WO2006043539A1

WO2006043539A1 - Light-emitting compound, light-emitting polymer compound and light-emitting device

Info

Publication number: WO2006043539A1
Application number: PCT/JP2005/019107
Authority: WO
Inventors: Tadao Nakaya; Ryoji Matsumoto
Original assignee: Hirose Engineering Co., Ltd.
Priority date: 2004-10-19
Filing date: 2005-10-18
Publication date: 2006-04-27
Also published as: TW200613288A

Abstract

Disclosed are a light-emitting compound and a light-emitting polymer compound which emit blue light or the like and contain pyrene. Also disclosed is a light-emitting device. Specifically disclosed are a light-emitting compound and a light-emitting polymer compound respectively characterized by having a specific structure. Also specifically disclosed is a light-emitting device characterized by comprising a light-emitting layer arranged between a pair of electrodes and containing the light-emitting compound or the light-emitting polymer compound.

Description

Specification

Light emitting compound, light emitting polymer compound, and light emitting device

Technical field

The present invention relates to a light emitting compound, a light emitting polymer compound, and a light emitting element, and more particularly to a light emitting compound, a light emitting polymer compound, and a light emitting element containing pyrene. Background art

[0002] As a compound capable of emitting blue light, the general formula is Ar2—CH—Ar—CH—Arl (however,

twenty two

Ar is a vinylene group, a naphthyl group, or an anthryl group. ) Has been proposed (Patent Document 1). This new substance is a robust substance that emits blue light and emits light with high brightness and high color purity.

In the technical field of organic EL, in addition to the above novel compounds capable of emitting blue light, various luminescent compounds are being searched!

Patent Document 1: Japanese Patent Application Laid-Open No. 2004-18401

Disclosure of the invention

Problems to be solved by the invention

An object of the present invention is to provide a light-emitting compound, a light-emitting polymer compound, and a light-emitting element that emit blue light and contain pyrene.

Means for solving the problem

[0006] As means for solving the above problems,

Claim 1

A light-emitting compound characterized by having a structure represented by the following formula (1):

[0007] [Chemical 1]

[In the formula (1), A represents any group represented by the following formulas (2) to (13). ] [Chemical 2]

[In the formula (2), two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms, and the two R ^{1 s} may be the same or different from each other! / . ]

[Chemical 3]

[In the formula (3), two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms, and the two R ^{1 s} may be the same or different from each other! / . ]

[0011] [Chemical 5]

H2 Second — • (5)

[In the formula (5), R ² represents H or a methyl group. ]

[0012] [Chemical 6]

Claim 2

A light-emitting polymer compound having a repeating unit structure represented by the following formula (14):

[0013] [Chemical 7]

[However, in the formula (14), two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms, and the two R ^{1 s} may be the same or different from each other. ]

Claim 3

A light-emitting polymer compound having a repeating unit structure represented by the following formula (15):

[In the formula (15), R ² represents H or a methyl group. ]

Claim 4

A light emitting polymer compound having a repeating unit structure represented by the following formula (16):

[In the formula (16), R ² represents H or a methyl group. ]

Claim 5 A light emitting layer comprising a light emitting layer containing the light emitting compound according to claim 1 or the light emitting polymer compound according to any one of claims 2 to 4 between a pair of electrodes. It is an element.

The invention's effect

[0014] According to the present invention, since it has a pyrene skeleton in the molecule, the emission intensity is increased, the solubility in a solvent is improved, the oxaziazoline ring skeleton has a high electron-withdrawing property, and one of the oxaziazoline ring skeletons is present. Has a pyrene skeleton and the other of the oxadiazoline ring skeleton has a fluorene skeleton, a force rubazole skeleton or an aromatic ring skeleton, and therefore can provide a light emitting compound capable of emitting blue light and a light emitting polymer compound. . According to the present invention, the molecular structure includes an oxaziazole skeleton, a pyrene skeleton bonded to one of the oxaziazole skeletons, and a fluorene skeleton, a force rubazole skeleton, or an aromatic ring skeleton bonded to the other of the oxaziazole skeleton in the molecule. Therefore, it is possible to provide a light-emitting element that can emit light with high luminance such as blue and has a long light emission lifetime.

BEST MODE FOR CARRYING OUT THE INVENTION

The light emitting compound according to the present invention has a structure represented by the following formula (1). Hereinafter, the light-emitting compound represented by the following formula (1) may be referred to as “low-molecular light-emitting compound”.

[0016] [Chemical 8]

[In the above formula (1), A is any group represented by the following formulas (2) to (13). ] [0018] [Chemical 9]

[In the formula (2), two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms,

The two R ^1's may be the same or different! ]

[0020] [Chemical 10]

[In the formula (3), two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms,

The two R ^1's may be the same or different! ]

[0022] [Chemical 11]

[0023] [Chemical 12] : G— • (5)

[In the formula ( ⁵ ), R ² represents H or a methyl group. ]

[0025] [Chemical 13]

[0026] The light-emitting polymer compound according to the present invention has a repeating unit structure represented by the following formula (14).

[0027] [Chemical 14] ( 14:)

[In the formula (14), two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms.

The two R ^{1 s} may be the same as or different from each other. ]

[0029] The light-emitting polymer compound according to the present invention has a repeating unit structure represented by the following formula (15).

[0030] [Chemical 15]

[In the formula (15), R ² represents H or a methyl group. ]

The light-emitting polymer compound according to the present invention has a repeating unit structure represented by the following formula (16).

[0032] [Chemical 16]

[In the formula (16), IT represents H or a methyl group. ]

In the above formula, two R ^{1 s} each represent an alkyl group having 1 to 20 carbon atoms. This Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, and s ec-pentyl. Group, tert-pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group And an eicosyl group. Among these alkyl groups, an alkyl group having 115 carbon atoms is preferable, and an alkyl group having 110 carbon atoms is particularly preferable.

[0034] As a method for producing a luminescent compound according to the present invention, for the luminescent compound in which A in the structural formula represented by the formula (1) is a fluorene skeleton represented by the formula (2), for example, the following reaction formula: The method according to (1) can be mentioned.

[0035] [Chemical 17]

Reaction formula (1)

In reaction formula (1), a acetyl group is introduced into 9,9-dialkylfluorene (a) by Friedel-Crafts reaction to form compound (b), which is further acidified to convert the acetyl group into a carboxylic acid. (C) is formed, and the carboxylic acid in the compound (c) is converted into a salt. Therefore, in place of the acid chloride (d), the acid chloride and hydrazine are reacted to form a carbohydrazide compound (e). This carbohydrazide compound (e) and 1-pyrenecarboxylic acid (f ) To form a dihydrazide compound (g), and this dihydrazide compound (g) is cyclized by heating, and the target compound (A) in the formula (1) is a group represented by the formula (2) ( la) can be generated. 1-Hydroxycarbopyrene (f) can be obtained from a commercially available product. It can be obtained by introducing a acetyl group at the 1-position of pyrene by the Freedel-Crafts reaction, and then acidifying the acetyl group. I'll do it.

[0037] The Friedel-Craft reaction in the above reaction formula is carried out in a solvent such as orthodichlorobenzene (ODB) using anhydrous salt / aluminum, zinc, zinc chloride, boron fluoride, salt / iron salt as a catalyst. It is possible to adopt known reaction conditions. The oxidation reaction in which a acetyl group is converted into a carboxylic acid proceeds by employing an oxidation method using an oxidizing agent such as NaCIO and other known oxidation methods. In order to cyclize CONHNHCO to form an oxadiazole ring, it is preferable to heat using, for example, phosphorus oxytrichloride.

[0038] As a method for producing a light-emitting compound according to the present invention, for a light-emitting compound in which the group A in the structural formula represented by the formula (1) is a fluorene skeleton represented by the formula (3), for example, A method according to reaction formula (2) can be mentioned.

[0039] [Chemical 18]

^,

[0040] In reaction formula (2), 9, 9-dialkylfluorene is acetylated by Friedel-Crafts reaction to obtain 2,7-diacetyl-9,9-dialkylfluorene (compound (bl)), This is oxidized to obtain 2,7-dihydroxycarboluro 9,9-dialkylfluorene (compound (cl)), and this dicarboxylic acid compound (compound (cl) is converted into salt thiol. The acid chloride (compound (h)) is converted into a dicarbohydrazide compound by subjecting the acid chloride (compound (h)) to a monocarbohydrazide derivative (compound (i)) to a hydrogenation reaction. (Compound (j)) is obtained, and this compound (j) is reacted with hydrazine to obtain a compound (m). This compound (m) is reacted with 1-pyrenecarboxylic acid (compound (f)). Compound (o) is produced, and this compound (o) is subjected to carothermal heating to cyclize to obtain compound (p). ) Is dehydrochlorinated to produce the target compound (lb) in which the group A in the formula (1) is represented by the formula (3). The N- (2-chloroethyl) force rubazole is acetylated by the Delcrafts reaction, the acetyl group is oxidized to replace the hydrocarbyl group, and the hydrocarbol group is clogged by thiyl chloride. It can be obtained by further reacting with hydrazine instead of the carbonyl group.

[0041] As a method for producing a luminescent compound according to the present invention, a luminescent compound in which the group A in the structural formula represented by the formula (1) is an N-vinylcarbazole skeleton represented by the formula (4) is provided. Can be exemplified by the method according to the following reaction formula (3). [0042] [Chemical 19]

(3) ΰΰΗ

[0043] In the reaction formula (3), a monocarbohydrazide derivative (compound (i)) obtained using N- (2-chloroethyl) power rubazole as a starting material is reacted with 1-pyrenecarboxylic acid (compound (f)). To obtain a dicarbohydrazide compound (compound (q)). The dicarbohydrazide compound (q) is heated to cyclize to obtain a compound (r). The target compound (lc) in which the group A in the formula (1) is represented by the formula (4) is produced by the dehydrochlorination reaction.

[0044] As a method for producing a luminescent compound according to the present invention, for the luminescent compound in which the group A in the structural formula represented by the formula (1) is a vinyl group represented by the formula (5), for example, the following reaction A method according to formula (4) can be mentioned.

[0045] [Chemical 20]

In reaction formula (4), (meth) acryl carbohydrazide derivative (compound (t)) is obtained by reacting 1-pyrenecarboxylic acid (compound (f)) with (meth) acrylic acid. The target compound (Id) in which the group A in the formula (1) is represented by the formula (5) is then produced by heating and then ring-closing the compound (t).

[0047] As a method for producing a light-emitting compound according to the present invention, for a light-emitting compound in which the group A in the structural formula represented by the formula (1) is an aromatic ring represented by the formulas (6) to (13), For example, a method according to the following reaction formula (5) can be mentioned. In the reaction formula (5), the starting materials benzene, naphthalene, anthracene and pyrene are collectively represented by the aromatic ring compound Ar— I will explain it by displaying H.

[0048] [Chemical 21] Anti-to expression (5)

A ~ ti Ar-COCI-Ar ~ Gu Nn Nri

[0049] In the reaction formula (5), the aromatic ring compound Ar—H is converted into an aromatic ring carboxylate compound Ar—COC1 by the Friedel-Crafts reaction and the subsequent acid reaction and chlorination reaction. The aromatic carboxylic acid chloride Ar—COC1 and hydrazine were reacted to synthesize the carbohydrazide derivative compound ArCONHNH2, and this carbohydrazide derivative compound ArCO NHNH2 and 1-pyrenecarboxylic acid (compound (f)) and To react to the equation (1). The target compound (le) in which the group A is represented by the formulas (6) to (13) is produced.

[0050] As a method for producing a light-emitting polymer compound according to the present invention, the light-emitting compound obtained as described above is polymerized by a polymerization reaction. This polymerization may be homopolymerization or copolymerization. The polymerization reaction may be any of radical polymerization, ion polymerization, and cationic polymerization. Further, as a polymerization mode, a bulk polymerization method, a suspension polymerization method, an emulsion polymerization method and a solution polymerization method can be used.

[0051] The polymerization reaction may be carried out under normal pressure, or under reduced pressure or pressure, but is usually carried out under normal pressure. The polymerization process may be a batch process or a continuous process, but the power of manufacturing efficiency is preferred.

[0052] The light-emitting device according to the present invention will be described below.

FIG. 1 is an explanatory diagram showing a cross-sectional structure of a light-emitting element that is also a single-layer organic EL element. Figure

As shown in FIG. 1, the light emitting element A is formed by laminating a light emitting layer 3 containing a light emitting material and an electrode layer 4 in this order on a substrate 1 on which a transparent electrode 2 is formed.

[0054] When the light-emitting element shown in FIG. 1 contains the light-emitting compound according to the present invention in the light-emitting layer 3, when a current is passed through the transparent electrode 2 and the electrode layer 4, it depends on the type of the light-emitting compound. Lights up in a different color.

For light emission, when an electric field is applied between the transparent electrode 2 and the electrode layer 4, electrons are also injected into the electrode layer 4 side force, holes are injected from the transparent electrode 2, and further electrons are emitted. This is a phenomenon in which energy is released as light when recombining with holes in layer 3 and the energy level returns to the conduction band valence band.

[0056] If the overall shape of the light emitting element A shown in FIG. 1 is a large area planar shape, for example, the light emitting element A is mounted on a wall surface or a ceiling to provide a large area wall surface light emitting element, a large area ceiling surface light emitting element, or the like. It can be set as the planar light-emitting illuminating device. That is, when the light emitting element emits white light according to the light emitting compound, it can be used as a surface light source instead of a conventional linear light source such as a fluorescent lamp or a point light source such as a light bulb. In particular, a wall surface, a ceiling surface, or a floor surface of a living room, an office room, a vehicle room, or the like can be emitted or illuminated as a surface light source by the light emitting element.

[0057] Further, the light emitting element A is displayed on a display screen in a computer or on a mobile phone. It can be used for backlight of a screen, a number display screen in a cash register. In addition, the light-emitting element A can be used as various light sources such as direct illumination and indirect illumination, and can be lit at night and has good visibility, a road sign device, It can also be used as a light source for brake lamps, side lamps, knock lamps and the like in vehicles such as light emitting bulletin boards and automobiles. However, the light emitting element A has a long light emission life because the light emitting layer has a light emitting compound having a pyrene skeleton and an oxaziazole ring skeleton in the light emitting layer. Therefore, the light emitting element A can be used as a light source having a long lifetime.

[0058] In addition, when the light-emitting layer according to the present invention is contained in the light-emitting layer of the light-emitting element A, and other than the red light-emitting compound and the green light-emitting compound, the light-emitting element A is It emits light with a vivid color peculiar to its molecular structure.

[0059] Further, the light-emitting element A includes a substrate 1 formed in a cylindrical shape, and a tubular light-emitting body in which a transparent electrode 2, a light-emitting layer 3, and an electrode layer 4 are laminated in this order on the inner surface side of the substrate 1. can do . When the luminescent compound emits white light, this light-emitting element A uses mercury for V, so it can be used as an environment-friendly light source instead of conventional fluorescent lamps using mercury. it can.

[0060] As the substrate 1, a known substrate can be adopted as long as the transparent electrode 2 can be formed on the surface thereof. Examples of the substrate 1 include a glass substrate, a plastic sheet, a ceramic, and a metal plate obtained by processing the surface into an insulating property such as forming an insulating coating layer on the surface.

When the substrate 1 is opaque, the light emitting element containing the light emitting compound or the like according to the present invention in the light emitting layer is a single-sided illuminating device that can irradiate light on the side opposite to the substrate 1. In addition, when the substrate 1 is transparent, the light emitting device is a double-sided illumination device that can emit light of a color corresponding to the light-emitting compound from the substrate 1 side and the opposite surface.

[0062] The transparent electrode 2 employs various materials as long as it has a large work function and is transparent and can act as an anode by applying a voltage to inject holes into the light emitting layer 3. can do. Specifically, the transparent electrode 2 is made of ITO, InO, SnO, ZnO, Cd

2 3 2 o, etc., and inorganic transparent conductive materials such as compounds thereof, and high conductivity such as polyaniline It can be formed of a molecular material or the like.

[0063] The transparent electrode 2 is formed on the substrate 1 by chemical vapor deposition, spray pyrolysis, vacuum deposition, electron beam deposition, sputtering, ion beam sputtering, ion plating, ion assist. It can be formed by vapor deposition or other methods.

[0064] When the substrate is formed of an opaque member, the electrode formed on the substrate does not need to be a transparent electrode.

[0065] The light emitting layer 3 can be formed as a polymer film in which the low molecular weight light emitting compound or the like according to the present invention is dispersed in a polymer. It can be formed as a molecular film, and can also be formed as a vapor-deposited film formed by vapor-depositing the low-molecular light-emitting compound according to the present invention on the transparent electrode 2.

[0066] Examples of the polymer in the polymer film include polybylcarbazole, poly (3-alkylenthiophene), polyimide containing arylamine, polyfluorein, polyphenylene-ethylene, poly-a-methylstyrene, -Lucarbazole Z α-methylstyrene copolymer and the like. Among these, polyburecarbazole is preferable.

[0067] The content of the light emitting compound according to the present invention in the polymer film is usually 0.01 to 2 wt%, preferably 0.05 to 0.5 wt%.

[0068] The thickness of the polymer film is usually 30 to 500 nm, preferably 100 to 300 nm. If the thickness of the polymer film is too thin, the amount of emitted light may be insufficient. If the thickness of the polymer film is too large, the driving voltage may become too high, which may be undesirable. Flexibility may be lacking when using a curved or annular body.

[0069] The polymer film is formed by a coating method such as a spin casting method, a coating method, and a dipping method using a solution obtained by dissolving the polymer and the light-emitting compound according to the present invention in an appropriate solvent. Can be formed.

[0070] When the light-emitting layer 3 is a vapor-deposited film, the thickness of the vapor-deposited film is generally a force that varies depending on the layer structure in the light-emitting layer, etc. When the thickness of the deposited film is too small or too large, the same problem as described above may occur.

[0071] The electrode layer 4 employs a material having a small work function, such as MgAg, aluminum. It can be formed of a metal simple substance or a metal alloy such as a metal alloy or metal calcium. A preferred electrode layer 4 is an alloy electrode of aluminum and a small amount of lithium. The electrode layer 4 can be easily formed on the surface including the light emitting layer 3 formed on the substrate 1, for example, by a vapor deposition technique.

[0072] Regardless of which of the coating method and vapor deposition method is employed, it is preferable to interpose a nother layer between the electrode layer and the light emitting layer.

[0073] Examples of materials that can form the buffer layer include alkali metal compounds such as lithium fluoride, alkaline earth metal compounds such as magnesium fluoride, and oxides such as aluminum oxide, 4, 4, Biscarbazole biphenyl (Cz-TPD). In addition, as a material for forming a noffer layer formed between an anode such as ITO and an organic layer, for example, m-MTDATA (4, 4 ,, 4 "-tris (3-methylphenol-aminoamine) ) Triphenylamine), phthalocyanine, polyarine, polythiophene derivatives, inorganic oxides such as molybdenum oxide, ruthenium oxide, vanadium oxide, and lithium fluoride. By appropriate selection, the driving voltage of the organic EL element, which is a light emitting element, can be reduced, the quantum efficiency of light emission can be improved, and the emission luminance can be improved.

Next, a second example of the light emitting device according to the present invention is shown in the drawing. FIG. 2 is an explanatory view showing a cross section of a light emitting device which is a multilayer organic EL device.

As shown in FIG. 2, the light-emitting element B has a transparent electrode 2 and a hole transport layer on the surface of the substrate 1.

5, the light emitting layers 3a and 3b, the electron transport layer 6 and the electrode layer 4 are laminated in this order.

[0076] The substrate 1, the transparent electrode 2, and the electrode layer 4 are the same as those in the light-emitting element A shown in FIG.

[0077] The light emitting layer in the light emitting device B shown in FIG. 2 includes a light emitting layer 3a and a light emitting layer 3b. The light emitting layer 3a is a low molecular weight light emitting compound and Z or a light emitting polymer according to the present invention. Contains compounds. The light emitting layer 3a may be a vapor deposition film or a polymer film. The light emitting layer 3b is a DPVBi layer. This DPVBi layer has a host material function.

[0078] The hole transport material contained in the hole transport layer 5 is a triphenylamine compound. Products such as N, N, —Diphenyl-N, N, —Di (m-tolyl) -benzidine (TPD), and a NPD, hydrazone compounds, stilbene compounds, heterocyclic compounds, π-electron starburst positive Examples thereof include pore transport materials.

[0079] The electron transport material contained in the electron transport layer 6 includes, for example, 2- (4-tert-butylphenol) -5- (4-biphenyl) -1, Examples include oxadiazole derivatives such as 3,4-oxoxadiazole, 2,5 bis (1 naphthyl) 1,3,4 oxaziazole, and 2,5 bis (5 'tert butyl-2'-benzoxazolyl) thiophene . Further, as the electron transporting substance, for example, a metal complex material such as quinolinol aluminum complex (Alq3), benzoquinolinol beryllium complex (Bebq2) can be preferably used.

In the light emitting device B in FIG. 2, the electron transport layer 6 contains Alq3.

[0081] The thickness of each layer is the same as that of a known multilayer organic EL element with a conventional force.

The light emitting element B shown in FIG. 2 operates in the same manner as the light emitting element A shown in FIG. 1, and emits light. Therefore, the light-emitting element B shown in FIG. 2 has the same application as the light-emitting element A shown in FIG.

FIG. 3 shows a third example of the light emitting device according to the present invention. FIG. 3 is an explanatory view showing a cross section of a light emitting device which is a multilayer organic EL device.

A light-emitting element C shown in FIG. 3 is formed by laminating a transparent electrode 2, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 8 and an electrode layer 4 in this order on the surface of a substrate 1.

The light-emitting element C shown in FIG. 3 is the same as the light-emitting element B.

FIG. 4 shows another example of the light emitting element. The light emitting element D shown in FIG. 4 is formed by laminating a substrate 1, an electrode 2, a hole transport layer 5, a light emitting layer 3 and an electrode layer 4 in this order.

In addition to the light emitting device shown in FIGS. 1 to 4, a hole transport layer containing a hole transport material is formed between a positive electrode that is a transparent electrode and a cathode that is an electrode layer formed on a substrate. And a low-molecular-weight organic light-emitting device (for example, between an anode and a cathode) formed by laminating a low-molecular light-emitting compound and an electron-transporting light-emitting layer containing Z or a light-emitting polymer compound according to the present invention. A two-layer color comprising a hole transport layer and a light emitting layer containing a low molecular weight light emitting compound and a Z or light emitting polymer compound and a host dye as a guest dye. Element-doped light-emitting element), a hole transport layer containing a hole transport material between the anode and the cathode, a low-molecular light-emitting compound and Z or a light-emitting polymer compound and an electron transport material according to the present invention A two-layer organic light-emitting device formed by laminating an electron-transporting light-emitting layer formed by co-evaporation (for example, a hole transport layer between an anode and a cathode, and a low-molecular-weight organic compound according to the present invention as a guest dye). A two-layer dye-doped organic light-emitting device comprising a light-emitting compound and Z or an electron-transporting light-emitting layer containing a light-emitting polymer compound and a host dye, and a hole transport layer between the anode and the cathode Examples thereof include a three-layer organic light-emitting device formed by laminating a light-emitting layer and an electron transport layer containing a low-molecular light-emitting compound and Z or a light-emitting polymer compound according to the present invention.

[0088] The electron-transporting light-emitting layer in this light-emitting element is usually composed of 50 to 80% polyvinyl carbazole (PVK), an electron-transporting light-emitting agent 5 to 40%, and the low-molecular weight according to the present invention. When formed with the light-emitting compound and Z or the light-emitting polymer compound 0.01 to 20% (by weight), light emission of a color corresponding to the structure of the light-emitting compound occurs with high luminance.

[0089] The light emitting layer preferably contains rubrene as a sensitizer, and particularly contains rubrene and Alq3 !.

The light emitting device using the low molecular weight light emitting compound and Z or the light emitting polymer compound according to the present invention can be generally used as, for example, a direct current driving type organic EL device, and a nors driving type organic EL device. It can also be used as an EL element and an AC drive type organic EL element.

Example

[0091] (Example 1)

In Example 1, a light emitting compound having a structure represented by the following formula (10) was produced. Below, a manufacturing procedure is demonstrated for every reaction.

[0092] [Chemical 22]

[Production Example of Compound (1 A)]

Compound (1A) was produced according to the following reaction formula (1-1) _c

[0094] [Chemical 23]

(1 1)

(1A)

[0095] The above methylfluorene (38 g) and aluminum chloride (29 g) were charged into a three-necked flask, and further, 20 ml of sodium acetyl chloride and 15 ml of sulfurous carbon were added. By heating the inside of the flask to 60 ° C, the reaction was started and continued for 3 hours. After 3 hours, heating was stopped and the mixture was allowed to cool to return the reaction product solution in the flask to room temperature. A light pink composition was obtained by subjecting the reaction product at room temperature to extraction with black mouth form and distillation using an evaporator.

[0096] Fig. 5 and Fig. 6 show the NMR ^ vector chart and IR spectrum chart of the obtained composition, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained compositional power compound (1A) (methyl ketone fluorene) was obtained.

[Production Example of Compound (1B)]

Compound (1B) was produced according to the following reaction formula (12).

[0098] [Chemical 24]

0, o

ヽ / COCHs (1-2)

(1A) (IB) [0099] 22 g of the above compound (1 A) (methyl ketone fluorene), 250 ml of methanol, and 500 ml of sodium hypochlorite solution (effective chlorine 5%) were charged into a three-necked eggplant flask. The three-necked eggplant flask was heated in a 75 ° C hot water bath. This heating was performed for 3 hours and then cooled with water. HC1 was added dropwise until the pH value reached 1 to 2, and washed with water to obtain 17.02 g of composition.

[0100] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 7 and 8, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed to be the obtained compositional force compound (1B).

[0101] [Production Example of Compound (1C)]

Compound (1C) was produced according to the following reaction formula (13).

[0102] [Chemical 25]

,,, {1,

[0103] 100 ml of the above compound (IB) Ugtl, 4 dioxane and 75 ml of chlorochloride were put together with zeolite in an eggplant flask. The eggplant flask was heated by an oil bath at 110 ° C. This heating was performed for 4 hours and then cooled with water. The obtained reaction product was dissolved in 300 ml of THF (an abbreviation of tetrahydrofuran, the same shall apply hereinafter), followed by filtration with filter paper. Then, distillation with an evaporator and drying with a vacuum pump were performed at 50 ° C. for 1 hour to obtain 16.6 g of a composition.

[0104] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 9 and 10, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (1C).

[Production Example of Compound (1D)]

Compound (1D) was produced according to the following reaction formula (1-4).

[0106] [Chemical 26]

(丄 ―4)

(ID)

[0107] 16.6 g of the above compound (1C), 13.4 ml of pyridine, and 2 lml of hydrazine were charged into a three-necked eggplant flask. This three-necked eggplant flask was heated in an oil bath at 70 ° C. This heating was carried out for 4 hours while adding dropwise THF40 Oml, followed by cooling with water. Then, distillation with an evaporator and drying with a vacuum pump were performed at 50 ° C. for 1 hour to obtain 15. lg of a composition.

[0108] Fig. 11 and Fig. 12 show the NMR ^ vector chart and IR spectrum chart of the obtained composition, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (1D).

[Production Example of Compound (1E)]

Compound (1E) was produced according to the following reaction formula (15).

[0110] [Chemical 27]

[0111] 2. Compound (1D) 2. Og, pyrenecarboxylic acid 1.9 g, N-methylpyrrolidone 32 ml, phosphite diphenyl 5.25 g, sodium chloride 2. lg, pyridine 20 ml Poured into flask. The three-necked eggplant flask was heated with a 120 ° C. oil bath. After cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain composition 3. Og.

[0112] The NMR ^ vector chart and IR spectrum chart of the obtained composition are respectively shown. These are shown in FIGS. 13 and 14. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (1E).

[Production Example of Compound (1F)]

Compound (1F) was produced according to the following reaction formula (16).

[0114] [Chemical 28]

(IE)

[0115] The above compound (IE) 3. Og, 1,4 dioxane 100ml and POC1 50ml

Three

And zeolite were charged into the eggplant flask. The eggplant flask was heated in an oil bath of 12 F0 ° C for 13 hours. After cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain a composition 2. Og.

[0116] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 15 and 16, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (1F).

[0117] Thereafter, the compound (1F) was dissolved in toluene to a concentration of lmgZL to prepare a sample solution. This sample solution was loaded into an F-4500 spectrofluorometer manufactured by Shimadzu Corporation, and the fluorescence spectrum was measured under the following conditions. The obtained fluorescence spectrum is shown in FIG. From this fluorescence spectrum, it was confirmed that the compound (1F) emitted blue light.

[0118] Measurement conditions

Measurement mode Wavelength scan

Excitation wavelength 365nm

Fluorescence start wavelength 400nm

Fluorescence end wavelength 700nm

Scan speed 1200nm / min Excitation side slit 5. Onm

Fluorescent side slit 5. Onm

Photomultiplier voltage 700V

[0119] (Example 2)

In Example 2, a light-emitting polymer compound having a structure represented by the following formula (2-0) was produced. Below, a manufacturing procedure is demonstrated for every reaction.

[0120] [Chemical 29]

[Production Example of Compound (2A)]

Compound (2A) was produced according to the following reaction formula (2-1).

[0122] [Chemical 30]

CsHi?

S0C12

HOOC <O W o> C00H C10C (O W o) C0C1

(2A)

[0123] 30 g of the above carboxylic acid, 450 ml of 1,4 dioxane, 10 ml of pyridine, and 150 ml of chlorochloride were charged into a three-necked eggplant flask. The eggplant flask was heated by an oil bath at 100 ° C. This heating was performed for 4 hours and then cooled with water. The obtained reaction product was dissolved in 300 ml of THF and filtered through filter paper. Then, distillation with an evaporator and drying with a vacuum pump were performed at 50 ° C. for 1 hour to obtain 31. Og of a light brown yellow composition.

[0124] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 18 and 19, respectively. These NMR ^ vector chart and IR ^ vector chart From the results, it was confirmed that the obtained composition was the compound (2A).

[Production Example of Compound (2B)]

Compound (2B) was produced according to the following reaction formula (2-2).

[0126] [Chemical 31]

(2Bj

[0127] 3.81 g of the above-mentioned rubazole hydrazide and 1.29 g of pyridine were put into a three-necked eggplant flask and dissolved in 200 ml of THF. 7 g of compound (2A) and 400 ml of THF were mixed and instilled into a three-necked eggplant flask. The eggplant flask was heated by an oil bath at 70 ° C. This heating was performed for 1.5 hours and then cooled with water. The obtained reaction product was dissolved in 300 ml of THF and filtered through filter paper. Then, distillation with an evaporator and drying with a vacuum pump were performed at 50 ° C. for 0.5 hour to obtain a composition 10. Og.

[0128] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Fig. 20 and Fig. 21, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (2B).

[Production Example of Compound (2C)]

Compound (2C) was produced according to the following reaction formula (2-3).

[0130] [Chemical 32] C1

(2B)

CH ₂ E¾C1

CsHi7 C¾¾7

N

To H2 N¾ / V

Difficult thigh 0C B O〉 C0NHNH0d o I I o (2-3)

(2C)

[0131] 4.3 ml of hydrazine and 3.13 ml of pyridine were charged into a three-necked eggplant flask. Thereafter, 10 g of the above compound (2B) and 500 ml of THF were mixed and instilled into a three-necked eggplant flask. The eggplant flask was heated in an oil bath at 70 ° C. This heating was performed for 4 hours and then cooled with water. Then, extraction with black mouth form, distillation with an evaporator, and drying with a vacuum pump were carried out at 50 ° C. for 0.5 hour to obtain 7.2 g of a composition.

[0132] The NMR vector chart and IR spectrum chart of the resulting composition are shown in FIGS. 22 and 23, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (2C).

[Production Example of Compound (2D)]

Compound (2D) was produced according to the following reaction formula (2-4).

[0134] [Chemical 33]

l

(0

O) — Λ O

(20

( twenty four )

[0135] The above compound (2C) 6. Og and pyrenecarboxylic acid 2. Og, N-methylpyrrolidone 64 ml, diphosphite 10.5 g, sodium chloride 4.2 g, pyridine 40 ml Poured into flask. This three-necked eggplant flask was heated in an oil bath at 120 ° C. for 30 hours. After cooling with water, Nutsche treatment, washing with methanol, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain composition 8. Og.

[0136] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 24 and 25, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (2D).

[Production Example of Compound (2E)]

Compound (2E) was produced according to the following reaction formula (2-5).

[0138] [Chemical 34]

(2E)

[0139] The above compound (2D) 8. Og, 150 ml of 1,4 dioxane and 75 ml of POC1

Three

And zeolite were charged into the eggplant flask. The eggplant flask was heated in an oil bath at 120 ° C. for 7 hours. After cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain 5.2 g of a composition. And it was made to melt | dissolve in black mouth form, and column separation was carried out, and the composition 1. Og was obtained.

[0140] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 26 and 27, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (2E).

[0141] [Production Example of Compound (2F)]

Compound (2F) was produced according to the following reaction formula (2-6).

[0142] [Chemical 35]

(2E)

(2F)

[0143] The above compound (2E) 1. Og, 100 ml of 1,4 dioxane, 50 ml of absolute ethanol, 0.75 g of KOH, and zeolite were charged into an eggplant flask. The eggplant flask was heated in an oil bath at 100 ° C for 4 hours. After cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain 0.35 g of the composition.

[0144] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 28 and 29, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (2F).

[Example of production of polymer compound (2G)]

A polymer compound (2G) was produced according to the following reaction formula (2-7).

[0146] [Chemical 36]

t2F)

[0147] 0.2 g of the compound (2F) and 9 ml of DMF (abbreviation of dimethylformamide, the same applies hereinafter) were charged into a nurse flask. Then, 0.7 g of a solution obtained by mixing 5 mg of AIBN (abbreviation for azobisisobuty-tolyl, hereinafter the same) as a polymerization initiator and 5 g of DMF was put into an eggplant flask. In addition, 5 ml of chlorobenzene was also charged into the eggplant flask. The eggplant flask was heated in a 145 ° C oil bath for 120 hours. After cooling with water, distillation with an evaporator, vacuum pump distillation, and 70 ° C were performed for 1 hour, followed by washing with methanol and drying with a vacuum pump to obtain 0.2 g of a composition.

[0148] The NMR ^ vector chart and IR spectrum chart of the obtained composition are shown in Figs. 30 and 31, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was a polymer compound (2G).

[0149] Thereafter, the fluorescence spectrum of the polymer compound (2G) was measured in the same manner as in Example 1. The obtained fluorescence spectrum is shown in FIG. From this fluorescence spectrum, it was confirmed that the polymer compound (2G) emitted blue light.

[0150] (Example 3)

In Example 3, a light-emitting polymer compound having a structure represented by the following formula (3-0) was produced. Below, a manufacturing procedure is demonstrated for every reaction.

[0151] [Chemical 37]

[0152] [Production Example of Compound (3A)]

Compound (3A) was produced according to the following reaction formula (3-1).

[0153] [Chemical 38]

(3A)

[0154] 18 g of the chloride represented by the left side of the above formula (3-1) and 100 ml of sodium chloride were added to an eggplant flask together with zeolite. The eggplant flask was heated by an oil bath at 90 ° C. This heating was performed for 4 hours and then cooled with water. The obtained reaction product was dissolved in 800 ml of THF and filtered through filter paper. Then, distillation with an evaporator and drying with a vacuum pump were performed at 50 ° C. for 1 hour to obtain a composition 19. Og.

[0155] The NMR ^ vector chart and IR spectrum chart of the obtained composition are shown in Figs. 33 and 34, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (3A).

[Production Example of Compound (3B)]

Compound (3B) was produced according to the following reaction formula (3-2).

[0157] [Chemical 39] 3-2)

2

3A) (3B)

[0158] 3.91 ml of pyridine and 6.1 ml of hydrazine were charged into a three-necked eggplant flask. The three-necked eggplant flask was heated in an oil bath at 70 ° C. This heating was carried out for 4 hours while dropwise adding 300 ml of TH F containing 5.4 g of the above compound (3A), and then cooled with water. Chloroform extraction was performed, followed by distillation with an evaporator and drying with a vacuum pump at 50 ° C. for 0.5 hour to obtain 4.5 g of a composition.

[0159] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 35 and 36, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (3B).

[Production Example of Compound (3C)]

Compound (3C) was produced according to the following reaction formula (3-3).

[0161] [Chemical 40]

(3-3) The above compound (3B) 2. Og and pyrenecarboxylic acid 1.68g, N-methylpyrrolidone 32ml, diphosphite 5.25g, sodium chloride 2. lg and pyridine 20ml It poured into the eggplant flask. This three-necked eggplant flask was heated in a 120 ° C. oil bath for 17 hours. And after cooling with water, Nutsche treatment, methanol washing, drying by vacuum pump 50 ° C After 1 hour, 0.68 g of the composition was obtained.

[0163] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 37 and 38, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (3C).

[Production Example of Compound (3D)]

Compound (3D) was produced according to the following reaction formula (3-4).

[0165] [Chemical 41]

--■ (3-4)

[0166] 0.68 g of the above compound (3C), 150 ml of 1,4 dioxane, 75 ml of POC1 and zeolite

Three

I put it in Lasco. The eggplant flask was heated in an oil bath at 120 ° C. for 14 hours. Then, after cooling with water, Nutsche treatment and methanol washing were performed to obtain 0.2 g of the composition.

[0167] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 39 and 40, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (3D).

[Production Example of Compound (3E)]

Compound (3E) was produced according to the following reaction formula (3-5).

[0169] [Chemical 42]

3D) (3E)

(3-5)

[0170] 0.2 g of the above compound (3D), 200 ml of 1,4 dioxane, 100 ml of ethanol, 1.2 g of KOH, and zeolite were charged into an eggplant flask. The eggplant flask was heated in a 100 ° C oil bath for 14 hours. After cooling with water, Nutsche treatment and methanol washing were performed to obtain 0.1 lg of composition.

[0171] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 41 and 42, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (3E).

[Production Example of Polymer Compound (3F)]

A polymer compound (3F) was produced according to the following reaction formula (3-6).

[0173] [Chemical 43]

(3E) (3F)

3 6) 0.1 lg of the above compound (3E) and 9 ml of DMF were put into an eggplant flask. Then, 0.07 g of a solution obtained by mixing 5 mg of AIBN and 5 g of DMF was put into the eggplant flask. In addition, 5 ml of orthodichlorobenzene (hereinafter sometimes abbreviated as ODB) was also charged into the eggplant flask. The eggplant flask was heated in an oil bath at 170 ° C. for 120 hours. After cooling with water, distillation with an evaporator, vacuum pump distillation, 70 ° C for 1 hour, then methanol Washing and drying with a vacuum pump were performed to obtain 0.2 g of a composition.

[0175] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 43 and 44, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was a polymer compound (3F).

[0176] Thereafter, the fluorescence spectrum of the polymer compound (3F) was measured in the same manner as in Example 1. The obtained fluorescence spectrum is shown in FIG. From this fluorescence spectrum, it was confirmed that the polymer compound (3F) emitted white light.

[0177] (Example 4)

In Example 4, a light emitting compound having a structure represented by the following formula (40) was produced. Below, a manufacturing procedure is demonstrated for every reaction.

[0178] [Chemical 44]

[Production Example of Compound (4A)]

Compound (4A) was produced according to the following reaction formula (41).

[0180] [Chemical 45]

* · · (4-1)

(4A)

[0181] The above compound, pyridine and hydrazine were charged into a three-necked eggplant flask. This three-necked eggplant flame was heated in a 70 ° C oil bath. This heating was performed for 4 hours while adding 400 ml of THF dropwise, and then cooled with water. Then, distillation with an evaporator and drying with a vacuum pump were performed at 50 ° C. for 1 hour to obtain 1.5 g of the composition (4A). [0182] [Production Example of Compound (4B)]

Compound (4B) was produced according to the following reaction formula (4 2).

[0183] [Chem 46]

(4A) (4B)

[0184] 1.5 g of the above compound (4A), pyrenecarboxylic acid, 2. Og, 1-methyl-2-pyrrolidone, 40 ml, diphenyl phosphite, 3 g, lithium chloride, 4.2 g, and pyridine, 30 ml were charged into a three-necked eggplant flask. . This three-necked eggplant flask was heated in an oil bath at 120 ° C. for 32 hours. After cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain 2.4 g of a composition.

[0185] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 46 and 47, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (4B).

[Production Example of Compound (4C)]

Compound (4C) was produced according to the following reaction formula (43).

[0187] [Chemical 47]

'--3

(4B) (4C)

[0188] 2. Compound (4B) 2. Og, 1,4 dioxane 200 ml, POC1 100 ml and zeolite

Three

I put it in Lasco. The eggplant flask was heated in an oil bath at 115 ° C. for 25 hours. After cooling with water, Nutsche treatment and methanol washing were performed to obtain 1.75 g of composition. It was.

[0189] The NMR ^ vector chart and IR spectrum chart of the obtained composition are shown in Figs. 48 and 49, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (4C).

[0190] Thereafter, the fluorescence spectrum of compound (4C) was measured in the same manner as in Example 1. The obtained fluorescence spectrum is shown in FIG. This fluorescence spectrum indicates that the compound

(4C) was confirmed to emit blue light.

[0191] (Example 5)

In Example 5, a light emitting compound having a structure represented by the following formula (5-0) was produced. Below, a manufacturing procedure is demonstrated for every reaction.

[0192] [Chemical 48]

[Production Example of Compound (5A)]

Compound (5A) was produced according to the following reaction formula (5-1).

[0194] [Chemical 49]

(5 — 1)

5.47 g of the above pyrenecarboxylic acid, 300 ml of 1,4 dioxane, 125 ml of chlorochloride and 20 ml of pyridine were charged into an eggplant flask. The eggplant flask was heated with an oil bath at 110 ° C. This heating was performed for 3.5 hours and then cooled with water. The obtained reaction product was dissolved in 600 ml of THF and filtered through filter paper. And according to the evaporator Distillation with a vacuum pump and drying at 50 ° C. for 1 hour gave composition 8. Og.

[0196] Fig. 51 and Fig. 52 show the NMR ^ vector chart and IR spectrum chart of the obtained composition, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (4A).

[Production Example of Compound (5B)]

Compound (5B) was produced according to the following reaction formula (5-2).

[0198] [Chemical 50]

[0199] 3.91 ml of pyridine and 6.1 ml of hydrazine were charged into a three-necked eggplant flask. The three-necked eggplant flask was heated in an oil bath at 70 ° C. The above compound (5A) 5. This heating was performed for 5 hours while adding dropwise 500 ml of TH F containing Og, and then cooled with water. Nutsche treatment, washing with methanol, and drying with a vacuum pump were carried out at 50 ° C. for 0.5 hour to obtain a composition 3. Og.

[0200] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 53 and 54, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (5B).

[0201] [Production Example of Compound (5C)]

Compound (5C) was produced according to the following reaction formula (5-3).

[0202] [Chemical 51]

(5B) (50

[0203] 1.2 g of the above compound (5B), pyrenecarboxylic acid 1. 14 g, 1-methyl-2-pyrrolidone 40 ml, diphenyl phosphite 2 g, lithium chloride 4.2 g, and pyridine 30 ml were charged into a three-necked eggplant flask. did. This three-necked eggplant flask was heated in an oil bath at 120 ° C. for 26 hours. Then, after cooling with water, Nutsche treatment, methanol washing, and drying at 50 ° C. with a vacuum pump were performed for 1 hour to obtain composition 2. Og.

[0204] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Figs. 55 and 56, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (5C).

[Production Example of Compound (5D)]

Compound (5D) was produced according to the following reaction formula (5-4).

[0206] [Chemical 52]

(5C) (5D)

[0207] 1.5 g of the above compound (5C), 200 ml of 1,4 dioxane, 100 ml of POC1 and zeolite

Three

I put it in Lasco. The eggplant flask was heated in an oil bath at 115 ° C. for 18 hours. Then, after cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed to obtain 1.26 g of a yellow brown composition.

[0208] The NMR ^ vector chart and IR spectrum chart of the obtained composition were respectively shown. This is shown in FIGS. 57 and 58. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (5D).

[0209] Thereafter, the fluorescence spectrum of compound (5D) was measured in the same manner as in Example 1. The obtained fluorescence spectrum is shown in FIG. This fluorescence spectrum indicates that the compound

(5D) was confirmed to emit white light.

[0210] (Example 6)

In Example 6, a light-emitting polymer compound having a structure represented by the following formula (6-0) was produced. Below, a manufacturing procedure is demonstrated for every reaction.

[0211] [Chemical 53]

[0212] [Production Example of Compound (6A)]

Compound (6A) was produced according to the following reaction formula (6-1).

[0213] [Chemical 54]

Compound (5B) obtained in Example 5 above 1. Og, 0.37 g of pyridine, and 600 ml of THF were charged into a three-necked eggplant flask. Then, 0.6 g of the above chloride and 50 ml of THF were mixed and dropped into a three-necked eggplant flask. This three-necked eggplant flask was heated in an oil bath at 70 ° C. for 13 hours. Then, it cooled with water and filtered using the large membrane filter. Then wash with water, wash with methanol, dry with vacuum pump at 50 ° C for 1 hour, composition 0.6 g of product was obtained.

[0215] The NMR ^ vector chart and IR spectrum chart of the resulting composition are shown in Fig. 60 and Fig. 61, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (6A).

[Production Example of Compound (6B)]

Compound (6B) was produced according to the following reaction formula (6-2).

[0217] [Chemical 55]

[0218] The above compound (6A) 3. Og, 1,4 dioxane 100 ml, POC1 50 ml

Three

And zeolite were charged into the eggplant flask. This eggplant flask is placed in a 100 ° C oil bath.

Heated for 40 hours. After cooling with water, Nutsche treatment, methanol washing, and drying with a vacuum pump were performed at 50 ° C for 1 hour to obtain 0. lg of a composition.

[0219] The NMR ^ vector chart and IR spectrum chart of the obtained composition are shown in FIGS. 62 and 63, respectively. From these NMR ^ vector chart and IR ^ vector chart, it was confirmed that the obtained composition was the compound (6B).

[0220] [Production example of polymer compound (6C)]

A polymer compound (6C) was produced according to the following reaction formula (6-3).

[0221] [Chemical 56]

(6B) (6C)

[0222] 0.02 g of the above compound (6B) and 2 g of DMF were charged into an eggplant flask. Then, 0.2 g of a solution obtained by mixing 5 mg of AIBN and 5 g of DMF was put into the eggplant flask. ODB5ml was also added to the eggplant flask. This eggplant flask was heated in an oil bath at 140 ° C. for 150 hours. After cooling with water, distillation with an evaporator, vacuum pump distillation and 70 ° C were performed for 1 hour, followed by washing with methanol and drying with a vacuum pump to obtain 0.2 g of a composition.

[0223] Fig. 64 shows an IR ^ vector chart of the obtained composition. From the IR ^ spectrum chart, it was confirmed that the obtained composition was a polymer compound (6C).

[0224] Thereafter, the fluorescence spectrum of the polymer compound (6C) was measured in the same manner as in Example 1. The obtained fluorescence spectrum is shown in FIG. From this fluorescence spectrum, it was confirmed that the polymer compound (6C) emitted blue light.

Brief Description of Drawings

FIG. 1 is an explanatory view showing a light emitting device as an example according to the present invention.

FIG. 2 is an explanatory view showing a light emitting device as another example according to the present invention.

FIG. 3 is an explanatory view showing a light emitting device as another example according to the present invention.

FIG. 4 is an explanatory view showing a light emitting device as still another example according to the present invention.

FIG. 5 is an NMR spectrum chart showing the compound (1A) synthesized in the example of the present invention.

FIG. 6 is an IR ^ vector chart showing the compound (1A) synthesized in the example of the present invention.

FIG. 7 is a NMR vector chart showing the compound (1B) synthesized in the example of the present invention.

FIG. 8 is an IR spectrum chart showing the compound (1B) synthesized in the example of the present invention. It is

FIG. 9 is an NMR spectrum chart showing the compound (1C) synthesized in the example of the present invention.

[FIG. 10] FIG. 10 is an IR ^ vector chart showing the compound (1C) synthesized in the example of the present invention.

FIG. 11 is an NMR spectrum chart showing the compound (1D) synthesized in the example of the present invention.

FIG. 12 is an IR spectrum chart showing the compound (1D) synthesized in the example of the present invention.

FIG. 13 is an NMR spectrum chart showing the compound (1E) synthesized in the example of the present invention.

FIG. 14 is an IR ^ vector chart showing a composite (1E) synthesized in an example of the present invention.

FIG. 15 is an NMR spectrum chart showing the compound (1F) synthesized in the example of the present invention.

FIG. 16 is an IR ^ vector chart showing a composite (1F) synthesized in an example of the present invention.

FIG. 17 is a fluorescence spectrum chart showing the compound (1F) synthesized in the example of the present invention.

FIG. 18 is a NMR spectrum chart showing the compound (2A) synthesized in the example of the present invention.

[FIG. 19] FIG. 19 is an IR ^ vector chart showing the compound (2A) synthesized in the example of the present invention.

FIG. 20 is an NMR spectrum chart showing the compound (2B) synthesized in the example of the present invention.

FIG. 21 is an IR spectrum chart showing the compound (2B) synthesized in the example of the present invention.

[FIG. 22] FIG. 22 shows NMR spectra showing the compound (2C) synthesized in the example of the present invention. It is a Nore chart.

FIG. 23 is an IR ^ vector chart showing a composite (2C) synthesized in an example of the present invention.

FIG. 24 is an NMR spectrum chart showing a compound (2D) synthesized in an example of the present invention.

FIG. 25 is an IR spectrum chart showing the compound (2D) synthesized in the example of the present invention.

FIG. 26 is an NMR spectrum chart showing the compound (2E) synthesized in the example of the present invention.

FIG. 27 is an IR ^ vector chart showing the compound (2E) synthesized in the example of the present invention.

FIG. 28 is an NMR spectrum chart showing the compound (2F) synthesized in the example of the present invention.

FIG. 29 is an IR ^ vector chart showing the compound (2F) synthesized in the example of the present invention.

FIG. 30 is an NMR spectrum chart showing the polymer compound (2G) synthesized in the example of the present invention.

FIG. 31 is an IR spectrum chart showing the polymer compound (2G) synthesized in the example of the present invention.

FIG. 32 is a fluorescence spectrum chart showing the polymer compound (2G) synthesized in the example of the present invention.

FIG. 33 is a NMR spectrum chart showing the compound (3A) synthesized in the example of the present invention.

FIG. 34 is an IR ^ vector chart showing a composite (3A) synthesized in the example of the present invention.

FIG. 35 is an NMR spectrum chart showing the compound (3B) synthesized in the example of the present invention.

FIG. 36 is an IR spectrum showing the compound (3B) synthesized in the example of the present invention. It is a chart.

FIG. 37 is a NMR spectrum chart showing the compound (3C) synthesized in the example of the present invention.

FIG. 38 is an IR ^ vector chart showing a composite (3C) synthesized in an example of the present invention.

FIG. 39 is an NMR spectrum chart showing the compound (3D) synthesized in the example of the present invention.

FIG. 40 is an IR spectrum chart showing the compound (3D) synthesized in the example of the present invention.

FIG. 41 is an NMR spectrum chart showing the compound (3E) synthesized in the example of the present invention.

FIG. 42 is an IR ^ vector chart showing a composite (3E) synthesized in an example of the present invention.

FIG. 43 is an NMR spectrum chart showing the polymer compound (3F) synthesized in the example of the present invention.

FIG. 44 is an IR spectrum chart showing the polymer compound (3F) synthesized in the example of the present invention.

FIG. 45 is a fluorescence spectrum chart showing a polymer compound (3F) synthesized in an example of the present invention.

FIG. 46 is an NMR spectrum chart showing the compound (4B) synthesized in the example of the present invention.

FIG. 47 is an IR spectrum chart showing the compound (4B) synthesized in the example of the present invention.

FIG. 48 is an NMR spectrum chart showing the compound (4C) synthesized in the example of the present invention.

FIG. 49 is an IR ^ vector chart showing the compound (4C) synthesized in the example of the present invention.

[FIG. 50] FIG. 50 shows a fluorescent spectrum showing a compound (4C) synthesized in an example of the present invention. It is a Nore chart.

FIG. 51 is a NMR spectrum chart showing the compound (5A) synthesized in the example of the present invention.

FIG. 52 is an IR ^ vector chart showing a composite (5A) synthesized in an example of the present invention.

FIG. 53 is an NMR spectrum chart showing the compound (5B) synthesized in the example of the present invention.

FIG. 54 is an IR spectrum chart showing the compound (5B) synthesized in the example of the present invention.

FIG. 55 is a NMR spectrum chart showing the compound (5C) synthesized in the example of the present invention.

FIG. 56 is an IR ^ vector chart showing a composite (5C) synthesized in an example of the present invention.

FIG. 57 is an NMR spectrum chart showing the compound (5D) synthesized in the example of the present invention.

FIG. 58 is an IR spectrum chart showing the compound (5D) synthesized in the example of the present invention.

FIG. 59 is a fluorescence spectrum chart showing the composite (5D) synthesized in the example of the present invention.

FIG. 60 is an NMR spectrum chart showing the compound (6A) synthesized in the example of the present invention.

FIG. 61 is an IR ^ vector chart showing a composite (6A) synthesized in an example of the present invention.

FIG. 62 is an NMR spectrum chart showing the compound (6B) synthesized in the example of the present invention.

FIG. 63 is an IR spectrum chart showing the compound (6B) synthesized in the example of the present invention.

FIG. 64 shows an IR spectrum showing the polymer compound (6C) synthesized in the example of the present invention. It is a ktonore chart.

FIG. 65 is a fluorescence spectrum chart showing a polymer compound (6C) synthesized in an example of the present invention.

Explanation of symbols

1 Board

2 Transparent electrode

3 Light emitting layer

3a Light emitting layer

3b Light emitting layer

4 Electrode layer

5 hole transport layer

6 Electron transport layer

8 Electron transport layer

A Light-emitting element

B Light emitting element

C Light-emitting element

D Light emitting element

Claims

The scope of the claims

A light-emitting compound having a structure represented by the following formula (1):

[In the formula (1), A represents any group represented by the following formulas (2) to (13). ]

[Chemical 2]

[Chemical 3]

[Chemical 4]

c R!

2 Unification 5]

H

( Five )

[In the formula ( ⁵ ), R represents H or a methyl group. ]

[Chemical 6]

[Chemical 7]

[3] A light-emitting polymer compound having a structure represented by the following formula (15):

[In the formula (15), R ² represents H or a methyl group. ]

A light-emitting polymer compound having a repeating unit structure represented by the following formula (16):

[In the formula (16), R represents H or a methyl group. ]

A light emitting layer comprising a light emitting layer containing the light emitting compound according to claim 1 or the light emitting polymer compound according to any one of claims 2 to 4 between a pair of electrodes. element.