JP6230904B2 - Organic compounds, light emitting devices - Google Patents

Description

    One embodiment of the present invention relates to an organic compound and a light-emitting element, a display module, a lighting module, a display device, a light-emitting device, an electronic device, and a lighting device each using the organic compound. Note that one embodiment of the present invention is not limited to the above technical field. The technical field of one embodiment of the invention disclosed in this specification and the like relates to an object, a method, or a manufacturing method. Alternatively, one embodiment of the present invention relates to a process, a machine, a manufacture, or a composition (composition of matter). Therefore, the technical field of one embodiment of the present invention disclosed in this specification more specifically includes a semiconductor device, a display device, a liquid crystal display device, a light-emitting device, a lighting device, a power storage device, a memory device, a driving method thereof, Alternatively, the production method thereof can be given as an example.

  Development of display devices that use light-emitting elements (organic EL elements) with organic compounds as light-emitting substances as next-generation lighting devices and display devices due to their potential for thin and light weight, high-speed response to input signals, and low power consumption. Accelerating.

  In an organic EL device, a voltage is applied with a light emitting layer sandwiched between electrodes, so that electrons and holes injected from the electrodes are recombined so that the light emitting material becomes an excited state and emits light when the excited state returns to the ground state. To do. The wavelength of light emitted from the light-emitting substance is unique to the light-emitting substance. By using different types of organic compounds as the light-emitting substance, light-emitting elements that emit light of various wavelengths, that is, various colors can be obtained.

  In the case of a display device such as a display that is intended to display an image, it is necessary to obtain light of at least three colors of red, green, and blue in order to reproduce a full-color image. In addition, when used as a lighting device, it is ideal to obtain light having a uniform intensity in the visible light region in order to obtain high color rendering properties. However, in reality, it has different wavelengths obtained from different luminescent materials. Light obtained by combining two or more types of light is often used for illumination purposes.

  As described above, the light emitted from the luminescent material is unique to the material. However, other important performances as a light emitting device, such as lifetime, power consumption, and luminous efficiency, do not depend only on the material that emits light, but layers other than the light emitting layer, device structure, and emission center material The properties and compatibility with the host material and the carrier balance are also greatly affected. Therefore, there is no doubt that many types of materials for light-emitting elements are required to see the maturity of this field. For these reasons, light-emitting element materials having various molecular structures have been proposed (see, for example, Patent Document 1).

  By the way, in the case of a light-emitting element utilizing electroluminescence, it is generally known that the generation rate of the excited state is 1 in the singlet excited state and 3 in the triplet excited state. Therefore, a light-emitting element using a phosphorescent material that can change a triplet excited state to light emission as an emission center substance is compared with a light-emitting element that uses a fluorescent material that changes a singlet excited state to light emission as an emission center substance. A light emitting element with high luminous efficiency can be obtained.

  Here, the host material in the host-guest type light-emitting layer and the material constituting each transport layer in contact with the light-emitting layer are wider than the light-emitting center material in order to efficiently convert excitation energy to light emission from the light-emitting center material. A substance having a band gap or a high triplet level (energy difference between a triplet excited state and a singlet ground state) is used.

  However, most of the substances used as the host material of the light-emitting element are fluorescent materials in which electronic transition between different states is forbidden. For this reason, the triplet excited state in the substance is in an energy smaller position than the singlet excited state, and when the fluorescence and phosphorescence of the same wavelength are compared, the latter uses a substance having a wider band gap as the host material. There is a need.

  Therefore, a host material and a carrier transport material having a larger band gap are required to efficiently obtain short wavelength fluorescent light emission such as blue.

In general, a substance having a wide band gap and a high triplet level is almost always a substance having a small molecular weight. This is because conjugation spreads in a substance having a large molecular weight, the band gap is narrow, and the triplet level is lowered. However, a substance having a low molecular weight has poor thermal properties such as high crystallinity, low melting point and low glass transition point, and the film quality tends to be unstable when forming a thin film. Further, since the conjugation does not spread, the carrier transportability is poor and the driving voltage tends to be high. For this reason, it is very difficult to develop a material that can be a material for a light emitting element having such a large band gap while realizing a balanced demand for important characteristics of the light emitting element such as driving voltage and high light emission efficiency.

JP 2007-15933 A

  An object of one embodiment of the present invention is to provide a novel organic compound. Another object of one embodiment of the present invention is to provide an organic compound that can be used for a light-emitting element. Another object of another embodiment of the present invention is to provide an organic compound having a high triplet excitation level. Another object of one embodiment of the present invention is to provide an organic compound with high heat resistance.

  Another object of another embodiment of the present invention is to provide a new light-emitting element. Another object is to provide a light-emitting element with high emission efficiency. Alternatively, it is an object to provide a display module, a lighting module, a light-emitting device, a display device, an electronic device, and a lighting device with low power consumption.

  One embodiment of the present invention should solve any one of the above problems.

  In one embodiment of the present invention, a substituted or unsubstituted pyridyl group at the 2-position of the dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton, Unsubstituted pyrazinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group and substituted or unsubstituted And a novel organic compound to which any one of the dibenzoquinoxalinyl groups is bonded. The said organic compound can be used suitably as a material which comprises an organic electroluminescent element. In particular, it has characteristics of high heat resistance and a high T1 level, and is suitable for a light-emitting element that emits light with a relatively short wavelength from green to blue. The organic compound can be represented by the following general formula (G0).

  In General Formula (G0), Dfha represents a substituted or unsubstituted dispiro [9H-fluorene-9,9 '(10H) -anthracene-10', 9 "-(9H) fluorene] skeleton. Het is substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl Represents any one of a group, a substituted or unsubstituted quinoxalinyl group and a substituted or unsubstituted dibenzoquinoxalinyl group, and is bonded to the 2-position of Dfha.

  The organic compound can be represented by the following general formula (G1). That is, one embodiment of the present invention is an organic compound represented by General Formula (G1) below.

  However, in General Formula G1, Het-substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or It represents any one of an unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group and a substituted or unsubstituted dibenzoquinoxalinyl group.

The organic compound is preferably an organic compound represented by the following general formula (G2). That is, another embodiment of the present invention is an organic compound represented by General Formula (G2) below.

  The organic compound is preferably an organic compound represented by the following general formula (G3). That is, another embodiment of the present invention is an organic compound represented by the following general formula (G3).

  The organic compound is preferably an organic compound represented by the following general formula (G4). That is, another embodiment of the present invention is an organic compound represented by General Formula (G4) below.

Among the organic compounds, an organic compound represented by the following structural formula (100) has a higher T1 and is more preferable. That is, another embodiment of the present invention is an organic compound represented by the following structural formula (100).

  Among the organic compounds, an organic compound represented by the following structural formula (103) has a higher T1 and is more preferable. That is, another embodiment of the present invention is an organic compound represented by the following structural formula (103).

  Among the above organic compounds, an organic compound represented by the following structural formula (107) is more preferable because of its high carrier transportability. That is, another embodiment of the present invention is an organic compound represented by the following structural formula (107).

  Another embodiment of the present invention is a light-emitting element including the above organic compound.

Another embodiment of the present invention is a light-emitting element including the above organic compound in an electron transport layer.

  Another embodiment of the present invention is a display module including the above light-emitting element.

  Another embodiment of the present invention is an illumination module including the light-emitting element.

  Another embodiment of the present invention is a light-emitting device including the above light-emitting element and means for controlling the light-emitting element.

  Another embodiment of the present invention is a display device including the above light-emitting element in a display portion and including means for controlling the light-emitting element.

  Another embodiment of the present invention is a lighting device including the above light-emitting element in a lighting portion and including means for controlling the light-emitting element.

  Another embodiment of the present invention is an electronic device including the above light-emitting element.

Note that the light-emitting device in this specification includes an image display device using a light-emitting element. In addition, a module in which a connector such as an anisotropic conductive film or TCP (Tape Carrier Package) is attached to the light emitting element, a module in which a printed wiring board is provided at the end of TCP, or a COG (Chip On Glass) system in the light emitting element A module on which an IC (integrated circuit) is directly mounted may have a light emitting device. Furthermore, the luminaire may have a light emitting device.

  In one embodiment of the present invention, a novel organic compound can be provided. Alternatively, according to another embodiment of the present invention, an organic compound that can be used for a light-emitting element can be provided. Alternatively, another embodiment of the present invention can provide an organic compound having a high triplet excitation level. Alternatively, another embodiment of the present invention can provide an organic compound with high heat resistance.

  Alternatively, another embodiment of the present invention can provide a new light-emitting element, a display module, a lighting module, a light-emitting device, a display device, an electronic device, and a lighting device, respectively. Alternatively, a light-emitting element with high emission efficiency can be provided. Alternatively, a display module, a lighting module, a light-emitting device, a display device, an electronic device, and a lighting device with low power consumption can be provided.

  One embodiment of the present invention may exhibit any one of the above effects.

The conceptual diagram of a light emitting element. 1 is a conceptual diagram of an active matrix light-emitting device. 1 is a conceptual diagram of an active matrix light-emitting device. 1 is a conceptual diagram of an active matrix light-emitting device. 1 is a conceptual diagram of a passive matrix light emitting device. The figure showing an illuminating device. FIG. 10 illustrates an electronic device. The figure showing a light source device. The figure showing an illuminating device. The figure showing an illuminating device. The figure showing a vehicle-mounted display apparatus and an illuminating device. FIG. 10 illustrates an electronic device. NMR chart of 2PyDfha. MS spectrum of 2PyDfha. NMR chart of 2PmDfha. MS spectrum of 2PmDfha. NMR chart of 2DBqDfha. MS spectrum of 2DBqDfha. Luminance-current efficiency characteristics of the light-emitting element 1 and the light-emitting element 2. Luminance-external quantum efficiency characteristics of the light-emitting element 1 and the light-emitting element 2. 2 shows emission spectra of the light-emitting element 1 and the light-emitting element 2. Luminance-chromaticity characteristics of the light-emitting element 1 and the light-emitting element 2. Luminance-current efficiency characteristics of the light-emitting elements 3 to 5. Luminance-external quantum efficiency characteristics of the light-emitting elements 3 to 5. 10 shows emission spectra of the light-emitting elements 3 to 5. Luminance-chromaticity characteristics of the light-emitting elements 3 to 5. 4 is a spin density distribution of an organic compound of one embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it is easily understood by those skilled in the art that modes and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments below.

  It has been found that Tg, which is one of the heat resistance indicators of substances used in organic electroluminescent devices, generally tends to increase as the molecular weight of the substance increases. However, a molecule having a large molecular weight tends to have a wide conjugation and a narrow band gap. Accordingly, the triplet excitation level (T1 level) is also reduced, and it is not easy to obtain a material that has both a high Tg and a high T1 level.

  Furthermore, the T1 level is affected not only by the band gap but also by other factors such as the overlap of HOMO and LUMO, so it is very difficult to obtain a substance having a high T1 level and high Tg. It is.

  In addition, the material requires characteristics required as a material for an organic electroluminescence device, such as good carrier transportability and light emission.

  The organic compound which is one embodiment of the present invention includes a substituted or unsubstituted pyridyl at the 2-position of the dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton. A group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, and It is a novel organic compound to which any one of substituted or unsubstituted dibenzoquinoxalinyl groups is bonded. The organic compound can be represented by the following general formula (G0).

  In General Formula (G0), Dfha represents a substituted or unsubstituted dispiro [9H-fluorene-9,9 '(10H) -anthracene-10', 9 "-(9H) fluorene] skeleton. Het is substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl Represents any one of a group, a substituted or unsubstituted quinoxalinyl group and a substituted or unsubstituted dibenzoquinoxalinyl group, and is bonded to the 2-position of Dfha. In addition, when these have a substituent, as said substituent, a C1-C6 alkyl group or a phenyl group is mentioned. Specific examples of the alkyl group having 1 to 6 carbon atoms include, for example, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, and tert-butyl group. , A pentyl group, a hexyl group and a cyclohexyl group.

  The organic compound represented by the general formula (G0) has a substituent in the dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton. Those which are not preferred are preferred because the synthesis is simple. The organic compound can be represented by the following general formula (G1).

  In General Formula (G1), Het is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group. Represents a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, and a substituted or unsubstituted dibenzoquinoxalinyl group. When Het has a substituent, examples of the substituent include an alkyl group having 1 to 6 carbon atoms or a phenyl group. Specific examples of the alkyl group having 1 to 6 carbon atoms include, for example, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, and tert-butyl group. , A pentyl group, a hexyl group and a cyclohexyl group.

  The organic compound has an electron transport property and can be suitably used as a host material or a carrier transport material of an organic electroluminescent element.

  In addition, since the organic compound has a high glass transition temperature (Tg), the organic compound has a high heat resistance and a high T1 level. Therefore, it is suitable for a light-emitting element that exhibits phosphorescence emission of a relatively short wavelength from green to blue.

  Note that an organic compound in which the group represented by Het is a pyridyl group, a pyrazinyl group, or a pyrimidyl group has a particularly high T1 level and is very suitable as a material constituting an organic electroluminescent element that exhibits blue phosphorescence. It is. In the above formula, an organic compound in which the group represented by Het is a quinolinyl group, a quinazolinyl group, or a dibenzoquinoxalinyl group is a preferable embodiment because of its good carrier transportability. In this case, it is very suitable as a material constituting an organic electroluminescence device that exhibits phosphorescence having a wavelength longer than that of green.

  That is, among the organic compounds represented by the general formula (G1), an organic compound represented by the following general formula (G2) is preferable.

  In addition, among the organic compounds represented by the general formula (G1), an organic compound represented by the following general formula (G3) is preferable.

  Of the organic compounds represented by the general formula (G1), an organic compound represented by the following general formula (G4) is preferable.

  Specific examples of the organic compound having the above-described configuration include the following.

  As described above, various reactions can be applied to the method for synthesizing the organic compound of one embodiment of the present invention. The organic compound represented by the general formula (G1) can be synthesized by a simple synthesis scheme. For example, as shown in the following scheme (f-1), an anthracene compound represented by the above general formula (G0) is obtained by coupling an anthracene boron compound (a1) and a halogenated hetero compound (a2). It is done.

In the above scheme, Dfha represents a substituted or unsubstituted dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton, and Het is substituted or unsubstituted. Pyridyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group And any one of a substituted or unsubstituted dibenzoquinoxalinyl group. Het is bonded to position 2 of Dfha. X ¹ represents halogen, preferably bromine or iodine, and more preferably iodine because of high reactivity. B ¹ represents boronic acid or dialkoxyboron.

  The coupling reaction in the scheme (f-1) has various reaction conditions. An example thereof is a synthesis method using a metal catalyst in the presence of a base. Typically, the Suzuki-Miyaura reaction can be used.

In scheme (f-1), the boron compound group B ¹ of the compound (a1) and the halogen group X ¹ of the compound (a2) were reacted, but the compound (a1) was a halide and the compound (a2). Can be coupled as a boron compound, the carbazole compound represented by the general formula (G0) can be obtained.

≪Light emitting element≫
Next, an example of a light-emitting element which is one embodiment of the present invention is described below with reference to FIG.

  The light-emitting element in this embodiment includes a first electrode 101, a second electrode 102, and an EL layer 103 provided between the first electrode 101 and the second electrode 102. . Note that the following description will be made on the assumption that the first electrode 101 functions as an anode and the second electrode 102 functions as a cathode.

  Since the first electrode 101 functions as an anode, it is preferably formed using a metal, an alloy, a conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing zinc oxide and zinc oxide ( IWZO) and the like. These conductive metal oxide films are usually formed by a sputtering method, but may be formed by applying a sol-gel method or the like. As an example of a manufacturing method, indium oxide-zinc oxide is formed by a sputtering method using a target in which 1 to 20 wt% of zinc oxide is added to indium oxide. Further, indium oxide (IWZO) containing tungsten oxide and zinc oxide is formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide. You can also In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), or a nitride of a metal material (for example, titanium nitride). Graphene can also be used. Note that by using a composite material described later for a layer in contact with the first electrode 101 in the EL layer 103, an electrode material can be selected regardless of a work function.

  Regarding the stacked structure of the EL layer 103, pyridinyl at the 2-position of the dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton is added to any of the stacked structures. It is preferable that a novel organic compound in which any one of a group, a pyrimidinyl group and a quinoxalinyl group is bonded is included. The stacked structure can be configured by appropriately combining a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a carrier block layer, an intermediate layer, and the like. In this embodiment, the EL layer 103 includes a hole injection layer 111, a hole transport layer 112, a light emitting layer 113, an electron transport layer 114, and an electron injection layer 115 that are sequentially stacked over the first electrode 101. Will be described. Specific examples of materials constituting each layer are shown below.

The hole injection layer 111 is a layer containing a substance having a high hole injection property. Molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, or the like can be used. In addition, phthalocyanine compounds such as phthalocyanine (abbreviation: H ₂ Pc) and copper phthalocyanine (CuPC), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N, N′-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N′-diphenyl- (1,1′-biphenyl) -4,4′-diamine (abbreviation: The hole injection layer 111 can also be formed by an aromatic amine compound such as DNTPD) or a polymer such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS). it can.

For the hole-injecting layer 111, a composite material in which an acceptor substance is contained in a hole-transporting substance can be used. Note that by using a hole transporting substance containing an acceptor substance, a material for forming the electrode can be selected regardless of the work function of the electrode. That is, not only a material with a high work function but also a material with a low work function can be used for the first electrode 101. As the acceptor substance, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane (abbreviation: F ₄ -TCNQ), chloranil, and the like can be given. Moreover, a transition metal oxide can be mentioned. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be given. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferable because of their high electron accepting properties. Among these, molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.

As the hole-transporting substance used for the composite material, various organic compounds such as aromatic amine compounds, carbazole derivatives, aromatic hydrocarbons, and high molecular compounds (oligomers, dendrimers, polymers, and the like) can be used. Note that the organic compound used for the composite material is preferably an organic compound having a high hole-transport property. Specifically, a substance having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher is preferable. Hereinafter, organic compounds that can be used as the hole transporting substance in the composite material are specifically listed.

  For example, as an aromatic amine compound, N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4′-bis [N- (4- Diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), N, N′-bis {4- [bis (3-methylphenyl) amino] phenyl} -N, N′-diphenyl- (1,1 '-Biphenyl) -4,4'-diamine (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), etc. Can do.

  Specific examples of the carbazole derivative that can be used for the composite material include 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3 , 6-Bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9- Phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) and the like.

  As other carbazole derivatives that can be used for the composite material, 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) Phenyl] benzene (abbreviation: TCPB), 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA), 1,4-bis [4- (N-carbazolyl) phenyl] -2,3,5,6-tetraphenylbenzene and the like can be used.

Examples of aromatic hydrocarbons that can be used for 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 ( Abbreviations: t-BuDBA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis (4-methyl-1-naphthyl) anthracene (abbreviation: DMNA), 2-tert-butyl-9, 0-bis [2- (1-naphthyl) phenyl] anthracene, 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, 10,10'-diphenyl-9,9'-bianthryl, 10 , 10′-bis (2-phenylphenyl) -9,9′-bianthryl, 10,10′-bis [(2,3,4,5,6-pentaphenyl) phenyl] -9,9′-bianthryl, Anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra (tert-butyl) perylene and the like can be mentioned. In addition, pentacene, coronene, and the like can also be used. Thus, it is more preferable to use an aromatic hydrocarbon having a hole mobility of 1 × 10 ⁻⁶ cm ² / Vs or more and having 14 to 42 carbon atoms.

  Note that the aromatic hydrocarbon that can be used for the composite material may have a vinyl skeleton. As the aromatic hydrocarbon having a vinyl group, for example, 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2- Diphenylvinyl) phenyl] anthracene (abbreviation: DPVPA) and the like.

  In addition, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD can also be used.

  By forming the hole injecting layer, the hole injecting property is improved and a light emitting element with a low driving voltage can be obtained.

The hole transport layer 112 is a layer containing a hole transporting substance. Examples of the hole transporting substance include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and 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] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- ( Spiro-9,9′-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP) Aromatic amine compounds such as Or the like can be used. The substances described here are substances that have a high hole-transport property and mainly have a hole mobility of 10 ⁻⁶ cm ² / Vs or higher. The organic compounds mentioned as the hole transporting substance in the above composite material can also be used for the hole transporting layer 112. Alternatively, a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can be used. Note that the layer containing a hole-transporting substance is not limited to a single layer, and two or more layers containing the above substances may be stacked.

  The light-emitting layer 113 is a layer that includes a fluorescent material and exhibits fluorescence, and is a layer that includes a phosphorescent material and exhibits fluorescence, or a layer that includes a material exhibiting thermally activated delayed fluorescence (TADF) and exhibits TADF. But it doesn't matter. Moreover, even if it is a single layer, it may consist of several layers in which different luminescent substances are contained.

  Examples of materials that can be used as the fluorescent light-emitting substance in the light-emitting layer 113 include the following. Other fluorescent materials can also be used.

5,6-bis [4- (10-phenyl-9-anthryl) phenyl] -2,2′-bipyridine (abbreviation: PAP2BPy), 5,6-bis [4 ′-(10-phenyl-9-anthryl) Biphenyl-4-yl] -2,2′-bipyridine (abbreviation: PAPP2BPy), N, N′-bis [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -N, N′-diphenyl -Pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N, N'-bis (3-methylphenyl) -N, N'-bis [3- (9-phenyl-9H-fluoren-9-yl ) Phenyl] -pyrene-1,6-diamine (abbreviation: 1,6 mM emFLPAPrn), N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4 4′-diamine (abbreviation: YGA2S), 4- (9H-carbazol-9-yl) -4 ′-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (9H-carbazole- 9-yl) -4 ′-(9,10-diphenyl-2-anthryl) triphenylamine (abbreviation: 2YGAPPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert-butylperylene (abbreviation: TBP), 4- (10-phenyl-9-anthryl) -4 ' -(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBAPA), N, N ″-(2-tert-butylanthra -9,10-diyldi-4,1-phenylene) bis [N, N ′, N′-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N, 9-diphenyl-N- [4 -(9,10-diphenyl-2-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: 2PCAPPA), N- [4- (9,10-diphenyl-2-anthryl) phenyl] -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N, N, N ′, N ′, N ″, N ″, N ′ ″, N ′ ″-octaphenyl Dibenzo [g, p] chrysene-2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazole- 3 -Amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ′, N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1 , 1′-biphenyl-2-yl) -2-anthryl] -N, N ′, N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1′- Biphenyl-2-yl) -N- [4- (9H-carbazol-9-yl) phenyl] -N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N, N, 9-triphenylant Sen-9-amine (abbreviation: DPhAPhA) coumarin 545T, N, N′-diphenylquinacridone, (abbreviation: DPQd), rubrene, 5,12-bis (1,1′-biphenyl-4-yl) -6,11 -Diphenyltetracene (abbreviation: BPT), 2- (2- {2- [4- (dimethylamino) phenyl] ethenyl} -6-methyl-4H-pyran-4-ylidene) propanedinitrile (abbreviation: DCM1), 2- {2-Methyl-6- [2- (2,3,6,7-tetrahydro-1H, 5H-benzo [ij] quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene} propanedi Nitrile (abbreviation: DCM2), N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14- Phenyl-N, N, N ′, N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), 2- {2-isopropyl-6 -[2- (1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H-benzo [ij] quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene } Propanedinitrile (abbreviation: DCJTI), 2- {2-tert-butyl-6- [2- (1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H- Benzo [ij] quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene} propanedinitrile (abbreviation: DCJTB), 2- (2,6-bis {2- [4- (dimethylamino) phenyl] Ethenyl } -4H-pyran-4-ylidene) propanedinitrile (abbreviation: BisDCM), 2- {2,6-bis [2- (8-methoxy-1,1,7,7-tetramethyl-2,3, 6,7-tetrahydro-1H, 5H-benzo [ij] quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene} propanedinitrile (abbreviation: BisDCJTM), and the like. In particular, condensed aromatic diamine compounds typified by pyrenediamine compounds such as 1,6FLPAPrn and 1,6mMemFLPAPrn are preferable because they have high hole trapping properties and are excellent in luminous efficiency and reliability.

Examples of materials that can be used as the phosphorescent material in the light-emitting layer 113 include the following.

Tris {2- [5- (2-methylphenyl) -4- (2,6-dimethylphenyl) -4H-1,2,4-triazol-3-yl-κN2] phenyl-κC} iridium (III) ( Abbreviations: [Ir (mpptz-dmp) ₃ ]), tris (5-methyl-3,4-diphenyl-4H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir (Mptz) ₃ ]) 4H, such as Tris [4- (3-biphenyl) -5-isopropyl-3-phenyl-4H-1,2,4-triazolate] iridium (III) (abbreviation: [Ir (iPrptz-3b) ₃ ]) An organometallic iridium complex having a triazole skeleton or tris [3-methyl-1- (2-methylphenyl) -5-phenyl-1H-1,2,4-triazolate] iridium (II I) (abbreviation: [Ir (Mptz1-mp) ₃ ]), tris (1-methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato) iridium (III) (abbreviation: [Ir ( Organometallic iridium complexes having a 1H-triazole skeleton such as Prptz1-Me) ₃ ]) and fac-tris [(1-2,6-diisopropylphenyl) -2-phenyl-1H-imidazole] iridium (III) ( Abbreviation: [Ir (iPrpmi) ₃ ]), tris [3- (2,6-dimethylphenyl) -7-methylimidazo [1,2-f] phenanthridinato] iridium (III) (abbreviation: [Ir ( organometallic iridium complexes having an imidazole skeleton such as dmpimpt-Me) ₃ ]) and bis [2- (4 ′, 6′-difluorophenyl) pyri Dinato-N, C ^{2 ′} ] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C ^{2 ′} ] iridium (III ) Picolinate (abbreviation: FIrpic), bis {2- [3 ′, 5′-bis (trifluoromethyl) phenyl] pyridinato-N, C ^{2 ′} } iridium (III) picolinate (abbreviation: [Ir (CF ₃ ppy) ₂ (pic)]), phenyl having an electron withdrawing group such as bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C ^{2 ′} ] iridium (III) acetylacetonate (abbreviation: FIracac). And organometallic iridium complexes having a pyridine derivative as a ligand. These are compounds that exhibit blue phosphorescence emission, and are compounds having an emission peak from 440 nm to 520 nm.

In addition, tris (4-methyl-6-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) ₃ ]), tris (4-t-butyl-6-phenylpyrimidinato) iridium (III) (Abbreviation: [Ir (tBupppm) ₃ ]), (acetylacetonato) bis (6-methyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (mppm) ₂ (acac)]), ( Acetylacetonato) bis (6-tert-butyl-4-phenylpyrimidinato) iridium (III) (abbreviation: [Ir (tBupppm) ₂ (acac)]), (acetylacetonato) bis [6- (2- Norbornyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (nbppm) ₂ (acac)]), (acetylacetonato ) Bis [5-methyl-6- (2-methylphenyl) -4-phenylpyrimidinato] iridium (III) (abbreviation: [Ir (mpmppm) ₂ (acac)]), (acetylacetonato) bis (4 , 6-diphenylpyrimidinato) iridium (III) (abbreviation: [Ir (dppm) ₂ (acac)]) or an organometallic iridium complex having a pyrimidine skeleton, or (acetylacetonato) bis (3,5- Dimethyl-2-phenylpyrazinato) iridium (III) (abbreviation: [Ir (mppr-Me) ₂ (acac)]), (acetylacetonato) bis (5-isopropyl-3-methyl-2-phenylpyrazina) Doo) iridium (III) _{(abbreviation: [Ir (mppr-iPr)} 2 (acac)] organometallic Ili with) pyrazine skeleton, such as And um complex, tris (2-phenylpyridinato--N, C ^{2 ')} iridium (III) _{(abbreviation: [Ir (ppy) 3]} ), bis (2-phenylpyridinato--N, C ^2') Iridium (III) acetylacetonate (abbreviation: [Ir (ppy) ₂ (acac)]), bis (benzo [h] quinolinato) iridium (III) acetylacetonate (abbreviation: [Ir (bzq) ₂ (acac)] ), Tris (benzo [h] quinolinato) iridium (III) (abbreviation: [Ir (bzq) ₃ ]), tris (2-phenylquinolinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir ( pq) ₃ ]), bis (2-phenylquinolinato-N, C ^{2 ′} ) iridium (III) acetylacetonate (abbreviation: [Ir (pq) ₂ (acac)]). In addition to an organometallic iridium complex having a lysine skeleton, a rare earth metal complex such as tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: [Tb (acac) ₃ (Phen)]) can be given. These are compounds which emit green phosphorescence mainly, and have a light emission peak at 500 nm to 600 nm. Note that an organometallic iridium complex having a pyrimidine skeleton is particularly preferable because of its outstanding reliability and luminous efficiency.

In addition, (diisobutyrylmethanato) bis [4,6-bis (3-methylphenyl) pyrimidinato] iridium (III) (abbreviation: [Ir (5 mdppm) ₂ (divm)]), bis [4,6-bis ( 3-methylphenyl) pyrimidinato] (dipivaloylmethanato) iridium (III) (abbreviation: [Ir (5 mdppm) ₂ (dpm)]), bis [4,6-di (naphthalen-1-yl) pyrimidinato] ( Organometallic iridium complexes having a pyrimidine skeleton such as dipivaloylmethanato) iridium (III) (abbreviation: [Ir (d1npm) ₂ (dpm)]), and (acetylacetonato) bis (2,3,5- tri phenylpyrazinato) iridium (III) _{(abbreviation: [Ir (tppr) 2 (} acac)]), bis (2,3,5-triphenyl Rajinato) (dipivaloylmethanato) iridium (III) _{(abbreviation: [Ir (tppr) 2 (} dpm])]), ( acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III) (abbreviation: [Ir (Fdpq) ₂ (acac)]) or an organometallic iridium complex having a pyrazine skeleton, or tris (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) acetyl Such as acetonate (abbreviation: [Ir (piq) ₃ ]), bis (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) (abbreviation: [Ir (piq) ₂ (acac)]) In addition to organometallic iridium complexes having a pyridine skeleton, 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphy Emissions platinum (II) (abbreviation: PtOEP) and platinum complexes such as tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: [Eu _{(DBM) 3} (Phen)]), tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: [Eu (TTA) ₃ (Phen)]) Such rare earth metal complexes are mentioned. These are compounds that exhibit red phosphorescence, and have an emission peak from 600 nm to 700 nm. An organometallic iridium complex having a pyrazine skeleton can emit red light with good chromaticity.

  In addition to the phosphorescent compounds described above, various phosphorescent light emitting materials may be selected and used.

  The following can be used as the TADF material.

Fullerene and its derivatives, acridine derivatives such as proflavine, eosin and the like. A metal-containing porphyrin containing magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), palladium (Pd), or the like. Examples of the metal-containing porphyrin include a protoporphyrin-tin fluoride complex (SnF ₂ (Proto IX)), a mesoporphyrin-tin fluoride complex (SnF ₂ (Meso IX)) represented by the following structural formula, and hematoporphyrin. - tin fluoride complex _{(SnF 2 (Hemato IX))} , coproporphyrin tetramethyl ester - tin fluoride complex _{(SnF 2 (Copro III-4Me} )), octaethylporphyrin - tin fluoride complex _(SnF 2 _(OEP)) , Etioporphyrin-tin fluoride complex (SnF ₂ (Etio I)), octaethylporphyrin-platinum chloride complex (PtCl ₂ OEP), and the like.

In addition, 2-biphenyl-4,6-bis (12-phenylindolo [2,3-a] carbazol-11-yl) -1,3,5-triazine (PIC-TRZ) represented by the following structural formula A heterocyclic compound having a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, such as, can also be used. Since the heterocyclic compound has a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring, it is preferable because of its high electron transporting property and hole transporting property. In addition, a substance in which a π-electron rich heteroaromatic ring and a π-electron deficient heteroaromatic ring are directly bonded increases both the donor property of the π-electron rich heteroaromatic ring and the acceptor property of the π-electron deficient heteroaromatic ring. , Because the energy difference between the S ₁ level and the T ₁ level is small.

  As a host material of the light emitting layer, there are pyridinyl group, pyrimidinyl group and quinoxalinyl group at the 2-position of the dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton. It is preferable to use a novel organic compound in which any one of them is bonded. The organic compound can be represented by the following general formula (G1), for example.

  However, in General Formula (G1), Het represents any one of a pyrazinyl group, a pyrimidinyl group, and a quinoxalinyl group.

  Since the organic compound having such a structure has high Tg, it is easy to obtain a light-emitting element with favorable heat resistance. In addition, since the T1 level is also high, efficient light emission can be obtained in green to blue phosphorescent light emitting elements. In addition, it is easy to obtain a light emitting element having both heat resistance and green to blue efficient phosphorescence emission.

  In the case where the above organic compound is not used as the host material, various carrier transport materials can be used instead.

As a material having an electron transporting property, for example, bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) Aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), Metal complexes such as bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4 -Oxadiazole (abbreviation: PBD), 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-to Azole (abbreviation: TAZ), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 9- [ 4- (5-phenyl-1,3,4-oxadiazol-2-yl) phenyl] -9H-carbazole (abbreviation: CO11), 2,2 ′, 2 ″-(1,3,5-benzene Triyl) tris (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), 2- [3- (dibenzothiophen-4-yl) phenyl] -1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm-II) ) And other heterocyclic compounds having a polyazole skeleton, 2- [3- (dibenzothiophen-4-yl) phenyl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTPDBq-II), 2 -[3 '-(Dibenzothiophen-4-yl) biphenyl-3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mDBTBPDBq-II), 2- [3'-(9H-carbazol-9-yl) biphenyl -3-yl] dibenzo [f, h] quinoxaline (abbreviation: 2mCzBPDBq), 4,6-bis [3- (phenanthrene-9-yl) phenyl] pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis [ Heterocyclic compounds having a diazine skeleton such as 3- (4-dibenzothienyl) phenyl] pyrimidine (abbreviation: 4,6mDBTP2Pm-II) and 3,5-bis [3- (9H-carbazol-9-yl) phenyl] Pyridine (abbreviation: 35DCzPPy), 1,3,5-tri [3- (3-pyridyl) -phenyl] benzene (abbreviation: TmPy) B) and a heterocyclic compound having a pyridine skeleton such. Among the compounds described above, a heterocyclic compound having a diazine skeleton and a heterocyclic compound having a pyridine skeleton are preferable because of their good reliability. In particular, a heterocyclic compound having a diazine (pyrimidine or pyrazine) skeleton has a high electron transporting property and contributes to a reduction in driving voltage.

  As a material having a hole transporting property, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), N, N′-bis (3-methylphenyl)- N, N′-diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4,4′-bis [N- (spiro-9,9′-bifluoren-2-yl) ) -N-phenylamino] biphenyl (abbreviation: BSPB), 4-phenyl-4 '-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9- Phenylfluoren-9-yl) triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4 ′-(9-phenyl-9H-carbazol-3-yl) triphenylamine (abbreviation: PCBA1BP), 4 4′-diphenyl-4 ″-(9-phenyl-9-H-carbazol-3-yl) triphenylamine (abbreviation: PCBBi1BP), 4- (1-naphthyl) -4 ′-(9-phenyl-9H -Carbazol-3-yl) -triphenylamine (abbreviation: PCBANB), 4,4′-di (1-naphthyl) -4 ″-(9-phenyl-9H-carbazol-3-yl) triphenylamine ( Abbreviation: PCBNBB), 9,9-dimethyl-N-phenyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -fluoren-2-amine (abbreviation: PCBAF), N-phenyl Fragrances such as —N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl] -spiro-9,9′-bifluoren-2-amine (abbreviation: PCBASF) Compounds having an amine skeleton, 1,3-bis (N-carbazolyl) benzene (abbreviation: mCP), 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 3,6-bis (3 Compounds having a carbazole skeleton such as 5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3′-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP), and 4,4 ′, 4 ″-(benzene-1,3,5-triyl) tri (dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4- [4- (9-phenyl-9H-fluorene-9- Yl) phenyl] dibenzothiophene (abbreviation: DBTFLP-III), 4- [4- (9-phenyl-9H-fluoren-9-yl) phenyl] -6-phenyldiben Compounds having a thiophene skeleton such as zothiophene (abbreviation: DBTFLP-IV), 4,4 ′, 4 ″-(benzene-1,3,5-triyl) tri (dibenzofuran) (abbreviation: DBF3P-II), 4 A compound having a furan skeleton such as — {3- [3- (9-phenyl-9H-fluoren-9-yl) phenyl] phenyl} dibenzofuran (abbreviation: mmDBFFLBi-II); Among the compounds described above, a compound having an aromatic amine skeleton and a compound having a carbazole skeleton are preferable because they have good reliability, high hole transportability, and contribute to reduction in driving voltage. In addition to the hole transport material described above, a hole transport material may be used from various substances.

  Note that the host material may be a material in which a plurality of types of substances are mixed. When a mixed host material is used, it is preferable to mix a material having an electron transporting property and a material having a hole transporting property. . By mixing a material having an electron transporting property and a material having a hole transporting property, the transportability of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The ratio of the content of the material having a hole-transporting property and the material having an electron-transporting property may be set to a material having a hole-transporting property: a material having an electron-transporting property = 1: 9 to 9: 1.

  Moreover, you may form an exciplex with these mixed host materials. By selecting a combination that forms an exciplex that emits light that overlaps with the wavelength of the absorption band on the lowest energy side of the phosphorescent material or TADF material, the exciplex becomes smoother and more efficient in energy transfer. Luminescence can be obtained. Moreover, it is preferable because the driving voltage is also reduced.

  The light emitting layer 113 having the above-described configuration can be manufactured by co-evaporation using a vacuum evaporation method, an inkjet method, a spin coating method, a dip coating method, or the like as a mixed solution.

  As the electron-transporting layer 114, a material containing an electron-transporting substance can be used as the electron-transporting substance described above as an electron-transporting material that can be used for the host material. . Note that any one of a pyridinyl group, a pyrimidinyl group, and a quinoxalinyl group is bonded to the 2-position of the dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton. Since the novel organic compound of one embodiment of the present invention also has favorable electron transport properties, it can be favorably used as one of the materials for forming the electron transport layer 114.

  Further, a layer for controlling the movement of electron carriers may be provided between the electron transport layer and the light emitting layer. This is a layer obtained by adding a small amount of a substance having a high electron trapping property to a material having a high electron transporting property as described above. By suppressing the movement of electron carriers, the carrier balance can be adjusted. Such a configuration is very effective in suppressing problems that occur when electrons penetrate through the light emitting layer (for example, a reduction in device lifetime).

Further, an electron injection layer 115 may be provided in contact with the second electrode 102 between the electron transport layer 114 and the second electrode 102. As the electron injection layer 115, an alkali metal or an alkaline earth metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), or a compound thereof can be used. For example, a layer made of a substance having an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof can be used. Further, electride may be used for the electron injection layer 115. Examples of the electride include a substance obtained by adding a high concentration of electrons to a mixed oxide of calcium and aluminum. Note that by using an electron injection layer 115 containing an alkali metal or an alkaline earth metal in a layer made of a substance having an electron transporting property, electron injection from the second electrode 102 is efficiently performed. Therefore, it is more preferable.

  As a material for forming the second electrode 102, a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs), and group 1 of the periodic table of elements such as magnesium (Mg), calcium (Ca), and strontium (Sr) Examples include elements belonging to Group 2, and alloys containing these (MgAg, AlLi), europium (Eu), ytterbium (Yb), and other rare earth metals, and alloys containing these. However, by providing an electron injection layer between the second electrode 102 and the electron transport layer, indium oxide-tin oxide containing Al, Ag, ITO, silicon or silicon oxide regardless of the work function. Various conductive materials such as the above can be used for the second electrode 102. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

  In addition, as a formation method of the EL layer 103, various methods can be used regardless of a dry method or a wet method. For example, a vacuum deposition method, an ink jet method, a spin coating method, or the like may be used. Moreover, you may form using the different film-forming method for each electrode or each layer.

  The electrode may also be formed by a wet method using a sol-gel method, or may be formed by a wet method using a paste of a metal material. Alternatively, a dry method such as a sputtering method or a vacuum evaporation method may be used.

  Light emission of the light-emitting element is extracted outside through one or both of the first electrode 101 and the second electrode 102. Therefore, one or both of the first electrode 101 and the second electrode 102 is formed using a light-transmitting electrode.

  Next, an embodiment of a light-emitting element having a structure in which a plurality of light-emitting units are stacked (hereinafter also referred to as a stacked element) will be described with reference to FIG. This light-emitting element is a light-emitting element having a plurality of light-emitting units between a first electrode and a second electrode. One light-emitting unit has a structure similar to that of the EL layer 103 illustrated in FIG. That is, the light-emitting element illustrated in FIG. 1A is a light-emitting element having one light-emitting unit, and the light-emitting element illustrated in FIG. 1B can be a light-emitting element having a plurality of light-emitting units.

  In FIG. 1B, an EL including a stack of a first light-emitting unit 511, a charge generation layer 513, and a second light-emitting unit 512 is provided between the first electrode 501 and the second electrode 502. A layer 503 is formed. The first electrode 501 and the second electrode 502 correspond to the first electrode 101 and the second electrode 102 in FIG. 1A, respectively, and are the same as those described in the description of FIG. can do. Further, the first light emitting unit 511 and the second light emitting unit 512 may have the same configuration or different configurations.

  The charge generation layer 513 includes a composite material of an organic compound and a metal oxide. As the composite material of the organic compound and the metal oxide, a composite material that can be used for the hole-injection layer 111 illustrated in FIG. 1A can be used. Since the composite material of an organic compound and a metal oxide is excellent in carrier injecting property and carrier transporting property, low voltage driving and low current driving can be realized. Note that in the case where the surface of the light emitting unit on the anode side is in contact with the charge generation layer, the charge generation layer also serves as a hole injection layer of the light emission unit. .

  Note that the charge generation layer 513 may be formed as a stacked structure in which a layer including the composite material and a layer formed using another material are combined. For example, you may form by laminating | stacking the layer containing a composite material and the layer containing one compound chosen from the electron-donating substance, and a compound with high electron-transport property. Alternatively, a layer including a composite material of an organic compound and a metal oxide and a transparent conductive film may be stacked.

  Further, an electron injection buffer layer may be provided between the charge generation layer 513 and the light emitting unit on the anode side of the charge generation layer. The electron injection buffer layer is formed by stacking an extremely thin alkali metal film and an electron relay layer containing an electron transporting substance. The extremely thin alkali metal film corresponds to the electron injection layer 115 and has a function of reducing an electron injection barrier. The electron relay layer has a function of preventing the interaction between the alkali metal film and the charge generation layer and smoothly transferring electrons. The LUMO level of the electron transporting substance contained in the electron relay layer is the LUMO level of the acceptor substance in the charge generation layer 513 and the substance contained in the layer in contact with the electron injection buffer layer in the light emitting unit on the anode side. It is formed so as to be between the LUMO levels. As a specific numerical value of the energy level, the LUMO level of the electron transporting substance contained in the electron relay layer is −5.0 eV or more, preferably −5.0 eV or more and −3.0 eV or less. Note that as the electron transporting substance contained in the electron relay layer, a phthalocyanine-based material or a metal complex having a metal-oxygen bond and an aromatic ligand is preferably used. In this case, since the alkali metal film of the electron injection buffer layer plays a role of the electron injection layer in the light emitting unit on the anode side, it is not necessary to form the electron injection layer on the light emitting unit.

  In any case, when the voltage is applied to the first electrode 501 and the second electrode 502, the charge generation layer 513 sandwiched between the first light emitting unit 511 and the second light emitting unit 512 has one light emitting unit. Any device may be used as long as it injects electrons into the other light-emitting unit and injects holes into the other light-emitting unit. For example, in FIG. 1B, in the case where a voltage is applied so that the potential of the first electrode is higher than the potential of the second electrode, the charge generation layer 513 has electrons in the first light-emitting unit 511. As long as it injects holes into the second light emitting unit 512.

  Although FIG. 1B illustrates a light-emitting element having two light-emitting units, the present invention can be similarly applied to a light-emitting element in which three or more light-emitting units are stacked. By arranging a plurality of light emitting units separated by a charge generation layer between a pair of electrodes, it is possible to emit light with high luminance while maintaining a low current density, and to realize an element having a longer lifetime. In addition, a light-emitting device that can be driven at a low voltage and has low power consumption can be realized.

  Further, by making the light emission colors of the respective light emitting units different, light emission of a desired color can be obtained as the whole light emitting element. For example, in a light-emitting element having two light-emitting units, a light-emitting element that emits white light as a whole is obtained by obtaining red and green light-emitting colors with a first light-emitting unit and blue light-emitting color with a second light-emitting unit. It is also easy to obtain.

≪Light emitting device≫
A light-emitting device of one embodiment of the present invention is described with reference to FIGS. 2A is a top view illustrating the light-emitting device, and FIG. 2B is a cross-sectional view taken along lines AB and CD of FIG. 2A. This light-emitting device includes a drive circuit portion (source line drive circuit) 601, a pixel portion 602, and a drive circuit portion (gate line drive circuit) 603 indicated by dotted lines, which control light emission of the light-emitting elements. Reference numeral 604 denotes a sealing substrate, reference numeral 605 denotes a sealing material, and the inside surrounded by the sealing material 605 is a space 607.

  Note that the lead wiring 608 is a wiring for transmitting a signal input to the source line driver circuit 601 and the gate line driver circuit 603, and a video signal, a clock signal, an FPC (flexible printed circuit) 609 serving as an external input terminal, Receives start signal, reset signal, etc. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to the FPC. The light-emitting device in this specification includes not only a light-emitting device body but also a state in which an FPC or a PWB is attached thereto.

  Next, a cross-sectional structure will be described with reference to FIG. A driver circuit portion and a pixel portion are formed over the element substrate 610. Here, a source line driver circuit 601 that is a driver circuit portion and one pixel in the pixel portion 602 are illustrated.

  Note that the source line driver circuit 601 is a CMOS circuit in which an n-channel FET 623 and a p-channel FET 624 are combined. The drive circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment mode, a driver integrated type in which a driver circuit is formed over a substrate is shown; however, this is not necessarily required, and the driver circuit can be formed outside the substrate.

  The pixel portion 602 is formed by a plurality of pixels including the switching FET 611, the current control FET 612, and the first electrode 613 electrically connected to the drain thereof, but is not limited thereto. The pixel portion may be a combination of two or more FETs and a capacitor.

  The type and crystallinity of the semiconductor used for the FET are not particularly limited, and an amorphous semiconductor or a crystalline semiconductor may be used. As an example of a semiconductor used for an FET, a group IV (silicon, gallium, etc.) semiconductor, a compound semiconductor, an oxide semiconductor, and an organic semiconductor material can be used, but an oxide semiconductor is particularly preferable. Examples of the oxide semiconductor include In—Ga oxide and In—M—Zn oxide (M is Al, Ga, Y, Zr, La, Ce, or Nd). Note that the use of an oxide semiconductor material with an energy gap of 2 eV or more, preferably 2.5 eV or more, more preferably 3 eV or more can reduce the off-state current of the transistor, which is a preferable structure.

  Note that an insulator 614 is formed so as to cover an end portion of the first electrode 613. Here, a positive photosensitive acrylic resin film can be used.

  In order to improve the coverage, a curved surface having a curvature is formed at the upper end or the lower end of the insulator 614. For example, in the case where positive photosensitive acrylic is used as a material for the insulator 614, it is preferable that only the upper end portion of the insulator 614 has a curved surface with a curvature radius (0.2 μm to 3 μm). As the insulator 614, either a negative photosensitive resin or a positive photosensitive resin can be used.

  An EL layer 616 and a second electrode 617 are formed over the first electrode 613. These are the first electrode 101, the EL layer 103, and the second electrode 102 described in FIG. 1A, respectively, or the first electrode 501, the EL layer 503, and the second electrode 502 described in FIG. It corresponds to.

  The EL layer 616 includes any one of a pyridinyl group, a pyrimidinyl group, and a quinoxalinyl group at the 2-position of a dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton. It is preferable that a novel organic compound in which is bonded.

  Further, the sealing substrate 604 is bonded to the element substrate 610 with the sealant 605, whereby the light-emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. Yes. Note that the space 607 is filled with a filler, and may be filled with a sealant 605 in addition to an inert gas (such as nitrogen or argon). When a recess is formed in the sealing substrate and a drying material 625 is provided there, deterioration due to the influence of moisture can be suppressed, which is a preferable structure.

  It is preferable to use an epoxy resin or glass frit for the sealant 605. Moreover, it is desirable that these materials are materials that do not transmit moisture and oxygen as much as possible. As a material used for the element substrate 610 and the sealing substrate 604, a glass substrate or a quartz substrate, or a plastic substrate made of FRP (Fiber Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used.

  For example, in this specification and the like, transistors and light-emitting elements can be formed using various substrates. The kind of board | substrate is not limited to a specific thing. Examples of the substrate include a semiconductor substrate (for example, a single crystal substrate or a silicon substrate), an SOI substrate, a glass substrate, a quartz substrate, a plastic substrate, a metal substrate, a stainless steel substrate, a substrate having stainless steel foil, and a tungsten substrate. , A substrate having a tungsten foil, a flexible substrate, a laminated film, a paper containing a fibrous material, or a base film. Examples of the glass substrate include barium borosilicate glass, aluminoborosilicate glass, and soda lime glass. Examples of the flexible substrate, the laminated film, and the base film include the following. For example, there are plastics represented by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyethersulfone (PES). Another example is a synthetic resin such as acrylic. Alternatively, examples include polypropylene, polyester, vinyl, polyvinyl fluoride, or vinyl chloride. Alternatively, examples include polyester, polyamide, polyimide, aramid, epoxy, inorganic vapor deposition film, and paper. In particular, by manufacturing a transistor using a semiconductor substrate, a single crystal substrate, an SOI substrate, or the like, a transistor with small variation in characteristics, size, or shape, high current capability, and small size can be manufactured. . When a circuit is formed using such transistors, the power consumption of the circuit can be reduced or the circuit can be highly integrated.

  Alternatively, a flexible substrate may be used as a substrate, and a transistor or a light-emitting element may be formed directly over the flexible substrate. Alternatively, a separation layer may be provided between the substrate and the transistor or between the substrate and the light-emitting element. The separation layer can be used to separate a semiconductor device from another substrate and transfer it to another substrate after a semiconductor device is partially or entirely completed thereon. At that time, the transistor can be transferred to a substrate having poor heat resistance or a flexible substrate. Note that, for example, a structure of a laminated structure of an inorganic film of a tungsten film and a silicon oxide film or a structure in which an organic resin film such as polyimide is formed over a substrate can be used for the above-described release layer.

That is, a transistor or a light-emitting element may be formed using a certain substrate, and then the transistor or the light-emitting element may be transferred to another substrate, and the transistor or the light-emitting element may be disposed on another substrate. Examples of substrates on which transistors and light-emitting elements are transferred include paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, stone substrates, wood substrates, and cloth substrates in addition to the above-described substrates on which transistors can be formed. (Natural fibers (silk, cotton, hemp), synthetic fibers (nylon, polyurethane, polyester) or recycled fibers (including acetate, cupra, rayon, recycled polyester), leather substrate, rubber substrate, etc.). By using these substrates, it is possible to form a transistor with good characteristics, a transistor with low power consumption, manufacture a device that is not easily broken, impart heat resistance, reduce weight, or reduce thickness.

  FIG. 3 shows an example of a light-emitting device in which a light-emitting element that emits white light is formed and a full color is obtained by providing a colored layer (color filter) or the like. 3A shows a substrate 1001, a base insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, and 1008, a first interlayer insulating film 1020, a second interlayer insulating film 1021, a peripheral portion 1042, and a pixel portion. 1040, a driver circuit portion 1041, light emitting element first electrodes 1024W, 1024R, 1024G, and 1024B, a partition wall 1025, an EL layer 1028, a light emitting element second electrode 1029, a sealing substrate 1031, a sealant 1032, and the like are illustrated. ing.

  In FIG. 3A, colored layers (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) are provided over a transparent base material 1033. Further, a black layer (black matrix) 1035 may be further provided. The transparent base material 1033 provided with the coloring layer and the black layer is aligned and fixed to the substrate 1001. Note that the colored layer and the black layer are covered with an overcoat layer 1036. In FIG. 3A, there are a light emitting layer that emits light without passing through the colored layer, and a light emitting layer that emits light through the colored layer of each color, and passes through the colored layer. Since the light that does not pass is white, and the light that passes through the colored layer is red, blue, and green, an image can be expressed by pixels of four colors.

  FIG. 3B illustrates an example in which a colored layer (a red colored layer 1034R, a green colored layer 1034G, and a blue colored layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020. . As described above, the coloring layer may be provided between the substrate 1001 and the sealing substrate 1031.

  In the light-emitting device described above, a light-emitting device having a structure in which light is extracted to the substrate 1001 side where the FET is formed (bottom emission type) is used. However, a structure in which light is extracted to the sealing substrate 1031 side (top-emission type). ). A cross-sectional view of a top emission type light emitting device is shown in FIG. In this case, a substrate that does not transmit light can be used as the substrate 1001. Until the connection electrode for connecting the FET and the anode of the light emitting element is manufactured, it is formed in the same manner as the bottom emission type light emitting device. Thereafter, a third interlayer insulating film 1037 is formed so as to cover the electrode 1022. This insulating film may play a role of planarization. The third interlayer insulating film 1037 can be formed using various other materials in addition to the same material as the second interlayer insulating film.

  The first electrodes 1024W, 1024R, 1024G, and 1024B of the light-emitting element are anodes here, but may be cathodes. In the case of a top emission type light emitting device as shown in FIG. 4, the first electrode is preferably a reflective electrode. The EL layer 1028 has a structure as described for the EL layer 103 in FIG. 1A or the EL layer 503 in FIG. 1B and has an element structure in which white light emission can be obtained.

  In the top emission structure as shown in FIG. 4, sealing can be performed with a sealing substrate 1031 provided with colored layers (red colored layer 1034R, green colored layer 1034G, and blue colored layer 1034B). A black layer (black matrix) 1035 may be provided on the sealing substrate 1031 so as to be positioned between the pixels. The colored layer (red colored layer 1034R, green colored layer 1034G, blue colored layer 1034B) or black layer (black matrix) may be covered with an overcoat layer 1036. Note that the sealing substrate 1031 is a light-transmitting substrate.

  Although an example in which full color display is performed with four colors of red, green, blue, and white is shown here, the present invention is not particularly limited, and full color display may be performed with three colors of red, green, and blue.

  FIG. 5 illustrates a passive matrix light-emitting device which is one embodiment of the present invention. 5A is a perspective view illustrating the light-emitting device, and FIG. 5B is a cross-sectional view taken along line XY in FIG. 5A. In FIG. 5, an EL layer 955 is provided over the substrate 951 between the electrode 952 and the electrode 956. An end portion of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided over the insulating layer 953. The side wall of the partition wall layer 954 has an inclination such that the distance between one side wall and the other side wall becomes narrower as it approaches the substrate surface. That is, the cross section in the short side direction of the partition wall layer 954 has a trapezoidal shape, and the bottom side (the side facing the insulating layer 953 in the same direction as the surface direction of the insulating layer 953) is the top side (the surface of the insulating layer 953). The direction is the same as the direction and is shorter than the side not in contact with the insulating layer 953. In this manner, by providing the partition layer 954, defects in the light-emitting element due to static electricity or the like can be prevented.

  Since the light-emitting device described above can control a large number of minute light-emitting elements arranged in a matrix with FETs formed in a pixel portion, it is suitable as a display device that expresses an image. It is a light emitting device that can be used.

≪Lighting device≫
An illumination device which is one embodiment of the present invention will be described with reference to FIG. 6B is a top view of the lighting device, and FIG. 6A is a cross-sectional view taken along line ef in FIG. 6B.

  In the lighting device, a first electrode 401 is formed over a light-transmitting substrate 400 which is a support. The first electrode 401 corresponds to the first electrode 101 in FIGS. In the case of extracting light emission from the first electrode 401 side, the first electrode 401 is formed using a light-transmitting material.

  A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400.

  An EL layer 403 is formed over the first electrode 401. The EL layer 403 corresponds to the EL layer 103 or the EL layer 503 in FIGS. For these configurations, refer to the description.

  A second electrode 404 is formed so as to cover the EL layer 403. The second electrode 404 corresponds to the second electrode 102 in FIG. In the case where light emission is extracted from the first electrode 401 side, the second electrode 404 is formed using a highly reflective material. A voltage is supplied to the second electrode 404 by being connected to the pad 412.

  The first electrode 401, the EL layer 403, and the second electrode 404 form a light-emitting element. The lighting device is completed by fixing the light-emitting element to the sealing substrate 407 using the sealing materials 405 and 406 and sealing the light-emitting element. Either one of the sealing materials 405 and 406 may be used. In addition, a desiccant can be mixed in the inner sealing material 406 (not shown in FIG. 6B), so that moisture can be adsorbed and reliability can be improved.

  Further, by providing a part of the pad 412 and the first electrode 401 so as to extend outside the sealing materials 405 and 406, an external input terminal can be obtained. Further, an IC chip 420 mounted with a converter or the like may be provided thereon.

≪Electronic equipment≫
Examples of electronic devices that are embodiments of the present invention will be described. As an electronic device, for example, a television device (also referred to as a television or a television receiver), a monitor for a computer, a digital camera, a digital video camera, a digital photo frame, a mobile phone (also referred to as a mobile phone or a mobile phone device). And large game machines such as portable game machines, portable information terminals, sound reproduction apparatuses, and pachinko machines. Specific examples of these electronic devices are shown below.

FIG. 7A illustrates an example of a television device. In the television device, a display portion 7103 is incorporated in a housing 7101. Here, a structure in which the housing 7101 is supported by a stand 7105 is shown. An image can be displayed on the display portion 7103, and the display portion 7103 is formed by arranging light-emitting elements in a matrix.

The television device can be operated with an operation switch included in the housing 7101 or a separate remote controller 7110. Channels and volume can be operated with an operation key 7109 provided in the remote controller 7110, and an image displayed on the display portion 7103 can be operated. The remote controller 7110 may be provided with a display portion 7107 for displaying information output from the remote controller 7110.

Note that the television device is provided with a receiver, a modem, and the like. General TV broadcasts can be received by a receiver, and connected to a wired or wireless communication network via a modem, so that it can be unidirectional (sender to receiver) or bidirectional (sender and receiver). It is also possible to perform information communication between each other or between recipients).

FIG. 7B1 illustrates a computer, which includes a main body 7201, a housing 7202, a display portion 7203, a keyboard 7204, an external connection port 7205, a pointing device 7206, and the like. Note that this computer is manufactured by using light-emitting elements arranged in a matrix in the display portion 7203. The computer shown in FIG. 7B1 may have a form as shown in FIG. A computer in FIG. 7B2 includes a second display portion 7210 instead of the keyboard 7204 and the pointing device 7206. The second display portion 7210 is a touch panel type, and input can be performed by operating a display for input displayed on the second display portion 7210 with a finger or a dedicated pen. In addition, the second display portion 7210 can display not only an input display but also other images. The display portion 7203 may also be a touch panel. By connecting the two screens with hinges, it is possible to prevent troubles such as damage or damage to the screens during storage or transportation.

FIG. 7C illustrates a portable game machine which includes two housings, a housing 7301 and a housing 7302, which are connected with a joint portion 7303 so that the portable game machine can be opened or folded. A display portion 7304 manufactured by arranging light emitting elements in a matrix is incorporated in the housing 7301, and a display portion 7305 is incorporated in the housing 7302. In addition, the portable game machine shown in FIG. 7C includes a speaker portion 7306, a recording medium insertion portion 7307, an LED lamp 7308, input means (operation keys 7309, a connection terminal 7310, a sensor 7311 (force, displacement, position). , Speed, acceleration, angular velocity, number of revolutions, distance, light, liquid, magnetism, temperature, chemical, sound, time, hardness, electric field, current, voltage, power, radiation, flow rate, humidity, gradient, vibration, smell or infrared A microphone 7312) and the like. Needless to say, the structure of the portable game machine is not limited to that described above, and at least both the display portion 7304 and the display portion 7305 may be used. The portable game machine shown in FIG. 7C shares information by reading a program or data recorded in a recording medium and displaying the program or data on a display unit, or by performing wireless communication with another portable game machine. It has a function. Note that the portable game machine illustrated in FIG. 7C is not limited to this, and can have a variety of functions.

FIGS. 7D1 and 7D2 illustrate an example of a portable information terminal. The portable information terminal includes a display portion 7402 incorporated in a housing 7401, operation buttons 7403, an external connection port 7404, a speaker 7405, a microphone 7406, and the like. Note that the portable information terminal includes a display portion 7402 manufactured by arranging light-emitting elements in a matrix.

The portable information terminal illustrated in FIGS. 7D1 and 7D2 can have a structure in which information can be input by touching the display portion 7402 with a finger or the like. In this case, operations such as making a call or creating a mail can be performed by touching the display portion 7402 with a finger or the like.

There are mainly three screen modes of the display portion 7402. The first mode is a display mode mainly for displaying an image. The first is a display mode mainly for displaying images, and the second is an input mode mainly for inputting information such as characters. The third is a display + input mode in which the display mode and the input mode are mixed.

For example, when making a call or creating a mail, the display portion 7402 may be set to a character input mode mainly for inputting characters, and an operation for inputting characters displayed on the screen may be performed. In this case, it is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402.

In addition, by providing a detection device having a sensor for detecting inclination such as a gyroscope or an acceleration sensor inside the mobile phone, the orientation (portrait or horizontal) of the mobile phone is determined, and the screen display of the display portion 7402 is automatically displayed. Can be switched automatically.

Further, the screen mode is switched by touching the display portion 7402 or operating the operation button 7403 of the housing 7401. Further, switching can be performed depending on the type of image displayed on the display portion 7402. For example, if the image signal to be displayed on the display unit is moving image data, the mode is switched to the display mode, and if it is text data, the mode is switched to the input mode.

Further, in the input mode, when a signal detected by the optical sensor of the display unit 7402 is detected and there is no input by a touch operation of the display unit 7402 for a certain period, the screen mode is switched from the input mode to the display mode. You may control.

The display portion 7402 can function as an image sensor. For example, personal authentication can be performed by touching the display portion 7402 with a palm or a finger and capturing an image of a palm print, a fingerprint, or the like. In addition, if a backlight that emits near-infrared light or a sensing light source that emits near-infrared light is used for the display portion, finger veins, palm veins, and the like can be imaged.

Note that the above electronic devices can be combined with any of the structures described in this specification as appropriate.

  In addition, a light-emitting element including the organic compound of one embodiment of the present invention is preferably used for the display portion. Since the light-emitting element can have high emission efficiency, an electronic device with low power consumption can be obtained. In addition, a light-emitting element with high heat resistance can be easily obtained.

  FIG. 8 illustrates an example of a liquid crystal display device in which a light-emitting element is used for a backlight. The liquid crystal display device illustrated in FIG. 8 includes a housing 901, a liquid crystal layer 902, a backlight unit 903, and a housing 904, and the liquid crystal layer 902 is connected to a driver IC 905. A light emitting element is used for the backlight unit 903, and current is supplied from a terminal 906.

  As the light-emitting element, a light-emitting element including the organic compound of one embodiment of the present invention is preferably used. By using the light-emitting element for a backlight of a liquid crystal display device, a backlight with reduced power consumption can be obtained. In addition, a backlight having excellent heat resistance can be obtained.

  FIG. 9 illustrates an example of a table lamp which is one embodiment of the present invention. The table lamp illustrated in FIG. 9 includes a housing 2001 and a light source 2002, and a lighting device using a light-emitting element as the light source 2002 is used.

  FIG. 10 illustrates an example of an indoor lighting device 3001. For the lighting device 3001, a light-emitting element including the organic compound of one embodiment of the present invention is preferably used. Since the organic compound is a substance having a high carrier transport property, a lighting device with low power consumption can be obtained. In addition, the lighting device can have high heat resistance.

  An automobile which is one embodiment of the present invention is shown in FIG. The automobile has a light emitting element mounted on a windshield or a dashboard. Display regions 5000 to 5005 are display regions provided using light-emitting elements. As the light-emitting element, an organic compound in which a heteroaromatic group including a bipyridine skeleton is bonded to the 2-position and 8-position of dibenzofuran is preferably used. By using the organic compound, a light-emitting element with low driving voltage can be obtained. . In addition, the display area 5000 to the display area 5005 can reduce power consumption, and thus are suitable for in-vehicle use.

  A display area 5000 and a display area 5001 are display devices using light emitting elements provided on a windshield of an automobile. By manufacturing the light-emitting element using a light-transmitting electrode for the first electrode and the second electrode, a so-called see-through display device in which the opposite side can be seen can be obtained. If it is a see-through display, it can be installed without obstructing the field of view even if it is installed on the windshield of an automobile. Note that in the case where a transistor for driving or the like is provided, a light-transmitting transistor such as an organic transistor using an organic semiconductor material or a transistor using an oxide semiconductor is preferably used.

  A display region 5002 is a display device using a light emitting element provided in a pillar portion. In the display area 5002, the field of view blocked by the pillar can be complemented by projecting an image from the imaging means provided on the vehicle body. Similarly, the display area 5003 provided in the dashboard portion compensates for the blind spot by projecting an image from the imaging means provided outside the automobile from the field of view blocked by the vehicle body, thereby improving safety. Can do. By displaying the video so as to complement the invisible part, it is possible to check the safety more naturally and without a sense of incongruity.

  The display area 5004 and the display area 5005 can provide various other information such as navigation information, a speedometer, a rotation speed, a travel distance, an oil supply amount, a gear state, and an air conditioning setting. The display items and layout can be appropriately changed according to the user's preference. Note that these pieces of information can also be provided in the display area 5000 to the display area 5003. In addition, the display region 5000 to the display region 5005 can be used as a lighting device.

  12A and 12B illustrate an example of a tablet terminal that can be folded. In FIG. FIG. 12A illustrates an open state in which the tablet terminal includes a housing 9630, a display portion 9631a, a display portion 9631b, a display mode switching switch 9034, a power switch 9035, a power saving mode switching switch 9036, and a fastener 9033. And an operation switch 9038. Note that the tablet terminal is manufactured using the light-emitting device including the light-emitting element including the organic compound of one embodiment of the present invention for one or both of the display portion 9631a and the display portion 9631b.

  Part of the display portion 9631 a can be a touch panel region 9632 a and data can be input when a displayed operation key 9637 is touched. Note that in the display portion 9631a, for example, a structure in which half of the regions have a display-only function and a structure in which the other half has a touch panel function is shown, but the structure is not limited thereto. The entire region of the display portion 9631a may have a touch panel function. For example, the entire surface of the display portion 9631a can display keyboard buttons to serve as a touch panel, and the display portion 9631b can be used as a display screen.

  Further, in the display portion 9631b as well, like the display portion 9631a, part of the display portion 9631b can be a touch panel region 9632b. In addition, a keyboard button can be displayed on the display portion 9631b by touching a position where the keyboard display switching button 9639 on the touch panel is displayed with a finger, a stylus, or the like.

  Further, touch input can be performed on the touch panel region 9632a and the touch panel region 9632b at the same time.

  A display mode switching switch 9034 can switch the display direction such as vertical display or horizontal display, and can select switching between monochrome display and color display. The power saving mode change-over switch 9036 can optimize the display luminance in accordance with the amount of external light during use detected by an optical sensor built in the tablet terminal. The tablet terminal may include not only an optical sensor but also other detection devices such as a gyroscope, an acceleration sensor, and other sensors that detect inclination.

  FIG. 12A illustrates an example in which the display areas of the display portion 9631b and the display portion 9631a are the same, but there is no particular limitation, and one size may be different from the other size, and the display quality is also high. May be different. For example, one display panel may be capable of displaying images with higher definition than the other.

  FIG. 12B illustrates a closed state, in which the tablet terminal in this embodiment includes a housing 9630, a solar battery 9633, a charge / discharge control circuit 9634, a battery 9635, and a DCDC converter 9636. Note that FIG. 12B illustrates a structure including a battery 9635 and a DCDC converter 9636 as an example of the charge / discharge control circuit 9634.

  Note that since the tablet terminal can be folded in two, the housing 9630 can be closed when not in use. Accordingly, since the display portion 9631a and the display portion 9631b can be protected, a tablet terminal with excellent durability and high reliability can be provided from the viewpoint of long-term use.

  In addition, the tablet terminal shown in FIGS. 12A and 12B has a function for displaying various information (still images, moving images, text images, etc.), a calendar, a date, or a time. A function for displaying on the display unit, a touch input function for performing touch input operation or editing of information displayed on the display unit, a function for controlling processing by various software (programs), and the like can be provided.

  Electric power can be supplied to the touch panel, the display unit, the video signal processing unit, or the like by the solar battery 9633 mounted on the surface of the tablet terminal. Note that it is preferable that the solar battery 9633 be provided on one or two surfaces of the housing 9630 because the battery 9635 can be efficiently charged.

  The structure and operation of the charge / discharge control circuit 9634 illustrated in FIG. 12B are described with reference to a block diagram in FIG. FIG. 12C illustrates a solar cell 9633, a battery 9635, a DCDC converter 9636, a converter 9638, switches SW1 to SW3, and a display portion 9631. The battery 9635, the DCDC converter 9636, the converter 9638, and the switches SW1 to SW3 are illustrated. This corresponds to the charge / discharge control circuit 9634 shown in FIG.

  First, an example of operation in the case where power is generated by the solar battery 9633 using external light is described. The power generated by the solar battery is boosted or lowered by the DCDC converter 9636 so as to be a voltage for charging the battery 9635. When the power charged in the solar battery 9633 is used for the operation of the display portion 9631, the switch SW1 is turned on, and the converter 9638 increases or decreases the voltage required for the display portion 9631. In the case where display on the display portion 9631 is not performed, the battery 9635 may be charged by turning off SW1 and turning on SW2.

  Note that although the solar cell 9633 is shown as an example of the power generation unit, the power generation unit is not particularly limited, and the battery 9635 is charged by another power generation unit such as a piezoelectric element (piezo element) or a thermoelectric conversion element (Peltier element). The structure which performs this may be sufficient. A non-contact power transmission module that wirelessly (contactlessly) transmits and receives power for charging and a combination of other charging means may be used, and the power generation means may not be provided.

  Note that the organic compound of one embodiment of the present invention can be used for an organic thin film solar cell. More specifically, since it has carrier transportability, it can be used for a carrier transport layer. Further, since it is optically excited, it can be used as a power generation layer.

  Further, as long as the display portion 9631 is included, the tablet terminal is not limited to the shape illustrated in FIG.

  In this example, 3- {dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″-(9H) fluorene] 9 ′ which is an organic compound of one embodiment of the present invention is used. A method for synthesizing -yl} pyridine (abbreviation: 2PyDfha) will be described in detail.

In a 200 mL three-necked flask, 2.00 g (3.57 mmol) of 2′-bromo-dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″-(9H) fluorene], 3- 483 mg (3.93 mmol) of pyridineboronic acid was added and the atmosphere was replaced with nitrogen. To this, 36 mL of toluene, 3.6 mL of ethanol, 3.93 mL (7.86 mmol) of 2M potassium carbonate aqueous solution were added and deaerated. 82.6 mg (71.5 μmol) of tetrakistriphenylphosphine palladium was added and stirred at 85 degrees for 6 hours. To this, 82.6 mg (71.5 μmol) of tetrakistriphenylphosphine palladium was added and further stirred at 85 ° C. for 15 hours.
After completion of the reaction, toluene was added thereto and filtered through celite. Water was added to the filtrate and extracted with toluene, and the resulting organic layer was washed with saturated brine, and magnesium sulfate was added to adsorb moisture. The organic layer to which moisture was adsorbed was naturally filtered, and the filtrate was concentrated to obtain a yellow solid. The resulting yellow solid was purified by silica gel column chromatography (developing solvent: toluene and a mixture of toluene and ethyl acetate) to obtain a white solid. Methanol was added to the obtained solid, ultrasonic waves were applied, and the resulting suspension was subjected to suction filtration to obtain a residue. The obtained filtrate was dried to obtain 856 mg of a white solid with a yield of 43.0%. A synthesis scheme (a-1) is shown below.

¹ H NMR of the obtained substance was measured. The measurement data is shown below.

¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 6.40-6.43 (m, 2H), 6.50 (d, J = 8.1 Hz, 1H), 6.57 (d, J = 1.8 Hz, 1H), 6.79-6.83 (m, 2H), 7.00 (dd, J = 1.8 Hz, 8.1 Hz, 1H), 7.10-7.14 (m, 1H), 7.26-7.48 (m, 13H), 7.92-7.96 (m, 4H), 8.34 (d, J = 2.1 Hz, 1H), 8.39 (dd, J = 1.5Hz, 5.1Hz, 1H)

A ¹ H-NMR chart is shown in FIG. Note that FIG. 13B is a chart in which the range of 6 ppm to 9 ppm in FIG. Thus, it was found that 2PyDfha, which is an organic compound of one embodiment of the present invention represented by the above structural formula (100), was obtained.

  In addition, 2PyDfha was analyzed by liquid chromatography mass spectrometry (abbreviation: LC / MS analysis). The LC / MS analysis was performed using Waters Acquity UPLC and Waters Xevo G2 Tof MS.

  In the MS analysis, ionization by electrospray ionization (abbreviation: ESI) was performed. At this time, the capillary voltage was 3.0 kV, the sample cone voltage was 30 V, and the detection was performed in the positive mode. Further, the components ionized under the above conditions collided with argon gas in the collision chamber (collision cell) to dissociate into product ions. The energy (collision energy) for collision with argon was 70 eV. The mass range to be measured was m / z = 100 to 1200.

  The measurement results are shown in FIG. From the results in FIG. 14, it was found that 2PyDfha mainly detects product ions in the vicinity of m / z = 326, m / z = 402, and m / z = 558. In addition, since the result shown in FIG. 14 shows the characteristic result derived from 2PyDfha, it can be said that it is important data in identifying 2PyDfha contained in the mixture.

  Next, an ultraviolet-visible absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and an emission spectrum of a 2PyDfha toluene solution and a solid thin film were measured. The solid thin film was formed on a quartz substrate by a vacuum deposition method. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used. In addition, a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum.

  As a result, a 2PyDfha toluene solution showed an absorption peak around 310 nm, and the thin film showed an absorption peak around 312 nm. Further, the emission wavelength peaks of the toluene solution were 323 nm and 313 nm, and the emission wavelength peaks of the thin film were 300 nm and 316 nm, indicating that ultraviolet emission was exhibited.

  Further, the ionization potential value of 2PyDfha in a thin film state was measured in the atmosphere by photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-3). As a result of converting the obtained ionization potential value to a negative value, the HOMO level of 2PyDfha was −6.54 eV. From the absorption spectrum data of the thin film, the absorption edge of 2PyDfha determined from Tauc plot assuming direct transition was 3.89 eV. Therefore, the optical energy gap in the solid state of 2PyDfha is estimated to be 3.89 eV, and the LUMO level of 2PyDfha can be estimated to be −2.65 eV from the HOMO level obtained earlier and the value of this energy gap. it can. Thus, 2PyDfha has a relatively deep HOMO level and LUMO level in the solid state, and has a wide energy gap of 3.89 eV.

  In this example, 5- {dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″-(9H) fluorene] 9 ′ which is an organic compound of one embodiment of the present invention is used. A method for synthesizing -yl} pyrimidine (abbreviation: 2PmDfha) will be described in detail.

In a 200 mL three-necked flask, 572 mg (3.60 mmol) of 5-bromopyrimidine, dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″-(9H) fluorene] -2′- 1.89 mg (3.60 mmol) of boronic acid and 43.8 mg (144 μmol) of tris (2-methylphenyl) phosphine were added and purged with nitrogen. Toluene 36 mL, ethanol 3.6 mL, 2M potassium carbonate aqueous solution 3.6 mL (7.20 mmol) was added thereto, and the mixture was deaerated by stirring under reduced pressure. The mixture was stirred at 85 ° C. for 21.5 hours, during which time 48.6 mg (0.22 mmol) of palladium acetate was divided into three portions, and 87.6 mg (0.28 mmol) of tris (2-methylphenyl) phosphine was added. Added in two portions.
After completion of the reaction, toluene was added to the mixture and heated, followed by filtration through celite. Water was added to the filtrate, extracted with toluene, the organic layer was washed with saturated brine, and magnesium sulfate was added to adsorb moisture. The organic phase to which moisture was adsorbed was naturally filtered to remove magnesium sulfate, and the solvent was removed to obtain a yellow solid. The resulting yellow solid was purified by silica gel column chromatography (developing solvent: toluene and a mixture of toluene and ethyl acetate) to obtain a white solid. Methanol was added to the obtained white solid, ultrasonic waves were applied, and the resulting suspension was subjected to suction filtration to obtain 762 mg of the objective white solid in a yield of 38.0%. A synthesis scheme (a-2) is shown below.

¹ H NMR of the obtained substance was measured. The measurement data is shown below.
¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 6.39-6.45 (m, 2H), 6.53-6.56 (m, 2H), 6.78-6.84 (m , 2H), 6.99 (dd, J = 1.8 Hz, 8.1 Hz, 1H), 7.26-7.36 (m, 8H), 7.43-7.49 (m, 4H), 7 .94 (dd, J = 2.4 Hz, 7.2 Hz, 4H), 8.45 (s, 2H), 9.00 (s, 1H).

Further, the ¹ H-NMR chart is shown in FIG. Note that FIG. 15B is a chart in which the range of 6 ppm to 9.5 ppm in FIG. Thus, it was found that 2PmDfha, which is an organic compound of one embodiment of the present invention represented by the above structural formula (103), was obtained.

  Further, 2PmDfha was analyzed by liquid chromatograph mass spectrometry (abbreviation: LC / MS analysis). The LC / MS analysis was performed using Waters Acquity UPLC and Waters Xevo G2 Tof MS.

  In the MS analysis, ionization by electrospray ionization (abbreviation: ESI) was performed. At this time, the capillary voltage was 3.0 kV, the sample cone voltage was 30 V, and the detection was performed in the positive mode. Further, the components ionized under the above conditions collided with argon gas in the collision chamber (collision cell) to dissociate into product ions. The energy (collision energy) for collision with argon was 70 eV. The mass range to be measured was m / z = 100 to 1200.

  The measurement results are shown in FIG. From the results of FIG. 16, it was found that 2PmDfha mainly detects product ions in the vicinity of m / z = 165, m / z = 326, m / z = 404, and m / z = 559. In addition, since the result shown in FIG. 16 shows the characteristic result derived from 2PmDfha, it can be said that it is important data in identifying 2PmDfha contained in the mixture.

  Next, an ultraviolet-visible absorption spectrum (hereinafter simply referred to as “absorption spectrum”) and an emission spectrum of a solid thin film of 2PmDfha were measured. The solid thin film was formed on a quartz substrate by a vacuum deposition method. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used. In addition, a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum.

  As a result, the 2PmDfha thin film had an absorption peak at around 312 nm. Further, the peak of the emission wavelength was 390 nm, and it was found that ultraviolet emission was exhibited.

The phosphorescence spectrum of 2PmDfha was measured by the low temperature PL method. For the measurement, a micro-PL device LabRAM HR-PL (Horiba, Ltd.) was used, the measurement temperature was 10K, a He-Cd laser (325 nm) was used as excitation light, and a CCD detector was used as the detector. The thin film was formed on a quartz substrate with a thickness of 30 nm, and another quartz substrate was attached to the quartz substrate in a nitrogen atmosphere from the vapor deposition surface side, and then used for measurement. As a result, it was found that 2PmDfha has a phosphorescence peak at 443 nm and has a sufficient T1 level as a host material of a blue phosphorescence material.

  Further, the ionization potential value of 2PmDfha in a thin film state was measured in the atmosphere by photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-3). As a result of converting the obtained ionization potential value to a negative value, the HOMO level of 2PmDfha was −6.59 eV. From the absorption spectrum data of the thin film, the absorption edge of 2PmDfha obtained from Tauc plot assuming direct transition was 3.89 eV. Therefore, the optical energy gap in the solid state of 2PmDfha is estimated to be 3.89 eV, and the LUMO level of 2PmDfha can be estimated to be −2.70 eV from the HOMO level obtained earlier and the value of this energy gap. it can. Thus, it was found that 2PmDfha has a relatively deep HOMO level and LUMO level in the solid state and a wide energy gap of 3.89 eV.

In addition, electrochemical characteristics (oxidation reaction characteristics, reduction reaction characteristics) in a 2PmDfha solution were measured by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used.

  In the measurement, the potential of the working electrode with respect to the reference electrode was changed within an appropriate range to obtain an oxidation peak potential and a reduction peak potential, respectively. From the obtained peak potential, the LUMO level of 2PmDfha was calculated to be -2.41 eV, and it was shown from the CV measurement that it has a relatively deep LUMO level.

  In this example, 2- {dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″-(9H) fluorene] 9 ′ which is an organic compound of one embodiment of the present invention is used. A method for synthesizing -yl} dibenzo [f, h] quinoxaline (abbreviation: 2DBqDfha) will be described in detail.

In a 200 mL three-necked flask, 1.20 g (4.52 mmol) of 2-chlorodibenzo [f, h] quinoxaline, dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″-(9H ) Fluorene] -2′-boronic acid 2.61 g (4.98 mmol) was added and the atmosphere was replaced with nitrogen. 50 mL of toluene, 5.0 mL of ethanol, 2.98 mL (9.95 mmol) of 2M aqueous potassium carbonate solution were added, and the mixture was deaerated by stirring under reduced pressure. 115 mg (99.5 μmol) of tetrakis (triphenylphosphine) palladium (0) was added and stirred at 80 ° C. for 6 hours under a nitrogen stream. 115 mg (99.5 μmol) of tetrakis (triphenylphosphine) palladium (0) was added and further stirred at 80 ° C. for 14 hours under a nitrogen stream.
After heating for a predetermined time, water was added and extracted with toluene, and the organic layer was washed with saturated brine. The solid in the organic layer was collected by suction filtration, heated with toluene added. After cooling, a green solid was obtained by suction filtration. The obtained solid was purified by silica gel column chromatography (developing solvent: chloroform) to obtain a green solid. Methanol was added to the obtained solid and suspended by irradiating ultrasonic waves, and the suspension was subjected to suction filtration to obtain a residue. Further, the obtained filtrate was dried to obtain 1.88 g of the objective green solid in a yield of 58.6%. A synthesis scheme (a-3) is shown below.

¹ H NMR of the obtained substance was measured. The measurement data is shown below.
¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 6.45-6.51 (m, 2H), 6.63 (d, J = 8.1 Hz, 1H), 6.83-6.86 (M, 2H), 7.27 (d, J = 1.5 Hz, 1H), 7.31-7.37 (m, 8H), 7.44-7.51 (m, 4H), 7.61 −7.75 (m, 4H), 7.79 (dd, J = 1.2 Hz, 8.1 Hz, 1H), 7.96-8.02 (m, 4H), 8.53-8.56 ( m, 2H), 8.79 (s, 1H), 8.95-9.05 (m, 2H)

Further, the ¹ H-NMR chart is shown in FIG. Note that FIG. 17B is a chart in which the range of 6 ppm to 9.5 ppm in FIG. Thus, it was found that 2DBqDfha, which is an organic compound of one embodiment of the present invention represented by the above structural formula (107), was obtained.

  In addition, 2DBqDfha was analyzed by liquid chromatography mass spectrometry (abbreviation: LC / MS analysis). The LC / MS analysis was performed using Waters Acquity UPLC and Waters Xevo G2 Tof MS.

  In the MS analysis, ionization by electrospray ionization (abbreviation: ESI) was performed. At this time, the capillary voltage was 3.0 kV, the sample cone voltage was 30 V, and the detection was performed in the positive mode. Further, the components ionized under the above conditions collided with argon gas in the collision chamber (collision cell) to dissociate into product ions. The energy (collision energy) for collision with argon was 70 eV. The mass range to be measured was m / z = 100 to 1200.

  The measurement results are shown in FIG. From the results of FIG. 18, it was found that 2DBqDfha mainly detects product ions in the vicinity of m / z = 177, m / z = 229, m / z = 402, and 709 nm. Note that the results shown in FIG. 18 show characteristic results derived from 2DBqDfha, and thus can be said to be important data for identifying 2DBqDfha contained in the mixture.

  Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as “absorption spectrum”) and an emission spectrum of a solid thin film of 2DBqDfha were measured. The solid thin film was formed on a quartz substrate by a vacuum deposition method. For the measurement of the absorption spectrum, an ultraviolet-visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used. In addition, a fluorometer (FS920 manufactured by Hamamatsu Photonics Co., Ltd.) was used for measuring the emission spectrum.

  As a result, an absorption peak was observed at around 376 nm in the toluene solution of 2DBqDfha. Moreover, the peak of the light emission wavelength was 387 nm and 408 nm, and it turned out that ultraviolet light emission is shown.

In addition, electrochemical characteristics (oxidation reaction characteristics, reduction reaction characteristics) in a solution of 2DBqDfha were measured by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A or 600C) was used.

  In the measurement, the potential of the working electrode with respect to the reference electrode was changed within an appropriate range to obtain an oxidation peak potential and a reduction peak potential, respectively. From the obtained peak potential, the LUMO level of 2DBqDfha was calculated to be -2.93 eV, indicating that it has a relatively deep LUMO level.

In this example, a light-emitting element (light-emitting element 1, light-emitting element 2) of one embodiment of the present invention will be described. Structural formulas of organic compounds used in the light-emitting element 1 and the light-emitting element 2 are shown below.

(Method for Manufacturing Light-Emitting Element 1)
First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, so that the first electrode 101 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm. Here, the first electrode 101 is an electrode that functions as an anode of the light-emitting element.

Next, as a pretreatment for forming a light-emitting element over the substrate, the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

Thereafter, the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁻⁴ Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus so that the surface on which the first electrode 101 is formed is downward, and is approximately 10 ⁻⁴ Pa. After the pressure is reduced to 4,4 ′, 4 ″-(benzene-1,3,5-triyl represented by the above structural formula (i) on the first electrode 101 by an evaporation method using resistance heating. ) Tri (dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide (VI) were co-evaporated to form the hole injection layer 111. The film thickness was 60 nm, and the weight ratio of DBT3P-II and molybdenum oxide was adjusted to 4: 2 (= DBT3P-II: molybdenum oxide). Note that the co-evaporation method is an evaporation method in which evaporation is performed simultaneously from a plurality of evaporation sources in one processing chamber.

Next, 3,3′-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP) represented by the above structural formula (ii) is formed over the hole injection layer 111 so as to have a thickness of 20 nm. A hole transport layer 112 was formed by film formation.

Further, on the hole transport layer 112, PCCP and 3- {dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″ represented by the above structural formula (iii) -(9H) fluorene] 9'-yl} pyridine (abbreviation: 2PyDfha) (abbreviation: 2PyDfha) and tris {2- [5- (2-methylphenyl) -4- represented by the above structural formula (iv) (2,6-diisopropylphenyl) -4H-1,2,4-triazol-3-yl-κN2] phenyl-κC} iridium (III) (abbreviation: [Ir (mppptz-diPrp) ₃ ]) Co-deposited with a thickness of 30 nm so that the ratio was 1: 0.3: 0.06 (= PCCP: 2PyDfha: [Ir (mppptz-diPrp) ₃ ]), and then 2PyDfha and [Ir (mppptz-diP rp) ₃ ] was co-evaporated to a weight ratio of 1: 0.06 (= 2PyDfha: [Ir (mppptz-diPrp) ₃ ]) to form a light-emitting layer 113.

Subsequently, 3,5-bis [3- (9H-carbazol-9-yl) phenyl] pyridine (abbreviation: 35DCzPPy) represented by the above structural formula (v) is formed on the light-emitting layer 113 so as to have a thickness of 10 nm. Further, bathophenanthroline (abbreviation: Bphen) represented by the structural formula (vi) was formed to a thickness of 15 nm to form the electron transport layer 114.

After the electron transport layer 114 is formed, lithium fluoride (LiF) is then deposited to a thickness of 1 nm to form the electron injection layer 115, and finally, as the second electrode 102 that functions as a cathode, The light emitting element 1 of this example was manufactured by vapor-depositing aluminum so as to have a thickness of 200 nm.

(Method for Manufacturing Light-Emitting Element 2)
The light emitting element 2 was produced in the same manner as the light emitting element 1 except that the light emitting layer 113 in the light emitting element 1 was formed as follows.
In the light-emitting element 2, PCCP, 2PyDfha, and [Ir (mppptz-diPrp) ₃ ] are placed on the hole transport layer 112 in a weight ratio of 1: 0.3: 0.06 (= PCCP: 2PyDfha: [Ir (Mpppz-diPrp) ₃ ]) is co-deposited to 30 nm, and then 35DCzPPy and [Ir (mpppz-diPrp) ₃ ] are in a weight ratio of 1: 0.06 (= 35DCzPPy: [Ir (mppptz-diPrp)). ₃ ]), the light emitting layer 113 was formed by co-evaporation with a thickness of 30 nm.

The operation of sealing the light-emitting element 1 and the light-emitting element 2 with a glass substrate in a glove box in a nitrogen atmosphere so that the light-emitting element is not exposed to the atmosphere (a sealing material is applied around the element and UV treatment is performed during sealing, After heat treatment at 80 ° C. for 1 hour, reliability was measured. The measurement was performed at room temperature (atmosphere kept at 25 ° C.).

The luminance-current efficiency characteristics of the light-emitting element 1 and the light-emitting element 2 are shown in FIG. 19, the luminance-external quantum efficiency characteristic is shown in FIG. 20, the emission spectrum is shown in FIG. 21, and the luminance-chromaticity characteristic chart 22 is shown.

  From the above results, it was found that the light-emitting element 1 and the light-emitting element 2 exhibit very good characteristics. Since 2PyDfha has a high triplet excitation energy, it can excite and emit a phosphorescent compound that emits light blue light in particular, so that it has good luminous efficiency and excellent current efficiency and external efficiency. showed that. Further, there was almost no change in luminance accompanying the change in luminance, and a light-emitting element with a good carrier balance could be obtained. Therefore, it was found that 2PyDfha can be suitably used for the light emitting layer of the blue phosphorescent element.

In this example, a light-emitting element (light-emitting element 3 to light-emitting element 5) of one embodiment of the present invention will be described. Structural formulas of organic compounds used in the light-emitting elements 3 to 5 are shown below.

(Method for Manufacturing Light-Emitting Element 3)
First, indium tin oxide containing silicon oxide (ITSO) was formed over a glass substrate by a sputtering method, so that the first electrode 101 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm. Here, the first electrode 101 is an electrode that functions as an anode of the light-emitting element.

Next, as a pretreatment for forming a light-emitting element over the substrate, the surface of the substrate was washed with water, baked at 200 ° C. for 1 hour, and then subjected to UV ozone treatment for 370 seconds.

Thereafter, the substrate is introduced into a vacuum vapor deposition apparatus whose internal pressure is reduced to about 10 ⁻⁴ Pa, vacuum baking is performed at 170 ° C. for 30 minutes in a heating chamber in the vacuum vapor deposition apparatus, and then the substrate is released for about 30 minutes. Chilled.

Next, the substrate on which the first electrode 101 is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus so that the surface on which the first electrode 101 is formed is downward, and is approximately 10 ⁻⁴ Pa. After the pressure is reduced to 4,4 ′, 4 ″-(benzene-1,3,5-triyl represented by the above structural formula (i) on the first electrode 101 by an evaporation method using resistance heating. ) Tri (dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide (VI) were co-evaporated to form the hole injection layer 111. The film thickness was 60 nm, and the weight ratio of DBT3P-II and molybdenum oxide was adjusted to 4: 2 (= DBT3P-II: molybdenum oxide). Note that the co-evaporation method is an evaporation method in which evaporation is performed simultaneously from a plurality of evaporation sources in one processing chamber.

Next, 3,3′-bis (9-phenyl-9H-carbazole) (abbreviation: PCCP) represented by the above structural formula (ii) is formed over the hole injection layer 111 so as to have a thickness of 20 nm. A hole transport layer 112 was formed by film formation.

Further, on the hole transport layer 112, PCCP and 3- {dispiro [9H-fluorene-9,9 ′ (10′H) -anthracene-10 ′, 9 ″ represented by the above structural formula (vii) -(9H) fluorene] 9'-yl} pyrimidine (abbreviation: 2PmDfha) and tris {2- [5- (2-methylphenyl) -4- (2,6-) represented by the above structural formula (iv) Diisopropylphenyl) -4H-1,2,4-triazol-3-yl-κN2] phenyl-κC} iridium (III) (abbreviation: [Ir (mpppz-diPrp) ₃ ]) in a weight ratio of 1: 0. 3: 0.06 (= PCCP: 2PmDfha : [Ir (mpptz-diPrp) 3]) become as deposited 30nm co, then, 2PmDfha and _{[Ir (mpptz-diPrp) 3} ] and the weight ratio of : 0.06: was (= 2PmDfha [Ir (mpptz- diPrp) 3]) and so as to be deposited 30nm co to form a light-emitting layer 113.

Subsequently, 2PmDfha is formed to a thickness of 10 nm over the light-emitting layer 113, and further, bathophenanthroline (abbreviation: Bphen) represented by the structural formula (vi) is formed to a thickness of 15 nm. An electron transport layer 114 was formed.

After the electron transport layer 114 is formed, lithium fluoride (LiF) is then deposited to a thickness of 1 nm to form the electron injection layer 115, and finally, as the second electrode 102 that functions as a cathode, The light emitting element 1 of this example was manufactured by vapor-depositing aluminum so as to have a thickness of 200 nm.

(Method for Manufacturing Light-Emitting Element 4)
The light emitting device 4 was produced in the same manner as the light emitting device 3 except that the electron transport layer in the light emitting device 3 was formed as follows. In the light-emitting element 4, 3,5-bis [3- (9H-carbazol-9-yl) phenyl] pyridine (abbreviation: 35DCzPPy) represented by the above structural formula (v) is formed on the light-emitting layer 113 with a thickness of 10 nm. Then, an electron transport layer 114 was formed by depositing bathophenanthroline (abbreviation: Bphen) represented by the structural formula (vi) so as to have a thickness of 15 nm.

(Method for Manufacturing Light-Emitting Element 5)
The light emitting element 5 was produced in the same manner as the light emitting element 4 except that the light emitting layer in the light emitting element 4 was formed as follows. In the light-emitting element 5, PCCP, 2PmDfha, and [Ir (mppptz-diPrp) ₃ ] are placed on the hole transport layer 112 in a weight ratio of 1: 0.3: 0.06 (= PCCP: 2PmDfha: [Ir ( mpppz-diPrp) ₃ ]) to be 30 nm co-evaporated, and then 35DCzPPy and [Ir (mpppz-diPrp) ₃ ] are in a weight ratio of 1: 0.06 (= 35DCzPPy: [Ir (mpppz-diPrp) ₃ ] To form a light emitting layer 113 by co-evaporation to 30 nm.

The operation of sealing the light-emitting elements 3 to 5 and the light-emitting elements 5 with a glass substrate in a glove box in a nitrogen atmosphere so that the light-emitting elements are not exposed to the atmosphere (a sealing material is applied around the elements and UV treatment is performed at the time of sealing) , Heat treatment at 80 ° C. for 1 hour), and then reliability was measured. The measurement was performed at room temperature (atmosphere kept at 25 ° C.).

FIG. 23 shows luminance-current efficiency characteristics of the light-emitting elements 3 to 5, FIG. 24 shows luminance-external quantum efficiency characteristics, FIG. 25 shows an emission spectrum, and FIG. 26 shows luminance-chromaticity characteristics.

  From the above results, it was found that the light-emitting elements 3 to 5 have very good characteristics. Since 2PmDfha has a high triplet excitation energy, it can excite and emit phosphorescent compounds that exhibit light-blue emission in particular, so that it has good luminous efficiency and excellent current efficiency and external efficiency. showed that. Further, there was almost no change in luminance accompanying the change in luminance, and a light-emitting element with a good carrier balance could be obtained. Therefore, it was found that 2PyDfha can be suitably used for the light emitting layer and the electron transport layer of the blue phosphorescent device.

In this example, the organic compound (100), the compound (103), the compound (106), the compound (112), and the compound (118) which are one embodiment of the present invention shown as the general formula (G1) in Embodiment 1 The band gap (ΔE) between the HOMO level, LUMO level, HOMO-LUMO level, and T1 level of the anthracene compound of Compound (107) were calculated. As a comparison, the calculation was also performed for the comparative compound (R01). These structural formulas are shown below.

A high performance computer (manufactured by SGI, Altix 4700) was used for the calculation, and Gaussian 09 was used as the quantum chemistry calculation program. The calculation method is as follows.

First, the most stable structure in a singlet was calculated by the density functional method. As a basis function, 6-311 (a basis function of a triple split valence basis set using three shortening functions for each valence orbital) was applied to all atoms. According to the above basis function, for example, for hydrogen atoms, orbits of 1s to 3s are considered, and for carbon atoms, orbits of 1s to 4s and 2p to 4p are considered. Furthermore, in order to improve calculation accuracy, a p function was added to hydrogen atoms and a d function was added to other than hydrogen atoms as a polarization basis set. The functional was B3LYP. In addition, the LUMO and HOMO of the structure were respectively calculated.

Subsequently, the most stable structure in the triplet was calculated. The energy of the T1 level was calculated from the energy difference of the most stable structure in the singlet and triplet. As the basis function, 6-311G (d, p) was used. The functional is B3LYP.

The calculated results are shown in Table 3.

From the above results, it was found that these organic compounds have relatively deep HOMO levels and LUMO levels. In particular, it was found that the compound (118) and the compound (107) having a condensed aromatic substituent in the electron transport unit have a deep LUMO level and are more suitable as an electron transport material. It was found that the band gap (ΔE) between the HOMO-LUMO levels was as wide as 3 eV or more.

Further, these anthracene compounds were found to have a high T1 level. The compound (100), compound (103), compound (106), and compound (112) having a monocyclic aromatic substituent in the electron transport unit have a particularly high T1 level and are adjacent to the light emitting layer of the blue phosphorescent device It was found to be suitable for the electron transport layer. It was found that the compound (118) and the compound (107) having a condensed aromatic substituent in the electron transport unit can be applied to a green phosphorescent device.

Thus, the reason why the organic compound which is one embodiment of the present invention has a high T1 level is considered to be due to the spin density distribution of T1. FIG. 27 shows the result of calculating the spin density distribution by the above method.

As shown in FIG. 27, it was found that the spin almost spread only from the electron transport unit to the benzene skeleton at the 2-position in the anthracene skeleton to which it was bonded. This is presumably because the 9th and 10th positions of anthracene are sigma carbon, and fluorene is twisted and bonded to the anthracene skeleton at 90 °. Therefore, it was found that a high T1 level close to the T1 level of (R01), which is a substance in which phenyl is bonded to the electron transport unit, can be obtained. From Table 3, the T1 level of the compound (103) and the comparative compound (R01) was only 440 nm (2.82 eV), 431 nm (2.88 eV), and only 0.06 eV. Therefore, the organic compound which is one embodiment of the present invention has a high T1 even when the molecular weight is large, suggesting that the thermophysical property is good.

Note that the glass transition point (Tg) of a compound in which a tertiary butyl group is bonded to the 2′-position of the Dfha skeleton represented by the following structural formula (R02) is 151 ° C. Therefore, the anthracene compound of one embodiment of the present invention in which an aryl group is bonded to the 2 ′ position of the Dfha skeleton is suggested to have a Tg higher than that.

101 first electrode 102 second electrode 103 EL layer 111 hole injection layer 112 hole transport layer 113 light emitting layer 114 electron transport layer 115 electron injection layer 400 substrate 401 first electrode 403 EL layer 404 second electrode 405 Seal material 406 Seal material 407 Seal substrate 412 Pad 420 IC chip 501 First electrode 502 Second electrode 503 EL layer 511 First light-emitting unit 512 Second light-emitting unit 513 Charge generation layer 601 Drive circuit portion (source line) Drive circuit)
602 Pixel portion 603 Drive circuit portion (gate line drive circuit)
604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (flexible printed circuit)
610 Element substrate 611 FET for switching
612 FET for current control
613 First electrode 614 Insulator 616 EL layer 617 Second electrode 618 Light-emitting element 623 n-channel FET
624 p-channel FET
625 Drying material 901 Case 902 Liquid crystal layer 903 Backlight unit 904 Case 905 Driver IC
906 terminal 951 substrate 952 electrode 953 insulating layer 954 partition layer 955 EL layer 956 electrode 1001 substrate 1002 base insulating film 1003 gate insulating film 1006 gate electrode 1007 gate electrode 1008 gate electrode 1020 first interlayer insulating film 1021 second interlayer insulating film 1022 Electrode 1024W First electrode 1024R of light emitting element First electrode 1024G of light emitting element First electrode 1024B of light emitting element First electrode 1025 of light emitting element Partition 1028 EL layer 1029 Second electrode 1031 of light emitting element Sealing Substrate 1032 Sealing material 1033 Transparent base material 1034R Red colored layer 1034G Green colored layer 1034B Blue colored layer 1035 Black layer (black matrix)
1037 Third interlayer insulating film 1040 Pixel portion 1041 Drive circuit portion 1042 Peripheral portion 2001 Case 2002 Light source 3001 Illumination device 5000 Display region 5001 Display region 5002 Display region 5003 Display region 5004 Display region 5005 Display region 7101 Housing 7103 Display unit 7105 Stand 7107 Display unit 7109 Operation key 7110 Remote control device 7201 Main body 7202 Case 7203 Display unit 7204 Keyboard 7205 External connection port 7206 Pointing device 7210 Second display unit 7301 Case 7302 Case 7303 Connection unit 7304 Display unit 7305 Display unit 7306 Speaker unit 7307 Recording medium insertion unit 7308 LED lamp 7309 Operation key 7310 Connection terminal 7311 Sensor 7401 Housing 7402 Display unit 7403 Operation button Tan 7404 External connection port 7405 Speaker 7406 Microphone 9033 Fastener 9034 Switch 9035 Power switch 9036 Switch 9038 Operation switch 9630 Case 9631 Display unit 9631a Display unit 9631b Display unit 9632a Touch panel region 9632b Touch panel region 9633 Solar cell 9634 Charge / discharge control circuit 9635 Battery 9636 DCDC converter 9537 Operation key 9638 Converter 9539 Button

Claims (6)

An organic compound represented by the formula (G0).

(In the formula (G0), Dfha represents a substituted or unsubstituted dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ″-(9H) fluorene] skeleton). Het is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, and Represents either a substituted or unsubstituted dibenzoquinoxalinyl group and is bonded to position 2 of Dfha.The above dispiro [9H-fluorene-9,9 ′ (10H) -anthracene-10 ′, 9 ′ '-(9H) fluorene] skeleton, pyridyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, dibenzoquinoxalini If the group has a substituent, the substituent is an alkyl group of 1 to 6 carbon atoms, is either a phenyl group.) An organic compound represented by the formula (G1).

(In the formula (G1), Het represents a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group. Represents any one of a substituted or unsubstituted quinoxalinyl group and a substituted or unsubstituted dibenzoquinoxalinyl group, the above pyridyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, dibenzoquinoxalin group When the nyl group has a substituent, the substituent is either an alkyl group having 1 to 6 carbon atoms or a phenyl group.) An organic compound represented by any one of formulas (G2) to (G4).
An organic compound represented by any one of formula (100), formula (103) and formula (107).
  The light emitting element containing the organic compound as described in any one of Claims 1 thru | or 4. The light emitting element which contains the organic compound as described in any one of Claims 1 thru | or 4 in an electron carrying layer.