-quinolinolato)zinc(II) (abbreviation: Znq). Alternatively, a metal complex with an oxazole-based or thiazole-based ligand, such as... B. Bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO) or bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ). Besides such metal complexes, any of the following can be used: 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-oxadiazol-2-yl]benzene (abbreviation: OXD-7) and 9-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11); a triazole derivative, such as 3-(4-Biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ); a compound with an imidazole skeleton (especially a benzimidazole derivative), such as... B. 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI) or 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II); a compound with an oxazole skeleton (especially a benzoxazole derivative), such as 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOS); a phenanthroline derivative, such as bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP) and 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen); heterocyclic compounds with a diazine skeleton, such as...B. 2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-Carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-Diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), 6-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II), 4,6-Bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-Bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and 4,6-Bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm); heterocyclic compounds with a triazine skeleton, such as... B. 2-{4-[3-(N-Phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn); and heterocyclic compounds with a pyridine skeleton, such as3,5-Bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPPy) and 1,3,5-Tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyPB). Alternatively, a high-molecular-weight compound such as poly(2,5-pyridindiyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can be used.

[0113] Furthermore, polycyclic aromatic compounds condensed for the host material, such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives and dibenzo[g,p]chrysene derivatives, can be used. In particular, 9,10-diphenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 6,12-Dimethoxy-5,11-diphenylchrysene,N,N,N',N',N',N'',N'',N'''',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), 9-[4-(10-Phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-Di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-Bianthryl (abbreviation: BANT), 9,9'-(Stilben-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(Stilben-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 1,3,5-Tri(1-pyrenyl)benzene (abbreviation: TPB3) or the like may be used.

[0114] In the case where a variety of organic compounds are used for the light-emitting layers (113, 113a, 113b, and 113c), two compounds forming an exciplex (a first compound and a second compound) can be used in combination with a metal-organic complex. In this case, although any of the various organic compounds can be used in a suitable combination to efficiently form an exciplex, the combination of a compound that readily accepts holes (a hole transport material) and a compound that readily accepts electrons (an electron transport material) is particularly preferred. In particular, any of the materials described in this embodiment can be used as the hole transport material and electron transport material.

[0115] The TADF material is a material capable of upconverting a triplet excitation state to a singlet excitation state (i.e., enabling reverse intersystem crossing) using low thermal energy and efficiently emitting light (fluorescence) from the singlet excitation state. TADF is efficiently maintained under the condition that the energy difference between the triplet excitation level and the singlet excitation level is greater than or equal to 0 eV and less than or equal to 0.2 eV, preferably greater than or equal to 0 eV and less than or equal to 0.1 eV. It should be noted that the "delayed fluorescence" emitted by the TADF material refers to light emission that has the same spectrum as normal fluorescence and a very long lifetime. The lifetime is 10 -6 seconds or longer, preferably 10 -3 Seconds or longer.

[0116] Examples of TADF material include fullerene, a derivative thereof, an acridine derivative such as proflavin, and eosin. Other examples include a metal-containing porphyrin, such as porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (Pd). Examples of metal-containing porphyrins include a protoporphyrin tin fluoride complex (abbreviation: SnF2(Proto IX)), a mesoporphyrin tin fluoride complex (abbreviation: SnF2(Meso IX)), a hematoporphyrin tin fluoride complex (abbreviation: SnF2(Hämato IX)), a coproporphyrin tetramethyl ester tin fluoride complex (abbreviation: SnF2(Copro III-4Me)), an octaethylporphyrin tin fluoride complex (abbreviation: SnF2(OEP)), an etioporphyrin tin fluoride complex (abbreviation: SnF2(Etio I)) and an octaethylporphyrin platinum chloride complex (abbreviation: PtCl2OEP).

[0117] Alternatively, a heterocyclic compound with a π-electron-rich heteroaromatic ring and a π-electron-poor heteroaromatic ring, such as... B. 2-(Biphenyl-4-yl)-4,6-bis(12-phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5-diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-Dimethyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), Bis[4-(9,9-dimethyl-9,10-dihydroacridin)phenyl]sulfone (abbreviation: DMAC-DPS) or 10-Phenyl-10H, 10'H-spiro[acridin-9,9'-anthracene]-10'-one (abbreviation: ACRSA) are used.It should be noted that a substance in which the π-electron-rich heteroaromatic ring is directly bonded to the π-electron-poor heteroaromatic ring is particularly preferred, since both the donor property of the π-electron-rich heteroaromatic ring and the acceptor property of the π-electron-poor heteroaromatic ring are increased, and the energy difference between the singlet excitation state and the triplet excitation state becomes small.

[0118] It should be noted that if a TADF material is used, the TADF material can be used in combination with another organic compound.

[0119] The light-emitting element in Fig. 1. An electron transport layer (114, 114a) is formed over the light-emitting layer (113, 113a) of the EL layer (103, 103a) by a vacuum evaporation process. It should be noted that in the Fig. 1(D) light-emitting element with a tandem structure, an electron transport layer 114b is formed after the formation of the EL layer 103a and the charge generation layer 104 by a vacuum evaporation process also over the light-emitting layer 113b of the EL layer 103b. <elektronentransportschicht>

[0120] The electron transport layers (114, 114a, and 114b) transport the electrons injected from the second electrode 102 through the electron injection layers (115, 115a, and 115b) to the light-emitting layers (113, 113a, and 113b). It should be noted that the electron transport layers (114, 114a, and 114b) each contain an electron transport material. The electron transport materials contained in the electron transport layers (114, 114a, and 114b) are preferably substances with an electron mobility of 1 × 10⁻⁶ or higher. -6 cm 2 / Vs. It should be noted that other substances can also be used, as long as the substances have an electron transport property that is higher than a hole transport property.

[0121] Examples of electron transport materials include metal complexes with a quinoline ligand, a benzoquinoline ligand, an oxazole ligand, and a thiazole ligand; an oxadiazole derivative; a triazole derivative; a phenanthroline derivative; a pyridine derivative; and a bipyridine derivative. Additionally, a π-electron-deficient heteroaromatic compound, such as a nitrogen-containing heteroaromatic compound, can also be used.

[0122] In particular, metal complexes such as Alq3, Tris(4-methyl-8-quinolinolato)aluminium (abbreviation: Almq3), Bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Bis[2-(2-hydroxyphenyl)benzoxazolato]zinc(II) (abbreviation: Zn(BOX)2) and Bis[2-(2-hydroxyphenyl)benzothiazolato]zinc (abbreviation: Zn(BTZ)2), heteroaromatic compounds, such as... B. 2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), OXD-7, 3-(4'-tert-Butylphenyl)-4-phenyl-5-(4''-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-Butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: Bphen), bathocuproine (abbreviation: BCP) and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOS), and quinoxaline derivatives and dibenzoquinoxaline derivatives, such as2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[4-(3,6-Diphenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II).

[0123] As another alternative, a high molecular weight compound such as poly(2,5-pyridindiyl) (abbreviation: PPy), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) can be used.

[0124] Each of the electron transport layers (114, 114a and 114b) is not limited to a single layer and can be a layer arrangement of two or more layers, each containing any one of the aforementioned substances.

[0125] The light-emitting element in Fig. 1. An electron injection layer (115, 115a) is formed over the electron transport layer (114, 114a) of the EL layer (103, 103a) by a vacuum evaporation process. It should be noted that in the case of the Fig. 1(D) of the light-emitting element with a tandem structure, an electron injection layer 115b is formed after the formation of the EL layer 103a and the charge generation layer 104 by a vacuum evaporation process also over the electron transport layer 114b of the EL layer 103b. < Electron injection layer>

[0126] The electron injection layers (115, 115a and 115b) each contain a substance with high electron injection properties. The electron injection layers (115, 115a and 115b) can each be made using an alkali metal, an alkaline earth metal or a compound thereof, such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF₂) or lithium oxide (LiO₂). x ). A rare-earth metal compound such as erbium fluoride (ErF3) can also be used. An electride can also be used for the electron injection layers (115, 115a, and 115b). Examples of the electride include a substance in which electrons are added to calcium oxide-aluminum oxide at a high concentration. Any of the substances mentioned above that are used for the electron transport layers (114, 114a, and 114b) can also be used.

[0127] A composite material in which an organic compound and an electron donor (donor) are mixed can also be used for the electron injection layers (115, 115a, and 115b). Such a composite material exhibits excellent electron injection and electron transport properties, since electrons are generated in the organic compound by the electron donor. Here, the organic compound is preferably a material that can transport the generated electrons excellently. In particular, for example, the electron transport materials mentioned above (e.g., a metal complex or a heteroaromatic compound) can be used to form the electron transport layers (114, 114a, and 114b). A substance that has an electron-donating property with respect to the organic compound can be used as the electron donor.Preferred examples are an alkali metal, an alkaline earth metal, and a rare earth metal. Specifically, lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like may be specified. Furthermore, an alkali metal oxide and an alkaline earth metal oxide are preferred, and lithium oxide, calcium oxide, barium oxide, and the like may be specified. Alternatively, a Lewis base, such as magnesium oxide, may be used. As a further alternative, an organic compound, such as tetrathiafulvalene (abbreviation: TTF), may be used.

[0128] In the case where light received from the light-emitting layer 113b is amplified, the optical path length between the second electrode 102 and the light-emitting layer 113b is preferably less than one-quarter of the wavelength λ of light emitted by the light-emitting layer 113b. In this case, the optical path length can be adjusted by changing the thickness of the electron transport layer 114b or the electron injection layer 115b. <ladungserzeugungsschicht>

[0129] The charge-generating layer 104 has a function for injecting electrons into the EL layer 103a and for injecting holes into the EL layer 103b when a voltage is applied between the first electrode (anode) 101 and the second electrode (cathode) 102. The charge-generating layer 104 can have either a structure in which an electron acceptor is added to a hole transport material or a structure in which an electron donor is added to an electron transport material. Alternatively, both of these structures can be stacked on top of each other. It should be noted that forming the charge-generating layer 104 using any of the aforementioned materials can suppress an increase in the operating voltage during the layering of the EL layers.

[0130] In the case where the charge-generating layer 104 has a structure in which an electron acceptor is added to a hole-transporting material, any of the materials described for this embodiment can be used as the hole-transporting material. 7,7,8,8-Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, and the like can be used as electron acceptors. Oxides of metals belonging to groups 4 to 8 of the periodic table can also be specified. In particular, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, rhenium oxide, or the like are used.

[0131] In the case where the charge-generating layer 104 has a structure in which an electron donor is added to an electron transport material, any of the materials described for this embodiment can be used as the electron transport material. It is possible to use an alkali metal, an alkaline earth metal, a rare earth metal, metals belonging to groups 2 and 13 of the periodic table, or an oxide or carbonate thereof as the electron donor. In particular, lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), ytterbium (Yb), indium (In), lithium oxide, cesium carbonate, or the like are preferably used. Alternatively, an organic compound, such as tetrathianaphthacene, can be used as the electron donor.

[0132] It should be noted that the EL layer 103c in Fig. 1(E) has a structure similar to those of the EL layers (103, 103a and 103b) described above. Furthermore, the charge-generating layers 104a and 104b each have a structure similar to that of the charge-generating layer 104 described above. <substrat>

[0133] The light-emitting element described in this embodiment can be formed on any of several different substrates. It should be noted that the type of substrate is not limited to any one particular type. Examples of substrates include a semiconductor substrate (e.g., a single-crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate containing a stainless steel foil, a tungsten substrate, a substrate containing a tungsten foil, a flexible substrate, a mounting film, paper containing a fiber material, and a base material film.

[0134] Examples of the glass substrate include a barium borosilicate glass substrate, an aluminum borosilicate glass substrate, and a soda-lime glass substrate. Examples of the flexible substrate, the affixing film, and the base material film include plastics, typically polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES); a synthetic resin, such as acrylic resin; polypropylene; polyester; polyvinyl fluoride; polyvinyl chloride; polyamide; polyimide; aramid; epoxy; an evaporation-formed inorganic film; and paper.

[0135] For the fabrication of the light-emitting element in this embodiment, a vacuum process, such as an evaporation process, or a solution process, such as a rotational coating process or an inkjet process, can be used. If an evaporation process is used, a physical vapor deposition (PVD) process, such as a sputtering process, an ion plating process, an ion beam evaporation process, a molecular beam evaporation process, or a vacuum evaporation process, a chemical vapor deposition (CVD) process, or the like, can be employed.In particular, the functional layers (the hole injection layers (111, 111a and 111b), the hole transport layers (112, 112a and 112b), the light-emitting layers (113, 113a, 113b and 113c), the electron transport layers (114, 114a and 114b), the electron injection layers (115, 115a and 115b) and the charge generation layers (104, 104a and 104b)) contained in the EL layers, of the light-emitting element can be produced by an evaporation process (e.g. a vacuum evaporation process), a coating process (e.g. a dip coating process, a nozzle coating process, a rod coating process, a rotary coating process or a spray coating process), a printing process (e.g. an inkjet process, a screen printing (stencil printing), an offset printing process) (flat printing), flexographic printing (relief printing), gravure printing or microcontact printing) or the like.

[0136] It should be noted that materials that can be used for the functional layers (the hole injection layers (111, 111a and 111b), the hole transport layers (112, 112a and 112b), the light-emitting layers (113, 113a, 113b and 113c), the electron transport layers (114, 114a and 114b), the electron injection layers (115, 115a and 115b) and the charge generation layers (104, 104a and 104b)) contained in the EL layers (103, 103a and 103b) in the light-emitting element described in this embodiment are not limited to the materials listed above, and that other materials can be used in combination as long as the functions of the layers are fulfilled. For example, a high-molecular-weight compound (e.g.an oligomer, a dendrimer, or a polymer), a medium-molecular-weight compound (a compound between a low-molecular-weight compound and a high-molecular-weight compound with a molecular weight of 400 to 4000), an inorganic compound (e.g., a quantum dot material), or the like. The quantum dot can be a gelatinous quantum dot, an alloyed quantum dot, a core-shell quantum dot, a core-quantum quantum dot, or the like.

[0137] The structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 3)

[0138] This embodiment describes a light-emitting device of an embodiment of the present invention. It should be noted that a Fig. The light-emitting device shown in Figure 2(A) is a light-emitting active-matrix device in which transistors (FETs) 202 are electrically connected to light-emitting elements (203R, 203G, 203B, and 203W) over a first substrate 201. The light-emitting elements (203R, 203G, 203B, and 203W) include a common EL layer 204 and each has a microcavity structure in which the optical path length between electrodes is adapted according to the emission color of the light-emitting element. The light-emitting device is a top-emission light-emitting device in which light is emitted from the EL layer 204 through color filters (206R, 206G, and 206B) formed over a second substrate 205.

[0139] The in Fig. The light-emitting device shown in Figure 2(A) is manufactured such that a first electrode 207 serves as a reflective electrode and a second electrode 208 serves as a transflective electrode. It should be noted that, with regard to electrode materials for the first electrode 207 and the second electrode 208, reference may be made, if necessary, to the description in any of the other embodiments.

[0140] In the case where, for example, Fig. 2(A) where the light-emitting element 203R serves as a red light-emitting element, the light-emitting element 203G serves as a green light-emitting element, the light-emitting element 203B serves as a blue light-emitting element, and the light-emitting element 203W serves as a white light-emitting element, is, as in Fig. Figure 2(B) shows that a distance between the first electrode 207 and the second electrode 208 of the light-emitting element 203R is adjusted to obtain an optical path length of 200R, a distance between the first electrode 207 and the second electrode 208 of the light-emitting element 203G is adjusted to obtain an optical path length of 200G, and a distance between the first electrode 207 and the second electrode 208 of the light-emitting element 203B is adjusted to obtain an optical path length of 200B. It should be noted that the optical adjustment can be carried out in such a way that, as shown in Fig. Figure 2(B) shows a conductive layer 210R arranged above the first electrode 207 at the light-emitting element 203R and a conductive layer 210G arranged above the first electrode 207 at the light-emitting element 203G.

[0141] The second substrate 205 is provided with the color filters (206R, 206G, and 206B). It should be noted that each color filter transmits visible light in a specific wavelength range and blocks visible light in a specific wavelength range. Therefore, as shown in Fig. Figure 2(A) shows the color filter 206R, which transmits only light in the red wavelength range, positioned at an overlap with the light-emitting element 203R, thus enabling red light emission from the light-emitting element 203R. Furthermore, the color filter 206G, which transmits only light in the green wavelength range, is positioned at an overlap with the light-emitting element 203G, thus enabling green light emission from the light-emitting element 203G. Additionally, the color filter 206B, which transmits only light in the blue wavelength range, is positioned at an overlap with the light-emitting element 203B, thus enabling blue light emission from the light-emitting element 203B. It should be noted that the light-emitting element 203W can emit white light without a color filter.It should be noted that a black layer (black matrix) 209 may be provided at one end position of each color filter. The color filters (206R, 206G and 206B) and the black layer 209 may be covered with a covering layer formed using a transparent material.

[0142] Although the light-emitting device in Fig. 2(A) has a structure in which light is extracted from the side of the second substrate 205 (top-emission structure), as shown in Fig. Figure 2(C) shows a structure in which light is extracted from the side of the first substrate 201, above which the FETs 202 are formed (bottom-emission structure). In the case of a light-emitting bottom-emission device, the first electrode 207 is configured as a transflective electrode and the second electrode 208 is configured as a reflective electrode. The first substrate 201 is a substrate that has at least one light-transmitting property. As shown in Fig. As shown in Figure 2(C), color filters (206R', 206G' and 206B') are provided such that they are closer to the first substrate 201 than the light-emitting elements (203R, 203G and 203B).

[0143] In Fig. 2(A) The light-emitting elements are the red light-emitting element, the green light-emitting element, the blue light-emitting element, and the white light-emitting element; however, the light-emitting elements of an embodiment of the present invention are not limited to these, and a yellow light-emitting element or an orange light-emitting element may be used. It should be noted that with regard to the materials used for the EL layers (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), reference may be made, as needed, to the description in any of the other embodiments in order to fabricate each of the light-emitting elements.In this case, it is necessary to select a suitable color filter depending on the emission color of the light-emitting element.

[0144] The above structure can be used to manufacture a light-emitting device that includes light-emitting elements exhibiting a variety of emission colors.

[0145] It should be noted that the structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 4)

[0146] This embodiment describes a light-emitting device of an embodiment of the present invention.

[0147] The use of the element structure of the light-emitting element in one embodiment of the present invention enables the fabrication of a light-emitting active-matrix device or a light-emitting passive-matrix device. It should be noted that a light-emitting active-matrix device has a structure comprising a combination of a light-emitting element and a transistor (FET). Therefore, both a light-emitting passive-matrix device and a light-emitting active-matrix device are each embodiments of the present invention. It should be noted that any of the light-emitting elements described in the other embodiments can be used for the light-emitting device described in this embodiment.

[0148] In this embodiment, a light-emitting active matrix device is used based on Fig. 3 described.

[0149] Fig. 3(A) is a top view showing the light-emitting device 21, and Fig. 3(B) is a cross-sectional view extending along the catenary AA' in Fig. 3(A). The light-emitting active matrix device comprises a pixel section 302, a driver circuit section (a source line driver circuit) 303, and driver circuit sections (gate line driver circuits) (304a and 304b) provided above a first substrate 301. The pixel section 302 and the driver circuit sections (303, 304a, and 304b) are sealed with a sealant 305 between the first substrate 301 and a second substrate 306.

[0150] A connecting line 307 is provided above the first substrate 301. The connecting line 307 is electrically connected to an FPC 308, which is an external input terminal. It should be noted that the FPC 308 transmits a signal (e.g., a video signal, a clock signal, a start signal, or a reset signal) or a potential from outside to the driver circuit sections (303, 304a, and 304b). The FPC 308 may be provided with a printed circuit board (PWB). It should be noted that the light-emitting device provided with an FPC or a PWB is included in the category of a light-emitting device.

[0151] Fig. Figure 3(B) represents a cross-sectional structure of the light-emitting device.

[0152] Pixel section 302 contains a plurality of pixels, each containing a switching FET 311, a current-controlling FET 312, and a first electrode 313 electrically connected to FET 312. It should be noted that the number of FETs contained in each pixel is not particularly limited and can be adjusted as appropriate.

[0153] For example, FETs 309, 310, 311, and 312 can be used as staggered transistors or inverted staggered transistors without any particular restrictions. A top-gate transistor, a bottom-gate transistor, or the like can be used.

[0154] It should be noted that there is no particular restriction regarding the crystallinity of a semiconductor that can be used for FETs 309, 310, 311, and 312, and an amorphous semiconductor or a semiconductor with crystallinity (a microcrystalline semiconductor, a polycrystalline semiconductor, a single-crystal semiconductor, or a semiconductor that partially comprises crystalline regions) can be used. Preferably, a semiconductor with crystallinity is used, in which case a deterioration of the transistor characteristics can be suppressed.

[0155] The semiconductor can be, for example, an element from group 14, a compound semiconductor, an oxide semiconductor, an organic semiconductor, or the like. Typical examples include a semiconductor containing silicon, a semiconductor containing gallium arsenide, or an oxide semiconductor containing indium.

[0156] The driver circuit section 303 includes the FET 309 and the FET 310. It should be noted that the driver circuit section 303 can be implemented with a circuit containing transistors of the same conduction type (either n-channel or p-channel transistors), or with a CMOS circuit containing one n-channel transistor and one p-channel transistor. Furthermore, a driver circuit can be provided externally.

[0157] An end section of the first electrode 313 is covered with an insulator 314. The insulator 314 can be formed using an organic compound, such as a negative photosensitive resin or a positive photosensitive resin (acrylic resin), or an inorganic compound, such as silicon dioxide, silicon oxynitride, or silicon nitride. The insulator 314 preferably has a curved surface with a curvature at its upper end section or lower end section. In this case, an advantageous covering can be obtained with a film formed over the insulator 314.

[0158] An EL layer 315 and a second electrode 316 are arranged above 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.

[0159] The structure and materials described in any of the other embodiments can be used for the components of a light-emitting element 317 described in this embodiment. Although not shown here, the second electrode 316 is electrically connected to the FPC 308, which is an external input terminal.

[0160] Although the cross-sectional view in Fig. Where 3(B) represents only one light-emitting element 317, a plurality of light-emitting elements are arranged in a matrix in pixel section 302. Light-emitting elements emitting light of three types of colors (R, G, and B) are selectively formed in pixel section 302, thereby obtaining a light-emitting device capable of displaying a full-color image. In addition to the light-emitting elements emitting light of three types of colors (R, G, and B), light-emitting elements emitting light of white (W), yellow (Y), magenta (M), cyan (C), and the like can be formed, for example. For instance, the light-emitting elements emitting light of some of the aforementioned colors are used in combination with the light-emitting elements emitting light of three types of colors (R, G, and B), thereby producing effects such as…An improvement in color purity and a reduction in power consumption can be achieved. Alternatively, a light-emitting device capable of displaying a full-color image can be produced by combining it with color filters. Red (R), green (G), blue (B), cyan (C), magenta (M), and yellow (Y) color filters, and the like, can be used as color filters.

[0161] When the second substrate 306 and the first substrate 301 are joined together with the sealant 305, the FETs (309, 310, 311, and 312) and the light-emitting element 317 are positioned above the first substrate 301 in a space 318 enclosed by the first substrate 301, the second substrate 306, and the sealant 305. It should be noted that the space 318 can be filled with an inert gas (such as nitrogen or argon) or an organic substance (including the sealant 305).

[0162] For the sealant 305, an epoxy-based resin, a glass frit, or the like can be used. Preferably, a material with minimal moisture and oxygen permeability is used for the sealant 305. The second substrate 306 can be a substrate that can be used as the first substrate 301, in a similar manner. Therefore, any of the various substrates described in the other embodiments can be used appropriately. The substrate can be a glass substrate, a quartz substrate, or a plastic substrate made of fiber-reinforced plastic (FRP), polyvinyl fluoride (PVF), polyester, acrylic resin, or the like. In the case where a glass frit is used for the sealant, the first substrate 301 and the second substrate 306 are preferably glass substrates with respect to adhesion.

[0163] Therefore, the light-emitting active matrix device can be obtained.

[0164] In the case where the light-emitting active matrix device is deployed over a flexible substrate, the FETs and the light-emitting element can be formed directly over the flexible substrate. Alternatively, the FETs and the light-emitting element can be formed over a substrate provided with a separating layer and then separated by applying heat, force, laser light, or the like to the separating layer to transfer them onto a flexible substrate. For the separating layer, for example, a layer arrangement comprising inorganic films, such as a tungsten film and a silicon oxide film, or an organic resin film made of polyimide or the like, can be used.Examples of flexible substrates include, in addition to a substrate on which a transistor can be formed, a paper substrate, a cellophane substrate, an aramid film substrate, a polyimide film substrate, a fabric substrate (including a natural fiber (e.g., silk, cotton, or hemp), a synthetic fiber (e.g., nylon, polyurethane, or polyester), a regenerated fiber (e.g., acetate, cupro, viscose, or regenerated polyester), or the like), a leather substrate, and a rubber substrate. Using any of these substrates can increase durability and heat resistance, and reduce weight and thickness.

[0165] It should be noted that the structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 5)

[0166] In this embodiment, examples of various electronic devices and a vehicle are described that are manufactured using the light-emitting device of an embodiment of the present invention or a display device that includes the light-emitting element of an embodiment of the present invention.

[0167] Electronic devices that are in Fig. 4(A) to 4(F) may include a housing 7000, a display section 7001, a loudspeaker 7003, an LED lamp 7004, operating buttons 7005 (including a power switch or an operating switch), a connection terminal 7006, a sensor 7007 (a sensor with a function for measuring or detecting force, displacement, position, velocity, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electrical power, radiation, flow rate, humidity, gradient, vibration, odor or infrared beam), a microphone 7008 and the like.

[0168] Fig. 4(A) represents a portable computer which, in addition to the above components, may include a switch 7009, an infrared connector 7010 and the like.

[0169] Fig. 4(B) represents a portable image display device (e.g. a DVD player) which is equipped with a storage medium and may, in addition to the components mentioned above, include a second display section 7002, a storage medium read section 7011 and the like.

[0170] Fig. 4(C) represents a spectacle-like display which, in addition to the above components, may include the second display section 7002, a holder 7012, an earphone 7013 and the like.

[0171] Fig. 4(D) represents a digital camera which has a television reception function and may include, in addition to the above components, an antenna 7014, a release button 7015, an image reception section 7016 and the like.

[0172] Fig. 4(E) represents a mobile phone (including a smartphone) which may contain in the housing 7000 the display section 7001, a microphone 7019, a speaker 7003, a camera 7020, an external connection section 7021, an operating button 7022 and the like.

[0173] Fig. 4(F) represents a large television set (also referred to as a TV or television receiver) that may include the housing 7000, the display section 7001, and the like. The housing 7000 is shown here supported by a stand 7018. The television set can be operated with a separate remote control 7111 or the like. The display section 7001 may include a touch sensor. The television set can be operated by touching the display section 7001 with a finger or the like. The remote control 7111 may be equipped with a display section for showing information output by the remote control 7111. The television channels and volume can be controlled, and images displayed on the display section 7001 can be controlled, by means of operating buttons or a touchscreen on the remote control 7111.

[0174] The in Fig. 4(A) to Fig. 4(F) The electronic devices shown may have various functions, such as a function for displaying various information (a still image, a moving image, a text image, and the like) on a display section, a touchscreen function, a function for displaying a calendar, the date, the time, and the like, a function for controlling processing by means of various types of software (programs), a wireless communication function, a function for connecting to various computer networks by means of a wireless communication function, a function for transmitting and receiving various data by means of a wireless communication function, a function for reading a program or data that is / are stored in a storage medium and for displaying the program or data on the display section, and the like.Furthermore, the electronic device, which includes a multitude of display sections, may have a function for displaying image data mainly on one display section while simultaneously displaying text data mainly on another display section, a function for displaying a three-dimensional image by displaying images on a multitude of display sections taking into account parallax or the like.Furthermore, the electronic device, which includes an image reception section, may have a function for capturing a still image, a function for capturing a moving image, a function for automatically or manually correcting a captured image, a function for storing a captured image on a recording medium (an external recording medium or a recording medium built into the camera), a function for displaying a captured image on the display section, or the like. It should be noted that functions intended for the [missing information] are not included. Fig. 4(A) to Fig. 4(F) shown electronic devices can be provided, are not limited to them and the electronic devices may have different functions.

[0175] Fig. 4(G) represents a smartwatch comprising the case 7000, the display section 7001, control buttons 7022 and 7023, a connection port 7024, a band 7025, a buckle 7026 and the like.

[0176] The display section 7001, mounted in the housing 7000 which serves as a frame, comprises a non-rectangular display area. The display section 7001 can display an icon 7027, which shows the time, another icon 7028, and the like. The display section 7001 can be a touchscreen (an input / output device) that includes a touch sensor (an input device).

[0177] The smartwatch, which is in Fig. 4(G) can have various functions, such as a function to display various information (e.g., a still image, a moving image, and a text image) on a display section, a touchscreen function, a function to display a calendar, date, time, and the like, a function to control processing by means of various types of software (programs), a wireless communication function, a function to connect to various computer networks by means of a wireless communication function, a function to transmit and receive various data by means of a wireless communication function, a function to read a program or data that is / are stored in a storage medium and to display the program or data on the display section, and the like.

[0178] The housing 7000 can contain a loudspeaker, a sensor (a sensor with a function to measure or detect force, displacement, position, speed, acceleration, angular velocity, rotational speed, distance, light, liquid, magnetism, temperature, chemical substance, sound, time, hardness, electric field, current, voltage, electrical power, radiation, flow rate, humidity, gradient, vibration, odor or infrared rays), a microphone and the like.

[0179] It should be noted that the light-emitting device of an embodiment of the present invention, or the display device comprising the light-emitting element of an embodiment of the present invention, can be used in the display section of any electronic device described in this embodiment, so that a long-life electronic device can be obtained.

[0180] Another electronic device incorporating the light-emitting device is a foldable portable information terminal, which is located in Fig. 5(A) to Fig. 5(C) is shown. Fig. 5(A) represents a portable information terminal 9310, which is unfolded. Fig. Figure 5(B) depicts the portable information terminal 9310 during unfolding or folding. Fig. Figure 5(C) depicts the 9310 portable information terminal in its folded state. The 9310 portable information terminal is highly portable when folded and, when unfolded, offers excellent searchability due to its large, seamless display area.

[0181] A display section 9311 is supported by three housings 9315 connected to each other by hinges 9313. It should be noted that the display section 9311 can be a touchscreen (an input / output device) that includes a touch sensor (an input device). The portable information terminal 9310 can be reversibly changed in shape from an open state to a folded state by bending the display section 9311 at a connection point between two housings 9315 using the hinges 9313. The light-emitting device of an embodiment of the present invention can be used for the display section 9311. Furthermore, a long-life electronic device can be obtained. A display area 9312 in the display section 9311 is a display area that is positioned on a side surface of the folded portable information terminal 9310.The display area 9312 can show information icons, shortcuts to frequently used applications or programs, and the like, and allows for easy confirmation of information as well as starting applications and the like.

[0182] Fig. 6(A) and Fig. 6(B) constitute a vehicle incorporating the light-emitting device. The light-emitting device may be installed in the vehicle and, in particular, may be located in headlights 5101 (including rear headlights), a wheel cover 5102, part of a door or the whole of a door 5103, or the like, on the outside of the vehicle, which is in Fig. 6(A) shown. The light-emitting device may also be contained in a display section 5104, a steering wheel 5105, a gearshift lever 5106, a seat 5107, an interior rearview mirror 5108, or the like on the inside of the vehicle, which is in Fig. 6(B) is shown, or may be contained in part of a glass window.

[0183] In the manner described above, electronic devices and vehicles can be obtained using the light-emitting device or the display device of an embodiment of the present invention. In this case, a long-life electronic device can be obtained. It should be noted that the light-emitting device or the display device for electronic devices and vehicles can be used in various fields, not limited to those described in this embodiment.

[0184] It should be noted that the structures described in this embodiment can be combined with any of the structures described in the other embodiments as required. (Version 6)

[0185] In this embodiment, a lighting device structure is defined based on Fig. 7 described, which is produced using the light-emitting device of an embodiment of the present invention or the light-emitting element that is part of the light-emitting device.

[0186] Fig. 7(A) and Fig. Figure 7(B) shows examples of cross-sectional views of lighting devices. Fig. 7(A) represents a bottom-emission lighting device in which light is extracted from the side of the substrate, and Fig. 7(B) represents a top-emission lighting device in which light is extracted from the side of the sealing substrate.

[0187] A lighting device 4000, which is in Fig. Figure 7(A) shows a light-emitting element 4002 above a substrate 4001. The illumination device 4000 also includes a substrate 4003 with an unevenness on the outside of the substrate 4001. The light-emitting element 4002 includes a first electrode 4004, an EL layer 4005, and a second electrode 4006.

[0188] The first electrode 4004 is electrically connected to an electrode 4007, and the second electrode 4006 is electrically connected to an electrode 4008. An auxiliary line 4009, electrically connected to the first electrode 4004, can also be provided. It should be noted that an insulating layer 4010 is formed over the auxiliary line 4009.

[0189] The substrate 4001 and a sealing substrate 4011 are joined to each other by a sealing agent 4012. A desiccant 4013 is preferably provided between the sealing substrate 4011 and the light-emitting element 4002. The substrate 4003 has the unevenness described in Fig. 7(A) is shown, which can increase the extraction efficiency of the light emitted by the light-emitting element 4002.

[0190] A lighting device 4200, which is in Fig. Figure 7(B) shows a light-emitting element 4202 above a substrate 4201. The light-emitting element 4202 includes a first electrode 4204, an EL layer 4205 and a second electrode 4206.

[0191] The first electrode 4204 is electrically connected to an electrode 4207, and the second electrode 4206 is electrically connected to an electrode 4208. An auxiliary line 4209, electrically connected to the second electrode 4206, can be provided. An insulating layer 4210 can be provided under the auxiliary line 4209.

[0192] The substrate 4201 and a sealing substrate 4211 with unevenness are bonded to each other with a sealant 4212. A barrier film 4213 and a planarizing film 4214 can be provided between the sealing substrate 4211 and the light-emitting element 4202. The sealing substrate 4211 has the unevenness that is described in Fig. 7(B) is shown, which can increase the extraction efficiency of the light emitted by the light-emitting element 4202.

[0193] Examples of such lighting devices include ceiling lights for interior lighting. Examples of ceiling lights include directly mounted lights and recessed lights. Such lighting devices are manufactured using a combination of the light-emitting device and a housing or cover.

[0194] Another example: Such lighting devices can be used for floor lighting, illuminating a floor and thus improving floor safety. Floor lighting can be effectively used, for example, in a bedroom, on stairs, or in a hallway. In this case, the size or shape of the floor lighting can be adapted to the area or structure of a room. The floor lighting can be a stationary lighting device, manufactured using a combination of the light-emitting device and a support.

[0195] Such lighting devices can also be used for a leaf-shaped lighting fixture (leaf-shaped lighting). The leaf-shaped lighting, which is mounted on a wall, is space-saving and can therefore be used for a wide variety of purposes. Furthermore, the surface area of ​​the leaf-shaped lighting can be easily enlarged. The leaf-shaped lighting can also be used on a wall or housing with a curved surface.

[0196] In addition to the above examples, if the light-emitting device of an embodiment of the present invention, or the light-emitting element that is part of the light-emitting device, is used as part of a piece of furniture in a room, a lighting device that serves as that piece of furniture can be obtained.

[0197] As described above, various lighting devices incorporating the light-emitting device can be obtained. It should be noted that these lighting devices are also embodiments of the present invention.

[0198] It should be noted that the structures described in this embodiment can be used in combination with one of the structures described in the other embodiments, as required. [Example 1]<<Synthesebeispiel 1> >

[0199] This synthesis example describes a method for synthesizing 4,8-bis[3-(9,9-dimethylfluoren-2-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mFP2Bfpm), which is the organic compound of an embodiment of the present invention, represented by the structural formula (100) of embodiment 1. The structure of 4,8mFP2Bfpm is shown below. [Chemical Formula 21]<Synthese von 4,8mFP2Bfpm>

[0200] First, 1.0 g of 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine, 3.8 g of 3-(dimethylfluoren-2-yl)phenylpinacolboron, 6.1 g of potassium phosphate, 100 ml of diglyme, and 2.1 g of tert-butanol were placed in a flask. The air in the flask was replaced with nitrogen. 37 mg of palladium(II) acetate and 0.20 mg of di(1-adamantyl)-n-butylphosphine were added, and the mixture was heated under a nitrogen stream at 120 °C for 13 hours. Water and toluene were added to the resulting reaction mixture, and then the mixture was filtered. The organic layer separated from the filtrate was washed with a saturated salt solution, magnesium sulfate was added, and the mixture was filtered. After the filtrate was dried, it was recrystallized from toluene to yield 1.6 g of a pale yellow target solid in 55% yield. A synthesis scheme is shown below in formula (a-1).

[0201] A train sublimation process was used to purify 1.6 g of the pale yellow solid by sublimation. During sublimation purification, the solid was heated at 310 °C under a pressure of 2.6 Pa with an argon gas flow rate of 5 ml / min. After sublimation purification, 1.5 g of a yellow target solid were obtained in 94% yield.

[0202] Analysis results through nuclear magnetic resonance ( 1 The 1H NMR spectroscopy of the obtained yellow solid is shown below. 1 H-NMR diagram is shown in Fig. Figure 8 shows that these results reveal that 4.8mFP2Bfpm, which is the organic compound represented by structural formula (100), was obtained in this example.

[0203] 1 H NMR. δ (TCE-d2):1.61(d,12H), 7.33-7.38(m,4H), 7.46-7.49(t,2H), 7.60-7.63(t,1H), 7.69-7.83(m,10), 7.86-7.89(t,2H), 7.90-7.92(d,1H), 8.01(s,1H), 8.09(d,1H), 8.64(d,2H), 8.94(s,1H), 9.35(s,1H).

[0204] Fig. Figure 9(A) shows a UV-VIS absorption spectrum (hereinafter referred to simply as the "absorption spectrum") and an emission spectrum of 4.8 mFP2 Bfpm in a toluene solution. The horizontal axis represents the wavelength, and the vertical axes represent the absorption intensity and the emission intensity.

[0205] The absorption spectrum was measured using a UV-VIS spectrophotometer (V550, manufactured by JASCO Corporation). To calculate the absorption spectrum of 4.8 mFP2 Bfpm in a toluene solution, the absorption spectrum of toluene placed in a quartz cell was measured and then subtracted from the absorption spectrum of a 4.8 mFP2 Bfpm toluene solution placed in a quartz cell. The emission spectrum was measured using a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). The emission spectrum of 4.8 mFP2 Bfpm in the toluene solution was measured by placing the 4.8 mFP2 Bfpm toluene solution in a quartz cell.

[0206] Fig. Figure 9(A) shows that 4.8mFP2Bfpm in the toluene solution has absorption peaks at about 283 nm and 315 nm and an emission wavelength peak at about 401 nm (excitation wavelength: 327 nm).

[0207] Next, the absorption and emission spectra of a 4.8 mFP2 Bfpm solid thin film were measured. The solid thin film was produced by vacuum evaporation over a quartz substrate. The absorption spectrum of the thin film was determined using an absorptivity (-log). 10 [%T / (100-%R)]), which was obtained from the transmittance and reflectance of the thin film containing the substrate, was calculated. Note that %T represents the transmittance and %R represents the reflectance. The absorption spectrum was measured using a UV-VIS spectrophotometer (U-4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured using a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). The obtained absorption and emission spectra of the solid thin film are presented in Fig. Figure 9(B) shows the horizontal axis representing the wavelength and the vertical axes representing the absorption intensity and the emission intensity.

[0208] The result in Fig. Figure 9(B) shows that the solid thin film of 4.8mFP2Bfpm has absorption peaks at about 213 nm, 282 nm and 316 nm and an emission wavelength peak at about 422 nm (excitation wavelength: 322 nm). [Example 2]

[0209] This example describes the elemental structures, manufacturing processes, and properties of a light-emitting element 1 (a light-emitting element of an embodiment of the present invention), in which 4,8-bis[3-(9,9-dimethylfluoren-2-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4.8mFP2Bfpm) (structural formula (100)), as described in Example 1, is used in a light-emitting layer, and of a light-emitting reference element 2, in which 4,6-bis[3-(9,9-dimethylfluoren-2-yl)phenyl]pyrimidine (abbreviation: 4.6mFP2Pm) is used in a light-emitting layer. It should be noted that Fig. Figure 10 represents the elemental structure of a light-emitting element used in this example, and Table 1 shows specific structures. Chemical formulas of materials used in this example are shown below. [Table 1] ersteElektrode Lochinjektionsschicht Lochtransportschicht LichtemittierendeSchicht Elektronentransportschicht Elektroneninjektionsschicht zweiteElektrode LichtemittierendesElement 1 ITSO(70 nm) DBT3P-II:MoOx(2:1 50 nm) PCBBi1BP(20 nm) * 4,8mFP2Bfpm(20 nm) Bphen(15 nm) LiF(1 nm) Al(200 nm) LichtemittierendesVergleichselement 2 ITSO(70 nm) DBT3P-II:MoOx(2:1 50 nm) PCBBi1BP(20 nm) ** 4,6mFP2Pm(20 nm) Bphen(15 nm) LiF(1 nm) Al(200 nm) * 4,8mFP2Bfpm:PCCP:[Ir(ppy)2(4dppy)] (0,6:0,4:0,1 40 nm) ** 4,6mFP2Pm:PCCP:[Ir(ppy)2(4dppy)] (0,6:0,4:0,1 40 nm) <<Herstellung der Licht emittierenden Elemente> >

[0210] Each of the light-emitting elements described in this example has, as shown in Fig. Figure 10 shows 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 arranged in this order over a first electrode 901 formed over a substrate 900, and a second electrode 903 is arranged over the electron injection layer 915.

[0211] First, the first electrode 901 was formed over the substrate 900. The electrode area was set to 4 mm². 2 (2 mm × 2 mm). A glass substrate was used as substrate 900. The first electrode 901 was formed using indium tin oxide containing silicon oxide (ITSO) by a sputtering process to a thickness of 70 nm.

[0212] As a pretreatment, the substrate surface was washed with water, baked at 200 °C for one hour, and then treated with UV ozone for 370 seconds. Afterwards, the substrate was transferred to a vacuum evaporation unit where the pressure was set to approximately 10 -4 After the Pa was reduced, vacuum baking was carried out at 170 °C for 30 minutes in a heating chamber of the vacuum evaporation device, and then the substrate was cooled for approximately 30 minutes.

[0213] Next, the hole injection layer 911 was formed over the first electrode 901. After the pressure in the vacuum evaporation device was increased to 10 -4 After Pa had been reduced, the hole injection layer 911 was formed by co-evaporation to have a mass ratio of 1,3,5-tri(dibenzothiophen-4-yl)benzene (abbreviation: DBT3P-II) to molybdenum oxide of 2:1 and a thickness of 50 nm.

[0214] Subsequently, the hole transport layer 912 was formed over the hole injection layer 911. The hole transport layer 912 was formed by evaporation of 4,4'-diphenyl-4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi1BP) to a thickness of 20 nm.

[0215] Next, the light-emitting layer 913 was formed above the hole transport layer 912.

[0216] The light-emitting layer 913 of light-emitting element 1 was deposited by co-evaporation of 4.8 mFP2Bfpm (100) as host material, PCCP as auxiliary material, and [Ir(ppy)2(4dppy)] as guest material (phosphorescent light-emitting material) to achieve a weight ratio of 4.8 mFP2Bfpm:PCCP:[Ir(ppy)2(4dppy)] = 0.6:0.4:0.1. The thickness was set to 40 nm.

[0217] The light-emitting layer 913 in the light-emitting reference element 2 was deposited by co-evaporation of 4.6 mFP2Pm (200) as the host material, PCCP as the auxiliary material, and [Ir(ppy)2(4dppy)] as the guest material (phosphorescent light-emitting material) to achieve a weight ratio of 4.6 mFP2Pm:PCCP:[Ir(ppy)2(4dppy)] = 0.6:0.4:0.1. The thickness was set to 40 nm.

[0218] Next, the electron transport layer 914 was formed over the light-emitting layer 913. The electron transport layer 914 in the light-emitting element 1 was formed as follows: 4.8 mFP2Bfpm and bathophene anthroline (abbreviated Bphen) were sequentially deposited by evaporation to thicknesses of 20 nm and 15 nm, respectively. The electron transport layer 914 in the light-emitting reference element 2 was formed as follows: 4.6 mFP2Pm and Bphen were sequentially deposited by evaporation to thicknesses of 20 nm and 15 nm, respectively.

[0219] Subsequently, the electron injection layer 915 was formed over the electron transport layer 914. The electron injection layer 915 was formed by evaporating lithium fluoride (LiF) to a thickness of 1 nm.

[0220] Subsequently, the second electrode 903 was formed above the electron injection layer 915. The second electrode 903 was formed using aluminum by an evaporation process to a thickness of 200 nm. In this example, the second electrode 903 served as the cathode.

[0221] By the preceding steps, the light-emitting elements, each comprising an EL layer between a pair of electrodes, were formed on the substrate 900. 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 above were functional layers forming the EL layer of an embodiment of the present invention. Furthermore, in all evaporation steps of the preceding manufacturing process, evaporation was carried out by a resistance heating process.

[0222] Each of the light-emitting elements, fabricated as described above, was sealed using a further substrate (not shown) such that the substrate (not shown) was attached to substrate 900 with a UV-curing sealant in a glovebox containing a nitrogen atmosphere, and the substrates were joined together by the sealant applied to the periphery of the light-emitting element formed over substrate 900. During sealing, the sealant was cured with 365 nm UV light at 6 J / cm². 2 It was irradiated to solidify, and the sealant was heated at 80 °C for one hour to stabilize it. <<Betriebseigenschaften der Licht emittierenden Elemente> >

[0223] The operating characteristics of the manufactured light-emitting elements were measured. It should be noted that the measurement was carried out at room temperature (in an atmosphere maintained at 25 °C). The current density-luminance properties are presented as the results of the operating characteristics of the light-emitting elements. Fig. Figure 11 shows the voltage-luminance properties. Fig. Figure 12 shows the luminance-power efficiency characteristics. Fig. 13 shown and the voltage-current characteristics are described in Fig. 14 shown.

[0224] Table 2 shows the initial values ​​of the main properties of light-emitting elements at approximately 1000 cd / m². 2 . [Table 2] Spannung(V) Strom(mA) Current density (mA / cm³) 2 ) Chromatizität(x,y) Luminance (cd / m²) 2 ) Power efficiency (cd / A) Energy efficiency (lm / W) Quantum efficiency (%) Light-emitting element 1 3,6 0,044 1,1 (0,46,0,53) 780 71 62 22 Light-emitting comparison element 2 3,8 0,047 1,2 (0,46,0,53) 850 73 60 23

[0225] The results above show that the light-emitting elements produced in this example have a high efficiency.

[0226] Fig. Figure 15 shows emission spectra at the time when a current with a current density of 2.5 mA / cm² is applied. 2 was applied to the light-emitting element 1 and the light-emitting comparison element 2. As in Fig. As shown in Figure 15, the emission spectrum of each of the light-emitting element 1 and the light-emitting reference element 2 exhibits a peak at about 563 nm, which is presumably from light emission of [Ir(ppy)2(4dppy)] contained in the light-emitting layer 913.

[0227] Next, reliability tests were performed on the light-emitting element 1 and the light-emitting comparison element 2. Fig. Figure 16 shows the results of the reliability tests. Fig. Figure 16 shows the vertical axis representing the normalized luminance (%), where the initial luminance was 100%, and the horizontal axis representing the operating time (h) of the elements. Reliability tests were performed using constant current operating tests with a constant current density of 50 mA / cm². 2 carried out.

[0228] The results of the reliability tests show that light-emitting element 1 exhibits higher reliability than light-emitting comparison element 2, although their efficiencies are essentially the same in Table 2. This is likely due to the fact that, in a comparison between 4.8mFP2Bfpm, used for light-emitting element 1, and 4.6mFP2Pm, used for light-emitting comparison element 2, the structure and robustness of the benzofuropyrimidine framework of 4.8mFP2Bfpm are more stable and higher, respectively, than those of the pyrimidine framework, which is a framework segment of 4.6mFP2Pm exhibiting electron transport properties. Thus, 4.8mFP2Bfpm (structural formula (100)), which is the organic compound of an embodiment of the present invention, is effective in improving the reliability of the light-emitting element. [Example 3]<<Synthesebeispiel 2> >

[0229] This synthesis example describes a method for synthesizing 4,8-bis[3-(triphenylen-2-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mTpP2Bfpm), which is the organic compound of an embodiment of the present invention, represented by the structural formula (130) of embodiment 1. The structure of 4,8mTpP2Bfpm is shown below. <Synthese von 4,8mTpP2Bfpm>

[0230] 1.20 g of 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine, 4.52 g of 4,4,5,5-tetramethyl-2-[3-(triphenylen-2-yl)phenyl]-1,3,2-dioxaborolane, 3.19 g of tripotassium phosphate, 1.12 g of t-butanol, and 50 ml of diethylene glycol dimethyl ether (Diglyme) were placed in a three-necked flask, the mixture was degassed by stirring under reduced pressure, and the air in the three-necked flask was replaced with nitrogen.

[0231] The mixture was heated to 60 °C, 34.5 mg of palladium(II) acetate and 0.111 g of di(1-adamantyl)-n-butylphosphine were added, and stirring was carried out for 40.5 hours at 100 °C.

[0232] 34.0 mg of palladium(II) acetate and 0.114 g of di(1-adamantyl)-n-butylphosphine were added to the mixture and stirring was carried out for 39.5 hours at 120 °C.

[0233] Water was added to the obtained reaction solution, which was then suction-filtered, and the filtrate was washed with water and ethyl acetate. The filtrate was reconstituted with heated toluene and filtered through a filter aid containing Celite, aluminum oxide, and Celite in that order. The resulting solution was concentrated and dried, and the solid was washed with heated toluene, affording 1.43 g of a white target solid in a 37% yield.

[0234] 1.43 g of the white solid were purified by sublimation using a train sublimation process. During sublimation purification, the solid was subjected to a pressure of 1.5 × 10⁻⁶. -2 Pa was heated to 300 °C. After sublimation purification, 1.03 g of the yellow target solid were obtained with a recovery rate of 72%. A synthesis scheme is shown below in (b-1).

[0235] Analysis results through nuclear magnetic resonance ( 1 The 1H NMR spectroscopy of the obtained yellow solid is shown below. 1 H-NMR diagram is shown in Fig. 17 shown. These results reveal that 4.8mTpP2Bfpm, which is the organic compound represented by structural formula (130), was obtained in this example.

[0236] 1 H NMR. δ (CDCl3):7.68-7.75(m,9H), 7.78(d,1H), 7.82(t,1H), 7.87(d,1H), 7.90(d,1H), 8.00(d,1H), 8.05(d,1H), 8.08(d,1H), 8.12(d,1H), 8.14(s,1H), 8.68-8.74(m,8H), 8.78(d,1H), 8.80-8.82(m,2H), 8.84-8.86(m,1H), 8.95(s,1H), 9.03(s,1H), 9.09(s,1H), 9.38(s,1H).

[0237] Fig. Figure 18(A) shows an absorption spectrum and an emission spectrum of 4.8 mTpP2 Bfpm in a toluene solution. The horizontal axis represents the wavelength, and the vertical axes represent the absorption intensity and the emission intensity.

[0238] The absorption spectrum was measured using a UV-VIS spectrophotometer (V550, manufactured by JASCO Corporation). The emission spectrum was measured using a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK).

[0239] Fig. 18(A) shows that 4.8mTpP2Bfpm in the toluene solution has absorption peaks at about 335 nm, 314 nm and 280 nm and an emission wavelength peak at about 394 nm (excitation wavelength: 300 nm).

[0240] Next, the absorption and emission spectra of a 4.8 mTpP 2 Bfpm solid thin film were measured. The solid thin film was produced by a vacuum evaporation process over a quartz substrate. The absorption spectrum was measured with a UV-VIS spectrophotometer (U-4100, manufactured by Hitachi High-Technologies Corporation). The emission spectrum was measured with a fluorescence spectrophotometer (FS920, manufactured by Hamamatsu Photonics KK). The obtained absorption and emission spectra of the solid thin film are presented in Fig. Figure 18(B) shows the horizontal axis representing the wavelength and the vertical axes representing the absorption intensity and the emission intensity.

[0241] The result in Fig. Figure 18(B) shows that the solid thin film of 4.8mTpP2Bfpm has absorption peaks at about 315 nm and 273 nm and an emission wavelength peak at about 426 nm (excitation wavelength: 330 nm).

[0242] Differential scanning calorimetry (DSC measurement) was also performed at 4.8 mTpP2 Bfpm. A Pyris 1 DSC, manufactured by PerkinElmer Japan Co., Ltd., was used for the measurement. It should be noted that the measurement was performed as follows: A cycle in which the temperature was increased from -10 °C to 480 °C at a rate of 40 °C / min, held at 480 °C for one minute, and then decreased from 480 °C to -10 °C at a rate of 100 °C / min was performed twice. A third cycle was then performed in which the temperature was increased from -10 °C to 480 °C at a rate of 10 °C / min, held at 480 °C for one minute, and then decreased from 480 °C to -10 °C at a rate of 100 °C / min.

[0243] During the measurement, this measurement was carried out up to the third cycle, and from the result, with the increasing temperature in the third cycle, it was determined that the glass transition temperature T g The temperature was 167 °C. From this result, it was determined that 4.8mTpP2Bfpm has high heat resistance. [Example 4]

[0244] In this example, a light-emitting element 3 of an embodiment of the present invention was produced using 4,8-bis[3-(triphenylen-2-yl)phenyl]-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mTpP2Bfpm) (structural formula (130)) in its light-emitting layer and electron transport layer, and the measured property results of the light-emitting element 3 are shown.

[0245] The elemental structure of the light-emitting element 3, which was produced in this example, was similar to the elemental structure that was determined in Example 2 using Fig. The structure of the elements has been described in section 10. Table 3 shows specific layer structures. Chemical formulas of materials used in this example are shown below. [Table 3] first electrode Hole injection layer Hole transport layer Light-emitting layer electron transport layer Electron injection layer second electrode Light-emitting element 3 ITSO (70 nm) DBT3P-II:MoOx(2:1 50 nm) PCBBi1BP(20 nm) * 4.8mTpP2Bfpm(20 nm) NBphen(15 nm) LiF(1 nm) Al(200 nm) * 4.8mTpP2Bfpm:PCCP:[Ir(ppy)2(4dppy)] (0.6:0.4:0.1 40 nm) <<Betriebseigenschaften des Licht emittierenden Elements 3> >

[0246] The operating characteristics of the manufactured light-emitting element 3 were measured. It should be noted that the measurement was carried out at room temperature (in an atmosphere maintained at 25 °C).

[0247] Fig. 19, Fig. 20, Fig. 21 and Fig. Figure 22 shows the current density-luminance properties, the voltage-luminance properties, the luminance-current efficiency properties, and the voltage-current properties of the light-emitting element 3.

[0248] Table 4 shows the initial values ​​of the main properties of the light-emitting element 3 at approximately 1000 cd / m². 2 . [Table 4] Voltage (V) Current (mA) Current density (mA / cm³) 2 ) Chromaticity (X,Y) Luminance (cd / m²) 2 ) Power efficiency (cd / A) Energy efficiency (lm / W) Quantum efficiency (%) Light-emitting element 3 3,7 0,047 1,2 (0,45,0,54) 830 70 59 21

[0249] The results above show that the light-emitting element 3 produced in this example has a high efficiency.

[0250] Fig. Figure 23 shows an emission spectrum at the time when a current with a current density of 2.5 mA / cm² is applied. 2 was applied to the light-emitting element 3. As in Fig. As shown in Figure 23, the emission spectrum of the light-emitting element 3 has a peak at about 561 nm, which is presumably from light emission of [Ir(ppy)2(4dppy)] contained in the light-emitting layer 913.

[0251] Next, a reliability test was performed on the light-emitting element 3. Fig. Figure 24 shows the results of the reliability tests. Fig. Figure 24 shows that the vertical axis represents the normalized luminance (%), with an initial luminance of 100%, and the horizontal axis represents the operating time (h) of the element. Reliability tests were performed using constant current operating tests with a constant current density of 50 mA / cm². 2 carried out.

[0252] The results of the reliability tests show that the light-emitting element 3 exhibits high reliability. This is likely due to the stable and robust structure and structure of the benzofuropyrimidine framework, which is a framework segment exhibiting electron transport properties, in 4.8mTpP2Bfpm, the compound used for the light-emitting element 3. Thus, 4.8mTpP2Bfpm (structural formula (130)), which is the organic compound of an embodiment of the present invention, is effective in improving the reliability of the light-emitting element. Reference sign

[0253] 101: first electrode, 102: second electrode, 103: EL layer, 103a, 103b: EL layer, 104: charge generation layer, 111, 111a, 111b: hole injection layer, 112, 112a, 112b: hole transport layer, 113, 113a, 113b: light-emitting layer, 114, 114a, 114b: electron transport layer, 115, 115a, 115b: electron injection layer, 200R, 200G, 200B: optical path length, 201: first substrate, 202: transistor (FET), 203R, 203G, 203B, 203W: light-emitting element, 204: EL layer 205: second substrate, 206R, 206G, 206B: color filter, 206R', 206G', 206B': color filter, 207: first electrode, 208: second electrode, 209: black layer (black matrix), 210R, 210G: conductive layer, 301: first substrate, 302: pixel section, 303: driver circuit section (source line driver circuit), 304a, 304b: driver circuit section (gate line driver circuit), 305: sealant, 306: second substrate, 307: connecting line, 308: FPC, 309: FET, 310: FET, 311: FET, 312: FET313: first electrode, 314: insulator, 315: EL layer, 316: second electrode, 317: light-emitting element, 318: space, 900: substrate, 901: first electrode, 903: second electrode, 911: hole injection layer, 912: hole transport layer, 913: light-emitting layer, 914: electron transport layer, 915: electron injection layer, 4000: illumination device, 4001: substrate, 4002: light-emitting element, 4003: substrate, 4004: first electrode, 4005: EL layer, 4006: second electrode, 4007: electrode, 4008: electrode, 4009: auxiliary line, 4010: insulating layer, 4011: Sealing substrate, 4012: Sealant, 4013: Desiccant, 4200: Lighting device, 4201: Substrate, 4202: Light-emitting element, 4204: First electrode, 4205: EL layer, 4206: Second electrode, 4207: Electrode, 4208: Electrode, 4209: Auxiliary conductor, 4210: Insulating layer, 4211: Sealing substrate, 4212: Sealant, 4213: Barrier film, 4214: Planarizing film, 5101: Headlight,5102: Wheel cover, 5103: Door, 5104: Display section, 5105: Steering wheel, 5106: Gearshift lever, 5107: Seat, 5108: Interior rearview mirror, 7000: Housing, 7001: Display section, 7002: Second display section, 7003: Speaker, 7004: LED lamp, 7005: Control buttons, 7006: Connection port, 7007: Sensor, 7008: Microphone, 7009: Switch, 7010: Infrared port, 7011: Memory media read section, 7012: Bracket, 7013: Earpiece, 7014: Antenna, 7015: Shutter release button, 7016: Image receiver section, 7018: Foot, 7019: Microphone, 7020: Camera 7021: external connection section, 7022, 7023: operating buttons, 7024: connection port, 7025: strap, 7026: buckle, 7027: icon indicating the time, 7028: additional icon, 9310: portable information terminal, 9311: display section, 9312: display area, 9313: hinge, 9315: housing< / substrat> < / ladungserzeugungsschicht> < / elektronentransportschicht>

Claims

[1] Organic compound represented by the general formula (G1), where in the formula represent: Q Oxygen or sulfur; A 1 and A 2 each independently of each other a substituted or unsubstituted polycyclic aromatic hydrocarbon; m is an integer from 0 to 4; n is an integer from 1 to 4; and R 1 to R 12 Each independently of one another hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms. [2] Organic compound according to claim 1, wherein the organic compound is represented by the general formula (G2), [3] Organic compound according to claim 1, wherein the organic compound is represented by the general formula (G3), [4] Organic compound according to any one of claims 1 to 3, wherein A 1 and A 2 Each is independently a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group. [5] Organic compound according to any one of claims 1 to 3, wherein A 1 and A 2 each independently represents one of the general formulas (A-1) to (A-14), where in the formulas R A1 to R A15Each can independently represent hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms. [6] Organic compound represented by the general formula (G4), where in the formula: Q Oxygen or sulfur; m is an integer from 0 to 4; n is an integer from 1 to 4; and R 1 to R 30 Each independently of one another hydrogen, an alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group with 6 to 13 carbon atoms. [7] Organic compound according to claim 6, wherein the organic compound is represented by the general formula (G5), [8] Organic compound according to claim 6, wherein the organic compound is represented by the structural formula (100), [9] Light-emitting element comprising the organic compound according to any one of claims 1, 2, 3, 6 and 7. [10] Light-emitting device comprising: the light-emitting element according to claim 9; and a transistor and / or a substrate. [11] Electronic device comprising: the light-emitting device according to claim 10; and a microphone and / or a camera and / or a control button and / or an external connection section and / or a speaker. [12] Lighting device comprising: the light-emitting element according to claim 9; and a housing and / or a cover and / or a support base.

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