JP2007088300A - LIGHT EMITTING DEVICE, LIGHTING DEVICE, AND IMAGE DISPLAY DEVICE - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a light emitting device having a high luminance, emitting a light closer to a natural light, and having a few deviation in luminescent color caused by an increase and a decrease in emitted light intensity. <P>SOLUTION: The light emitting device 1 comprises a light source 2 for emitting the light having a peak wavelength of 350 nm to 420 nm, and a fluorescent material 3 for absorbing at least a part of the light from the light source 2 and emitting the light having a wavelength different from that of the source 2. One or more organic fluorescent materials are used as the fluorescent material 3, a luminous efficiency of the device 1 is not less than 20 lm/W, and an average color rendering rating index Ra is not less than 80. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a light emitting device, and a lighting device and an image display device using the same, and more particularly to a light emitting device combining a semiconductor light emitting element and an organic phosphor, and a lighting device and an image display device using the same. .

  2. Description of the Related Art Conventionally, light emitting devices in which light from a discharge lamp or a semiconductor light emitting element is color-converted with a phosphor have been used in lighting devices and display devices. These light emitting devices mix blue, green, and red phosphors and emit light of white or any color. In recent years, various studies have been made in search of higher color rendering or color reproducibility. ing. Among them, light emitting devices using semiconductor light emitting elements such as light emitting diodes (LEDs) and laser diodes (LDs) have high luminous efficiency and do not contain harmful substances such as mercury. Therefore, LEDs and LDs are combined with phosphors. Development of light-emitting devices, in particular, light-emitting devices using LEDs and LDs in the near-ultraviolet region to the visible region of 360 nm or more with high efficiency has been actively conducted.

However, since the emission wavelength of LEDs and LDs is longer than 360 nm, red inorganic phosphors such as yttrium oxide europium complexes (Y ₂ O ₃ : Eu) used in fluorescent lamps and the like emit sufficient light. I can't get it. Thus, LED and LD and Y ₂ O _3: even by using the red inorganic phosphor such as Eu, it was not possible to obtain a high-brightness light-emitting device.

Therefore, a light emitting device is proposed in which an LED or LD is combined with an organic phosphor made of a rare earth element ion complex such as europium (Eu) having a β-diketone anion as a ligand (Patent Document 1 and Patent). Reference 2). This is reported as a device that can efficiently absorb visible light from near ultraviolet light and obtain high-luminance emission compared to fluorescent lamps using red inorganic phosphors such as Y ₂ O ₃ : Eu. Has been.

However, as reported in Patent Document 1 and Patent Document 2, a red organic phosphor composed of a rare earth element ion complex having an anion of β-diketone as a ligand exhibits a performance that easily causes photodegradation, and has a light emitting ability. It drops rapidly and is difficult to use for a long time.
Therefore, a light-emitting device using a red organic phosphor made of a rare earth element ion complex having a high-luminance and low light degradation β-diketone, β-diketonate, Bronsted acid or aromatic carboxylic acid as a ligand. It has been proposed (see Patent Document 3 and Patent Document 4).

Japanese Patent Laid-Open No. 10-12925 JP 2000-509912 A JP 2005-8872 A WO2005 / 75598 pamphlet

  However, the luminance of the green phosphor and the blue phosphor is lower than that of the red organic phosphor as described above. For this reason, when it is set as a light-emitting device, the light quantity of a green area | region and a blue area | region becomes small compared with the light quantity of a red area | region, and there exist problems, such as color-rendering inferiority and the color shift of a luminescent color.

  An object of the present invention is to solve the above-described problems of the prior art, and to provide a light-emitting device that has high light emission efficiency and color rendering properties and has little color shift of the light emission color. That is, an object of the present invention is to provide a light emitting device that has high luminance, is closer to natural light, and has little deviation in emission color due to increase or decrease in the amount of emitted light, and an illumination device and an image display device using the light emitting device as a light source. It is what.

  The inventor of the present invention has intensively studied to solve the above problems, and as a result, by constructing a light-emitting device using a predetermined organic phosphor, it has a high luminance, is closer to natural light, and emits light with an increase or decrease in the amount of emitted light. The present invention has been completed by finding that a light emitting device with little color shift can be realized.

  That is, the gist of the present invention is a light emission comprising a light source that emits light having a peak wavelength in the range of 350 nm to 420 nm, and a phosphor that absorbs at least part of the light from the light source and emits light having a different wavelength. A light-emitting device comprising at least one organic phosphor as the phosphor, the light-emitting device having a luminous efficiency of 20 lm / W or higher, and an average color rendering index Ra of 80 or higher (Claim 1).

  At this time, as the organic phosphor, it is preferable to use a green organic phosphor that emits light having a peak wavelength in the range of 510 nm to 560 nm and the phosphor has an emission efficiency of 30% or more.

  Further, as the organic phosphor, it is preferable to use a red organic phosphor composed of a rare earth element ion complex having β-diketonate, β-diketone, aromatic carboxylic acid, or Bronsted acid as a ligand (claimed). Item 3).

  Further, as the red organic phosphor, it is preferable to use a red organic phosphor having a luminous efficiency of 20% or more.

  The light emitting device preferably emits white light.

Another subject matter of the present invention lies in an illumination device comprising the above light emitting device (Claim 6).
Still another subject matter of the present invention lies in an image display device comprising the above-described light emitting device (claim 7).

  According to the present invention, it is possible to provide a light emitting device that has high luminance, is closer to natural light, and has little deviation in emission color due to increase or decrease in the amount of emitted light, and an illumination device and an image display device that use the light emitting device as a light source. it can.

  The light emitting device of the present invention includes a light source that emits light having a peak wavelength in a range of 350 nm to 420 nm, and a phosphor that emits light having a different wavelength by absorbing at least part of the light from the light source. The light-emitting device of the present invention includes one or more organic phosphors as the phosphor, the light-emitting device has a light emission efficiency of 20 lm / W or higher, and an average color rendering evaluation index Ra of 80 or higher.

  Here, the efficiency of the light emitting device is defined in JISZ8113 “Illumination Terminology”, and is a value obtained by dividing the total luminous flux emitted from the light source by the power consumption of the light source, and the unit is “lm / W”. It is. In the present invention, the specific measurement method conforms to JISZ8724 “Color measurement method—Light source color”.

  In the present invention, the average color rendering index Ra was measured according to JIS Z8726 “Method for evaluating color rendering properties of light source”. The color rendering index is classified into a normal type and a high color rendering type according to JISZ9112, “Division by light source color and color rendering properties of fluorescent lamps”.

  Furthermore, in the present invention, the luminous efficiency (%) of the phosphor is measured by irradiating the phosphor with light having a peak wavelength of 400 nm (exposure time: 400 msec) and measuring the total reflected light amount (T1) and the light emission amount (S2) ( (Average value of 3 times) and the value obtained by (S2 × 100) / T1. Here, as the total reflected light amount, a value obtained by dividing the actually measured total reflected light amount by the reflectance of the standard white plate is used.

[Embodiment]
Hereinafter, embodiments of the present invention will be described in detail. However, the description of the constituent requirements described below is an example (representative example) of the embodiment of the present invention, and the present invention is not limited to these contents as long as the gist thereof is not exceeded. In the present specification, a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.

  FIG. 1 is a schematic diagram showing an outline of the light emitting device of the present embodiment. As shown in FIG. 1, the light emitting device 1 includes a light source 2 and a phosphor 3. In addition, the light emitting device 1 of the present embodiment includes an external cap 4 in order to protect the internal light source 2 and the phosphor 3.

[1. light source]
The light source is not particularly limited as long as it emits light having a peak wavelength in the range of 350 nm to 420 nm, and any light source can be used. Specific examples thereof include a light emitting diode (LED) and a laser diode (LD). Of these, GaN LEDs and LDs using GaN compound semiconductors are preferred. This is because GaN-based LEDs and LDs have significantly higher light emission output and external quantum efficiency than SiC-based LEDs that emit light in this region. This is because

For example, for a current load of 20 mA, GaN LEDs and LDs usually have a light emission intensity that is 100 times or more that of SiC. The GaN-based LED or LD preferably has an Al _x Ga _Y N light emitting layer, a GaN light emitting layer, or an In _x Ga _Y N light emitting layer. Among the GaN-based LEDs, those having an In _X Ga _Y N light emitting layer are particularly preferable because the light emission intensity is very strong. Further, in the GaN-based LD, a multiple quantum well structure of an In _x Ga _y N layer and a GaN layer is particularly preferable because the emission intensity is very strong. In the above, the value of X + Y is usually a value in the range of 0.8 to 1.2. In the GaN-based LED, those in which the light emitting layer is doped with Zn or Si or those without a dopant are preferable for adjusting the light emission characteristics.

The GaN-based LED has these light emitting layer, p layer, n layer, electrode, and substrate as basic components. Among them, a light emitting layer having a heterostructure sandwiched between n-type and p-type Al _x Ga _y N layers, GaN layers, or In _x Ga _y N layers is preferable because of high luminous efficiency. Further, a heterostructure having a quantum well structure has higher luminous efficiency and is more preferable.

  In the present embodiment, it is assumed that a GaN-based LED is used as the light source 2.

[2. Phosphor]
The light emitting device of the present invention includes a phosphor. This phosphor absorbs at least a part of the light from the light source and emits light (fluorescence) having a wavelength different from that of the light from the light source.
As the fluorescent material, a material that emits light of any color may be used. Usually, a red fluorescent material (that is, a fluorescent material that emits red light) or a green fluorescent material (that is, a fluorescent material that emits green light). ) And a blue phosphor (that is, a phosphor emitting blue light). This is to cause the light emitting device to emit white light.

Moreover, the light-emitting device of this invention contains 1 or more types of organic fluorescent substance as fluorescent substance. In particular, an organic phosphor is preferably used as the red phosphor or the green phosphor, and an organic phosphor is preferably used as the red phosphor and the green phosphor.
On the other hand, as the blue phosphor, either an inorganic phosphor or an organic phosphor may be used, and can be appropriately selected depending on the type of the red phosphor, the green phosphor and the like.
Even when an organic phosphor is used as the red phosphor or the green phosphor, the red inorganic phosphor or the green inorganic phosphor may be used in combination with the organic phosphor.

[2-1. Green phosphor]
When a green phosphor is used, a phosphor that emits light by absorbing at least part of light from a light source that emits light having a peak wavelength in the range of 350 nm to 420 nm is used. At this time, it is preferable to use a green organic phosphor as the green phosphor.

  The green organic phosphor is usually 510 nm or more, preferably 520 nm or more, more preferably 525 nm or more, particularly preferably 530 nm or more, and usually 560 nm or less, preferably 550 nm or less, more preferably 545 nm or less, particularly preferably 540 nm or less. It is desirable to emit light having a peak wavelength in the range. Since the emission spectrum of such a green organic phosphor has a large overlap with the visibility curve, a light emitting device with higher luminance can be manufactured.

  Moreover, although there is no restriction | limiting in the luminous efficiency of green organic fluorescent substance, it is desirable to use a thing with high luminous efficiency. Specifically, a phosphor having a luminous efficiency of usually 30% or more, preferably 35% or more, more preferably 40% or more, and particularly preferably 45% or more is used. By using a green phosphor with high luminous efficiency in this way, the amount of phosphor used can be reduced, and a light emitting device with high luminance can be manufactured even when the power of the light source is small.

Examples of the green organic phosphor that can be used in the present invention include pyridine-phthalimide condensed derivatives. Specific examples include quinoline represented by the following formula described in Liedigs Ann.Chem., Vol.315, p303 (1901) and Chem.Ber., Vol.100, p.2261-2273 (1967). Examples thereof include a condensation compound of a derivative and phthalimide, and a condensation compound of a pyridine derivative and naphthalimide described in JP-A No. 11-152467.

〔式中、Ｒ₁およびＲ₂は、それぞれ独立に、水素、置換基を有していてもよいアルキル基、または、置換基を有していてもよいアリール基を表わす。Ｘ₁〜Ｘ₄及びＹ₁〜Ｙ₄は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有していてもよい直鎖、分岐または環状のアルキル基、置換基を有していてもよい直鎖、分岐または環状のアルコキシ基、置換基を有していてもよい直鎖、分岐または環状のアルキルチオ基、置換基を有していてもよい直鎖、分岐または環状のアルケニル基、置換基を有していてもよい直鎖、分岐または環状のアルケニルオキシ基、置換基を有していてもよい直鎖、分岐または環状のアルケニルチオ基、置換基を有していてもよいアラルキル基、置換基を有していてもよいアラルキルオキシ基、置換基を有していてもよいアラルキルチオ基、置換基を有していてもよいアリール基、置換基を有していてもよいアリールオキシ基、置換基を有していてもよいアリールチオ基、置換基を有していてもよいアミノ基、シアノ基、水酸基、ニトロ基、−ＣＯＯＲ₃基（基中、Ｒ₃は、水素原子、置換基を有していてもよい直鎖、分岐または環状のアルキル基、置換基を有していてもよい直鎖、分岐または環状のアルケニル基、置換基を有していてもよいアラルキル基、あるいは、置換基を有していてもよいアリール基を表わす）、−ＣＯＲ₄基（基中、Ｒ₄は、水素原子、置換基を有していてもよい直鎖、分岐または環状のアルキル基、置換基を有していてもよい直鎖、分岐または環状のアルケニル基、置換基を有していてもよいアラルキル基、置換基を有していてもよいアリール基、あるいは、アミノ基を表わす）、あるいは、−ＯＣＯＲ₅基（基中、Ｒ₅は置換基を有していてもよい直鎖、分岐または環状のアルキル基、置換基を有していてもよい直鎖、分岐または環状のアルケニル基、置換基を有していてもよいアラルキル基、あるいは置換基を有していてもよいアリール基を表わす）を表わす。さらに、Ｘ₁〜Ｘ₄およびＹ₁〜Ｙ₄から選ばれる隣接する基は互いに結合して、置換している炭素原子と共に、置換基を有していてもよい炭素環式脂肪族環、置換基を有していてもよい炭素環式芳香族環、置換基を有していてもよい複素環式脂肪族環、または、置換基を有していてもよい複素環式芳香族環を形成していてもよい。〕 Moreover, as a green organic fluorescent substance, the pyridine-phthalimide condensation derivative compound represented, for example by following General formula (1) can also be used suitably.

[Wherein, R ₁ and R ₂ each independently represent hydrogen, an alkyl group which may have a substituent, or an aryl group which may have a substituent. X _{1 to} X ₄ and Y _{1 to} Y ₄ may each independently have a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or a substituent. Good linear, branched or cyclic alkoxy group, linear, branched or cyclic alkylthio group which may have a substituent, linear, branched or cyclic alkenyl group which may have a substituent, substitution A linear, branched or cyclic alkenyloxy group which may have a group, a linear, branched or cyclic alkenylthio group which may have a substituent, and an aralkyl group which may have a substituent An aralkyloxy group which may have a substituent, an aralkylthio group which may have a substituent, an aryl group which may have a substituent, an aryloxy which may have a substituent Group, an ant that may have a substituent Thio group, amino group optionally having substituent, cyano group, hydroxyl group, nitro group, -COOR ₃ group (in the group, R ₃ is a hydrogen atom, a linear chain optionally having substituent, A branched or cyclic alkyl group, a linear, branched or cyclic alkenyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl which may have a substituent Represents a group), -COR ₄ group (in the group, R ₄ is a hydrogen atom, an optionally substituted linear, branched or cyclic alkyl group, an optionally substituted linear) , A branched or cyclic alkenyl group, an aralkyl group which may have a substituent, an aryl group which may have a substituent, or an amino group, or an —OCOR ₅ group (in the group, R ₅ represents a linear which may have a substituent, branched or cyclic An alkyl group, a linear, branched or cyclic alkenyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent). Represent. Further, adjacent groups selected from X _{1 to} X ₄ and Y _{1 to} Y ₄ are bonded to each other, and together with the substituted carbon atom, an optionally substituted carbocyclic aliphatic ring, substituted A carbocyclic aromatic ring optionally having a group, a heterocyclic aliphatic ring optionally having a substituent, or a heterocyclic aromatic ring optionally having a substituent You may do it. ]

In the general formula (1), R ₁ and R ₂ each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. Among these, a hydrogen atom, an alkyl group which may have a substituent having 1 to 10 carbon atoms, and an aryl group having 6 to 12 carbon atoms are preferable. More preferably, it represents a hydrogen atom, an alkyl group which may have a grounding effect of 1 to 6 carbon atoms, or an aryl group of 6 to 10 carbon atoms.
Incidentally, R ₁ and R ₂ which may have a substituent alkyl group, specific examples of the aryl group which may have a substituent, X ₁ to X ₄ and Y ₁ to Y ₄ to be described later Specific examples of the alkyl group may include an alkyl group which may have a substituent and an aryl group which may have a substituent.

In the general formula (1), X _{1 to} X ₄ and Y _{1 to} Y ₄ are each independently a hydrogen atom, a halogen atom, or a linear, branched or cyclic alkyl group which may have a substituent. A linear, branched or cyclic alkoxy group which may have a substituent, a linear, branched or cyclic alkylthio group which may have a substituent, and a linear chain which may have a substituent A branched or cyclic alkenyl group, a linear, branched or cyclic alkenyloxy group which may have a substituent, a linear, branched or cyclic alkenylthio group which may have a substituent, a substituent An aralkyl group which may have a substituent, an aralkyloxy group which may have a substituent, an aralkylthio group which may have a substituent, an aryl group which may have a substituent, a substituent An aryloxy group optionally having An arylthio group which may have a substituent, an amino group which may have a substituent, a cyano group, a hydroxyl group, a nitro group, a —COOR ₃ group (in the group, R ₃ represents a hydrogen atom, a substituent; Linear, branched or cyclic alkyl group which may have, linear, branched or cyclic alkenyl group which may have substituent, aralkyl group which may have substituent, or substituent -COR ₄ group (in the group, R ₄ represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a substituent; A linear, branched or cyclic alkenyl group which may have, an aralkyl group which may have a substituent, an aryl group which may have a substituent, or an amino group), or -OCOR ₅ groups (group, R ₅ may have a substituent A chain, branched or cyclic alkyl group, a linear, branched or cyclic alkenyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent Represents a good aryl group).

  The aryl group represents a carbocyclic aromatic group such as a phenyl group or a naphthyl group, for example, a heterocyclic aromatic group such as a furyl group, a thienyl group or a pyridyl group.

Furthermore, in the general formula (1), among X _{1 to} X ₄ and Y _{1 to} Y ₄ , a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a linear, branched or cyclic group Examples of the substituent that the alkylthio group, the linear, branched or cyclic alkenyl group, the linear, branched or cyclic alkenyloxy group, and the linear, branched or cyclic alkenylthio group may have include: A halogen atom, an aryl group having 4 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxyalkoxy group having 2 to 20 carbon atoms, an alkenyloxy group having 2 to 20 carbon atoms, and an aralkyloxy group having 4 to 20 carbon atoms , An aralkyloxyalkoxy group having 5 to 20 carbon atoms, an aryloxy group having 3 to 20 carbon atoms, an aryloxyalkoxy group having 4 to 20 carbon atoms, an aryl group having 5 to 20 carbon atoms Lucenyl group, C6-C20 aralkylalkenyl group, C1-C20 alkylthio group, C2-C20 alkoxyalkylthio group, C2-C20 alkylthioalkylthio group, C2-C20 alkenylthio Group, aralkylthio group having 4 to 20 carbon atoms, aralkyloxyalkylthio group having 5 to 20 carbon atoms, aralkylthioalkylthio group having 5 to 20 carbon atoms, arylthio group having 3 to 20 carbon atoms, aryl having 4 to 20 carbon atoms Examples thereof include an oxyalkylthio group, an arylthioalkylthio group having 4 to 20 carbon atoms, a cyclic alkyl group having 4 to 20 carbon atoms, a hydroxyl group, a cyano group, and a halogen atom. The number of substituents is arbitrary as long as the effects of the present invention are not significantly impaired, and the substitution may be mono-substitution or poly-substitution. Furthermore, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 3 to 10 carbon atoms, and 4 to 10 carbon atoms. May be substituted with an aralkyl group.

In the general formula (1), among X _{1 to} X ₄ and Y _{1 to} Y ₄ , an aralkyl group, an aralkyloxy group, an aralkylthio group, an aryl group, an aryloxy group, and an aryl group in the arylthio group are present. Examples of the substituent that may be used include an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aralkyl group having 4 to 20 carbon atoms, an aryl group having 3 to 20 carbon atoms, and a carbon number 1-20 alkoxy group, C2-C20 alkoxyalkyl group, C2-C20 alkoxyalkyloxy group, C2-C20 alkenyloxy group, C3-C20 alkenyloxyalkyl group, carbon C3-C20 alkenyloxyalkyloxy group, C4-C20 aralkyloxy group, C5-C20 aralkyloxyalkyl group, C5-C20 An aralkyloxyalkyloxy group, an aryloxy group having 3 to 20 carbon atoms, an aryloxyalkyl group having 4 to 20 carbon atoms, an aryloxyalkyloxy group having 4 to 20 carbon atoms, an alkylcarbonyl group having 2 to 20 carbon atoms, C3-C20 alkenylcarbonyl group, C5-C20 aralkylcarbonyl group, C4-C20 arylcarbonyl group, C2-C20 alkoxycarbonyl group, C3-C20 alkenyloxycarbonyl group , An aralkyloxycarbonyl group having 5 to 20 carbon atoms, an aryloxycarbonyl group having 4 to 20 carbon atoms, an alkylcarbonyloxy group having 2 to 20 carbon atoms, an alkenylcarbonyloxy group having 3 to 20 carbon atoms, and 5 carbon atoms -20 aralkylcarbonyloxy group, arylcarbonyloxy group having 4-20 carbon atoms Group, C1-C20 alkylthio group, C4-C20 aralkylthio group, C3-C20 arylthio group, nitro group, cyano group, formyl group, halogen atom, halogenated alkyl group, hydroxyl group, amino group Group, an N-monosubstituted amino group having 1 to 20 carbon atoms, an N, N-disubstituted amino group having 2 to 40 carbon atoms, and the like. The number of substituents is arbitrary as long as the effects of the present invention are not significantly impaired, and the substitution may be mono-substitution or poly-substitution. Furthermore, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, and an aryl group having 7 to 10 carbon atoms. It may be substituted with an aralkyl group.

Further, in the general formula (1), of X ₁ to X ₄ and Y ₁ to Y _4, examples of the substituent which may be possessed by an amino group, an alkyl group having 1 to 20 carbon atoms, carbon atoms Examples thereof include an aralkyl group having 4 to 20 or an aryl group having 3 to 20 carbon atoms. Moreover, when substituted with a substituent, it may be monosubstituted or disubstituted.

When X _{1 to} X ₄ and Y _{1 to} Y ₄ are a —COOR ₃ group, as described above, R ₃ is a hydrogen atom, a linear, branched or cyclic alkyl which may have a substituent. And a linear, branched or cyclic alkenyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent. Among them, R ₃ is preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, or a total carbon number which may have a substituent. 2 to 24 linear, branched or cyclic alkenyl groups, an optionally substituted aralkyl group having 7 to 24 carbon atoms, or an optionally substituted total carbon number 6 to 24 Of the aryl group. Furthermore, more preferably, a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and a total carbon number of 7 to 24 which may have a substituent. Or an aryl group having 6 to 24 carbon atoms which may have a substituent.
In R ₃ , the alkyl group, alkenyl group, aralkyl group, and aryl group may have a substituent. Examples of the substituent include the same groups as those exemplified as the substituent of X ₁ to X ₄ and Y ₁ to Y _4. Further, the substitution may be mono-substitution or poly-substitution.

Further, when X _{1 to} X ₄ and Y _{1 to} Y ₄ are a —COR ₄ group, as described above, R ₄ is a hydrogen atom, a linear, branched or cyclic alkyl which may have a substituent. A linear, branched or cyclic alkenyl group which may have a substituent, an aralkyl group which may have a substituent, an aryl group which may have a substituent, or an amino group. Represent. Among them, R ₄ is preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, or a total carbon number which may have a substituent. A linear, branched or cyclic alkenyl group having 2 to 24 carbon atoms, an aralkyl group having 7 to 24 carbon atoms which may have a substituent, and an aryl having 6 to 24 carbon atoms which may have a substituent Group or amino group. Furthermore, more preferably, a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and a total carbon number of 7 to 24 which may have a substituent. An aralkyl group, an aryl group having 6 to 24 carbon atoms which may have a substituent, or an amino group.
In R ₄ , the alkyl group, alkenyl group, aralkyl group, and aryl group may have a substituent. Examples of the substituent include the same groups as those exemplified as the substituent of X ₁ to X ₄ and Y ₁ to Y _4. Further, the substitution may be mono-substitution or poly-substitution.

When X _{1 to} X ₄ and Y _{1 to} Y ₄ are —OCOR ₅ groups, as described above, R ₅ is a linear, branched or cyclic alkyl group which may have a substituent, A linear, branched or cyclic alkenyl group which may have a group, an aralkyl group which may have a substituent, or an aryl group which may have a substituent. Among them, R ₅ is preferably a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, or a total carbon number of 2 to 24 which may have a substituent. A linear, branched or cyclic alkenyl group, an aralkyl group having 7 to 24 carbon atoms which may have a substituent, or an aryl group having 6 to 24 carbon atoms which may have a substituent It is. Furthermore, more preferably, the C1-C24 linear, branched or cyclic alkyl group which may have a substituent, and the C7-24 aralkyl group which may have a substituent. Or an aryl group having 6 to 24 carbon atoms which may have a substituent.
In R ₅ , the alkyl group, alkenyl group, aralkyl group, and aryl group may have a substituent. Examples of the substituent include the same groups as those exemplified as the substituent of X ₁ to X ₄ and Y ₁ to Y _4. Further, the substitution may be mono-substitution or poly-substitution.

Among X ₁ to X ₄ and Y ₁ to Y ₄ as described above is also preferably a hydrogen atom, a halogen atom, a straight-chain of atoms which total or carbon with 1 to 24 having a substituent, alkyl branched or cyclic A linear, branched or cyclic alkoxy group having 1 to 24 carbon atoms which may have a group, a substituent, a linear, branched or cyclic group having 1 to 24 carbon atoms which may have a substituent An alkylthio group, a linear or branched alkenyl group having 2 to 24 carbon atoms which may have a substituent, a linear or branched chain having 2 to 24 carbon atoms which may have a substituent Or a cyclic alkenyloxy group, a straight chain, branched or cyclic alkenylthio group optionally having a substituent and a substituent having a total carbon number of 7 to 24 Aralkyl group, Aralkylo having 7 to 24 carbon atoms which may have a substituent A xy group, an aralkylthio group having 7 to 24 carbon atoms which may have a substituent, an aryl group having 6 to 24 carbon atoms which may have a substituent, and a substituent. Good aryloxy group having 6 to 24 carbon atoms, arylthio group having 6 to 24 carbon atoms which may have a substituent, unsubstituted amino group, substituted amino group having 1 to 24 carbon atoms, and cyano group , Hydroxyl group, nitro group, —COOR ₃ , —COR ₄ , or —OCOR ₅ (wherein R _{3 to} R ₅ are the same as those described above).

Furthermore, among the above-mentioned X _{1 to} X ₄ and Y _{1 to} Y ₄ , more preferably a hydrogen atom, a halogen atom, a straight chain having 1 to 12 carbon atoms which may have a substituent, branched or A cyclic alkyl group, a straight chain having 1 to 12 carbon atoms which may have a substituent, a branched or cyclic alkoxy group, a straight chain having 2 to 12 carbon atoms which may have a substituent, It has a branched or cyclic alkenyl group, an aralkyl group having 7 to 16 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, and a substituent. An aryloxy group having 6 to 24 carbon atoms, an arylthio group having 6 to 12 carbon atoms which may have a substituent, an unsubstituted amino group, and a substituted amino group having 1 to 12 carbon atoms , A cyano group, a hydroxyl group, a nitro group, —COOR ₃ , —COR ₄ , or —O COR ₅ (wherein R _{3 to} R ₅ are the same as those described above).

Also, adjacent groups selected from X ₁ to X ₄ and Y ₁ to Y ₄ may form a ring together with the carbon atoms to which they are substituted. For example, a carbocyclic aliphatic ring that may have a substituent, a carbocyclic aromatic ring that may have a substituent, a heterocyclic aliphatic ring that may have a substituent, Or the heterocyclic aromatic ring which may have a substituent may be formed. Among them, a carbocyclic aliphatic ring which may have a substituent having a total carbon number of 4 to 20, a carbocyclic aromatic ring having a total carbon number of 4 to 20, and a substituent having a total carbon number of 4 to 20 are preferable. A heterocyclic aliphatic ring which may have a heterocyclic ring or a heterocyclic aromatic ring having a total carbon number of 4 to 20 may be formed.

Specific examples of X _{1 to} X ₄ and Y _{1 to} Y ₄ include a hydrogen atom; for example, a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; for example, a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. , N-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl- 2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2, 2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group, n-un Decyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group, n-octadecyl group, 1-nonyldecyl group, 1-decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2 -Cyclohexylethyl group, bornel group, isobornel group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl Group, cyclobutyl group, cyclopentyl group, 1-methylcyclopenty Group, cyclohexyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4 -Dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3 -Tert-butylcyclohexyl group, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, cyclododecyl group, cyclotetradecyl group, methoxymethyl group, ethoxymethyl group, n- Toximethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, n-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-n- Propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2- (2′-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2′-ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group, 2-n-dodecyloxyethyl group, 2- n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropyl group, 3-methoxypropyl group, 3-ethoxy group Pill group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3- (n-butoxy) propyl group, 3- (n-pentyloxy) propyl group, 3- (n-hexyloxy) propyl group, 3- (2'-ethylbutoxy) propyl group, 3- (n-octyloxy) propyl group, 3- (2'-ethylhexyloxy) propyl group, 3- (n-decyloxy) propyl group, 3- (n- Dodecyloxy) propyl group, 3- (n-tetradecyloxy) propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-isopropoxybutyl Group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4-n-octyloxybutyl group, 4-n-decyloxybutyl group Group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl group, 6-ethoxyhexyl group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl Group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-methoxyoctyl group, 10-methoxydecyl group 10-n-butoxydecyl group, 12-ethoxydodecyl group, 12-isopropoxide decyl group, tetrahydrofurfuryl group, 2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group 2- (2′-n-butoxyethoxy) ethyl group, 3- (2′-ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4′-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2′-hexenyloxy) propyl group, 3- (2′-heptenyloxy) propyl group, 3 -(1'-cyclohexenyloxy) propyl group, 4-allyloxybutyl group, benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4'-methylbenzyloxy) ethyl group 2- (2′-methylbenzyloxy) ethyl group, 2- (4′-fluorobenzyloxy) ethyl group, 2- (4′-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- ( 4′-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) ethyl group, 2- (4′-methylben) Zyloxymethoxy) ethyl group, phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl Group, 4-chlorophenyloxymethyl group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl group, 2 -(4'-methoxyphenyloxy) ethyl group, 2- (4'-chlorophenyloxy) ethyl group, 2- (4'-bromophenyloxy) ethyl group, 2- (1'-naphthyloxy) ethyl group, 2 -(2'-naphthyloxy) ethyl group, 3-phenyloxypropyl group, 3- (2'-naphthyloxy) ) Propyl group, 4-phenyloxybutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group 8-phenyloxyoctyl group, 10-phenyloxydecyl group, 10- (3′-chlorophenyloxy) decyl group, 2- (2′-phenyloxyethoxy) ethyl group, 3- (2′-phenyloxyethoxy) Propyl group, 4- (2'-phenyloxyethoxy) butyl group, n-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl Group, 2-n-hexylthioethyl group, 2-n-octylthioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, -Ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group, 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthio Hexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2′-methoxyethylthio) ethyl group, 4- (3′-ethoxypropylthio) butyl group 2- (2′-ethylthioethylthio) ethyl group, 2-allylthioethyl group, 2-benzylthioethyl group, 3- (4′-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2 -(2'-benzyloxyethylthio) ethyl group, 3- (3'-benzylthiopropylthio) propyl group, 2-phenylthioethyl group, 2- (4'-methoxyphenylthio) ) Ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) propyl group, fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8- Fluorooctyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro-n-propyl group, 1,1,3-trihydro-perfluoro-n-propyl group, 1,1-dihydro-perfluoro-n-butyl group, 1,1-dihydro-perfluoro-n-pentyl group, 1,1-dihydro-perfluoro-n-hexyl group, 6-fluorohexyl group, 4- Fluorocyclohexyl group, 1,1-dihydro-perfluoro-n-octyl group, 1,1-dihydro-perfluoro-n-decyl group, 1,1-dihydro Perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro-n-tetradecyl group, 1,1-dihydro-perfluoro-n-hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2- Chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chlorooctyl group, 2,2,2-trichloroethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3 -Hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8-hydroxyoctyl group, 10-hydroxydecyl group, 12-hydroxydodecyl group, 2-hydroxy A linear, branched or cyclic alkyl group such as a cyclohexyl group;

For example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 2-ethylbutoxy group, 3,3-dimethylbutoxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy Group, n-dodecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, n-octadecyloxy group, n-eicosyloxy group, n-docosyloxy group, n-tetracosyloxy group, fluoromethoxy Group, trifluoromethoxy group, 1,1-dihydroperfluoroe Xyl group, perfluoroethoxy group, 1,1-dihydroperfluoro-n-propoxy group, 1,1,3-trihydroperfluoro-n-propoxy group, 1,1-dihydroperfluoro-n-butoxy group, 1,1-dihydroperfluoro-n-pentyloxy group, 1,1-dihydroperfluoro-n-hexyloxy group, 4-chlorocyclohexyloxy group, 1,1-dihydroperfluoro-n-octyloxy group, 1 1,1-dihydroperfluoro-n-decyloxy group, 1,1-dihydroperfluoro-n-dodecyloxy group, 1,1-dihydroperfluoro-n-hexadecyloxy group, ethoxymethoxy group, 1-methoxyethoxy group 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propoxyethoxy group, 2-isopropoxy group Ciethoxy group, 2-n-butoxyethoxy group, 2-n-hexyloxyethoxy group, 2-n-octyloxyethoxy group, 2- (2′-ethylhexyloxy) ethoxy group, 2-n-decyloxyethoxy group, 2-methoxypropoxy group, 3-methoxypropoxy group, 3-ethoxypropoxy group, 3-isopropoxypropoxy group, 3-n-butoxypropoxy group, 3-n-hexyloxypropoxy group, 3-n-octyloxypropoxy group 2-methoxybutoxy group, 3-methoxybutoxy group, 4-methoxybutoxy group, 4-ethoxybutoxy group, 4-isopropoxybutoxy group, 4-n-butoxybutoxy group, 4-n-hexyloxybutoxy group, 4 -N-decyloxybutoxy group, 4-n-dodecyloxybutoxy group, 5-ethoxy Nyloxy group, 6-methoxyhexyloxy group, 6-ethoxyhexyloxy group, 6-isopropoxyhexyloxy group, 4-methoxycyclohexyloxy group, 7-methoxyheptyloxy group, 8-ethoxyoctyloxy group, 10-methoxydecyl Oxy group, 12-ethoxydodecyloxy group, 2- (2′-methoxyethyloxy) ethoxy group, 3- (2′-ethoxyethyloxy) propoxy group, 2-benzyloxyethoxy group, 2- (4-methylbenzyl) Oxy) ethoxy group, 2- (4-methoxybenzyloxy) ethoxy group, 3- (4-ethylbenzyloxy) propoxy group, 4- (3-fluorobenzyloxy) butoxy group, 4- (4-chlorobenzyloxy) Butoxy group, 6- (3-methylbenzyloxy) hexyloxy Group, phenyloxymethoxy group, 2-phenyloxyethoxy group, 2- (1'-naphthyloxy) ethoxy group, 2- (2'-naphthyloxy) ethoxy group, 2- (4'-methylphenyloxy) ethoxy group 2- (4′-methoxyphenyloxy) ethoxy group, 2- (3′-ethoxyphenyloxy) ethoxy group, 2- (4′-chlorophenyloxy) ethoxy group, 3-phenyloxypropoxy group, 3- (4 '-Ethylphenyloxy) propoxy group, 3- (4'-chlorophenyloxy) propoxy group, 3- (2'-naphthyloxy) propoxy group, 4-phenyloxybutoxy group, 6-phenyloxyhexyloxy group, 8- Linear, branched or cyclic alkyl such as phenyloxyoctyloxy group, 10-phenyloxydecyloxy group A alkoxy group;

For example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, n-pentylthio group, neopentylthio group, isopentylthio group, cyclopentylthio group, n-hexylthio group, 2-ethylbutylthio group, 3,3-dimethylbutylthio group, cyclohexylthio group, n-heptylthio group, n-octylthio group, 2-ethylhexylthio group, n-nonylthio group, n-decylthio group N-dodecylthio group, n-tetradecylthio group, n-hexadecylthio group, n-octadecylthio group, n-eicosylthio group, n-docosylthio group, n-tetracosylthio group, fluoromethylthio group, trifluoromethylthio group, 1,1-dihydroperfluoroethylthio group, Fluoroethylthio group, 1,1-dihydroperfluoro-n-propylthio group, 1,1,3-trihydroperfluoro-n-propylthio group, 1,1-dihydroperfluoro-n-butylthio group, 1,1 -Dihydroperfluoro-n-pentylthio group, 1,1-dihydroperfluoro-n-hexylthio group, 4-chlorocyclohexylthio group, 1,1-dihydroperfluoro-n-octylthio group, 1,1-dihydroperfluoro -N-decylthio group, 1,1-dihydroperfluoro-n-dodecylthio group, 1,1-dihydroperfluoro-n-hexadecylthio group, ethoxymethylthio group, 1-methoxyethylthio group, 2-methoxyethylthio group, 2-ethoxyethylthio group, 2-n-propoxyethylthio group, 2-isopropoxyethyl Thio group, 2-n-butoxyethylthio group, 2-n-hexyloxyethylthio group, 2-n-octyloxyethylthio group, 2- (2′-ethylhexyloxy) ethylthio group, 2-n-decyloxy Ethylthio group, 2-methoxypropylthio group, 3-methoxypropylthio group, 3-ethoxypropylthio group, 3-isopropoxypropylthio group, 3-n-butoxypropylthio group, 3-n-hexyloxypropylthio group Group, 3-n-octyloxypropylthio group, 2-methoxybutylthio group, 3-methoxybutylthio group, 4-methoxybutylthio group, 4-ethoxybutylthio group, 4-isopropoxybutylthio group, 4- n-butoxybutylthio group, 4-n-hexyloxybutylthio group, 4-n-decyloxybutylthio group, 4-n-dode Ruoxybutylthio group, 5-ethoxypentylthio group, 6-methoxyhexylthio group, 6-ethoxyhexylthio group, 6-isopropoxyhexylthio group, 4-methoxycyclohexylthio group, 7-methoxyheptylthio group, 8 -Ethoxyoctylthio group, 10-methoxydecylthio group, 12-ethoxydodecylthio group, 2-[(2'-methoxyethyl) oxy] ethylthio group, 3-[(2'-ethoxyethyl) oxy] propylthio group, 2-benzyloxyethylthio group, 2- (4-methylbenzyloxy) ethylthio group, 2- (4-methoxybenzyloxy) ethylthio group, 3- (4-ethylbenzyloxy) propylthio group, 4- (3-fluoro Benzyloxy) butylthio group, 4- (4-chlorobenzyloxy) butylthio group, 6 (3-methylbenzyloxy) hexylthio group, phenyloxymethylthio group, 2-phenyloxyethylthio group, 2- (1′-naphthyloxy) ethylthio group, 2- (2′-naphthyloxy) ethylthio group, 2- ( 4′-methylphenyloxy) ethylthio group, 2- (4′-methoxyphenyloxy) ethylthio group, 2- (3′-ethoxyphenyloxy) ethylthio group, 2- (4′-chlorophenyloxy) ethylthio group, 3- Phenyloxypropylthio group, 3- (4′-ethylphenyloxy) propylthio group, 3- (4′-chlorophenyloxy) propylthio group, 3- (2′-naphthyloxy) propylthio group, 4-phenyloxybutylthio group 6-phenyloxyhexylthio group, 8-phenyloxyoctylthio group, 10 A linear, branched or cyclic alkylthio group such as a phenyloxydecylthio group;

For example, vinyl group, allyl group, 2-butenyl group, 3-butenyl group, 1-methyl-4-pentenyl group, 2-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-hexenyl group 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 2-heptenyl group, 1-vinylhexyl group, 3-nonenyl group, 6-nonenyl group, 9-decenyl group, 10-undecenyl group, 13-tetradecenyl group Group, 15-hexadecenyl group, 17-octadecenyl group, 23-n-tetracocenyl group, 1-cyclopentenyl group, 1-cyclohexenyl group, ethoxyvinyl group, n-butoxyvinyl group, benzylvinyl group, styryl group, styrylmethyl Group, 2-styrylethyl group, 2,2-diphenylvinyl group, 2- (4′-methylphenyl) vinyl group, 2- ( '- methylphenyl) vinyl group, 2- (4'-methoxyphenyl) vinyl group, 2- (4'-chlorophenyl) vinyl group, a straight chain, a branched alkenyl group or cyclic, such as phenyloxy vinyl group;

For example, vinyloxy group, allyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl-4-pentenyloxy group, 2-pentenyloxy group, 4-pentenyloxy group, 1-methyl-2-butenyloxy group, 2 -Hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 2-heptenyloxy group, 1-vinylhexyloxy group, 3-nonenyloxy group, 6-nonenyloxy group, 9-decenyloxy group, 10-undecenyloxy group, 13-tetradecenyloxy group, 15-hexadecenyloxy group, 17-octadecenyloxy group, 23-tetracocenyloxy group, 1-cyclopentenyloxy group, 1-cyclohexenyloxy group, ethoxyvinyloxy group, n-butoxyvinyl Alkoxy group, a benzyl vinyl group, styryloxy group, a linear, branched or cyclic alkenyloxy group such as phenyloxy vinyl group;

For example, vinylthio group, allylthio group, 2-butenylthio group, 3-butenylthio group, 4-pentenylthio group, 5-hexenylthio group, 9-decenylthio group, 13-tetradecenylthio group, 15-hexadecenylthio group , A 17-octadecenylthio group, a 23-tetracocenylthio group, a 1-cyclohexenylthio group, an n-butoxyvinylthio group or the like, a linear, branched or cyclic alkenylthio group;

For example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4- Methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2- tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4- Phenethylbenzyl group, 4-phenylbenzyl group, 4- (4′-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n-tetradecyl Oxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl Group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group, 4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4- Hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2- Fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, etc. An aralkyl group optionally having a substituent;

For example, benzyloxy group, phenethyloxy group, β-methylphenethyloxy group, 4-methylphenethyloxy group, 4-methylbenzyloxy group, 3-methylbenzyloxy group, 2-methylbenzyloxy group, 4-ethylbenzyloxy group Group, 4-isopropylbenzyloxy group, 4-tert-butylbenzyloxy group, 4-cyclohexylbenzyloxy group, 4-n-octylbenzyloxy group, 4-allylbenzyloxy group, 4-benzylbenzyloxy group, 4- Phenylbenzyloxy group, 4- (4′-methylphenyl) benzyloxy group, 4-methoxybenzyloxy group, 2-methoxybenzyloxy group, 2-ethoxybenzyloxy group, 4-n-butoxybenzyloxy group, 4- n-heptyloxybenzyloxy group, 4-n- Siloxybenzyloxy group, 4-n-tetradecyloxybenzyloxy group, 4-n-heptadecyloxybenzyloxy group, 3,4-dimethoxybenzyloxy group, 4-methoxymethylbenzyloxy group, 4-isobutoxymethyl Benzyloxy group, 4-allyloxybenzyloxy group, 4-vinyloxymethylbenzyloxy group, 4-benzyloxybenzyloxy group, 4-phenethyloxybenzyloxy group, 4-phenyloxybenzyloxy group, 3-phenyloxybenzyl Oxy group, 4-hydroxybenzyloxy group, 4-fluorobenzyloxy group, 4-chlorobenzyloxy group, 3-chlorobenzyloxy group, 3,4-dichlorobenzyloxy group, 1-naphthylmethyloxy group, 2-naphthyl Substituents such as methyloxy group An aralkyloxy group optionally having:

For example, benzylthio group, phenethylthio group, β-methylphenethyloxy group, 4-methylphenethylthio group, 4-methylbenzylthio group, 3-methylbenzylthio group, 4-ethylbenzylthio group, 4-isopropylbenzylthio group 4-tert-butylbenzylthio group, 4-cyclohexylbenzylthio group, 4-n-octylbenzylthio group, 4-allylbenzylthio group, 4-benzylbenzylthio group, 4-phenylbenzylthio group, 4- ( 4′-methylphenyl) benzylthio group, 4-methoxybenzylthio group, 2-methoxybenzylthio group, 2-ethoxybenzylthio group, 4-n-butoxybenzylthio group, 4-n-heptyloxybenzylthio group, 4 -N-decyloxybenzylthio group, 4-n-tetradecyloxybenzylthio group 4-n-heptadecyloxybenzylthio group, 3,4-dimethoxybenzylthio group, 4-methoxymethylbenzylthio group, 4-allyloxybenzylthio group, 4-benzyloxybenzylthio group, 4-phenethyloxybenzyl Thio group, 4-phenyloxybenzylthio group, 3-phenyloxybenzylthio group, 4-hydroxybenzylthio group, 4-fluorobenzylthio group, 4-chlorobenzylthio group, 1-naphthylmethylthio group, 2-naphthylmethylthio group An aralkylthio group optionally having a substituent such as a group;

For example, phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 9-anthracenyl group, fluorenyl group, 4-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 3- Furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, 4-methylphenyl Group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl Group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butyl Phenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-nonylphenyl group 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-n-hexadecylphenyl group, 4-n-octadecylphenyl group, 4-cyclopentylphenyl group, 4 -Cyclohexylphenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 4- (4'-methylcyclyl) Rohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 2,3-dimethylphenyl group, 2,4-dimethyl Phenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 3,4,5 -Trimethylphenyl group, 2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6-diethylphenyl group, 2,6-diisopropylphenyl group, 2 , 6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5-di-te t-butylphenyl group, 2,4-dineopentylphenyl group, 2,5-di-tert-pentylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl- 2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-indanyl group, 1,2,3,4-tetrahydro-5 Naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3- n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2- Sobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n- Hexyloxyphenyl group, 2- (2′-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyl Oxyphenyl group, 4-n-hexadecyloxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-1-naphthyl group, 4-methoxy- 1-naphthyl group, 4-n-butoxy-1-naphthyl group, 5-ethoxy-1- Butyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n-hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy- 2-naphthyl group, 2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxy Phenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4- Methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-ethoxy Phenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl Group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-chloro-1-naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3- Difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl Group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,3,6-tribromophenyl group, 3,4,5-trifluorophenyl group, 2,4-dichloro-1-naphthyl group, 1,6-dichloro-2-naphthyl group, 2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 3-fluoro-2-methylphenyl Group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group Group, 2-chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4-chloro-3-methylphenyl group, 2-chloro- , 6-Dimethylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 5-chloro-2-methoxyphenyl group, 6-chloro -3-methoxyphenyl group, 5-chloro-2,4-dimethoxyphenyl group, 2-chloro-4-nitrophenyl group, 4-chloro-2-nitrophenyl group, 4-trifluoromethylphenyl group, 3-triphenyl Fluoromethylphenyl group, 2-trifluoromethylphenyl group, 3,5-bis (trifluoromethyl) phenyl group, 4-trifluoromethyloxyphenyl group, 4-allylphenyl group, 2-allylphenyl group, 2-iso Propenylphenyl group, 4-benzylphenyl group, 2-benzylphenyl group, 4- (4'-methylbenzyl) pheny Group, 4-cumylphenyl group, 4- (4′-methoxycumyl) phenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-ethylphenyl) phenyl group, 4- (4′-isopropylphenyl) phenyl group, 4- (4′-tert-butylphenyl) phenyl group, 4- (4′-n-hexylphenyl) phenyl group, 4- (4′-n-octylphenyl) phenyl group, 4- (4′-methoxyphenyl) phenyl group, 4- (4′-ethoxyphenyl) phenyl group, 4- (4′-n-butoxyphenyl) phenyl Group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-fluorophenyl) phenyl group, 4- (4′-chlorophenyl) phenyl group, 3-methyl-4-pheny Group, 2-methoxy-5-phenylphenyl group, 3-methoxy-4-phenylphenyl group, 4-methoxymethylphenyl group, 4-ethoxymethylphenyl group, 4-n-butoxymethylphenyl group, 3-methoxymethylphenyl Group, 4- (2′-methoxyethyl) phenyl group, 4- (2′-ethoxyethyloxy) phenyl group, 4- (2′-n-butoxyethyloxy) phenyl group, 4- (3′-ethoxypropyl) Oxy) phenyl group, 4-vinyloxyphenyl group, 4-allyloxyphenyl group, 3-allyloxyphenyl group, 4- (4′-pentenyloxy) phenyl group, 4-allyloxy-1-naphthyl group, 4-allyl Oxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group, 4-benzyloxyphenyl group, 2-benzyl An oxyphenyl group, a 4-phenethyloxyphenyl group, a 4- (4′-chlorobenzyloxy) phenyl group, a 4- (4′-methylbenzyloxy) phenyl group, a 4- (4′-methoxybenzyloxy) phenyl group, 4- (3′-ethoxybenzyloxy) phenyl group, 4-benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, 6-benzyloxy-2-naphthyl group, 6 -(4'-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4- (2'-benzyloxyethyloxy) phenyl group, 4 -Phenyloxyphenyl group, 3-phenyloxyphenyl group, 2-phenyloxyphenyl group, 4- (4'-methylphenyloxy) phenyl group 4- (4′-methoxyphenyloxy) phenyl group, 4- (4′-chlorophenyloxy) phenyl group, 4-phenyloxy-1-naphthyl group, 6-phenyloxy-2-naphthyl group, 7-phenyloxy- 2-naphthyl group, 4-phenyloxymethylphenyl group, 4- (2′-phenyloxyethyloxy) phenyl group, 4- [2 ′-(4′-methylphenyloxy) ethyloxy] phenyl group, 4- [2 '-(4'-methoxyphenyloxy) ethyloxy] phenyl group, 4- [2'-(4'-chlorophenyloxy) ethyloxy] phenyl group, 4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group 4-ethylcarbonylphenyl group, 2-ethylcarbonylphenyl group, 4-n-butylcarbonylphenyl group, 4-n- Xylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1-naphthyl group, 6-acetyl-2-naphthyl group, 6-n-butylcarbonyl-2-naphthyl group 4-arylcarbonylphenyl group, 4-benzylcarbonylphenyl group, 4- (4′-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4- (4′-methylphenyl) carbonylphenyl group, 4- (4′-chlorophenyl) carbonylphenyl group, 4-phenylcarbonyl-1-naphthyl group, 4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4- n-propoxycarbonylphenyl Group, 4-n-butoxycarbonylphenyl group, 4-n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6 -Methoxycarbonyl-2-naphthyl group, 6-n-butoxycarbonyl-2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4'-chlorobenzyl) oxycarbonylphenyl group 4-phenethyloxycarbonylphenyl group, 6-benzyloxycarbonyl-2-naphthyl group, 4-phenyloxycarbonylphenyl group, 4- (4′-ethylphenyl) oxycarbonylphenyl group, 4- (4′-chlorophenyl) Oxycarbonylphenyl group 4- (4'-ethoxyphenyl) oxycarbonyl phenyl group, 6-phenyl-oxycarbonyl-2-naphthyl group, 4-acetyloxy-phenyl group, 3-acetyloxy-phenyl group, 2-acetyl

Ruoxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2-ethylcarbonyloxyphenyl group, 4-n-propylcarbonyloxyphenyl group, 4-n-pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 4-n-butylcarbonyloxy-1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyloxyphenyl group, 4-phenethylcarbonyloxyphenyl group, 6-benzylcarbonyloxy 2-naphthyl group, 4-phenylcarbonyloxyphenyl group, 4- (4'-methylphenyl) carbonyloxyphenyl group, 4- (2'-methylphenyl) carbonyloxyphenyl group, 4- (4'-chlorophenyl) Carbonyloxyphenyl group, 4- (2′-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 7-phenylcarbonyloxy-2-naphthyl group 4-methylthiophenyl group, 2-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2-isopropylthiophenyl group, 4-n-butylthiophenyl group Group, 2-isobutylthiophenyl group, 2-neopentylpheny Group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group, 4- (4′-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2-phenylthiophenyl group, 4- (4′-methylphenylthio) phenyl group, 4- (3 ′ -Methylphenylthio) phenyl group, 4- (4'-methoxyphenylthio) phenyl group, 4- (4'-chlorophenylthio) phenyl group, 2-ethylthio-1-naphthyl group, 4-methylthio-1-naphthyl group 6-ethylthio-2-naphthyl group, 6-phenylthio-2-naphthyl group, 4-nitrophenyl group, 3-nitrophenyl group, 2-ni Trophenyl group, 3,5-dinitrophenyl group, 4-nitro-1-naphthyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formylphenyl group, 4-formyl-1-naphthyl group, 1- Formyl-2-naphthyl group, 4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N-ethylpiperazino) phenyl group, 4-pyrrolidino-1-naphthyl group, 4- Aminophenyl group, 3-aminophenyl group, 2-aminophenyl group, 4- (N-methylamino) phenyl group, 3- (N-methylamino) phenyl group, 4- (N-ethylamino) phenyl group, 2 -(N-isopropylamino) phenyl group, 4- (Nn-butylamino) phenyl group, 2- (Nn-butylamino) phenyl group, 4- (Nn- Cutylamino) phenyl group, 4- (Nn-dodecylamino) phenyl group, 4- (N-benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group 4- (N, N-dimethylamino) phenyl group, 3- (N, N-dimethylamino) phenyl group, 4- (N, N-diethylamino) phenyl group, 2- (N, N-dimethylamino) phenyl Group, 2- (N, N-diethylamino) phenyl group, 4- (N, N-di-n-butylamino) phenyl group, 4- (N, N-di-n-hexylamino) phenyl group, 4- (N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group, 4- (N, N- Gif Nylamino) phenyl group, 4- [N-phenyl-N- (4-methylphenyl) amino] phenyl group, 4- [N, N-di (3′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methoxyphenyl) amino] phenyl group, 2- (N, N-diphenylamino) phenyl group, 4- Hydroxyphenyl group, 3-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methyl-3-hydroxyphenyl group, 6-methyl-3-hydroxyphenyl group, 2-hydroxy-1-naphthyl group, 8-hydroxy-1 -Naphtyl group, 4-hydroxy-1-naphthyl group, 1-hydroxy-2-naphthyl group, 6-hydroxy-2-naphthyl group, 4-cyanophenyl group, 2-cyanophenyl An aryl group optionally having substituents such as a group, 4-cyano-1-naphthyl group, 6-cyano-2-naphthyl group;

For example, phenyloxy group, 2-methylphenyloxy group, 3-methylphenyloxy group, 4-methylphenyloxy group, 4-ethylphenyloxy group, 4-n-propylphenyloxy group, 4-isopropylphenyloxy group, 4-n-butylphenyloxy group, 4-tert-butylphenyloxy group, 4-isopentylphenyloxy group, 4-tert-pentylphenyloxy group, 4-n-hexylphenyloxy group, 4-cyclohexylphenyloxy group 4-n-octylphenyloxy group, 4-n-decylphenyloxy group, 4-n-octadecylphenyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5- Dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 5-i Danyloxy group, 1,2,3,4-tetrahydro-5-naphthyloxy group, 1,2,3,4-tetrahydro-6-naphthyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4 -Methoxyphenyloxy group, 3-ethoxyphenyloxy group, 4-ethoxyphenyloxy group, 4-n-propoxyphenyloxy group, 4-isopropoxyphenyloxy group, 4-n-butoxyphenyloxy group, 4-n- Pentyloxyphenyloxy group, 4-n-hexyloxyphenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-n-heptyloxyphenyloxy group, 4-n-octyloxyphenyloxy group, 4-n-decyloxy Phenyloxy group, 2,3-dimethoxyphenyloxy group, 2,5-dimethyl Xiphenyloxy group, 3,4-dimethoxyphenyloxy group, 2-methoxy-5-methylphenyloxy group, 3-methyl-4-methoxyphenyloxy group, 2-fluorophenyloxy group, 3-fluorophenyloxy group, 4-fluorophenyloxy group, 2-chlorophenyloxy group, 3-chlorophenyloxy group, 4-chlorophenyloxy group, 4-bromophenyloxy group, 4-trifluoromethylphenyloxy group, 3,4-dichlorophenyloxy group, 2 -Methyl-4-chlorophenyloxy group, 2-chloro-4-methylphenyloxy group, 3-chloro-4-methylphenyloxy group, 2-chloro-4-methoxyphenyloxy group, 4-phenylphenyloxy group, 3 -Phenylphenyloxy group, 4- (4'-methylphenyl) ) Phenyloxy group, 4- (4′-methoxyphenyl) phenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-ethoxy-1-naphthyloxy group, 6-methoxy-2-naphthyloxy group, Substituents such as 7-ethoxy-2-naphthyloxy group, 2-furyloxy group, 2-thienyloxy group, 3-thienyloxy group, 2-pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group An aryloxy group which may have;

For example, phenylthio group, 3-methylphenylthio group, 4-methylphenylthio group, 4-ethylphenylthio group, 4-n-propylphenylthio group, 4-n-butylphenylthio group, 4-tert-butylphenyl Thio group, 4-n-hexylphenylthio group, 4-cyclohexylphenylthio group, 4-n-octylphenylthio group, 4-n-dodecylphenylthio group, 4-n-octadecylphenylthio group, 2,3- Dimethylphenylthio group, 3,4-dimethylphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 3-ethoxyphenylthio group, 4-ethoxyphenylthio group, 4-n-propoxyphenylthio group 4-n-butoxyphenylthio group, 4-n-hexyloxyphenylthio group, 4-n-octyloxy Phenylthio group, 4-n-decyloxyphenylthio group, 3,4-dimethoxyphenylthio group, 3-methyl-4-methoxyphenylthio group, 3-fluorophenylthio group, 4-fluorophenylthio group, 4-chlorophenyl Thio group, 2-methyl-4-chlorophenylthio group, 2-chloro-4-methoxyphenylthio group, 4-phenylphenylthio group, 4- (4′-methylphenyl) phenylthio group, 4- (4′-methoxy) An arylthio group optionally having a substituent such as a phenyl) phenylthio group, a 1-naphthylthio group, a 2-naphthylthio group;

For example, N-methylamino group, N-ethylamino group, N-isopropylamino group, Nn-butylamino group, Nn-hexylamino group, Nn-decylamino group, Nn-tetradecylamino group Group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-butylamino group, N, N-di-n-hexylamino group, N, N-di-n-octyl Amino group, N, N-di-n-decylamino group, N, N-di-n-dodecylamino group, N-phenylamino group, N- (4-methylphenyl) amino group, N-phenyl-N-methyl Amino group, N-phenyl-N-ethylamino group, N, N-diphenylamino group, N, N-di (4-methylphenyl) amino group, N, N-di (4-ethylphenyl) amino group, N , N-di (4-methoxyphenyl) Amino group, an amino group which may have a substituent such as a substituted amino group or an amino group such as N- phenyl -N- naphthylamino group; a cyano group, a hydroxyl group, a nitro group;

For example, carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-octyloxycarbonyl group 2-ethylhexyloxycarbonyl group, n-decyloxycarbonyl group, n-dodecyloxycarbonyl group, n-tetradecyloxycarbonyl group, n-hexadecyloxycarbonyl group, n-octadecyloxycarbonyl group, cyclohexyloxycarbonyl group, Benzyloxycarbonyl group, phenethyloxycarbonyl group, (4-methylbenzyloxy) carbonyl group, (3-methylbenzyloxy) carbonyl group, (4-tert-butylbenzyloxy) Rubonyl group, (4-methoxybenzyloxy) carbonyl group, (4-chlorobenzyloxy) carbonyl group, phenyloxycarbonyl group, (4-methylphenyloxy) carbonyl group, (3-methylphenyloxy) carbonyl group, (4 -Ethylphenyloxy) carbonyl group, (4-tert-butylphenyloxy) carbonyl group, (4-methoxyphenyloxy) carbonyl group, (2-methoxyphenyloxy) carbonyl group, (4-ethoxyphenyloxy) carbonyl group, -COOR ₃ group such as (4-fluorophenyloxy) carbonyl group (wherein R ₃ represents the same as above);

For example, formyl group, methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, n-butylcarbonyl group, n-hexylcarbonyl group, n-octylcarbonyl group, 2-ethylhexylcarbonyl group, n-decylcarbonyl group, n -Dodecylcarbonyl group, n-tetradecylcarbonyl group, n-hexadecylcarbonyl group, n-octadecylcarbonyl group, cyclohexylcarbonyl group, benzylcarbonyl group, phenethylcarbonyl group, (4-methylbenzyl) carbonyl group, (4-tert -Butylbenzyl) carbonyl group, (4-methoxybenzyl) carbonyl group, (4-chlorobenzyl) carbonyl group, phenylcarbonyl group, (4-methylphenyl) carbonyl group, (3-methylphenyl) carbonyl group, (4- D Ruphenyl) carbonyl group, (4-tert-butylphenyl) carbonyl group, (4-methoxyphenyl) carbonyl group, (2-methoxyphenyl) carbonyl group, (4-ethoxyphenyl) carbonyl group, (4-fluorophenyl) carbonyl -COR ₄ group such as a group, amide, substituted amide, etc. (in the group, R ₄ represents the same as above);

For example, methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, n-butylcarbonyloxy group, n-pentylcarbonyloxy group, n-hexylcarbonyloxy group, n-octylcarbonyloxy group, 2-ethylhexyl Carbonyloxy group, n-decylcarbonyloxy group, n-dodecylcarbonyloxy group, n-tetradecylcarbonyloxy group, n-hexadecylcarbonyloxy group, n-octadecylcarbonyloxy group, cyclohexylcarbonyloxy group, benzylcarbonyloxy group , Phenethylcarbonyloxy group, (4′-methylbenzylcarbonyl) oxy group, (4′-tert-butylbenzylcarbonyl) oxy group, (4′-methoxybenzylcarbonyl) oxy group, (4′-alkyl) (Rorobenzylcarbonyl) oxy group, phenylcarbonyloxy group, (4′-methylphenylcarbonyl) oxy group, (3′-methylphenylcarbonyl) oxy group, (4′-ethylphenylcarbonyl) oxy group, (4′-tert) -Butylphenylcarbonyl) oxy group, (4'-methoxyphenylcarbonyl) oxy group, (2'-methoxyphenylcarbonyl) oxy group, (4'-ethoxyphenylcarbonyl) oxy group, (4'-fluorophenylcarbonyl) oxy (wherein, R ₅ represents the same as described above) -OCOR ₅ groups, such groups can be exemplified.
In the general formula (1), X _{1 to} X ₄ and Y _{1 to} Y ₄ may be the same group, or may be different from each other.

〔上記一般式（１’）中、Ｒ₁およびＲ₂、Ｘ₁〜Ｘ₄およびＹ₁〜Ｙ₄は、それぞれ、一般式（１）と同様のものを表わす。〕 Further, as the green organic phosphor, a tautomer of the above pyridine-phthalimide condensed derivative may be used. The tautomer of the pyridine-phthalimide condensed derivative refers to a compound having a structure represented by the following general formula (1 ′) in the compound represented by the general formula (1).

[In the general formula (1 ′), R ₁ and R ₂ , X _{1 to} X ₄ and Y _{1 to} Y ₄ are the same as those in the general formula (1). ]

Moreover, when using the above-mentioned various pyridine-phthalimide condensed derivatives having X _{1 to} X ₄ and Y _{1 to} Y ₁₀ , or tautomers thereof as a green organic phosphor, they are used alone. Two or more kinds may be used in any combination and ratio.

  Specific examples of such pyridine-phthalimide condensation derivatives include the following compounds. However, the present invention is not limited to these. Further, specific examples are represented by the skeleton of the general formula (1), but tautomers of these compounds are also included.

  The method for producing the above-mentioned pyridine-phthalimide condensed derivative is not limited, but for example, JP-A-56-147784, JP-A-10-226691, JP-A-11-116568, JP-A-11-116569. And can be produced according to the operation described in JP-A-11-158185. That is, for example, a phthalimide derivative represented by the following general formula (2) and a pyridine derivative represented by the general formula (3) in the presence of an organic basic solvent (for example, pyridine, quinoline) zinc halide ( For example, by reacting with zinc chloride or zinc bromide) and then treating with an inorganic acid (for example, hydrochloric acid, sulfuric acid or nitric acid), the pyridine-phthalimide condensed derivative represented by the general formula (1) and its tautomerism A sex body can be produced.

〔一般式（２）中、Ｒ₂およびＹ₁〜Ｙ₄は、それぞれ、一般式（１）と同様のものを表わす。〕

[In General Formula (2), R ₂ and Y _{1 to} Y ₄ each represent the same as in General Formula (1). ]

〔一般式（３）中、Ｒ₁およびＸ₁〜Ｘ₄は、それぞれ、一般式（１）と同様のものを表わす。〕

[In General Formula (3), R ₁ and X _{1 to} X ₄ each represent the same as in General Formula (1). ]

  The pyridine-phthalimide condensed derivative as described above is sometimes produced in a form in which a solvate with a used solvent (for example, an aromatic hydrocarbon solvent such as toluene) is formed. In the present invention, such a pyridine-phthalimide condensation derivative solvate or a solvent-free solvate can be used. Further, it is preferable to use a recrystallization method, a column chromatography method, a purification method such as a sublimation purification method, or a compound having an increased purity by using these methods in combination.

  Further, as the green phosphor, a green organic phosphor other than the pyridine-phthalimide condensed derivative described above can be used. For example, as the green phosphor, it is possible to use a benzoxazinone-based, quinazolinone-based, coumarin-based, quinophthalone-based, naltalimide-based, or the like, or an organic phosphor such as a terbium complex.

  Furthermore, it is also possible to use a green inorganic phosphor other than the green organic phosphor as the green phosphor. For example, it absorbs at least part of light from a light source that emits light having a peak wavelength in the range of 350 nm to 420 nm, and is green (center wavelength is usually 490 nm or more, preferably 500 nm or more, Inorganic phosphors emitting light of 570 nm or less, preferably 560 nm or less.

As such a green inorganic phosphor, for example, europium which is composed of fractured particles having a fracture surface and emits light in the green region is represented by (Mg, Ca, Sr, Ba) Si ₂ O ₂ N ₂ : Eu. Europium activated alkaline earth magnesium silicate composed of activated alkaline earth silicon oxynitride phosphor, broken particles having fractured surface, and emitting in the green region (Ba, Ca, Sr) ₂ SiO ₄ : Eu System phosphors and the like.

In addition, as the green phosphor, Sr ₄ Al ₁₄ O ₂₅ : Eu, (Sr, Ba) Al ₂ Si ₂ O ₈ : Eu, (Ba, Mg) ₂ SiO ₄ : Eu, Y ₂ SiO ₅ : Ce _{, Tb, Sr 2 P 2 O} 7 -Sr 2 B 2 O 5: Eu, Sr 2 Si 3 O 8 -2SrCl 2: Eu, Zn 2 SiO 4: Mn, CeMgAl 11 O 19: Tb, (Ba, Sr, _{Ca, Mg) 2 SiO 4:} Eu, Ca 2 Y 8 (SiO 4) 6 O 2: Tb, Y 3 Al 5 O 12: Tb, La 3 Ga 5 SiO 14: Tb, (Sr, Ba, Ca) Ga ₂ S ₄ : Eu, Tb, Sm, Y ₃ (Al, Ga) ₅ O ₁₂ : Ce, Ca ₃ Sc ₂ Si ₃ O ₁₂ : Ce, Ca ₃ (Sc, Mg, Na, Li) ₂ Si ₃ O _{12 : Ce, CaSc 2 O 4:} Ce, SrSi 2 O 2 N 2: Eu, (Sr, Ba, Ca) Si 2 O 2 N 2: E _{, BaMgAl 10 O 17: Eu,} Mn, SrAl 2 O 4: Eu, (La, Gd, Y) 2 O 2 S: Tb, LaPO 4: Ce, Tb, ZnS: Cu, Al, ZnS: Cu, Au, Al, Y ₂ SiO ₅ : Ce, Tb, Eu activated β sialon, Eu activated α sialon, (Ba, Sr, Ca) Al ₂ O ₄ : Eu, (Y, Ga, Lu, Sc, La) BO ₃ : Ce, Tb, Ca ₈ Mg (SiO ₄ ) ₄ Cl ₂ : Eu, Mn, (Ba, Sr, Ca) ₂ (Mg, Zn) Si ₂ O ₇ : Eu, (Sr, Ca, Ba) (Al, _{Ga, In) 2 S 4:} Eu, (Y, Ga, Tb, La, Sm, Pr, Lu) 3 (Al, Ga) 5 O 12: Ce, (Ca, Sr) 8 (Mg, Zn) (SiO _{4) 4 Cl 2: Eu,} Mn, Na 2 Gd 2 B 2 O 7: Ce, Tb, (Ba, Sr) 2 (Ca, _{g, Zn) B 2 O 6} : It is possible to use K, Ce, and Tb, and the like.

  In addition, a green fluorescent substance may be used individually by 1 type, and may use 2 or more types together.

[2-2. Red phosphor]
When a red phosphor is used, a phosphor that emits light by absorbing at least part of light from a light source that emits light having a peak wavelength in the range of 350 nm to 420 nm is used. At this time, a red organic phosphor is preferably used as the red phosphor.

  As the red organic phosphor, those emitting light having a peak wavelength in the range of usually 550 nm or more, preferably 600 nm or more, and usually 700 nm or less, preferably 680 nm or less are desirable.

  Moreover, although there is no restriction | limiting in the luminous efficiency of red organic fluorescent substance, it is desirable to use a thing with high luminous efficiency. Specifically, a phosphor having a luminous efficiency of usually 20% or more, preferably 30% or more, more preferably 45% or more is used. Thus, by using a red phosphor with high light emission efficiency, the amount of phosphor used can be reduced, and a light emitting device with high luminance can be manufactured even when the power of the light source is small.

  Examples of red organic phosphors that can be used in the present invention include red ions composed of rare earth element ion complexes having an anion such as β-diketonate, β-diketone, aromatic carboxylic acid, or Bronsted acid as a ligand. Organic phosphors are mentioned.

  Here, as rare earth elements in the rare earth element ion complex, cerium (Ce), praseodymium (Pr), neodymium (Nd), samarium (Sm), europium (Eu), terbium (Tb), dysprosium (Dy), holmium ( Elements such as Ho), erbium (Er), thulium (Tm), ytterbium (Yb) can be used. Among them, europium (Eu) is preferably used because it becomes a red phosphor that emits light with high luminance when irradiated with near ultraviolet light.

(I) Description of rare earth element ion complex having β-diketonate anion as ligand Among rare earth element ion complexes usable as red organic phosphor, rare earth element ion complex having β-diketonate anion as ligand ( An example of a rare earth element ion complex having an anion derived from β-diketonate as a ligand; a diketonate complex) is represented by the general formula Eu (β-diketonate) ₃ L _n and is derived from a β-diketone compound. The complex which makes (beta) -diketonate anion a ligand is mentioned. Here, L represents a neutral ligand having monodentate or multidentate, and n represents 1 or 2.

  Further, the β-diketone compound from which the anion of β-diketonate is derived is optional as long as the effects of the present invention are not significantly impaired. From the viewpoint of the excitation wavelength range, the structure includes at least a β-diketone structure, It is preferable to have one aromatic ring or aromatic heterocyclic ring (hereinafter referred to as “aromatic group” where appropriate) which may have a substituent as a substituent. The β-diketone structure and the aromatic group may be linked directly or with a divalent group, but preferably has an aromatic ring directly linked to at least one ketone.

  The kind of the aromatic group is arbitrary as long as the effects of the present invention are not significantly impaired. However, among the aromatic groups, examples of the aromatic ring include aromatic monocyclic hydrocarbons such as benzene, naphthalene, phenanthrene, indene, biphenylene, acenaphthene, fluorene, tetralin, and indane, or aromatic condensed polycyclic carbonization. Hydrogen is mentioned. On the other hand, among aromatic groups, examples of the aromatic heterocycle include furan, pyrrole, thiophene, oxazole, isoxazole, thiazole, imidazole, pyridine, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzopyran, carbazole, xanthene, Aromatic monocyclic heterocycles such as quinoline and triazine or aromatic condensed polycyclic heterocycles.

  Further, as described above, the aromatic group (that is, the aromatic ring or the aromatic heterocyclic ring) may have a substituent. Under the present circumstances, the substituent of an aromatic group is arbitrary unless the effect of this invention is impaired remarkably. For example, alkyl groups such as methyl, ethyl, propyl and butyl; fluoroalkyl groups such as trifluoromethyl and pentafluoroethyl; ethynyl groups; arylethynyl groups such as phenylethynyl, pyridylethynyl and thienylethynyl; methoxy, Alkoxy groups such as ethoxy; aryl groups such as phenyl and naphthyl groups; aralkyl groups such as benzyl and phenethyl; aryloxy groups such as phenoxy, naphthoxy and biphenyloxy; hydroxyl groups; allyl groups; acetyl, propionyl, benzoyl, toluoyl and the like Acyl groups; acyloxy groups such as acetoxy, propionyloxy, benzoyloxy; alkoxycarbonyl groups such as methoxycarbonyl and ethoxycarbonyl; aryloxycarbonyl groups such as phenoxycarbonyl; Carboxyl group; amino group; substituted amino group such as dimethylamino, diethylamino, methylbenzylamino, diphenylamino, acetylmethylamino; substituted thio group such as methylthio, ethylthio, phenylthio, benzylthio; mercapto group; ethylsulfonyl, phenyl Examples thereof include substituted sulfonyl groups such as sulfonyl; cyano groups; halogen groups such as fluoro, chloro, bromo and iodo. These substituents may be bonded to each other to form a ring.

  Moreover, the β-diketone compound from which the anion of β-diketonate is derived may have a group other than the aromatic group. Examples of the group other than the aromatic group that constitutes the β-diketone compound include the same substituents as those for the aromatic ring or aromatic heterocyclic ring described above (excluding the halogen group).

Specific examples of the β-diketone compound from which the β-diketonate anion is derived are shown below, but the present invention is not limited to these compounds.

Furthermore, in the above general formula "Eu (beta-diketonate) ₃ L _n", neutral ligand L, as long as a neutral ligand, using any one that does not significantly impair the effects of the present invention be able to. However, it is usually a compound having atoms such as N and O that can be coordinated to Eu ³⁺ . For example, amine, amine oxide, phosphine oxide, ketone, sulfoxide, ether and the like can be mentioned. In addition, these may be used individually by 1 type and may be used in combination of 2 or more type. However, the neutral ligand L is selected so that the total coordination number to Eu ³⁺ is 7 or 8.

Specific examples of the neutral ligand L include, for example, amines such as pyridine, pyrazine, quinoline, isoquinoline, 2,2′-bipyridine, 1,10-phenanthroline, which may have a substituent.
Further, for example, as amine oxide, pyridine-N-oxide, isoquinoline-N-oxide, 2,2′-bipyridine-N, N′-dioxide, which may have a substituent, 1,10-phenanthroline-N, N Examples include N-oxides of the above amines such as' -dioxide.

  Further, for example, phosphine oxide includes alkyl phosphine oxides such as triphenylphosphine oxide, triethylphosphine oxide and trioctylphosphine oxide which may have a substituent; 1,2-ethylenebis (diphenylenephosphine oxide), (diphenylphosphine oxide). Phonimide) triphenylphosphorane, phosphoric acid triphenyl ester and the like.

Examples of the ketone include dipyridyl ketone and benzophenone which may have a substituent.
Furthermore, examples of the sulfoxide include diphenyl sulfoxide, dibenzyl sulfoxide, and dioctyl sulfoxide, which may have a substituent.
Examples of the ether include ethylene glycol dimethyl ether and diethylene glycol dimethyl ether which may have a substituent.

Further, when these neutral ligands L have a substituent, examples of the substituent include those described above as the substituent of the aromatic group.
Specific examples of the neutral ligand L are shown below, but the present invention is not limited to these compounds.

(Ii) Description of Rare Earth Element Ion Complexes with β-Diketone Anions as Ligands Among rare earth element ion complexes that can be used as red organic phosphors, complexes with β-diketone anions as ligands (β-diketone) Examples of the complex having an anion derived from a ligand as a ligand; β-diketone complex) include a europium complex represented by any one of the following general formulas (4), (5), and (6). .
(R ¹ ) ₃ Eu (4)
(R ¹ ) ₃ Eu (R ² ) ₂ (5)
[(R ¹ ) ₄ Eu] ^- (R ³ ) ⁺ (6)
[In the formulas (4), (5) and (6), R ¹ represents an anion of a β-diketone having a substituent containing an aromatic ring, R ² represents an auxiliary ligand comprising a Lewis base, (R ³ ) ⁺ represents a quaternary ammonium ion. ]

R ¹ in the general formulas (4), (5), and (6) represents a β-diketone having a substituent containing an aromatic ring. That is, R ¹ represents a β-diketone having a substituent containing an aromatic ring. Examples of the aromatic ring in R ¹ include aromatic heterocyclic compounds, heterocyclic condensed aromatic hydrocarbon compounds, and the like in addition to aromatic hydrocarbon compounds. Therefore, R ¹ may contain at least one of these aromatic rings.

When the example of the aromatic ring in R ¹ is given, examples of the aromatic hydrocarbon compound include benzene, naphthalene, phenanthrene and the like. Examples of aromatic heterocyclic compounds include heterocyclic compounds containing oxygen, sulfur, and nitrogen atoms such as furan, thiophene, pyrazoline, and pyridine. Furthermore, examples of the heterocyclic condensed aromatic hydrocarbon compound include carbazole, dibenzofuran, dibenzothiophene, and the like.

Moreover, the aromatic ring in R ¹ may have a substituent. The type of the substituent is arbitrary as long as the effects of the present invention are not significantly impaired. Examples thereof include alkyl groups such as methyl, ethyl, propyl, and butyl; fluoroalkyl groups such as trifluoromethyl and pentafluoromethyl; methoxy and ethoxy Alkoxy groups such as benzyl, phenethyl and the like; aryloxy groups such as phenoxy, naphthoxy and biphenyloxy; hydroxyl groups; allyl groups; acyl groups such as acetyl and propionyl; acyloxy groups such as acetoxy, propionyloxy and benzoyloxy Alkoxycarbonyl groups such as methoxycarbonyl and ethoxycarbonyl; aryloxycarbonyl groups such as phenoxycarbonyl; carboxyl group; carbamoyl group; amino group; dimethylamino, diethylamino, methylbenzylamino, Substituted amino groups such as phenylamino and acetylmethylamino; substituted thio groups such as methylthio, ethylthio, phenylthio and benzylthio; mercapto groups; substituted sulfonyl groups such as ethylsulfonyl and phenylsulfonyl; cyano groups; fluoro, chloro, bromo and iodo And the like. These substituents may be bonded to each other to form a ring.

In the general formulas (4), (5), and (6), R ¹ may have a substituent other than a substituent containing an aromatic ring. Examples of such a substituent include the same substituents as those exemplified as the substituent for the aromatic ring (however, a halogen group is excluded).

Specific examples of R ^{1 in} the general formulas (4), (5), and (6) are shown below. However, the present invention is not limited to these.

R ² in the general formula (5) represents an auxiliary ligand composed of a Lewis base. The specific type of R ² is arbitrary as long as the effect of the present invention is not significantly impaired, but is usually selected from a Lewis base compound having a nitrogen atom or an oxygen atom that can be coordinated to a europium ion. Examples thereof include an amine that may have a substituent, an amine oxide that may have a substituent, a phosphine oxide that may have a substituent, and an amine that may have a substituent. Examples thereof include sulfoxide. Two Lewis base compounds as auxiliary ligands may be different compounds, or two compounds may form one compound.

Specific examples of R ² include amines such as pyridine, pyrazine, quinoline, isoquinoline, phenanthridine, 2,2′-bipyridine, and 1,10-phenanthroline. Examples of the amine oxide include N-oxides of the amines such as pyridine-N-oxide and 2,2′-bipyridine-N, N′-dioxide. Furthermore, examples of the phosphine oxide include triphenylphosphine oxide, trimethylphosphine oxide, trioctylphosphine oxide, and the like. Examples of the sulfoxide include diphenyl sulfoxide and dioctyl sulfoxide.

Among these Lewis bases, two compounds such as bipyridine and phenanthroline that have two coordinated atoms (for example, a nitrogen atom) in the molecule can be supplemented with two Lewis bases. You may make it function like a ligand.
Moreover, as these substituents, the same substituents as mentioned as the substituent of the aromatic ring in the general formula (4) can be mentioned. Of these, an alkyl group, an aryl group, an alkoxyl group, an aralkyl group, an aryloxy group, a halogen group and the like are preferable.

Specific examples of R ² in the general formula (5) are shown below. However, the present invention is not limited to these.

R ³ in the general formula (6) represents a quaternary ammonium ion. Specific examples of R ³ include quaternary ammonium salts derived from alkylamines, arylamines, aralkylamines and the like. Moreover, these amines may have a substituent. As substituents of these amines, alkyl groups such as methyl, ethyl, propyl, butyl, hexyl and octyl; substituted alkyl groups such as hydroxyethyl and methoxyethyl; aryl groups such as phenyl and tolyl; benzyl and phenethyl groups and the like Aralkyl group and the like can be mentioned.

(Iii) Rare earth element ion complex having an anion of aromatic carboxylic acid as a ligand Among rare earth element ion complexes that can be used as a red organic phosphor, aromatic carboxylic acid (carboxylic acid having a substituent containing an aromatic ring) As a complex having an anion of the above (a complex having an anion derived from an aromatic carboxylic acid as a ligand; an aromatic carboxylic acid complex), for example, a europium complex represented by the following general formula (7) Is mentioned.
[R ⁴ - (X) _n -COO] _{^{3 Eu (R 5) 2 (}} 7)
[In the general formula (7), R ⁴ represents a monovalent group containing an aromatic ring, X represents a divalent linking group, n is 0 or 1, and R ⁵ is an auxiliary consisting of a Lewis base. Indicates a ligand. ]

  The europium complex represented by the general formula (7) includes an aromatic ring, has 8 or more π electrons, and has a carboxylate ion constituting a π electron conjugated system as a ligand. From the point of view, it is preferable. The number of aromatic rings as aromatic monocycles is not particularly limited as long as the triplet energy of the carboxylate ion parent compound is higher than the europium ion excited state energy level, but usually 3 or less. Is preferred. When the number of aromatic monocycles is 4 or more, for example, a compound such as pyrene having four benzene rings is excited by absorbing light from the first light emitter such as a semiconductor light emitting device. There is a possibility that the energy is lowered and the europium complex does not emit light.

In the general formula (7), R ⁴ represents a monovalent group containing an aromatic ring. Among these, those having 3 or less aromatic monocycles are preferred. Examples of the aromatic ring include aromatic monocyclic hydrocarbon compounds such as benzene, naphthalene, indene, biphenylene, acenaphthene, fluorene, phenanthrene, tetralin, and indane, and aromatic condensed polycyclic hydrocarbon compounds, benzoquinone, naphthoquinone, and the like. , Derivatives from aromatic hydrocarbon compounds such as anthraquinone, aromatic monocyclic heterocyclic compounds such as furan, pyrrole, thiophene, oxazole, isoxazole, thiazole, imidazole, pyridine, triazine, benzofuran, benzothiophene, coumarin, benzopyran, Heterocyclic fused aromatic hydrocarbon compounds such as carbazole, xanthene, and quinoline.

  Moreover, these aromatic rings may have a substituent. Examples of the substituent include alkyl groups such as methyl, ethyl, propyl, and butyl; fluoroalkyl groups such as trifluoromethyl and pentafluoroethyl; cycloalkyl groups such as cyclohexyl group; ethynyl group; phenylethynyl, pyridylethynyl, Arylethynyl groups such as thienylethynyl; alkoxy groups such as methoxy and ethoxy; aryl groups such as phenyl and naphthyl; aralkyl groups such as benzyl and phenethyl; aryloxy groups such as phenoxy, naphthoxy and biphenyloxy; hydroxyl groups; Acyl groups such as acetyl, propionyl, benzoyl, toluoyl and biphenylcarbonyl; acyloxy groups such as acetoxy, propionyloxy and benzoyloxy; alkoxy groups such as methoxycarbonyl and ethoxycarbonyl Bonyl group; aryloxycarbonyl group such as phenoxycarbonyl; carboxyl group; carbamoyl group; amino group; substituted amino group such as dimethylamino, diethylamino, methylbenzylamino, diphenylamino, acetylmethylamino; methylthio, ethylthio, phenylthio, benzylthio, etc. Substituted thio groups; mercapto groups; substituted sulfonyl groups such as ethylsulfonyl and phenylsulfonyl groups; cyano groups; halogen groups such as fluoro, chloro, bromo, iodo and the like. These substituents further have a substituent. It may be. Among these, an alkyl group, an alkoxy group, an aryl group, a cycloalkyl group, an aryloxy group, an aralkyl group, an ethynyl group, and a halogen group are preferable.

In the general formula (7), X represents a divalent linking group. Further, in the general formula (7), n represents 0 or 1. Therefore, the carboxylate ion in the general formula (7) is classified into a case where it does not have X which is a divalent linking group (n = 0) and a case where it has (n = 1). Furthermore, when X is a divalent linking group (n = 1), X is classified into two types of forms, that is, a case where X has a carbonyl group and a case where X does not. For this reason, the carboxylate ion [R ⁴ — (X) _n —COO] ⁻ in the general formula (7) further includes the following general formula (8) having no carbonyl group and the following general formula ( 9). The europium complex represented by the general formula (7) may have any of complex structures having these carboxylate ions as ligands.

R ⁴ —R ⁶ —COO ⁻ (8)
R ⁴ —CO— (R ⁶ ) _m —COO ⁻ (9)
[In formulas (8) and (9), R ⁴ is the same as in formula (7), R ⁶ represents a divalent linking group, and m is 0 or 1. ]

Examples of the divalent linking group as R ⁶ in the general formulas (8) and (9) include, for example, alkylene groups such as methylene and ethylene, and ring assembly carbonization such as biphenyl, terphenyl, binaphthyl, cyclohexylbenzene, and phenylnaphthalene. Divalent groups derived from hydrogen compounds, divalent groups derived from cycloaliphatic hydrocarbon compounds such as cyclopentane, cyclohexane, cycloheptane, norbornane, bicyclohexyl, etc., the same as mentioned as specific examples of the aromatic ring described above A divalent group derived from the above compound, a divalent group derived from an aliphatic heterocyclic compound such as pyrazolidine, piperazine, imidazolidine and morpholine, a thioalkylene group such as —SCH ₂ —, and an oxy such as —OCH ₂ —. Examples include an alkylene group and a vinylene group. Further, these divalent linking groups may have a substituent.

Further, in the general formula (7), R ⁵ represents an auxiliary ligand composed of a Lewis base. This R ⁵ is the same as R ² in the general formula (5).

  Specific examples of the carboxylic acid from which the carboxylic acid ion in the general formula (7) is derived are shown below. It should be noted that the present embodiment is not limited to these.

Examples of the carboxylic acid when n is 0 in the general formula (7) include the following compounds.

Also, the a general formula (7) n is 1 in the case X is R ^6, the carboxylic acid represented by the general formula (8) include the following compounds.

In the general formula (9), examples of the carboxylic acid when m is 0 include the following compounds.

In the general formula (9), examples of the carboxylic acid when m is 1 include the following compounds.

(Iv) Rare earth element ion complexes with Bronsted acid anions as ligands Among rare earth element ion complexes that can be used as red organic phosphors, complexes with Bronsted acid anions as ligands (derived from Bronsted acids) Examples of the complex having an anion to be a ligand; Bronsted acid complex) include red organic phosphors described in JP-A-2005-8872.

(V) Other rare earth element ion complexes Further, other rare earth element ion complexes such as a rare earth element ion complex having an anion having no aromatic ring as a ligand can also be used. For example, a rare earth element ion complex having acetylacetonate having an electron withdrawing group as a ligand, preferably a rare earth element ion complex having hexafluoroacetylacetonate as a ligand can be used.

(Vi) Examples of preferred red organic phosphors Among the red organic phosphors described above, the following red organic phosphors are particularly preferred.

(Vii) Others Further, as the red phosphor, it is also possible to use a red organic phosphor other than the rare earth element ion complex described above. For example, red organic phosphors include perylene pigments (for example, dibenzo {[f, f ′]-4,4 ′, 7,7′-tetraphenyl} diindeno [1,2,3-cd: 1 ′, 2 ', 3'-lm] perylene), anthraquinone pigment, lake pigment, azo pigment, quinacridone pigment, anthracene pigment, isoindoline pigment, isoindolinone pigment, phthalocyanine pigment, triphenylmethane Basic dyes, indanthrone pigments, indophenol pigments, cyanine pigments and dioxazine pigments can also be used.

  As the red phosphor, a red phosphor other than the red organic phosphor described above can be used. For example, at least part of light from a light source that emits light having a peak wavelength in the range of 350 nm to 420 nm is absorbed, and red (center wavelength is usually 570 nm or more, preferably 580 nm or more, An inorganic phosphor that emits light of 700 nm or less, preferably 680 nm or less) can also be used.

As such a red inorganic phosphor, for example, europium composed of broken particles having a red fracture surface and emitting light in the red region (Mg, Ca, Sr, Ba) ₂ Si ₅ N ₈ : Eu. The activated alkaline earth silicon nitride phosphor is composed of growing particles having a substantially spherical shape as a regular crystal growth shape, and emits light in the red region (Y, La, Gd, Lu) ₂ O ₂ S: Eu And europium-activated rare earth oxychalugenite-based phosphors.

  Furthermore, the oxynitride and / or acid containing at least one element selected from the group consisting of Ti, Zr, Hf, Nb, Ta, W, and Mo described in JP-A-2004-300247 A phosphor containing a sulfide and containing an oxynitride having an alpha sialon structure in which a part or all of the Al element is substituted with a Ga element can also be used in this embodiment. These are phosphors containing oxynitride and / or oxysulfide.

In addition, as the red phosphor, (La, Y) ₂ O ₂ S: Eu, Y ₂ O ₃ : Eu, (Ba, Mg) ₂ SiO ₄ : Eu, Mn, (Ba, Sr, Ca, Mg) ₂ SiO ₄ : Eu, Mn, Y (V, P) O ₄ : Eu, (Ca, Sr) S: Eu, YAlO ₃ : Eu, Ca ₂ Y ₈ (SiO ₄ ) ₆ O ₂ : Eu, LiY ₉ (SiO ₄ ) ₆ O ₂ : Eu, (Y, Gd) ₃ Al ₅ O ₁₂ : Ce, (Tb, Gd) ₃ Al ₅ O ₁₂ : Ce, (Ca, Sr, Ba) ₂ Si ₅ N ₈ : Eu (Ca, Sr, Ba) SiN ₂ : Eu, (Ca, Sr, Ba) AlSiN ₃ : Eu, (Ca, Sr, Ba) AlSiN ₃ : Ce, (Sr, Ca, Ba, Mg) ₁₀ (PO _{4 ) 6 Cl 2: Eu, Mn} , (Ba 3 Mg) Si 2 O 8: Eu, Mn, 3.5MgO · 0.5MgF 2 · GeO 2: n, Eu-activated α-sialon, (Sr, Ba, Ca) 3 SiO 5: Eu, Sr 2 BaSiO 5: Eu, (Gd, Y, Lu, La) 2 O 3: Eu, Bi (Gd, Y, Lu , La) ₂ O ₂ S: Eu, Bi, (Gd, Y, Lu, La) VO ₄ : Eu, Bi, SrY ₂ S ₄ : Eu, Ce, CaLa ₂ S ₄ : Ce, (Ba, Sr, Ca _{) MgP 2 O 7: Eu,} Mn, (Y, Lu) 2 WO 6: Eu, Mo, (Ba, Sr, Ca) x Si y N z: Eu, Ce, (Ba, Sr, Ca, Mg) 3 (Zn, Mg) Si ₂ O ₈ : Eu, Mn, (Sr, Ca, Ba, Mg, Zn) ₂ P ₂ O ₇ : Eu, Mn, (Ca, Sr, Ba, Mg) ₁₀ (PO ₄ ) ₆ (F, Cl, Br, OH ): Eu, Mn, ((Y, Lu, Gd, Tb) 1-x Sc x Ce y) 2 (Ca, Mg) 1-r (Mg Zn) ₂ + r Si _zq Ge be used _q O _{12 + δ,} etc. are also possible.

  In addition, a red fluorescent substance may be used individually by 1 type, and may use 2 or more types together.

[2-3. Blue phosphor]
When a blue phosphor is used, a phosphor that emits light by absorbing at least part of light from a light source that emits light having a peak wavelength in the range of 350 nm to 420 nm is used.

  The blue phosphor desirably emits light having a peak wavelength in the range of usually 420 nm or more, preferably 440 nm or more, and usually 480 nm or less, preferably 470 nm or less.

As an example of a blue phosphor, europium-activated barium magnesium aluminate-based fluorescence expressed by BaMgAl ₁₀ O ₁₇ : Eu that is composed of growing particles having a substantially hexagonal shape as a regular crystal growth shape and emits light in the blue region. Europium-activated calcium halophosphate system represented by (Ca, Sr, Ba) ₅ (PO ₄ ) ₃ Cl: Eu, which is composed of grown particles having a substantially spherical shape as a regular crystal growth shape. A europium-activated alkaline earth represented by (Ca, Sr, Ba) ₂ B ₅ O ₉ Cl: Eu, which is composed of phosphors and growing particles having a substantially cubic shape as a regular crystal growth shape, and emits light in a blue region. It is composed of a chloroborate phosphor and fractured particles having a fracture surface, and emits light in the blue-green region (Sr, _{a, Ba) Al 2 O 4} : Eu or _{(Sr, Ca, Ba) 4} Al 14 O 25: europium-activated alkaline earth aluminate phosphors represented by Eu, and the like.

In addition, blue phosphors include Sr ₂ P ₂ O ₇ : Sn, Sr ₄ Al ₁₄ O ₂₅ : Eu, BaMgAl ₁₀ O ₁₇ : Eu, SrGa ₂ S ₄ : Ce, CaGa ₂ S ₄ : Ce, ( Ba, Sr, Ca) MgAl ₁₀ O ₁₇ : Eu, (Ba, Sr, Ca) MgAl ₁₀ O ₁₇ : Eu, Mn, (Sr, Ca, Ba, Mg) ₁₀ (PO ₄ ) ₆ Cl ₂ : Eu, BaAl ₂ Si ₂ O ₈ : Eu, BaMgAl ₁₀ O ₁₇ : Eu, Tb, Sm, (Sr, Ba) ₃ MgSi ₂ O ₈ : Eu, Sr ₂ P ₂ O ₇ : Eu, ZnS: Ag, ZnS: Ag, Al Y ₂ SiO ₅ : Ce, CaWO ₄ , (Ba, Sr, Ca) ₅ (PO ₄ ) ₃ (Cl, F, Br, OH): Eu, Mn, Sb, (Ba, Sr, Ca) BPO ₅ : Eu, Mn, (Sr, Ca ) 10 (PO 4) 6 · nB 2 O 3: Eu, 2 _{rO · 0.84P 2 O 5 · 0.16B} 2 O 3: Eu, Sr 2 Si 3 O 8 · 2SrCl 2: Eu, BaAl 8 O 13: It is also possible to use Eu or the like.
In addition, said red fluorescent substance, green fluorescent substance, and blue fluorescent substance may be used individually by 1 type, and may use 2 or more types together by arbitrary combinations and ratios.

As the blue phosphor, a blue organic phosphor or a blue inorganic phosphor may be used. Therefore, the blue phosphor can be appropriately selected depending on the type of red phosphor, green phosphor, and the like. However, when the organic phosphor is used as the red phosphor and the green phosphor, it is preferable to use the organic phosphor as the blue phosphor. In this case, as the blue organic phosphor, for example, an organic phosphor such as naphthalic acid imide-based, benzoxazole-based, styryl-based, coumarin-based, pyralizone-based, triazole-based fluorescent dye, thulium complex, or the like can be used. Among these, in particular, 1,4-bis (2-methylstyryl) benzene represented by the following formula can be preferably used.

Moreover, although there is no restriction | limiting in the luminous efficiency of blue organic fluorescent substance, it is desirable to use a thing with high luminous efficiency. Specifically, it is desirable to use a phosphor having a luminous efficiency of usually 20% or more, preferably 30% or more, more preferably 45% or more. By using a blue phosphor with high luminous efficiency in this way, the amount of phosphor used can be reduced, and a light emitting device with high luminance can be manufactured even when the power of the light source is small.
In addition, a blue fluorescent substance may be used individually by 1 type, and may use 2 or more types together by arbitrary combinations and a ratio.

[2-4. Usage ratio of phosphor]
When two or more phosphors are used as the phosphor, the usage ratio of the phosphors to be used can be arbitrarily set according to the light emitted from the light emitting device. Therefore, when a green phosphor, a red phosphor and a blue phosphor are used as the phosphor, the mixing ratio of the green phosphor, the red phosphor and the blue phosphor is such that the light emitted from the light emitting device has a desired emission color (for example, White and light bulb color) may be selected as appropriate. Usually, it can be made into the range of green fluorescent substance: red fluorescent substance: blue fluorescent substance = 1-99: 1-99: 1-99 by weight ratio.

By the way, in the present invention, the above-described Eu (TTA) ₃ (TPPO) ₂ , Eu (TTA) ₃ Phen, Eu (TTA) ₃ IQNO, Eu (2MTTA) ₃ Phen, Eu (2NFA) are used as the red organic phosphor. ₃ Phen, Eu (DBM) ₃ Phen, Eu (DBM) ₃ TPPO, Eu (2NFA) ₃ (TPPO) ₂ , Eu (2NFA) ₃ DPPhen, Eu (HFA) ₃ (TPPO) ₂ etc., and green As the organic color phosphor, it is preferable to use a green organic phosphor represented by the above general formula (1) (hereinafter referred to as “green organic phosphor (1)” as appropriate). This is because a light-emitting device with high luminance and good color rendering can be manufactured.

  In this case, the ratio of the green organic phosphor (1) contained in the total amount of the phosphor (weight of the green organic phosphor (1) / total weight of the phosphor) is usually 0.01 or more, preferably 0.1. As mentioned above, it is desirable to set it as 0.5 or more, and usually 20 or less, preferably 15 or less, more preferably 10 or less. Thereby, it is possible to obtain an advantage that a high-luminance light-emitting device can be obtained even though the amount of green organic phosphor used is small.

  In this case, the weight ratio of the green organic phosphor (1) to the red organic phosphor (the weight of the green organic phosphor (1) / the weight of the red organic phosphor) is usually 0.01 or more, preferably It is desirable that it is 0.1 or more, more preferably 0.5 or more, and usually 20 or less, preferably 15 or less, more preferably 10 or less. Thereby, it is possible to obtain an advantage that a high-luminance light-emitting device can be obtained even though the amount of green organic phosphor used is small.

  Furthermore, in this case, the weight ratio of the green organic phosphor (1) to the blue phosphor (weight of the green organic phosphor (1) / weight of the blue phosphor) is usually 0.01 or more, preferably 0.1. As described above, it is desirable to set it to 0.5 or more, usually 40 or less, preferably 30 or less, more preferably 20 or less. Thereby, it is possible to obtain an advantage that a high-luminance light-emitting device can be obtained even though the amount of green organic phosphor used is small.

[2-5. Status of phosphor]
The phosphor used in the present invention is preferably used in a solid state since the effect of intermolecular interaction is large and a flat excitation spectrum is obtained. The solid state is a crystalline state, an amorphous state, or a solid solution state, and it is particularly preferable to use fine particles having a crystalline state with a long exciton lifetime.

  Moreover, a well-known structure can be arbitrarily applied as a use condition of fluorescent substance. Usually, there are a solid solution state in which the complex is dissolved in the binder resin, a dispersed state in which fine particles of the complex are dispersed in the binder resin, and the like. In this case, the light emitting device is fixed by a binder resin and absorbs light from the light source to emit light.

  There is no restriction | limiting in binder resin used for these, As long as the effect of this invention is not impaired remarkably, it is arbitrary. For example, a thermoplastic resin, a thermosetting resin, a photocurable resin, etc. are mentioned. Specific examples include methacrylic resins such as polymethylmethacrylate; styrene resins such as polystyrene and styrene-acrylonitrile copolymers; polycarbonate resins; polyester resins; phenoxy resins; butyral resins; polyvinyl alcohols; Cellulose-based resins such as cellulose acetate butyrate; epoxy resins; phenol resins; silicone resins.

  Further, an inorganic material such as a siloxane bond formed by solidifying a solution obtained by hydrolyzing a solution containing an inorganic material such as a metal alkoxide, a ceramic precursor polymer or a metal alkoxide by a sol-gel method, or a combination thereof. An inorganic material can be used.

  When the phosphor is dispersed in the binder resin, the amount of the phosphor used relative to the binder resin is not particularly limited. However, usually, the phosphor is usually 0.01 parts by weight or more, preferably 0.1 parts by weight or more, more preferably 1 part by weight or more, and usually 100 parts by weight or less with respect to 100 parts by weight of the binder resin. , Preferably 80 parts by weight or less, more preferably 60 parts by weight or less.

Further, the binder resin may contain additives other than the phosphor. Examples of additives include color correction dyes, antioxidants, processing / oxidation and heat stabilizers such as phosphorus-based processing stabilizers, light-resistant stabilizers such as UV absorbers, and silane coupling agents. Can be mentioned.
In addition, binder resin may be used individually by 1 type, and may use 2 or more types together by arbitrary combinations and a ratio.

  In the present embodiment, it is assumed that a green organic phosphor, a red organic phosphor, and a blue organic phosphor are used as the phosphor 3. In addition, a pyridine-phthalimide condensed derivative compound represented by the general formula (1) is used as the green organic phosphor, and a rare earth element ion complex is used as the red organic phosphor. Further, it is assumed that these phosphors 3 are used by being dispersed in a transparent binder resin capable of transmitting light having a wavelength emitted from each phosphor.

[3. Other parts]
A member other than the light source and the phosphor may be provided in the light emitting device. For example, an external cap may be provided to protect the light source and the phosphor.
In the present embodiment, it is assumed that the light emitting device 1 includes an external cap 4 for protecting the light emitting device 1.

[4. Other configurations]
In the light emitting device of the present invention, there is no restriction on the positional relationship between the light source and the phosphor, and it is arbitrary as long as the light emitting device can emit desired light. However, usually, a phosphor-containing layer containing a phosphor such as a red phosphor, a blue phosphor, or a green phosphor is disposed on the light source. In this case, the red phosphor does not necessarily have to be mixed in the same layer as the blue phosphor and the green phosphor. For example, a layer containing a red phosphor may be laminated on a layer containing a blue phosphor and a green phosphor.

Further, the phosphor-containing layer can be provided on the upper part of the light source (usually, the side from which light from the light emitting device is emitted). The phosphor-containing layer can be provided, for example, as a contact layer between the light source and the sealing resin portion, as a coating layer outside the sealing resin portion, or as a coating layer inside the outer cap. Furthermore, it is possible to take a form in which a phosphor is contained in the sealing resin.
In the present embodiment, a phosphor-containing layer in which the phosphor 3 is dispersed in a binder resin is formed on the surface of the light source 2.

  In the light emitting device of the present invention, it is preferable that a treatment for shielding ultraviolet rays of 350 nm or less is provided outside the phosphor-containing layer from the viewpoint of improving the durability of the phosphor.

[5. Physical properties of light emitting device]
The color of light emitted from the light-emitting device of the present invention is arbitrary, but normally it is preferably white light (that is, white light). This is because the light-emitting device of the present invention can be applied to various uses such as an in-vehicle light source, a display backlight, and a lighting device.

  In the light emitting device of the present invention, the light emission efficiency of the light emitting device is usually 20 lm / W or more, preferably 22 lm / W or more, more preferably 25 lm / W or more, and particularly preferably 28 lm / W or more. This can be realized by using an appropriate combination of the above-mentioned phosphors such as the pyridine-phthalimide condensed derivative compound and the rare earth element ion complex.

  Furthermore, in the light emitting device of the present invention, the average color rendering evaluation index Ra is usually 80 or more, preferably 85 or more, more preferably 88 or more. Thereby, the color of the light emitting device can be brought close to natural light, and the color of the object illuminated by the light emitting device of the present invention can be made more natural. This can also be realized by appropriately combining phosphors such as the above-mentioned pyridine-phthalimide condensed derivative compounds and rare earth element ion complexes.

[6. Action]
According to the light emitting device 1 described above, the light emitted from the light source 2 is absorbed by the phosphors 3 such as the green phosphor, the red phosphor, and the blue phosphor to emit fluorescence, and the fluorescence is emitted to the outside through the external cap 4. Thus, white light can be emitted.
At this time, the light-emitting device 1 of the present embodiment has high luminance, is closer to natural light, and has little deviation in emission color due to increase or decrease in the amount of emitted light. This is an advantage obtained mainly by using a combination of excellent phosphors.

To explain individually, the light emitting device 1 can achieve high luminance because it uses an organic phosphor, and in particular, a specific organic phosphor (green light having a peak wavelength in the range of 510 nm to 560 nm) is used. It is speculated that this is because a green organic phosphor having a luminous efficiency of 30% or more was used.
The light emitting device 1 can emit light close to natural light because an organic phosphor is used. In particular, a specific organic phosphor (β-diketonate, β-diketone, aromatic) is used as a red organic phosphor. This is presumably because a red organic phosphor comprising a rare earth element ion complex having a carboxylic acid or a Bronsted acid as a ligand is used.
Furthermore, it is assumed that the difference in emission color due to the increase or decrease in the amount of emitted light can be reduced because the specific red and / or green organic phosphors are used.

  Moreover, when the pyridine-phthalimide condensed derivative compound is used as the green organic phosphor as in the light emitting device 1 of the present embodiment, the following advantages can be obtained. That is, when a pyridine-phthalimide condensed derivative compound is used as the green organic phosphor, the green organic phosphor emits green light having a wavelength that can be easily recognized by human eyes. That is, the green light emitted from the green organic phosphor is visible to the human eye as brighter light than the light emitted from other green phosphors. Therefore, by using a pyridine-phthalimide condensed derivative compound as the green organic phosphor, it is possible for the human eye to recognize the light as brighter than the actual light emission efficiency.

[7. Application]
The light-emitting device of the present invention can be used alone or in combination, for example, as an illumination lamp, a backlight for a liquid crystal panel, various illumination devices such as ultra-thin illumination, and an image display device. it can.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further more concretely, this invention is not limited to description of a following example, unless the summary is exceeded.

[Example 1]
Under the following conditions, a dispersion liquid in which a red phosphor, a green phosphor, and a blue phosphor were dispersed in an aqueous polyvinyl alcohol solution was produced.

Red phosphor dispersion:
Eu (DBM) ₃ TPPO 100 mg and GOHSENOL GL-3 (Nippon GOHSEI Polyvinyl alcohol (10% aqueous solution)) 2.5 g were mixed, and 2 cc of zirconia beads (particle size 0.2 mm) was added. Using a paint shaker, dispersion treatment was performed for 1 hour at room temperature.

Green phosphor dispersion:
100 mg of a pyridine-phthalimide condensed derivative compound represented by the following formula and 2.5 g of GOHSENOL GL-3 (Nippon GOHSEI polyvinyl alcohol (10% aqueous solution)) are mixed, and zirconia beads (particle size 0) are mixed. .2 mm) 2 cc was added and dispersed using a paint shaker for 1 hour at room temperature.

Blue phosphor dispersion:
Bis (MSB) 100 mg and Gohsenol GL-3 (Nippon Synthetic Chemical Industry polyvinyl alcohol (10% aqueous solution)) 2.5 g were mixed, and 2 cc of zirconia beads (particle size 0.2 mm) was added. Using a paint shaker, dispersion treatment was performed for 1 hour at room temperature.

The obtained dispersion was mixed so that the weight ratio of the red phosphor, the green phosphor and the blue phosphor was red phosphor: green phosphor: blue phosphor = 42: 8: 50. A coating solution was prepared.
The obtained phosphor coating solution was air-brush sprayed so that the dry film thickness was 0.3 mm, and a bullet type LED manufactured by Cree (peak wavelength: 405 nm, diameter: 5 mm, height: 9 mm, sealed with epoxy resin) And dried in air at a temperature of 100 ° C. for 5 minutes.

  A light-emitting device 1 as shown in FIG. 1 was produced by further covering the phosphor coating film with a glass cap. Here, reference numeral 2 represents a bullet-type LED as a light source. 1 indicates a phosphor provided as a phosphor coating layer, and 4 indicates a glass cap provided as an external cap 4.

When the obtained light emitting device was turned on (driving current 20 mA), white light having a light bulb color temperature of 3445K was obtained.
Moreover, when the chromaticity coordinate of the white light emitted from a light-emitting device was measured, it became like FIG. FIG. 3 is an enlarged view of the main part of FIG. 2 and 3, the portion indicated by the arrow indicates the coordinates of white light emitted by the light emitting device of this embodiment. As shown in FIGS. 2 and 3, the obtained white light was x = 0.40553 and y = 0.3840 in the xy chromaticity diagram. The luminous efficiency of the light emitting device was 30.7 lm / W, and the average color rendering index Ra was 90. The emission intensity of the obtained white light is shown in FIG.

In addition, Table 1 shows the results obtained by comparing the obtained light emitting device with the white light emitted and a commercially available white LED (manufactured by Nichia Corporation) using a yellow inorganic phosphor. The light emitting device produced in this example has a luminous efficiency comparable to that of a commercially available light emitting device, and has a high luminance. The average color rendering index Ra is better than that of the commercially available product, and is excellent in color rendering. Was confirmed.

[Evaluation of phosphor]
The results of measuring the emission intensity of the green phosphor and the BAM green phosphor (BaMgAl ₄ O ₃ : Eu) used in Example 1 are shown in FIG. In FIG. 5, a is a BAM green phosphor, and b is a green phosphor used in this example. From this, it was confirmed that the green phosphor used in Example 1 has a peak wavelength in the range of 530 nm to 540 nm.

  Table 2 shows values obtained by measuring the luminous efficiency of the phosphors for the green phosphor, the red phosphor, and the blue phosphor. The luminous efficiency (%) of the phosphor is measured by irradiating the phosphor with light having a peak wavelength of 400 nm (exposure time 400 msec) and measuring the total reflected light amount (T1) and the light emission amount (S2) (average value of three times). And (S2 × 100) / T1. Here, as the total reflected light amount, a value obtained by dividing the actually measured total reflected light amount by the reflectance (0.987) of the standard white plate was used.

In Table 2, a is a BAM green phosphor, b is a green phosphor used in this example, c is a LOS phosphor (La ₂ O ₂ S: Eu), d is Eu (TTA) ₃ Phen, e is _{Eu (TTA) 3 (TPPO)} 2, f is BAM-based blue phosphor, g were used in this example Bis (MSB). Among these, b, d, e, and g can be particularly preferably used as the organic phosphor of the light emitting device of the present invention.

  The light-emitting device of the present invention can be used in any field where light is used, and is particularly useful as a light-emitting device for medical instruments such as a stomach camera and a capsule endoscope.

It is a figure which shows typically the structure of the light-emitting device as one Embodiment of this invention, and the light-emitting device produced in Example 1 of this invention. It is xy chromaticity diagram which shows the color coordinate of the white light which the light-emitting device produced in Example 1 of this invention emitted. It is the figure which expanded the principal part of xy chromaticity diagram of FIG. It is a figure which shows the emitted light intensity of the white light which the light-emitting device produced in Example 1 of this invention emitted. It is a figure which shows the emitted light intensity of the green fluorescent substance and BAM type | system | group green fluorescent substance which were used in Example 1 of this invention.

Explanation of symbols

1 Light Emitting Device 2 Light Source 3 Phosphor 4 External Cap

Claims (7)

A light emitting device comprising: a light source that emits light having a peak wavelength in a range of 350 nm to 420 nm; and a phosphor that emits light having a different wavelength by absorbing at least part of the light from the light source,
Including at least one organic phosphor as the phosphor,
The luminous efficiency of the light emitting device is 20 lm / W or more,
An average color rendering evaluation index Ra is 80 or more. 2. The light emitting device according to claim 1, wherein the organic phosphor is a green organic phosphor that emits light having a peak wavelength in a range of 510 nm to 560 nm and has a luminous efficiency of 30% or more. . The organic phosphor is a red organic phosphor composed of a rare earth element ion complex having β-diketonate, β-diketone, aromatic carboxylic acid, or Bronsted acid as a ligand. Or the light-emitting device of Claim 2. 4. The light emitting device according to claim 3, wherein a red organic phosphor having a luminous efficiency of 20% or more is used. The light emitting device according to claim 1, wherein the light emitting device emits white light. An illumination device comprising the light-emitting device according to claim 1. An image display device comprising the light-emitting device according to claim 1.

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