Compound

Abstract

To provide a novel anthracene derivative, a novel organic compound, a light-emitting element with high emission efficiency, a light-emitting element which can emit blue light with high color purity, and a light-emitting device and an electronic device with reduced power consumption.SOLUTION: The anthracene derivative is represented by formula (1). (In the formula, Ar1 and Ar2 are each an aryl group having 6 to 25 carbon atoms; α and β are each an arylene group having 6 to 25 carbon atoms; R1 is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 25 carbon atoms; R2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 25 carbon atoms, a halogen group, or a haloalkyl group; R11 to R18 are each hydrogen or an alkyl group having 1 to 4 carbon atoms) SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an organic compound, an anthracene derivative, and a light-emitting element using the anthracene derivative. The present invention relates to a light-emitting device, a light-emitting device, and an electronic device. [Background technology]

[0002] The light-emitting element has a structure in which a layer containing an organic compound is sandwiched between a pair of electrodes. The device can be made thin and lightweight, emits light when a direct current is applied, and is different from liquid crystals. Furthermore, such light emitting elements can be used in a matrix. Light-emitting devices arranged in a rectangular pattern, i.e., passive matrix light-emitting devices and active matrix light-emitting devices, Optical devices have the advantage of a wider viewing angle and better visibility than conventional LCD devices. For these reasons, light-emitting devices are expected to be applied to next-generation flat panel displays. The light-emitting element is called an electroluminescent element, or EL element. It may also be possible.

[0003] The light-emitting element injects electrons from a cathode into a layer containing an organic compound sandwiched between a pair of electrodes. At the same time, holes are injected from the anode, and the device is driven by the electrons injected from the cathode. The holes injected from the anode recombine in the layer containing the organic compound to form molecular excitons. When the molecular exciton returns to the ground state, it releases energy. When emitted as light of wavelengths corresponding to visible light, it can be recognized as luminescence. The excited states of organic compounds exist as singlet and triplet states, and light emission occurs from either of these excited states. But it is possible.

[0004] The emission wavelength of a light-emitting element is determined by the energy difference between the ground state and the excited state formed by recombination. Therefore, the structure of the molecule that is responsible for light emission is determined appropriately. By appropriately selecting and modifying the materials, it is possible to obtain any luminescent color. By manufacturing a light-emitting device using light-emitting elements that can emit red, blue, and green light, a full-color display can be realized. It is possible to fabricate a light-emitting device capable of displaying light.

[0005] To produce a full-color light-emitting device with excellent color reproducibility, a highly reliable and Red, blue, and green light-emitting elements with excellent color purity are required. High reliability and excellent color purity have been achieved for blue and green light-emitting elements. Regarding color light-emitting elements, light-emitting elements with sufficient efficiency and color purity have not yet been realized. For example, Non-Patent Document 1 reports a blue light-emitting device with relatively high reliability. However, sufficient luminous efficiency and color have not been achieved. [Prior art documents] [Non-patent literature]

[0006] [Non-Patent Document 1] J. Shi et al., Applied Physics Letters, Vol. 80, No. 17, pp. 3201-3203, 2002. Summary of the Invention [Problem to be solved by the invention]

[0007] In view of the above problems, the present invention provides a novel anthracene derivative and a novel organic compound. The purpose is to

[0008] Another object of the present invention is to provide a light-emitting element with high luminous efficiency. An object of the present invention is to provide a light-emitting element that can emit light.

[0009] Another object of the present invention is to provide a light-emitting device and an electronic device with reduced power consumption. [Means for solving the problem]

[0010] As a result of extensive research, the present inventors have found that an anthracene derivative represented by the following general formula (1) Therefore, one aspect of the present invention is to provide a compound represented by the following general formula (1): It is an anthracene derivative.

[0011] [ka]

[0012] In the above general formula (1), Ar 1 and Ar 2 may be the same or different. represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and α and β are each the same. may be the same or different and represent a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. represents a methyl group, and R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted group. R represents an aryl group having 6 to 25 carbon atoms, a halogen group, or a haloalkyl group. 1 1 ~R 18 may be the same or different and are each hydrogen or an alkyl group having 1 to 4 carbon atoms. represents an alkyl group.

[0013] Another aspect of the present invention is an anthracene derivative represented by the following general formula (2).

[0014] [ka]

[0015] In the above general formula (2), Ar 1 is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms α and β may be the same or different and represent substituted or unsubstituted carbon atoms. represents an arylene group having 6 to 25 carbon atoms; R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. represents an unsubstituted aryl group having 6 to 25 carbon atoms, and R 2 is hydrogen or an alkyl group with 1 to 4 carbon atoms. an alkyl group, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a halogen group; or a haloalkyl group, R 3 ~R 7 may be the same or different, a carbon atom, an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group R 11 ~R 18 may be the same or different and are each hydrogen or It represents an alkyl group having 1 to 4 carbon atoms.

[0016] Another aspect of the present invention is an anthracene derivative represented by the following general formula (3).

[0017] [ka]

[0018] In the above general formula (3), Ar 1 and Ar 2 may be the same or different. represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and α represents a substituted or unsubstituted represents an arylene group having 6 to 25 carbon atoms, and R 1 is an alkyl group having 1 to 4 carbon atoms or a substituted or an unsubstituted aryl group having 6 to 25 carbon atoms, R 2 is hydrogen or carbon number 1-4 or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a halogen atom represents a group or a haloalkyl group, and R 11 ~R 18 are the same or different It preferably represents hydrogen or an alkyl group having 1 to 4 carbon atoms.

[0019] Another aspect of the present invention is an anthracene derivative represented by the following general formula (4).

[0020] [ka]

[0021] In the above general formula (4), Ar 1 is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms α represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms; R 1 is carbon represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 4 carbon atoms. 25 aryl group, halogen group, or haloalkyl group, R 3 ~R 7 Ha, so They may be the same or different and may be hydrogen, an alkyl group having 1 to 4 carbon atoms, or halogen. R represents either a haloalkyl group or a haloalkyl group. 11 ~R 18 are the same but different It may be hydrogen or an alkyl group having 1 to 4 carbon atoms.

[0022] Another aspect of the present invention is an anthracene derivative represented by the following general formula (5).

[0023] [ka]

[0024] In the above general formula (5), Ar 1 is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms represents R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 25 carbon atoms. represents an aryl group represented by the formula: 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. represents an unsubstituted aryl group having 6 to 25 carbon atoms, a halogen group, or a haloalkyl group; and R 3 ~R 7 may be the same or different and are each hydrogen or a group having 1 to 4 carbon atoms. represents either an alkyl group, a halogen group, or a haloalkyl group, and R 11 ~R 1 8 may be the same or different and each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. represents R 19 ~R 22 may be the same or different and are hydrogen or a group having 1 carbon atom. It represents an alkyl group having from 1 to 4 carbon atoms, or an alkoxy group having from 1 to 4 carbon atoms.

[0025] Another aspect of the present invention is an anthracene derivative represented by the following general formula (6).

[0026] [ka]

[0027] In the above general formula (6), R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted group. represents a substituted aryl group having 6 to 25 carbon atoms, and R 2 is hydrogen or alkyl having 1 to 4 carbon atoms a group, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a halogen group, or represents a haloalkyl group, and R 3 ~R 7 may be the same or different, and may be hydrogen or or an alkyl group having 1 to 4 carbon atoms, or a halogen group, or a haloalkyl group. represents R 11 ~R 18 may be the same or different, and are hydrogen or represents an alkyl group having 1 to 4 carbon atoms; R 19 ~R 27 may be the same or different, It represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

[0028] Another aspect of the present invention is an anthracene derivative represented by the following structural formula (7).

[0029] [ka]

[0030] Another aspect of the present invention is a light-emitting element containing the anthracene derivative. The light-emitting element is characterized in that the above anthracene derivative is contained between electrodes.

[0031] In addition, the anthracene derivatives have high luminous efficiency and are therefore preferably used in the light-emitting layer. Therefore, one aspect of the present invention is a light-emitting device having a light-emitting layer between a pair of electrodes, the light-emitting layer comprising the above-mentioned anthracene derivative. The light-emitting device is characterized by including a conductor.

[0032] Furthermore, the light-emitting device of the present invention thus obtained can achieve a long life. Light-emitting devices (image display devices) that use these as optical elements can also achieve a long lifespan. Therefore, the present invention also includes a light-emitting device and an electronic device using the light-emitting element of the present invention.

[0033] The light-emitting device of the present invention includes a light-emitting element containing the above-described anthracene derivative and a light-emitting element that controls light emission from the light-emitting element. The light emitting device in this specification is characterized by having a control circuit for controlling the light emitting element. This includes image display devices using light-emitting elements. Also, light-emitting elements with connectors, such as anisotropic conductors, Conductive film or TAB (Tape Automated Bonding) tape Or a module with a TCP (Tape Carrier Package) attached modules with printed wiring boards attached to the ends of TAB tape or TCP, or light-emitting The IC (integrated circuit) is directly mounted on the element using the COG (Chip On Glass) method. Furthermore, light-emitting devices include all modules that are used in lighting equipment, etc. This also includes equipment.

[0034] Further, electronic devices using the light-emitting element of the present invention in a display portion are also included in the category of the present invention. Therefore, the electronic device of the present invention has a display portion, and the display portion includes the above-described light-emitting element and the light-emitting element. and a control circuit for controlling the light emission of the light source.

[0035] In addition, the organic compounds used in synthesizing the anthracene derivatives of the present invention are also novel substances. Therefore, the organic compounds used in synthesizing the anthracene derivatives of the present invention are also Therefore, one aspect of the present invention is an organic compound represented by the following general formula (8): It is a thing.

[0036] [ka]

[0037] In the above general formula (8), Ar 2 is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms β represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms; R 1 is carbon represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 4 carbon atoms. 25 represents an aryl group, a halogen group, or a haloalkyl group.

[0038] Another aspect of the present invention is an organic compound represented by the following general formula (9).

[0039] [ka]

[0040] In the above general formula (9), β represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms. represents R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 25 carbon atoms. represents an aryl group, and R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or represents an unsubstituted aryl group having 6 to 25 carbon atoms, a halogen group, or a haloalkyl group; , R 3 ~R 7 may be the same or different and are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. It represents either an alkyl group, a halogen group, or a haloalkyl group.

[0041] Another aspect of the present invention is an organic compound represented by the following general formula (10):

[0042] [ka]

[0043] In the above general formula (10), Ar 2 is a substituted or unsubstituted aryl having 6 to 25 carbon atoms represents a group, and R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 2 carbon atoms. 5 represents an aryl group, and R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. or an unsubstituted aryl group having 6 to 25 carbon atoms, or a halogen group, or a haloalkyl group represent.

[0044] Another aspect of the present invention is an organic compound represented by the following general formula (11):

[0045] [ka]

[0046] In the above general formula (11), R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. represents a substituted aryl group having 6 to 25 carbon atoms, and R 2 is hydrogen or alkyl having 1 to 4 carbon atoms. a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a halogen group, or represents a haloalkyl group, and R 3 ~R 7 may be the same or different, and each may be hydrogen, or an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group Represents.

[0047] Another aspect of the present invention is an organic compound represented by the following general formula (12):

[0048] [ka]

[0049] In the above general formula (12), R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group. represents a substituted aryl group having 6 to 25 carbon atoms, and R 2 is hydrogen or alkyl having 1 to 4 carbon atoms. a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a halogen group, or represents a haloalkyl group, and R 3 ~R 7 may be the same or different, and each may be hydrogen, or an alkyl group having 1 to 4 carbon atoms, a halogen group, or a haloalkyl group Represents.

[0050] Another aspect of the present invention is an organic compound represented by the following structural formula (13).

[0051] [ka] [Effects of the Invention]

[0052] The anthracene derivative of the present invention has high luminous efficiency. is capable of emitting blue light with high color purity.

[0053] Furthermore, by using the anthracene derivative of the present invention, a light-emitting element with high luminous efficiency can be obtained. In addition, a light-emitting element that emits blue light with high color purity can be obtained.

[0054] Furthermore, by using the anthracene derivative of the present invention, a light-emitting device with reduced power consumption can be obtained. and electronic devices. [Brief explanation of the drawings]

[0055] [Figure 1] 1A and 1B are diagrams illustrating a light-emitting element of the present invention. [Figure 2] 1A and 1B are diagrams illustrating a light-emitting element of the present invention. [Figure 3] 1A and 1B are diagrams illustrating a light-emitting element of the present invention. [Figure 4] 1A and 1B illustrate a light-emitting device of the present invention. [Figure 5] 1A and 1B illustrate a light-emitting device of the present invention. [Figure 6] 1A to 1C are diagrams illustrating electronic devices of the present invention. [Figure 7] 1A and 1B are diagrams illustrating a lighting device of the present invention. [Figure 8] 1A and 1B are diagrams illustrating a lighting device of the present invention. [Figure 9] 1A and 1B are diagrams illustrating a lighting device of the present invention. [Figure 10] 1 shows the 1H NMR chart of 4-(9-phenyl-9H-carbazol-3-yl)diphenylamine (abbreviation: PCBA). [Figure 11] 1 shows the 1H NMR chart of 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA). [Figure 12] FIG. 1 shows the absorption spectrum and emission spectrum of 4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA) in a toluene solution. [Figure 13] 1 shows the absorption spectrum and emission spectrum of a thin film of 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA). [Figure 14] 10A to 10C illustrate a light-emitting element according to Example 2. [Figure 15] FIG. 10 is a graph showing current density-luminance characteristics of the light-emitting element fabricated in Example 2. [Figure 16] FIG. 10 shows voltage-luminance characteristics of the light-emitting element fabricated in Example 2. [Figure 17] FIG. 10 shows luminance-current efficiency characteristics of the light-emitting element fabricated in Example 2. [Figure 18] FIG. 10 is a graph showing luminance vs. external quantum efficiency characteristics of the light-emitting element fabricated in Example 2. [Figure 19] FIG. 10 shows an emission spectrum of a light-emitting element fabricated in Example 2. [Figure 20] 10A to 10C illustrate a light-emitting element according to Example 3. [Figure 21] FIG. 10 is a graph showing current density-luminance characteristics of the light-emitting element fabricated in Example 3. [Figure 22] FIG. 10 shows voltage-luminance characteristics of the light-emitting element fabricated in Example 3. [Figure 23] FIG. 10 shows luminance-current efficiency characteristics of the light-emitting element fabricated in Example 3. [Figure 24] FIG. 10 is a graph showing the luminance-external quantum efficiency characteristics of the light-emitting element fabricated in Example 3. [Figure 25] FIG. 10 shows an emission spectrum of a light-emitting element fabricated in Example 3. [Figure 26] FIG. 10 shows the results of a continuous lighting test of the light-emitting element fabricated in Example 2. [Figure 27] FIG. 10 shows the results of a continuous lighting test of the light-emitting element fabricated in Example 3. [Figure 28] 1 shows a 1H NMR chart of 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA). [Figure 29] 1 is a diagram showing the absorption spectrum of 4-[4-(10-phenyl-9-anthryl)phenyl]-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA) in a toluene solution. [Figure 30] FIG. 1 shows the emission spectrum of 4-[4-(10-phenyl-9-anthryl)phenyl]-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA) in a toluene solution. [Figure 31] FIG. 1 shows the absorption spectrum of a thin film of 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA). [Figure 32] FIG. 1 shows an emission spectrum of a thin film of 4-[4-(10-phenyl-9-anthryl)phenyl]-4′-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPBA). [Figure 33] FIG. 10 is a graph showing current density-luminance characteristics of the light-emitting element fabricated in Example 5. [Figure 34] FIG. 10 shows voltage-luminance characteristics of the light-emitting element fabricated in Example 5. [Figure 35] FIG. 10 shows luminance-current efficiency characteristics of the light-emitting element fabricated in Example 5. [Figure 36] FIG. 10 shows an emission spectrum of the light-emitting element fabricated in Example 5. DETAILED DESCRIPTION OF THE INVENTION

[0056] Hereinafter, embodiments 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 thereof may be changed without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications may be made to the present invention. The present invention is not limited to the description of the illustrated embodiment.

[0057] (Embodiment 1) In this embodiment, an anthracene derivative of the present invention will be described.

[0058] The anthracene derivative of the present invention is an anthracene derivative represented by general formula (1).

[0059] [ka]

[0060] In the above general formula (1), Ar 1 and Ar 2 may be the same or different. represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and α and β are each the same. may be the same or different and represent a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, R 1 is an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. represents a methyl group, and R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted group. R represents an aryl group having 6 to 25 carbon atoms, a halogen group, or a haloalkyl group. 1 1 ~R 18 may be the same or different and are each hydrogen or an alkyl group having 1 to 4 carbon atoms. represents an alkyl group.

[0061] In the above general formula (1), Ar 1 and Ar 2 Examples of the substituent represented by the formula ( Examples of the structures shown in Ar-1) to (Ar-19) are Ar 1 A carbon number of 1 to 4 Ar may have an alkyl group or an alkoxy group having 1 to 4 carbon atoms. 1 carbon number 1~ By having an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, the anionic surfactant of the present invention can be Since the solubility of the anthracene derivative is increased, the anthracene derivative of the present invention can be used to prepare ethylenediamine by a wet method. This is preferable when a light-emitting device is produced.

[0062] [ka]

[0063] In the general formula (1), the structure represented by α includes, for example, (α-1) to ( α-12) is an alkyl group having 1 to 4 carbon atoms, or α may be an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. By having an alkoxy group having 1 to 4 prime numbers, the solubility of the anthracene derivative of the present invention is improved. Therefore, it is possible to manufacture a light-emitting element by a wet process using the anthracene derivative of the present invention. do.

[0064] [ka]

[0065] In the general formula (1), the structure represented by β includes, for example, (β-1) to ( β-10) is an example of the structure shown.

[0066] [ka]

[0067] In addition, in the general formula (1), R 1 Examples of the substituent represented by (R1-1 ) to (R1-21).

[0068] [ka]

[0069] In addition, in the general formula (1), R 2 Examples of the substituent represented by (R2-1 ) to (R2-24).

[0070] [ka]

[0071] Specific examples of the anthracene derivative of the present invention include the following (100) to (101): Examples of the anthracene derivatives of the formula (164) are also possible. However, the present invention is not limited to these. I can't.

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] Various reactions can be applied to synthesize the anthracene derivative of the present invention. For example, The compound can be synthesized by using the synthesis methods shown in the following synthesis schemes (a-1) to (a-3). can be done.

[0090] [ka]

[0091] First, 9-halogenated-10-arylanthracene (compound 1) and halogenated arylanthracene The aryl boronic acid or organoboron compound of aryl halide (compound 7) was reacted with palladium. The aryl halides were then coupled via Suzuki-Miyaura reaction using a fluorine catalyst to give 9-(aryl halides). 10-arylanthracene (compound 2) can be obtained. In the synthesis scheme, X 1 teeth represents a halogen or a triflate group, and X 2 represents a halogen. 1 If is a halogen, X 1 and X 2 may be the same or different. Preferred halogens are iodine and bromine. X 1 is iodine, X 2 The combination of R and bromine is more preferable. 100 and R 10 1 represents hydrogen or an alkyl group having 1 to 6 carbon atoms, and R 100 and R 101 is the same They may be different from each other and may be bonded to each other to form a ring. 1 is a substitution or an unsubstituted aryl group having 6 to 25 carbon atoms. It represents an arylene group having 6 to 25 carbon atoms. Examples of suitable palladium catalysts include palladium(II) acetate, tetrakis(triphenylphosphine), and Examples of catalysts that can be used include palladium(0), but these are not the only catalysts that can be used. In the synthesis scheme (a-1), the palladium catalyst that can be used is The ligands include tri(orthotolyl)phosphine, triphenylphosphine, and triphenylphosphine. Examples of the coordination of palladium catalysts that can be used include cyclohexylphosphine. The molecules that can be used in the synthesis scheme (a-1) are not limited to these. Suitable bases include organic bases such as sodium tert-butoxide and potassium carbonate. However, the bases that can be used are not limited to these. In the synthesis scheme (a-1), the solvent that can be used is a mixture of toluene and water. Mixed solvents, mixed solvents of alcohols such as toluene and ethanol and water, mixed solvents of xylene and water solvents, mixed solvents of alcohols such as xylene and ethanol and water, mixed solvents of benzene and water, Mixed solvents of alcohol and water, such as benzene and ethanol, ethylene glycol dimethyl ether In particular, a mixture of toluene and water, or a mixture of toluene and water, A mixed solvent of ethanol and water is more preferable. However, the solvents that can be used are It is not limited to the above.

[0092] [ka]

[0093] On the other hand, halogenated diarylamine (compound 3) and 9H-carbazole-3-boronic acid Alternatively, a compound (compound 4) in which the 3-position of 9H-carbazole is substituted with an organic boron is used. Radium-catalyzed Suzuki-Miyaura coupling affords diarylamine at the 3-position. In the synthesis scheme, a carbazole compound (compound 5) substituted with A can be obtained. r 2 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and X 4 is halogen or thiazol- It represents a fluorine atom, and examples of halogen include iodine and bromine. or an unsubstituted arylene group having 6 to 25 carbon atoms. 1 is an alkyl group with 1 to 4 carbon atoms. R represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. 2 is hydrogen or an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. represents a halogen group, a halogen group, or a haloalkyl group. 102 and R 103 teeth, represents hydrogen or an alkyl group having 1 to 6 carbon atoms, and R 102 and R 103 are the same but different They may be bonded to each other to form a ring. In the present invention, examples of the palladium catalyst that can be used include palladium (II) acetate, tetrachloromethane, and the like. Examples include bis(triphenylphosphine)palladium(0), but The catalysts that can be used in the synthesis scheme (a-2) are not limited to these. The ligands of the palladium catalyst that can be used are tri(ortho-tolyl)phosphine and tri(ortho-tolyl)phosphine. Examples of usable phosphine include phenylphosphine and tricyclohexylphosphine. The ligands that can be used are not limited to these. Examples of bases that can be used include organic bases such as sodium tert-butoxide and calcium carbonate. However, the bases that can be used are not limited to these. In the synthesis scheme (a-2), the solvent that can be used is toluene. Mixed solvents of toluene and water, mixed solvents of alcohol and water such as toluene and ethanol, mixed solvents of xylene and water mixed solvents of alcohols such as xylene and ethanol and water; mixed solvents of benzene and water Solvents, mixed solvents of alcohols such as benzene and ethanol and water, ethylene glycol dimethyl In particular, a mixture of toluene and water, or A mixed solvent of toluene, ethanol and water is more preferable. are not limited to these.

[0094] [ka]

[0095] Then, the 9-(halogenated aryl)-10-aryl obtained in the synthesis scheme (a-1) The compound (compound 2) and the compound (compound 3) obtained by the synthesis scheme (a-2) were The substituted carbazole compound (compound 5) was reacted with the hydroxyl group of the hydroxyl group using a palladium catalyst. The Cathode-Glycosides can be obtained by the Buchwald-Buchwald reaction or the Ullmann reaction using copper or copper compounds. By coupling the compound 6 with the compound 6, the anthracene derivative of the present invention can be obtained. In the synthesis scheme (a-3), when the Hartwig-Buchwald reaction is carried out, Palladium catalysts that can be used include bis(dibenzylideneacetone)palladium. (0), palladium(II) acetate, etc., but the catalysts that can be used are In the synthesis scheme (a-3), usable palladium compounds include, but are not limited to, The ligands for the catalyst include tri(tert-butyl)phosphine and tri(n-hexyl)phosphine. ) phosphine, tricyclohexylphosphine, etc. The ligands that can be used are not limited to these. Examples of bases that can be used include organic bases such as sodium tert-butoxide and calcium carbonate. However, the bases that can be used are not limited to these. In the synthesis scheme (a-3), the solvent that can be used is toluene. Examples of solvents that can be used include benzene, xylene, benzene, and tetrahydrofuran. The solvents that can be used are not limited to these. In the synthesis scheme (a-3), R 104 and R 105 teeth , halogen, acetyl group, etc., and examples of halogen include chlorine, bromine, and iodine. Also, R 104 is iodine, or copper(I) iodide, 105 Copper acetate is an acetyl group (II) is preferred. The copper compound used in the reaction is not limited to these. In addition to the copper compound, copper can be used. Examples of the base that can be used include inorganic bases such as potassium carbonate. The base is not limited to these. The solvent that can be used is 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pi. Examples include rimidinone (abbreviated as DMPU), toluene, xylene, and benzene. The solvents that can be used are not limited to these. In the Ullmann reaction, the reaction temperature is At temperatures above 0°C, the target product can be obtained in a shorter time and with a higher yield. It is preferable to use silane. The reaction temperature is more preferably 150°C or higher. In the synthesis scheme, Ar 1 and A r 2 may be the same or different, and may be substituted or unsubstituted alkyl groups having 6 to 25 carbon atoms. α and β may be the same or different and may be substituted or unsubstituted. represents an arylene group having 6 to 25 carbon atoms. 2 represents a halogen. 1 teeth, represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms. Also, R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon atom. It represents an aryl group having 6 to 25 prime numbers, a halogen group, or a haloalkyl group.

[0096] The anthracene derivative of the present invention has high luminous efficiency. The anthracene derivative of the present invention can be suitably used in a light-emitting device. Therefore, it is suitable for use in light-emitting devices that display images, such as full-color displays. The anthracene derivative of the present invention has hole transport properties and can be suitably used in such devices. Therefore, it can also be used as a hole transport layer of a light-emitting element.

[0097] (Embodiment 2) In this embodiment, the organic compound which is a raw material for synthesizing the anthracene derivative of the present invention is The organic compound is a novel substance and is therefore included in the present invention. .

[0098] The organic compound is an organic compound represented by general formula (8).

[0099] [ka]

[0100] In the above general formula (8), Ar 2 is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms β represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms; R 1 is carbon represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 4 carbon atoms. 25 represents an aryl group, a halogen group, or a haloalkyl group.

[0101] In the above general formula (8), Ar 2 Examples of the substituent represented by the formula (Ar2-1) include: Examples include the structures shown in (Ar2-19).

[0102] [ka]

[0103] In the general formula (8), the structure represented by β includes, for example, (β-1) to ( β-10) is an example of the structure shown.

[0104] [ka]

[0105] In addition, in the general formula (8), R 1 Examples of the substituent represented by (R1-1 ) to (R1-21).

[0106] [ka]

[0107] In addition, in the general formula (8), R 2Examples of the substituent represented by (R2-1 ) to (R2-24).

[0108] [ka]

[0109] Specific examples of such organic compounds of the present invention include the following (200) to (264) However, the present invention is not limited to these.

[0110] [ka]

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] As a method for synthesizing the organic compound of the present invention, various reactions can be applied. For example, Synthesized using the same synthesis method (synthetic scheme (a-2)) as compound 5 shown in embodiment 1. It is possible.

[0120] (Embodiment 3) In this embodiment mode, one mode of a light-emitting element using an anthracene derivative of the present invention will be described with reference to FIG. 1 will be used to explain the following.

[0121] The light-emitting element of the present invention has a plurality of layers between a pair of electrodes. In other words, the recombination of carriers at a location away from the electrodes is prevented. In order to achieve this, layers made of materials with high carrier injection properties and materials with high carrier transport properties are constructed. The materials are combined and layered.

[0122] In this embodiment, the light-emitting element includes a first electrode 101, a second electrode 103, and a first The layer 102 includes an organic compound and is disposed between the electrode 101 and the second electrode 103. In this embodiment, the first electrode 101 functions as an anode, and the second electrode 103 In other words, the first electrode 101 functions as a cathode. A voltage is applied to the first electrode 101 and the second electrode 103 so that the potential of the first electrode 101 is higher than that of the second electrode 103. The following description will be given on the assumption that light is emitted when voltage is applied.

[0123] The substrate 100 is used as a support for the light-emitting element. The substrate 100 may be made of, for example, glass, Alternatively, plastic or the like can be used. Anything other than these may be used as long as it functions as a body.

[0124] The first electrode 101 is preferably made of a material having a large work function (specifically, 4.0 eV or more). It is preferable to use metals, alloys, conductive compounds, and mixtures thereof. Specifically, for example, indium oxide-tin oxide (ITO) Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide Indium Zinc Oxide (IZO), Tungsten Oxide and Indium oxide containing zinc oxide (IWZO) and other conductive metals are also used. Oxide films are usually formed by sputtering, but they can also be produced by applying the sol-gel method. For example, indium oxide-zinc oxide (IZO) has a ratio of 1 to 1. Formed by sputtering using a target containing 20 wt% zinc oxide In addition, indium oxide containing tungsten oxide and zinc oxide (IWZO) is made by mixing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide. It can be formed by sputtering using a target containing 100% by weight of this compound. Others include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), and chromium (Cr ), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (P d) or nitrides of metal materials (for example, titanium nitride).

[0125] In addition, when a layer containing a composite material, which will be described later, is used as a layer in contact with the first electrode 101, As the first electrode 101, various metals, alloys, and electrically conductive materials can be used regardless of the magnitude of the work function. For example, aluminum (A 1), silver (Ag), and alloys containing aluminum (AlSi), etc. can also be used. , a material with a small work function, an element belonging to Group 1 or 2 of the periodic table, i.e., Alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) Alkaline earth metals such as calcium (Ca), strontium (Sr), and Alloys containing (MgAg, AlLi), europium (Eu), ytterbium (Yb), etc. Rare earth metals and alloys containing these can also be used. Films of metals and alloys containing these can be formed by vacuum deposition. Alloys containing alkali metals or alkaline earth metals can also be formed by sputtering. It is also possible to form a film using silver paste or the like by the inkjet method. be.

[0126] The layer 102 containing an organic compound is not particularly limited in terms of the stacked structure of layers, and any layer having a high electron transporting property is suitable. a substance with high hole transporting properties, a substance with high electron injecting properties, a substance with high hole injecting properties, A layer made of a material having a high electron and hole transporting property and a layer made of a material having a high electron and hole transporting property in this embodiment mode. For example, a hole injection layer, a hole transport layer, a light emitting layer, The light-emitting layer, the electron transport layer, the electron injection layer, etc. can be appropriately combined. In this embodiment, the layer 102 containing an organic compound is a hole injection layer that is stacked in this order on the first electrode 101. 111, a hole transport layer 112, a light emitting layer 113, and an electron transport layer 114. The materials constituting each layer are specifically shown below.

[0127] The hole injection layer 111 is a layer containing a substance with high hole injection properties. Umium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (abbreviated as CuP c) Phthalocyanine compounds such as 4,4'-bis[N-(4-diphenylaminophenyl) 4,4'-bis(N-{ 4-[N-(3-methylphenyl)-N-phenylamino]phenyl}-N-phenyla aromatic amine compounds such as poly(3,4-amino)biphenyl (abbreviation: DNTPD) or poly(3,4- Ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc. The hole injection layer 111 can also be formed from such polymers.

[0128] In addition, the hole-injecting layer 111 may be formed by adding an acceptor substance to a substance having a high hole-transporting property. A composite material having a high hole transporting property and an acceptor substance can be used. By using a material containing such a material, the material for forming the electrode can be selected regardless of the work function of the electrode. That is, the first electrode 101 can be made of not only a material with a large work function but also a material with a low work function. Materials with small functions can be used. -Tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F4-TCNQ ), chloranil, etc. Also included are transition metal oxides. Further examples include oxides of metals belonging to groups 4 to 8 of the periodic table. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, and molybdenum oxide Tungsten oxide, manganese oxide, and rhenium oxide are preferred because of their high electron-accepting properties. However, molybdenum oxide is particularly preferred because it is stable in the air, has low hygroscopicity, and is easy to handle. It's nice.

[0129] As a substance with high hole transporting properties used in the composite material, aromatic amine compounds and carbazoles are Derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. Various compounds can be used. So, 10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. However, other materials may be used as long as they have a higher hole transporting property than electron transporting property. Specific examples of organic compounds that can be used in the composite material are listed below.

[0130] For example, aromatic amine compounds that can be used in composite materials include N,N'-bis(N-methyl-N,N'-bis-N-phenyl-N-methyl-N-phenyl ... (4-methylphenyl)(p-tolyl)-N,N'-diphenyl-p-phenylenediamine DTDPPA, 4,4'-bis[N-(4-diphenylaminophenyl)- N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N '-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino )biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylamino phenyl)-N-phenylamino]benzene (abbreviation: DPA3B), etc. do.

[0131] Specific examples of carbazole derivatives that can be used in composite materials include 3-[N- (9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol 3,6-bis[N-(9-phenylcarbazole-3 -yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2) , 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino] -9-phenylcarbazole (abbreviation: PCzPCN1), etc.

[0132] In addition, carbazole derivatives that can be used in composite materials include 4,4'-di(N -carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tris[4-(N-carbazolyl)biphenyl] 9-[4-(10-phenyl-9-azolyl)phenyl]benzene (abbreviation: TCPB), thyl)phenyl]-9H-carbazole (abbreviation: CzPA), 1,4-bis[4-( N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene, etc. This can be done.

[0133] In addition, examples of aromatic hydrocarbons that can be used in the composite material include 2-tert -butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2- tert-Butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3, 5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl-9 ,10-bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,1 0-Di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene 2-tert-butylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAn th), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) , 9,10-bis[2-(1-naphthyl)phenyl]-2-tert-butylanthracene 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7- Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl 9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,1 0'-Diphenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl) 10,10'-bis[(2,3,4,5,6-pentafluorophenyl)-9,9'-bianthryl, (phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, etc. In addition, pentacene, coronene, etc. can also be used. -6 cm 2 / Vs or more and aromatic hydrocarbons with carbon numbers of 14 to 42 are used. It is more preferable that

[0134] The aromatic hydrocarbons that can be used in the composite material may have a vinyl skeleton. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2,2- Diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2- diphenylvinyl)phenyl]anthracene (abbreviation: DPVPA), and the like.

[0135] The hole injection layer 111 may be formed of a polymer compound (oligomer, dendrimer, polymer, etc.). For example, poly(N-vinylcarbazole) (abbreviation: PVK) ), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{ N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino} Poly[N,N'-bis(4-butylphenyl)methacrylamide] (abbreviation: PTPDMA) (phenyl)-N,N'-bis(phenyl)benzidine (abbreviation: Poly-TPD), etc. In addition, the polymer compounds poly(3,4-ethylenedioxythiophene) / poly Poly(styrene sulfonate) (PEDOT / PSS), polyaniline / poly(styrene sulfonate) A polymer compound to which an acid such as polyaniline sulfonate (PAni / PSS) has been added can be used.

[0136] In addition, the polymer compounds such as the above-mentioned PVK, PVTPA, PTPDMA, and Poly-TPD A composite material is formed using the above-mentioned acceptor material, and the composite material is used as the hole injection layer 111. It may be used.

[0137] The hole-transporting layer 112 is a layer containing a substance with a high hole-transporting property. For example, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl N,N'-bis(3-methylphenyl)-N,N'-diphenyl- [1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4',4''- Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4 ',4''-Tris[N-(3-methylphenyl)-N-phenylamino]triphenyl amine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene [N-2-yl]-N-phenylamino]-1,1'-biphenyl (abbreviation: BSPB), etc. The aromatic amine compounds mentioned here can be used. -6 cm 2 A material with a hole mobility of 1 / Vs or higher. However, a material with a higher hole transporting ability than an electron transporting ability. Any other substance may be used as long as it has a high hole transporting property. The material may be not only a single layer, but also a laminate of two or more layers made of the above-mentioned materials.

[0138] The hole transport layer 112 may be made of PVK, PVTPA, PTPDMA, or Poly-TP. Polymer compounds such as D can also be used.

[0139] The light-emitting layer 113 is a layer containing a substance with high light-emitting properties. The optical layer 113 contains the anthracene derivative of the present invention shown in the first embodiment. Helical derivatives exhibit high luminous efficiency and are therefore suitable for use in light-emitting elements as highly luminescent materials. You can be there.

[0140] The electron transport layer 114 is a layer containing a substance with high electron transport properties. Tris(4-methyl-8-quinolinolato) aluminum (abbreviation: Alq), tris(4-methyl-8-quinolinolato) Aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato) Beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenyl Alphenolato)aluminum (abbreviated as BAlq), etc. Metal complexes having a bis[2-(2-hydroxybenzoyl)methyl]propanol skeleton can also be used. bis[2-(2-(2-phenyl)benzoxazolato]zinc (abbreviation: Zn(BOX)2) -hydroxyphenyl)benzothiazolato]zinc (abbreviated as Zn(BTZ)2) Metal complexes having thiazole or thiazole ligands can also be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD) and 1,3-bis[5-(p-ter t-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: O XD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl) phenyl)-1,2,4-triazole (abbreviation: TAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviated as BCP), etc. can also be used. The solid material is mainly 10 -6 cm 2 It is a substance with an electron mobility of 1 / Vs or more. Any substance other than those mentioned above may be used as the electron transport layer as long as it has a higher electron transporting property than hole transporting property. The electron transport layer may be not only a single layer, but also two or more layers made of the above-mentioned materials. It may also be a laminate.

[0141] Furthermore, a polymer compound can be used as the electron transport layer 114. For example, poly[ (9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl) Poly[(9,9-dioctylfluorene-2,7-diyl)] (abbreviation: PF-Py) )-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be used.

[0142] In addition, an electron injection layer may be provided between the electron transport layer 114 and the second electrode 103. The injection layer is made of lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CsF), Use alkali metal compounds such as CaF2 or alkaline earth metal compounds. Furthermore, a compound having an electron transporting property and an alkali metal or an alkaline earth metal can be used. Combination layers can also be used, such as magnesium (Mg) in Alq. The electron injection layer may be formed by combining a substance having an electron transporting property with an alkali metal. The use of a layer of a combination of metals or alkaline earth metals reduces the amount of current from the second electrode 103. This is more preferable because the child injection occurs efficiently.

[0143] The material forming the second electrode 103 is selected from those having a small work function (specifically, 3.8 eV Metals, alloys, electrically conductive compounds, and mixtures thereof are preferred. Specific examples of such cathode materials include those of Group 1 or are elements belonging to Group 2, i.e., alkali metals such as lithium (Li) and cesium (Cs) and aluminum such as magnesium (Mg), calcium (Ca), and strontium (Sr). Potassium earth metals and alloys containing them (MgAg, AlLi), europium (Eu) and rare earth metals such as ytterbium (Yb) and alloys containing these. Films of potassium metals, alkaline earth metals, and alloys containing these can be formed using vacuum deposition. In addition, alloys containing alkali metals or alkaline earth metals can be deposited by sputtering. Alternatively, a silver paste or the like can be applied by an ink jet method or the like. It is also possible to form a film.

[0144] In addition, by providing an electron injection layer between the second electrode 103 and the electron transport layer 114, Regardless of the magnitude of the work function, Al, Ag, ITO, silicon or silicon oxide containing oxide Various conductive materials can be used for the second electrode 103, such as indium tin oxide. These conductive materials are deposited using methods such as sputtering, inkjet printing, and spin coating. It is possible to form a film using this method.

[0145] The light-emitting element having the above-described structure shown in this embodiment mode has a first electrode 101 and a second electrode 102. By applying a voltage between the electrode 103 and the highly luminescent material, a current flows. Holes and electrons recombine in the light-emitting layer 113, which is a layer containing That is, a light emitting region is formed in the light emitting layer 113 .

[0146] The light is emitted through either the first electrode 101 or the second electrode 103, or both. Therefore, either the first electrode 101 or the second electrode 103 Alternatively, both electrodes may be light-transmitting electrodes. Only the first electrode 101 may be light-transmitting electrodes. When the second electrode 101 is When only the electrode 103 has light-transmitting properties, light passes through the second electrode 103 and exits to the opposite side of the substrate. The first electrode 101 and the second electrode 103 are both light-transmitting. In the case of the electrodes, light passes through the first electrode 101 and the second electrode 103 and reaches the substrate side and It is taken out from both the substrate side and the opposite side.

[0147] In FIG. 1, the first electrode 101 functioning as an anode is provided on the substrate 100 side. However, the second electrode 103 functioning as a cathode may be provided on the substrate 100 side.

[0148] The layer 102 containing an organic compound can be formed by various methods, regardless of whether it is a dry method or a wet method. Alternatively, each electrode or each layer may be formed using a different film formation method. Dry methods include vacuum deposition and sputtering. The wet method includes an ink jet method and a spin coating method.

[0149] The electrodes may also be formed by a wet method using a sol-gel method, or by using a paste of a metal material. Alternatively, a dry method such as a sputtering method or a vacuum deposition method may be used. It may be formed by using.

[0150] A specific method for forming a light-emitting element will be described below. When the layers are coated separately, the light-emitting layer is preferably formed by a wet method. By forming it using a wet method such as the ink jet method, it is possible to coat the light-emitting layer even on a large substrate. This makes it easier to separate the workpieces, improving productivity.

[0151] For example, in the structure shown in this embodiment, the first electrode is formed by sputtering, which is a dry method. The hole injection layer is formed by a wet method such as an inkjet method or a spin coating method, and the hole transport layer is formed by a dry method. the light-emitting layer is formed by a wet method, the inkjet method, and the electron injection layer is formed by a dry method. The first electrode is formed by co-evaporation, and the second electrode is formed by a wet method such as inkjet or spin coating. The first electrode may be formed by an inkjet method, which is a wet method, and the hole injection layer may be formed by a dry method. the hole transport layer is formed by a wet method such as an inkjet method or spin coating; The inkjet method is a wet method, and the electron injection layer is formed by the inkjet method or the spin coater method. The first electrode is formed by a wet method such as an inkjet method or a spin coating method. The method is not limited to the above, and a wet method and a dry method may be combined as appropriate.

[0152] In addition, for example, the first electrode is formed by a dry method such as sputtering, and the hole injection layer and the hole transport layer are formed by a dry method such as sputtering. The layer is formed by a wet method such as inkjet or spin coating, and the light-emitting layer is formed by a wet method such as inkjet. The electron injection layer was formed by a dry method, vacuum deposition, and the second electrode was formed by a dry method, vacuum deposition. That is, a positive electrode can be formed on a substrate on which a first electrode is formed in a desired shape. The hole injection layer to the light-emitting layer are formed by a wet method, and the electron injection layer to the second electrode are formed by a dry method. In this method, the layers from the hole injection layer to the light emitting layer can be formed at atmospheric pressure. The electron injection layer to the second electrode can be formed in a vacuum. This allows for the process to be simplified and productivity to be improved. do.

[0153] The light-emitting element of the present invention having the above-described structure has a first electrode 101, a second electrode 103, and a The potential difference between them causes a current to flow, and the light-emitting layer 113, which is a layer containing a highly luminescent substance, In other words, the light-emitting layer 113 has a light-emitting region. It is structured in such a way that it can be formed.

[0154] The structure of the layer provided between the first electrode 101 and the second electrode 103 is the same as that described above. The thickness is not limited to 100 nm. Light emission occurs when holes and electrons recombine at a location away from the first electrode 101 and the second electrode 103. Any configuration other than the above may be used as long as it provides regions.

[0155] Since the anthracene derivative of the present invention has high luminous efficiency, it is possible to It can be used as a light-emitting layer without containing a light-emitting substance. Since anthracene derivatives have high luminous efficiency, light-emitting elements with high luminous efficiency can be obtained. .

[0156] The anthracene derivative of the present invention emits blue light with high color purity, and therefore, A light-emitting element that emits light can be obtained.

[0157] In addition, the anthracene derivative of the present invention efficiently emits blue light with high color purity. Thus, a light-emitting element that emits blue light with high luminous efficiency can be obtained.

[0158] Furthermore, by using the anthracene derivative of the present invention, a light-emitting element having a long life can be obtained. can be done.

[0159] Furthermore, the light-emitting element using the anthracene derivative of the present invention is capable of emitting blue light with high efficiency. Therefore, it can be suitably used for full color displays. Furthermore, it emits blue light with a long life. Therefore, it can be suitably used for full color displays. Compared to green and red light-emitting elements, development of these elements is lagging behind in terms of lifespan and efficiency. Therefore, a blue light-emitting device having such characteristics is desired. The device is capable of emitting blue light with high efficiency and long life, making it suitable for full-color displays. .

[0160] (Fourth embodiment) In this embodiment mode, a light-emitting element having a different structure from that shown in Embodiment Mode 3 will be described. .

[0161] The light-emitting layer 113 shown in Embodiment Mode 3 is formed by dispersing the anthracene derivative of the present invention in another substance. By adopting this structure, light emission from the anthracene derivative of the present invention can be obtained. Since the anthracene derivative of the present invention emits blue light, a light-emitting element that emits blue light can be obtained. It is possible.

[0162] Here, various materials can be used as the substance for dispersing the anthracene derivative of the present invention. In addition to the substances with high hole transporting properties and the substances with high electron transporting properties described in Embodiment 2, 4'-bis(N-carbazolyl)biphenyl (abbreviation: CBP) and 2,2',2"-(1 ,3,5-benzenetriyl)tris[1-phenyl-1H-benzimidazole](abbreviation TPBI), 9,10-di(2-naphthyl)anthracene (DNA), 2-t ert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA) , 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation Also, a substance that disperses the anthracene derivative of the present invention may be used. Polymer materials can be used as the material. For example, poly(N-vinylcarbazole) (abbreviated Poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N -(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenyl amino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis (4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly- TPD), and poly[(9,9-dihexylfluorene-2,7-diyl)-co-( pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluor) oren-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)](abbreviation (designated PF-BPy) can be used.

[0163] The anthracene derivative of the present invention has high luminous efficiency, and therefore, when used in a light-emitting element, A highly efficient light-emitting element can be obtained.

[0164] Furthermore, the anthracene derivative of the present invention emits blue light with high color purity, and therefore, A light-emitting element that emits bright blue light can be obtained.

[0165] Furthermore, the anthracene derivative of the present invention emits light efficiently, and therefore, blue light emission with high luminous efficiency is possible. A light emitting element that can emit light can be obtained.

[0166] Furthermore, by using the anthracene derivative of the present invention, a light-emitting element having a long life can be obtained. can be done.

[0167] Furthermore, the light-emitting element using the anthracene derivative of the present invention emits blue light with high efficiency and color purity. Since it is capable of emitting light, it can be suitably used in full-color displays. Since the compound is capable of emitting blue light, it can be suitably used in full-color displays.

[0168] Note that the structures described in Embodiment 3 can be used as appropriate for the structures other than the light-emitting layer 113.

[0169] (Embodiment 5) In this embodiment, a light emitting device having a different configuration from those shown in the third and fourth embodiments is described. The element will be described.

[0170] The light-emitting layer 113 shown in Embodiment Mode 3 is formed by adding a light-emitting substance to the anthracene derivative of the present invention. By using a dispersed structure, light can be emitted from the light-emitting substance.

[0171] When the anthracene derivative of the present invention is used as a material for dispersing other luminescent substances, In addition, the anthracene derivative of the present invention can be used to obtain a luminescent color due to the luminescent material. The emission color due to the luminescent material dispersed in the anthracene derivative is different from the emission color due to the luminescent material dispersed in the anthracene derivative. It is also possible to obtain mixed luminescent colors.

[0172] Here, various materials can be used as the luminescent substance dispersed in the anthracene derivative of the present invention. Specifically, N,N'-diphenylquinacridone (abbreviation: DPQd) , Coumarin 6, Coumarin 545T, 4-(dicyanomethylene)-2-methyl-6-(p- Dimethylaminostyryl)-4H-pyran (abbreviation: DCM1), 4-(dicyanomethylene )-2-methyl-6-(julolidin-4-yl-vinyl)-4H-pyran (abbreviation: DC M2), N,N'-dimethylquinacridone (abbreviation: DMQd), {2-(1,1-dimethyl ethyl)-6-[2-(2,3,6,7-tetrahydro-1,1,7,7-tetramethyl 1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pyran-4 -ylidene}propanedinitrile (abbreviation: DCJTB), 5,12-diphenyltetradecane DPT, 4-(9H-carbazol-9-yl)-4'-(10-phenyl -9-anthryl)triphenylamine (abbreviation: YGAPA), 4,4'-(2-tert-butyl) t-butylanthracene-9,10-diyl)bis{N-[4-(9H-carbazole- 9-yl)phenyl]-N-phenylaniline} (abbreviation: YGABPA), N,9-diphenyl Phenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo N,N'-(2-tert-butylanthracene) -9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl-1 ,4-Phenylenediamine (abbreviation: DPABPA), N,N'-bis[4-(9H-cal (bazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine N-[4-(9H-carbazol-9-yl)phenyl]-N -phenylstilben-4-amine (abbreviation: YGAS), N,N'-diphenyl-N,N '-Bis(9-phenylcarbazol-3-yl)stilbene-4,4'-diamine (abbreviation PCA2S), 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP ), perylene, rubrene, 1,3,6,8-tetraphenylpyrene, etc. Fluorescent materials can be used. [Fd(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fd pq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-2 Phosphorescent phosphors such as 1H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Photoluminescent materials can be used.

[0173] Note that the structures described in Embodiment 3 can be used as appropriate for the structures other than the light-emitting layer 113.

[0174] (Embodiment 6) In this embodiment, a light-emitting element having a different configuration from those shown in Embodiments 3 to 5 is This will be explained using FIG. 2.

[0175] The light-emitting element described in this embodiment has a structure similar to that of the light-emitting layer 113 in the light-emitting element described in Embodiment 3. A first layer 121 and a second layer 122 are provided.

[0176] The light-emitting layer 113 is a layer containing a highly light-emitting substance. 113 has a first layer 121 and a second layer 122. The first layer 121 is a first organic The second layer 122 comprises a second organic compound and an electron transporting organic compound. The first layer 121 has a conductive organic compound. It is provided in contact with the anode side.

[0177] The first organic compound and the second organic compound are highly luminescent substances. The light-emitting element shown in the figure is a light-emitting element containing the first organic compound or the second organic compound. The anthracene derivative of the present invention includes a blue light emitting compound having high color purity. Therefore, it can be suitably used as a highly luminescent substance in the light-emitting element described in this embodiment mode. The first organic compound and the second organic compound may be the same or different.

[0178] The anthracene derivative of the present invention is used as either the first organic compound or the second organic compound. In this case, for example, 4-(9H-carbazol-9-yl)-4'-(10-furan) 4,4'-(2-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), tert-butylanthracene-9,10-diyl)bis{N-[4-(9H-carbazo N,9-(4-amino-9-yl)phenyl]-N-phenylaniline} (abbreviation: YGABPA), -diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-chlor PCAPA, N,N'-(2-tert-butylamine) thracene-9,10-diyldi-4,1-phenylene)bis[N,N',N'-triphenyl N,N'-bis[4-( 9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4 '-diamine (abbreviation: YGA2S), N-[4-(9H-carbazol-9-yl)phenyl] N,N'-diphenyl]-N-phenylstilben-4-amine (abbreviation: YGAS), N,N'-bis(9-phenylcarbazol-3-yl)stilbene-4,4'-di Amine (abbreviation: PCA2S), 4,4'-bis(2,2-diphenylvinyl)biphenyl (abbreviation: DPVBi), 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: Blue pigments such as tetraphenylpyrene (TBP), perylene, rubrene, and 1,3,6,8-tetraphenylpyrene These substances can be used as the anthracene derivatives of the present invention. Since it emits light of a similar color to that of the compound semiconductor, it can be suitably used for the light-emitting element of this embodiment.

[0179] In addition, the organic compound with hole transporting properties contained in the first layer 121 has a hole transporting property rather than an electron transporting property. The organic compound contained in the second layer 122 has an electron-transporting property. It is a substance that has a higher electron transporting property than a hole transporting property.

[0180] The principle of the light-emitting device of the present invention having the above-mentioned configuration will be explained below with reference to FIG.

[0181] In FIG. 2, holes injected from the first electrode 101 are injected into the first layer 121 . The holes injected into the first layer 121 are transported to the first layer 121, but are also transported to the second layer 122. The electron-transporting organic compound contained in the second layer 122 is also injected into the hole transport layer 22. Since the second layer 122 has a higher electron transporting property than a transporting property, the holes injected into the second layer 122 As a result, holes tend to be concentrated near the interface between the first layer 121 and the second layer 122. In addition, holes reach the electron transport layer 114 without recombining with electrons. This suppresses the phenomenon of

[0182] On the other hand, electrons injected from the second electrode 103 are injected into the second layer 122. The electrons injected into the second layer 122 are transported to the second layer 122, but also to the first layer 121. Here, the organic compound with hole transporting properties contained in the first layer 121 is an organic compound with electron transporting properties. Since the first layer 121 has a higher hole transporting property than the second layer 122, the electrons injected into the first layer 121 move. As a result, many electrons exist near the interface between the first layer 121 and the second layer 122. In addition, electrons may reach the hole transport layer 112 without recombining with holes. The phenomenon of sagging is suppressed.

[0183] From the above, it is believed that there are many holes and electrons in the region near the interface between the first layer 121 and the second layer 122. The probability of recombination near the interface increases. A light-emitting region is formed near the center of 113. As a result, electrons can be generated without recombining holes. The electrons may reach the electron transport layer 114 or may not recombine and may reach the hole transport layer 11 2, it is possible to prevent a decrease in the probability of recombination. This prevents deterioration of the carrier balance over time, leading to improved reliability.

[0184] In order to inject holes and electrons into the first layer 121, a hole-transporting organic compound is used. The compound is an organic compound capable of oxidation and reduction reactions, and has the highest occupied molecular orbital (HOMO) level. The potential level is preferably -6.0 eV or more and -5.0 eV or less. The lowest unoccupied molecular orbital (LUMO) level of organic compounds is between -3.0 eV and -2.0 eV. It is preferable that there is.

[0185] Organic compounds capable of such oxidation and reduction reactions include polycyclic compounds with 3 to 6 rings. Among the anthracene derivatives, anthracene derivatives are particularly suitable. Specifically, the hole-transporting organic compound is 9,10-diphenylanthracene. (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10-phenyl-9-anthracene] tolyl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-( 10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9- Diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carba PCAPA, N,9-diphenyl-N-{4-[4-(1 0-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine Examples include PCAPBA (abbreviated as PCAPBA).

[0186] Similarly, in order for holes and electrons to be injected into the second layer 122, an electron transporting The organic compound is capable of oxidation and reduction reactions, and its HOMO level is -6 It is preferable that the value is between -0.0 eV and -5.0 eV.

[0187] Organic compounds capable of such oxidation and reduction reactions include polycyclic compounds with 3 to 6 rings. Examples of the arylacene derivatives include anthracene derivatives, phenanthrene derivatives, Examples include pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives. For example, an electron transporting compound that can be used in the second layer is 9-[4-(10- Phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3, 6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-ca DPCzPA (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)a anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: D NA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t -BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene -3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene- 4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(ben phen-1,3,5-triyl)tripylene (abbreviation: TPB3), etc.

[0188] As described above with reference to FIG. 2, in the light-emitting device of the present invention, In order to configure the device so that holes are injected from the first layer 121 to the second layer 122, a hole-transporting organic compound is used. The difference between the HOMO level of the material and the HOMO level of the electron-transporting organic compound is preferably small. In addition, in order to configure the element so that electrons are injected from the second layer 122 to the first layer 121, Therefore, the LUMO levels of hole-transporting organic compounds and electron-transporting organic compounds are The difference between the HOMO level of the hole-transporting organic compound and the HOMO level of the electron-transporting organic compound is preferably small. If the difference with the HOMO level of the compound is large, the light-emitting region will be located in either the first layer or the second layer. Similarly, the LUMO level of hole-transporting organic compounds and electron-transporting organic compounds Even if the difference between the LUMO levels of the compound is large, the light-emitting region is either the first layer or the second layer. Therefore, the HOMO level of the hole-transporting organic compound and the HOMO level of the electron-transporting organic compound are biased to one side. The difference from the HOMO level of the organic compound is preferably 0.3 eV or less. It is desirable that the LUMO of the hole-transporting organic compound is 0.1 eV or less. The difference between the electron transport level and the LUMO level of the electron transporting organic compound is preferably 0.3 eV or less. It is more preferable that the potential is 0.1 eV or less.

[0189] In addition, since the light emitting element emits light by recombining electrons and holes, the light emitting layer 113 The organic compound used is preferably stable even after repeated oxidation and reduction reactions. That is, it is preferable that the oxidation reaction and the reduction reaction are reversible. Hole-transporting organic compounds and electron-transporting organic compounds undergo repeated oxidation and reduction reactions. It is preferable that the compound is stable even after repeated oxidation and reduction reactions. This can be confirmed by cyclic voltammetry (CV) measurements. .

[0190] Specifically, the oxidation peak potential (E pa) value and reduction peak of the reduction reaction Peak potential (E pc ) and changes in peak shape, etc., are measured to determine the oxidation reaction It can be confirmed whether the light-emitting layer 113 is stable even after repeated reduction reactions. The hole-transporting organic compound and the electron-transporting organic compound used in the present invention have a high oxidation peak potential. It is preferred that the change in the degree and intensity of the reduction peak potential is less than 50%. It is preferable that the oxidation peak is reduced by 5% or less. It is preferable that the peak intensity is maintained at 70% or more. It is preferable that the strength of the peak potential of the oxidation and reduction is maintained. The change in value is preferably 0.05 V or less, and more preferably 0.02 V or less. It is preferable that there is.

[0191] In addition, when the first layer and the second layer contain different highly luminescent substances, either one of them can be used. However, the first organic compound in the first layer and the second organic compound in the second layer may emit light. By using the same material as the second organic compound contained in the first layer, light is emitted near the center of the light-emitting layer. Therefore, the highly luminescent material contained in the first layer and the highly luminescent material contained in the second layer can be It is preferable that the highly luminescent substance contained therein is the anthracene derivative of the present invention. Since the light-emitting anthracene derivative has high luminous efficiency, it can be applied to the structure shown in this embodiment mode. This makes it possible to obtain a light-emitting element with high luminous efficiency and a long life.

[0192] The light-emitting element shown in this embodiment has a structure in which a light-emitting layer is electrically connected to an interface between a light-emitting layer and a hole-transporting layer or between a light-emitting layer and an electron-transporting layer. The light-emitting region is not formed at the interface with the light-emitting layer, but near the center of the light-emitting layer. Therefore, the influence of deterioration due to the proximity of the light-emitting region to the hole transport layer or electron transport layer is small. Therefore, a light emitting element with little deterioration and a long life can be obtained. Furthermore, the light-emitting layer of the light-emitting device of the present invention is stable even after repeated oxidation and reduction reactions. Because it is made of a compound, it is resistant to deterioration even when light is repeatedly emitted by the recombination of holes and electrons. Therefore, a light-emitting element with a longer life can be obtained.

[0193] In addition, the light-emitting element shown in this embodiment mode has a different emission color from the first organic compound and the second organic compound. Since the emission colors are similar, not only the first organic compound but also the second organic compound Even when light is emitted, light with high color purity can be obtained. is a substance that has high light emitting properties and emits blue light. This is particularly effective for light emitting elements of the blue-green and blue-green series. This is a necessary color when manufacturing a display, and the application of this invention improves deterioration. Of course, it may be used for green or red light emitting elements. It is also possible to combine it with the above embodiment as appropriate.

[0194] (Embodiment 7) The present embodiment relates to a light emitting device (hereinafter referred to as a stack) having a structure in which a plurality of light emitting units according to the present invention are stacked. The embodiment of the light-emitting device (hereinafter referred to as a layer type device) will be described with reference to FIG. The light-emitting device is a stacked type light-emitting device having a plurality of light-emitting units between the first electrode and the second electrode. The layer 102 may have the same structure as that of the layer 102 containing an organic compound described in Embodiment Mode 2. That is, the light-emitting element described in Embodiment 2 is a light-emitting element having one light-emitting unit. In this embodiment, a light emitting element having a plurality of light emitting units will be described. do.

[0195] In FIG. 3, a first light-emitting unit 501 is disposed between a first electrode 501 and a second electrode 502. The first light-emitting unit 511 and the second light-emitting unit 512 are stacked. A charge generating layer 513 is provided between the first electrode 501 and the light emitting unit 512. The second electrode 502 can be the same as that in the second embodiment. The unit 511 and the second light-emitting unit 512 may have the same configuration or different configurations. Preferably, the structure is the same as that of the layer containing the organic compound described in the second to sixth embodiments. can be applied.

[0196] The charge generating layer 513 contains a composite material of an organic compound and a metal oxide. The composite material of the alloy and the metal oxide is the composite material shown in the second embodiment or the fifth embodiment. It is made up of organic compounds and metal oxides such as vanadium oxide, molybdenum oxide, and tungsten oxide. The organic compounds include aromatic amine compounds, carbazole derivatives, aromatic carbons, etc. Various compounds such as hydrogen hydride, polymer compounds (oligomers, dendrimers, polymers, etc.) As the organic compound, a hole transporting organic compound can be used. Degrees 10 -6 cm 2 It is preferable to apply a value of / Vs or more. Other materials may be used as long as they have a high hole transporting property. Oxide composite materials have excellent carrier injection and transport properties, making them suitable for low-voltage operation and A low current drive can be achieved.

[0197] The charge generating layer 513 is made of a composite material of an organic compound and a metal oxide, and other materials. For example, a layer containing a composite material of an organic compound and a metal oxide and a layer containing an electron donor may be formed. a layer containing a compound having high electron transport properties and a compound having high electron transport properties; Alternatively, a layer containing a composite material of an organic compound and a metal oxide and a transparent conductive film may be formed. may be formed by combining the above.

[0198] In any case, the charge between the first light-emitting unit 511 and the second light-emitting unit 512 When a voltage is applied between the first electrode 501 and the second electrode 502, the generating layer 513 generates a If electrons are injected into the light-emitting unit on one side and holes are injected into the light-emitting unit on the other side, For example, in FIG. 3, the potential of the first electrode is higher than the potential of the second electrode. When a voltage is applied so that the charge generation layer 513 generates electrons, the charge generation layer 513 generates electrons in the first light-emitting unit 511. The electron injection hole 514 may be injected into the second light-emitting unit 512.

[0199] In this embodiment, the light emitting element having two light emitting units has been described, but the light emitting element having three or more light emitting units may be used. The same can be applied to a light-emitting element in which the above light-emitting units are stacked. As in the light-emitting device according to the embodiment, a plurality of light-emitting units are disposed between a pair of electrodes by a charge generating layer. By separating the layers, it is possible to emit light in a high-brightness region while keeping the current density low. Therefore, a long-life element can be realized. In addition, when applied to lighting, the resistance of the electrode material This reduces the voltage drop due to the low voltage driving, making it possible to emit light uniformly over a large area. Therefore, a light emitting device that can emit light and consumes less power can be realized.

[0200] In addition, by making the light-emitting color of each light-emitting unit different, the light-emitting element as a whole For example, a light-emitting element having two light-emitting units can be used. In this case, the luminous color of the first luminous unit and the luminous color of the second luminous unit are in a complementary color relationship. By doing so, it is possible to obtain a light emitting element that emits white light as a whole. In addition, complementary colors are colors that become achromatic when mixed. By mixing light from materials that emit light of certain colors, white light can be obtained. The same applies to a light-emitting element having three light-emitting units. For example, the first light-emitting unit The light emitting color of the first light emitting unit is red, the light emitting color of the second light emitting unit is green, and the light emitting color of the third light emitting unit is red. When the emitted light color of the dot is blue, the light emitting element as a whole can emit white light.

[0201] Note that this embodiment mode can be combined with other embodiment modes as appropriate.

[0202] (Embodiment 8) In this embodiment, a light-emitting device manufactured using an anthracene derivative of the present invention will be described. explain.

[0203] In this embodiment, a light-emitting device manufactured using an anthracene derivative of the present invention will be described. The description will be made with reference to FIG. 4. Note that FIG. 4(A) is a top view showing a light-emitting device, and FIG. 4(B) is a top view showing a light-emitting device. (A) is a cross-sectional view taken along lines AA' and BB'. The light emission is controlled by a driving circuit unit (source side driving circuit) 401 shown by the dotted line. It includes an element part 402 and a driving circuit part (gate side driving circuit) 403. Also, 404 is a sealing The substrate 405 is a sealing material, and the inside surrounded by the sealing material 405 is a space 407. There are.

[0204] The lead wiring 408 is connected to the source side driver circuit 401 and the gate side driver circuit 403. The wiring is for transmitting the input signal, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal from Lint Circuit 409 Although only the FPC is shown here, this FPC has a printed circuit board. A printed wiring board (PWB) may be attached. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0205] Next, the cross-sectional structure will be described with reference to FIG. A source side driver circuit 401, which is a driver circuit section, is formed in this example. , one pixel in the pixel section 402 is shown.

[0206] The source side driver circuit 401 includes an n-channel TFT 423 and a p-channel TFT 42 4 is combined to form a CMOS circuit. In addition, the drive circuit is a CMOS circuit In this embodiment, the pixel may be formed of a PMOS circuit or an NMOS circuit. This refers to a driver-integrated type in which a drive circuit is formed on a substrate on which a part is formed, but this is not necessarily required. Alternatively, the driver circuit may be formed outside the substrate on which the pixel portion is formed, rather than on the substrate on which the pixel portion is formed.

[0207] The pixel section 402 includes a switching TFT 411, a current control TFT 412, and The pixel is formed by a plurality of pixels including a first electrode 413 electrically connected to the drain. An insulator 414 is formed to cover the end of the first electrode 413. It is formed by using a photosensitive acrylic resin film of a mold.

[0208] In order to improve the covering property, the upper end or the lower end of the insulator 414 is provided with a curvature. For example, the material of the insulator 414 is a positive photosensitive adhesive. When using krill, the insulator 414 has a radius of curvature (0.2 μm to 3 μm) only at the top end. It is preferable that the insulator 414 has a curved surface that changes its shape when irradiated with light. Negative type that becomes insoluble in etchant, or becomes soluble in etchant upon exposure to light Any positive type may be used.

[0209] On the first electrode 413, a layer 416 containing an organic compound and a second electrode 417 are formed. Here, the material used for the first electrode 413 that functions as an anode is For example, it is desirable to use a material with a large work function. Indium tin oxide film containing 2 to 20 wt% zinc oxide, nitride In addition to single layer films such as titanium film, chromium film, tungsten film, Zn film, and Pt film, titanium nitride film and Lamination with a film mainly composed of aluminum, titanium nitride film and a film mainly composed of aluminum A laminated film such as a three-layer structure of a titanium nitride film and a titanium oxide film can be used. It has low resistance as a wiring, good ohmic contact, and also functions as an anode. It can be done.

[0210] The layer 416 containing an organic compound can be formed by a deposition method using a deposition mask, an ink-jet method, The layer 416 containing an organic compound is formed by various methods such as spin coating. The anthracene derivative of the present invention shown in Form 1 is included. Other materials that make up 416 include low molecular weight compounds or high molecular weight compounds (oligomers, The organic compound-containing layer may be made of a material such as a dendrimer. In addition to organic compounds, inorganic compounds may also be used.

[0211] Furthermore, a second electrode 41 is formed on the layer 416 containing an organic compound and functions as a cathode. The material used for 7 is a material with a small work function (Al, Mg, Li, Ca, or any of these). alloys and compounds such as Mg-Ag, Mg-In, Al-Li, LiF, CaF2, etc. It is preferable that light generated in the layer 416 containing an organic compound is transmitted through the second electrode 417. In the case of passing the light through the second electrode 417, a metal thin film and a transparent conductive film (ITO, 2 to 2 Indium oxide containing 0 wt% zinc oxide, indium oxide containing silicon or silicon oxide It is preferable to use a laminate of aluminum-tin oxide, zinc oxide (ZnO, etc.).

[0212] Furthermore, by bonding the sealing substrate 404 to the element substrate 410 with a sealing material 405, A space 407 surrounded by the element substrate 410, the sealing substrate 404, and the sealant 405 contains a light-emitting element. The space 407 is filled with a filler. In addition to being filled with an inert gas (nitrogen, argon, etc.), it is also possible to fill it with a sealing material 405. In some cases, this may be the case.

[0213] It is preferable to use an epoxy resin for the sealing material 405. It is desirable that the sealing substrate 404 be made of a material that is as impermeable to moisture and oxygen as possible. Materials used for this include glass substrates, quartz substrates, and FRP (Fiberglass-Reinforced Plastics). Enforced Plastics), PVF (Polyvinyl Fluoride), Polyester Alternatively, a plastic substrate made of acrylic or the like can be used.

[0214] As described above, a light-emitting device manufactured using the anthracene derivative of the present invention can be obtained. This can be done.

[0215] The light-emitting device of the present invention uses the anthracene derivative described in Embodiment Mode 1, and therefore, A light emitting device having excellent characteristics can be obtained. Specifically, a light emitting device having a long life can be obtained. It is possible.

[0216] In addition, the light-emitting element using the anthracene derivative of the present invention has high luminous efficiency and therefore low consumption. A high power light emitting device can be obtained.

[0217] Furthermore, the light-emitting element using the anthracene derivative of the present invention can emit blue light with high efficiency and color purity. It can be used for full color displays because it can emit light. Since the blue light emission is long-lasting and has low conductivity, it can be suitably used for full-color displays. This can be done.

[0218] As described above, in this embodiment, an arrangement in which driving of a light emitting element is controlled by a transistor is Although the active matrix type light emitting device has been described above, there are also passive matrix type light emitting devices. FIG. 5 shows a passive matrix type light emitting device manufactured by applying the present invention. 5(A) is a perspective view showing the light emitting device, and FIG. 5(B) is a perspective view showing FIG. 5(A). 5 is a cross-sectional view taken along the line XY. In FIG. 5, an electrode 952 and an electrode 953 are provided on a substrate 951. Between the electrode 952 and the insulating layer 956, a layer 955 containing an organic compound is provided. The insulating layer 953 is covered with a partition wall layer 954. The sidewalls of the wall layer 954 have a narrower distance between one sidewall and the other sidewall as they approach the substrate surface. In other words, the cross section of the partition layer 954 in the short side direction is trapezoidal. The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) is larger than the upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not contact the insulating layer 953). In this way, by providing the partition layer 954, defects of the light emitting element due to static electricity or the like can be prevented. A passive matrix light emitting device containing the light emitting element of the present invention can also be used. By using the above-mentioned method, a light emitting device with a long life can be obtained. can be obtained.

[0219] (Embodiment 9) In this embodiment mode, an electronic device of the present invention including the light-emitting device shown in Embodiment 8 as a part thereof will be described. The electronic device of the present invention includes the anthracene derivative described in Embodiment 1. The display has a long life and consumes less power.

[0220] As an electronic device having a light-emitting element manufactured using the anthracene derivative of the present invention, cameras, goggle-type displays, navigation systems, etc. systems, sound reproduction devices (car audio, audio components, etc.), computers, game consoles devices, personal digital assistants (mobile computers, mobile phones, portable game consoles, e-books, etc.) ), image reproducing devices equipped with recording media (specifically, Digital Versatile A device equipped with a display device that can play back recording media such as discs (DVDs) and display the images. ) and other electronic devices. Specific examples of these electronic devices are shown in Figure 6.

[0221] FIG. 6A shows a television device according to the present invention, which includes a housing 9101, a support base 9102, a display unit 9103, a speaker part 9104, a video input terminal 9105, etc. In the display unit 9103, the light emitting element is the same as that described in the second to seventh embodiments. The light-emitting element has high luminous efficiency and a long life. The display portion 9103 that is made up of the light-emitting elements has the same characteristics. This TV set has less degradation in picture quality and consumes less power. These features allow TV equipment to significantly reduce the number of deterioration compensation circuits and power supply circuits. Since it can be reduced in size, the housing 9101 and the support 9102 can be made smaller and lighter. The television device according to the present invention is capable of achieving low power consumption, high image quality, and small size and light weight. This allows us to provide products that are suited to the living environment. The light-emitting element using the anthracene derivative shown in Form 1 can emit blue light with high color purity. Therefore, it is possible to obtain a television device capable of full color display and having a display unit with a long life. can be done.

[0222] FIG. 6B shows a computer according to the present invention, which includes a main body 9201, a housing 9202, a display unit 9203, keyboard 9204, external connection port 9205, pointing device 92 In this computer, the display unit 9203 includes the display unit 9206 and the like. The light emitting element is configured by arranging light emitting elements similar to those explained in Embodiment 7 in a matrix. Optical elements are characterized by high light-emitting efficiency and long life. The display unit 9203 also has similar features, so this computer has little degradation in image quality. These features allow for low power consumption in computers. The compensation function circuit and power supply circuit can be significantly reduced or downsized, so the main body 920 The computer according to the present invention can be made smaller and lighter in size and weight than the computer 1 and the housing 9202. Low power consumption, high image quality, and compact, lightweight design make this an environmentally friendly product. In addition, the light-emitting element using the anthracene derivative described in Embodiment 1 can emit light with a color. High-purity blue light emission is possible, allowing full-color display and providing a long-life display. You can get a computer that does this.

[0223] FIG. 6C shows a mobile phone according to the present invention, which includes a main body 9401, a housing 9402, a display unit 94 03, audio input unit 9404, audio output unit 9405, operation keys 9406, external connection port 9 407, an antenna 9408, etc. In this mobile phone, the display portion 9403 is The light emitting element is configured by arranging light emitting elements similar to those described in the second to seventh embodiments in a matrix. The light-emitting element is characterized by high luminous efficiency and long life. The display portion 9403 which is formed of light-emitting elements has similar characteristics. These features make it ideal for mobile phones. This allows the deterioration compensation circuit and power supply circuit to be significantly reduced or downsized. It is possible to reduce the size and weight of the body 9401 and the housing 9402. The mobile phone according to the present invention It offers low power consumption, high image quality, and is small and lightweight, making it ideal for portability. In addition, the light-emitting element using the anthracene derivative described in Embodiment 1 can be It is possible to emit blue light with high color purity, making it possible to display full color and providing a long-life display. You can get a mobile phone with

[0224] FIG. 6D shows a camera according to the present invention, which includes a main body 9501, a display unit 9502, and a housing 950 3, external connection port 9504, remote control receiver 9505, image receiver 9506, battery 9 507, a voice input unit 9508, operation keys 9509, an eyepiece 9510, etc. In the display unit 9502, the light emitting device is the same as that described in the second to seventh embodiments. The light-emitting element is configured by arranging elements in a matrix. The light-emitting element has high luminous efficiency and a long life. The display portion 9502 that is made up of the light-emitting elements has the same characteristic. This camera has the advantage of being able to reduce the deterioration of image quality and consume less power. These features allow the camera to significantly reduce the number of deterioration compensation circuits and power supply circuits, Since the size can be reduced, the main body 9501 can be made smaller and lighter. The camera according to the present invention is suitable for portability because it has low power consumption, high image quality, and is small and lightweight. In addition, it is possible to provide a product using the anthracene derivative shown in Embodiment 1. The light-emitting element is capable of emitting blue light with high color purity, making full-color display possible and enabling long-term A camera having a display unit with a long life can be obtained.

[0225] As described above, the light emitting device of the present invention has a very wide range of applications, and can be used in a variety of fields. The anthracene derivative of the present invention can be applied to various electronic devices. This makes it possible to provide an electronic device having a display unit with a long life. By using anthracene derivatives, electronic devices having displays with low power consumption can be obtained. can be done.

[0226] The light-emitting device of the present invention can also be used as a lighting device. An embodiment of the present invention used as a lighting device will be described with reference to FIG.

[0227] FIG. 7 shows an example of a liquid crystal display device using the light emitting device of the present invention as a backlight. The liquid crystal display device shown in FIG. 7 includes a housing 901, a liquid crystal layer 902, a backlight 903, and a housing 90 4, and the liquid crystal layer 902 is connected to a driver IC 905. 903 is a light emitting device of the present invention, and a terminal 906 supplies current. .

[0228] By using the light emitting device of the present invention as a backlight for a liquid crystal display device, the luminous efficiency can be improved. Furthermore, the light emitting device of the present invention can provide a backlight with high brightness and reduced power consumption. Since it is a light illumination device and can be made large, it is possible to make the backlight large. Furthermore, the light-emitting device of the present invention is thin and consumes little power. Therefore, it is possible to make the display device thinner and reduce power consumption. Therefore, a liquid crystal display device using the light emitting device of the present invention also has a long life.

[0229] FIG. 8 shows an example in which a light emitting device to which the present invention is applied is used as a desk lamp, which is a lighting device. The desk lamp shown in FIG. 8 has a housing 2001 and a light source 2002. The light emitting device of the present invention has high luminous efficiency and is usable for a long time. Because of its lifespan, the desk lamp also has high luminous efficiency and a long lifespan.

[0230] FIG. 9 shows an example in which a light emitting device according to the present invention is used as an indoor lighting device 3001. The light emitting device of the present invention can be made large in area, and therefore can be used as a large-area lighting device. Furthermore, the light emitting device of the present invention is thin and has low power consumption. In this way, the light emitting device to which the present invention is applied can be used as a lighting device for In the room used as the indoor lighting device 3001, the lighting device according to the present invention as described with reference to FIG. 6(A) was installed. By installing such a television device 3002, public broadcasting and movies can be viewed. In this case, both devices are low power consumption, so you can enjoy a powerful display in a bright room without worrying about your electricity bill. You can watch the video. [Example]

[0231] In this example, the anthracene derivative of the present invention, 4-(1 0-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazole-3-yl) A method for synthesizing PCBAPA (abbreviation: PCBAPA) will be specifically described.

[0232] [ka]

[0233] Step 1: Synthesis of 9-phenyl-9H-carbazole-3-boronic acid 10 g (31 mmol) of 3-bromo-9-phenyl-9H-carbazole in 500 mL of The mixture was placed in a three-necked flask and the atmosphere in the flask was replaced with nitrogen. mL was added to the flask and 3-bromo-9-phenyl-9H-carbazole was dissolved. The solution was cooled to -80°C. 20 mL (32 mmol) of the xanthane solution was added dropwise using a syringe. The solution was stirred at the same temperature for 1 hour. After stirring, 3.8 mL (3 4 mmol) was added, and the mixture was stirred for about 15 hours while returning to room temperature. Approximately 150 mL of (1.0 mol / L) was added and stirred for 1 hour. After stirring, the mixture was The layer was extracted with ethyl acetate, and the extracted solution and the organic layer were combined and washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, and the mixture was then gravity filtered. The obtained filtrate was concentrated to give a light brown oily substance. This oily substance was dried under reduced pressure to give a filtrate. The target product, a light brown solid, was obtained in 7.5g with a yield of 86%. This is shown in (b-1).

[0234] [ka]

[0235] [Step 2: 4-(9-phenyl-9H-carbazol-3-yl)diphenylamine (abbreviation: PCBA) synthesis] 4-Bromodiphenylamine 6.5g (26mmol), 9-phenyl-9H-carbazo 7.5 g (26 mmol) of methyl-3-boronic acid, 400 ml of tri(o-tolyl)phosphine g (1.3 mmol) was placed in a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. To the mixture, 100 mL of toluene, 50 mL of ethanol, and an aqueous solution of potassium carbonate (0.2 mo The mixture was degassed under reduced pressure with stirring, and after degassing, 14 mL of acetic acid was added. 67 mg (30 mmol) of palladium (II) was added, and the mixture was heated at 100°C for 10 hours. After refluxing, the aqueous layer of this mixture was extracted with toluene, and the extracted solution and the organic layer were combined. The organic layer was washed with saturated saline, dried over magnesium sulfate, and the mixture was then The resulting filtrate was concentrated to give a light brown oil. Purification was performed by gel column chromatography (developing solvent: hexane:toluene = 4:6). The white solid obtained after purification was recrystallized from dichloromethane / hexane to obtain the target white solid. The compound was obtained in an amount of 4.9 g with a yield of 45%. The synthetic scheme of Step 2 is shown below in (b-2).

[0236] [ka]

[0237] The solid obtained in step 2 was analyzed by nuclear magnetic resonance spectroscopy ( 1 1 H NMR was measured. The measurement data is shown below. 1 The H NMR chart is shown in Figure 10. B) is an enlarged view of the range of 6.0 ppm to 9.0 ppm in Figure 10(A). From the measurement results, it was found that the anthracene derivative of the present invention represented by the above structural formula (100) It was found that PCBA, an organic compound of the present invention, was obtained. Ta.

[0238] 1H NMR(DMSO-d6,300MHz):δ=6.81-6.86(m,1H) ,7.12(dd,J1=0.9Hz,J2=8.7Hz,2H),7.19(d,J= 8.7Hz,2H),7.23-7.32(m,3H),7.37-7.47(m,3H ),7.51-7.57(m,1H),7.61-7.73(m,7H)8.28(s, 1H),8.33(d,J=7.2Hz,1H),8.50(d,J=1.5Hz,1H )

[0239] [Step 3: Synthesis of PCBAPA] 9-(4-bromophenyl)-10-phenylanthracene 7.8 g (12 mmol), PCBA 4.8g (12mmol), sodium tert-butoxide 5.2g (52 (mmol) was placed in a 300 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. , toluene 60 mL, tri(tert-butyl)phosphine (10 wt% hexane solution) 0.30 mL of the mixture was added. The mixture was degassed under reduced pressure while stirring. After degassing, bis(dichloromethane) 136 mg (0.24 mmol) of (benzylideneacetone)palladium(0) was added. The mixture was stirred at 100°C for 3 hours. After stirring, about 50 mL of toluene was added to the mixture. In addition, Celite (Wako Pure Chemical Industries, Ltd., Catalog No.: 531-16855), aluminum Through Florisil (Wako Pure Chemical Industries, Ltd., catalog number: 540-00135) The resulting filtrate was concentrated to give a yellow solid. The product was recrystallized in ethanol to obtain 6.6 g of a pale yellow solid of PCBAPA in a yield of 75%. 3.0 g of the resulting pale yellow powdery solid was purified by train sublimation. The preparation conditions were a pressure of 8.7 Pa, argon gas at a flow rate of 3.0 mL / min, and 3 PCBAPA was heated at 50°C. After purification by sublimation, 2.7 g of the pale yellow solid PCBAPA was collected. The yield was 90%. The synthesis scheme for Step 3 is shown below in (b-3).

[0240] [ka]

[0241] In addition, the solid obtained in step 3 above 1 H NMR was measured. The measurement data is shown below. Also, 1 The H NMR chart is shown in Figure 11. Note that Figure 11(B) is the same as Figure 11(A). 1 is a chart showing an enlarged range of 7.0 ppm to 8.5 ppm in the measurement results. From this, the anthracene derivative PCBAPA of the present invention represented by the above structural formula (100) can be obtained. It was found that

[0242] 1 H NMR(CDCl3,300MHz):δ=7.09-7.14(m,1H),7 .28-7.72(m,33H),7.88(d,J=8.4Hz,2H),8.19( d,J=7.2Hz,1H),8.37(d,J=1.5Hz,1H)

[0243] Next, the absorption spectrum of PCBAPA was measured. Measurements were taken at room temperature using a toluene solution and a thermometer (V550 model, manufactured by JASCO Corporation). The emission spectrum of PCBAPA was also measured. Using a spectrophotometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.), the toluene solution was The measurement results are shown in Figure 12. PCBAPA was also formed into a thin film by vapor deposition. The same measurements were carried out on the film. The measurement results are shown in Figure 13. The horizontal axis represents wavelength (nm), The vertical axis represents the absorption intensity (arbitrary units) and the emission intensity (arbitrary units).

[0244] As shown in Figures 12 and 13, the emission from PCBAPA was 459n in toluene solution. It can be seen that the thin film has a peak at 473 nm. As can be seen, PCBAPA emits blue light with high color purity. [Example]

[0245] In this embodiment, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material is shown below:

[0246] [ka]

[0247] (Light-emitting element 1) First, indium tin oxide containing silicon oxide is sputtered onto a glass substrate 1100. The first electrode 1101 was formed by a method. The area was 2 mm x 2 mm.

[0248] Next, the substrate on which the first electrode was formed was placed in a position so that the surface on which the first electrode was formed faced downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation system and -4 After reducing the pressure to about Pa, On the electrode 1101 of 1, NPB and molybdenum (VI) oxide were co-deposited to form an organic A layer 1102 containing a composite material made by combining a compound and an inorganic compound was formed. The ratio of NPB to molybdenum oxide was 4:1 (=NPB:molybdenum oxide) by weight. The co-evaporation method involves evaporating a film of 1000 volts ... This is a deposition method in which deposition is performed simultaneously on the surface and the substrate.

[0249] Next, NPB was deposited on the layer 1102 containing the composite material by a deposition method using resistance heating. The hole transport layer 1103 was formed to a thickness of 1104 mm.

[0250] Furthermore, 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo CzPA (abbreviation: CzPA) and PCBAPA were co-deposited on the hole transport layer 1103. The light-emitting layer 1104 was formed to a thickness of 30 nm. The ratio was adjusted to 1:0.10 (=CzPA:PCBAPA).

[0251] Then, tris(8-quinolinolato) was deposited on the light-emitting layer 1104 by using a vapor deposition method using resistance heating. Aluminum (abbreviation: Alq) was deposited to a thickness of 10 nm, and the electron transport layer 110 5 was formed.

[0252] Furthermore, on the electron transport layer 1105, tris(8-quinolinolato)aluminum (abbreviation: A lq) and lithium are co-evaporated to form an electron injection layer 1106 with a thickness of 20 nm. Here, the weight ratio of Alq to lithium was 1:0.01 (=Alq:lithium). It was adjusted so that

[0253] Finally, aluminum was deposited on the electron injection layer 1106 by a resistive heating evaporation method. The second electrode 1107 is formed to a thickness of 1000 nm. Device 1 was fabricated.

[0254] The current density-luminance characteristics of the light-emitting element 1 are shown in FIG. 15, and the voltage-luminance characteristics are shown in FIG. The luminance vs. current efficiency characteristics are shown in Figure 17. The luminance vs. external quantum efficiency characteristics are shown in Figure 18. The emission spectrum when a current of 1 mA is applied is shown in Figure 19. The light emitted by the optical element is that of PCBAPA. 820cd / m 2 of brightness and The CIE chromaticity coordinates of the light-emitting element 1 are (x, y) = (0.16, 0.19), and the color purity is As can be seen from FIG. 18, the light-emitting element 1 exhibited a blue light emission with a high luminance of 820 d / m 2 The external quantum efficiency at 1000 kJ / s is 2.9%, which indicates a high external quantum efficiency. Therefore, the luminous efficiency of the light-emitting element 1 is high. 2 to The current efficiency is 4.2 cd / A, which shows that the luminous efficiency is high. 16 to 820 cd / m 2 The driving voltage is 5.2V, and a certain brightness is obtained. Therefore, it is understood that the power consumption of the light-emitting element 1 is small.

[0255] The initial brightness is 1000 cd / m 2 The light-emitting element of this example was set to When Device 1 was driven, the brightness after 380 hours was still 81% of the initial brightness. In Fig. 26, the horizontal axis is time (h) and the vertical axis is the initial brightness (100%). Therefore, by applying the present invention, deterioration is reduced and the life is long. It was found that a light emitting device could be obtained. [Example]

[0256] In this embodiment, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material is shown below:

[0257] [ka]

[0258] (Light-emitting element 2) First, indium tin oxide containing silicon oxide is sputtered onto a glass substrate 2100. The first electrode 2101 was formed by a method. The area was 2 mm x 2 mm.

[0259] Next, the substrate on which the first electrode was formed was placed in a position so that the surface on which the first electrode was formed faced downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation system and -4 After reducing the pressure to about Pa, On the electrode 2101 of 1, NPB and molybdenum (VI) oxide were co-deposited to form an organic A layer 2102 containing a composite material made by combining a compound and an inorganic compound was formed. The ratio of NPB to molybdenum oxide was 4:1 (=NPB:molybdenum oxide) by weight. The co-evaporation method involves evaporating a film of 1000 volts ... This is a deposition method in which deposition is performed simultaneously on the surface and the substrate.

[0260] Next, NPB was deposited on the layer 2102 containing the composite material by a deposition method using resistance heating. The hole transporting layer 2103 was formed to a thickness of 1000 nm.

[0261] Furthermore, 9,10-diphenylanthracene (abbreviation: DPAnth) and the anthracene of the present invention A 30 nm thick film was formed on the hole transport layer 2103 by co-evaporating the ZnSe derivative PCBAPA. The first layer 2121 was formed with a thickness of 1000 μm. Here, the weight ratio of DPAnth to PCBAPA was The ratio was adjusted to 1:0.05 (=DPAnth:PCBAPA).

[0262] Furthermore, 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo By co-evaporating CzPA and the anthracene derivative PCBAPA of the present invention, Thus, a second layer 2122 having a thickness of 30 nm was formed on the first layer 2121. The weight ratio of zPA to PCBAPA was 1:0.10 (= CzPA: PCBAPA). was adjusted to.

[0263] Then, a tris(8-quinolinol) compound was deposited on the second layer 2122 by using a vapor deposition method using resistance heating. ) Aluminum (abbreviation: Alq) is deposited to a thickness of 10 nm, and an electron transport layer 21 04 was formed.

[0264] Furthermore, on the electron transport layer 2104, tris(8-quinolinolato)aluminum (abbreviation: A lq) and lithium are co-evaporated to form an electron injection layer 2105 with a thickness of 20 nm. Here, the weight ratio of Alq to lithium was 1:0.01 (=Alq:lithium). It was adjusted so that

[0265] Finally, aluminum was deposited on the electron injection layer 2105 by a resistive heating evaporation method. The second electrode 2106 is formed to a thickness of 100 μm. Device 2 was fabricated.

[0266] FIG. 21 shows the current density-luminance characteristics of the light-emitting element 2, and FIG. 22 shows the voltage-luminance characteristics. The luminance vs. current efficiency characteristics are shown in Figure 23. The luminance vs. external quantum efficiency characteristics are shown in Figure 24. The emission spectrum when a current of 1 mA is applied is shown in Figure 25. The light emitted by the optical element is that of PCBAPA. 990cd / m 2 of brightness and The CIE chromaticity coordinates of the light-emitting element 2 are (x, y) = (0.15, 0.17), and the color purity is As can be seen from FIG. 24, the light-emitting element 2 emitted blue light with a high luminance of 990 cd / m 2 The external quantum efficiency at 1000 s is 3.3%, which indicates a high external quantum efficiency. Therefore, the luminous efficiency of the light-emitting element 2 is high. 2 The current efficiency is 4.1 cd / A, which shows that the luminous efficiency is high. From Figure 22, 990 cd / m 2 The driving voltage at this point is 6.4V, and a certain level of brightness is obtained. Therefore, it is understood that the power consumption of the light-emitting element 2 is small.

[0267] The initial brightness is 1000 cd / m 2 The light-emitting element of this example was set to When device 2 was driven, the brightness remained at 81% of the initial brightness after 380 hours. In Fig. 27, the horizontal axis is time (h) and the vertical axis is the initial brightness (100%). Therefore, by applying the present invention, deterioration is reduced and the life is long. It was found that a light emitting device could be obtained. [Example]

[0268] In this example, the anthracene derivative of the present invention, 4-[4 -(10-phenyl-9-anthryl)phenyl]-4'-(9-phenyl-9H-chlor A specific method for synthesizing PCBAPBA will be explained.

[0269] [ka]

[0270] [Step 1: 9-(4'-bromobiphenyl-4-yl)-10-phenylanthracene] Synthesis of 2.8 g (7.2 mmol) of 9-iodo-10-phenylanthracene and 1.5 g ( 7.2 mmol) of 4'-bromobiphenyl-4-boronic acid into a 100 mL three-neck flask. The atmosphere in the flask was replaced with nitrogen. 40 mL of toluene and 10 mL of carbonate were added to this mixture. Aqueous sodium solution (2.0 mol / L) was added, and the mixture was stirred under reduced pressure. After degassing with 120 mg (0.10 mmol) of tetrakis(triphenylphosphine (Iron)palladium(0) was added. The mixture was stirred at 90°C for 4 hours. After stirring, the mixture Approximately 50 mL of toluene was added to the mixture, and then alumina and celite (Wako Pure Chemical Industries, Ltd.) were added. , Catalog No.: 531-16855), Florisil (Wako Pure Chemical Industries, Ltd., Catalog No. The resulting filtrate was concentrated and the resulting solid was The compound was purified by high performance liquid chromatography (mobile phase: chloroform) to give a pale yellow solid The obtained solid was recrystallized from chloroform / hexane to give the target pale yellow compound. 1.4 g of a white powdery solid was obtained in a yield of 40%. The synthesis scheme of Step 1 is shown below (c-1 ) shown.

[0271] [ka]

[0272] [Step 2: 4-[4-(10-phenyl-9-anthryl)phenyl]-4'-(9 -phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPB Synthesis of A) 1.0 g (2.1 mmol) of 9-(4'-bromobiphenyl-4-yl)-10-phenyl 4-(9-phenyl-9H-chloro-2,4-diphenyl ... (3-phenyl-3-yl)diphenylamine (PCBA) and 1.0 g (10 mmol) of NaCl Thorium tert-butoxide was placed in a 50 mL three-neck flask and the flask was filled with nitrogen. To this mixture, 15 mL of toluene and 0.10 mL of tri(tert-butyl) ) Phosphine (10 wt% hexane solution) was added. The mixture was stirred under reduced pressure. After degassing, 58 mg (0.10 mmol) of bis(dibenzylideneacetone) Radium(0) was added, and the mixture was stirred at 100°C for 5 hours. After cooling to room temperature, approximately 20 mL of toluene was added, and Florisil (Wako Pure Chemical Industries, Ltd.) was added. Company, Catalog No.: 540-00135), Celite (Wako Pure Chemical Industries, Ltd., Catalog No. The resulting filtrate was concentrated and filtered through alumina. A pale yellow solid was obtained. The obtained solid was recrystallized with toluene / hexane to obtain the target compound. The pale yellow powdery solid was obtained in an amount of 1.5 g with a yield of 90%. The synthesis scheme of Step 2 is shown below ( c-2).

[0273] [ka]

[0274] The resulting pale yellow powdery solid (1.1 g) was purified by train sublimation. The sublimation purification conditions were a pressure of 6.0 Pa and argon gas at a flow rate of 3.0 mL / min. After sublimation purification, PCBAPBA was purified into a pale yellow solid. 1.0 g was obtained with a recovery rate of 93%.

[0275] The obtained solid 1 H NMR was measured. The measurement data are shown below. 1 H NMR The chart is shown in Figure 28. Note that Figure 28(B) shows the difference between 7.0 ppm and The chart shows an enlarged range of 8.5 ppm. From the measurement results, it is clear that the above-mentioned structural formula (3 00) was obtained. .

[0276] 1 H NMR(CDCl3,300MHz):δ=7.09-7.12(m,1H),7 .25-7.31(m,12H), 7.34-7.79(m,23H),7.80-7. 85(m,4H),8.20(d,J=7.8Hz,1H),8.36(d,J=1.5 Hz, 1H)

[0277] In addition, thermogravimetry-differential thermal analysis (TG-DTA) of PCBAPBA was performed. Differential Thermal Analysis (DTA) was performed. The measurements were carried out using a high-vacuum differential thermobalance (manufactured by Bruker AXS, TG- The temperature was raised at normal pressure at a rate of 10°C / min under a nitrogen gas flow (flow rate: 2 When the measurement was performed under the condition of 0.00 mL / min, the relationship between weight and temperature (thermogravimetry) was found to be 5% The weight loss temperature was over 500°C, indicating good thermal stability.

[0278] Next, the absorption spectrum of PCBAPBA was measured. Measurement was performed at room temperature using a photometer (V550 model, manufactured by JASCO Corporation) and a toluene solution. The measurement results are shown in Figure 29. In Figure 29, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity. The emission spectrum of PCBAPBA was also measured. The torr was measured using a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) and a toluene solution. The measurement was carried out at room temperature using the above-mentioned method. The measurement results are shown in Figure 30. In Figure 30, the horizontal axis represents wavelength. (nm), and the vertical axis represents the emission intensity (arbitrary units). In the case of toluene solution, it is around 373 nm. The maximum emission wavelength was 44 nm in the case of the toluene solution. 0 nm (excitation wavelength 370 nm).

[0279] PCBAPBA was also formed into a thin film by vapor deposition, and similar measurements were carried out on the thin film. The absorption spectrum of the thin film of APBA is shown in Figure 31, and the emission spectrum of the thin film of PCBAPBA is shown in Figure 32. This is shown in Figure 32. In Figure 31, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary units). In FIG. 32, the horizontal axis represents wavelength (nm) and the vertical axis represents luminescence intensity (arbitrary units). In the case of The maximum emission wavelength was 458 nm (excitation wavelength 400 nm) in the thin film. It was.

[0280] 30 and 32 show that PCBAPBA emits blue light with high color purity. . [Example]

[0281] In this embodiment, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material is shown below:

[0282] [ka]

[0283] (Light-emitting element 3) First, indium tin oxide containing silicon oxide is sputtered onto a glass substrate 1100. The first electrode 1101 was formed by a method. The area was 2 mm x 2 mm.

[0284] Next, the substrate on which the first electrode was formed was placed in a position so that the surface on which the first electrode was formed faced downward. The substrate was fixed to a substrate holder installed in the vacuum evaporation system and -4 After reducing the pressure to about Pa, On the electrode 1101 of 1, NPB and molybdenum (VI) oxide were co-deposited to form an organic A layer 1102 containing a composite material made by combining a compound and an inorganic compound was formed. The ratio of NPB to molybdenum oxide was 4:1 (=NPB:molybdenum oxide) by weight. The co-evaporation method involves evaporating a film of 1000 volts ... This is a deposition method in which deposition is performed simultaneously on the surface and the substrate.

[0285] Next, NPB was deposited on the layer 1102 containing the composite material by a deposition method using resistance heating. The hole transport layer 1103 was formed to a thickness of 1104 mm.

[0286] Furthermore, 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazo By co-evaporating CzPA (abbreviation: CzPA) and PCBAPBA, a hole transport layer 1103 A light-emitting layer 1104 having a thickness of 30 nm was formed on the substrate. The weight ratio was adjusted to 1:0.10 (=CzPA:PCBAPBA).

[0287] Then, bathophenanthroline (abbreviation A film of ZnSe:BPhen was formed to a thickness of 30 nm to form an electron transport layer 1105 .

[0288] Furthermore, lithium fluoride (LiF) was deposited on the electron transport layer 1105 to a thickness of 1 nm. The electron injection layer 1106 was formed.

[0289] Finally, aluminum was deposited on the electron injection layer 1106 by a resistive heating evaporation method. The second electrode 1107 is formed to a thickness of 1000 nm. Device 3 was fabricated.

[0290] FIG. 33 shows the current density-luminance characteristics of the light-emitting element 3, and FIG. 34 shows the voltage-luminance characteristics. The luminance vs. current efficiency characteristics are shown in Figure 35. The luminance spectrum when a current of 1 mA is applied is The spectrum is shown in Figure 36. From Figure 36, it can be seen that the light emitted from the light-emitting element is the light emitted by PCBAPBA. 950cd / m 2 The CIE chromaticity coordinates of light-emitting element 3 at this luminance are (x, y) =(0.15, 0.12), and blue light emission with high color purity was obtained. 950cd / m 2 The external quantum efficiency at 1000 kHz was 3.7%, demonstrating high external quantum efficiency. 35, the luminance of the light-emitting element 3 is 950 cd / m 2 The current efficiency is 3. 9 cd / A, which shows that it has high luminous efficiency. / m 2 The driving voltage is 3.2V, which is low enough to obtain a certain level of brightness. In addition, the power efficiency of the light-emitting element 3 is 3.9 lm / W, and the power consumption of the light-emitting element 3 is small. You can see the details. [Explanation of symbols]

[0291] 100 boards 101 first electrode 102 Layer containing organic compounds 103 Second electrode 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 121 First Layer 122 Second Layer 401 Drive circuit section (source side drive circuit) 402 Pixel section 403 Drive circuit section (gate side drive circuit) 404 Sealing substrate 405 Sealing material 407 Space 408 Wiring 409 FPC (Flexible Printed Circuit) 410 Element substrate 411 Switching TFT 412 Current control TFT 413 First electrode 414 Insulators 416 Layer containing organic compounds 417 Second Electrode 418 Light-emitting element 423 n-channel TFT 424 p-channel TFT 501 first electrode 502 Second electrode 511 First Light Emitting Unit 512 Second Light Emitting Unit 513 Charge generation layer 901 Case 902 Liquid crystal layer 903 Backlight 904 Case 905 Driver IC 906 terminal 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 Layer containing organic compounds 956 Electrode 1100 glass substrate 1101 First electrode 1102 Layer containing composite material 1103 Hole transport layer 1104 Light-emitting layer 1105 Electron transport layer 1106 Electron injection layer 1107 Second electrode 2001 Case 2002 light source 2100 Glass Substrate 2101 First electrode 2102 Layer containing composite material 2103 Hole transport layer 2104 Electron transport layer 2105 Electron injection layer 2106 Second electrode 2121 First Layer 2122 Second Layer 3001 Lighting equipment 3002 Television equipment 9101 Housing 9102 Support stand 9103 Display section 9104 Speaker section 9105 Video input terminal 9201 Main Unit 9202 Housing 9203 Display section 9204 keyboard 9205 External connection port 9206 Pointing Device 9401 Main Unit 9402 Housing 9403 Display section 9404 Audio input unit 9405 Audio output unit 9406 Operation Key 9407 External connection port 9408 Antenna 9501 main body 9502 Display section 9503 Housing 9504 External connection port 9505 Remote control receiver 9506 Image receiving unit 9507 Battery 9508 Audio input unit 9509 Operation Key 9510 Eyepiece

Claims

[Claim 1] A compound represented by formula (1): 【Chemistry 1】 (In the formula, Ar １ and Ar ２ may be the same or different and each represent a substituted or unsubstituted aryl group having 6 to 25 carbon atoms; α and β may be the same or different and each represent a substituted or unsubstituted arylene group having 6 to 25 carbon atoms; R １ represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, R ２ represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a halogen group, or a haloalkyl group; R １１ ~R １８ may be the same or different and represent hydrogen or an alkyl group having 1 to 4 carbon atoms.

Images