JP5140357B2 - Stilbene derivatives, light-emitting elements, display devices, electronic devices - Google Patents

Description

  The present invention relates to a light emitting material. The present invention relates to a light-emitting element including the light-emitting material. Further, the present invention relates to a display device and an electronic device having such a light emitting element.

  A light-emitting element using a light-emitting material has features such as thin and light weight, high-speed response, and direct-current low-voltage driving, and is expected to be applied to a next-generation flat panel display. In addition, a light-emitting device in which light-emitting elements are arranged in a matrix has excellent visibility because of a wider viewing angle than a conventional liquid crystal display device.

  The light emission mechanism of the light emitting element will be described. When a voltage is applied to the light emitting layer sandwiched between the pair of electrodes, electrons injected from the cathode and holes injected from the anode recombine at the light emission center of the light emitting layer to form molecular excitons. Since the molecular excitons release light energy when returning to the ground state, light emission occurs.

  The emission wavelength of the light emitting element is determined by the band gap of the light emitting molecules contained in the light emitting element. Therefore, light-emitting elements having various emission colors can be obtained by devising the structure of the light-emitting molecules. A full-color light-emitting device can be manufactured by using a red light-emitting element, a blue light-emitting element, and a green light-emitting element.

In order to manufacture a full-color light emitting device, a red light emitting element, a green light emitting element, and a blue light emitting element are necessary. However, development of a highly reliable blue light-emitting material has been delayed compared to a red light-emitting material and a green light-emitting material. In order to solve this problem, many studies have been made on blue light-emitting elements (for example, Patent Document 1).
JP 2001-335516 A

  Patent Document 1 discloses several compounds in which an anthracene skeleton and a stilbene skeleton are combined. However, as described in Examples of these Patent Documents 1, the glass transition temperature Tg is 135 ° C. or less (Patent Document 1, paragraph 0086, Table 2, (25), (26), (33), ( 34), Tg (glass transition temperature (point)) is 130 ° C, 135 ° C, 105 ° C, 110 ° C in this order). In order to obtain a more reliable blue light-emitting material, it is necessary to develop a material with higher heat resistance.

  The present invention has been made in view of the above problems, and an object of the present invention is to provide a new material that gives blue light emission and has high heat resistance, and a light emitting element, a display device, and an electronic device using the same. To do.

  The material of the present invention is a stilbene derivative represented by the following general formula (1). However, in the formula, X and Y are substituents represented by the following general formula (2) or the following general formula (3), and X and Y may be the same or different.

  The material of the present invention is a stilbene derivative represented by the following general formula (1). However, in the formula, X and Y are substituents represented by the following general formula (2), and X and Y may be the same or different.

  The material of the present invention is a stilbene derivative represented by the following general formula (1). However, in the formula, X and Y are substituents represented by the following general formula (3), and X and Y may be the same or different.

  The material of the present invention is a stilbene derivative represented by the following general formula (1). However, in the formula, X is a substituent represented by the following general formula (2), and Y in the formula is a substituent represented by the following general formula (3).

  The material of the present invention is a stilbene derivative represented by the following structural formula (4).

  The light emitting device material of the present invention is characterized by containing any of the stilbene derivatives described above.

  The light-emitting element of the present invention includes an organic layer sandwiched between two electrodes, and the organic layer includes any of the above stilbene derivatives.

  A display device of the present invention includes the above-described light emitting element.

  An electronic apparatus according to the present invention includes the display device described above.

  According to the present invention, a blue light-emitting material can be provided. Further, the light emitting material of the present invention has a glass transition temperature of 40 ° C. or higher as compared with a conventional material that gives blue light emission using anthracene and stilbene. A material having a high glass transition point is a material having excellent heat resistance and excellent reliability. Therefore, according to the present invention, a blue light-emitting material that has high heat resistance (high reliability) can be provided. In addition, a light-emitting element, a display device, and an electronic device using the same can be provided.

  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. Accordingly, it will be readily understood by those skilled in the art that various changes in form and details can be made 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.

(Embodiment 1)
The stilbene derivative in the present invention is represented by the following general formula (1) or (5) to (10).

  In the above formula, X is a substituent represented by the following general formulas (2) and (3) or structural formulas (11) to (15).

  In the above formula, Y is a substituent represented by the following general formulas (2), (3), or structural formulas (11) to (15).

  X and Y may be the same or different.

  Examples of the stilbene derivatives of the present invention represented by the general formulas (1) to (13) described above include stilbene derivatives represented by the following structural formulas (16) to (112).

  In addition, the stilbene derivative of the present invention is not limited to those represented by the following structural formulas (16) to (112), but includes all those represented by the general formulas (1) to (13).

  The stilbene derivative of the present invention is characterized in that blue light emission can be obtained.

(Embodiment 2)
A method for synthesizing the stilbene derivative of the present invention represented by the general formula (1) is shown below.

[Step 1; Synthesis of Halogenated Stilbene Derivative (St1)]
First, as shown in the following synthesis scheme (A), a benzyl derivative triphenylphosphonium salt (α1) having a halogenated benzene ring and a benzaldehyde (β1) having a halogenated benzene ring are reacted in the presence of a base. To obtain a dihalogenated stilbene derivative (St1) in which each benzene ring is halogenated (so-called Wittig reaction). This dihalogenated stilbene derivative (St1) can also be obtained by using a phosphonic acid ester (α2) in place of the triphenylphosphonium salt (α1) as shown in the synthesis scheme (A ′) (so-called Horner- Emmons (Horner-Emmons reaction).

[Step 2: Synthesis of stilbene derivative of the present invention represented by the general formula (1)]
Next, as shown in the following synthesis scheme (B), by coupling a halogenated stilbene derivative (St1) and a boronic acid derivative or an organic boron compound using a metal catalyst in the presence of a base, The stilbene derivative of the present invention represented by the formula (1) can be obtained. As the metal catalyst, palladium catalysts such as palladium (II) acetate and tetrakis (triphenylphosphine) palladium (O) can be used. As the base, an inorganic salt such as potassium carbonate or sodium carbonate, or an organic base such as sodium-tert-butoxide (abbreviation: tert-BuONa) or potassium-tert-butoxide can be used. In addition, bromine or iodine is preferable as the halogen.

  In the above formula, X is a substituent represented by the following general formula (2) or (3).

  In the above formula, Y is a substituent represented by the following general formula (2) or (3).

(Embodiment 3)
In the present invention, a light-emitting element can be formed using the stilbene derivative described in Embodiment Mode 1.

  Note that the element structure of the light-emitting element in the present invention has a structure in which a layer 103 containing a light-emitting substance is sandwiched between a first electrode 101 and a second electrode 102 as shown in FIG. The layer 103 containing a light-emitting substance contains the stilbene derivative of the present invention. Here, a case where the first electrode 101 is an anode and the second electrode 102 is a cathode will be described. Note that holes are injected from the anode into the layer 103 containing a light-emitting substance, and electrons are injected from the cathode into the layer 103 containing a light-emitting substance.

  The layer 103 including a light-emitting substance has a stacked structure including at least a light-emitting layer. For example, a structure in which a hole injection layer, a light emitting layer, and an electron transport layer are sequentially stacked, a structure in which a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer are sequentially stacked, a hole injection layer, and A structure in which a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer are sequentially stacked, a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer And a stacked structure such as a structure in which are sequentially stacked.

  The light emitting device of the present invention is preferably formed on a substrate. A substrate made of glass, quartz, transparent plastic, or the like can be used.

  A known material can be used for the layer 103 containing a light-emitting substance. For example, both a low molecular compound and a high molecular compound can be used. Note that as a material for forming the layer 103 containing a light-emitting substance, not only an organic compound but also an inorganic compound may be used.

  Note that the layer 103 containing a light emitting substance includes a hole injection layer made of a hole injecting substance, a hole transport layer made of a hole transporting substance or a bipolar substance, a light emitting layer made of a light emitting substance, and a hole blocking substance. Layering layers such as a hole blocking layer (hole blocking layer) made of, an electron transporting layer made of an electron transporting material, an electron injection layer made of an electron injecting material, a first buffer layer, a second buffer layer, etc. It is formed by.

  In the present invention, when a stilbene derivative is used for the layer 103 containing a light-emitting substance, a light-emitting layer or another layer (for example, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer) The stilbene derivative of the present invention is used for any one of the first buffer layer, the second buffer layer, and the like, and the light-emitting layer and the other layers are stacked to form a light-emitting element. Specific materials used for these layers are shown below.

  Further, as the anode material of the light emitting element of the present invention, it is preferable to use a substance having a high work function (work function of 4.0 eV or more). (For example, metals, alloys, conductive compounds, or mixtures thereof). Specific examples of the anode material include ITO (indium tin oxide), IZO (indium zinc oxide) in which 2 to 20 atomic% of zinc oxide (ZnO) is mixed with indium oxide and silicon oxide, gold (Au), platinum. (Pt), titanium (Ti), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), or A nitride of a metal material or the like can be used.

  Note that a first buffer layer can be provided between the anode and the light-emitting layer, whereby the first buffer layer makes ohmic contact with various electrode materials. (For example, aluminum (Al), silver (Ag), alkali metal, alkaline earth metal, or an alloy containing these (Mg: Ag, Al: Li, etc.).

  The first buffer layer includes any one of an aromatic amine compound, a carbazole derivative, or an aromatic hydrocarbon (including an aromatic hydrocarbon including at least one vinyl skeleton) and a metal compound.

  In addition, a layer made of the stilbene derivative of the present invention and a metal compound may be used as the first buffer layer.

  Examples of aromatic amine compounds include 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), 4,4′-bis [N- (3- Methylphenyl) -N-phenylamino] biphenyl (abbreviation: TPD), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ′ '-Tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 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, N-di (m-tolyl) amino] benzene (abbreviation) : M-MTDAB 4,4 ′, 4 ″ -tri (N-carbazolyl) triphenylamine (abbreviation: TCTA), 2,3-bis (4-diphenylaminophenyl) quinoxaline (abbreviation: TPAQn), 2,2 ′, 3 , 3′-Tetrakis (4-diphenylaminophenyl) -6,6′-biquinoxaline (abbreviation: D-TriPhAQn), 2,3-bis {4- [N- (1-naphthyl) -N-phenylamino] Phenyl} dibenzo [f, h] quinoxaline (abbreviation: NPDiBzQn) and the like.

  As the carbazole derivative, for example, 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), N- (2-naphthyl) carbazole (abbreviation: NCz), 4,4′-di (N-carbazolyl) ) Biphenyl (abbreviation: CBP), 9,10-bis [4- (N-carbazolyl) phenyl] anthracene (abbreviation: BCPA), 3,5-bis [4- (N-carbazolyl) phenyl] biphenyl (abbreviation: BCPBi) ), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (abbreviation: TCPB) and the like.

  Examples of the aromatic hydrocarbon include anthracene, 9,10-diphenylanthracene (abbreviation: DPA), 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), tetracene, And rubrene, pentacene, 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), and the like.

  On the other hand, the metal compound is preferably an oxide or nitride of a transition metal. In particular, metal oxides or nitrides belonging to Groups 4 to 8 are desirable. Moreover, what has the property which is easy to receive an electron from the aromatic amine mentioned above, a carbazole derivative, and aromatic hydrocarbon (including the aromatic hydrocarbon containing at least one vinyl skeleton) is preferable. For example, metal compounds such as molybdenum oxide, vanadium oxide, ruthenium oxide, rhenium oxide, titanium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, tungsten oxide, silver oxide, etc. Can be mentioned.

  Note that in the first buffer layer, the metal compound has an aromatic amine, a carbazole derivative, or an aromatic hydrocarbon (including an aromatic hydrocarbon including at least one vinyl skeleton) and a metal in a mass ratio. It is preferably 0.5 to 2 (or preferably the molar ratio is 1 to 4). Further, since the first buffer layer has high conductivity, the thickness can be set to 50 nm or more. By setting the thickness to 50 nm or more, a short circuit between the anode and the cathode can be prevented.

On the other hand, as the cathode material, a substance having a small work function (a work function of 3.8 eV or less) can be used (a metal, an alloy, a conductive compound, or a mixture thereof can be used). Note that as the cathode material, an element belonging to Group 1 or Group 2 of the periodic table, that is, an alkali metal such as Li or Cs, an alkaline earth metal such as Mg, Ca, or Sr, or an alloy containing these (Mg: Ag Al: Li), compounds (LiF, CsF, CaF ₂ ), transition metals including rare earth metals, Al, Ag, ITO (indium tin oxide), or the like can be used.

  Note that a second buffer layer can also be provided between the cathode and the anode, whereby the second buffer layer is in ohmic contact with various electrode materials. (For example, ITO (indium tin oxide), indium tin oxide containing silicon oxide, IZO (indium zinc oxide) in which silicon oxide is included and indium oxide is mixed with 2-20 atoms% of zinc oxide (ZnO)) etc).

The second buffer layer is composed of at least one substance selected from an electron transporting substance or a bipolar substance and a substance (donor) having a property of easily releasing electrons to these substances. As the electron transporting substance or the bipolar substance, a substance having an electron mobility of 1 × 10 ⁻⁶ cm ² / Vs or more is preferable. As the electron transporting substance or the bipolar substance, materials described later can be used.

  Note that the anode material or the cathode material can form a thin film by an evaporation method, a sputtering method, or the like. The film thickness is preferably 10 to 500 nm.

  In the light-emitting element of the present invention, the light emitted from the layer 103 containing a light-emitting substance is emitted only from the anode side, the structure emitted from only the cathode side, and the structure emitted from both the anode side and the cathode side. , Can be selected. In the case of using a structure in which light is emitted from the anode side, the anode is formed of a light-transmitting material. In the case of using a configuration in which light is emitted from the cathode side, the cathode is formed of a light-transmitting material.

As the hole injection layer, a porphyrin compound can be used as long as it is an organic compound. For example, phthalocyanine (hereinafter referred to as H ₂ —Pc), copper phthalocyanine (hereinafter referred to as Cu—Pc), or the like can be used. Alternatively, a material obtained by chemically doping a conductive polymer compound can be used (for example, polyethylenedioxythiophene doped with polystyrene sulfonic acid (hereinafter referred to as PSS) (hereinafter referred to as PEDOT)).

The hole transporting layer is preferably formed using a hole transporting material or a bipolar material exhibiting a hole mobility of 1 × 10 ⁻⁶ cm ² / Vs or higher. Note that a hole transporting substance is a substance having a higher hole mobility value than an electron mobility value.

  As the hole transporting substance, an aromatic amine-based compound (that is, a compound having a benzene ring-nitrogen bond) can be used. Examples of widely used substances include 4,4′-bis [N- (3-methylphenyl) -N-phenylamino] biphenyl (hereinafter referred to as TPD), 4,4′-bis [N- ( 1-naphthyl) -N-phenylamino] biphenyl (hereinafter referred to as NPB), 4,4 ′, 4 ″ -tri (N-carbazolyl) triphenylamine (hereinafter referred to as TCTA), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (hereinafter referred to as TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] tri And phenylamine (hereinafter referred to as MTDATA).

In addition, the bipolar substance is a value obtained by dividing the value of the electron mobility and the hole mobility by the smaller value when comparing the value of the electron mobility and the value of the hole mobility. A substance whose time value is 100 or less. As a bipolar substance, for example, 2,3-bis (4-diphenylaminophenyl) quinoxaline (abbreviation: TPAQn), 2,3-bis {4- [N- (1-naphthyl) -N-phenylamino] phenyl } Dibenzo [f, h] quinoxaline (abbreviation: NPDiBzQn) and the like can be given. Among bipolar substances, it is particularly preferable to use a substance having a hole mobility value and an electron mobility value of 1 × 10 ⁻⁶ cm ² / Vs or more.

  The light emitting layer contains at least one kind of light emitting material. A light-emitting substance is a substance that has good emission efficiency and can emit light having a desired wavelength. Note that the light-emitting layer in this embodiment is a light-emitting layer using the stilbene derivative of the present invention as a host material.

  Blue light emission can be obtained by using the stilbene derivative of the present invention for the light emitting layer.

The electron transport layer is preferably formed using an electron transport material or a bipolar material that exhibits an electron mobility of 1 × 10 ⁻⁶ cm ² / Vs or higher. Note that the electron transporting substance is a substance having a higher electron mobility value than the hole mobility value, and preferably a substance having a ratio of the electron mobility to the hole mobility higher than 100. Say.

Examples of the electron transporting substance include quinoline skeletons such as tris (8-quinolinolato) aluminum (hereinafter referred to as Alq ₃ ), tris (4-methyl-8-quinolinolato) aluminum (hereinafter referred to as Almq ₃ ), and bis ( Metal complexes having a benzoquinoline skeleton such as 10-hydroxybenzo [h] quinolinato) beryllium (hereinafter referred to as BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenol) which is a mixed ligand complex Lato) aluminum (hereinafter referred to as BAlq) is preferred. Further, bis [2- (2-benzoxazolyl) phenolate] zinc (hereinafter referred to as Zn (BOX) ₂ ), bis [2- (2-hydroxyphenyl) -benzothiazolate] zinc (hereinafter referred to as Zn (BTZ)) There are also metal complexes having an oxazole-based or thiazole-based ligand such as ₂ ). In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (hereinafter referred to as PBD), 1,3-bis [ Oxadiazole derivatives such as 5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (hereinafter referred to as OXD-7), 3- (4-tert-butyl Phenyl) -4-phenyl-5- (4-biphenylyl) -1,2,4-triazole (hereinafter referred to as TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl)- Triazole derivatives such as 5- (4-biphenylyl) -1,2,4-triazole (hereinafter referred to as p-EtTAZ), bathophenanthroline (hereinafter referred to as BPhen), bathocuproin (hereinafter referred to as “p-EtTAZ”) Phenanthroline derivatives such as indicated as BCP), other 4,4-bis (5-methyl-benzoxazolyl-2-yl) stilbene (hereinafter, referred to as BzOs), or the like can be used.

  Moreover, as a hole blocking substance, BAlq, OXD-7, TAZ, p-EtTAZ, BPhen, BCP, etc. can be used.

  As described above, a blue light-emitting element can be obtained by manufacturing a light-emitting element using the stilbene derivative of the present invention for a light-emitting layer.

(Embodiment 4)
In this embodiment mode, a method for manufacturing a light-emitting device of the present invention will be described with reference to FIGS. Note that although an example in which an active matrix light-emitting device is formed is described in this embodiment mode, the present invention can also be applied to a passive matrix light-emitting device as described in Embodiment Mode 6.

  First, a first base insulating layer 51 a and a second base insulating layer 51 b are formed over the first substrate 50. Thereafter, a semiconductor layer is formed over the second base insulating layer 51b.

  As a material of the first substrate 50, glass, quartz, plastic (polyimide, acrylic, polyethylene terephthalate, polycarbonate, polyacrylate, polyethersulfone, or the like) can be used. These first substrates 50 may be used after being polished by CMP or the like, if necessary. In this embodiment mode, glass is used.

  In the first base insulating layer 51a and the second base insulating layer 51b, an element that adversely affects the characteristics of a semiconductor film such as an alkali metal or an alkaline earth metal contained in the first substrate 50 is contained in the semiconductor layer. It is provided to prevent diffusion. As a material, silicon oxide, silicon nitride, silicon oxide containing nitrogen, silicon nitride containing oxygen, or the like can be used. In the present embodiment, the first base insulating layer 51a uses silicon nitride, and the second base insulating layer 51b uses silicon oxide. In this embodiment mode, a two-layer structure of the first base insulating layer 51a and the second base insulating layer 51b is used. However, the base insulating layer may have a single-layer structure or a stacked structure including three or more layers.

  Next, a semiconductor layer is formed. In this embodiment, a silicon film is used. An amorphous silicon film is formed to a thickness of 25 to 100 nm (preferably 30 to 60 nm) over the second base insulating layer 51b. As a manufacturing method, a known method such as a sputtering method, a low pressure CVD method or a plasma CVD method can be used. Thereafter, heat treatment is performed at 500 ° C. for 1 hour, and hydrogen is extracted from the amorphous hydrogen film.

  Next, the amorphous silicon film is laser crystallized to form a crystalline silicon film. An excimer laser is used in the laser crystallization of this embodiment.

  Another crystallization method may be used as a method for crystallizing the amorphous silicon film. For example, there are a method of performing crystallization only by heat treatment, a method of performing heat treatment using a catalyst element that promotes crystallization, and the like. Examples of elements that promote crystallization include nickel, iron, palladium, tin, lead, cobalt, platinum, copper, and gold. A method of performing heat treatment using a catalyst element that promotes crystallization can perform crystallization at a lower temperature and in a shorter time than a method of performing crystallization only by heat treatment.

  Next, if necessary, a small amount of impurity for controlling the threshold value is added to the semiconductor layer (so-called channel doping). The addition of the impurity may be an impurity imparting n-type (for example, phosphorus) or p-type. Impurity to be added (for example, boron) is performed by an ion doping method or the like.

  Then, the island-shaped semiconductor layer 52 is obtained by forming the semiconductor layer into a predetermined shape. The semiconductor layer is formed by forming a photoresist on the semiconductor layer, exposing the photoresist to a predetermined mask shape, and baking the photoresist. In this way, a resist mask is formed on the semiconductor layer. Then, the island-shaped semiconductor layer 52 can be formed by etching the semiconductor layer using the resist mask as a mask.

  Next, a gate insulating layer 53 is formed so as to cover the island-shaped semiconductor layer 52. The gate insulating layer 53 is formed using a plasma CVD method or a sputtering method. In this embodiment mode, silicon oxide is used. The film thickness is 40 to 150 nm.

  Next, the gate electrode 54 is formed over the gate insulating layer 53. The gate electrode 54 can be formed using an element selected from tantalum, tungsten, titanium, molybdenum, aluminum, copper, chromium, and niobium, or an alloy material or a compound material containing the element as a main component. Alternatively, a polycrystalline silicon film doped with an impurity element such as phosphorus may be used. Further, an AgPdCu alloy may be used.

  In the present embodiment, the gate electrode 54 is formed as a single layer. However, the gate electrode 54 may have a laminated structure. For example, there is a two-layer structure using tungsten as a lower layer and molybdenum as an upper layer.

  Next, a high concentration impurity is added to the island-shaped semiconductor layer 52 using the gate electrode 54 as a mask. Thus, a thin film transistor 70 including the island-shaped semiconductor layer 52, the gate insulating layer 53, and the gate electrode 54 is formed.

  Note that there is no particular limitation on the manufacturing process of the thin film transistor, and it may be changed as appropriate so that a transistor with a desired structure can be manufactured.

  In this embodiment mode, a top gate thin film transistor using a crystalline silicon film crystallized by laser crystallization is used. However, a bottom-gate thin film transistor can also be used for the pixel portion.

  The addition of an impurity element will be described. The impurity element is an element that can impart one conductivity type to the island-shaped semiconductor layer 52. As an impurity element imparting n-type conductivity, phosphorus can be given. As an impurity element imparting p-type conductivity, boron or the like can be given. In the case where the first electrode 101 of the light emitting element functions as an anode, it is desirable to select a p-type impurity element. On the other hand, when the first electrode 101 of the light-emitting element functions as a cathode, it is desirable to select the impurity element so as to be n-type.

  Thereafter, an insulating film 59 is formed of silicon nitride so as to cover the gate electrode 54 and the gate insulating layer 53. After the insulating film 59 is formed, the impurity element is activated and the island-shaped semiconductor layer 52 is hydrogenated by heating at 480 ° C. for about 1 hour (FIG. 2A).

  Next, a first interlayer insulating layer 60 covering the insulating film 59 (hydrogenated film) is formed. As the first interlayer insulating layer 60, silicon oxide, acrylic resin, polyimide, siloxane, or the like may be used. In this embodiment mode, a silicon oxide film is used (FIG. 2B).

  Next, a contact hole reaching the island-shaped semiconductor layer 52 is formed. The contact hole can be formed by etching using a resist mask until the island-shaped semiconductor layer 52 is exposed (FIG. 2C).

  Thereafter, a conductive layer is formed. The conductive layer is processed into a desired shape to form the connection portion 61a, the first wiring 61b, and the like. This wiring uses a single-layer structure or a laminated structure such as aluminum, copper, an alloy of aluminum, carbon, and nickel, or an alloy of aluminum, carbon, and molybdenum (FIG. 2D).

  Thereafter, a second interlayer insulating layer 63 is formed. As a material of the second interlayer insulating layer 63, acrylic resin, polyimide, siloxane, or the like can be used. In this embodiment mode, siloxane is used as the second interlayer insulating layer 63 (FIG. 2E).

  Next, an inorganic insulating layer such as silicon nitride may be formed on the second interlayer insulating layer 63. By forming the inorganic insulating layer, the second interlayer insulating layer 63 can be prevented from being etched more than necessary in the subsequent etching of the pixel electrode. Next, a contact hole that penetrates through the second interlayer insulating layer 63 and reaches the connection portion 61a is formed.

  Next, a light-transmitting conductive layer is formed. After that, the lower electrode 64 is formed by processing the light-transmitting conductive layer. The lower electrode 64 is in contact with the connection portion 61a.

  The material of the lower electrode 64 is aluminum (Al), silver (Ag), gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe ), Cobalt (Co), copper (Cu), palladium (Pd), lithium (Li), cesium (Cs), magnesium (Mg), calcium (Ca), strontium (Sr), titanium (Ti), etc. Or alloys of aluminum and silicon (Al-Si), alloys of aluminum and titanium (Al-Ti), alloys of aluminum, silicon and copper (Al-Si-Cu), or nitriding 2-20% for nitrides of metal materials such as titanium, ITO (indium tinoxide), ITO containing silicon, and indium oxide Or the like can be used in IZO (indiumzincoxide) like metal compound mixed zinc oxide (ZnO).

  Further, the electrode from which light is extracted is formed of a conductive film having transparency. As a material for the conductive film having transparency, ITO (indium tinoxide), ITO containing silicon (hereinafter referred to as ITSO), IZO (indium zinc oxide) in which 2 to 20% zinc oxide (ZnO) is mixed with indium oxide, etc. In addition to a metal compound, a thin film of metal such as Al or Ag is used. In the case where light emission is extracted from the second electrode 102, the lower electrode 64 can be made of a highly reflective material (Al, Ag, etc.). In this embodiment, ITSO is used as the lower electrode 64 (FIG. 3A).

  Next, an insulating layer made of an organic material or an inorganic material is formed. Subsequently, the insulating layer is processed so that a part of the lower electrode 64 is exposed, whereby the partition wall 65 is formed. As a material of the partition wall 65, a photosensitive organic material (acrylic, polyimide, or the like) can be used. Note that an organic material or an inorganic material that does not have photosensitivity may be used (FIG. 3B).

  Next, a layer 66 containing a light-emitting substance is formed. Subsequently, an upper electrode 67 is formed to cover the layer 66 containing a luminescent material. As a result, a light emitting element portion 93 in which the layer 66 containing a light emitting substance is sandwiched between the lower electrode 64 and the upper electrode 67 can be manufactured. Light emission can be obtained by applying a voltage to the light emitting element portion. The material of the upper electrode 67 can be the same material as the material of the lower electrode 64. In this embodiment, aluminum is used as the upper electrode 67.

  The layer 66 containing a light-emitting substance is formed by an evaporation method, an inkjet method, a spin coating method, a dip coating method, or the like. The layer 66 containing a light-emitting substance contains the stilbene derivative of the present application. As described in Embodiment Mode 3, the layer 66 containing a light-emitting substance may be a stack of layers having each function, or may be a single layer of a light-emitting layer. The layer 66 containing a light-emitting substance contains the material described in Embodiment 1 as a light-emitting layer. Further, the material described in Embodiment Mode 1 may be included as a host of the light emitting layer or may be included as a dopant. In addition, the material described in Embodiment 1 may be included as a layer other than the light-emitting layer in the layer containing a light-emitting substance or a part thereof. The material used in combination with the material described in Embodiment 1 may be a low molecular material, a medium molecular material (including oligomers and dendrimers), or a high molecular material. In addition, as a material used for the layer 66 containing a light-emitting substance, an organic compound is usually used in a single layer or a stacked layer. However, in the present invention, a structure in which an inorganic compound is used for part of a film made of an organic compound is also used. Include.

Thereafter, a silicon oxide film containing nitrogen is formed as a passivation film by a plasma CVD method. Silicon oxynitride film made from SiH ₄ , N ₂ O, and NH _{3 by} plasma CVD, silicon oxynitride film made from SiH ₄ and N ₂ O, or SiH ₄ and N ₂ O diluted with Ar A silicon oxynitride film manufactured using the prepared gas may be formed.

Further, a silicon oxynitride film manufactured from SiH ₄ , N ₂ O, and H ₂ may be applied as the passivation film.

  Subsequently, the display portion is sealed in order to protect the light emitting element from a substance that promotes deterioration of the light emitting element (for example, moisture). In the case where the second substrate 94 is used for sealing, the second substrate 94 is bonded using an insulating sealing material so that the external connection portion is exposed. Next, a light-emitting device is completed by attaching a flexible wiring board to the external connection portion.

  An example of the structure of the light-emitting device manufactured as described above will be described with reference to FIG. In addition, even if the shapes are different, parts showing similar functions are denoted by the same reference numerals, and explanations thereof are omitted. In the present embodiment, the thin film transistor 70 having an LDD structure is connected to the light emitting element portion 93 through the connection portion 61a.

  In the structure shown in FIG. 4A, the lower electrode 64 is formed using a light-transmitting conductive film, and light is extracted from the first substrate 50 side. Note that the second substrate 94 is fixed to the first substrate 50 using a sealant or the like after the light emitting element portion 93 is formed. Filling the second substrate 94 and the element with a light-transmitting resin 88 or the like and sealing them can prevent the light-emitting element portion 93 from being deteriorated by moisture. In addition, it is desirable that the light-transmitting resin 88 has a hygroscopic property. Furthermore, it is desirable to disperse a highly light-transmitting desiccant 89 in the light-transmitting resin 88 because the influence of moisture can be suppressed.

  In FIG. 4B, both the lower electrode 64 and the upper electrode 67 are formed of a light-transmitting conductive film, and light is emitted from the first substrate 50 and the second substrate 94. Yes. Further, in this configuration, by providing the outer polarizing plate 90 on the first substrate 50 and the second substrate 94, it is possible to prevent the screen from being seen through, and thus visibility is improved. A protective film 91 is preferably provided outside the outer polarizing plate 90.

  Note that a signal supplied to the light emitting device of the present invention having a display function may be either an analog video signal or a digital video signal.

  This embodiment can be used in combination with any of the other embodiments.

(Embodiment 5)
In this embodiment mode, the appearance of a panel which is a light-emitting device of the present invention will be described with reference to FIG. FIG. 5 is a top view of a panel, in which a transistor and a light-emitting element are sealed with a TFT substrate 4001, a counter substrate 4006, and a sealant 4005. FIG. 5B corresponds to the cross-sectional view of FIG. In addition, as the light-emitting element mounted on this panel, those described in other embodiments can be applied.

  A sealant 4005 is provided over the TFT substrate 4001 so as to surround the pixel region 4002, the signal line driver circuit 4003, and the scan line driver circuit 4004. A counter substrate 4006 is provided over the pixel region 4002, the signal line driver circuit 4003, and the scan line driver circuit 4004. A filler 4007 is sealed together with the pixel region 4002, the signal line driver circuit 4003, and the scan line driver circuit 4004.

  Each of the pixel region 4002, the signal line driver circuit 4003, and the scan line driver circuit 4004 includes a plurality of thin film transistors. FIG. 5B illustrates a driver circuit portion thin film transistor 4008 included in the signal line driver circuit 4003 and a pixel portion thin film transistor 4010 included in the pixel region 4002.

  The light emitting element portion 4011 is electrically connected to the pixel portion thin film transistor 4010.

  The first lead wiring 4014 corresponds to a wiring for supplying a signal or a power supply voltage to the pixel region 4002, the signal line driver circuit 4003, and the scan line driver circuit 4004. The first lead wiring 4014 is connected to the connection terminal 4016 via the second lead wiring 4015a and the third lead wiring 4015b. The connection terminal 4016 is electrically connected to a terminal included in a flexible printed circuit (hereinafter referred to as an FPC 4018) through an anisotropic conductive film 4019.

  Note that as the filler 4007, an ultraviolet curable resin or a thermosetting resin can be used in addition to an inert gas such as nitrogen or argon. For example, polyvinyl chloride, acrylic resin, polyimide, epoxy resin, silicon resin, polyvinyl butyral, or the like can be used.

  Note that the light-emitting device of the present invention includes in its category a panel in which a pixel portion having a light-emitting element is formed and a module in which an IC is mounted on the panel.

  This embodiment can be used in combination with any of the other embodiments.

(Embodiment 6)
FIG. 6A illustrates an example of a structure of the light-emitting device of the present invention. FIG. 6A is a cross-sectional view of a pixel portion of a passive matrix light-emitting device. The light-emitting device of the present invention illustrated in FIG. 6A includes a first substrate 200, a first electrode 201 of a light-emitting element, a partition 202, a light-emitting stacked body 203, a second electrode 204 of the light-emitting element, and a second substrate. 207 configurations are included.

  A portion to be a pixel is a portion in which the light-emitting stacked body 203 is sandwiched between the first electrode 201 and the second electrode 204. The first electrode 201 and the second electrode 204 are formed in a stripe shape orthogonal to each other, and a portion to be a pixel is formed at an intersecting portion. The partition 202 is formed in parallel with the second electrode 204, and a portion to be a pixel is insulated from a portion to be another pixel having the same first electrode 201 by the partition 202.

  In this embodiment mode, Embodiment Mode 5 may be referred to for specific materials and structures of the first electrode 201, the second electrode 204, and the light-emitting stacked body 203.

  In addition, the first substrate 200, the partition 202, and the second substrate 207 in FIG. 6A correspond to the first substrate 50, the partition 65, and the second substrate 94 in Embodiment 4, respectively, and their configurations. Since the materials and effects are the same as those in the fifth embodiment, repeated description is omitted. Refer to the description in the fifth embodiment.

  In the light emitting device, a protective film 210 is formed to prevent intrusion of moisture and the like, and a second substrate 207 such as a ceramic material such as glass, stone, or alumina or a synthetic material is fixed with an adhesive 211 for sealing. Further, when connecting to an external circuit, the external input terminal is connected using a flexible printed wiring board 213 through an anisotropic conductive film 212. For the protective film 210, silicon nitride or the like can be used.

  FIG. 6B illustrates a module formed by connecting an external circuit to the panel illustrated in FIG. The module electrically connects the module to the external circuit board on which the power supply circuit and the signal processing circuit are formed by fixing the flexible printed wiring board 25 to the external input terminal section 18 and the external input terminal section 19. In addition, the method of mounting the driver IC 28 which is one of the external circuits may be either the COG method or the TAB method. FIG. 6B shows a state in which a driver IC 28 which is one of external circuits is mounted using the COG method. The signal processing circuit and driver IC 28 formed on the external circuit board are control circuits for the light emitting elements. A light-emitting device and an electronic device equipped with a control circuit can display various images on a panel by turning on and off the light-emitting element or controlling luminance by the control circuit.

  Note that the panel and the module correspond to one mode of the light-emitting device of the present invention, and both are included in the category of the present invention.

(Embodiment 7)
As an electronic device of the present invention equipped with the light emitting device (module) of the present invention, a video camera, a digital camera, a goggle type display (head mounted display), a navigation system, an audio reproduction device (car audio component, etc.), a computer, a game device , A portable information terminal (mobile computer, cellular phone, portable game machine, electronic book, etc.), an image reproducing device (specifically, a digital versatile disc (DVD)) provided with a recording medium, and the image And the like). Specific examples of these electronic devices are shown in FIGS.

  FIG. 7A shows a light-emitting device, such as a television receiver or a personal computer monitor. These include a housing 2001, a display portion 2003, a speaker portion 2004, and the like. The light-emitting device of the present invention is a light-emitting device with high display quality of the display portion 2003 and high reliability. In order to increase contrast, the pixel portion may be provided with a polarizing plate or a circular polarizing plate.

  FIG. 7B illustrates a mobile phone. This includes a main body 2101, a housing 2102, a display unit 2103, an audio input unit 2104, an audio output unit 2105, operation keys 2106, an antenna 2108, and the like. The mobile phone of the present invention is a mobile phone with high display quality of the display portion 2103 and high reliability.

  FIG. 7C illustrates a computer. This includes a main body 2201, a housing 2202, a display portion 2203, a keyboard 2204, an external connection port 2205, a pointing device 2206, and the like. The computer of the present invention is a highly reliable computer with high display quality of the display portion 2203. Although FIG. 7C illustrates a notebook computer, the present invention can also be applied to a desktop computer or the like in which a hard disk and a display portion are integrated.

  FIG. 7D illustrates a mobile computer. This includes a main body 2301, a display portion 2302, a switch 2303, operation keys 2304, an infrared port 2305, and the like. The mobile computer of the present invention is a mobile computer with high display quality of the display portion 2302 and high reliability.

  FIG. 7E illustrates a portable game machine. This includes a housing 2401, a display portion 2402, a speaker portion 2403, operation keys 2404, a recording medium insertion portion 2405, and the like. The portable game machine of the present invention is a portable game machine with high display quality of the display portion 2402 and high reliability.

  As described above, the applicable range of the present invention is so wide that it can be used for electronic devices in various fields.

  As an example of the anthracene derivative of the present invention, a compound represented by the structural formula (16) of Embodiment 1, (E) -4,4′-bis [4- (10-phenyl-9-anthryl) phenyl] stilbene ( Hereinafter, a synthesis method of PAP2S will be described.

[Step 1: Synthesis of (E) -4,4′-dibromostilbene]
(I) Synthesis of 4-bromobenzyltriphenylphosphonium bromide After 25.2 g (101 mmol) of 4-bromobenzylbromide and 100 mL of acetone were put into a 200 mL Erlenmeyer flask, 29.1 g (111 mmol) of triphenylphosphine was added. The mixture was then reacted by stirring at room temperature for 23 hours. After completion of the reaction, the precipitate in the reaction mixture was collected by suction filtration. Then, 50.5 g of a white powdered solid of 4-bromobenzyltriphenylphosphonium bromide, which was the target product, was obtained in a yield of 98%. A synthesis scheme of 4-bromobenzyltriphenylphosphonium bromide is shown below (synthesis scheme a-1).

(Ii) Synthesis of 4,4′-dibromostilbene 50.2 g (97.9 mmol) of 4-bromobenzyltriphenylphosphonium bromide and 21.7 g (118 mmol) of 4-bromobenzaldehyde were placed in a 500 mL three-necked flask. The air in the flask was replaced with nitrogen. Thereafter, 200 mL of tetrahydrofuran (abbreviation: THF) was added to the mixture. To this mixture, a suspension obtained by mixing 13.2 g (118 mmol) of potassium tert-butoxide in 100 mL of THF was added dropwise. Then, it was made to react by stirring for 24 hours at room temperature. After completion of the reaction, the reaction solution was washed with water, and the precipitate was collected by suction filtration. Then, 14.0 g of a white powdered solid of (E) -4,4′-dibromostilbene, which was the target product, was obtained in a yield of 42%. Further, the filtrate from which the precipitate was collected was extracted with ethyl acetate, and the extracted solution was dried over magnesium sulfate. After drying, the mixture was suction filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene). When the obtained solution was concentrated, 14.8 g of a light yellow solid of (Z) -4,4′-dibromostilbene was obtained in a yield of 45%. A synthesis scheme of 4,4′-dibromostilbene is shown below (synthesis scheme a-2).

[Step 2: Synthesis of 4- (10-phenyl-9-anthryl) phenylboronic acid]
(I) Synthesis of 9-phenylanthracene 9-bromoanthracene 25.4 g (100 mmol), phenylboronic acid 12.8 g (105 mmol), palladium (II) acetate 0.233 g (1.00 mmol), tri (ortho-tolyl) 0.913 g (3.00 mmol) of phosphine was placed in a 500 mL three-necked flask. The air in the flask was replaced with nitrogen. Thereafter, 100 mL of ethylene glycol dimethyl ether (abbreviation: DME) and 75 mL (150 mmol) of an aqueous potassium carbonate solution (2.0 mol / L) were added to the mixture, and the mixture was reacted by refluxing at 90 ° C. for 6 hours. After completion of the reaction, the precipitate in the reaction mixture was collected by suction filtration. When the obtained solid was recrystallized with a mixed solvent of chloroform and hexane, 20.8 g of white powdery solid of 9-phenylanthracene, which was the target product, was obtained in a yield of 82%. A synthesis scheme of 9-phenylanthracene is shown below (synthesis scheme b-1).

(Ii) 9-Bromo-10-phenylanthracene synthesis method 20.8 g (81.7 mmol) of 9-phenylanthracene and 300 mL of carbon tetrachloride were placed in a 500 mL three-necked flask. A solution prepared by dissolving 13.1 g (81.7 mmol) of bromine in 5.00 mL of carbon tetrachloride was added dropwise to the mixture. After completion of the dropping, the reaction solution was stirred at room temperature for 3 hours to be reacted. And about 100 mL of sodium thiosulfate aqueous solution was added to the reaction solution, and reaction was complete | finished. The organic layer of this mixture was washed with water and dried over magnesium sulfate. After drying, the mixture was filtered with suction, and the filtrate was concentrated to obtain a solid. When the obtained solid was recrystallized with a mixed solvent of chloroform and hexane, 23.8 g of a pale yellow powdered solid of 9-bromo-10-phenylanthracene, which was the target product, was obtained in a yield of 71%. A synthesis scheme of 9-bromo-10-phenylanthracene is shown below (synthesis scheme b-2).

(Iii) Method for synthesizing 9-iodo-10-phenylanthracene 10 g (30 mmol) of 9-bromo-10-phenylanthracene was placed in a 500 mL three-necked flask. The air in the flask was replaced with nitrogen. Then, 200 mL of tetrahydrofuran (abbreviation: THF) was added, and then the flask was placed in a low-temperature thermostatic layer to bring the reaction solution to −40 ° C. To this solution, 36 mL (23 mmol) of n-butyllithium (1.54 mol / L hexane solution) was dropped, and the mixture was reacted at the same temperature for 1 hour. After stirring, a solution obtained by dissolving 9.1 g (39 mmol) of iodine in 40 mL of THF was added dropwise to the reaction solution over 1 hour while maintaining at −40 ° C., and then stirred at the same temperature for 1 hour. Thereafter, the flask was taken out from the low temperature constant temperature layer and stirred for 24 hours to return the reaction solution to room temperature. After completion of the reaction, about 100 mL of an aqueous sodium thiosulfate solution was added to complete the reaction. The organic layer of this mixture was washed with water and saturated brine, and dried over magnesium sulfate. After drying, the mixture was filtered with suction, and the filtrate was concentrated to obtain a residue. The resulting residue was dissolved in toluene and suction filtered through Florisil, Celite, and alumina. The filtrate was concentrated to obtain 29 g of a 9-iodo-10-phenylanthracene yellow solid, which was the target product, in a yield of 96%. A synthesis scheme of 9-iodo-10-phenylanthracene is shown below (synthesis scheme b-3).

(Iv) Method for synthesizing 9- (4-bromophenyl) -10-phenylanthracene 9-iodo-10-phenylanthracene 5.3 g (14 mmol), 4-bromophenylboronic acid 2.9 g (14 mmol), tetrakis (tri Phenylphosphine) palladium (0) 0.18 g (0.15 mmol) was placed in a 100 mL three-necked flask. The air in the flask was replaced with nitrogen. To this mixture, 30 mL of toluene and 15 mL (31 mmol) of an aqueous sodium carbonate solution (2.0 mol / L) were added, and the mixture was reacted at reflux at 110 ° C. for 10 hours. After completion of the reaction, the precipitate in the reaction mixture was collected by suction filtration. The obtained solid was dissolved in toluene and suction filtered through Florisil, Celite and alumina, and the filtrate was concentrated. The obtained solid was recrystallized with a mixed solvent of chloroform and hexane. As a result, 4.1 g of a light yellow powdery solid of 9- (4-bromophenyl) -10-phenylanthracene, which was the target substance, was obtained in a yield of 72%. Obtained. A synthesis scheme of 9- (4-bromophenyl) -10-phenylanthracene is shown below (synthesis scheme b-4).

(V) 4- (10-phenyl-9-anthryl) phenylboronic acid synthesis method 20.0 g (48.9 mmol) of 9- (4-bromophenyl) -10-phenylanthracene was placed in a 500 mL three-necked flask. The air in the flask was replaced with nitrogen. Tetrahydrofuran (abbreviation: THF) (300 mL) was added thereto, and then the flask was placed in a low-temperature thermostatic layer to bring the reaction solution to −78 ° C. To this solution, 34.2 mL (53.8 mmol) of n-butyllithium (1.57 mol / L hexane solution) was added dropwise and stirred at the same temperature for 2 hours. Thereafter, 12.6 mL (112 mmol) of trimethyl borate was added, the flask was taken out from the low-temperature thermostatic layer, and stirred for 24 hours to return the reaction solution to room temperature. After completion of the reaction, 200 mL of 1.0 mol / L hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. The organic layer of this mixture was washed with water, and the washed aqueous layer was extracted with ethyl acetate. The extracted solution was combined with the organic layer, washed with saturated brine, and dried over magnesium sulfate. After drying, the mixture was suction filtered, and the filtrate was concentrated to obtain a residue. The obtained residue was recrystallized with a mixed solvent of chloroform and hexane. As a result, 15.3 g of a white powdered solid of 4- (10-phenyl-9-anthryl) phenylboronic acid, which was the object, was obtained in a yield of 84%. Obtained. A synthesis scheme of 4- (10-phenyl-9-anthryl) phenylboronic acid, which is the target product, is shown below (Synthesis scheme b-5).

[Step 3: Synthesis of (E) -4,4′-bis [4- (10phenyl-9-anthryl) phenyl] stilbene]
(E) -4,4′-dibromostilbene 2.0 g (5.9 mmol), 4- (10-phenyl-9-anthryl) phenylboronic acid 4.9 g (13 mmol), palladium (II) acetate 0.053 g ( 0.24 mmol) and 0.25 g (0.83 mmol) of tri (ortho-tolyl) phosphine were put into a 100 mL three-necked flask. The air in the flask was replaced with nitrogen. To this mixture, 30 mL of ethylene glycol dimethyl ether (abbreviation: DME) and 18 mL (35 mmol) of an aqueous potassium carbonate solution (2.0 mol / L) were added, and the mixture was reacted by refluxing at 90 ° C. for 6 hours. After completion of the reaction, the precipitate in the reaction mixture was collected by suction filtration. The collected precipitate was washed with toluene, and as a result, a light yellow powder of the target product (E) -4,4′-bis [4- (10-phenyl-9-anthryl) phenyl] stilbene (abbreviation: PAP2S) was obtained. 4.7 g of solid was obtained with a yield of 94%. A synthesis scheme of (E) -4,4′-bis [4- (10-phenyl-9-anthryl) phenyl] stilbene is shown below (synthesis scheme c-1).

¹ H NMR data of the obtained (E) -4,4′-bis [4- (10-phenyl-anthryl) phenyl] stilbene is shown below. ¹ H NMR (CDCl ₃ , 300 MHz): δ = 7.14-7.21 (m, 2H), 7.30-7.44 (m, 11H), 7.48-7.52 (m, 5H) 7.54-7.61 (m, 8H), 7.63-7.73 (m, 8H), 7.77-7.81 (m, 6H), 7.83-7.91 (m, 4H)

A ¹ H NMR chart is shown in FIG. Note that FIG. 8B is a chart in which the range of 7.0 ppm to 8.0 ppm in FIG.

  Moreover, the obtained PAP2S was formed into a film by the vapor deposition method. Then, the absorption spectrum of PAP2S in a thin film state was measured using a UV / visible light spectrophotometer (manufactured by JASCO Corporation, V-550). The absorption spectra of PAP2S are shown in FIGS. 9 and 10, the horizontal axis represents wavelength (nm) and the vertical axis represents intensity (arbitrary unit). FIG. 9 shows an absorption spectrum in a thin film state. On the other hand, FIG. 10 shows an absorption spectrum in a state in which it is dissolved in a toluene solution. In addition, emission spectra of PAP2S are shown in FIGS. 11 and 12, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). FIG. 11 shows an emission spectrum (excitation wavelength: 402 nm) in a thin film state. On the other hand, FIG. 12 shows an emission spectrum (excitation wavelength: 341 nm) in a state dissolved in a toluene solution. From FIGS. 11 and 12, light emission from PAP2S has peaks at 449 nm and 542 nm in a single film state. Moreover, it turns out that it has a peak at 431 nm in a toluene solution. These luminescences were visually recognized as blue luminescent colors. As described above, it was found that PAP2S is a substance suitable as a light-emitting substance that emits blue light.

  Further, the ionization potential of PAP2S in a thin film state was measured using a photoelectron spectrometer (AC-2, manufactured by Riken Keiki Co., Ltd.), and was 5.72 eV. Therefore, it was found that the HOMO level was −5.72 eV. Further, from the absorption spectrum of PAP2S in a thin film state, the wavelength of the absorption edge on the long wavelength side of the absorption spectrum was estimated by a tauc plot assuming direct transition, and the energy gap was found to be 2.93 eV. When the LUMO level was determined from this energy gap and the value of the HOMO level, the LUMO level was -2.79 eV.

  Thermogravimetry-differential thermal analysis (TG-DTA) of PAP2S was performed. For the measurement, a high vacuum differential type suggestive thermal balance (manufactured by Bruker AXS Co., Ltd., TDA2410SA) was used. From the relationship between weight and temperature (thermogravimetry), it was found that the temperature at which the weight became 95% or less with respect to the weight at the start of measurement was 475 ° C., and PAP2S showed good heat resistance.

  Further, 1.3 g of the obtained (E) -4,4′-bis [4- (10-phenyl-9-anthryl) phenyl] stilbene (abbreviation: PAP2S) was added at a pressure of 5.1 Pa and an argon flow rate of 3.0 mL / When sublimation purification was performed by heating to 380 ° C. under the condition of min, 0.9 g was recovered and the recovery rate was 75%.

  Moreover, the thermophysical property of PAP2S was measured using the differential scanning calorimeter (DSC, the Perkin Elmer company make, Pyris1). First, 4.5 mg of PAP2S was weighed and introduced into the apparatus. And the DSC chart of FIG. 13 was obtained by heating from -10 degreeC to 320 degreeC with the temperature increase rate of 40 degreeC / min. From this chart, it was found that a glass transition point was observed in PAP2S, and its glass transition temperature (Tg) was 176 ° C. From this, it was found that PAP2S has a high glass transition point.

FIG. 14 illustrates a light-emitting element of the present invention. 9A to 9D are cross-sectional views illustrating a method for manufacturing an active matrix light-emitting device of the present invention. 9A to 9D are cross-sectional views illustrating a method for manufacturing an active matrix light-emitting device of the present invention. Sectional drawing of the light-emitting device of this invention. 2A and 2B are a top view and a cross-sectional view of a light-emitting device of the present invention. 2A and 2B are a top view and a cross-sectional view of a light-emitting device of the present invention. FIG. 6 illustrates an example of an electronic device to which the present invention can be applied. ¹ H NMR chart of PAP2S Absorption spectrum of PAP2S Absorption spectrum of PAP2S Emission spectrum of PAP2S Emission spectrum of PAP2S DSC chart for PAP2S

Explanation of symbols

18 External Input Terminal 19 External Input Terminal 25 Flexible Printed Circuit Board 28 Driver IC
50 first substrate 51a first base insulating layer 51b second base insulating layer 61a connecting portion 61b first wiring 52 island-like semiconductor layer 53 gate insulating layer 54 gate electrode 59 insulating film 60 first interlayer insulating layer 63 Second interlayer insulating layer 64 Lower electrode 65 Partition 66 Luminescent substance-containing layer 67 Upper electrode 70 Thin film transistor 88 Resin 89 Desiccant 90 Outer polarizing plate 93 Light emitting element section 94 Second substrate 101 First electrode 102 Second Electrode 103 Layer 200 containing luminescent material First substrate 201 First electrode 202 Partition 203 Light emitting laminate 204 Second electrode 207 Second substrate 210 Protective film 211 Adhesive 212 Anisotropic conductive film 213 Flexible printed circuit board 4001 TFT substrate 4002 Pixel region 4003 Signal line driver circuit 4004 Scan line driver circuit 4005 Sealing material 400 The first lead interconnection counter substrate 4007 filler 4008 driver circuit portion TFT 4010 pixel portion TFT 4011 light emitting element section 4014 4016 Connection terminal 4018 FPC
4019 Anisotropic conductive film 4015a Second routing wiring 4015b Third routing wiring

Claims (9)

A stilbene derivative represented by the following general formula (1).

(In the formula, X and Y are substituents represented by the following general formula (2) or the following general formula (3), and X and Y may be the same or different.)

A stilbene derivative represented by the following general formula (1).

(In the formula, X and Y are substituents represented by the following general formula (2), and X and Y may be the same or different.)

A stilbene derivative represented by the following general formula (1).

(In the formula, X and Y are substituents represented by the following general formula (3), and X and Y may be the same or different.)

A stilbene derivative represented by the following general formula (1).

(In the formula, X is a substituent represented by the following general formula (2), and Y in the formula is a substituent represented by the following general formula (3).)

A stilbene derivative represented by the following structural formula (4).

  The material for light emitting elements containing the stilbene derivative as described in any one of Claims 1 thru | or 5. Having a layer comprising a luminescent material sandwiched between two electrodes;
The light-emitting element according to claim 6, wherein the layer containing the light-emitting material includes the light-emitting element material according to claim 6.   A display device comprising the light-emitting element according to claim 7.   An electronic apparatus comprising the display device according to claim 8.

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