Organic compounds

Abstract

To provide a novel organic compound, that is, a novel organic compound that is effective in improving the element characteristics and reliability.SOLUTION: The present invention provides an organic compound with a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton, represented by General Formula (G1), where Q represents oxygen or sulfur; α represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; n represents an integer of 0 to 4; A1 represents a group including an aryl group or a heteroaryl group and having 6 to 100 carbon atoms; R1 to R4 each represent hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or the like; and A2 represents a condensed ring.SELECTED DRAWING: None

Description

[Technical field]

[0001] One aspect of the present invention is a benzofuropyrimidine skeleton or a benzothieno skeleton in which a fused ring is directly bonded. The present invention relates to a compound having a pyrimidine skeleton, or a light-emitting device having the compound. The present invention also relates to a display device, an electronic device, and a lighting device that include the light-emitting element.

[0002] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. However, one embodiment of the present invention is not limited to the above technical fields. The present invention relates to an object, a method, a manufacturing method, or a driving method. process, machine, manufacture, or composition of matter Specifically, the present invention relates to a semiconductor device, a display device, a liquid crystal display device, etc. It is possible. [Background technology]

[0003] Light-emitting elements (also called organic EL elements) are thin, lightweight, and have an EL layer sandwiched between a pair of electrodes. These features include high-speed response to input signals and low power consumption. This display is attracting attention as the next generation of flat panel displays.

[0004] The light-emitting element is a device that emits light by applying a voltage between a pair of electrodes, and the electrons injected from each electrode are The electrons and holes recombine in the EL layer, and the luminescent material (organic compound) contained in the EL layer becomes excited. When the excited state returns to the ground state, light is emitted. , singlet excited state (S * ) and triplet excited states (T * ) and emission from the singlet excited state. The light emitted from the triplet excited state is called fluorescence, and the light emitted from the triplet excited state is called phosphorescence. The statistical generation ratio of these is S * :T * =1:3. From luminous materials The emission spectrum obtained is specific to the luminescent material, and different types of organic compounds emit By using it as an optical substance, it is possible to obtain light-emitting elements that emit light of various colors.

[0005] Regarding such light-emitting devices, in order to improve the device characteristics, improvements in the device structure and material development have been carried out. Developments in this field are being actively pursued (see, for example, Patent Document 1). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2010-182699 A Summary of the Invention [Problem to be solved by the invention]

[0007] In the development of light-emitting devices, the organic compounds used in the light-emitting devices are extremely important in improving their properties. Therefore, in one aspect of the present invention, a novel organic compound is provided. The present invention provides a novel organic compound that is effective in improving the electronic characteristics and reliability. In the present invention, a novel organic compound that can be used for a light-emitting element is provided. In the present invention, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. A novel light-emitting element that is highly efficient and reliable and uses a novel organic compound according to one embodiment of the present invention is provided. Also provided is a novel light-emitting device, a novel electronic device, or a novel lighting device. The description of these problems does not preclude the existence of other problems. The embodiment does not necessarily have to solve all of these problems. The above will become apparent from the description in the specification, drawings, claims, etc. It is possible to extract other issues from the descriptions in the patent, claims, etc. [Means for solving the problem]

[0008] One aspect of the present invention is a compound having a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton. It is an organic compound represented by the following general formula (G1).

[0009] [ka]

[0010] In the general formula (G1), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Yes R represents a group having 6 to 100 carbon atoms containing an aryl group or a heteroaryl group. 1 ~R 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; 6 to 13, and any one of the aryl groups. 2 represents a fused ring.

[0011] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0012] [ka]

[0013] In the general formula (G2), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 2 represents a fused ring.

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

[0015] [ka]

[0016] In the general formula (G3), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 2 represents a fused ring.

[0017] Another embodiment of the present invention is an organic compound represented by the following general formula (G4).

[0018] [ka]

[0019] In the general formula (G4), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 3 represents a fused ring.

[0020] In general formula (G4), A 3 Naphthalene, fluorene, and phenanthrene skeletons It is preferable that the aromatic hydrocarbon group is a condensed aromatic hydrocarbon group having a triphenylene skeleton or the like.

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

[0022] [ka]

[0023] In the general formula (G5), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 4 represents a fused ring.

[0024] In general formula (G5), A 4 Naphthalene, fluorene, and phenanthrene skeletons It is preferable that the aromatic hydrocarbon group is a condensed aromatic hydrocarbon group having a triphenylene skeleton or the like.

[0025] Another embodiment of the present invention is an organic compound represented by the following general formula (G6).

[0026] [ka]

[0027] In the general formula (G6), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 4 represents a fused ring.

[0028] As shown in the general formulas (G3), (G4), and (G6), the fused ring is a benzofuro[3 ,2-d]pyrimidine or benzothieno[3,2-d]pyrimidine skeleton. It is preferable to combine them in order to obtain a light emitting element having a long life.

[0029] In addition, in the above general formulae (G1) to (G6), A 1 is a skeleton having hole transport properties The hole transporting skeleton is a diarylamino group or a condensed aromatic It is preferably either an aromatic hydrocarbon ring or a π-excessive condensed heteroaromatic ring.

[0030] In addition, in the above general formulae (G2) to (G6), A 1 is substituted or unsubstituted A condensed aromatic hydrocarbon ring or a substituted or unsubstituted π-excessive condensed heteroaromatic ring. In particular, in consideration of the hole transport property, a π-excess type condensed heteroaromatic ring is preferred. Among them, the dibenzothiophene skeleton, the dibenzofuran skeleton, and the carbazole skeleton Most preferred are substituted or unsubstituted fused heteroaromatic rings having the formula:

[0031] On the other hand, in the above general formulae (G1) to (G6), A 2 , A 3 , and A 4 Condensation of The rings are each independently a substituted or unsubstituted fused aromatic hydrocarbon ring, or a substituted or The aromatic ring is preferably an unsubstituted π-excessive condensed heteroaromatic ring. 2 , A 3 , and A 4 each independently represents a substituted or unsubstituted dibenzothiophene skeleton, Substituted or unsubstituted dibenzofuran skeleton, substituted or unsubstituted carbazole skeleton, substituted or an unsubstituted naphthalene skeleton, a substituted or unsubstituted fluorene skeleton, a substituted or Either an unsubstituted triphenylene skeleton or a substituted or unsubstituted phenanthrene skeleton However, the fused aromatic hydrocarbon ring is preferably an unsaturated ring. As the unsaturated fused aromatic hydrocarbon ring, is preferably a fused aromatic hydrocarbon ring in which the carbon atoms constituting the ring do not have an sp3 bond, and specifically Examples of the ring include a naphthalene ring, a triphenylene ring, and a phenanthrene ring.

[0032] A in the above general formulae (G1) to (G6) 1 , A 2 , A 3 , and A 4 Is that Each of the following general formula (A 1 -1) to general formula (A 1 -17) It is characterized by:

[0033] [ka]

[0034] The above general formula (A 1 -1) to general formula (A 1 -17) in R A1 ~R A11 Is that each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 1 carbon atoms; 3 aryl groups.

[0035] In the above general formulae (G1) to (G6), α is represented by the following general formulae (Ar-1) to (Ar-6). An organic compound represented by any one of the formulas (Ar-18):

[0036] [ka]

[0037] Another aspect of the present invention is a compound represented by the structural formula (100), the structural formula (101), or the structural formula (102). It is an organic compound represented by the formula:

[0038] [ka]

[0039] Another embodiment of the present invention is a light-emitting element using the organic compound according to any one of the above embodiments of the present invention. Note that the present invention also includes a light-emitting element having a host material in addition to the above organic compound.

[0040] Another embodiment of the present invention is a light-emitting element using the organic compound according to any one of the above embodiments of the present invention. In addition, the EL layer between the pair of electrodes and the light-emitting layer included in the EL layer may include the The present invention also includes a light-emitting element formed using a certain organic compound. In addition to the element, a light-emitting device having a transistor, a substrate, etc. is also included in the scope of the invention. In addition to these light-emitting devices, microphones, cameras, operation buttons, external connectors, housings, covers, etc. The scope of the invention also includes electronic devices and lighting devices having a speaker, a support stand, or the like.

[0041] Another embodiment of the present invention includes a light-emitting device having a light-emitting element, and further includes a lighting device having the light-emitting device. Therefore, the term "light-emitting device" in this specification includes a light-emitting device such as an image display device. It also refers to a light source (including lighting equipment) that is connected to a light-emitting device, such as an FPC (Fl exible printed circuit) or TCP (Tape Carrier A module with a connector such as a printer package, a TCP A module with a printed wiring board or a light emitting element with COG (Chip On Glass) All modules with ICs directly mounted using the assembly method are included in the light emitting device. It shall be so. Effect of the Invention

[0042] One embodiment of the present invention can provide a novel organic compound. In addition, in one embodiment of the present invention, a novel organic compound that is effective in It is possible to provide a novel organic compound that can be used in a light-emitting element. In one embodiment, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. In addition, a highly efficient and reliable photovoltaic cell using a novel organic compound according to one embodiment of the present invention can be obtained. In addition, a novel light-emitting device, a novel electronic device, or the like can be provided. It should be noted that the description of these effects may be omitted if other effects are mentioned. However, it is not necessary for one embodiment of the present invention to have all of these effects. It is not necessary for the invention to have the above effects. Effects other than these can be understood from the description in the specification, drawings, claims, etc. It is obvious that there are other effects than these from the description, drawings, claims, etc. It is possible to extract the results. [Brief description of the drawings]

[0043] [Figure 1] 1A to 1C are diagrams illustrating a structure of a light-emitting element. [Diagram 2] 1A and 1B are diagrams illustrating a light-emitting device. [Diagram 3] 1A and 1B are diagrams illustrating a light-emitting device. [Figure 4] 1A to 1C are diagrams illustrating electronic devices. [Diagram 5] 1A to 1C are diagrams illustrating electronic devices. [Figure 6] FIG. [Figure 7] 1A and 1B are diagrams illustrating a lighting device. [Figure 8] 1A and 1B are diagrams illustrating a lighting device. [Figure 9] 1H-NMR chart of the organic compound shown in structural formula (100). [Figure 10] UV-visible absorption and emission spectra of the organic compound represented by structural formula (100). [Figure 11] MS spectrum of the organic compound shown in structural formula (100). [Figure 12] 1H-NMR chart of the organic compound shown in structural formula (101). [Figure 13] UV-visible absorption and emission spectra of the organic compound represented by structural formula (101). [Figure 14] MS spectrum of the organic compound shown in structural formula (101). [Figure 15] 1H-NMR chart of the organic compound shown in structural formula (102). [Figure 16] UV-visible absorption spectrum and emission spectrum of the organic compound represented by structural formula (102). [Figure 17] MS spectrum of the organic compound shown in structural formula (102). [Figure 18] 1A to 1C are diagrams illustrating light-emitting elements. [Figure 19] FIG. 13 shows current density-luminance characteristics of Light-emitting Elements 1, 2, and 3. [Figure 20] FIG. 13 shows voltage-luminance characteristics of Light-emitting Elements 1, 2, and 3. [Figure 21] FIG. 13 shows luminance-current efficiency characteristics of Light-emitting Elements 1, 2, and 3. [Figure 22] 13 is a graph showing voltage-current characteristics of the light-emitting element 1, the light-emitting element 2, and the light-emitting element 3. [Diagram 23] FIG. 2 shows emission spectra of the light-emitting elements 1, 2, and 3. [Figure 24] 1 shows the reliability of the light-emitting element 1, the light-emitting element 2, and the light-emitting element 3. [Diagram 25] FIG. 13 shows current density-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 5. [Figure 26] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 4 and the comparative light-emitting element 5. [Figure 27] FIG. 13 shows luminance-current efficiency characteristics of the light-emitting element 4 and the comparative light-emitting element 5. [Figure 28] 13 shows voltage-current characteristics of the light-emitting element 4 and the comparative light-emitting element 5. [Figure 29] FIG. 13 shows emission spectra of the light-emitting element 4 and the comparative light-emitting element 5. [Diagram 30] 13 shows the reliability of the light-emitting element 4 and the comparative light-emitting element 5. [Diagram 31] 1H-NMR chart of the organic compound shown in structural formula (103). [Diagram 32] 1H-NMR chart of the organic compound shown in structural formula (116). [Diagram 33] 13 is a graph showing current density-luminance characteristics of the light-emitting element 6 and the light-emitting element 7. FIG. [Diagram 34] 13 shows voltage-luminance characteristics of the light-emitting element 6 and the light-emitting element 7. FIG. [Diagram 35] 13 shows luminance-current efficiency characteristics of the light-emitting elements 6 and 7. FIG. [Diagram 36] 13 is a graph showing voltage-current characteristics of the light-emitting element 6 and the light-emitting element 7. FIG. [Figure 37] FIG. 4 shows emission spectra of the light-emitting elements 6 and 7. [Figure 38] 13A and 13B are graphs showing the reliability of the light-emitting element 6 and the light-emitting element 7. [Figure 39] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 8. [Diagram 40] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 8. [Diagram 41] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 8. [Diagram 42] FIG. 13 is a graph showing voltage-current characteristics of the light-emitting element 8. [Diagram 43] FIG. 2 shows an emission spectrum of the light-emitting element 8. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0044] Hereinafter, the embodiment of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details are not limited thereto without departing from the spirit and scope of the present invention. Therefore, the present invention is not limited to the above embodiment. It is not to be construed as being limited to the following:

[0045] In addition, the position, size, range, etc. of each component shown in the drawings are not necessarily the same as in the actual embodiment, for ease of understanding. Therefore, the disclosed invention may not necessarily represent the actual position, size, range, etc. The present invention is not necessarily limited to the position, size, range, etc. disclosed in the drawings.

[0046] In addition, in this specification and the like, when explaining the configuration of the invention using drawings, the same The reference numerals are commonly used even among different drawings.

[0047] (Embodiment 1) In this embodiment, an organic compound which is one embodiment of the present invention will be described.

[0048] In addition, one embodiment of the present invention is a compound having a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton. and is an organic compound represented by the following general formula (G1).

[0049] [ka]

[0050] In the general formula (G1), Q represents oxygen or sulfur. A represents a substituted arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 represents a group having 6 to 100 carbon atoms including aryl or heteroaryl. 1 ~R 4 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or an unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted carbon A represents any one of aryl groups having a number of 6 to 13. 2 represents a fused ring.

[0051] In the general formula (G1), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton The benzene side of the condensed ring (A 2 ) is directly bonded to improve thermal properties and light-emitting The reliability of the system can be improved.

[0052] Another embodiment of the present invention is an organic compound represented by the following general formula (G2).

[0053] [ka]

[0054] In the general formula (G2), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 2 represents a fused ring.

[0055] In the general formula (G2), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton The benzene side of the condensed ring (A 2 ) is directly bonded to improve thermal properties and light-emitting The reliability of the system can be improved.

[0056] Another embodiment of the present invention is an organic compound represented by the following general formula (G3).

[0057] [ka]

[0058] In the general formula (G3), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 2 represents a fused ring.

[0059] As shown in general formula (G3), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton Adding a condensed ring to the 8-position of the skeleton can lead to the formation of compounds such as halides that adversely affect the characteristics and reliability of devices. Such materials with reduced impurities can be easily synthesized, and are advantageous in terms of the cost of the raw materials. In this case, a light-emitting device having a long driving life can be obtained. 3 Or, the general formula (G6) A 4 also has the same effect.

[0060] As shown in the general formula (G3), the benzofuropyrimidine skeleton or the benzothienopyrimidine skeleton Adding a condensed ring to the 8-position of the amide skeleton not only improves electrochemical stability and film quality, but also It is possible to express a high T1 level. 3 Or general formula (G6) A 4 also has the same effect.

[0061] In addition, n in general formula (G3) is preferably 1 or 2.

[0062] In the general formula (G3), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton The benzene side of the condensed ring (A 2 ) is directly bonded to improve thermal properties and light-emitting The reliability of the system can be improved.

[0063] Another embodiment of the present invention is an organic compound represented by the following general formula (G4).

[0064] [ka]

[0065] In the general formula (G4), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having 6 to 100 carbon atoms in total, or R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently Hydrogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A represents one of the following: 3 represents a fused ring.

[0066] In general formula (G4), A 3 Naphthalene, fluorene, and phenanthrene skeletons It is more preferable that the aromatic hydrocarbon group is a condensed aromatic hydrocarbon group having a triphenylene skeleton or the like.

[0067] In addition, in general formula (G4), A 1 Dibenzothiophene skeleton, dibenzofuran skeleton, It is a substituted or unsubstituted π-excessive condensed heteroaromatic ring having a carbazole skeleton. preferable.

[0068] In general formula (G4), n is preferably 1 or 2.

[0069] In the general formula (G4), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton The benzene side of the condensed ring (A 3 ) is directly bonded to improve thermal properties and light-emitting The reliability of the system can be improved.

[0070] Another embodiment of the present invention is an organic compound represented by the following general formula (G5).

[0071] [ka]

[0072] In the general formula (G5), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 4 represents a fused ring.

[0073] In general formula (G5), A 4 Naphthalene, fluorene, and phenanthrene skeletons It is more preferable that the aromatic hydrocarbon group is a condensed aromatic hydrocarbon group having a triphenylene skeleton or the like.

[0074] In addition, in general formula (G5), A 1 Dibenzothiophene skeleton, dibenzofuran skeleton, It is a substituted or unsubstituted π-excessive condensed heteroaromatic ring having a carbazole skeleton. preferable.

[0075] In general formula (G5), n is preferably 1 or 2.

[0076] In the general formula (G5), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton The benzene side of the condensed ring (A 4 ) is directly bonded to improve thermal properties and light-emitting The reliability of the system can be improved.

[0077] Another embodiment of the present invention is an organic compound represented by the following general formula (G6).

[0078] [ka]

[0079] In the general formula (G6), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Total charcoal A substituted or unsubstituted aryl group having a prime number of 6 to 100, or a substituted or unsubstituted aryl group having a total carbon number of 6 to 100 R represents a substituted or unsubstituted heteroaryl group. 1 ~R 4 are each independently , hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted carbon a cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; In addition, A 4 represents a fused ring.

[0080] In general formula (G6), A 4 Dibenzothiophene skeleton, dibenzofuran skeleton, carba It is preferably a π-excessive condensed heteroaromatic ring having a zole skeleton or the like.

[0081] In addition, in general formula (G6), A 4 The benzofuropyrimidine skeleton or benzothienopyrimidine skeleton Substitution at position 8 of the lysine skeleton is preferred.

[0082] In addition, in general formula (G6), A 1 Dibenzothiophene skeleton, dibenzofuran skeleton, It is a substituted or unsubstituted π-excessive condensed heteroaromatic ring having a carbazole skeleton. preferable.

[0083] In general formula (G6), n is preferably 1 or 2.

[0084] In the general formula (G6), a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton The benzene side of the condensed ring (A 4 ) is directly bonded to improve thermal properties and light-emitting The reliability of the system can be improved.

[0085] In one embodiment of the present invention, in the above general formulas (G1) to (G6), A 1 but The compound represented by the above general formula (G1) to general formula (G6) has a skeleton having a hole transporting property. ) are benzofuro[3,2-d]pyrimidines or benzothieno[3,2- d] The pyrimidine skeleton has electron transport properties, but the hole transport skeleton is By further adding, a bipolar compound can be provided. The compound is stable to both holes and electrons. In addition, when used as a host for a light-emitting device, It also acts to expand the recombination region of carriers, resulting in a longer life of the light-emitting element. Examples of the skeleton having the functional group include a diarylamino group or a condensed aromatic hydrocarbon ring or a π Excessive condensed heteroaromatic rings, etc.

[0086] From this viewpoint, in the above general formulae (G2) to (G6), A 1 also substitute or unsubstituted fused aromatic hydrocarbon rings, or substituted or unsubstituted π-excessive fused complex rings. In particular, in consideration of hole transport properties, a π-excess type condensed heteroaromatic ring is preferred. Aromatic rings are preferred, and among them, dibenzothiophene skeletons, dibenzofuran skeletons, and carbazole skeletons are preferred. Substituted or unsubstituted fused heteroaromatic rings having one of the 5 positions are most suitable. The fused heteroaromatic ring containing a membered ring provides both high hole transport properties and chemical stability.

[0087] In the organic compound shown in this embodiment, R 1 ~R 4 are all hydrogen, It is advantageous in terms of ease of synthesis and the cost of the raw materials, and furthermore, it is a compound with a relatively low molecular weight. Therefore, the structure is suitable for vacuum deposition, which is particularly preferable.

[0088] On the other hand, in the above general formulae (G1) to (G6), A 2 , A 3 , and A 4 Condensation of The rings are each independently a substituted or unsubstituted fused aromatic hydrocarbon ring, or a substituted or The fused ring is preferably an unsubstituted π-excessive fused heteroaromatic ring. By applying these aromatic fused rings, chemical stability is improved by resonance stabilization. This directly relates to the lifespan of the light-emitting device. It is also preferable from the viewpoint.

[0089] Specifically, in the above general formulae (G1) to (G6), A 2 , A 3 , and A 4 each independently represents a substituted or unsubstituted dibenzothiophene skeleton, Substituted dibenzofuran skeleton, substituted or unsubstituted carbazole skeleton, substituted or unsubstituted A naphthalene skeleton, a substituted or unsubstituted fluorene skeleton, a substituted or unsubstituted triflate skeleton, A fused ring having either a phenylene skeleton or a substituted or unsubstituted phenanthrene skeleton. It is characterized by the fact that

[0090] However, the above-mentioned fused aromatic hydrocarbon ring is preferably an unsaturated fused aromatic hydrocarbon ring having a small ring strain. From the viewpoint of chemical stability, a hydrocarbon ring is preferred. The ring is preferably a fused aromatic hydrocarbon ring in which the carbon atoms constituting the ring do not have an sp3 bond. Specifically, the ring is a naphthalene ring, a triphenylene ring, or a phenanthrene ring.

[0091] In the above general formulae (G1) to (G6), A 1 , A 2 , A 3 , and A 4 Yes, that Each of the following general formula (A 1 -1) to general formula (A 1 -17) It is characterized by:

[0092] [ka]

[0093] The above general formula (A 1 -1) to general formula (A 1 -17) in R A1 ~R A11 Is that each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 1 carbon atoms; 3 aryl groups.

[0094] In the above general formulae (G1) to (G6), the α is represented by the following general formula (Ar-1): It is characterized in that it is any one of the following general formulas to (Ar-18).

[0095] [ka]

[0096] In the above general formulae (G1) to (G6), a substituted or unsubstituted alkyl group having 6 to 13 carbon atoms is a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or Substituted or unsubstituted monocyclic saturated hydrocarbon group having 3 to 20 carbon atoms, substituted or unsubstituted carbon When any of the polycyclic saturated hydrocarbon groups having 7 to 10 carbon atoms has a substituent, the substituent and The methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s C1 to C7 groups such as ec-butyl, tert-butyl, pentyl, and hexyl groups Alkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, 8,9,1 cycloalkyl groups having 5 to 7 carbon atoms, such as 0-trinorbornanyl groups, phenyl groups, Examples of the aryl group include an aryl group having 6 to 12 carbon atoms, such as a naphthyl group or a biphenyl group.

[0097] In addition, the monocyclic saturated hydrocarbon groups having 3 to 20 carbon atoms in the above general formulae (G1) to (G6) Specific examples of the cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and a cyclohexyl group. butyl group, 2-methylcyclohexyl group, cyclooctyl group, cyclononyl group, cyclode Examples thereof include a silyl group and a cycloicosyl group.

[0098] In addition, the polycyclic saturated hydrocarbon groups having 7 to 10 carbon atoms in the above general formulas (G1) to (G6) Specific examples of the alkyl group include 8,9,10-trinorbornanyl, decahydronaphthyl, and adatomyl. Examples thereof include a mantyl group.

[0099] Specific examples of the aryl group having 6 to 13 carbon atoms in the above general formulae (G1) to (G6) are Examples include phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, and o-biphenyl. Phenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2-naphthyl group, Examples thereof include a fluorenyl group and a 9,9-dimethylfluorenyl group.

[0100] Specific examples of the alkyl group having 1 to 7 carbon atoms in the above general formulae (G1) to (G6) include The following groups are available: methyl, ethyl, propyl, isopropyl, butyl, and sec-butyl. , isobutyl group, tert-butyl group, pentyl group, isopentyl group, sec-pentyl group tert-pentyl, neopentyl, hexyl, isohexyl, 3-methyl Pentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1,2-dimethylbutyl group, Examples include a 2,3-dimethylbutyl group and an n-heptyl group.

[0101] Next, specific structural formulas of the organic compounds according to embodiments of the present invention are shown below. However, the present invention is not limited to these.

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] The organic compounds represented by the above structural formulas (100) to (150) are represented by the above general formula (G1) This is an example of the organic compound represented by the formula (G6), which is one embodiment of the present invention. The items are not limited to these.

[0108] Next, one embodiment of the present invention relates to a method for synthesizing an organic compound represented by the following general formula (G1): An example will be described.

[0109] [ka]

[0110] In the general formula (G1), Q represents oxygen or sulfur. α represents a substituted or unsubstituted represents an arylene group having 6 to 13 carbon atoms, and n represents an integer of 0 to 4. 1 Yes R represents a group having 6 to 100 carbon atoms including aryl or heteroaryl. 1 ~R 4 teeth, Each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or is an unsubstituted cycloalkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 or more carbon atoms. In addition, A represents any one of the aryl groups represented by the formulas 1 to 13. 2 represents a fused ring.

[0111] <Method for synthesizing organic compound represented by general formula (G1)> The organic compound represented by the above general formula (G1) is a benzofuropyrimidine derivative or It is a zothienopyrimidine derivative, and various reactions can be applied to its synthesis. For example, the organic compound represented by the general formula (G1) can be synthesized by the following simple synthesis scheme: Compounds can be synthesized.

[0112] For example, as shown in the following scheme (a), a substituted or unsubstituted benzofuropyrimidine A halogen compound (A1) containing a benzothienopyrimidine skeleton or a substituted or It can be obtained by reacting a fused ring (A2) containing an unsubstituted aryl group.

[0113] [ka]

[0114] In this case, as shown in the following scheme (b), a substituted or unsubstituted benzofuropyrimidinyl group is A dihalogen compound (B1) containing a pyrimidine skeleton or a benzothienopyrimidine skeleton and a substituted or unsubstituted or via a reaction with a fused ring boronic acid compound (A2) containing an unsubstituted aryl group, After obtaining the compound (D1), it is reacted with a substituted or unsubstituted fused ring boronic acid compound (B2) to obtain the compound (D1). That's fine.

[0115] [ka]

[0116] Alternatively, as shown in the following scheme (c), a halogen-substituted arylboron oxide compound can be prepared. After obtaining intermediate (D2) through a synthetic reaction with compound (C1), substituted or unsubstituted condensation is performed. The intermediate (D3) is obtained by reaction of the ring with a boronic acid compound (C2), and then the intermediate (D3) is substituted or An unsubstituted fused ring boronic acid compound (B2) may be reacted. 1 ~B 4 Habo It also represents cyclic triol borate salts, etc. As the triol borate salt, in addition to the lithium salt, potassium salt and sodium salt may be used.

[0117] [ka]

[0118] In the synthetic schemes (a), (b), and (c), X is a halogen group or a trifluoride group. Q represents an oxygen or sulfur atom; A 1 The total number of carbon atoms is 6 to 100. or an unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group having a total of 6 to 100 carbon atoms. represents an aryl group; A 2 represents a fused ring, R 1 ~R 4 are each independently hydrogen, substituted or or an unsubstituted alkyl group having 1 to 6 carbon atoms; a cycloalkyl group, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; represents one or more, α represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, and n represents 0. Represents an integer from 1 to 4.

[0119] The above compounds (A1), (A2), (B1), (B2), (C1) and (C2) can be used in various Since various types are commercially available or can be synthesized, the general formula (G1) Benzofuropyrimidine derivatives or benzothienopyrimidine derivatives are available in a wide variety of types. Therefore, the compound according to one embodiment of the present invention has a wide variety of variations. There is a characteristic that it is.

[0120] In the above synthesis schemes (a), (b) and (c), tin was synthesized using a palladium catalyst. In the case of the Ki-Miyaura cross-coupling reaction, X represents a halogen group or a triflate group. As the halogen, iodine, bromine or chlorine is preferred. Palladium compounds such as diphenylideneacetone (dipalladium(0)) and palladium(II) acetate di(1-adamantyl)-n-butylphosphine, 2'-(dicyclohexylphosphine) Ligands such as naphthalene (phenyl)acetophenone ethylene ketal can also be used. Organic bases such as sodium tert-butoxide, cesium fluoride, tripotassium phosphate, and charcoal Inorganic bases such as potassium hydroxide can be used. benzene, tetrahydrofuran, mesitylene, diglyme, etc. can be used. However, the reagents that can be used in this reaction are not limited to these. do not have.

[0121] As described above, the benzofuropyrimidine derivative or benzothieno compound which is one embodiment of the present invention is Although an example of a method for synthesizing a pyrimidine derivative has been described, the present invention is not limited to this. However, they may be synthesized by any other synthesis method.

[0122] In addition, by using the organic compound which is one embodiment of the present invention, a light-emitting element and a light-emitting In addition, a light emitting device having low power consumption can be realized. It is possible to realize a device, a light-emitting device, an electronic device, or a lighting device.

[0123] Note that one embodiment of the present invention has been described in this embodiment. In the following, one embodiment of the present invention will be described. However, the present invention is not limited to the above. That is, various inventive aspects are described in this and other embodiments. Therefore, one embodiment of the present invention is not limited to a specific embodiment.

[0124] The configuration described in this embodiment may be used in appropriate combination with the configurations described in other embodiments. can be done.

[0125] (Embodiment 2) In this embodiment mode, a light-emitting element using the organic compound shown in Embodiment Mode 1 will be described with reference to FIG. I will explain this in more detail.

[0126] <Basic structure of light-emitting element> First, the basic structure of a light-emitting element will be described. Specifically, the light-emitting element has a first electrode 101 and a second electrode 1 EL layer 103 is sandwiched between the insulating layer 102 and the insulating film 103 .

[0127] In addition, in FIG. 1B, a plurality of EL layers (two layers in FIG. 1B) are disposed between a pair of electrodes. a, 103b), and a stacked structure (tandem structure) having a charge generating layer 104 between the EL layers. The light-emitting element of the tandem structure is an emission element that can be driven at a low voltage and consumes low power. Optical devices can be realized.

[0128] When a voltage is applied between the first electrode 101 and the second electrode 102, the charge generating layer 104 Electrons are injected into one EL layer (103a or 103b) and the other EL layer (103b or 1B, the first electrode 1 When a voltage is applied to the charge generating layer 101 so that the potential of the charge generating layer 101 becomes higher than that of the second electrode 102, Electrons are injected from the electrode 4 into the EL layer 103a, and holes are injected into the EL layer 103b. .

[0129] The charge generating layer 104 is transparent to visible light from the viewpoint of light extraction efficiency. (Specifically, it is preferable that the transmittance of visible light through the charge generating layer 104 is 40% or more.) In addition, the charge generating layer 104 has a lower conductivity than the first electrode 101 and the second electrode 102. But it still works.

[0130] FIG. 1C shows a stacked structure of an EL layer 103 of a light-emitting element according to one embodiment of the present invention. In this case, however, the first electrode 101 functions as an anode. The EL layer 103 On the first electrode 101, a hole injection layer 111, a hole transport layer 112, The light-emitting layer 113, the electron transport layer 114, and the electron injection layer 115 are laminated in this order. Even in the case of a tandem structure having multiple EL layers as shown in FIG. The L layer is laminated in the above order from the anode side. If the first electrode 102 is the cathode and the second electrode 102 is the anode, the stacking order is reversed.

[0131] The light-emitting layers 113 included in the EL layers (103, 103a, 103b) each contain a light-emitting material or It has a combination of multiple substances and emits fluorescent or phosphorescent light of a desired color. In addition, the light-emitting layer 113 may have a laminated structure with different luminescent colors. In this case, the luminescent material and other materials used in each of the laminated luminescent layers may be the same as those used in the laminated luminescent layers. Different materials may be used for each of the EL layers. 3b) may be used to obtain different luminescent colors. The luminescent material and other materials used may be different materials.

[0132] In the light-emitting element according to one embodiment of the present invention, for example, the first electrode 1 The first electrode 101 is a reflective electrode, the second electrode 102 is a semi-transmissive and semi-reflective electrode, and a micro-optical resonator (microcavity) is formed. By forming a closed cavity structure, the light emitting layer 113 included in the EL layer 103 can be used as a light emitting layer. The emitted light can be resonated between the two electrodes, and the light emitted from the second electrode 102 can be strengthened. do.

[0133] The first electrode 101 of the light-emitting element is made of a conductive material having reflectivity and a conductive material having light-transmitting property. In the case of a reflective electrode having a laminated structure with a conductive material (transparent conductive film), the thickness of the transparent conductive film is controlled. Specifically, the light emitting layer 113 can be optically adjusted by controlling the light emitting layer 113. The distance between the first electrode 101 and the second electrode 102 is mλ / 2, where λ is the wavelength of light. It is preferable to adjust the value so that it is close to m (where m is a natural number).

[0134] In order to amplify the desired light (wavelength: λ) obtained from the light emitting layer 113, the first electrode the optical distance from 101 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, and the optical distance from the electrode 102 to a region (light emitting region) of the light emitting layer 113 where desired light is obtained, , are adjusted to be close to (2m'+1)λ / 4 (where m' is a natural number). The light-emitting region here is preferably a region in which holes in the light-emitting layer 113 and The recombination region with electrons is shown.

[0135] By carrying out such optical adjustment, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be adjusted. This narrows the line width and allows light emission with good color purity to be obtained.

[0136] However, in the above case, strictly speaking, the optical distance between the first electrode 101 and the second electrode 102 is The total thickness from the reflective area of ​​the first electrode 101 to the reflective area of ​​the second electrode 102 is called However, it is necessary to strictly define the reflection area of ​​the first electrode 101 or the second electrode 102. Since it is difficult to determine the position of the first electrode 101 and the second electrode 102, It is assumed that the above-mentioned effect can be obtained by assuming the ray domain. The optical distance between the electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, 101 / 100 . The optical distance between the reflection area in the light emitting layer and the light emitting area in the light emitting layer from which the desired light is obtained is called the optical distance. However, it is possible to change the reflecting area of ​​the first electrode 101 and the emitting area that can obtain the desired light. Since it is difficult to precisely determine the light-emitting region in the optical layer, the first electrode 101 may be arbitrarily selected. The position of the light source is assumed to be the reflection region, and any position on the light-emitting layer where the desired light is obtained is assumed to be the light-emitting region. It is assumed that the above-mentioned effects can be sufficiently obtained.

[0137] The light-emitting element shown in FIG. 1C has a microcavity structure and therefore has the same EL layer. Therefore, it is possible to obtain different emission colors. This eliminates the need for separate coloring (e.g., RGB) for the purpose of achieving high resolution. It is easy to combine with a colored layer (color filter). It is possible to increase the emission intensity in the front direction of a fixed wavelength, which leads to lower power consumption. can.

[0138] The light-emitting element shown in FIG. 1E is an example of the light-emitting element having the tandem structure shown in FIG. 1B. As shown in the figure, three EL layers (103a, 103b, 103c) are disposed on the charge generating layer (10 The three EL layers (103a, 104a, 104b) are sandwiched between the EL layers. Each of the light-emitting layers (113a, 113b, 113c) has a light-emitting layer (113a, 113b, 113c). Therefore, the emission colors of the light emitting layers can be freely combined. The light-emitting layer 113b is red, green, or yellow, and the light-emitting layer 113c is blue. However, the light-emitting layer 113a can be red, and the light-emitting layer 113b can be blue, green, or yellow. Either of the light-emitting layers 113c may be red.

[0139] In the light-emitting element according to one embodiment of the present invention, the first electrode 101 and the second electrode At least one of the electrodes 102 is a light-transmitting electrode (transparent electrode, semi-transmitting / semi-reflective electrode, etc.). When the electrode having light transmission is a transparent electrode, the visible light transmittance of the transparent electrode shall be 40% or more. In the case of a semi-transmissive / semi-reflective electrode, the visible light reflectance of the semi-transmissive / semi-reflective electrode is The ratio is 20% or more and 80% or less, preferably 40% or more and 70% or less. , resistivity is 1×10 -2 It is preferable to set it to Ωcm or less.

[0140] In the above-described light-emitting element which is one embodiment of the present invention, the first electrode 101 and the second electrode When one of the electrodes 102 is a reflective electrode, the possibility of the reflective electrode The reflectance of visible light is set to 40% or more and 100% or less, and preferably 70% or more and 100% or less. In addition, this electrode has a resistivity of 1×10 -2 It is preferable to set it to Ωcm or less.

[0141] <Specific structure and manufacturing method of light-emitting element> Next, a specific structure and a manufacturing method of a light-emitting element according to one embodiment of the present invention will be described with reference to FIG. In this example, the tandem structure shown in FIG. 1(B) is used. A light-emitting device having a T-structure will also be described with reference to FIG. 1(D). When the optical element has a microcavity structure, the first electrode 101 is formed as a reflective electrode. The second electrode 102 is formed as a semi-transmissive and semi-reflective electrode. The second electrode 1 may be formed as a single layer or a multilayer structure using one or more of the above. After the EL layer 103b is formed, the material is selected in the same manner as above and the EL layer 103b is formed. These electrodes can be fabricated by sputtering or vacuum deposition.

[0142] <First Electrode and Second Electrode> The materials for forming the first electrode 101 and the second electrode 102 are selected from those having the above-mentioned functions of both electrodes. If the requirements are met, the following materials can be used in combination. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used appropriately. Specifically, In-Sn oxide (also called ITO), In-Si-Sn oxide (IT SO), In-Zn oxide, and In-W-Zn oxide. 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 Tin (W), palladium (Pd), gold (Au), platinum (Pt), silver (Ag), yttrium The material used is alloys containing metals such as yttrium (Y), neodymium (Nd), and other suitable combinations. In addition, elements belonging to Group 1 or 2 of the periodic table that are not listed above may be used. Elements (e.g., lithium (Li), cesium (Cs), calcium (Ca), strontium (Sr) Rare earth metals such as strontium (Sr), europium (Eu), and ytterbium (Yb) An alloy containing these in appropriate combination, graphene, etc. may also be used.

[0143] In the light-emitting element shown in FIG. 1D, when the first electrode 101 is an anode, The hole injection layer 111a and the hole transport layer 112a of the EL layer 103a are formed on the substrate 101 by vacuum deposition. After the EL layer 103a and the charge generating layer 104 are formed, On the generating layer 104, a hole injection layer 111b and a hole transport layer 112b of the EL layer 103b are formed in the same manner. are successively laminated.

[0144] <Hole injection layer and hole transport layer> The hole injection layer (111, 111a, 111b) is connected to the first electrode 101 which is an anode and the charge generating A layer that injects holes from the layer (104) into the EL layers (103, 103a, 103b). and is a layer containing a material with high hole injection properties.

[0145] Materials with high hole injection properties include molybdenum oxide, vanadium oxide, and ruthenium oxide. Examples of transition metal oxides include oxides of tungsten, manganese, and other oxides. Phthalocyanine (abbreviation: HPc) and copper phthalocyanine (abbreviation: CuPC) The nin-series compound, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl N,N'-bis{4-[bis(3-methylphenyl)amino]biphenyl (abbreviation: DPAB), phenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4, Aromatic amine compounds such as 4'-diamine (abbreviation: DNTPD) or poly(3,4-ene Poly(ethylenedioxythiophene) / poly(styrenesulfonic acid) (abbreviation: PEDOT / PSS ) and other polymers can be used.

[0146] In addition, materials with high hole injection properties include hole transport materials and acceptor materials (electron acceptors). A composite material containing an acceptor material can also be used. In this case, the positive Electrons are extracted from the hole transport material and holes are transported in the hole injection layer (111, 111a, 111b). are generated and are transported through the hole transport layers (112, 112a, 112b) to the light emitting layers (113, 113 Holes are injected into the hole injection layers (111, 111a, 111b). The single-layered semiconductor device is made of a composite material containing a hole transport material and an acceptor material (electron acceptor material). Alternatively, a hole transport material and an acceptor material (electron accepting material) may be formed in layers. Each of these layers may be formed by laminating different layers.

[0147] The hole transport layer (112, 112a, 112b) is b) transfers holes injected from the first electrode 101 or the charge generating layer (104) to the light emitting layer ( 113, 113a, 113b). The hole transport layer (112, 112a, 112b) is a layer containing a hole transport material. The hole transporting material used in the hole injection layer (111, 111a, 111b) is particularly It is preferable to use one having a HOMO level that is the same as or close to the HOMO level.

[0148] The acceptor material used in the hole injection layer (111, 111a, 111b) is an element Oxides of metals belonging to Groups 4 to 8 of the periodic table can be used. are molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, tantalum oxide. Among them, molybdenum oxide is particularly It is preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. The organic acceptors, such as chloranil derivatives and hexaazatriphenylene derivatives, Specifically, 7,7,8,8-tetracyano-2,3,5,6-tetracyano Trafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,1 0,11-Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation In particular, HAT-CN, which contains multiple heteroatoms, can be used. Compounds having a condensed aromatic ring to which an electron-withdrawing group is bonded are preferred because they are thermally stable. In addition, the radicals [3] contain electron-withdrawing groups (especially halogen groups such as fluoro groups and cyano groups). The olefin derivatives are preferred because they have a very high electron-accepting property. ,2,3-Cyclopropanetriylidenetris[4-cyano-2,3,5,6-tetrafluoroethylene] Fluorobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropane trihydrate Ylidene tris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl) Benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylidene [2,3,4,5,6-pentafluorobenzeneacetonitrile] and can be.

[0149] The hole injection layer (111, 111a, 111b) and the hole transport layer (112, 112a, 11 As the hole transport material used in 2b), 10 -6 cm 2 / Vs or higher hole mobility In addition, other materials that have a higher hole transporting property than an electron transporting property are also usable. can be used.

[0150] As hole transport materials, π-electron-rich heteroaromatic compounds (e.g., carbazole derivatives, Indole derivatives) and aromatic amine compounds are preferred. Specific examples include 4,4'-bis [N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-N PD), 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: BSP B) 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) PCBBi1BP, 4-(1-naphthyl)-4'-(9-phenyl) (phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-Di(1-naphthyl)-4''-(9-phenyl-9H-carbazole-3-yl) PCBNBB, 9,9-dimethyl-N-phenyl-N -[4-(9-phenyl-9H-carbazol-3-yl)phenyl]fluorene-2- Amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H-carba 9,9'-bifluoren-2-amine (abbreviation: P CBASF), 4,4',4''-tris(carbazol-9-yl)triphenylamine TCTA, 4,4',4''-tris(N,N-diphenylamino)triphenylphosphine phenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl Aromatic compounds such as [Nyl]-N-phenylamino]triphenylamine (abbreviation: MTDATA) A compound with an amine skeleton, 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-phenyl 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-phenyl Phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4-(N-carbazole 9-[4-(10-phenyl-9-azolyl)phenyl]benzene (abbreviation: TCPB), Carbazoles such as [9H-carbazole]-9H-phenyl-(abbreviation: CzPA) Compounds with the skeleton, 4,4',4''-(benzene-1,3,5-triyl)tri(di Benzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9 -phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DB TFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl Thiophenes such as [1-phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Compounds with the skeleton, 4,4',4''-(benzene-1,3,5-triyl)tri(di Benzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H- Fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLB i-II) and other compounds having a furan skeleton.

[0151] In addition, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylphosphine) nylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl Amino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide]( abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis (phenyl)benzidine (abbreviation: Poly-TPD) and other polymer compounds. It is also possible.

[0152] However, the hole transport material is not limited to the above, and one or more of various known materials may be used. In combination, the hole injection layer (111, 111a, 111b) and the hole transport layer (111, 111a, 111b) serve as hole transport materials. It can be used for the hole transport layer (112, 112a, 112b). Each of the layers 112, 112a, and 112b may be formed of multiple layers. For example, a first hole transport layer and a second hole transport layer may be laminated.

[0153] In the light-emitting element shown in FIG. 1D, a light-emitting layer 112 is formed on the hole transport layer 112a of the EL layer 103a. The EL layer 103a and the charge generating layer 104 are formed by vacuum deposition. After the formation of the hole transport layer 112b of the EL layer 103b, a light emitting layer 113b is formed on the hole transport layer 112b of the EL layer 103b by vacuum deposition. It is formed by:

[0154] <Light-emitting layer> The light-emitting layers (113, 113a, 113b, 113c) are layers containing a light-emitting substance. Luminescent materials include blue, purple, blue-purple, green, yellow-green, yellow, orange, and red. In addition, a material exhibiting different properties is appropriately used for the light-emitting layers (113a, 113b, 113c). By using luminescent materials having different luminescent colors (for example, It is possible to obtain white light by combining different luminescent colors. A laminated structure having different light emitting materials may also be used.

[0155] The light-emitting layers (113, 113a, 113b, 113c) contain a light-emitting material (guest material). In addition, one or more organic compounds (host material, assist material) may be included. In addition, the one or more organic compounds may be a hole-transporting compound described in this embodiment. Either or both of a conductive material and an electron transporting material can be used.

[0156] As a luminescent material that can be used in the luminescent layer (113, 113a, 113b, 113c), are luminescent materials that convert singlet excitation energy into visible light, or triplet excitation energy Luminescent materials can be used that convert energy into light in the visible range.

[0157] Examples of other light-emitting substances include the following:

[0158] Luminescent materials that convert singlet excitation energy into light include fluorescent materials. Examples of such derivatives include pyrene derivatives, anthracene derivatives, triphenylene derivatives, and fluoro derivatives. Oleno derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives In particular, pyrene derivatives are The photon yield is high, which is preferable. Specific examples of pyrene derivatives include N,N'-bis(3- Methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl (dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviation Name: 1,6FrAPrn), N,N'-bis(dibenzothiophene-2-yl)-N,N '-Diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( Pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura N,N'-(pyrene-1,6-diamine) (abbreviation: 1,6BnfAPrn), yl)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[ (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (abbreviation :1,6BnfAPrn-03).

[0159] In addition, 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2, 2'-Bipyridine (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl- 9-Anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-cal 4'-(10-phenyl-9-anthryl)-4'-(10-phenyl-9-benzol-9-yl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl Phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo PCAPA, 4-(10-phenyl-9-anthryl)-4 '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BAPA), 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9- Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA) ), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP ), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1- phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviation Name: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-phenyl] N-(2-phenyl)-9H-carbazol-3-amine (abbreviation: 2PCAPPA), -[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA) etc. can be used. do.

[0160] In addition, examples of luminescent materials that convert triplet excitation energy into luminescence include phosphorescent materials. Materials that exhibit thermally activated delayed fluorescence (thermally activated delayed fluorescence) tivated delayed fluorescence (TADF) materials are can be.

[0161] Phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. Since each substance has a different emission color (emission peak), it is necessary to select the appropriate one as needed. Select and use.

[0162] Blue or green, with a peak wavelength of 450 nm or more and 570 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0163] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrPrp tz-3b)3])tris[3-(5-biphenyl)-5-isopropyl-4-phenyl -4H-1,2,4-triazolato]iridium(III) (abbreviation: Ir(iPr5bt z)3]), organometallic complexes having a 4H-triazole skeleton such as tris[3-methyl 1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolato Iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), tris(1-methyl- 5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir(Prptz1-Me)3]) Organometallic complex, fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl [Ir(iPrpmi)3]iridium(III) , tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]phenyl [Nanthridinato]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3]) Organometallic complexes having an imidazole skeleton such as bis[2-(4',6'-difluoro Phenyl)pyridinato-N,C 2’ ]Iridium(III) tetrakis(1-pyrazolyl) ) borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridin Nat-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpic), bis{ 2-[3',5'-Bis(trifluoromethyl)phenyl]pyridinato-N,C 2’}stomach Ir(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), S[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]Iridium (I II) Acetylacetonate (abbreviation: FIr(acac)) has an electron-withdrawing group Examples of the organic metal complex include those having a phenylpyridine derivative as a ligand.

[0164] It has a green or yellow color and the peak wavelength of the emission spectrum is between 495 nm and 590 nm. Some phosphorescent materials include the following:

[0165] For example, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)i Lithium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bi Bis(6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4 -phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(a cac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(nbppm)2(acac)]) , (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl Rupyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac) ]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl phenyl)-4-pyrimidinyl-κN3]phenyl-κC}iridium(III) (abbreviation :[Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( Organometallic iridium complexes with pyrimidine skeletons such as (acetylated acac)] cetonato)bis(3,5-dimethyl-2-phenylpyrazinate)iridium(III)( Abbreviation: [Ir(mppr-Me)2(acac)]), (acetylacetonato)bis(5 -isopropyl-3-methyl-2-phenylpyrazinate)iridium(III)(abbreviation: Organometallic compounds with pyrazine skeletons such as [Ir(mppr-iPr)2(acac)] Iridium complex, tris(2-phenylpyridinato-N,C 2’) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2-phenylpyridinato-N,C 2’ ) Iridi Ir(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), (benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: [I r(bzq)2(acac)]), tris(benzo[h]quinolinato)iridium(II I) (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(a cac)]), [2-(4-phenyl-2-pyridinyl-κN)phenyl-κC]bis[ 2-(2-pyridinyl-κN)phenyl-κC]iridium(III) (abbreviation: [Ir( ppy)2(4dppy)]), bis[2-(2-pyridinyl-κN)phenyl-κC] [2-(4-methyl-5-phenyl-2-pyridinyl-κN)phenyl-κC] An organometallic iridium complex with a pyridine skeleton, bis(2,4-diphenyl-1,3-phenyl) Xazolato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir( dpo)2(acac)]), bis{2-[4'-(perfluorophenyl)phenyl] Pyridinate-N,C 2’}Iridium(III) acetylacetonate (abbreviation: [Ir( p-PF-ph)2(acac)]), bis(2-phenylbenzothiazolato-N,C 2 ’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(bt)2(acac) ]), as well as tris(acetylacetonato)(monophenanthroline) Rare earth metals such as terbium(III) (abbreviation: [Tb(acac)3(Phen)]) Examples include complexes of the aryl group.

[0166] Yellow or red, with a peak wavelength of 570 nm or more and 750 nm or less in the emission spectrum. Some phosphorescent materials include the following:

[0167] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinium] dinato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), S[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di (Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) ) (abbreviation: [Ir(d1npm)2(dpm)]) Metal Complex, (acetylacetonato)bis(2,3,5-triphenylpyrazinate)iridide Ir(tppr)2(acac)], bis(2,3,5-trimethylammonium bromide) Triphenylpyrazinate)(dipivaloylmethanato)iridium(III) (abbreviation: [Ir (tppr)2(dpm)]), bis{4,6-dimethyl-2-[3-(3,5-dimethyl {5-phenyl-2-pyrazinyl-κN}phenyl-κC}(2,6-diphenyl Tyl-3,5-heptanedionate-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-pyrazine {2,2,6,6-tetramethyl-3,5-heptanedioic acid} Nat-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-dmCP) 2(dpm)]), (acetylacetonato)bis[2-methyl-3-phenylquinoxalyl Nat-N,C 2’ ]Iridium(III) (abbreviation: [Ir(mpq)2(acac)]) , (acetylacetonato)bis(2,3-diphenylquinoxalinato-N,C 2’ ) Ili Ir(dpq)2(acac) ) Bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]) Complexes and tris(1-phenylisoquinolinato-N,C 2’ ) Iridium (III) (abbreviation Name: [Ir(piq)3]), Bis(1-phenylisoquinolinato-N,C 2’ ) Iridi Ir(III) acetylacetonate (abbreviation: [Ir(piq)2(acac)]), Su[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl-κC](2,4-pentanedione Tandione-κ 2 O,O') Iridium(III) and other organic compounds with pyridine skeletons Metal complex, 2,3,7,8,12,13,17,18-octaethyl-21H,23H- Platinum complexes such as porphyrin platinum(II) (abbreviation: [PtOEP]), tris(1,3 -Diphenyl-1,3-propanedionato)(monophenanthroline)europium(I II) (abbreviation: [Eu(DBM)3(Phen)]), tris[1-(2-thenoyl)- 3,3,3-Trifluoroacetonato](monophenanthroline)europium(III) ) (abbreviation: [Eu(TTA)3(Phen)]).

[0168] The organic compounds (host materials, The host material has an energy gap larger than that of the light-emitting material (guest material). The light-emitting layer (11) may be made of one or more materials having a gy gap. 3, 113a, 113b, 113c), when multiple organic compounds are used, exciplexes are formed. It is preferable to use a compound having such a property in combination with a phosphorescent material. This allows the transfer of energy from the exciplex to the luminescent material (ExTET). It is possible to obtain light emission using the lex-triplet energy transfer method. In this case, various organic compounds can be used in appropriate combination, but To form an exciplex, a compound that easily accepts holes (hole transport material) and an electron transport material are required. It is particularly preferable to combine the compound with a compound that easily receives electrons (electron transporting material). The organic compound according to one embodiment of the present invention has a low LUMO level and is easy to accept electrons. It is suitable as a mixture.

[0169] When the light-emitting substance is a fluorescent material, the host material has an energy level of 100 nm in the singlet excited state. It is preferable to use an organic compound having a large triplet excited state energy level and a small triplet excited state energy level. For example, it is preferable to use anthracene derivatives or tetracene derivatives. Phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo (abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl- 9H-Carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracene 7-[4-(10-phenyl)phenyl]-9H-carbazole (abbreviation: CzPA), [c,g]carbazole (abbreviation: cg DBCzPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-be Benzo[b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-1 0-{4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}a 5,12-diphenyltetracene (abbreviation: FLPPA), 5,12-diphenyltetracene, 5,12-bis( (biphenyl-2-yl)tetracene.

[0170] When the light-emitting material is a phosphorescent material, the host material is a material that has a triplet excitation energy of the light-emitting material. (energy difference between the ground state and the triplet excited state) In this case, in addition to zinc and aluminum-based metal complexes, Oxadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline Dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives Conductors, pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthroline In addition to anthroline derivatives, aromatic amines and carbazole derivatives can be used. .

[0171] More specifically, the host material may be, for example, the following hole transporting material and electron transporting material: can be used.

[0172] An example of a host material with high hole transporting properties is 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), 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino]be Examples of aromatic amine compounds include benzene (abbreviation: DPA3B).

[0173] Also, 3-[N-(4-diphenylaminophenyl)-N-phenylamino]-9-phenyl Nylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4-diphenylamine PCzDPA 2), 3,6-bis[N-(4-diphenylaminophenyl)-N-(1-naphthyl)a 3-[N-(9-phenylamino)-9-phenylcarbazole (abbreviation: PCzTPN2), [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-phenyl Examples of the carbazole derivatives include PCzPCN1 and PCzPCN2. Another example of a carbazole derivative is 4,4'-di(N-carbazolyl)biphene. Nyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)phenyl]benzoyl Zene (abbreviation: TCPB), 1,4-bis[4-(N-carbazolyl)phenyl]-2,3 , 5,6-tetraphenylbenzene, etc. can also be used.

[0174] In addition, examples of host materials with high hole transport properties include 4,4'-bis[N-(1-naphthalene) (abbreviation: NPB or α-NPD) and N,N' -Bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4 ,4'-diamine (abbreviation: TPD), 4,4',4''-tris(carbazole-9-yl) N-(1-phenyl)triphenylamine (TCTA), 1-TNATA, 4,4 ',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDAT A) 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 Name: BPAFLP), 4-phenyl-3'-(9-phenylfluoren-9-yl)trifluoromethyl Phenylamine (abbreviation: mBPAFLP), N-(9,9-dimethyl-9H-fluorene -2-yl)-N-{9,9-dimethyl-2-[N'-phenyl-N'-(9,9-dimethyl (ethyl-9H-fluoren-2-yl)amino]-9H-fluoren-7-yl}phenyl Amine (abbreviation: DFLADFL), N-(9,9-dimethyl-2-diphenylamino-9 H-fluoren-7-yl)diphenylamine (abbreviation: DPNF), 2-[N-(4-diphenyl phenylaminophenyl)-N-phenylamino]spiro-9,9'-bifluorene (abbreviation Name: DPASF), 4-phenyl-4'-(9-phenyl-9H-carbazole-3-yl (III)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-( 9-Phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBBi) 1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl 4,4'-di(1-naphthyl)-4' '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BNBB), 4-phenyldiphenyl-(9-phenyl-9H-carbazol-3-yl )amine (abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazole-3-isopropyl) N,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N ',N''-Triphenyl-N,N',N''-tris(9-phenylcarbazole-3 -yl)benzene-1,3,5-triamine (abbreviation: PCA3B), N-(4-biphenyl -N-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H- Carbazole-3-amine (abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl) 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 ]fluorene-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl Nyl-9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-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), N,N '-Bis[4-(carbazol-9-yl)phenyl]-N,N'-diphenyl-9,9 -Dimethylfluorene-2,7-diamine (abbreviation: YGA2F) and other aromatic amine compounds Also usable are 3-[4-(1-naphthyl)-phenyl]-9-phenyl. 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-carbazo mCP, 3,6-bis(3,5-diphenylphenyl)-9- Phenylcarbazole (abbreviation: CzTP), 4-{3-[3-(9-phenyl-9H- mmDBFFLBi -II), 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) DBF3P-II, 1,3,5-tri(dibenzothiophene-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), 4-[3-(triphenyl mDBTPTp-II, etc. benzol compounds, thiophene compounds, furan compounds, fluorene compounds, triphenylene Compounds, phenanthrene compounds, etc. can be used.

[0175] As a host material having a high electron transporting property, for example, tris(8-quinolinolato)aluminum Aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum Alm(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato) Beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4 -phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinyl Zinc(II) (abbreviation: Znq) and other quinoline or benzoquinoline skeletons In addition, there are metal complexes having bis[2-(2-benzoxazolyl)phenol]. [2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnPBO) Zinc(II) (abbreviation: ZnBTZ) and other oxazole and thiazole ligands Metal complexes that can be used include those that can be used with 2-(4-biphenyl) (4-tert-butylphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation (PBD) and 1,3-bis[5-(p-tert-butylphenyl)-1,3,4- Oxadiazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl 1,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation Oxadiazole derivatives such as 3-(4-biphenylyl)-4-phenylene oxide and Nyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TA Z) and 2,2',2''-(1,3,5-benzenetriazole derivatives. Tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2-[3 -(Dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-benzimidazo Compounds with imidazole skeletons, such as BETA-II (abbreviation: mDBTBIm-II), benzoimidazole derivatives) and 4,4'-bis(5-methylbenzoxazole-2-iso Compounds with an oxazole skeleton, such as benzoylstilbene (abbreviation: BzOS) Oxazole derivatives), bathophenanthroline (abbreviation: Bphen), bathocuproin BCP, 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1 ,10-phenanthroline (NBphen) and other phenanthroline derivatives, -[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]dibenzyl Benzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq), 2-[4-(3,6-difluorophenyl) (phenyl-9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline ( Abbreviation: 2CzPDBq-III), 7-[3-(dibenzothiophen-4-yl)phenyl 1,2-Dibenzo[f,h]quinoxaline (abbreviation: 7mDBTPDBq-II), and 6-[ 3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation Name: 6mDBTPDBq-II), 4,6-bis[3-(phenanthren-9-yl)phenyl] phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-diphenyl 4,6-zothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), Bis[3-(9H-carbazol-9-yl)phenyl]pyrimidine (abbreviation: 4,6mC Heterocyclic compounds with diazine skeletons such as 2-{4-[3-(N-phenyl 9H-carbazol-3-yl)-9H-carbazol-9-yl]phenyl}- Triazines such as 4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzPTzn) Heterocyclic compounds with an aryl skeleton and 3,5-bis[3-(9H-carbazol-9-yl] )phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl Heterocyclization of pyridine skeletons such as TmPyPB Compounds such as poly(2,5-pyridinediyl) (abbreviation: PPy) and Poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5 -diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7- PF-BPy ) can also be used.

[0176] In addition, examples of the host material include anthracene derivatives, phenanthrene derivatives, pyrene derivatives, Condensed polycyclic aromatic compounds such as chrysene derivatives and dibenzo[g,p]chrysene derivatives are included. Specifically, 9,10-diphenylanthracene (abbreviation: DPAnth), N,N- Diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carba CzA1PA, 4-(10-phenyl-9-anthryl) Triphenylamine (abbreviation: DPhPA), YGAPA, PCAPA, N,9-diphenyl -N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H -Carbazole-3-amine (abbreviation: PCAPBA) 2PCAPA, 6,12-dimethoxy 5,11-diphenylchrysene, DBC1, 9-[4-(10-phenyl-9-an 3,6-diphenyl)-9H-carbazole (abbreviation: CzPA), -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 (DNA), 2-t ert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA) , 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-di 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS), Diphenanthrene (abbreviation: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3) can be used.

[0177] In addition, when a plurality of organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c), Two types of compounds (a first compound and a second compound) that form an exciplex, and an organometallic In this case, various organic compounds may be used in appropriate combination. However, in order to efficiently form an exciplex, a compound that easily accepts holes ( A compound that easily accepts electrons (a hole-transporting material) is combined with a compound that easily accepts electrons (an electron-transporting material). Specific examples of the hole transport material and the electron transport material are as follows: The materials shown in this embodiment mode can be used. This structure provides high efficiency, low voltage, and long life. You can achieve both lives at the same time.

[0178] TADF materials are materials that convert triplet excited states into singlet excited states using a small amount of thermal energy. It is possible to convert the light into a singlet state (reverse intersystem crossing), and efficiently emit light (fluorescence) from the singlet excited state. The conditions for efficiently obtaining thermally activated delayed fluorescence are as follows: The energy difference between the doublet excitation level and the singlet excitation level is 0 eV or more and 0.2 eV or less, preferably In addition, the delayed fluorescence in TADF materials is The light is an emission that has a spectrum similar to that of normal fluorescence, but has a significantly longer lifespan. The lifespan of -6 seconds or more, preferably 10 -3 More than seconds.

[0179] Examples of TADF materials include fullerenes and their derivatives, and acridines such as proflavine. Derivatives, eosin, etc. Also, magnesium (Mg), zinc (Zn), cadmium (Cd) Cd, Sn, Pt, In, or Palladium Examples of metal-containing porphyrins include those containing Pd. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2(Proto IX)) , mesoporphyrin-tin fluoride complex (abbreviation: SnF2(Meso IX)), hematopoietin Lufirin-Tin Fluoride Complex (abbreviation: SnF2 (Hemato IX)), Coproporf Fluorine tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me), Octaethylporphyrin-Tin Fluoride Complex (abbreviation: SnF2(OEP)) , etioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), octaethylene Examples include thylporphyrin-platinum chloride complex (abbreviation: PtCl2OEP).

[0180] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenylindolo[ 2,3-a]carbazol-11-yl)-1,3,5-triazine (abbreviation: PIC-T RZ), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl 4,6-diphenyl-1,3,5-triazine (abbreviation Name: 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-di Methyl-9H-acridin-10-yl)-9H-xanthen-9-one (abbreviation: ACR XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a Clidine-9,9'-anthracene]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having an excess type heteroaromatic ring and a π-electron deficient type heteroaromatic ring can be used. In addition, a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded is The donor properties of π-electron-rich heteroaromatic rings and the acceptor properties of π-electron-deficient heteroaromatic rings are both strong. This is particularly preferred because it reduces the energy difference between the singlet excited state and the triplet excited state. stomach.

[0181] In addition, when using a TADF material, it can also be used in combination with other organic compounds.

[0182] In the light-emitting device shown in FIG. 1D, an electron transport layer is provided on the light-emitting layer 113a of the EL layer 103a. The EL layer 103a and the charge generating layer 104 are formed by vacuum deposition. After the formation of the electron transport layer 114b, the electron transport layer 114b is formed on the light emitting layer 113b of the EL layer 103b by vacuum deposition. It is formed by:

[0183] <Electron transport layer> The electron transport layer (114, 114a, 114b) is b) converts the electrons injected from the second electrode 102 or the charge generating layer (104) into the light emitting layer ( 113, 113a, 113b). The electron transport layer (114, 114a, 114b) is a layer containing an electron transport material. The electron transport material used in 14b) is 1×10 -6 cm 2 / Vs or higher electron mobility In addition, other materials that have a higher electron transporting property than a hole transporting property are also usable. can be used.

[0184] Electron transport materials include quinoline ligands, benzoquinoline ligands, and oxazole ligands. or a metal complex having a thiazole ligand, an oxadiazole derivative, or a triazole derivatives, phenanthroline derivatives, pyridine derivatives, bipyridine derivatives, etc. In addition, the use of π-electron-deficient heteroaromatic compounds such as nitrogen-containing heteroaromatic compounds It is also possible.

[0185] Specifically, Alq3, tris(4-methyl-8-quinolinolato)aluminum (III ) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (II) (abbreviation: BeBq2), BAlq, bis[2-(2-hydroxyphenyl)benzene 2-(2-hydroxy-1,3-dimethyl-2-oxazolato)zinc(II) (abbreviation: Zn(BOX)2), Metal complexes such as [diphenyl]benzothiazolato]zinc(II) (abbreviation: Zn(BTZ)2) 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4- Oxadiazole (abbreviation: PBD), OXD-7, 3-(4'-tert-butylphenyl (4''-biphenyl)-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), Bathophen Anthroline (abbreviation: Bphen), Bathocuproine (abbreviation: BCP), 4,4'-Bis(4,4'-biphenyl) Complexes such as bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOS) The aromatic compound, 2-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f ,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(dibenzothio 2-phenyl-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: mDBTBPDBq-II), 2-[4-(3,6-diphenyl-9H-carbazole- 9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III ), 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoki Sarin (abbreviation: 7mDBTPDBq-II), 6-[3-(dibenzothiophene-4-yl) 6mDBTPDBq-II, etc. The quinoxaline or dibenzoquinoxaline derivatives of the above formula can be used.

[0186] In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl Fluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF- Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2' -bipyridine-6,6'-diyl) (abbreviation: PF-BPy) You can also be there.

[0187] In addition, the electron transport layer (114, 114a, 114b) may be a single layer or may be made of the above-mentioned material. The layer may have a structure in which two or more layers made of the above are laminated.

[0188] In the light-emitting element shown in FIG. 1D, electrons are injected onto the electron transport layer 114a of the EL layer 103a. The charge generating layer 115a is formed by vacuum deposition. Then, the EL layer 103a and the charge generating layer 115b are After the electron transport layer 114b of the EL layer 103b is formed, the electron injection layer 104 is formed. The insulating layer 115b is formed by vacuum deposition.

[0189] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing a substance with high electron injection properties. The electron injection layers (115, 115a, 115b) are made of lithium fluoride (LiF), cerium fluoride (CeF), CsF, Calcium Fluoride (CaF2), Lithium Oxide (LiO x ) etc. Such alkali metals, alkaline earth metals, or compounds thereof can be used. In addition, rare earth metal compounds such as erbium fluoride (ErF3) can be used. In addition, an electride may be used for the electron injection layer (115, 115a, 115b). For example, a mixed oxide of calcium and aluminum with high electron doping is used as a tritride. In addition, the above-mentioned electron transport layer (114, 114a, 114b) It is also possible to use a substance constituting the above.

[0190] In addition, the electron injection layer (115, 115a, 115b) contains an organic compound and an electron donor (donor A composite material containing the above-mentioned compound may be used. Since electrons are generated in the organic compound, the organic compound has excellent electron injection and transport properties. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons. Specifically, for example, the electron transporting layer (114, 114a, 114b) described above may be used Materials such as metal complexes and heteroaromatic compounds can be used as electron donors. Any substance that exhibits electron donating properties to organic compounds is acceptable. The lithium earth metals and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, Erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metals Metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like. Alternatively, a Lewis base such as magnesium oxide can be used. Organic compounds such as thiafulvalene (abbreviation: TTF) can also be used.

[0191] For example, when the light obtained from the light emitting layer 113b is to be amplified, the second electrode 102 The optical distance between the light emitting layer 113b and the light emitting layer 113b is less than λ / 4 with respect to the wavelength of the light emitted by the light emitting layer 113b. In this case, it is preferable to form the electron transport layer 114b or the electron injection layer 114c so that the electron transport layer 114b is filled with the electron This can be adjusted by changing the film thickness of 115b.

[0192] <Charge generation layer> The charge generating layer 104 generates a charge between the first electrode (anode) 101 and the second electrode (cathode) 102. When pressure is applied, electrons are injected into the EL layer 103a and holes are injected into the EL layer 103b. The charge generation layer 104 has a function of forming a hole transporting material with an electron acceptor (acceptor ) is added to the electron transport material, Alternatively, both of these configurations may be laminated. By forming the charge generating layer 104 using the material, when the EL layer is laminated, The increase in driving voltage can be suppressed.

[0193] In the case where the charge generating layer 104 is configured such that an electron acceptor is added to a hole transporting material, As the hole transporting material, the material shown in this embodiment mode can be used. The receptor is 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinoline. Examples include dimethane (abbreviation: F4-TCNQ), chloranil, etc. Examples of the oxides of metals belonging to Groups 4 to 8 in the table include: Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide Examples of the oxide include tin, manganese oxide, and rhenium oxide.

[0194] In the case where the charge generating layer 104 has a structure in which an electron donor is added to an electron transporting material, As the electron transporting material, the materials shown in this embodiment mode can be used. The donor may be an alkali metal, an alkaline earth metal, a rare earth metal, or an element of the periodic table. Metals belonging to Groups 2 and 13 in the table and their oxides and carbonates can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium Ca, Yb, In, Lithium oxide, Cesium carbonate It is preferable to use organic compounds such as tetrathianaphthalene. It may also be used as a donor.

[0195] The EL layer 103c in FIG. 1(E) is the same as the EL layer (103, 103a, 103b) described above. The charge generating layers 104a and 104b may have the same structure as described above. The charge generating layer 104 may have a similar structure.

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

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

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

[0199] The EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are Each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a , 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114 , 114a, 114b), the electron injection layer (115, 115a, 115b) and the charge generation layer (1 04, 104a, 104b) are not limited to the above-mentioned materials and may be other materials. However, as long as the functions of each layer can be fulfilled, they can be used in combination. The following compounds are considered to be suitable for use: high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (low molecular weight compounds, Compounds in the intermediate range between polymers and molecules: molecular weight 400-4000), inorganic compounds (quantum dot materials As the quantum dot material, colloidal quantum dots can be used. Materials, alloy-type quantum dot materials, core-shell-type quantum dot materials, core-type quantum dot materials, etc. etc. can be used.

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

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

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

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

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

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

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

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

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

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

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

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

[0212] 3A is a top view showing the light emitting device, and FIG. 3B is a top view showing the light emitting device along the dashed line AA in FIG. The active matrix type light emitting device has a first substrate 301 and a second substrate 302. A pixel portion 302, a driver circuit portion (source line driver circuit) 303, and a driver circuit portion (gate The pixel section 302 and the driver circuit section (304a, 304b) are connected to the pixel section 302. The first substrate 301 and the second substrate 302 are connected by a seal material 305. It is sealed between the plate 306 .

[0213] Moreover, on the first substrate 301, a lead wiring 307 is provided. The external input terminal is connected to the FPC 308. The FPC 308 is a drive circuit section. (303, 304a, 304b) receive external signals (e.g., video signals, clock signals , start signal, reset signal, etc.) and electric potential. A printed wiring board (PWB) may be attached. Note that if these FPCs or PWBs are installed, The attached state is included in the light emitting device.

[0214] Next, a cross-sectional structure is shown in FIG.

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

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

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

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

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

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

[0221] An EL layer 315 and a second electrode 316 are stacked on the first electrode 313. 315 is a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. Yes.

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

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

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

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

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

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

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

[0229] (Embodiment 5) In this embodiment, a light-emitting device according to one embodiment of the present invention and a light-emitting element according to one embodiment of the present invention will be described. Examples of various electronic devices and automobiles completed using the display device will be described below.

[0230] The electronic device shown in FIG. 4(A) to FIG. 4(E) includes a housing 7000, a display unit 7001, and a speaker 7002. 003, LED lamp 7004, operation key 7005 (power switch or operation switch ), a connection terminal 7006, a sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity, Rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, Includes functions to measure power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared rays ), microphone 7008, etc.

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

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

[0233] FIG. 4C shows a goggle-type display. In addition to the above, a second display unit 7002 , a support 7012, an earphone 7013, etc.

[0234] FIG. 4(D) shows a digital camera with a television receiving function, which, in addition to the above, has an antenna 7014, a shutter button 7015, an image receiving unit 7016, etc.

[0235] FIG. 4E shows a mobile phone (including a smartphone), and a display unit 70 is provided in a housing 7000. 01, microphone 7019, speaker 7003, camera 7020, external connection part 702 1, operation buttons 7022, etc.

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

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

[0238] FIG. 4G shows a smart watch, which includes a housing 7000, a display unit 7001, and operation buttons. 7022, 7023, a connection terminal 7024, a band 7025, a clasp 7026, etc. .

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

[0240] The smartwatch shown in FIG. 4G can have various functions. For example, , the function to display various information (still images, videos, text images, etc.) on the display unit, Functions such as displaying calendars, dates, or times, and various software (programs) The function of controlling processing by the wireless communication function, It has a function to connect to a data network, and a wireless communication function to transmit or receive various data. The function of reading out the program or data recorded on the recording medium and displaying it on the display unit. It may have the function of

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

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

[0243] In addition, as an electronic device to which a light-emitting device is applied, a folding type as shown in Figs. 5A shows a portable information terminal 931 in an unfolded state. 0. Also, FIG. 5(B) shows the state of the unfolded or folded state. The mobile information terminal 9310 is shown in a state in the middle of changing. The portable information terminal 9310 is in a folded state. The FOMA terminal is highly portable, and when unfolded, it has a seamless, wide display area that provides excellent visibility of the display. can be.

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

[0245] In addition, an automobile to which a light emitting device is applied is shown in FIG. The device can be integrated with the automobile. Outer lights 5101 (including the rear of the vehicle), tire wheels 5102, doors 5103 It can be applied to a part or the whole of the car. A display unit 5104, a handle 5105, a shift lever 5106, a seat 5107, an inner - It can be applied to rear view mirrors 5108, etc. It can also be applied to some glass windows. You may do so.

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

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

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

[0249] 7(A), (B), (C), and (D) show examples of cross-sectional views of a lighting device. (A) and (B) are bottom emission type lighting devices that extract light from the substrate side. C) and (D) are top-emission type lighting devices that extract light from the encapsulation substrate side.

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

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

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

[0253] In addition, instead of the substrate 4003, as in the illumination device 4100 of FIG. 7(B), A diffuser plate 4015 may be provided on the outside.

[0254] A lighting device 4200 in FIG. 7C has a light-emitting element 4202 over a substrate 4201. The element 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206. .

[0255] The first electrode 4204 is electrically connected to the electrode 4207, and the second electrode 4206 is electrically connected to the electrode 4208. 208. The auxiliary wiring 4 is electrically connected to the second electrode 4206. An insulating layer 4210 may be provided under the auxiliary wiring 4209. stomach.

[0256] The substrate 4201 and the sealing substrate 4211 having projections and recesses are bonded with a sealant 4212. In addition, a barrier film 4213 and a planarization film 421 are provided between the sealing substrate 4211 and the light emitting element 4202. 4 may be provided. Note that since the sealing substrate 4211 has projections and recesses as shown in FIG. The extraction efficiency of the light generated by the light emitting element 4202 can be improved.

[0257] In addition, instead of the sealing substrate 4211, a light-emitting element 4 is provided as in a lighting device 4300 of FIG. A diffuser plate 4215 may be provided on top of 202 .

[0258] As described in this embodiment, a light-emitting device according to one embodiment of the present invention or a part thereof By using a light-emitting element having such a characteristic, a lighting device having a desired chromaticity can be provided.

[0259] Note that the structure described in this embodiment mode may be used in appropriate combination with structures described in other embodiment modes. It is possible.

[0260] (Embodiment 7) In this embodiment, a light-emitting device according to one embodiment of the present invention or a light-emitting element which is a part of the light-emitting device is used. An application example of a lighting device manufactured using this will be described with reference to FIG.

[0261] As an indoor lighting device, it can be used as a ceiling light 8001. The 8001 lighting fixture is available in ceiling-mounted and ceiling-embedded types. It is constructed by combining the optical device with a case and a cover. It can also be applied to a ceiling-hanging type (cord hanging type).

[0262] In addition, the footlights 8002 can irradiate the floor surface with light, improving safety at the feet. For example, it is effective to use it in bedrooms, stairs, and corridors. In that case, depending on the size and structure of the room, The size and shape can be changed as needed. It is also possible to configure the lighting device as a stationary type.

[0263] The sheet-like lighting 8003 is a thin sheet-like lighting device. It is attached to a wall surface. Since it uses a small space, it can be used for a wide range of purposes. It can also be used on curved walls or housings.

[0264] It is also possible to use a lighting device 8004 in which light from a light source is controlled to only a desired direction. do.

[0265] In addition to the above, a light-emitting device according to one embodiment of the present invention may be attached to a part of furniture in a room. By applying the light-emitting element that is a part of the device, it becomes a lighting device that also functions as furniture. It is possible.

[0266] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0267] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible. EXAMPLES

[0268] <Synthesis Example 1> In this synthesis example, the organic compound represented by the structural formula (100) in the first embodiment of the present invention is Compound, 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(triphenylene -2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8Tp-4mDBt The synthesis method of 8Tp-4mDBtPBfpm is explained below. is shown below.

[0269] [ka]

[0270] <Synthesis of 8Tp-4mDBtPBfpm> First, 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]be 1.5 g of benzofuro[3,2-d]pyrimidine and 4,4,5,5-tetramethyl-2-( 1.5 g of triphenylene-2-yl)-1,3,2-dioxaborolane and tripotassium phosphate Put 2.7 g of ethanol, 35 mL of diglyme, and 0.93 g of t-butanol into a three-neck flask. The flask was filled with nitrogen, and 15 mg of palladium(II) acetate and di(1-adamantium) Add 47 mg of butyl-n-butylphosphine and heat at 130°C for 6 hours under a nitrogen stream. The reaction mixture was added with water, filtered, and then diluted with water, ethanol, and toluene. The filter was washed.

[0271] Next, the residue was dissolved in boiling toluene and filtered. The solvent was concentrated and recrystallized to obtain the target pale yellow solid (0.52 g, 2.0% yield). The synthesis scheme is shown in formula (a-1) below.

[0272] [ka]

[0273] The resulting pale yellow solid (0.52 g) was purified by train sublimation. The conditions for sublimation purification were: pressure 2.3 Pa, argon gas flow rate 10 mL / min, The solid was heated at 360°C. After purification by sublimation, 0.36g of the desired yellow solid was obtained, with a recovery rate of 69%. I got it at.

[0274] Nuclear magnetic resonance spectroscopy of the resulting yellow solid ( 1 The results of the analysis by H-NMR are shown below. Ta, 1 The H-NMR chart is shown in FIG. 9. From this result, in this example, It was found that the organic compound represented by formula (100), 8Tp-4mDBtPBfpm, was obtained. It was.

[0275] 1H-NMR.δ(TCE-d2):7.44-7.49(m,2H), 7.60-7. 66(m,6H), 7.76-7.79(t,1H), 7.84-7.87(t,2H) , 7.95(d,1H), 7.98(d,1H), 8.15(d,1H), 8.20(d ,2H), 8.63-8.67(m,3H), 8.69-8.76(m,4H), 8.9 3(s,1H), 9.02(s,1H), 9.31(s,1H).

[0276] Next, the absorption and emission spectra of 8Tp-4mDBtPBfpm in toluene solution were The torque is shown in Figure 10(A), where the horizontal axis represents the wavelength and the vertical axis represents the absorption intensity and emission intensity.

[0277] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The absorption spectrum of 8Tp-4mDBtPBfpm in toluene solution was Absorption spectrum obtained by measuring a toluene solution of mDBtPBfpm in a quartz cell The absorption spectrum obtained by measuring toluene in a quartz cell was subtracted from the above. The emission spectrum was measured using a PL-EL measuring device (Hamamatsu Photonics). The emission spectrum of 8Tp-4mDBtPBfpm in toluene solution was A toluene solution of DBtPBfpm was placed in a quartz cell and measured.

[0278] As shown in FIG. 10(A), in the toluene solution of 8Tp-4mDBtPBfpm, the peaks at 283 nm and Absorption peaks were observed around 320 nm and 333 nm, and 409 nm (excitation wavelength: 333 nm ) A peak in the emission wavelength was observed.

[0279] Next, the absorption and emission spectra of the solid thin film of 8Tp-4mDBtPBfpm The solid thin film was prepared on a quartz substrate by vacuum deposition. Torr is the absorbance (-log10 [%T / (10 The absorption spectrum was calculated using the formula: (0-%R) (where %T is the transmittance and %R is the reflectance). A UV-Vis spectrophotometer (U4100, Hitachi High-Technologies Corporation) was used to measure the The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS 920) was used. The absorption and emission spectra of the obtained solid thin film were measured. is shown in Figure 10(B). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0280] From the results of Fig. 10(B), the solid thin film of 8Tp-4mDBtPBfpm has a thickness of 245 nm, Absorption peaks were observed around 270 nm and 319 nm, and 440 nm (excitation wavelength: 330 nm) A peak in the emission wavelength was observed near

[0281] Next, the 8Tp-4mDBtPBfpm obtained in this example was analyzed by liquid chromatography mass spectrometry. (Liquid Chromatography Mass Spectrometry The analysis was performed using LC / MS (abbreviation: LC / MS analysis).

[0282] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30. LC (liquid chromatography) separation was performed using Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fiscal.

[0283] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was appropriately selected as the delivery condition. The sample was prepared by dissolving 8Tp-4mDBtPBfpm at any concentration in an organic solvent. The injection volume was 5.0 μL.

[0284] Targeted-MS 2 The ions derived from 8Tp-4mDBtPBfpm were MS m / z=654.18 2 Measurements were performed using Targeted-MS. 2 The settings are -The mass range of the target ions was m / z = 654.18 ± 2.0 (isolation width The detection was performed in positive mode with the NDOW setting set to 4. The target was detected in the collision cell. The energy that accelerates ions is called Normal Collision Energy (NCE). The measurement was performed with an energy of 70. The obtained MS spectrum is shown in FIG.

[0285] From the results in Figure 11, 8Tp-4mDBtPBfpm mainly has m / z=626 and 591 , 471, 451, 394, 369, 341, 315, 286, 271, 260, 226 It was found that a product ion was detected at around 197. The results shown in Figure 11 Since this shows the characteristic results derived from 8Tp-4mDBtPBfpm, This is important data for identifying 8Tp-4mDBtPBfpm contained in the mixture. It can be said that.

[0286] The product ion at m / z=626 is due to the cleavage of the pyrimidine ring and the loss of the nitrile. The product ion at m / z=394 is assumed to be a cation generated by , which is presumed to be a cation generated by the elimination of 4-phenyldibenzothiophene, and 8Tp- This suggests that 4mDBtPBfpm contains phenyldibenzothiophene. be.

[0287] In addition, the product ion at m / z=197 is a product of the dibenzothiophenyl group being eliminated. It is assumed that the cation formed by the reaction is 8Tp-4mDBtPBfpm, which has a dibenzothiophenyl group. This suggests that it contains EXAMPLES

[0288] <Synthesis Example 2> In this example, an organic compound according to one embodiment of the present invention is described. 1), 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(9, 9-Dimethylfluoren-2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation The synthesis method of 8FL-4mDBtPBfpm is explained below. The structural formula of DBtPBfpm is shown below.

[0289] [ka]

[0290] <4-[3-(dibenzothiophen-4-yl)phenyl]-8-(9,9-dimethylphenyl) 8FL-4 Synthesis of mDBtPBfpm) First, 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]be 1.5 g of benzofuro[3,2-d]pyrimidine and 9,9-dimethylfluorene-2-boro 1.0 g of phosphoric acid, 2.7 g of tripotassium phosphate, 35 mL of diglyme, and t-butanoic acid. 1.9 g of palladium acetate was added to a three-neck flask, the atmosphere in the flask was replaced with nitrogen, and palladium acetate (II) was added. Add 28 mg of di(1-adamantyl)-n-butylphosphine and 93 mg of di(1-adamantyl)-n-butylphosphine, and place under a nitrogen stream. The mixture was heated at 135° C. for 15 hours. Water was added to the reaction mixture, which was then filtered. The filter cake was washed successively with ethanol.

[0291] Next, the residue was dissolved in boiling toluene and charged in the order of Celite, alumina, and Celite. The resulting solution was concentrated to dryness and then extracted with toluene and ethanol. The product was recrystallized at 1.6 g of a yellowish white solid in a yield of 79%. The scheme is shown in formula (b-1) below.

[0292] [ka]

[0293] The resulting yellowish white solid (1.6 g) was purified by train sublimation. The purification conditions were a pressure of 2.8 Pa, argon gas flow rate of 10 mL / min, and 31 The solid was heated at 5°C. After purification by sublimation, 1.0 g of the desired yellow solid was obtained with a recovery rate of 63%. .

[0294] Nuclear magnetic resonance spectroscopy of the resulting yellow solid ( 1 The results of the analysis by H-NMR are shown below. Ta, 1 The H-NMR chart is shown in FIG. The organic compound represented by the formula (101), 8FL-4mDBtPBfpm, was obtained. Understood.

[0295] 1 H-NMR.δ(TCE-d2):1.50(s,6H), 7.27-7.32(m, 2H), 7.40-7.47(m,3H), 7.56-7.63(m,3H), 7.69 -7.79(m,5H), 7.82(d,1H), 7.92(d,1H), 8.00(d d,1H), 8.18(dd,2H), 8.55(ds,1H), 8.65(d,1H) , 8.96(s,1H), 9.26(s,1H).

[0296] Next, the absorption and emission spectra of 8FL-4mDBtPBfpm in toluene solution were The torque is shown in Figure 13(A), where the horizontal axis represents the wavelength and the vertical axis represents the absorption intensity and emission intensity.

[0297] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The absorption spectrum of 8FL-4mDBtPBfpm in toluene solution was Absorption spectrum obtained by measuring a toluene solution of mDBtPBfpm in a quartz cell The absorption spectrum obtained by measuring toluene in a quartz cell was subtracted from the above. The emission spectrum was measured using a PL-EL measuring device (Hamamatsu Photonics). The emission spectrum of 8FL-4mDBtPBfpm in toluene solution was A toluene solution of DBtPBfpm was placed in a quartz cell and measured.

[0298] As shown in FIG. 13(A), in the toluene solution of 8FL-4mDBtPBfpm, the peaks at 281 nm and Absorption peaks were observed at 294 nm, 320 nm, and 334 nm, and 422 nm (excitation wavelength The emission wavelength peak was observed around 331 nm.

[0299] Next, the absorption and emission spectra of the solid thin film of 8FL-4mDBtPBfpm The solid thin film was prepared on a quartz substrate by vacuum deposition. Torr is the absorbance (-log10 [%T / (10 The absorption spectrum was calculated using the formula: (0-%R) (where %T is the transmittance and %R is the reflectance). A UV-Vis spectrophotometer (U4100, Hitachi High-Technologies Corporation) was used to measure the The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS 920) was used. The absorption and emission spectra of the obtained solid thin film were measured. is shown in Figure 13(B). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0300] From the results of FIG. 13(B), the solid thin film of 8FL-4mDBtPBfpm has a thickness of 213 nm, Absorption peaks were observed at 237 nm, 290 nm, 322 nm, and 338 nm. An emission wavelength peak was observed around 350 nm (excitation wavelength: 350 nm).

[0301] Next, 8FL-4mDBtPBfpm obtained in this example was analyzed by liquid chromatography mass spectrometry. (Liquid Chromatography Mass Spectrometry The analysis was performed using LC / MS (abbreviation: LC / MS analysis).

[0302] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30. LC (liquid chromatography) separation was performed using Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fiscal.

[0303] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was appropriately selected as the delivery condition. The sample was prepared by dissolving 8FL-4mDBtPBfpm at any concentration in an organic solvent. The injection volume was 5.0 μL.

[0304] Targeted-MS 2 The ion derived from 8FL-4mDBtPBfpm was MS m / z=621.19 2 Measurements were performed using Targeted-MS. 2 The settings are The mass range of the target ions was m / z = 621.19 ± 2.0 (isolation width The detection was performed in positive mode with the NDOW setting set to 4. The target was detected in the collision cell. The energy that accelerates ions is called Normal Collision Energy (NCE). The measurement was performed with an energy of 80. The obtained MS spectrum is shown in FIG.

[0305] From the results in Figure 14, 8FL-4mDBtPBfpm mainly exhibited the following peaks: m / z = 605, 578 , 421, 344, 319, 284, 265, 241, and 197 are product ions. The results shown in Figure 14 are for 8FL-4mDBtPBfpm. Since the results show characteristics derived from 8FL-4mD in the mixture, This is important data for identifying BtPBfpm.

[0306] The product ion at m / z=605 was determined to be the product ion in 8FL-4mDBtPBfpm. It is assumed that the cation generated by the elimination of the methyl group from 8FL-4mDBtPBfpm is This suggests that the product ions contain methyl groups. The methyl group of FL-4mDBtPBfpm is further removed. The product ion at z=343 is due to the loss of the phenyl and dibenzothiophenyl groups. It is assumed that 8FL-4mDBtPBfpm is a cation formed by the phenyl group and dibenzoyl group. This suggests that it contains a zothiophenyl group.

[0307] In addition, the product ion at m / z=197 is a cation of the dibenzothiophenyl group. It is estimated that 8FL-4mDBtPBfpm contains a dibenzothiophenyl group. This suggests that... EXAMPLES

[0308] <Synthesis Example 3> In this synthesis example, the organic compound represented by the structural formula (102) in the first embodiment of the present invention is Compound 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalene-2 -yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPB The synthesis method of 8βN-4mDBtPBfpm is as follows: As shown below.

[0309] [ka]

[0310] <4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalene-2-yl)phenyl 8βN-4mDBtPBfp m) Synthesis First, 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]-[1]be 1.5 g of benzofuro[3,2-d]pyrimidine, 0.73 g of 2-naphthaleneboronic acid, Add 1.5 g of cesium fluoride and 32 mL of mesitylene to a 100 mL three-neck flask and Nitrogen substitution in Lasco, 2'-(dicyclohexylphosphino)acetophenone ethylene 70 mg of ketal and tris(dibenzylideneacetone)dipalladium(0) (abbreviation: P 89 mg of d2(dba)3) was added, and the mixture was heated at 120° C. for 5 hours under a nitrogen stream. Water was added to the reaction mixture, which was then filtered, and the filter cake was washed successively with water and ethanol.

[0311] The residue was dissolved in toluene and filtered through a filter aid packed with Celite, alumina, and Celite in that order. The solvent in the resulting solution was concentrated, and the target compound was obtained by recrystallization. A yellow solid was obtained in an amount of 1.5 g and a yield of 64%. The synthesis scheme is shown in the following formula (c-1).

[0312] [ka]

[0313] The resulting pale yellow solid (1.5 g) was purified by train sublimation. The purification conditions were a pressure of 2.0 Pa, argon gas flow rate of 10 mL / min, and The solid was heated at 90°C. After purification by sublimation, 0.60 g of the desired yellow solid was obtained, with a recovery rate of 39%. Got it.

[0314] Nuclear magnetic resonance spectroscopy of the resulting yellow solid ( 1 The results of the analysis by H-NMR are shown below. Ta, 1 The H-NMR chart is shown in FIG. The organic compound represented by the formula (102), 8βN-4mDBtPBfpm, was obtained. Understood.

[0315] 1 H-NMR.δ(TCE-d2):7.45-7.50(m,4H), 7.57-7. 62(m,2H), 7.72-7.93(m,8H), 8.03(d,1H), 8.10 (s,1H), 8.17(d,2H), 8.60(s,1H), 8.66(d,1H), 8.98(s,1H), 9.28(s,1H).

[0316] Next, the absorption and emission spectra of 8βN-4mDBtPBfpm in toluene solution were The torque is shown in Figure 16(A), where the horizontal axis represents the wavelength and the vertical axis represents the absorption intensity and emission intensity.

[0317] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (V550, manufactured by JASCO Corporation). The absorption spectrum of 8βN-4mDBtPBfpm in toluene solution was Absorption spectrum obtained by measuring a toluene solution of mDBtPBfpm in a quartz cell The absorption spectrum obtained by measuring toluene in a quartz cell was subtracted from the above. The emission spectrum was measured using a PL-EL measuring device (Hamamatsu Photonics). The emission spectrum of 8βN-4mDBtPBfpm in toluene solution was A toluene solution of DBtPBfpm was placed in a quartz cell and measured.

[0318] As shown in FIG. 16(A), in the toluene solution of 8βN-4mDBtPBfpm, the peaks at 283 nm and Absorption peaks were observed at 290 nm, 317 nm, and 333 nm, and 409 nm (excitation wavelength The emission wavelength peak was observed around 337 nm.

[0319] Next, the absorption and emission spectra of the solid thin film of 8βN-4mDBtPBfpm The solid thin film was prepared on a quartz substrate by vacuum deposition. Torr is the absorbance (-log10 [%T / (10 The absorption spectrum was calculated using the formula: (0-%R) (where %T is the transmittance and %R is the reflectance). A UV-Vis spectrophotometer (U4100, Hitachi High-Technologies Corporation) was used to measure the The emission spectrum was measured using a fluorometer (Hamamatsu Photonics FS 920) was used. The absorption and emission spectra of the obtained solid thin film were measured. is shown in Figure 16(B). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity and emission intensity.

[0320] From the results of FIG. 16(B), the solid thin film of 8βN-4mDBtPBfpm has a thickness of 243 nm, Absorption peaks were observed at 266 nm, 290 nm, 314 nm, and 341 nm, and An emission wavelength peak was observed around 330 nm (excitation wavelength: 330 nm).

[0321] Next, the 8βN-4mDBtPBfpm obtained in this example was analyzed by liquid chromatography mass spectrometry. (Liquid Chromatography Mass Spectrometry The analysis was performed using LC / MS (abbreviation: LC / MS analysis).

[0322] LC / MS analysis was performed using Thermo Fisher Scientific Ultimate 30. LC (liquid chromatography) separation was performed using Thermo Fisher Scientific MS analysis (mass spectrometry) was performed using a Q Exactive manufactured by Fiscal.

[0323] For LC separation, any column was used, the column temperature was set to 40°C, and the solvent was appropriately selected as the delivery condition. The sample was prepared by dissolving 8βN-4mDBtPBfpm at any concentration in an organic solvent. The injection volume was 5.0 μL.

[0324] Targeted-MS 2The ion derived from 8βN-4mDBtPBfpm was MS m / z=554.15 2 Measurements were performed using Targeted-MS. 2 The settings are -The mass range of the target ions was m / z = 554.15 ± 2.0 (isolation width The detection was performed in positive mode with the NDOW setting set to 4. The target was detected in the collision cell. The energy that accelerates ions is called Normal Collision Energy (NCE). The measurement was performed with an energy of 65. The obtained MS spectrum is shown in FIG.

[0325] From the results in Figure 17, 8βN-4mDBtPBfpm mainly has m / z=528 and 499 , 371, 347, 310, 295, 284, 270, 260, 245, 241, 221 It was found that product ions were detected around 215 and 197. The results shown are characteristic of 8βN-4mDBtPBfpm. This provides important data for identifying 8βN-4mDBtPBfpm contained in the mixture. It can be said that this is

[0326] The product ion at m / z=371 is due to the elimination of the dibenzothiophenyl group. The generated cation is assumed to be 8βN-4mDBtPBfpm, which is a dibenzothiophenyl group. This suggests that it contains EXAMPLES

[0327] In this example, the 4-[3-( Dibenzothiophene-4-yl)phenyl]-8-(triphenylen-2-yl)-[1 ]Benzofuro[3,2-d]pyrimidine (abbreviation: 8Tp-4mDBtPBfpm) (structure A light-emitting device 1 using the compound of formula (100) in the light-emitting layer, and a light-emitting device 2 using the compound of formula (100) in the light-emitting layer, Thiophen-4-yl)phenyl]-8-(9,9-dimethylfluoren-2-yl)- [1] Benzofuro[3,2-d]pyrimidine (abbreviation: 8FL-4mDBtPBfpm) A light-emitting element 2 using the structural formula (101)) in the light-emitting layer, [1]benzothiophen-4-yl)phenyl]-8-(naphthalen-2-yl)-[1]benzo Furo[3,2-d]pyrimidine (abbreviation: 8βN-4mDBtPBfpm) (structural formula (10 2)) for the light-emitting layer. The structure of the light-emitting element used in this embodiment is shown in FIG. The general configuration is shown in Table 1. The chemical formulas of the materials used in this example are shown below.

[0328] [Table 1]

[0329] [ka]

[0330] <Fabrication of light-emitting element> The light emitting device shown in this embodiment has a first electrode 9 formed on a substrate 900 as shown in FIG. 01, a hole injection layer 911, a hole transport layer 912, a light emitting layer 913, an electron transport layer 914, and an electron A structure in which an electron injection layer 915 is laminated in this order, and a second electrode 903 is laminated on the electron injection layer 915. has.

[0331] First, a first electrode 901 was formed on a substrate 900. The electrode area was 4 mm2 (2mm x 2 The thickness of the first electrode 901 was 1 mm. The substrate 900 was a glass substrate. , Indium tin oxide containing silicon oxide (ITSO) was deposited by sputtering to a thickness of 70 nm. The film was formed to a thickness of 100 nm.

[0332] As a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 60 minutes in the heating chamber. After that, the substrate was allowed to cool for about 30 minutes.

[0333] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed by vacuum evaporation. 10 -4 After the pressure was reduced to 10 Pa, DBT3P-II and molybdenum oxide were 3P-II: Molybdenum oxide = 2:1 (mass ratio), and the film thickness was adjusted to 50 nm. They were formed by co-evaporation.

[0334] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was formed by The film was formed by vapor deposition using Bi1BP to a thickness of 20 nm.

[0335] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0336] In the case of the light-emitting element 1, the light-emitting layer 913 is made of 8Tp-4mDBtPBfp m was used as the assist material, and [Ir(ppy )2(4dppy)] was used, with a weight ratio of 8Tp-4mDBtPBfpm:PCCP:[I The vapor deposition was carried out so that the ratio of r(ppy)2(4dppy)]=0.6:0.4:0.1. The film thickness was 40 nm.

[0337] In the case of the light-emitting element 2, the light-emitting layer 913 contains 8FL-4mDBtPBfp as a host material. m was used as the assist material, and [Ir(ppy )2(4dppy)] was used, with a weight ratio of 8FL-4mDBtPBfpm:PCCP:[I The vapor deposition was carried out so that the ratio of r(ppy)2(4dppy)]=0.6:0.4:0.1. The film thickness was 40 nm.

[0338] In the case of the light-emitting element 3, the light-emitting layer 913 is made of 8βN-4mDBtPBfp m was used as the assist material, and [Ir(ppy )2(4dppy)] was used, with a weight ratio of 8βN-4mDBtPBfpm:PCCP:[I The vapor deposition was carried out so that the ratio of r(ppy)2(4dppy)]=0.6:0.4:0.1. The film thickness was 40 nm.

[0339] Next, an electron transport layer 914 was formed on the light-emitting layer 913. In the case of , the thickness of 8Tp-4mDBtPBfpm is 20nm, and the thickness of Bphen is 15nm. In the case of the light-emitting element 2, 8FL-4mDBt The PBfpm film thickness was 20 nm, and the Bphen film thickness was 15 nm. In the case of light-emitting device 3, the film thickness of 8βN-4mDBtPBfpm was 20 nm, and The layers were deposited in sequence so that the thickness of en was 15 nm.

[0340] Next, the electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was made of fluoride. Lithium (LiF) was used and the film was formed by vapor deposition to a thickness of 1 nm.

[0341] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was made of aluminum. The aluminum was deposited by vapor deposition to a thickness of 200 nm. Thus, the second electrode 903 functions as a cathode.

[0342] Through the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 900. In addition, the hole injection layer 911, the hole transport layer 912, the light emitting layer 913, and the electrode layer 914 described in the above steps were The electron transport layer 914 and the electron injection layer 915 are functional layers constituting the EL layer in one embodiment of the present invention. In addition, in the deposition process in the above-mentioned manufacturing method, the deposition method is all performed by resistance heating. Used.

[0343] Moreover, the light emitting element manufactured as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the sealing is performed in a glove box with a nitrogen atmosphere. Then, another substrate (not shown) is fixed onto the substrate 900 using a sealing material, and the sealing material is It is applied around the light-emitting element formed on 00, and 365 nm ultraviolet light is applied at 6 J / cm during sealing. 2 The irradiation was performed by heating at 80°C for 1 hour.

[0344] <Operation characteristics of light-emitting element> The operating characteristics of each of the fabricated light-emitting devices were measured. The measurements were performed at room temperature (25°C). The results of the operating characteristics of the light-emitting element 1, the light-emitting element 2, and the light-emitting element 3 are shown below. The current density-luminance characteristics are shown in Fig. 19, the voltage-luminance characteristics in Fig. 20, and the luminance-current efficiency characteristics in Fig. 21 and the voltage-current characteristics are shown in Figure 22.

[0345] Also, 1000cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 2 below. .

[0346] [Table 2]

[0347] From the above results, it is clear that all of the light-emitting elements fabricated in this example exhibit excellent element characteristics. Light.

[0348] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 23, the emission spectrum of each light-emitting element is 560n m, and the [Ir(ppy)2(4dpp y)].

[0349] Next, a reliability test was performed on each light-emitting element. The results of the reliability test are shown in FIG. In Figure 4, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test was performed at a constant current of 2 mA. .

[0350] From the results of the reliability test, each of the light-emitting elements shown in this example exhibits good element characteristics. It becomes clear that...

[0351] In each of the light-emitting elements shown in this embodiment, an exciplex is formed in each light-emitting layer, and an exciplex is generated. The energy transfer from the complex to the luminescent material, [Ir(ppy)2(4dppy)] In this configuration, the present invention provides an ex-TET (ExT) structure. The 8Tp-4mDBtPBfpm and 8FL-4mD BtPBfpm and 8βN-4mDBtPBfpm have a benzofuropyrimidine skeleton. Since the LUMO level is deep, it is suitable for forming an exciplex. Each of the light-emitting devices has the advantage of being able to emit light using ExTET and to reduce the driving voltage. Yes. EXAMPLES

[0352] In this embodiment, the 8βN-4m A light-emitting device 4 using DBtPBfpm (structural formula (102)) as the light-emitting layer, and an organic compound for comparison Compound, 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1]benzo Furo[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm) (structural formula (200 The structure, fabrication method and the like of the comparative light-emitting element 5 using the above-mentioned compound (I)) as the light-emitting layer are described below. The characteristics will be described. The structure of the light-emitting element used in this embodiment is shown in FIG. The physical composition is shown in Table 3. The chemical formulas of the materials used in this example are shown below.

[0353] [Table 3]

[0354] [ka]

[0355] <Fabrication of light-emitting element> The light emitting device shown in this embodiment has a first electrode 9 formed on a substrate 900 as shown in FIG. 01, a hole injection layer 911, a hole transport layer 912, a light emitting layer 913, an electron transport layer 914, and an electron A structure in which an electron injection layer 915 is laminated in this order, and a second electrode 903 is laminated on the electron injection layer 915. has.

[0356] First, a first electrode 901 was formed on a substrate 900. The electrode area was 4 mm 2 (2mm x 2 The thickness of the first electrode 901 was 1 mm. The substrate 900 was a glass substrate. , Indium tin oxide containing silicon oxide (ITSO) was deposited by sputtering to a thickness of 70 nm. The film was formed to a thickness of 100 nm.

[0357] As a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 60 minutes in the heating chamber. After that, the substrate was allowed to cool for about 30 minutes.

[0358] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed by vacuum evaporation. 10 -4 After the pressure was reduced to 10 Pa, DBT3P-II and molybdenum oxide were 3P-II: Molybdenum oxide = 2:1 (mass ratio), and the film thickness was adjusted to 50 nm. They were formed by co-evaporation.

[0359] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was formed by The film was formed by vapor deposition using Bi1BP to a thickness of 20 nm.

[0360] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0361] In the case of the light-emitting element 4, the light-emitting layer 913 is made of 8βN-4mDBtPBfp m was used as the assist material, and [Ir(ppy )2(4dppy)] was used, with a weight ratio of 8βN-4mDBtPBfpm:PCCP:[I The vapor deposition was carried out so that the ratio of r(ppy)2(4dppy)]=0.6:0.4:0.1. The film thickness was 40 nm.

[0362] In the case of the comparative light-emitting element 5, the light-emitting layer 913 contains 4,8mDBtP2Bf as a host material. pm was used as the assist material, and [Ir(pp y)2(4dppy)] was used, with a weight ratio of 4.8mDBtP2Bfpm:PCCP:[I The vapor deposition was carried out so that the ratio of r(ppy)2(4dppy)]=0.6:0.4:0.1. The film thickness was 40 nm.

[0363] Next, an electron transport layer 914 was formed on the light-emitting layer 913. In the case of , the thickness of 8βN-4mDBtPBfpm is 20 nm, and the thickness of Bphen is 15 nm. In the case of comparative light-emitting element 5, 4,8mDBtP2B The fpm film thickness was 20 nm, and the Bphen film thickness was 15 nm. Ta.

[0364] Next, the electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 was made of fluoride. Lithium (LiF) was used and the film was formed by vapor deposition to a thickness of 1 nm.

[0365] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was made of aluminum. The aluminum was deposited by vapor deposition to a thickness of 200 nm. Thus, the second electrode 903 functions as a cathode.

[0366] Through the above steps, a light-emitting element having an EL layer sandwiched between a pair of electrodes is formed on the substrate 900. In addition, the hole injection layer 911, the hole transport layer 912, the light emitting layer 913, and the electrode layer 914 described in the above steps were The electron transport layer 914 and the electron injection layer 915 are functional layers constituting the EL layer in one embodiment of the present invention. In addition, in the deposition process in the above-mentioned manufacturing method, the deposition method is all performed by resistance heating. Used.

[0367] Moreover, the light emitting element manufactured as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the sealing is performed in a glove box with a nitrogen atmosphere. After applying a sealant to the periphery of the light emitting element formed on the substrate 900, a desiccant is provided. Another substrate (not shown) is placed on the substrate 900 at a desired position, and 365 nm ultraviolet light is applied for 6 J. / cm 2 Irradiated.

[0368] <Operation characteristics of light-emitting element> The operating characteristics of the fabricated light-emitting element 4 and the comparative light-emitting element 5 were measured. The operation of the light-emitting element 4 and the comparative light-emitting element 5 was also As the results, the current density-luminance characteristics are shown in Fig. 25, the voltage-luminance characteristics in Fig. 26, and the luminance-current efficiency characteristics in Fig. 27. The rate characteristics are shown in FIG. 27 and the voltage-current characteristics are shown in FIG.

[0369] Also, 1000cd / m 2 Main initial characteristics of the light-emitting element 4 and the comparative light-emitting element 5 in the vicinity The values ​​are shown in Table 4 below.

[0370] [Table 4]

[0371] The above results show that the light-emitting element 4 fabricated in this example exhibits excellent element characteristics.

[0372] Furthermore, the light-emitting element 4 and the comparative light-emitting element 5 were subjected to an electric current of 2.5 mA / cm 2 A current was passed with a current density of The emission spectrum at that time is shown in FIG. 29. As shown in FIG. 29, the emission spectrum of each light-emitting element Each of these has a peak near 560 nm, and is the same as the [Ir( ppy)2(4dppy)].

[0373] Next, a reliability test was performed on the light-emitting element 4 and the comparative light-emitting element 5. Results of the reliability test This is shown in FIG. 30. In FIG. 30, the vertical axis represents the normalized brightness (%) when the initial brightness is 100%. The horizontal axis indicates the operation time (h) of the element. The reliability test was performed at a constant current of 2 mA. A current drive test was carried out.

[0374] The results of the reliability test showed that the light-emitting element 4 of one embodiment of the present invention was more reliable than the comparative light-emitting element 5. In particular, the time it takes for the luminance to decay to 90% of the initial value was The LT90 of the comparative light-emitting element 5 is 78 hours, while that of the comparative light-emitting element 6 is 100 hours. The LT90 of element 4 was 215 hours, which is about 2.8 times longer than that of element 4. Therefore, the organic compound according to one embodiment of the present invention, 8βN-4mDBtPBfpm (structural formula: 102)) is useful for extending the life of light-emitting devices. From the results of the examples, it is possible to obtain a benzofuropyrimidine or benzothienopyrimidine benzene compound. It can be seen that directly bonding a condensed ring to the aryl side directly leads to a longer device life. EXAMPLES

[0375] <Synthesis Example 4> In this synthesis example, the organic compound represented by the structural formula (145) in the first embodiment of the present invention is Compound, 8-(dibenzothiophen-4-yl)-2-[3-(dibenzothiophen-4-yl) 8DBt-2m The synthesis method for 8DBt-2mDBtPBfp is explained below. The structural formula of m is shown below.

[0376] [ka]

[0377] <Step 1: Synthesis of 2-chloro-4-(dibenzothiophen-4-yl)phenol> First, 3.4 g of 4-dibenzothiopheneboronic acid and tris(2-methylphenyl)phos 0.18 g of fin (abbreviation: P(o-tolyl)3), 4.1 g of potassium carbonate, and Put 56 mL of benzene, 19 mL of ethanol, and 15 mL of water into a three-neck flask and stir under reduced pressure. The mixture was degassed and replaced with nitrogen by stirring. Add 3.1 g of palladium(II) acetate (abbreviation: Pd(OAc)2) and 67 mg of palladium(II) acetate. The mixture was stirred at 0°C for 14 hours. After the specified time, water was added to the mixture and it was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated saline and dried over magnesium sulfate. The mixture was filtered and the filtrate was concentrated to give a brown oil. This oil was dissolved in toluene and The amount of hexane was gradually reduced from 5:1 hexane:ethyl acetate to 5:1 hexane:acetic acid. When purified by silica gel column chromatography using a 2:1 ratio, the desired product was obtained. The resulting pale yellow solid was 4.3 g in a yield of 91%. The synthesis scheme for step 1 is shown below: d-1).

[0378] [ka]

[0379] <Step 2: 4-(dibenzothiophen-4-yl)-2-(4,4,5,5-tetramethylphenyl)-2-(4-methylphenyl ...,4,5,5-tetramethylphenyl)-2-(4,4,5,5-tetramethylphenyl)-2-(4,4,5,5 Synthesis of methyl-1,3,2-dioxaborolan-2-yl)phenol> Next, 2-chloro-4-(dibenzothiophen-4-yl) fluoride synthesized in step 1 above was 0.31 g of phenol, 0.28 g of bis(pinacolato)diboron, and potassium acetate (A 0.30 g of COK and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl Put 17 mg of phenyl (S-Phos) and 2.5 mL of 1,4-dioxane into a two-neck flask. The mixture was stirred under reduced pressure to degas the mixture and replaced with nitrogen.

[0380] This mixture was mixed with tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(d ba) 3) 18 mg was added and stirred at 100 ° C for 7 hours. After the specified time, Water was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated saline to remove sulfuric acid. The mixture was gravity filtered, and the filtrate was concentrated to give a brown oil. The oil was dissolved in toluene and the mixture was stirred with silica gel using hexane:ethyl acetate = 5:1 as a developing solvent. The target pale yellow solid was obtained in a yield of 0. The synthesis scheme of step 2 is shown in the following formula (d-2).

[0381] [ka]

[0382] <Step 3: 2,5-dichloro-4-[2-hydroxy-5-(dibenzothiophene Synthesis of 4-yl)phenyl]pyrimidine> Next, 4-(dibenzothiophene-4-yl)-2-(4,4 ,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 0.2 1g, triphenylphosphine 13mg, potassium acetate 0.10g, acetonitrile Add 1.9 mL of ethanol and 0.48 mL of water to a three-neck flask and stir under reduced pressure to remove the The mixture was vented and replaced with nitrogen. 62 μL of 2,4,5-trichloropyrimidine and acetic acid were added to the mixture. Palladium (II) (7.0 mg) was added and the mixture was stirred at room temperature for 18 hours. Water was added to the mixture, which was then extracted with ethyl acetate. The resulting organic layer was washed with water and saturated saline. The mixture was gravity filtered, and the filtrate was concentrated to give a brown oil. This oil was dissolved in toluene, and the mixture was developed with a mixture of hexane and ethyl acetate (5:1). By purifying it by silica gel column chromatography, the target pale yellow solid was obtained. The yield was 0.12 g and the yield was 55%. The synthesis scheme of step 3 is shown in the following formula (d-3). vinegar.

[0383] [ka]

[0384] <Step 4: 2-Chloro-8-(dibenzothiophen-4-yl)-[1]benzofuro Synthesis of [3,2-d]pyrimidine> Next, 2,5-dichloro-4-[2-hydroxy-5-(dibenzyl) 0.36 g of benzothiophene-4-ylphenylpyrimidine and dimethylacetamide (abbreviation: DMAC) 34 mL was added to a two-neck flask and degassed by stirring under reduced pressure. The mixture was then added with copper(I) thiophene-2-carboxylate (abbreviation: CuTC). 0.21 mg was added, and the mixture was stirred at 80° C. for 9.5 hours.

[0385] After a certain period of time had elapsed, saline was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was then washed with water and saturated sodium chloride solution. The mixture was washed with brine and dried over magnesium sulfate. The mixture was gravity filtered, and the filtrate was concentrated to give A yellow solid was obtained. This solid was dissolved in toluene and eluted with hexane:ethyl acetate=5:1. The target white The solid was obtained in an amount of 0.16 g and a yield of 50%. The synthesis scheme of step 4 is shown in the following formula (d-4 ) as shown in

[0386] [ka]

[0387] <Step 5: 8-(dibenzothiophen-4-yl)-2-[3-(dibenzothiophene-4-yl)- 8DB Synthesis of t-2mDBtPBfpm) Next, 2-chloro-8-(dibenzothiophen-4-yl)- [1] 0.10 g of benzofuro[3,2-d]pyrimidine and 3-(dibenzothiophene- 4-yl)phenylboronic acid 99 mg, potassium phosphate tripotassium 0.17 g, and diglym Add 2.7 mL of e and 6.7 mg of t-butanol to a three-neck flask and stir under reduced pressure. The mixture was degassed and replaced with nitrogen. 6.0 mg of (1-adamantyl)-n-butylphosphine was added, and the mixture was heated for 120 The mixture was stirred at 140°C for 7.5 hours, and then stirred at 140°C for 1.5 hours. Water was added to the mixture, the precipitate was filtered off with suction, and the filter cake was washed with ethanol.

[0388] Add hot toluene to the residue and dissolve it. Then, fill with Celite, alumina, and Celite in that order. The resulting solution was filtered using a filter aid filled with water. The solvent in the resulting solution was concentrated to dryness and recrystallized with toluene. By crystallizing the mixture, a white solid, 8DBt-2mDBtPBfpm (abbreviation) of the present invention, was obtained. The yield was 0.040 g and the yield was 24%. The synthesis scheme of step 5 is shown in the following formula (d-5). show.

[0389] [ka]

[0390] Nuclear magnetic resonance spectroscopy of the resulting white solid ( 1 The results of the analysis by H-NMR are shown below. From the results, in this example, the organic compound represented by the above structural formula (145), 8DB It was found that t-2mDBtPBfpm was obtained.

[0391] 1 H-NMR.δ(CDCl3):7.42-7.52(m,4H), 7.59(t,3 H), 7.64(d,1H), 7.69(t,1H), 7.82-7.85(m,3H) , 7.90(d,1H), 8.12(dd,1H), 8.18-8.23(m,4H), 8.68(dt,1H), 8.70(sd,1H), 8.99(st,1H), 9.16 (s,1H).

[0392] <Reference synthesis example> In this Reference Synthesis Example, the benzofuropyrimidine compound described in Example 5, 4,8-biphenyl S[3-(dibenzothiophen-4-yl)phenyl]-[1]benzofuro[3,2-d ] Pyrimidine (abbreviation: 4,8mDBtP2Bfpm) (structural formula (200)) synthesis method The structure of 4,8mDBtP2Bfpm is shown below.

[0393] [ka]

[0394] <Step 1: 8-chloro-4-[3-(dibenzothiophen-4-yl)phenyl]- [1] Synthesis of benzofuro[3,2-d]pyrimidine≫ First, 1.0 g of 4,8-dichloro[1]benzofuro[3,2-d]pyrimidine and 2.6 g of 3-(dibenzothiophen-4-yl)phenylboronic acid and 1.2 g of charcoal Potassium chloride, 42 mL of toluene, 4 mL of ethanol, and 4 mL of water were placed in a reflux condenser. The flask was filled with nitrogen, and 0.29 g of bis(triphenylphosphine) was added. (II) dichloride (abbreviation: Pd(PPh3)2Cl2) The mixture was heated at 80° C. for 8 hours under a nitrogen stream. The reaction mixture was filtered and diluted with water and ethanol. The target product (gray solid) was obtained in 1.9 g in a yield of 96%. The synthesis scheme of compound 1 is shown in the following formula (A-1).

[0395] [ka]

[0396] The gray solid obtained in step 1 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. It was found that 1,2-diphenyl-[1,2-phenyl]-[1,2-phenyl]-benzofuro[3,2-d]pyrimidine was obtained. Ta.

[0397] 1 H-NMR.δ(TCE-d2):7.48-7.52(m,2H), 7.63-7. 71(m,4H), 7.77-7.80(t,1H),7.85(d,1H), 7.96 (d,1H), 8.22-8.23(m,2H), 8.28(s,1H), 8.65(d ,1H), 8.96(s,1H), 9.29(s,1H).

[0398] <Step 2: 4,8-bis[3-(dibenzothiophen-4-yl)phenyl]-[1 ]Synthesis of benzofuro[3,2-d]pyrimidine (abbreviation: 4,8mDBtP2Bfpm)≫ Next, 8-chloro-4-[3-(dibenzothiophene-4-yl) 1.7 g of [1-phenyl]-[1]benzofuro[3,2-d]pyrimidine and 1.1 g of g of 3-(dibenzothiophen-4-yl)phenylboronic acid and 1.6 g of potassium phosphate and 60mL of diethylene glycol dimethyl ether (abbreviation: diglyme). The flask was filled with nitrogen, and 90 mg of palladium acetate and 0.29 g Di(1-adamantyl)-n-butylphosphine was added and the mixture was heated to 160°C under a nitrogen stream. The reaction mixture was filtered and washed with water and then with ethanol. The filtrate was passed through a filter aid packed with Celite, aluminum oxide and Celite in this order. The resulting solution was recrystallized to give 1.2 g of 4,8mDBtP2Bfpm in a yield of 47. % (yellowish white solid). 1.2 g of this yellowish white solid was subjected to train sublimation. The sublimation purification conditions were a pressure of 2.6 Pa and an argon gas flow rate of 5 mL. The solid was heated at 330°C while flowing at 1000 / min. After purification by sublimation, the target yellowish white solid was obtained. The synthesis scheme of step 2 is shown in the following formula (A-2).

[0399] [ka]

[0400] The yellow-white solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. This shows that 4,8mDBtP2Bfpm was obtained. I did.

[0401] 1 H-NMR.δ(TCE-d2):7.48-7.52(t,4H), 7.60(s, 1H), 7.61(d,1H), 7.65-7.69(m,3H), 7.79-7.83 (m,3H), 7.86-7.89(m,3H), 8.00(d,1H), 8.07(s ,1H), 8.10(d,1H), 8.19-8.24(m,4H), 8.69-8.7 2(t,2H), 9.02(s,1H), 9.32(s,1H). EXAMPLES

[0402] <Synthesis Example 5> In this synthesis example, the organic compound represented by the structural formula (103) in the first embodiment of the present invention is Compound 4-[3-(dibenzothiophen-4-yl)phenyl]-8-(naphthalene-1 -yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8αN-4mDBtPB The synthesis method of 8αN-4mDBtPBfpm is shown below. vinegar.

[0403] [ka]

[0404] <Step 1: Synthesis of 2-hydroxy-5-(naphthalen-1-yl)benzonitrile> First, 2.97 g of 6-bromo-2-hydroxybenzonitrile, 1-naphthalene Boronic acid 2.8g, tris(2-methylphenyl)phosphine (P(o-tol)3)0 .184g, potassium carbonate 4.15g, toluene 56mL, ethanol 19mL, water 15 The mixture was stirred under reduced pressure to degas it and replace the air with nitrogen. 69.3 mg of palladium(II) acetate (Pd(OAc)2) was added to the mixture and heated at 100°C for 1 The mixture was stirred for 7.5 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The mixture was washed with water and saturated saline and dried over magnesium sulfate. The filtrate was concentrated to give a light brown solid. This solid was dissolved in a mixed solvent of heated toluene and ethyl acetate. Dissolve in hexane and ethyl acetate in a ratio of 3:1. Gradually reduce the amount of hexane. Finally, the mixture was purified by silica gel column chromatography using hexane:ethyl acetate=1:1. The target product was obtained in an amount of 3.43 g (yield 93%, pale yellow solid). The synthesis scheme is shown in the following formula (e-1).

[0405] [ka]

[0406] Step 2: 3-amino-5-(naphthalen-1-yl)benzo[b]furan-2-carboxylate Synthesis of Ethyl Carboxylate> Next, 2-hydroxy-5-(naphthalene-1-yl)benzoyl ester synthesized in step 1 above was 3.43 g of nitrile and 3.87 g of potassium carbonate were placed in a three-neck flask and the atmosphere was replaced with nitrogen. A mixture of 3.51 g of ethyl bromoacetate and 18 g of N,N-dimethylformamide (DMF) was added. The reaction mixture was added with 1 mL of 1,000 mL of ethyl acetate and stirred at 100° C. for 5 hours. The reaction mixture was placed in ice water and stirred for 1 hour. The target product was obtained as a dark brown residue (4.97 g) by suction filtration. is shown in the following formula (e-2).

[0407] [ka]

[0408] <Step 3: 8-(naphthalen-1-yl)-[1]benzofuro[3,2-d]pyrimidinyl Synthesis of din-4(3H)-one Place 4.97 g of the dark brown material obtained in step 2 and 20 mL of formamide in a recovery flask. To this mixture, 2.92 g of formamidine acetate was added and heated at 160°C. The mixture was stirred at 40° C. for 6.5 hours. Water was added to the reaction mixture, which was then suction filtered to obtain a residue. The residue was washed with ethyl acetate and hexane, and the desired product was obtained in a yield of 2.98 g (from step 2 to step 3). The synthesis scheme of step 3 is shown in the following formula (e-3). vinegar.

[0409] [ka]

[0410] <Step 4: 4-Chloro-8-(naphthalen-1-yl)-[1]benzofuro[3,2 -d]Synthesis of pyrimidine> 8-(Naphthalen-1-yl)-[1]benzofuro[3,2-d] synthesized in step 3 Pyrimidin-4(3H)-one 2.98 g, N,N-dimethylformamide (DMF) 74 μL was placed in a three-neck flask and stirred. 31.8 g of phosphoryl chloride was added to this mixture. The mixture was stirred at 90° C. for 11 hours. Phosphoryl chloride was distilled off from the reaction mixture. The mixture was poured into ice water, neutralized with saturated sodium bicarbonate water, and stirred for 1 hour. The filter cake was washed with ethanol, and the target product was found to be 3.12 g (yield 99%, light brown). The synthetic scheme of step 4 is shown in the following formula (e-4).

[0411] [ka]

[0412] <Step 5: Synthesis of 8αN-4mDBtPBfpm> 4-Chloro-8-(naphthalen-1-yl)-[1]benzofuro[3,2-d]pyrimidin 3.12g, 3-(dibenzothiophen-4-yl)phenylboronic acid 3.44g, charcoal 2.61 g of potassium chloride, 36 mL of toluene, 12 mL of ethanol, and 9.5 mL of water were added to a three-port flask. The mixture was poured into a flask and stirred under reduced pressure to degas and replace with nitrogen. 0.324 g of bistriphenylphosphinepalladium(II) (Pd(PPh4)2) The mixture was then stirred at 100° C. for 27.5 hours. Water was added to the reaction mixture, which was then suction filtered. The residue was washed with water and ethyl acetate, dissolved in hot toluene, and then extracted with celite and alumina. The resulting solution was concentrated to dryness and then filtered with toluene. The target compound was obtained in an amount of 3.0 g (yield 57%, white solid). 3.00 g of the white solid was purified by train sublimation. The solidification was performed at 290°C under a pressure of 3.7 Pa and an argon gas flow rate of 15 mL / min. After purification by sublimation, 1.86 g of the desired white solid was obtained with a recovery rate of 62%. The synthetic scheme of the compound 5 is shown in the following formula (e-5).

[0413] [ka]

[0414] The white solid obtained in step 5 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 31. It was found that -4mDBtPBfpm was obtained.

[0415] 1 H-NMR.δ(CDCl3):7.45-7.55(m,5H),7.59(t,1 H),7.63-7.67(m,2H),7.82(t,1H),7.85-8.00( m,7H),8.24(d,2H),8.44(s,1H),8.50(d,1H),9 .08(s,1H),9.32(s,1H). EXAMPLES

[0416] <Synthesis Example 6> In this synthesis example, the organic compound represented by the structural formula (116) in the first embodiment of the present invention is Compound 4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]-8-( Naphthalen-2-yl)-[1]benzofuro[3,2-d]pyrimidine (abbreviation: 8βN- The synthesis method of 8βN-4mDBtBPBfp is explained below. The structural formula of m is shown below.

[0417] [ka]

[0418] <Step 1: 8-chloro-4-[3'-(dibenzothiophen-4-yl)biphenyl Synthesis of -3-yl]-[1]benzofuro[3,2-d]pyrimidine> 4,8-Dichloro[1]benzofuro[3,2-d]pyrimidine 7.65g, 3'-(dibenzyl 17.0 g of benzothiophen-4-ylbiphenyl-3-boronic acid, 12. Put 4g, 360mL of toluene, 36mL of ethanol, and 45mL of water into a three-neck flask and reduce the The mixture was degassed by stirring under pressure and replaced with nitrogen. ) Add 2.25 g of palladium (II) dichloride (abbreviation: Pd(PPh3)2Cl2) The mixture was stirred at 80° C. for 6 hours. Water was added to the reaction mixture, which was then subjected to suction filtration. The filtrate was diluted with water. The residue was dissolved in hot toluene and washed with celite, alumina, and ethanol. The resulting solution was concentrated to dryness and then filtered with toluene. The target compound was obtained in an amount of 14.7 g (yield 85%, pale yellow solid) by recrystallization at 1000 rpm. The synthetic scheme of step 1 is shown in formula (f-1) below.

[0419] [ka]

[0420] <Step 2: Synthesis of 8βN-4mDBtBPBfpm> Next, 8-chloro-4-[3'-(dibenzothiophene-4- 7.01g , naphthalene-2-boronic acid 3.13g, cesium fluoride 5.93g, mesitylene 130 The mixture was stirred under reduced pressure to degas it and replaced with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) 0.3 58g, 2'-(dicyclohexylphosphino)acetophenone ethylene ketal 0.2 The mixture was stirred at 120° C. for 17.5 hours. acetone)dipalladium(0) 0.358g, 2'-(dicyclohexylphosphino)a 0.282 g of cetophenone ethylene ketal was added, and the mixture was stirred at 120° C. for 16 hours.

[0421] Water was added to the reaction mixture, which was then filtered under suction. The residue was washed with water and ethyl acetate. The residue was dissolved in hot toluene and packed in the following order: Celite, alumina, and Celite. The resulting solution was concentrated to dryness and recrystallized from toluene to obtain the product. 6.75 g of the invention 8βN-4mDBtBPBfpm (abbreviation) was obtained (yield: 82%, white 2.47 g of this white solid was purified by train sublimation. The conditions for sublimation purification were: pressure 3.7 Pa, argon gas flow rate 15 mL / min, The solid was heated at 340°C. After purification by sublimation, 2.20g of the target light brown solid was obtained, with a recovery rate of 89%. %. The synthesis scheme of step 2 is shown in formula (f-2) below.

[0422] [ka]

[0423] The light brown solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in Figure 32. It was found that N-4mDBtBPBfpm was obtained.

[0424] 1 H-NMR.δ(CDCl3):7.46-7.57(m,4H),7.61-7.6 3(m,2H),7.70(t,1H),7.76(t,1H),7.79-7.83( m,3H),7.86(d,2H),7.91-7.95(m,3H),8.00(d, 1H),8.05(d,1H),8.18(d,2H),8.21-8.24(m,2H ), 8.65-8.66 (m, 2H), 8.99 (s, 1H), 9.33 (s, 1H). EXAMPLES

[0425] In this example, the 8αN-4 Light-emitting device 6 using mDBtPBfpm (structural formula (103)) in the light-emitting layer, as described in Example 8 The light-emitting device uses 8βN-4mDBtBPBfpm (structural formula (116)) as the light-emitting layer. 7 were fabricated and the characteristics were measured.

[0426] The element structure of the light-emitting element used in this embodiment is the same as that shown in FIG. 18 in the fourth embodiment. However, the specific configuration of each layer that constitutes the element structure is as shown in Table 5. The chemical formulas of the materials used in this example are shown below.

[0427] [Table 5]

[0428] [ka]

[0429] <Operation characteristics of light-emitting element> The operating characteristics of the fabricated light-emitting elements 6 and 7 were measured. The results are shown in Figures 33 to 36.

[0430] Also, 1000cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 6 below. .

[0431] [Table 6]

[0432] From the above results, it is understood that each light-emitting element fabricated in this example exhibits excellent element characteristics.

[0433] In addition, each light-emitting element is supplied with 2.5mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 37, the emission spectrum of each light-emitting element is 558n m, and the [Ir(ppy)2(4dpp y)].

[0434] Next, a reliability test was performed on the light-emitting element 6 and the light-emitting element 7. The results of the reliability test are shown in FIG. In FIG. 38, the vertical axis represents normalized luminance (%) when the initial luminance is 100%. The horizontal axis indicates the operation time (h) of the element. The reliability test was performed at a constant current of 2 mA. A driving test was carried out.

[0435] From the results of the reliability test, it was found that both the light-emitting element 6 and the light-emitting element 7, which are embodiments of the present invention, It was found that the device exhibited excellent reliability. The organic compounds 8αN-4mDBtPBfpm (structural formula (103)) and 8βN-4mD The use of BtBPBfpm (structural formula (116)) is useful for extending the life of light-emitting devices. In addition, the results of this example show that the benzofuropyrimidine skeleton or the benzothiamine skeleton Direct bonding of a condensed ring to the benzene side of the enopyrimidine skeleton leads to a longer life for the device. It turns out that there is a direct connection. EXAMPLES

[0436] In this embodiment, the 8DBt- A light-emitting device 8 was fabricated using 2mDBtPBfpm (structural formula (145)) in the light-emitting layer. The results of measuring the characteristics are shown below.

[0437] The element structure of the light-emitting element used in this embodiment is the same as that shown in FIG. 18 in the fourth embodiment. However, the specific configuration of each layer that constitutes the element structure is as shown in Table 7. The chemical formulas of the materials used in this example are shown below.

[0438] [Table 7]

[0439] [ka]

[0440] <Operation characteristics of light-emitting element> The operating characteristics of the fabricated light-emitting element 8 were measured. The measurements were carried out at room temperature. The results are shown in FIG. 39 to 42.

[0441] Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 8 in the vicinity are shown in Table 8 below. .

[0442] [Table 8]

[0443] From the above results, it is understood that the light-emitting element 8 fabricated in this example exhibits excellent element characteristics.

[0444] In addition, the light emitting element 8 is rated at 2.5 mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 43, the emission spectrum of the light-emitting element 8 has a peak at about 524 nm. The peak is the peak of [Ir(ppy)2(mdppy)] contained in the light-emitting layer 913. This suggests that it is due to luminescence. EXAMPLES

[0445] <Synthesis Example 7> In this synthesis example, the organic compound 8-(dibenzothiophene-4-yl) )-4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]-[1]be N-benzofuro[3,2-d]pyrimidine (abbreviation: 8DBt-4mDBtBPBfpm) (structure The synthesis method of formula (151) is explained. Structure of 8DBt-4mDBtBPBfpm The formula is shown below.

[0446] [ka]

[0447] 8-Chloro-4-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]- [1] Benzofuro[3,2-d]pyrimidine 7.00g, dibenzothiophene-4-boro 3.56g 2'-(dicyclohexylphosphino)acetophenone ethylene ketate Put 0.281 g of ruthenium, 6.00 g of cesium fluoride, and 65 mL of mesitylene into a three-neck flask. The mixture was stirred under reduced pressure to degas it, and the atmosphere was replaced with nitrogen. Add 0.359 g of dipalladium(0) (Pd2(dba)3) in acetone and heat at 120°C. The mixture was stirred for 1 hour. 65 mL of degassed mesitylene was added to the mixture, and the mixture was heated at 120°C for 9.5 hours. The mixture was stirred for 1 hour. 30 mL of degassed mesitylene was added to the mixture and heated at 120°C for 7 hours. The mixture was stirred for 1 h. Add 0.284 g of arylphosphinoacetophenone ethylene ketal and heat at 130°C for 15 hours. The mixture was stirred for 1 hour and then at 140° C. for 6 hours. Dibenzothiophene-4-boronic acid 2.37g, Pd2(dba)30.359g, 2'-(dicyclohexylphosphino ) 0.283 g of acetophenone ethylene ketal was added, and the mixture was stirred at 140° C. for 40 hours. Water was added to the reaction mixture, which was then filtered under suction. The residue was washed with water and ethyl acetate. The residue was dissolved in hot toluene and packed in the following order: Celite, alumina, and Celite. The resulting solution was concentrated to dryness and recrystallized from toluene to give 8. 5.56 g of DBt-4mDBtBPBfpm (abbreviation) was obtained (yield: 62%, white solid). 1.95 g of this white solid was purified by train sublimation. The production conditions were a pressure of 2.8 Pa, argon gas flow rate of 15 mL / min, and 355 The solid was heated at 50°C. After purification by sublimation, 1.46 g of the target light brown solid was obtained with a recovery rate of 75%. The synthesis scheme is shown in the following formula (g-1).

[0448] [ka]

[0449] The light brown solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis results As shown below, it was found that 8DBt-4mDBtBPBfpm was obtained. .

[0450] 1 H-NMR.δ(CDCl3):7.47-7.51(m,4H),7.59-7.6 5(m,4H),7.70(t,1H),7.76-7.87(m,6H),7.95( d,1H),8.09(d,1H),8.21-8.24(m,5H),8.66-8. 68(m,2H),9.01(s,1H),9.34(s,1H). [Explanation of symbols]

[0451] 101 First electrode 102 Second electrode 103 EL layer 103a, 103b, 103c EL layer 104 Charge generating layer 111, 111a, 111b Hole injection layer 112, 112a, 112b hole transport layer 113, 113a, 113b, 113c Light-emitting layer 114, 114a, 114b electron transport layer 115, 115a, 115b electron injection layer 200R, 200G, 200B optical distance 201 First Substrate 202 Transistor (FET) 203R, 203G, 203B, 203W Light emitting element 204 EL layer 205 Second Board 206R, 206G, 206B Color Filters 206R', 206G', 206B' Color filters 207 First Electrode 208 Second Electrode 209 Black layer (black matrix) 210R, 210G conductive layer 301 First Substrate 302 Pixel section 303 Driver circuit section (source line driver circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 Sealing material 306 Second Board 307 Wiring 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulation 315 EL layer 316 Second Electrode 317 Light-emitting element 318 Space 900 Substrate 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting Equipment 4001 Substrate 4002 Light emitting element 4003 Substrate 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulation layer 4011 Sealing substrate 4012 Sealing material 4013 Desiccant 4015 Diffuser 4100 Lighting equipment 4200 Lighting Equipment 4201 Substrate 4202 Light emitting element 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 4212 Sealing material 4213 Barrier film 4214 Planarization film 4215 Diffuser 4300 Lighting Equipment 5101 Light 5102 Wheels 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner rear view mirror 7000 Chassis 7001 Display section 7002 2nd display section 7003 Speaker 7004 LED Lamp 7005 Operation key 7006 Connection terminal 7007 Sensor 7008 Microphone 7009 Switch 7010 Infrared port 7011 Recording medium reading unit 7012 Support part 7013 Earphones 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7019 Microphone 7020 Camera 7021 External connection part 7022, 7023 Operation buttons 7024 Connection terminal 7025 Band 7026 Clasp 7027 Time Icon 7028 Other Icons 8001 Lighting equipment 8002 Lighting equipment 8003 Lighting equipment 8004 Lighting equipment 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 Case

Claims

1. An organic compound represented by formula (G3): 【Chemistry 1】 (In the formula, Q represents oxygen or sulfur, α represents an arylene group having 6 to 13 carbon atoms which may have a substituent, and n represents an integer of 0 to 4. １ R represents any one of an aryl group having 6 to 18 carbon atoms which may have a substituent and a heteroaryl group having 6 to 18 carbon atoms which may have a substituent. １ represents hydrogen, R ２ ~R ４ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, and an aryl group having 6 to 13 carbon atoms which may have a substituent. ２ represents a fused ring which may have a substituent. In the case where the ring may have a substituent, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

2. An organic compound represented by formula (G4): 【Chemistry 2】 (In the formula, Q represents oxygen or sulfur, α represents an arylene group having 6 to 13 carbon atoms which may have a substituent, and n represents an integer of 0 to 4. １ R represents any one of an aryl group having 6 to 18 carbon atoms which may have a substituent and a heteroaryl group having 6 to 18 carbon atoms which may have a substituent. １ represents hydrogen, R ２ ~R ４ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, and an aryl group having 6 to 13 carbon atoms which may have a substituent. ３ represents a fused ring which may have a substituent. In the case where the ring may have a substituent, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

3. An organic compound represented by formula (G6): 【Chemistry 3】 (In the formula, Q represents oxygen or sulfur, α represents an arylene group having 6 to 13 carbon atoms which may have a substituent, and n represents an integer of 0 to 4. １ R represents any one of an aryl group having 6 to 18 carbon atoms which may have a substituent and a heteroaryl group having 6 to 18 carbon atoms which may have a substituent. １ represents hydrogen, R ２ ~R ４ each independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, and an aryl group having 6 to 13 carbon atoms which may have a substituent. ４ represents a fused ring which may have a substituent. In the case where the ring may have a substituent, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

4. In any one of claims 1 to 3, A １ has a diarylamino group which may have a substituent, and in the case where the group may have a substituent, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

5. In any one of claims 1 to 3, A １ has a fused aromatic hydrocarbon ring which may have a substituent, and in the case where the ring is optionally substituted, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

6. In any one of claims 1 to 3, A １ is an organic compound which is a fused heteroaromatic ring which has any one of a dibenzothiophene skeleton, a dibenzofuran skeleton, and a carbazole skeleton and which may have a substituent, and in the case where the ring is optionally substituted, the substituent is any one of an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an aryl group having 6 to 12 carbon atoms.

7. In any one of claims 1 to 6, α is an organic compound represented by any one of the following general formulas (Ar-1) to (Ar-18). 【Chemistry 4】

8. An organic compound represented by any one of formulas (100), (101), (102), (145), (103), (116) and (151). 【Chemistry 5】 【Chemistry 6】

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