Light-emitting element, light-emitting device, electronic device and lighting device

Abstract

To provide a novel organic compound, a furopyrazine derivative.SOLUTION: An organic compound has a furopyrazine skeleton and is represented by the following general formula (G1). In the general formula (G1), Q represents oxygen or sulfur. Ar1 represents a substituted or unsubstituted condensed aromatic ring. R1 and R2 each independently represent hydrogen or a group having a total of 1 to 100 carbon atoms, and at least one of R1 and R2 has a hole-transporting skeleton.SELECTED DRAWING: None

Description

[Technical field]

[0001] One embodiment of the present invention relates to an organic compound, a light-emitting element, a light-emitting device, an electronic device, and a lighting device. However, one 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]

[0002] 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.

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

[0004] Many types of organic compounds and their synthesis methods have been developed to date. There are various applications and development fields. In the biochemical field, naphthofuropyrazine bone Methods for easily synthesizing substances having this property have been reported (for example, see Non-Patent Document 1). .

[0005] However, new substances have been developed using substances with this naphthofuropyrazine skeleton as raw materials. There have been no reports of this happening. [Prior art documents] [Non-patent literature]

[0006] [Non-Patent Document 1] K.Shiva Kumar, Raju Adepu, Ravikumar Kapavarapu, D.Rambabu, G.Rama Krishna, C.Malla Reddy, K.KrishnaPriya, KishoreV.L.Parsa, Manojit Pal, "AlCl3 induced C-arylation / cyclization in a single pot: a new route to benzofuran fused N-heterocycles of pharmacological interest", Tetrahedron Letters, 2012, Vol.53, p.1134-1138 Summary of the Invention [Problem to be solved by the invention]

[0007] Therefore, in one embodiment of the present invention, a compound having a furopyrazine skeleton (including naphthofuropyrazine) is In another aspect of the present invention, a novel organic compound is provided. A furopyrazine derivative, which is an organic compound, is provided. In addition, in one embodiment of the present invention, a novel organic compound that can be used for a light-emitting element is provided. The present invention provides a novel organic compound that can be used in the EL layer of the device. The present invention provides a novel light-emitting element having high reliability using a novel organic compound. The present invention provides a light-emitting device, a novel electronic device, or a novel lighting device. The above does not necessarily preclude the existence of other problems. It is not necessary to solve all of these problems. Problems other than these may be solved by the specification, drawings, claims, etc. It is obvious from the description of the specification, drawings, claims, etc. From this, it is possible to extract other issues. [Means for solving the problem]

[0008] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0009] [ka]

[0010] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or represents an unsubstituted condensed aromatic ring. 1 and R 2 are each independently hydrogen or total R represents a group having 1 to 100 carbon atoms; 1 and R 2 At least one of the above has a hole transporting skeleton. Yes.

[0011] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0012] [ka]

[0013] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted It also indicates one of the following: 1 and R 2 are each independently hydrogen or or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of the above is a hole transporting Has a skeleton.

[0014] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0015] [ka]

[0016] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or represents an unsubstituted condensed aromatic ring. 1 and R 2 are each independently hydrogen or total R represents a group having 1 to 100 carbon atoms; 1 and R 2 At least one of the groups is a group containing a condensed ring. do.

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

[0018] [ka]

[0019] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted It also indicates one of the following: 1 and R 2 are each independently hydrogen or or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of the groups contains a fused ring. It is based on

[0020] In the above general formula (G1), Ar 1 is represented by the following general formula (t1) to general formula (t3): The present invention is characterized in that the present invention is represented by any one of the following:

[0021] [ka]

[0022] In the above general formulas (t1) to (t3), R 3 ~R 24 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted alkyl group having 3 a cycloalkyl group having 6 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; In addition, * represents a bonding site in general formula (G1).

[0023] In each of the above structures, the general formula (G1) is represented by the following general formulas (G1-1) to (G1-2): The present invention is characterized in that the compound is any one of (G1-4).

[0024] [ka]

[0025] In the above general formulae (G1-1) to (G1-4), Q represents oxygen or sulfur. Also, R 1 and R 2 each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; , R 1 and R 2 At least one of R has a hole transporting skeleton. 3 ~R 8 Oh BiR 17 ~R 24 each independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted alkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; represents any one of unsubstituted aryl groups having 6 to 30 carbon atoms.

[0026] In each of the above structures, the hole transporting skeleton is a substituted or unsubstituted diaryl amine. a substituted or unsubstituted condensed aromatic hydrocarbon ring, or a substituted or unsubstituted π-excess and a condensed heteroaromatic ring of the type.

[0027] In some of the above-mentioned structures, the fused ring is a substituted or unsubstituted fused aromatic hydrocarbon ring. or a substituted or unsubstituted π-excessive condensed heteroaromatic ring. The condensed ring is a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carboxylate skeleton. A substituted or unsubstituted condensed heteroaromatic ring having one of the rutile skeletons. The condensed ring is a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, or a phenanthrene skeleton, It is characterized by being a hydrocarbon ring.

[0028] In each of the above structures, R in the general formula (G1) 1 and R 2 are each independently , hydrogen or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of the following: It is characterized in that it is a group represented by general formula (u1).

[0029] [ka]

[0030] In the above general formula (u1), α represents a substituted or unsubstituted arylene having 6 to 25 carbon atoms. group, and n represents an integer of 0 to 4. 1 is a substituted or unsubstituted cyclic alkyl group with a total of 6 to 30 carbon atoms. Unsubstituted aryl group, or substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms In addition, * represents a bonding site in general formula (G1).

[0031] In addition, A in the above general formula (u1) 1 is represented by the following general formula (A 1 -1) to general formula (A 1 -17 ) is any one of the above.

[0032] [ka]

[0033] 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 3 carbon atoms; 0 aryl groups.

[0034] In addition, α in the above general formula (u1) is represented by the following general formulas (Ar-1) to (Ar-14): The present invention is characterized in that the present invention is any one of the above.

[0035] [ka]

[0036] In the above general formulae (Ar-1) to (Ar-14), R B1 ~R B14 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 3 carbon atoms; 0 aryl groups.

[0037] Another embodiment of the present invention is a compound represented by the structural formula (100), (123), (125), or (126): , (133), (156), (208), (238), (239), (244), (24 It is an organic compound represented by either (5) or (246).

[0038] [ka]

[0039] In addition, a novel useful compound that can be used as a raw material for synthesizing the organic compound according to one embodiment of the present invention can be used. The present invention also includes the organic compound (see embodiment 1). The light-emitting element includes an organic compound according to one embodiment of the present invention. In addition, the present invention also includes light-emitting devices having guest materials.

[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 light-emitting element, a layer having an organic compound (e.g., a cap layer) is provided in contact with the electrode. In addition to the light emitting element, a transistor is also included in the present invention. The scope of the invention also includes light-emitting devices having a photodiode, a substrate, etc. microphone, camera, operation buttons, external connectors, housing, cover, support base, or speaker. Electronic devices and lighting devices having a power source are also included in the scope of the invention.

[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] In one embodiment of the present invention, a substance having a furopyrazine skeleton (including naphthofuropyrazine) is used as a raw material. In another embodiment of the present invention, a novel organic compound can be provided. It is possible to provide a novel organic compound, a furopyrazine derivative. In this manner, a novel organic compound that can be used in a light-emitting element can be provided. In one embodiment of the present invention, a novel organic compound that can be used in an EL layer of a light-emitting element is provided. In addition, a novel light-emitting device with high reliability using the novel organic compound according to one embodiment of the present invention is provided. In addition, a novel light-emitting device, a novel electronic device, or a novel lighting device can be provided. The description of these effects does not preclude the existence of other effects. It is not necessary for one embodiment of the present invention to have all of these effects. Effects other than those mentioned above are obvious from the description, drawings, claims, etc. Other effects can be extracted from the description in the specification, drawings, claims, etc. It is possible. [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] 1A to 1C are diagrams illustrating light-emitting elements. [Figure 12] FIG. 13 shows current density-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 13] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 14] FIG. 13 shows luminance-current efficiency characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 15] FIG. 13 shows voltage-current characteristics of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 16] FIG. 1 shows emission spectra of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 17] 13 shows the reliability of the light-emitting element 1 and the comparative light-emitting element 2. [Figure 18] FIG. 13 shows current density-luminance characteristics of the light-emitting element 3. [Figure 19] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 3. [Figure 20] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 3. [Figure 21] FIG. 13 shows voltage-current characteristics of the light-emitting element 3. [Figure 22] FIG. 2 shows an emission spectrum of the light-emitting element 3. [Figure 23] FIG. 13 shows the reliability of the light-emitting element 3. [Figure 24] FIG. 13 shows current density-luminance characteristics of the light-emitting element 4. [Diagram 25] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 4. [Figure 26] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 4. [Figure 27] FIG. 13 shows voltage-current characteristics of the light-emitting element 4. [Figure 28] FIG. 13 shows an emission spectrum of the light-emitting element 4. [Figure 29] FIG. 13 shows the reliability of the light-emitting element 4. [Diagram 30] FIG. 13 shows current density-luminance characteristics of the light-emitting element 5. [Diagram 31] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 5. [Diagram 32] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 5. [Diagram 33] FIG. 13 shows voltage-current characteristics of the light-emitting element 5. [Diagram 34] FIG. 4 shows an emission spectrum of the light-emitting element 5. [Diagram 35] FIG. 13 shows the reliability of the light-emitting element 5. [Diagram 36] 1H-NMR chart of the organic compound shown in structural formula (123). [Figure 37] 1H-NMR chart of the organic compound shown in structural formula (125). [Figure 38] 1H-NMR chart of the organic compound shown in structural formula (126). [Figure 39] 1H-NMR chart of the organic compound shown in structural formula (133). [Diagram 40] 1H-NMR chart of the organic compound shown in structural formula (156). [Diagram 41] 1H-NMR chart of the organic compound shown in structural formula (208). [Diagram 42] 1H-NMR chart of the organic compound shown in structural formula (238). [Diagram 43] 1H-NMR chart of the organic compound shown in structural formula (239). [Diagram 44] 1H-NMR chart of the organic compound shown in structural formula (244). [Diagram 45] 1H-NMR chart of the organic compound shown in structural formula (245). [Figure 46] 1H-NMR chart of the organic compound shown in structural formula (246). [Figure 47] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 8. [Figure 48] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 8. [Figure 49] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 8. [Figure 50] FIG. 13 is a graph showing voltage-current characteristics of the light-emitting element 8. [Figure 51] FIG. 2 shows an emission spectrum of the light-emitting element 8. [Figure 52] FIG. 13 shows the reliability of the light-emitting element 8. [Diagram 53] FIG. 13 is a graph showing current density-luminance characteristics of the light-emitting element 9. [Figure 54] FIG. 13 is a graph showing voltage-luminance characteristics of the light-emitting element 9. [Figure 55] FIG. 13 shows luminance vs. current efficiency characteristics of the light-emitting element 9. [Figure 56] FIG. 13 is a graph showing voltage-current characteristics of the light-emitting element 9. [Figure 57] FIG. 2 shows an emission spectrum of the light-emitting element 9. [Figure 58] FIG. 13 is a graph showing the reliability of the light-emitting element 9. [Figure 59] FIG. 13 is a graph showing current density-luminance characteristics of light-emitting elements 10 to 15. [Figure 60] FIG. 13 is a graph showing voltage-luminance characteristics of light-emitting elements 10 to 15. [Figure 61] FIG. 13 shows luminance-current efficiency characteristics of light-emitting elements 10 to 15. [Figure 62] FIG. 13 is a graph showing voltage-current characteristics of light-emitting elements 10 to 15. [Figure 63] FIG. 1 shows emission spectra of light-emitting elements 10 to 15. [Figure 64] FIG. 1 shows the reliability of light-emitting elements 10 to 15. [Figure 65] FIG. 13 shows current density-luminance characteristics of the light-emitting element 16 and the comparative light-emitting element 17. [Figure 66] FIG. 13 shows voltage-luminance characteristics of the light-emitting element 16 and the comparative light-emitting element 17. [Figure 67] FIG. 13 shows luminance-current efficiency characteristics of the light-emitting element 16 and the comparative light-emitting element 17. [Figure 68] 13 shows voltage-current characteristics of the light-emitting element 16 and the comparative light-emitting element 17. [Figure 69] FIG. 13 shows emission spectra of the light-emitting element 16 and the comparative light-emitting element 17. [Figure 70] 13 shows the reliability of the light-emitting element 16 and the comparative light-emitting element 17. 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 to those described above 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 used commonly even among different drawings.

[0047] (Embodiment 1) In this embodiment, an organic compound according to one embodiment of the present invention will be described. The organic compound according to one embodiment has a naphthofuropyrazine skeleton and is represented by the following general formula (G1): can be.

[0048] [ka]

[0049] In the general formula (G1), Q represents oxygen or sulfur. 1 If you replace R represents an unsubstituted condensed aromatic ring. 1 and R 2 are each independently hydrogen or R represents a group having a total of 1 to 100 carbon atoms; 1 and R 2 At least one of the structures has a hole transporting structure. has.

[0050] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0051] [ka]

[0052] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted It also indicates one of the following: 1 and R 2 are each independently hydrogen or or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of the above is a hole transporting Has a skeleton.

[0053] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0054] [ka]

[0055] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or represents an unsubstituted condensed aromatic ring. 1 and R 2 are each independently hydrogen or total R represents a group having 1 to 100 carbon atoms; 1 and R 2 At least one of the groups is a group containing a condensed ring. do.

[0056] Another embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0057] [ka]

[0058] In the above general formula (G1), Q represents oxygen or sulfur. 1 is replaced or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted It also indicates one of the following: 1 and R 2 are each independently hydrogen or or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of the groups contains a fused ring. It is based on

[0059] In the above general formula (G1), Ar 1 is represented by the following general formula (t1) to general formula (t3): It is represented by one of the following.

[0060] [ka]

[0061] In the above general formulas (t1) to (t3), R 3 ~R 24 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted alkyl group having 3 a cycloalkyl group having 6 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; In addition, * represents a bonding site in general formula (G1).

[0062] In each of the above structures, the general formula (G1) is represented by the following general formulas (G1-1) to (G1-2): (G1-4) is any one of them.

[0063] [ka]

[0064] In the above general formulae (G1-1) to (G1-4), Q represents oxygen or sulfur. Also, R 1 and R 2 each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; , R 1 and R 2 At least one of R has a hole transporting skeleton. 3 ~R 8 Oh BiR 17 ~R 24 each independently represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted alkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; represents any one of unsubstituted aryl groups having 6 to 30 carbon atoms.

[0065] In addition, in each of the above configurations, R 1 and R 2 At least one of the hole transporting skeletons has , a substituted or unsubstituted diarylamino group, a substituted or unsubstituted condensed aromatic hydrocarbon ring, or a substituted or unsubstituted π-excessive condensed heteroaromatic ring. The aromatic hydrocarbon ring is a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, or It is preferable that the π-excess type condensed complex has at least one of the following structure: The aromatic ring is a dibenzothiophene skeleton, a dibenzofuran skeleton, or a carbazole skeleton. It is preferable that the condensed heteroaromatic ring has any one of the following: Not only benzocarbazole, dibenzothiophene, and dibenzofuran, but also Zocarbazole, indolocarbazole, benzoindolocarbazole, dibenzoindo Benzindolylcarbazole, benzindolylbenzocarbazole, benzonaphthothiophene, benzo Like naphthofuran, the ring structure contains a carbazole skeleton, a dibenzothiophene skeleton, or Condensed rings with a dibenzofuran skeleton (i.e., carbazole skeleton, dibenzothiophene This also includes dibenzofuran skeletons and fused rings formed by further condensing a ring to the dibenzofuran skeleton.

[0066] In addition, in each of the above configurations, R 1 and R 2 At least one of the fused rings may be substituted or unsubstituted. or unsubstituted condensed aromatic hydrocarbon rings, or substituted or unsubstituted π-excessive condensed heterocyclic rings. In particular, the condensed ring is one of a naphthalene skeleton, a fluorene skeleton, a thiazolinone skeleton, and an aromatic ring. A substituted or unsubstituted aryl group having either a phenylene skeleton or a phenanthrene skeleton. It is preferable that the fused ring is a substituted fused aromatic hydrocarbon ring. a substituent having any one of an olefin skeleton, a dibenzofuran skeleton, and a carbazole skeleton; The fused heteroaromatic ring is preferably a substituted or unsubstituted fused heteroaromatic ring. Not only benzocarbazole, dibenzothiophene, and dibenzofuran, but also Zocarbazole, indolocarbazole, benzoindolocarbazole, dibenzoindo Benzindolylcarbazole, benzindolylbenzocarbazole, benzonaphthothiophene, benzo Like naphthofuran, the ring structure contains a carbazole skeleton, a dibenzothiophene skeleton, or Condensed rings with a dibenzofuran skeleton (i.e., carbazole skeleton, dibenzothiophene This also includes dibenzofuran skeletons and fused rings formed by further condensing a ring to the dibenzofuran skeleton.

[0067] In each of the above structures, R in the general formula (G1) 1 and R 2 are each independently , hydrogen or a group having a total of 1 to 100 carbon atoms; R 1 and R 2 At least one of the following: It is a group represented by general formula (u1).

[0068] [ka]

[0069] In the above general formula (u1), α represents a substituted or unsubstituted arylene having 6 to 25 carbon atoms. group, and n represents an integer of 0 to 4. 1 is a substituted or unsubstituted cyclic alkyl group with a total of 6 to 30 carbon atoms. Unsubstituted aryl group, or substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms Represents a group.

[0070] In addition, A in the above general formula (u1) 1 is a substituted or unsubstituted aryl group with a total of 6 to 30 carbon atoms. or a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms, Specifically, the compound represented by the following general formula (A 1 -1) to general formula (A 1 -17) It is characterized by:

[0071] [ka]

[0072] 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 3 carbon atoms; 0 aryl groups.

[0073] In addition, α in the above general formula (u1) is represented by the following general formulas (Ar-1) to (Ar-14): The present invention is characterized in that the present invention is any one of the above.

[0074] [ka]

[0075] In the above general formulae (Ar-1) to (Ar-14), R B1 ~R B14 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 3 carbon atoms; 0 aryl groups.

[0076] In addition, in the above general formula (G1) and the above general formulae (G1-1) to (G1-4), R 1 and R 2 The group having a total of 1 to 100 carbon atoms is a substituted or unsubstituted carbon atom. an alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and heteroaryl groups having a carbon number of 3 to 30. 1 and R 2 At least One has a hole transport skeleton or fused ring as described above.

[0077] In the above general formula (G1), the substituted or unsubstituted fused aromatic ring has a substituent. In the above general formula (G1), the substituted or unsubstituted naphthalene, Substituted or unsubstituted phenanthrene and substituted or unsubstituted chrysene have a substituent. In the case of the above general formula (t1) to general formula (t3), an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; or when the substituted or unsubstituted aryl group having 6 to 30 carbon atoms has a substituent, or substituted or unsubstituted in the above general formulae (G1-1) to (G1-4). an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; or when the substituted or unsubstituted aryl group having 6 to 30 carbon atoms has a substituent, or a substituted or unsubstituted fused aromatic hydrocarbon ring in the above general formula (G1), In the case where the substituted or unsubstituted π-excessive condensed heteroaromatic ring has a substituent, In the general formula (u1), a substituted or unsubstituted arylene group having 6 to 25 carbon atoms in total A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having a total of 3 to 30 carbon atoms Alternatively, the unsubstituted heteroaryl group may have a substituent, or the above general formula (Ar- 1) to the general formula (Ar-14), a substituted or unsubstituted alkyl group having 3 to 7 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms; When the substituted aryl group having 6 to 30 carbon atoms has a substituent, or when the substituted aryl group is represented by the above general formula (G1 ), and R in the above general formulae (G1-1) to (G1-4)1 and R 2 has Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms in a group having 1 to 100 carbon atoms in total , a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted carbon an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; In the case where the alkyl group has a substituent, the substituent is a methyl group, an ethyl group, a propyl group, an iso ... Propyl, butyl, isobutyl, sec-butyl, tert-butyl, butyl alkyl groups having 1 to 7 carbon atoms, such as cyclopentyl and cyclohexyl groups; 5 carbon atoms such as xyl group, cycloheptyl group, and 8,9,10-trinorbornanyl group. Cycloalkyl groups with carbon atoms up to 7, such as phenyl, naphthyl, and biphenyl groups, Examples of the aryl groups include aryl groups having the formula:

[0078] In addition, the above general formulae (t1) to (t3) and the above general formulae (G1-1) to (G 1-4), or the general formula (A 1 -1) to general formula (A 1 -17) having 1 to 6 carbon atoms Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a bromo group. butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, isopentyl group ethyl group, sec-pentyl group, tert-pentyl group, neopentyl group, hexyl group, isopropyl group, isohexyl group, 3-methylpentyl group, 2-methylpentyl group, 2-ethylbutyl group, 1 Examples of the aryl group include a 2-dimethylbutyl group, a 2,3-dimethylbutyl group, and an n-heptyl group.

[0079] In addition, the above general formulae (t1) to (t3) and the above general formulae (G1-1) to (G 1-4), or the general formula (A 1 -1) to general formula (A 1 -17) with 3 to 7 carbon atoms Specific examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group. cyclohexyl, 1-methylcyclohexyl, 2,6-dimethylcyclohexyl Examples include a sil group, a cycloheptyl group, and a cyclooctyl group.

[0080] In addition, the above general formulae (t1) to (t3) and the above general formulae (G1-1) to (G 1-4), or the general formula (A 1 -1) to general formula (A 1 -17) with 6 to 3 carbon atoms Specific examples of the aryl group of 0 include a phenyl group, an o-tolyl group, an m-tolyl group, and a p-tolyl group. biphenyl, mesityl, o-biphenyl, m-biphenyl, p-biphenyl, 1-naphthalene Fluorenyl group, 2-naphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, Spirof Examples of the alkyl group include a fluorenyl group, a phenanthrenyl group, an anthracenyl group, and a fluoranthenyl group. can be.

[0081] In addition, in the above general formula (G1) and the above general formulae (G1-1) to (G1-4), R 1 and R 2 Aryl groups having 6 to 30 carbon atoms in the group having a total of 1 to 100 carbon atoms. Specific examples of the tolyl group include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, and a mesylate group. o-biphenyl group, m-biphenyl group, p-biphenyl group, 1-naphthyl group, 2 -Naphthyl group, fluorenyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, etc. , R 1 and R2 In the group having a total of 1 to 100 carbon atoms, Specific examples of the aryl group include carbazole, benzocarbazole, and dibenzocarbazo. Indolocarbazole, benzoindolocarbazole, dibenzoindolocarbazole benzoindol, benzindolobenzcarbazole, dibenzothiophene, benzonaphthothiophene Examples of monovalent groups include benzofuran, dibenzofuran, and benzonaphthofuran.

[0082] 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.

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] The organic compounds represented by the above structural formulas (100) to (251) are represented by the above general formula (G1) However, the organic compound according to one embodiment of the present invention is not limited to this. I can't.

[0098] Next, a method for synthesizing an organic compound represented by the following general formula (G1'), which is one embodiment of the present invention, An example will be described. The organic compound represented by the following general formula (G1′) is a condensed aromatic Furopyrazine derivatives with condensed rings or thienopyrazine derivatives with condensed aromatic rings. This is one embodiment of the organic compound represented by general formula (G1) above.

[0099] [ka]

[0100] In the general formula (G1′), Q represents oxygen or sulfur. 1 is a carbon number of 1 to 100 represents a group, R 1 represents a hole transporting skeleton. 1 is a substituted or unsubstituted abbreviation Represents a synthetic aromatic ring.

[0101] <Method for synthesizing organic compound represented by general formula (G1')> Various reactions can be applied to synthesize the organic compound represented by the above general formula (G1'). For example, a compound represented by the general formula (G1') can be prepared by a simple method shown in the following synthesis scheme. Organic compounds can be synthesized.

[0102] First, as shown in the following scheme (A-1), The arylboronic acid (a1) and the pyrazine derivative (a2) substituted with an amino group and a halogen atom are a2) is coupled with the intermediate (a3) ​​to obtain the intermediate (a3), and then the intermediate (a3) ​​is reacted with nitrous acid t The condensed aromatic ring is condensed with ert-butyl, and the resulting cyclization gives a furopyrazine derivative. The thienopyrazine derivative (a4) having a condensed aromatic ring or a condensed aromatic ring is obtained. In the derivative (a4), Y 1 If is halogen, boron in aromatic ring containing halogen Acid (Y 3 -B 1 The intermediate (a5) obtained by coupling with the pyrazine derivative (a4) It can be used in the subsequent reaction in the same manner.

[0103] [ka]

[0104] In the synthesis scheme (A-1), Q represents oxygen or sulfur. 1 teeth, represents a substituted or unsubstituted condensed aromatic ring. 1 is a halogen or an aromatic compound containing a halogen It represents the fragrance ring, and Y 1 is one or two. Also, Y 2 represents a halogen. Also, Y 3 teeth represents an aromatic ring containing halogen, and Y 3 is one or two. Also, B 1 Boronic acid or represents a boronic acid ester or a cyclic triol borate salt, etc. As the phosphate salt, potassium salt and sodium salt may be used in addition to lithium salt.

[0105] In addition, in the above synthesis scheme (A-1), The organic compound is an organic compound according to one embodiment of the present invention, as shown in the following synthesis scheme (A-2). The organic compounds represented by the general formulas (a4) and (a5) are the raw materials for the new The organic compounds represented by the general formulas (a4) and (a5) are included in one embodiment of the present invention. The specific structural formula of the organic compound represented is shown below.

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] The organic compounds represented by the above structural formulas (300) to (347) are represented by the above general formula (a4) and (a5), which are examples of organic compounds represented by the formula (a1) and (a6). is not limited to this.

[0110] Next, as shown in the following scheme (A-2), the condensation reaction product obtained in the above scheme (A-1) is Furopyrazine derivatives with aromatic rings fused or thienopyrazine derivatives with fused aromatic rings The compound (a4) is coupled with a boronic acid compound (b1) to obtain a compound represented by the general formula ( G1') is obtained.

[0111] [ka]

[0112] In the synthesis scheme (A-2), Q represents oxygen or sulfur. 1 Charcoal represents the base of prime numbers 1 to 100, R 1 has a hole transporting skeleton. 1 Is, place represents a substituted or unsubstituted condensed aromatic ring. 1 represents one or two halogens, B 2 represents a boronic acid, a boronic acid ester, a cyclic triol borate salt, or the like. Cyclic triol borate salts can be prepared using potassium salts and sodium salts in addition to lithium salts. is also good.

[0113] In addition, the methyloxy group or the like used in the above synthesis schemes (A-1) and (A-2) or methylthio group-substituted arylboronic acid (a1), amino group- and halogen-substituted arylboronic acid (a2), The pyrazine derivative (a2) and the boronic acid compound (b1) are commercially available in various types. Since the fused aromatic ring represented by the above general formula (G1') is either present or can be synthesized, or a thienopyrazine derivative having a condensed aromatic ring condensed therein. Therefore, the organic compound according to one embodiment of the present invention is It is characterized by a wide variety of options.

[0114] The above is an embodiment of the present invention, which is a furopyrazine derivative having a fused aromatic ring or a fused aromatic ring. An example of an aromatic ring-condensed thienopyrazine derivative and a method for synthesizing the same have been described. The invention is not limited to this, and any other synthesis method may be used for synthesis.

[0115] 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.

[0116] The configuration described in this embodiment may be used in appropriate combination with the configurations described in other embodiments. can be done.

[0117] (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 it below.

[0118] <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 102. EL layer 103 is sandwiched between the insulating layer 102 and the insulating film 103 .

[0119] 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.

[0120] 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. .

[0121] 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.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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).

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] <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.

[0134] <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.

[0135] 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.

[0136] <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.

[0137] 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.

[0138] 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.

[0139] 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 a compound having a HOMO level that is the same as or close to the HOMO level.

[0140] 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 hexaazatriphenylene derivatives, chloranil derivatives, and 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 :HAT-CN) etc. can be used.

[0141] 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.

[0142] 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-fluorene- 2-yl)-9-phenyl-9H-carbazol-3-amine (abbreviation: PCBiF), N -(1,1'-biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazolyl)

[0046] -9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazole -3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl)- 4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: P CBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carba PCBNBB, 9,9-dimethyl-N -phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] PCBAF, N-phenyl-N-[4-(9-phenyl -9H-carbazol-3-yl)phenyl]spiro-9,9'-bifluorene-2-a PCBASF, 4,4',4''-tris(carbazol-9-yl) Triphenylamine (abbreviation: TCTA), 4,4',4''-tris(N,N-diphenyl amino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-( 3-Methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA ), compounds with aromatic amine skeletons such as 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 3 ,6-Bis(3,5-diphenylphenyl)-9-phenylcarbazole (abbreviation: CzT P), 3,3'-bis(9-phenyl-9H-carbazole) (abbreviation: PCCP), 3- [N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenyl Carbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole PCzPC A2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)a amino]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4 -(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10- (phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), etc. Compounds with a carbazole skeleton, such as 4,4',4''-(benzene-1,3,5-trimethylphenyl) yl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl- 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]dibenzothiophene DBTFLP-III, 4-[4-(9-phenyl-9H-fluorene-9 -yl)phenyl]-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV) Which compound has a thiophene skeleton, 4,4',4''-(benzene-1,3,5-trimethylphenyl) 4-{3-[3-(9-furanyl)tri(dibenzofuran)(abbreviation: DBF3P-II) mphenyl-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: Examples of compounds having a furan skeleton include compounds having a furan skeleton such as mDBFFLBi-II.

[0143] 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.

[0144] 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.

[0145] 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:

[0146] <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.

[0147] The light-emitting layers (113, 113a, 113b, 113c) are made of a light-emitting material (guest material). In addition, one or more organic compounds (host material, assist material) may be included. In addition, as the one or more kinds of organic compounds, the embodiment of the present invention shown in Embodiment 1 may be used. The organic compound may be any of the hole transporting materials and the electron transporting materials described in this embodiment. Or both may be used.

[0148] 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.

[0149] Examples of other light-emitting substances include the following:

[0150] 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).

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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:

[0155] For example, tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl )-4H-1,2,4-triazol-3-yl-κN2]phenyl-κC}iridium (III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5-methyl-3,4 -diphenyl-4H-1,2,4-triazolato)iridium(III) (abbreviation: [Ir (Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl-3-phenyl [Ir(iPrPrp tz-3b)3]), tris[3-(5-biphenyl)-5-isopropyl-4-phenyl Ir(iPr5b tz)3]), organometallic complexes with 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]) The organometallic complex fac-tris[1-(2,6-diisopropylphenyl)-2-phenyl [Ir(iPrpmi)3] ), tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f]furan [Phenanthridine]iridium(III) (abbreviation: [Ir(dmpimpt-Me)3] Organometallic complexes with imidazole skeletons such as bis[2-(4',6'-difluoro (phenyl)pyridinato-N,C 2’ ]Iridium(III) tetrakis(1-pyrazolyl) FIr6, bis[2-(4',6'-difluorophenyl)pyridine Zinat-N,C 2’ ]Iridium(III) picolinate (abbreviation: FIrpic), bis {2-[3',5'-bis(trifluoromethyl)phenyl]pyridinato-N,C 2’} Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]), Bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]iridium( III) Acetylacetonate (abbreviation: FIr(acac)) has an electron-withdrawing group Examples of such a complex include an organometallic complex having a phenylpyridine derivative as a ligand.

[0156] 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:

[0157] 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,C2’ ) 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.

[0158] 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:

[0159] 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)]), tris(4-t-butyl-6-phenyl Nylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)3]) A novel organometallic complex with a pyrimidine skeleton, (acetylacetonato)bis(2,3,5-tetraacetato) Triphenylpyrazinate)iridium(III) (abbreviation: [Ir(tppr)2(acac )]), bis(2,3,5-triphenylpyrazinate)(dipivaloylmethanato)iridine Ir(III) (abbreviation: [Ir(tppr)2(dpm)]), bis{4,6-dimethyl -2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]fu C}(2,6-dimethyl-3,5-heptanedionato-κ 2 O,O') Iridescent Ir(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]), bis{4,6 -Dimethyl-2-[5-(4-cyano-2,6-dimethylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethylphenyl Methyl-3,5-heptanedionate-κ 2 O,O') Iridium(III) (abbreviation: [I r(dmdppr-dmCP)2(dpm)]), (acetylacetonato)bis[2-methyl Chil-3-phenylquinoxalinato-N,C 2’ ]Iridium(III) (abbreviation: [Ir (mpq)2(acac)]), (acetylacetonato)bis(2,3-diphenylquinoline Xalinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(dpq)2(acac )]), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxa iridium(III) (abbreviation: [Ir(Fdpq)2(acac)]), bis{ 4,6-Dimethyl-2-[5-(5-cyano-2-methylphenyl)-3-(3,5-di methylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethylphenyl Methyl-3,5-heptanedionato-κ2O,O')iridium(III) (abbreviation: [I Organometallic compounds with pyrazine skeletons such as r(dmdppr-m5CP)2(dpm)] 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 2O,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)]).

[0160] 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 described in Embodiment 1 has a low LUMO level. It is suitable as a compound that easily receives a molecule.

[0161] 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.

[0162] 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 particular, the organic compound according to one embodiment of the present invention shown in Embodiment 1 may be selected. Since the triplet excited state is stable, the compound can be used as a host material when the light-emitting material is a phosphorescent material. In particular, the phosphorescent material is suitable for red emission due to its triplet excitation energy level. Other examples include zinc and aluminum metal complexes, as well as oxalate complexes. Sadiazole derivatives, triazole derivatives, benzimidazole derivatives, quinoxaline derivatives Conductors, dibenzoquinoxaline derivatives, dibenzothiophene derivatives, dibenzofuran derivatives , pyrimidine derivatives, triazine derivatives, pyridine derivatives, bipyridine derivatives, phenanthone In addition to thoroline derivatives, aromatic amines and carbazole derivatives are used as host materials. It is also possible.

[0163] More specifically, the host material may be, for example, the following hole transporting material and electron transporting material: can be used.

[0164] Examples of such host materials with high hole transport properties include N,N'-di(p-tolyl)-N ,N'-Diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis [N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: D PAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N ,N'-Diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTP) D) 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamine Examples of aromatic amine compounds include aromatic amine compounds such as diphenyl ether (DPA3B) and diphenyl ether (DPA3B).

[0165] 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.

[0166] 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-phenyl-N-phenylamino ',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.

[0167] As a host material having a high electron transporting property, for example, In addition to certain organic compounds, tris(8-quinolinolato)aluminum(III) (abbreviation: Al q), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Alm q3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)al bis(8-quinolinolato)zinc(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Metal complexes having a quinoline or benzoquinoline skeleton, such as Znq, In addition, bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: Z nPBO), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: Z Metal complexes with oxazole or thiazole ligands such as nBTZ can also be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butyl)- t-Butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD) and 1,3-biphenyl S[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl ]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadia oxazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO11) Diazole derivatives and 3-(4-biphenylyl)-4-phenyl-5-(4-tert- butylphenyl)-1,2,4-triazole (abbreviation: TAZ) Conductors and 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl- 1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene-4 -yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm -II) and other compounds having an imidazole skeleton (especially benzimidazole derivatives). , 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: Bz Os) and other compounds with an oxazole skeleton (especially benzoxazole derivatives), Sophenanthroline (abbreviation: Bphen), Bathocuproine (abbreviation: BCP), 2,9 -Bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2-[3-(dibenzothiophene) 2mDBTPDBq -II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]dibe Benzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-(9 H-Carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (Abbreviation: 2mCzBPDBq), 2-[4-(3,6-diphenyl-9H-carbazole -9-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 2CzPDBq-II I) 7-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quino Xaline (abbreviation: 7mDBTPDBq-II) and 6-[3-(dibenzothiophene- 4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-I I), 4,6-bis[3-(phenanthren-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyridine 4,6mDBTP2Pm-II, 4,6-bis[3-(9H-carbazo Diazines such as 4,6mCzP2Pm Heterocyclic compounds with a skeleton and 2-{4-[3-(N-phenyl-9H-carbazole- 3-yl)-9H-carbazol-9-yl]phenyl}-4,6-diphenyl-1,3 ,5-triazine (abbreviation: PCCzPTzn), 9-[3-(4,6-diphenyl-1, 3,5-Triazin-2-yl)phenyl]-9'-phenyl-2,3'-bi-9H-ca Heterocyclization of triazine skeleton such as rubazoline (abbreviation: mPCCzPTzn-02) Compounds such as 3,5-bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation Name: 35DCzPPy), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene Heterocyclic compounds having a pyridine skeleton, such as TmPyPB, can also be used. In addition, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl) PF -Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2 PF-BPy) It can also be used.

[0168] 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-dimeth Diphenylchrysene, DBC1, 9-[4-(10-phenyl-9- 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 ( DPPA), 9,10-di(2-naphthyl)anthracene (DNA), 2- tert-Butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA ), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'- Diphenylphenanthrene (DPNS), 9,9'-(stilbene-4,4'-di 1,3,5-tri(1-pyrenyl)benzoate (abbreviation: DPNS2), Zen (abbreviation: TPB3) etc. can be used.

[0169] 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.

[0170] 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.

[0171] 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).

[0172] 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.

[0173] In addition, when using a TADF material, it can also be used in combination with other organic compounds. In particular, it can be combined with the above-mentioned host material, hole transport material, and electron transport material. The organic compound according to the first embodiment of the present invention is used as a host material for a TADF material. It is preferable to use it as

[0174] 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:

[0175] <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. In addition, the organic compound according to one embodiment of the present invention shown in Embodiment 1 can be used. Since it has excellent electron transport properties, it can also be used as an electron transport layer.

[0176] 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.

[0177] 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.

[0178] 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.

[0179] 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.

[0180] 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.

[0181] <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 (LiOx ) 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.

[0182] In addition, the electron injection layer (115, 115a, 115b) contains an organic compound and an electron donor (donor ) may be used. Such composite materials may be formed by mixing 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.

[0183] 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.

[0184] <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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] <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.

[0189] 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.

[0190] 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.

[0191] 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.

[0192] The structure described in this embodiment mode can be used in appropriate combination with structures described in other embodiments. It is possible.

[0193] (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

[0194] 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.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] 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.

[0199] 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.

[0200] 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.

[0201] (Embodiment 4) In this embodiment, a light-emitting device which is one embodiment of the present invention will be described.

[0202] 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.

[0203] In this embodiment mode, an active matrix light emitting device will be described with reference to FIG.

[0204] 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 .

[0205] In addition, a lead wiring 307 is provided on the first substrate 301. 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.

[0206] Next, a cross-sectional structure is shown in FIG.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] 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.

[0211] 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.

[0212] The end of the first electrode 313 is covered with an insulator 314. , organic compounds such as negative photosensitive resins and positive photosensitive resins (acrylic resins), and acids. Inorganic compounds such as silicon oxide, silicon oxynitride, and silicon nitride can be used. It is preferable that the upper end or the lower end of the edge 314 has a curved surface having a curvature. This allows the film formed on the upper layer of the insulator 314 to have good coverage.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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).

[0217] 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.

[0218] In this manner, an active matrix light emitting device can be obtained.

[0219] 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.

[0220] 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.

[0221] (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.

[0222] 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.

[0223] 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.

[0224] 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.

[0225] FIG. 4C shows a goggle-type display. In addition to the above, a second display unit 7002 , a support 7012, an earphone 7013, etc.

[0226] 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.

[0227] 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.

[0228] 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.

[0229] 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.

[0230] 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. .

[0231] 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.

[0232] 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

[0233] 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.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] 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.

[0238] 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

[0239] 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.

[0240] (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.

[0241] 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.

[0242] 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 .

[0243] 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.

[0244] 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.

[0245] 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.

[0246] 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. .

[0247] 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.

[0248] 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.

[0249] 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 .

[0250] 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.

[0251] 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.

[0252] (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.

[0253] 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).

[0254] 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.

[0255] 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.

[0256] 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.

[0257] 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.

[0258] As described above, various lighting devices using the light-emitting device can be obtained. is included in one aspect of the present invention.

[0259] The structure shown in this embodiment mode may be used in appropriate combination with structures shown in other embodiment modes. It is possible. EXAMPLES

[0260] <Synthesis Example 1> In this example, an organic compound represented by structural formula (100) in Embodiment 1, which is one embodiment of the present invention, is used. Compound, 9-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]naphtho[ 1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr) The synthesis method is explained below. The structure of 9mDBtBPNfpr is shown below.

[0261] [ka]

[0262] <Step 1; 6-chloro-3-(2-methoxynaphthalen-1-yl)pyrazine-2- Synthesis of amines> First, 4.37 g of 3-bromo-6-chloropyrazine-2-amine and 2-methoxynaphthalene 4.23g of 1-boronic acid, 4.14g of potassium fluoride, 75g of dehydrated tetrahydrofuran The flask was then placed in a three-neck flask equipped with a reflux condenser and the inside of the flask was replaced with nitrogen. After degassing by stirring at 40°C, tris(dibenzylideneacetone)dipalladium(0) ( abbreviation: Pd2(dba)3) 0.57 g, tri-tert-butylphosphine (abbreviation: P 4.5 mL of (tBu)3) was added, and the mixture was stirred at 80° C. for 54 hours to react.

[0263] After a predetermined time had elapsed, the mixture was filtered under suction, and the filtrate was concentrated. The mixture was purified by silica gel column chromatography using ethyl acetate / ethyl acetate 9:1 as a developing solvent. The desired pyrazine derivative was obtained (yellow-white powder, yield 2.19 g, 36%). Step 1 The synthesis scheme is shown in the following formula (a-1).

[0264] [ka]

[0265] Step 2: 9-chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine Synthesis> Next, 6-chloro-3-(2-methoxynaphthalene-1-yl)piperidinyl obtained in step 1 above was added to the 2.18 g of radin-2-amine, 63 mL of dehydrated tetrahydrofuran, and 84 mL of glacial acetic acid were mixed together in a tritium solution. The flask was cooled to -10°C and then nitrite was added to the flask. 2.8 mL of rt-butyl was added dropwise, and the mixture was stirred at -10°C for 30 minutes and at 0°C for 3 hours. After the time had passed, 250 mL of water was added to the resulting suspension, and the target pyridine was isolated by suction filtration. The compound was obtained as a yellowish white powder (yield: 1.48 g, 77%). The model is shown in (a-2) below.

[0266] [ka]

[0267] <Step 3; 9-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl] Naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNf Synthesis of pr) Furthermore, the 9-chloronaphtho[1',2':4,5]furo[2,3- b] Pyrazine 1.48g, 3'-(4-dibenzothiophene)-1,1'-biphenyl- 3.41 g of 3-boronic acid, 8.8 mL of 2 M potassium carbonate aqueous solution, 100 mL of toluene, 10 mL of ethanol was placed in a three-neck flask, and the inside of the flask was replaced with nitrogen. The inside of the flask was stirred under reduced pressure. After degassing by stirring, bis(triphenylphosphine)palladium(II) dichloride was added. Add 0.84 g of Pd(PPh3)2Cl2, stir at 80°C for 18 hours, and react. He responded.

[0268] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the target product was obtained by recrystallization with a mixed solvent of toluene and hexane. Light yellow solid, yield 2.66 g, 82% yield.

[0269] The resulting pale yellow solid (2.64 g) was purified by train sublimation. The purification conditions were a pressure of 2.6 Pa, argon gas flow rate of 15 mL / min, and 3 The solid was heated at 15°C. After purification by sublimation, the target pale yellow solid was obtained in an amount of 2.34 g and a yield of 89%. The synthesis scheme of step 3 is shown in (a-3) below.

[0270] [ka]

[0271] The pale yellow solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in FIG. In the embodiment, the organic compound represented by the above structural formula (100), 9mDBtBPNfpr It was found that the following was obtained.

[0272] 1 H-NMR.δ(CD2Cl2):7.47-7.51(m,2H),7.60-7. 69(m,5H),7.79-7.89(m,6H),8.05(d,1H),8.10 -8.11(m,2H),8.18-8.23(m,3H),8.53(s,1H),9 .16(d,1H),9.32(s,1H).

[0273] Next, the UV-visible absorption spectrum of 9mDBtBPNfpr in toluene solution (hereafter simply The absorption spectrum and emission spectrum are shown in FIG. The axes represent the absorption and emission intensities.

[0274] The absorption spectrum was measured using an ultraviolet-visible spectrophotometer (JASCO Corporation, V550 model). The absorption spectrum of 9mDBtBPNfpr in toluene solution was The absorption spectrum of the toluene solution of fpr measured in a quartz cell shows that The absorption spectrum was calculated by subtracting the absorption spectrum obtained by measuring the emission spectrum in a quartz cell. The optical spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). The emission spectrum of 9mDBtBPNfpr in toluene solution is The toluene solution was placed in a quartz cell and measured.

[0275] As shown in FIG. 10(A), the toluene solution of 9mDBtBPNfpr had peaks at 370 nm and 380 nm. The absorption peaks are around 400 nm and 421 nm (excitation wavelength: 291 nm). A peak in the emission wavelength was observed around

[0276] Next, the absorption and emission spectra of a solid thin film of 9mDBtBPNfpr were measured. The solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the thin film was , absorbance calculated from transmittance and reflectance including the substrate (-log 10 [%T / (100-% R)). %T represents transmittance and %R represents reflectance. Measurement of absorption spectrum A UV-Vis spectrophotometer (Hitachi High-Technologies Corporation, U-4100) was used for the measurement. The emission spectrum was measured using a fluorometer (FS920, manufactured by Hamamatsu Photonics, Inc.). The absorption and emission spectra of the obtained solid thin film are shown in FIG. The horizontal axis represents the wavelength, and the vertical axis represents the absorption intensity and emission intensity.

[0277] As shown in Fig. 10(B), the solid thin film of 9mDBtBPNfpr has a diameter of 377 nm and 3 An absorption peak is observed around 95 nm, and an emission peak is observed around 489 nm (excitation wavelength: 370 nm). A long peak was observed.

[0278] Thus, the organic compound, 9mDBtBPNfpr, which is one embodiment of the present invention, is capable of producing red and This shows that the host material is suitable for phosphorescent materials that emit light at longer wavelengths. In addition, the organic compound 9mDBtBPNfpr, which is one embodiment of the present invention, emits phosphorescence in the visible range. They can also be used as host materials for optical substances or as luminescent substances.

[0279] Next, the LUMO level of 9mDBtBPNfpr is shown. Reductions obtained by cyclic voltammetry (CV) measurements in dichloromethane solvent. Potential and reference electrode (Ag / Ag + ) potential energy (-4 relative to the vacuum level. The LUMO level was estimated from the value of the LUMO potential (approximately 94 eV). Specifically, the value of -4. 94[eV]-(reduction potential value)=LUMO level. The measured value of the level was -3.05 eV. Therefore, 9mDBtBPNfpr does not receive an electron. It is easy to remove and has high stability against electrons. EXAMPLES

[0280] In this example, the 9-[(3' -Dibenzothiophene-4-yl)biphenyl-3-yl]naphtho[1',2':4,5 ]Furo[2,3-b]pyrazine (abbreviation: 9mDBtBPNfpr) (structural formula (100)) The light-emitting device 1 uses 2-[3'-(dibenzothiophene-4 -yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTB Regarding comparative light-emitting element 2 using PDBq-II) as the light-emitting layer, the element structure, fabrication method, and The characteristics of the light emitting element will be described. The structure of the light emitting element used in this embodiment is shown in FIG. The specific configuration is shown in Table 1. The chemical formulas of the materials used in this example are shown below. .

[0281] [Table 1]

[0282] [ka]

[0283] <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.

[0284] 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.

[0285] Here, as a pretreatment, the surface of the substrate is washed with water, baked at 200°C for 1 hour, and then UV-treated. The treatment was carried out for 370 seconds. -4 Vacuum deposition equipment with the inside pressure reduced to about Pa The substrate was placed in the vacuum deposition apparatus and vacuum baked at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus. After that, the substrate was allowed to cool for about 30 minutes.

[0286] 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 reducing the pressure to 100 Pa, 1,3,5-tri(dibenzothiophene-4-isotope DBT3P-II: benzene (abbreviation: DBT3P-II) and molybdenum oxide The molybdenum oxide was mixed with molybdenum chloride at a mass ratio of 2:1 and the film thickness was 75 nm. .

[0287] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 was made of 4-fluorophenyl ether. 4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BP The film was formed by deposition using AFLP to a thickness of 20 nm.

[0288] Next, a light-emitting layer 913 was formed on the hole-transporting layer 912 .

[0289] In the case of the light-emitting element 1, the light-emitting layer 913 is made of 9mDBtBPNfpr and N-(1,1'- Biphenyl-4-yl)-N-[4-(9-phenyl-9H-carbazol-3-yl) Phenyl]-9,9-dimethyl-9H-fluoren-2-amine (abbreviation: PCBBiF) In addition, bis{4,6-dimethyl-2-[3-( 3,5-Dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC} (2,6-Dimethyl-3,5-heptanedionate-κ 2 O,O') Iridium(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]) with a weight ratio of 9mDBtB PNfpr:PCBBiF:[Ir(dmdppr-P)2(dibm)]=0.75: The film thickness was 40 nm. In the case of light-emitting element 2, in addition to 2mDBTBPDBq-II and PCBBiF, The material (phosphorescent material) used was [Ir(dmdppr-P)2(dibm)], and the The ratio of the amount of PCBBiF to the amount of Ir(dmdppr-P)2(d The film thickness was 40 mm. nm.

[0290] Next, an electron transport layer 914 was formed on the light-emitting layer 913. In the case of (yl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen) film The layers were deposited in order to have a thickness of 15 nm. The thickness of DBTBPDBq-II was 30 nm, and the thickness of NBphen was 15 nm. The layers were formed by sequential deposition.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] Moreover, the light emitting element manufactured as described above is sealed with another substrate (not shown). When sealing using another substrate (not shown), the sealing is performed in a glove box with a nitrogen atmosphere. Then, another substrate (not shown) coated with a sealant that is hardened by ultraviolet light is placed on the substrate 900. The substrates are fixed together so that the sealant adheres to the periphery of the light emitting element formed on the substrate 900. During sealing, 365 nm ultraviolet light was applied at 6 J / cm. 2 Irradiate the sealant to harden it, and then The sealant was stabilized by heat treatment at 0° C. for 1 hour.

[0295] <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 current density-luminance characteristics of each light-emitting device are shown in Figure 1. 2. Voltage-luminance characteristics are shown in Fig. 13, luminance-current efficiency characteristics in Fig. 14, and voltage-current characteristics in Fig. 15. Each is shown.

[0296] Also, 1000cd / m 2 The main initial characteristics of each light-emitting element in the vicinity are shown in Table 2 below. .

[0297] [Table 2]

[0298] The above results show that the light-emitting element 1 fabricated in this example exhibits good efficiency.

[0299] Furthermore, the light-emitting element 1 and the comparative light-emitting element 2 were subjected to an electric current of 2.5 mA / cm 2 A current was passed with a current density of The emission spectra at that time are shown in FIG. 16. As shown in FIG. 16, the light-emitting element 1 and the comparative light-emitting element The emission spectrum of the light emitting layer 913 has a peak at about 640 nm. It has been found that this is due to the emission of [Ir(dmdppr-P)2(dibm)] contained in It is suggested.

[0300] Next, a reliability test was performed on the light-emitting element 1 and the comparative light-emitting element 2. Results of the reliability test This is shown in FIG. 17. In FIG. 17, 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 50 mA / cm 2 A constant current drive test was conducted in which a constant current was applied at a current density of 1000 s.

[0301] The results of the reliability test showed that the light-emitting element 1 exhibited higher reliability than the comparative light-emitting element 2. This is the molecular structure of 9mDBtBPNfpr and 2mDBTBPDBq-II. The above difference is due to the difference between the naphthofuropyrazine skeleton and the dibenzoquinoxaline skeleton. This is believed to demonstrate the robustness of the furopyrazine derivative according to one embodiment of the present invention. From the above, it can be said that the organic compound 9mDBtBPNfpr( It is said that the use of structural formula (100) is useful for improving the characteristics of light-emitting devices. can. EXAMPLES

[0302] In this embodiment, the 9mDBtB light-emitting element described in Example 1 is used as a light-emitting element according to one embodiment of the present invention. We fabricated a light-emitting device 3 using PNfpr (structural formula (100)) in the light-emitting layer, and investigated its characteristics. The results of the measurements are shown below.

[0303] In the fabrication of the light-emitting element 3, the first electrode 901 and the hole injection layer 911 were formed as in Example 1. The light-emitting element was formed in the same manner as in the light-emitting element 1 shown in FIG.

[0304] The hole transport layer 912 formed on the hole injection layer 911 is made of 4,4'-diphenyl-4 ''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: P The film was formed by vapor deposition using CBBi1BP) to a thickness of 20 nm.

[0305] The light-emitting layer 913 formed on the hole-transporting layer 912 is made of 9mDBtBPNfpr and PCBBiF was used as the guest material (phosphorescent material), and bis[4,6-dimethyl-2 -(2-quinolinyl-κN)phenyl-κC](2,4-pentanedionato-κ 2 O,O ') Iridium (III) (abbreviation: [Ir(dmpqn)2(acac)] by weight The ratio is 9mDBtBPNfpr:PCBBiF:[Ir(dmpqn)2(acac)]= The film was formed by co-evaporation in a ratio of 0.8:0.2:0.1. The thickness was set to 0 nm.

[0306] The electron transport layer 914 formed on the light emitting layer 913 has a thickness of 9mDBtBPNfpr. The film was deposited in this order so that the thickness of the NBphen was 15 nm.

[0307] The structures from the electron injection layer 915 to the second electrode 903 are the same as those of the light-emitting element 1 shown in Example 2. The specific element configuration of the light-emitting element 3 is shown in Table 3. The chemical formula of the material used is shown below:

[0308] [Table 3]

[0309] [ka]

[0310] <Operation characteristics of light-emitting element 3> The operating characteristics of the fabricated light-emitting element 3 were measured. The measurements were performed at room temperature (25° C.) I went there for the atmosphere.

[0311] FIG. 18 shows the current density-luminance characteristics of the light-emitting element 3, FIG. 19 shows the voltage-luminance characteristics, and FIG. 11 shows the luminance-current efficiency characteristics. The characteristics are shown in Figure 20 and the voltage-current characteristics are shown in Figure 21.

[0312] Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 3 in the vicinity are shown in Table 4 below. .

[0313] [Table 4]

[0314] The above results show that the light-emitting element 3 fabricated in this example exhibits good efficiency.

[0315] In addition, the light-emitting element 3 is supplied with 2.5 mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 22, the emission spectrum of the light-emitting element has a peak at about 626 nm. The light-emitting layer 913 has a peak of [Ir(dmpqn)2(acac)]. This suggests that it is due to luminescence.

[0316] Next, a reliability test was performed on the light-emitting element 3. The results of the reliability test are shown in FIG. In Figure 3, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is performed at 75mA / cm 2 At a constant current density A constant current drive test was carried out.

[0317] The results of the reliability test showed that the light-emitting element 3 exhibited high reliability. Using the organic compound 9mDBtBPNfpr (structural formula (100)) which is one embodiment of the present invention, It can be said that this is useful for improving the element characteristics of the light-emitting element. EXAMPLES

[0318] In this embodiment, the 9mDBtB light-emitting element described in Example 1 is used as a light-emitting element according to one embodiment of the present invention. We fabricated light-emitting device 4 using PNfpr (structural formula (100)) in the light-emitting layer, and investigated its characteristics. The results of the measurements are shown below.

[0319] In the fabrication of the light-emitting element 4, the first electrode 901 and the hole injection layer 911 were formed as in Example 1. The light-emitting element was formed in the same manner as in the light-emitting element 1 shown in FIG.

[0320] The hole transport layer 912 formed on the hole injection layer 911 is made of PCBBiF and has a thickness of The film was formed by evaporation so that the thickness was 20 nm.

[0321] The light-emitting layer 913 formed on the hole-transporting layer 912 is made of 9mDBtBPNfpr and PCBBiF was used as the guest material (phosphorescent material), and bis{4,6-dimethyl-2 -[5-(5-cyano-2-methylphenyl)-3-(3,5-dimethylphenyl)-2 -pyrazinyl-κN]phenyl-κC}(2,2,6,6-tetramethyl-3,5-heptyl Tandione-κ 2 O,O')iridium(III) (abbreviation: [Ir(dmdppr-m 5CP)2(dpm)] was used, with a weight ratio of 9mDBtBPNfpr:PCBBiF:[I r(dmdppr-m5CP)2(dpm)] = 0.8:0.2:0.1 The film was formed by vapor deposition to a thickness of 40 nm.

[0322] The electron transport layer 914 formed on the light emitting layer 913 has a thickness of 9mDBtBPNfpr. The film was deposited in this order so that the thickness of the NBphen was 15 nm.

[0323] The structures from the electron injection layer 915 to the second electrode 903 are the same as those of the light-emitting element 1 shown in Example 2. The specific element configuration of the light-emitting element 4 is shown in Table 5. The chemical formula of the material used is shown below:

[0324] [Table 5]

[0325] [ka]

[0326] <Operation characteristics of light-emitting element 4> The operating characteristics of the fabricated light-emitting element 4 were measured. The measurements were performed at room temperature (25° C.) I went there for the atmosphere.

[0327] FIG. 24 shows the current density-luminance characteristics of the light-emitting element 4, FIG. 25 shows the voltage-luminance characteristics, and FIG. 26 shows the luminance-current efficiency characteristics. The characteristics are shown in Figure 26 and the voltage-current characteristics are shown in Figure 27.

[0328] Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 4 in the vicinity are shown in Table 6 below. .

[0329] [Table 6]

[0330] The above results show that the light-emitting element 4 fabricated in this example exhibits good efficiency.

[0331] In addition, the light-emitting element 4 is supplied with 2.5 mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 28, the emission spectrum of the light-emitting element has a peak at about 648 nm. The light-emitting layer 913 has a peak, and [Ir(dmdppr-m5CP)2(d This suggests that the emission from the ion beam is due to the emission of 10 ...

[0332] Next, a reliability test was performed on the light-emitting element 4. The results of the reliability test are shown in FIG. In Figure 9, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is performed at 75mA / cm 2 At a constant current density A constant current drive test was carried out.

[0333] The results of the reliability test showed that the light-emitting element 4 had high reliability. Using the organic compound 9mDBtBPNfpr (structural formula (100)) which is one embodiment of the present invention, It can be said that this is useful for improving the element characteristics of the light-emitting element. EXAMPLES

[0334] In this embodiment, the 9mDBtB light-emitting element described in Example 1 is used as a light-emitting element according to one embodiment of the present invention. A light-emitting device 5 was fabricated using PNfpr (structural formula (100)) in the light-emitting layer, and its characteristics were examined. The results of the measurements are shown below.

[0335] The specific element configuration of the light-emitting element 5 is shown in Table 7. In the table, APC is an alloy of silver, palladium, and copper. For the stacking of the light-emitting element, see FIG. 11. However, in the light-emitting element 5, the cap formed in contact with the second electrode 903 is The layers are all included in the light emitting element. The chemical formulas of the materials used in this embodiment are shown below.

[0336] [Table 7]

[0337] [ka]

[0338] <Operation characteristics of light-emitting element 5> The operating characteristics of the fabricated light-emitting element 5 were measured. The measurements were performed at room temperature (25° C.) I went there for the atmosphere.

[0339] FIG. 30 shows the current density-luminance characteristics of the light-emitting element 5, FIG. 31 shows the voltage-luminance characteristics, and FIG. 32 shows the luminance-current efficiency characteristics. The characteristics are shown in Figure 32 and the voltage-current characteristics are shown in Figure 33.

[0340] Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 5 in the vicinity are shown in Table 8 below. .

[0341] [Table 8]

[0342] The above results show that the light-emitting element 5 fabricated in this example exhibits good efficiency.

[0343] In addition, the light emitting element 5 is supplied with 2.5 mA / cm 2 The emission spectrum when a current is applied at a current density of As shown in FIG. 34, the emission spectrum of the light-emitting element has a peak at about 635 nm. The light-emitting layer 913 has a peak, and [Ir(dmdppr-m5CP)2(d pm)]. The compound, 9mDBtBPNfpr, emits in the red and longer wavelength energies. This shows that the compound is a suitable host material for phosphorescent materials.

[0344] Next, a reliability test was performed on the light-emitting element 5. The results of the reliability test are shown in FIG. In Figure 5, 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 12.5mA / cm 2 Constant current density A constant current drive test was conducted in which a current of

[0345] The results of the reliability test showed that the light-emitting element 5 exhibited high reliability. Using the organic compound 9mDBtBPNfpr (structural formula (100)) which is one embodiment of the present invention, It can be said that this is useful for improving the element characteristics of the light-emitting element.

[0346] Here, other light-emitting devices (light-emitting devices) having the device structure shown in Table 9 and the operating characteristics shown in Table 10 are A top emission structure formed by combining the light emitting element 5 with the light emitting element 6 and the light emitting element 7). The panel is assumed to have an aperture ratio of 15% (R, G, B pixels are 5% each), a circular polarizer, etc. With 60% luminous attenuation due to the luminance change, D65, 300cd / m 2 Simulation of all white display We conducted a ration.

[0347] [Table 9]

[0348] The chemical formulas of some of the materials used in each light-emitting element in Table 9 are shown below.

[0349] [ka]

[0350] [Table 10]

[0351] Table 11 shows the data used in the simulation from among the measurement results of the above light-emitting elements.

[0352] [Table 11]

[0353] According to a simulation using the data in Table 11, the chromaticity (x, y) of each light-emitting element is calculated as When calculated using E1976 chromaticity coordinates (u', v' chromaticity coordinates), the light-emitting element 5 (R), In a panel formed by combining a light-emitting element 6 (G) and a light-emitting element 7 (B), BT.202 The result was that the area ratio to the color gamut of the 1.0 standard was 97%. EXAMPLES

[0354] <Synthesis Example 2> In this example, an organic compound represented by structural formula (123) in Embodiment 1, which is one embodiment of the present invention, Compound, 9-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)naphtho[ Synthesis of 1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9PCCzNfpr) The method is explained below. The structure of 9PCCzNfpr is shown below.

[0355] [ka]

[0356] The synthesis method of 9-chloronaphtho[1',2':4,5 ]Furo[2,3-b]pyrazine 0.94g, 9'-phenyl-3,3'-bi-9H-carbamate 1.69 g of Bazole and 37 mL of mesitylene were placed in a three-neck flask, and the inside was replaced with nitrogen. After degassing the flask by stirring under reduced pressure, sodium tert-butoxide was added .23g, tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(db a) 3) 0.021g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl Add 0.030 g of phenyl (abbreviation: S-Phos) and stir at 120°C for 8 hours to react. Ta.

[0357] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the target product was obtained by recrystallization with a mixed solvent of toluene and hexane. Yellow solid, 0.85 g, 36% yield.

[0358] The resulting yellow solid (0.84 g) was purified by train sublimation. The purification conditions were: pressure 2.5 Pa, argon gas flow rate 10 mL / min, 35 The solid was heated at 0°C. After purification by sublimation, the target yellow solid was obtained in an amount of 0.64 g and a yield of 76%. The synthesis scheme of the above synthesis method is shown in (b-1) below.

[0359] [ka]

[0360] The yellow solid obtained by the above synthesis was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR analysis results The results are shown below. 1 The H-NMR chart is shown in FIG. The organic compound 9PCCzNfpr represented by the above structural formula (123) was obtained. I realized that.

[0361] 1 H-NMR.δ(CDCl3):7.32-7.35(m,1H),7.42-7.5 7(m,6H),7.63-7.70(m,5H),7.80-7.90(m,4H), 8.09(d,2H),8.14(d,2H),8.27(d,2H),8.49(d, 2H), 9.20(d,1H), 9.27(s,1H). EXAMPLES

[0362] <Synthesis Example 3> In this example, an organic compound represented by structural formula (125) in Embodiment 1, which is one embodiment of the present invention, Compound 9-[3-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)phenyl] phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mPCC The synthesis method of 9mPCCzPNfpr is explained below. Shown below.

[0363] [ka]

[0364] <Step 1; 9-(3-chlorophenyl)naphtho[1',2':4,5]furo[2,3 -b]Synthesis of pyrazine> The synthesis method of 9-chloronaphtho[1',2':4,5 ]furo[2,3-b]pyrazine 2.12 g, 3-chlorophenylboronic acid 1.41 g, 2 14 mL of potassium carbonate solution, 83 mL of toluene, and 8.3 mL of ethanol were added to a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure, and then acetic acid was added. Palladium(II) (abbreviation: Pd(OAc)2) 0.19g, tris(2,6-dimethoxy Add 1.12 g of P(2,6-diphenyl)phosphine (abbreviation: P(2,6-MeOPh)3) and mix for 90 The mixture was stirred at ℃ for 7.5 hours to react.

[0365] After a predetermined time had elapsed, the mixture was filtered by suction and washed with ethanol. The desired pyrazine was isolated by silica gel column chromatography using benzene as a developing solvent. The derivative was obtained (yellowish white powder, yield 1.97 g, 73%). Synthesis scheme of step 1 is shown in the following formula (c-1).

[0366] [ka]

[0367] <Step 2; Synthesis of 9mPCCzPNfpr> Next, the 9-(3-chlorophenyl)naphtho[1',2':4,5 ]furo[2,3-b]pyrazine 1.45g, 9'-phenyl-3,3'-bi-9H-carbamate 1.82 g of Bazole and 22 mL of mesitylene were placed in a three-neck flask, and the inside was replaced with nitrogen. After degassing the flask by stirring under reduced pressure, sodium tert-butoxide 0 .85g, tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(db a) 3) 0.025g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl The mixture was stirred at 150°C for 7 hours to react. Ta.

[0368] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the target product was obtained by recrystallization with a mixed solvent of toluene and hexane. Yellow solid, yield 2.22 g, 71% yield.

[0369] The resulting yellow solid (2.16 g) was purified by train sublimation. The purification conditions were: pressure 2.6 Pa, argon gas flow rate 18 mL / min, 38 The solid was heated at 5°C. After purification by sublimation, the target yellow solid was obtained in an amount of 1.67 g and a yield of 77%. The synthesis scheme of step 2 is shown in the following formula (c-2).

[0370] [ka]

[0371] The yellow 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 FIG. In the embodiment, the organic compound represented by the above structural formula (125), 9mPCCzPNfpr It was found that the following was obtained.

[0372] 1 H-NMR.δ(CD2Cl2):7.31-7.39(m,2H),7.43-7. 59(m,6H),7.64-7.69(m,6H),7.78-7.88(m,6H) ,8.09(d,1H),8.15(d,1H),8.26(d,1H),8.30(d ,1H),8.34(d,1H),8.51-8.55(m,3H),9.15(d,1 H), 9.35(s,1H). EXAMPLES

[0373] <Synthesis Example 4> In this example, an organic compound represented by structural formula (126) in Embodiment 1, which is one embodiment of the present invention, Compound 9-[3-(9'-phenyl-2,3'-bi-9H-carbazol-9-yl)phenyl] phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mPCC The synthesis method of 9mPCCzPNfpr-02) is explained below. The structure of 2 is shown below.

[0374] [ka]

[0375] The synthesis method of 9-chloronaphtho[1',2':4,5 ]furo[2,3-b]pyrazine 1.19 g, 3-(9'-phenyl-2,3'-bi-9H -Carbazol-9-yl)phenylboronic acid pinacol ester 3.51g, 2M carbonate Put 6.0 mL of potassium solution, 60 mL of toluene, and 6 mL of ethanol into a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure, and then bis(trifluoroacetate) was added. (phenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2) 0.33 g was added, and the mixture was stirred at 90° C. for 16 hours to cause a reaction.

[0376] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the target product was obtained by recrystallization with a mixed solvent of toluene and hexane. Yellow solid, 3.01 g, 90% yield.

[0377] The resulting yellow solid (3.00 g) was purified by train sublimation. The purification conditions were: pressure 2.7 Pa, argon gas flow rate 16 mL / min, 38 The solid was heated at 0°C. After purification by sublimation, the target yellow solid was obtained in an amount of 2.47 g and a yield of 82%. The synthesis scheme is shown in the following formula (d-1).

[0378] [ka]

[0379] The yellow solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of the analysis using H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in FIG. As a result, the organic compound 9mPCCzPNfpr-02 represented by the above structural formula (126) was obtained. It was found that

[0380] 1 H-NMR.δ(CD2Cl2):7.22-7.25(m,1H),7.34-7. 42(m,3H),7.46-7.49(m,3H),7.55-7.66(m,6H) ,7.72-7.88(m,7H),8.07(d,1H),8.13(d,1H),8 .19-8.22(m,2H),8.28(d,1H),8.33(d,1H),8.4 6(s,1H),8.54(s,1H),9.14(d,1H),9.34(s,1H) . EXAMPLES

[0381] <Synthesis Example 5> In this example, an organic compound represented by structural formula (133) in Embodiment 1, which is one embodiment of the present invention, Compound, 10-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]naphtho [1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 10mDBtBPNfpr The synthesis method of 10mDBtBPNfpr is shown below.

[0382] [ka]

[0383] <Step 1; 5-chloro-3-(2-methoxynaphthalen-1-yl)pyrazine-2- Synthesis of amines> First, 5.01 g of 3-bromo-5-chloropyrazine-2-amine and 2-methoxynaphthalene 6.04 g of 1-boronic acid, 5.32 g of potassium fluoride, 86 g of dehydrated tetrahydrofuran The flask was then placed in a three-neck flask equipped with a reflux condenser and the inside of the flask was replaced with nitrogen. After degassing by stirring at 40°C, tris(dibenzylideneacetone)dipalladium(0) ( abbreviation: Pd2(dba)3) 0.44 g, tri-tert-butylphosphine (abbreviation: P 3.4 mL of (tBu)3 was added, and the mixture was stirred at 80° C. for 22 hours to react.

[0384] After a predetermined time had elapsed, the mixture was filtered under suction, and the filtrate was concentrated. The mixture was purified by silica gel column chromatography using ethyl acetate / ethyl acetate 10:1 as a developing solvent. The desired pyrazine derivative was obtained (yellow-white powder, yield 5.69 g, 83%). The synthesis scheme of 1 is shown in the following formula (e-1).

[0385] [ka]

[0386] <Step 2: 10-Chloronaphtho[1',2':4,5]furo[2,3-b]pyrazine Synthesis of > Next, 5-chloro-3-(2-methoxynaphthalene-1-yl) 5.69 g of pyrazin-2-amine, 150 mL of dehydrated tetrahydrofuran, 150 mL of glacial acetic acid L was placed in a three-neck flask and the inside was replaced with nitrogen. The flask was cooled to -10°C, and then nitrous acid was added. 7.1 mL of tert-butyl acetate was added dropwise, and the mixture was stirred at -10°C for 1 hour and at 0°C for 3.5 hours. After a certain time has elapsed, 1 L of water is added to the resulting suspension, and the suspension is filtered by suction to isolate the desired pyramids. The azine derivative was obtained (yellowish white powder, yield 4.06 g, 81%). The formula is shown in formula (e-2) below.

[0387] [ka]

[0388] <Step 3; Synthesis of 10mDBtBPNfpr> Furthermore, the 10-chloronaphtho[1',2':4,5]furo[2, 3-b]pyrazine 1.18g, 3'-(4-dibenzothiophene)-1,1'-biphenyl 2.75 g of 3-boronic acid, 7.5 mL of 2M potassium carbonate aqueous solution, 60 mL of toluene, 6 mL of ethanol was placed in a three-neck flask, and the inside of the flask was replaced with nitrogen. The contents of the flask were stirred under reduced pressure. After degassing by stirring, bis(triphenylphosphine)palladium(II) dichloride was added. Add 0.66 g of Pd(PPh3)2Cl2 and stir at 90℃ for 22.5 hours. The reaction was carried out.

[0389] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the product was recrystallized in a mixed solvent of toluene and hexane to obtain the target product. (White solid, yield 2.27 g, 87%)

[0390] The resulting white solid (2.24 g) was purified by train sublimation. The purification conditions were a pressure of 2.3 Pa, argon gas flow rate of 16 mL / min, and 31 The solid was heated at 0°C. After purification by sublimation, the target white solid was obtained in an amount of 1.69 g and a yield of 75%. The synthetic scheme of step 3 is shown in the following formula (e-3).

[0391] [ka]

[0392] The white solid obtained in step 3 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in FIG. In the embodiment, the organic compound represented by the above structural formula (133), 10mDBtBPNfp It was found that r was obtained.

[0393] 1 H-NMR.δ(CDCl3):7.43(t,1H),7.48(t,1H),7. 59-7.62(m,3H),7.68-7.86(m,8H),8.05(d,1H) ,8.12(d,1H),8.18(s,1H),8.20-8.24(m,3H),8 .55(s,1H),8.92(s,1H),9.31(d,1H). EXAMPLES

[0394] <Synthesis Example 6> In this example, an organic compound represented by structural formula (156) in Embodiment 1, which is one embodiment of the present invention, Compound, 10-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)naphtho [1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 10PCCzNfpr) The synthesis method is explained below. The structure of 10PCCzNfpr is shown below.

[0395] [ka]

[0396] The synthesis method of 10-chloronaphtho[1',2':4, 5] Furo[2,3-b]pyrazine 1.80g, 9'-phenyl-3,3'-bi-9H-ca 3.10 g of rubazolyl and 71 mL of mesitylene were placed in a three-neck flask, and the inside of the flask was replaced with nitrogen. After degassing the flask by stirring under reduced pressure, sodium tert-butoxide was added. 2.21 g, tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(d ba) 3) 0.041g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.061 g of phenyl (abbreviation: S-Phos) was added, and the mixture was stirred at 120°C for 2 hours to react. I did.

[0397] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the target product was obtained by recrystallization with a mixed solvent of toluene and hexane. Orange solid, 3.47 g, 78% yield.

[0398] The resulting orange solid (3.42 g) was purified by train sublimation. The purification conditions were a pressure of 2.4 Pa, argon gas flow rate of 16 mL / min, and 35 The solid was heated at 0°C. After purification by sublimation, the desired orange solid was obtained in an amount of 2.86 g and a yield of 84%. The synthetic scheme of step 3 is shown below in (f-1).

[0399] [ka]

[0400] The orange solid obtained by the above synthesis method was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below. 1 The H-NMR chart is shown in FIG. In the embodiment, the organic compound represented by the above structural formula (156), 10PCCzNfpr, It was found that it was obtained.

[0401] 1 H-NMR.δ(CDCl3):7.32-7.35(m,1H),7.43-7.5 7(m,6H),7.63-7.68(m,5H),7.79-7.84(m,2H), 7.89-7.91(m,2H),8.01(d,1H),8.07-8.09(m,2 H),8.18(d,1H),8.27(d,1H),8.30(d,1H),8.51 (s,2H),8.85(s,1H),9.16(d,1H). EXAMPLES

[0402] <Synthesis Example 7> In this example, an organic compound represented by structural formula (208) in Embodiment 1, which is one embodiment of the present invention, Compound, 12-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]phenanthracene 12mDBtBP The synthesis method of 12mDBtBPPnfpr is explained below. As shown below.

[0403] [ka]

[0404] <Step 1: Synthesis of 9-methoxyphenanthrene> First, 4.02 g of 9-bromo-phenanthrene, 7.80 g of cesium carbonate, and 16 g of toluene were 16 mL of methanol was placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. After degassing the flask by stirring under reduced pressure, palladium acetate (II) (abbreviation: P d(OAc)2) 0.11g, 2-di-tert-butylphosphino-2',4',6' -Triisopropylbiphenyl (abbreviation: tBuXPhos) 0.41g was added and the mixture was heated at 80°C. The reaction was allowed to stir for 17 hours.

[0405] After a certain time had elapsed, the mixture was filtered under suction, and the filtrate was concentrated. The product was purified by silica gel column chromatography using hexane = 1:3 as a developing solvent. The target product was obtained (white powder, yield 2.41 g, 74%). The synthesis scheme for step 1 is shown below. This is shown in formula (g-1).

[0406] [ka]

[0407] <Step 2: Synthesis of 9-bromo-10-methoxyphenanthrene> Next, 2.75 g of 9-methoxyphenanthrene obtained in step 1 above and diisopropyl 0.18 mL of amine, 150 mL of dehydrated dichloromethane, and N-bromosuccinimide (abbreviated 2.52 g of NBS was placed in an Erlenmeyer flask and stirred at room temperature for 18 hours. The extract was washed with water and an aqueous solution of sodium thiosulfate, and then concentrated. The target compound was purified by silica gel column chromatography using a developing solvent of 5:1. The synthesis scheme of step 2 is shown below. Shown in (g-2).

[0408] [ka]

[0409] <Step 3: Synthesis of 10-methoxyphenanthrene-9-boronic acid> Next, 8.49 g of 9-bromo-10-methoxyphenanthrene obtained in step 2 above 250 mL of dehydrated THF was placed in a three-neck flask, and the inside of the flask was replaced with nitrogen. The flask was then cooled to -78°C. After cooling to -78°C, 22 mL of n-butyllithium (1.6 M hexane solution) was added and the mixture was cooled to -78°C. The mixture was stirred at 4°C for 3 hours. Then, 5.7 mL of tetramethylethylenediamine and 5.7 mL of trimethylborate were added. The mixture was stirred at room temperature for 18 hours to allow the reaction to proceed.

[0410] After the specified time had elapsed, 50 mL of 1M hydrochloric acid was added and the mixture was stirred at room temperature for 1 hour. The target product was obtained by extraction (light orange powder, yield 2.87 g, 39%). The synthetic scheme of Step 3 is shown in formula (g-3) below.

[0411] [ka]

[0412] <Step 4: 5-chloro-3-(10-methoxyphenanthren-9-yl)pyrazine -2-Amine synthesis> Next, 3.69 g of 10-methoxyphenanthrene-9-boronic acid obtained in step 3 above was added. 3.02 g of 3-bromo-5-chloropyrazine-2-amine, 70 mL of toluene, 2 M charcoal 35 mL of sodium chloride aqueous solution was placed in a three-neck flask equipped with a reflux condenser, and the inside of the flask was replaced with nitrogen. The flask was degassed by stirring under reduced pressure, and then tetrakis(triphenylphosphine) Add 0.16 g of palladium(0) (abbreviation: Pd(PPh3)4) and heat at 110°C for 7 The mixture was stirred for 30 minutes and allowed to react.

[0413] After a certain time had passed, extraction was performed with toluene. Then, dichloromethane:ethyl acetate= Purification was performed by flash column chromatography using a developing solvent of 50:1 to obtain the desired peaks. The radish derivative was obtained (yellowish white powder, 3.00 g, 62% yield). The scheme is shown in formula (g-4) below.

[0414] [ka]

[0415] <Step 5; 12-Chlorophenanthro[9',10':4,5]furo[2,3-b] Synthesis of pyrazine> Next, 5-chloro-3-(10-methoxyphenanthrene-9- 2.92 g of pyrazin-2-amine, 60 mL of dehydrated tetrahydrofuran, 60 mL of glacial acetic acid The flask was cooled to -10°C and nitrogen was substituted. 3.1 mL of tert-butyl nitrate was added dropwise, and the mixture was stirred at -10°C for 1 hour and at 0°C for 22 hours. .

[0416] After the specified time has elapsed, 200 mL of water is added to the resulting suspension, and the suspension is subjected to suction filtration to obtain the desired product. The pyrazine derivative was obtained (yellowish white powder, yield 2.06 g, 80%). The synthesis scheme is shown below (g-5).

[0417] [ka]

[0418] Step 6: 12-(3-chlorophenyl)phenanthro[9',10':4,5]f Synthesis of B[2,3-b]pyrazine> Next, the 12-chlorophenanthro[9',10':4,5]fluorouracil obtained in step 5 above was [2,3-b]pyrazine 1.02g, 3-chlorophenylboronic acid 0.56g, 2M carbonate Put 5 mL of potassium solution, 33 mL of toluene, and 3.3 mL of ethanol into a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure, and then palladium acetate was added. 0.074 g of palladium(II) (abbreviation: Pd(OAc)2), tris(2,6-dimethoxyphenyl) Add 0.44 g of P(2,6-MeOPh)phosphine (abbreviation: P(2,6-MeOPh)3) and heat at 90°C for 5 The mixture was stirred for 30 minutes and allowed to react.

[0419] After a predetermined time had elapsed, the mixture was filtered under suction, and the filtrate was concentrated. The desired pyrazine derivative is obtained by purifying the product using silica gel column chromatography with the open solvent. (White powder, yield 0.87 g, 70%). The synthesis scheme of step 6 is shown below. Shown in (g-6).

[0420] [ka]

[0421] <Step 7; Synthesis of 12mDBtBPPnfpr> Next, 12-(3-chlorophenyl)phenanthro[9',10 ':4,5]furo[2,3-b]pyrazine 0.85g, 3-(4-dibenzothiophene) Phenylboronic acid 0.73g, potassium phosphate tripotassium 1.41g, tert-butyl alcohol 0.49g of diethylene glycol dimethyl ether (abbreviation: diglyme) 18m The contents of the flask were stirred under reduced pressure to remove the After evaporation, 9.8 mg of palladium(II) acetate (abbreviation: Pd(OAc)2) and 1-(2-phenylpropanediol) were added. Damantyl)-n-butylphosphine (abbreviation: CataCXium A) 32 mg was added. The mixture was stirred at 140° C. for 11.5 hours to react.

[0422] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The body was dissolved in toluene and passed through a filter aid consisting of layers of Celite, alumina, and Celite. After filtering, the product was recrystallized from toluene to obtain the target product (white solid, yield 0.7%). 4g, 55% yield.

[0423] The resulting white solid (0.73 g) was purified by train sublimation. The purification conditions were a pressure of 2.6 Pa, argon gas flow rate of 11 mL / min, and 33 The solid was heated at 0°C. After purification by sublimation, the target white solid was obtained in an amount of 0.49 g and a yield of 67%. The synthetic scheme of step 7 is shown in formula (g-7) below.

[0424] [ka]

[0425] The white solid obtained in step 7 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The analysis results are shown below.1 The H-NMR chart is shown in FIG. In the embodiment, the organic compound represented by the above structural formula (208), 12mDBtBPPnf It was found that pr was obtained.

[0426] 1 H-NMR.δ(CD2Cl2):7.45(t,1H),7.50(t,1H),7 .62-7.66(m,2H),7.70-7.89(m,10H),8.21-8.2 8(m,4H),8.58-8.61(m,2H),8.80(d,1H),8.84( d,1H),8.94(s,1H),9.37(d,1H). EXAMPLES

[0427] <Synthesis Example 8> In this example, an organic compound represented by structural formula (238) in Embodiment 1, which is one embodiment of the present invention, Compound 9-[4-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl)phenyl] phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9pPCC The synthesis method of 9pPCCzPNfpr is explained below. Shown below.

[0428] [ka]

[0429] <Step 1; 9-(4-chlorophenyl)naphtho[1',2':4,5]furo[2,3 -b]Synthesis of pyrazine> The synthesis method of 9-chloronaphtho[1',2':4,5 ]furo[2,3-b]pyrazine 4.10 g, 4-chlorophenylboronic acid 2.80 g, 2 27 mL of potassium carbonate solution, 160 mL of toluene, and 16 mL of ethanol were placed in a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure, and then acetic acid was added. Palladium(II) (abbreviation: Pd(OAc)2) 0.36g, tris(2,6-dimethoxy Add 2.08 g of P(2,6-MeOPh)phosphine (abbreviation: P(2,6-MeOPh)3) and mix for 90 The mixture was reacted at 0.degree. C. for 7 hours with stirring.

[0430] After a predetermined time had elapsed, the mixture was filtered by suction and washed with ethanol. The desired pyrazine was isolated by silica gel column chromatography using benzene as a developing solvent. The derivative was obtained (yellowish white powder, yield 2.81 g, 52%). Synthesis scheme of step 1 is shown in the following formula (h-1).

[0431] [ka]

[0432] <Step 2; Synthesis of 9pPCCzPNfpr> Next, the 9-(4-chlorophenyl)naphtho[1',2':4,5 ]furo[2,3-b]pyrazine 1.39 g, 9'-phenyl-3,3'-bi-9H-carbamate 1.72 g of Bazole and 21 mL of mesitylene were placed in a three-neck flask, and the inside was replaced with nitrogen. After degassing the flask by stirring under reduced pressure, sodium tert-butoxide 0 .81g, tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(db a) 3) 0.024g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl Add 0.034 g of phenyl (abbreviation: S-Phos) and stir at 150°C for 6 hours to react. Ta.

[0433] After a certain time had elapsed, the reaction solution was extracted with toluene. The extract was concentrated to obtain a solid. After purification by silica gel column chromatography using toluene as the developing solvent, The target product was obtained by recrystallization three times in hexane (yellow solid, yield 1.84 g, 62% yield). %).

[0434] The resulting yellow solid (1.81 g) was purified by train sublimation. The purification conditions were: pressure 2.7 Pa, argon gas flow rate 18 mL / min, 38 The solid was heated at 0°C. After purification by sublimation, the target yellow solid was obtained in an amount of 1.35 g and a yield of 75%. The synthesis scheme of step 2 is shown in the following formula (h-2).

[0435] [ka]

[0436] The yellow 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 FIG. In the embodiment, the organic compound represented by the above structural formula (238), 9pPCCzPNfpr It was found that the following was obtained.

[0437] 1 H-NMR.δ(CD2Cl2):7.32-7.39(m,2H),7.44-7. 56(m,5H),7.61(d,1H),7.64-7.69(m,6H),7.83 -7.91(m,6H),8.11(d,1H),8.17(d,1H),8.28(d ,2H),8.49-8.53(m,4H),9.18(d,1H),9.40(s,1 H). EXAMPLES

[0438] <Synthesis Example 9> In this example, an organic compound represented by structural formula (239) in Embodiment 1, which is one embodiment of the present invention, Compound 9-[4-(9'-phenyl-2,3'-bi-9H-carbazol-9-yl)fluor phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9pPCC The synthesis method of 9pPCCzPNfpr-02) is explained below. The structure of 2 is shown below.

[0439] [ka]

[0440] The synthesis method of 9-(4-chlorophenyl)naphtho[ 1',2':4,5]furo[2,3-b]pyrazine 1.76g, 9'-phenyl-2,3 2.22 g of '-bi-9H-carbazole and 27 mL of mesitylene were placed in a three-neck flask. The inside of the flask was degassed by stirring under reduced pressure, and sodium te rt-butoxide 1.09 g, tris(dibenzylideneacetone)dipalladium(0)( Abbreviation: Pd2(dba)3) 0.031g, 2-dicyclohexylphosphino-2',6 Add 0.045 g of '-dimethoxybiphenyl (abbreviation: S-Phos) and heat at 150°C for 6 hours. The mixture was stirred for a period of time to react.

[0441] After a predetermined time had elapsed, the obtained suspension was subjected to suction filtration, and the filter cake was washed with water and ethanol. The solid was purified by silica gel column chromatography using toluene as a developing solvent. After that, the target product was obtained by recrystallization with a mixed solvent of toluene and hexane (yellow solid). Total yield: 1.95 g (52%)

[0442] The resulting yellow solid (1.94 g) was purified by train sublimation. The purification conditions were: pressure 2.7 Pa, argon gas flow rate 18 mL / min, 38 The solid was heated at 0°C. After purification by sublimation, the target yellow solid was obtained in an amount of 1.62 g and a yield of 84%. The synthesis scheme is shown in the following formula (i-1).

[0443] [ka]

[0444] The yellow solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of the analysis using H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in FIG. As a result, the organic compound 9pPCCzPNfpr-02 represented by the above structural formula (239) was obtained. It was found that

[0445] 1 H-NMR.δ(CD2Cl2):7.28-7.31(m,1H),7.36(t, 1H),7.40-7.44(m,2H),7.46-7.51(m,3H),7.57 -7.69(m,6H),7.74(d,1H),8.78(d,1H),7.84(t ,1H),7.81-7.88(m,4H),8.10(d,1H),8.16(d,1 H),8.22(d,2H),8.28(d,1H),8.46(s,1H),8.50 (d,2H), 9.17(d,1H), 9.38(s,1H). EXAMPLES

[0446] <Synthesis Example 10> In this example, an organic compound represented by structural formula (244) in Embodiment 1, which is one embodiment of the present invention, was Compound 9-[3'-(6-phenylbenzo[b]naphtho[1,2-d]furan-8-yl )biphenyl-3-yl]naphtho[1',2':4,5]furo[2,3-b]pyrazine( The synthesis method of 9mBnfBPNfpr will be explained. The structure of fpr is shown below.

[0447] [ka]

[0448] The synthesis method of 9-(3-chlorophenyl)naphtho[1 ',2':4,5]furo[2,3-b]pyrazine 1.28g, 3-(6-phenylbenzo [b] Naphtho[1,2-d]furan-8-yl)phenylboronic acid pinacol ester 2 .26g, tripotassium phosphate 2.53g, tert-butyl alcohol 0.89g, diene Add 32 mL of ethylene glycol dimethyl ether (abbreviation: diglyme) to a three-neck flask. The flask was degassed by stirring under reduced pressure, and then paraacetate was added. Pd(II) (abbreviation: Pd(OAc)2) 8.8 mg, di(1-adamantyl)-n- Add 28 mg of butylphosphine (abbreviation: CataCXium A) and heat at 140°C for 8 hours. The mixture was stirred for half an hour and allowed to react.

[0449] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The compound was purified by silica gel column chromatography using toluene as a developing solvent. The target product was obtained by recrystallization from toluene (yellow solid, yield 0.66 g, yield 25%). The synthesis scheme is shown in formula (j-1) below.

[0450] [ka]

[0451] The yellow solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 The results of the analysis using H-NMR are shown below. As shown below. 1 The H-NMR chart is shown in FIG. As a result, the organic compound 9mBnfBPNfpr represented by the above structural formula (244) was obtained. It was discovered that...

[0452] 1 H-NMR.δ(CD2Cl2):7.24-7.28(m,3H),7.61-7. 72(m,5H),7.78-7.87(m,6H),7.98-8.00(m,3H) ,8.08(d,1H),8.11-8.15(m,3H),8.25(d,1H),8 .48(s,1H),8.51-8.53(m,2H),8.75(d,1H),9.1 5(d,1H),9.32(s,1H). EXAMPLES

[0453] <Synthesis Example 11> In this example, an organic compound represented by structural formula (245) in Embodiment 1, which is one embodiment of the present invention, Compound 9-[3'-(6-phenyldibenzothiophen-4-yl)biphenyl-3-yl 9mDBtBP The synthesis method of 9mDBtBPNfpr-02 will be explained. The structure is shown below.

[0454] [ka]

[0455] The synthesis method of 9-(3-chlorophenyl)naphtho[1 ',2':4,5]furo[2,3-b]pyrazine 1.19g, 3-(6-phenyldibenzo 1.97g of (4-phenyl-2-phenyl-4-phenyl)boronic acid pinacol ester, 1.97g of triphosphate 2.29g sodium, 0.82g tert-butyl alcohol, 0.5g diethylene glycol Put 29 mL of ethyl ether (abbreviation: diglyme) into a three-neck flask and replace the inside with nitrogen. The flask was degassed by stirring under reduced pressure, and then palladium(II) acetate (abbreviation : Pd(OAc)2) 16 mg, di(1-adamantyl)-n-butylphosphine (abbreviation 52 mg of CataCXium A was added, and the mixture was stirred at 140° C. for 15 hours to cause a reaction.

[0456] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The compound was purified by silica gel column chromatography using toluene as a developing solvent. The target product was obtained by recrystallization from toluene (yellow-white solid, yield 1.17 g). The synthesis scheme is shown in formula (k-1) below.

[0457] [ka]

[0458] The yellow-white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis results As shown below. Also, 1The H-NMR chart is shown in FIG. The organic compound 9mDBtBPNfpr-02 represented by the above structural formula (245) is It was found that it was obtained.

[0459] 1 H-NMR.δ(CD2Cl2):7.39(t,1H),7.47-7.51(m, 3H),7.58-7.67(m,6H),7.73(d,2H),7.78-7.85 (m,5H),8.02(s,1H),8.06(d,1H),8.10(d,1H), 8.18(d,1H),8.23(t,2H),8.49(s,1H),9.17(d, 1H),9.30(s,1H). EXAMPLES

[0460] <Synthesis Example 12> In this example, an organic compound represented by structural formula (246) in Embodiment 1, which is one embodiment of the present invention, Compound 9-{3-[6-(9,9-dimethylfluoren-2-yl)dibenzothiophene -4-yl]phenyl}naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation This section explains how to synthesize the 9mFDBtPNfpr. The structure of pr is shown below.

[0461] [ka]

[0462] The synthesis method of 9-(3-chlorophenyl)naphtho[1 ',2':4,5]furo[2,3-b]pyrazine 1.01g, 3-[6-(9,9-dimethyl (Dimethylfluoren-2-yl)dibenzothiophen-4-yl)phenylboronic acid 1.46 g, tripotassium phosphate 1.89 g, tert-butyl alcohol 0.67 g, diethylene Put 24 mL of glycol dimethyl ether (abbreviation: diglyme) into a three-neck flask. The inside of the flask was replaced with nitrogen. The flask was degassed by stirring under reduced pressure, and then palladium acetate was added. (II) (abbreviation: Pd(OAc)2) 27 mg, di(1-adamantyl)-n-butyl phosphatase Add 88 mg of sphingosine (abbreviation: CataCXium A) and stir at 140°C for 30 hours. , and reacted.

[0463] After a predetermined time had elapsed, the resulting suspension was filtered by suction and washed with water and ethanol. The compound was purified by silica gel column chromatography using toluene as a developing solvent. The target product was obtained by recrystallization from a mixed solvent of toluene and hexane (yellowish white solid). The yield was 0.75 g (37%). The synthesis scheme is shown in (l-1) below.

[0464] [ka]

[0465] The yellow-white solid obtained above was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR) analysis results As shown below. Also, 1 The H-NMR chart is shown in FIG. The organic compound 9mFDBtPNfpr represented by the above structural formula (246) was obtained. I realized that.

[0466] 1 H-NMR.δ(CD2Cl2):1.47(s,6H),7.27-7.32(m, 2H),7.38(d,1H),7.61-7.76(m,8H),7.79-7.85 (m,4H),7.89(d,1H),8.08(d,1H),8.13(d,1H), 8.24-8.31(m,3H),8.59(s,1H),9.14(d,1H),9. 31(s,1H). EXAMPLES

[0467] <Synthesis Example 13> In this example, an organic compound represented by structural formula (247) in Embodiment 1, which is one embodiment of the present invention, Compound 11-(3-naphtho[1',2':4,5]furo[2,3-b]pyrazine-9-yl 9mIc The synthesis method of 9mIcz(II)PNfpr is explained below. The structure of pr is shown below.

[0468] [ka]

[0469] The synthesis method of 9mIcz(II)PNfpr is shown in the synthesis scheme of formula (m-1) below. vinegar.

[0470] [ka] EXAMPLES

[0471] <Synthesis Example 14> In this example, an organic compound represented by structural formula (248) in Embodiment 1, which is one embodiment of the present invention, Compound, 3-naphtho[1',2':4,5]furo[2,3-b]pyrazin-9-yl-N, This article explains how to synthesize N-diphenylbenzenamine (abbreviation: 9mTPANfpr). The structure of 9mTPANfpr is shown below.

[0472] [ka]

[0473] The synthesis method of 9mTPANfpr is shown in the synthesis scheme of formula (n-1) below.

[0474] [ka] EXAMPLES

[0475] In this embodiment, the 10mDBt light-emitting device described in Example 9 is used as the light-emitting device according to one embodiment of the present invention. We fabricated a light-emitting device 8 using BPNfpr (structural formula (133)) as the light-emitting layer, and investigated its characteristics. The results of the measurements are shown below.

[0476] The element structure of the light-emitting element 8 produced in this example is the same as that shown in FIG. 11 in Example 2. The specific structure of each layer that constitutes the element structure is as shown in Table 12. The chemical formulas of the materials used in this example are shown below.

[0477] [Table 12]

[0478] [ka]

[0479] <Operation characteristics of light-emitting element 8> The operating characteristics of the fabricated light-emitting device 8 were measured. The measurements were performed at room temperature (25° C.). I went there for the atmosphere.

[0480] FIG. 47 shows the current density-luminance characteristics of the light-emitting element 8, FIG. 48 shows the voltage-luminance characteristics, and FIG. 49 shows the luminance-current efficiency characteristics. The characteristics are shown in Figure 49 and the voltage-current characteristics are shown in Figure 50.

[0481] Also, 1000cd / m 2 The main initial characteristic values ​​of the light-emitting element 8 in the vicinity are shown in Table 13 below. vinegar.

[0482] [Table 13]

[0483] 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. 51, the emission spectrum of the light-emitting element has a peak at about 626 nm. The light-emitting layer 913 has a peak of [Ir(dmpqn)2(acac)]. This suggests that it is due to luminescence.

[0484] Next, a reliability test was performed on the light-emitting element 8. The results of the reliability test are shown in FIG. In Figure 2, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is performed at 75mA / cm 2 At a constant current density A constant current drive test was carried out.

[0485] From the results of the reliability test, the organic compound 10mDBtBPNfpr, which is one embodiment of the present invention, It was found that the light-emitting element 8 used had high reliability. It can be said that the use of an organic compound having the above structure is useful for improving the reliability of a light-emitting element. . EXAMPLES

[0486] In this embodiment, the 12mDB described in Example 11 is used as the light-emitting element according to one aspect of the present invention. A light-emitting device 9 was fabricated using tBPPnfpr (structural formula (208)) in the light-emitting layer, and its characteristics were The measurement results are shown below.

[0487] The element structure of the light-emitting element 9 produced in this embodiment is the same as that shown in FIG. 11 in Example 2. The specific configuration of each layer that constitutes the element structure is as shown in Table 14. The chemical formulas of the materials used in this example are shown below.

[0488] [Table 14]

[0489] [ka]

[0490] <Operation characteristics of light-emitting element 9> The operating characteristics of the fabricated light-emitting device 9 were measured. The measurements were performed at room temperature (25° C.) I went there for the atmosphere.

[0491] FIG. 53 shows the current density-luminance characteristics of the light-emitting element 9, FIG. 54 shows the voltage-luminance characteristics, and FIG. 55 shows the luminance-current efficiency characteristics. The characteristics are shown in Figure 55 and the voltage-current characteristics are shown in Figure 56.

[0492] Also, 1000cd / m 2 The main initial characteristics of the light-emitting element 9 in the vicinity are shown in Table 15 below. vinegar.

[0493] [Table 15]

[0494] In addition, the light emitting element 9 is supplied with 2.5 mA / cm2 The emission spectrum when a current is applied at a current density of As shown in FIG. 57, the emission spectrum of the light-emitting element has a peak at about 626 nm. The light-emitting layer 913 has a peak of [Ir(dmpqn)2(acac)]. This suggests that it is due to luminescence.

[0495] Next, a reliability test was performed on the light-emitting element 9. The results of the reliability test are shown in FIG. In FIG. 8, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is performed at 75mA / cm 2 At a constant current density A constant current drive test was carried out.

[0496] From the results of the reliability test, the organic compound according to one embodiment of the present invention, 12mDBtBPPnfpr It was found that the light-emitting element 9 using the above-mentioned compound had high reliability. It can be said that using such an organic compound is useful for improving the reliability of the light-emitting element. do. EXAMPLES

[0497] In this example, the 9PCCzN The light-emitting device 10 using fpr (structural formula (123)) in the light-emitting layer, and the light-emitting device 10 described in Example 10 Light-emitting device 11 using PCCzNfpr (structural formula (156)) in the light-emitting layer, as described in Example 7 A light-emitting device 12 using the 9mPCCzPNfpr (structural formula (125)) as an emitting layer was The light-emitting layer was made of 9mPCCzPNfpr-02 (structural formula (126)) described in Example 8. Photonic device 13 emits light using 9pPCCzPNfpr (structural formula (238)) as described in Example 12. The light-emitting element 14 used in the layer was 9pPCCzPNfpr-02 (structural formula: (239)) was used as the light-emitting layer to fabricate light-emitting devices 15, and their characteristics were measured. The results are shown below.

[0498] The light-emitting elements 10, 11, 12, and 13 fabricated in this example The element structures of the light-emitting element 14 and the light-emitting element 15 are the same as those of the light-emitting element 3 shown in Example 3. The specific structure of each layer that constitutes the element structure is as shown in Table 16. The chemical formulas of the materials used in this example are shown below.

[0499] [Table 16]

[0500] [ka]

[0501] [ka]

[0502] <Operation characteristics of light-emitting element> The fabricated light-emitting elements 10, 11, 12, 13, 14, and The operating characteristics of the light-emitting element 15 were measured. The measurements were carried out in an atmosphere maintained at room temperature (25° C.). The experiment was conducted in an atmospheric condition.

[0503] The current density-luminance characteristics of each light-emitting element are shown in FIG. 59, the voltage-luminance characteristics in FIG. 60, and the luminance-current efficiency characteristics in FIG. The characteristics are shown in Figure 61 and the voltage-current characteristics are shown in Figure 62.

[0504] Also, 1000cd / m 2The main initial characteristics of each light-emitting element in the vicinity are shown in Table 17 below. vinegar.

[0505] [Table 17]

[0506] 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. 63, the emission spectrum of the light-emitting element has a peak at about 629 nm. The light-emitting layer 913 has a peak of [Ir(dmpqn)2(acac)]. This suggests that it is due to luminescence.

[0507] Next, a reliability test was carried out on each of the light-emitting elements. The results of the reliability test are shown in FIG. In FIG. 64, the vertical axis indicates normalized luminance (%) when the initial luminance is 100%, and the horizontal axis indicates the operation time (h) of the element. The reliability test was performed at 75mA / cm 2 At a current density of A constant current drive test was carried out in which a constant current was applied.

[0508] From the results of the reliability test, the organic compounds according to the present invention, 9PCCzNfpr and 10P CCzNfpr, 9mPCCzPNfpr, 9mPCCzPNfpr-02, 9pPCC Each emission using zPNfpr and 9pPCCzPNfpr-02 as the emission layer The device was found to have high reliability. It can be said that the use of the compound is useful in improving the reliability of the light-emitting element. EXAMPLES

[0509] <Synthesis Example 15> In this example, an organic compound represented by structural formula (158) in Embodiment 1, which is one embodiment of the present invention, Compound, 10-[4-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl) phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 10mP The synthesis method of 10mPCCzPNfpr is explained below. The structure is shown below.

[0510] [ka]

[0511] In addition, the synthesis method of 10mPCCzPNfpr is represented by the following formulas (o-1) to (o-4): The synthesis scheme is shown in the figure.

[0512] [ka]

[0513] [ka]

[0514] [ka]

[0515] [ka] EXAMPLES

[0516] <Synthesis Example 16> In this example, an organic compound represented by structural formula (178) in Embodiment 1, which is one embodiment of the present invention, Compound, 11-[(3'-dibenzothiophen-4-yl)biphenyl-3-yl]phenanthracene 11mDBtBP The synthesis method of 11mDBtBPPnfpr is explained below. As shown below.

[0517] [ka]

[0518] In addition, the synthesis method of 11mDBtBPPnfpr is represented by the following formulas (p-1) to (p-7). The synthesis scheme is shown below.

[0519] [ka]

[0520] [ka]

[0521] [ka]

[0522] [ka]

[0523] [ka]

[0524] [ka]

[0525] [ka] EXAMPLES

[0526] <Synthesis Example 17> In this example, an organic compound represented by structural formula (240) in Embodiment 1, which is one embodiment of the present invention, is used. Compound, 10-[3-(9'-phenyl-3,3'-bi-9H-carbazol-9-yl) phenyl]naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 10pP The synthesis method of 10pPCCzPNfpr is explained below. The structure is shown below.

[0527] [ka]

[0528] The synthesis method of 10pPCCzPNfpr is represented by the following formulas (q-1) to (q-4): The synthesis scheme is shown in the figure.

[0529] [ka]

[0530] [ka]

[0531] [ka]

[0532] [ka] EXAMPLES

[0533] <Synthesis Example 18> In this example, an organic compound represented by structural formula (242) in Embodiment 1, which is one embodiment of the present invention, Compound 9-[3-(7H-dibenzo[c,g]carbazol-7-yl)phenyl]naphthalene To[1',2':4,5]furo[2,3-b]pyrazine (abbreviation: 9mcgDBCzPNf The synthesis method of 9mcgDBCzPNfpr is explained below. show.

[0534] [ka]

[0535] In addition, the synthesis method of 9mcgDBCzPNfpr is represented by the following formulas (r-1) to (r-4): The synthesis scheme is shown below.

[0536] [ka]

[0537] [ka]

[0538] [ka]

[0539] [ka] EXAMPLES

[0540] <Synthesis Example 19> In this example, an organic compound represented by structural formula (249) in Embodiment 1, which is one embodiment of the present invention, Compound 9-{3'-[6-(biphenyl-3-yl)dibenzothiophen-4-yl]biphenyl phenyl-3-yl}naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation The synthesis method of 9mDBtBP Nfpr-03 is explained below. The structure of Nfpr-03 is shown below.

[0541] [ka]

[0542] The synthesis method of 9mDBtBPNfpr-03 is shown in the following formulas (s-1) to (s-4). The synthesis scheme is shown below.

[0543] [ka]

[0544] [ka]

[0545] [ka]

[0546] [ka] EXAMPLES

[0547] <Synthesis Example 20> In this example, an organic compound represented by structural formula (250) in Embodiment 1, which is one embodiment of the present invention, is used. Compound 9-{3'-[6-(biphenyl-4-yl)dibenzothiophen-4-yl]biphenyl phenyl-3-yl}naphtho[1',2':4,5]furo[2,3-b]pyrazine (abbreviation The synthesis method of 9mDBtBP Nfpr-04 is explained below. The structure of Nfpr-04 is shown below.

[0548] [ka]

[0549] The synthesis method of 9mDBtBPNfpr-04 is shown in the following formula (t-1) to formula (t-4). The synthesis scheme is shown below.

[0550] [ka]

[0551] [ka]

[0552] [ka]

[0553] [ka] EXAMPLES

[0554] <Synthesis Example 21> In this example, an organic compound represented by structural formula (251) in Embodiment 1, which is one embodiment of the present invention, Compound, 11-[3'-(6-phenyldibenzothiophen-4-yl)biphenyl-3- 11 yl]phenanthro[9',10':4,5]furo[2,3-b]pyrazine (abbreviation: The synthesis method of mDBtBPpnfpr-02) is explained below. The structure of Pnfpr-02 is shown below.

[0555] [ka]

[0556] In addition, the synthesis method of 11mDBtBPPnfpr-02 is shown in the following formula (u-1) to the following formula (u- 7) is shown in the synthesis scheme.

[0557] [ka]

[0558] [ka]

[0559] [ka]

[0560] [ka]

[0561] [ka]

[0562] [ka]

[0563] [ka] EXAMPLES

[0564] In this embodiment, the 12mDB described in Example 11 is used as the light-emitting element according to one aspect of the present invention. A light-emitting device 16 was fabricated using tBPPnfpr (structural formula (208)) in the light-emitting layer, and a comparative light-emitting device As an optical element, 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl] Dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) is used for the light-emitting layer. A comparative light-emitting element 17 was fabricated, and the characteristics thereof were measured, and the results are shown below.

[0565] The element structures of the light-emitting element 16 and the comparative light-emitting element 17 fabricated in this example are the same as those in Examples The structure is the same as that shown in FIG. 11, but the specific configuration of each layer constituting the element structure is The details are as shown in Table 18. The chemical formulas of the materials used in this example are shown below.

[0566] [Table 18]

[0567] [ka]

[0568] <Operation characteristics of light-emitting element> The operating characteristics of the fabricated light-emitting element 16 and the comparative light-emitting element 17 were measured. was carried out at room temperature (atmosphere maintained at 25°C).

[0569] FIG. 65 shows the current density-luminance characteristics of the light-emitting element 16 and the comparative light-emitting element 17, and FIG. 66 shows the voltage-luminance characteristics of the light-emitting element 16 and the comparative light-emitting element 17. FIG. 66 shows the luminance-current efficiency characteristics, FIG. 67 shows the voltage-current characteristics, and FIG. 68 shows the voltage-current characteristics.

[0570] Also, 1000cd / m 2 The main initial values ​​of the light-emitting element 16 and the comparative light-emitting element 17 in the vicinity The properties are shown in Table 19 below.

[0571] [Table 19]

[0572] 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. 69, the emission spectrum of each light-emitting element has a peak at around 586 nm. The peak is the peak of [Ir(dppm)2(acac)] contained in the light-emitting layer 913. This suggests that it is due to luminescence.

[0573] Next, a reliability test was performed on each light-emitting element. The results of the reliability test are shown in FIG. At 0, the vertical axis shows the normalized luminance (%) when the initial luminance is 100%, and the horizontal axis shows the The reliability test is performed at 75mA / cm 2 At a constant current density A constant current drive test was carried out.

[0574] From the results of the reliability test, the organic compound according to one embodiment of the present invention, 12mDBtBPPnfpr The light-emitting device 16 using 2mDBTBPDBq-II is compared with the comparative light-emitting device 17 using 2mDBTBPDBq-II. It was found that the 12mDBtBPPnfpr and 2mDBT The difference in the molecular structure of BPDBq-II, i.e., the phenanthrofuropyrazine skeleton and dibenzyl This is believed to be due to the difference in the benzoquinoxaline structure. This shows the robustness of the pyrazine derivative. It can be said that the use of an organic compound is useful in improving the reliability of a light-emitting device. [Explanation of symbols]

[0575] 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 Board 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. A light-emitting layer is disposed between an anode and a cathode, The light-emitting element has an organic compound represented by formula (G1) between the light-emitting layer and the cathode. 【Chemistry 1】 (In the formula, Q represents oxygen or sulfur. Also, Ar １ represents a substituted or unsubstituted fused aromatic ring. １ and R ２ each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R １ and R ２ At least one of has a skeleton having any one of a substituted or unsubstituted diarylamino group, a substituted or unsubstituted fused aromatic hydrocarbon ring, or a substituted or unsubstituted π-excessive fused heteroaromatic ring.

2. A light-emitting layer is disposed between an anode and a cathode, The light-emitting element has an organic compound represented by formula (G1) between the light-emitting layer and the cathode. 【Chemistry 2】 (In the formula, Q represents oxygen or sulfur. Also, Ar １ represents any one of substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, and substituted or unsubstituted chrysene. １ and R ２ each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R １ and R ２ At least one of has a skeleton having any one of a substituted or unsubstituted diarylamino group, a substituted or unsubstituted fused aromatic hydrocarbon ring, or a substituted or unsubstituted π-excessive fused heteroaromatic ring.

3. In claim 1 or 2, Ar in the formula (G1) １ A light-emitting element represented by any one of the following formulas (t1) to (t3). 【Chemistry 3】 (In the formula, R ３ ~R ２４ each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. * represents a bonding portion in formula (G1).

4. In any one of claims 1 to 3, The formula (G1) is any one of the following formulas (G1-1) to (G1-4): 【Chemistry 4】 (In the formula, Q represents oxygen or sulfur. Also, R １ and R ２ each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R １ and R ２ At least one of R has a skeleton having any one of a substituted or unsubstituted diarylamino group, a substituted or unsubstituted fused aromatic hydrocarbon ring, and a substituted or unsubstituted π-excessive fused heteroaromatic ring. ３ ~R ８ and R １７ ~R ２４ each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

5. In any one of claims 1 to 4, The light-emitting device, wherein the fused aromatic hydrocarbon ring is any one of a naphthalene skeleton, a fluorene skeleton, a triphenylene skeleton, and a phenanthrene skeleton.

6. In any one of claims 1 to 5, The light-emitting device, wherein the π-excess condensed heteroaromatic ring is any one of a dibenzothiophene skeleton, a dibenzofuran skeleton, and a carbazole skeleton.

7. In any one of claims 1 to 6, R in the formula (G1) １ and R ２ each independently represents hydrogen or a group having a total of 1 to 100 carbon atoms; R １ and R ２ at least one of the above is a group represented by formula (u1): 【Chemistry 5】 (In the formula, α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and n represents an integer of 0 to 4. １ represents a substituted or unsubstituted aryl group having a total of 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms. In addition, * represents a bonding site in formula (G1).

8. In claim 7, A in the formula (u1) １ is represented by the formula (A １ -1) to Formula (A １ -17). 【Chemistry 6】 (In the formula, R Ａ１ ~R Ａ１１ each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

9. In claim 7 or claim 8, A light-emitting element, wherein α in the formula (u1) is any one of the formulas (Ar-1) to (Ar-14). 【Chemistry 7】 (In the formula, R Ｂ１ ~R Ｂ１４ each independently represents any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

10. In any one of claims 7 to 9, In the formula (u1), n ​​is an integer of 1 to 4.

11. In any one of claims 7 to 10, A light-emitting device, wherein α in the formula (u1) is a phenylene group.

12. A light-emitting layer is disposed between an anode and a cathode, A light-emitting device having an organic compound represented by any one of formulas (100), (123), (125), (126), (133), (156), (208), (238), (239), (244), (245), (246), (247), (248), (158), (178), (240), (242), (249), (250), and (251) between the light-emitting layer and the cathode. 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】

13. A light-emitting element according to any one of claims 1 to 12, At least one of a transistor or a substrate; A light emitting device having the above structure.

14. A light emitting device according to claim 13; At least one of a microphone, a camera, an operation button, an external connection part, or a speaker; An electronic device having the

15. A light-emitting element according to any one of claims 1 to 12, At least one of a housing, a cover, or a support base; A lighting device having the above structure.

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