JP2018146659A - Light-emitting resin composition for wavelength conversion, wavelength conversion member, wavelength conversion unit, and light emitting element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a light-emitting resin composition for wavelength conversion that emits red light in a high quantum yield, and a wavelength conversion member, and a wavelength conversion unit and a light emitting element.SOLUTION: A light-emitting resin composition for wavelength conversion contains at least one organic light-emitting compound represented by a specific formula and nonpolar resin, where, the organic light-emitting compound is dispersed in the nonpolar resin in a solid state. There are also provided a wavelength conversion member having a wavelength conversion section composed of the light-emitting resin composition for wavelength conversion, and a wavelength conversion unit and a light emitting element having the wavelength conversion member.SELECTED DRAWING: None

Description

  The present invention relates to a wavelength-converting light-emitting resin composition, a wavelength conversion member, a wavelength conversion unit, and a light-emitting element.

Light emitting diodes (LEDs) that emit white light are widely used in display devices such as various displays. In recent years, interest in energy-related problems has increased, and lighting devices such as fluorescent lamps that use white LEDs are rapidly spreading.
The white LED is usually configured by combining an LED and a phosphor. This phosphor absorbs light of a specific wavelength (incident light) emitted from the LED and emits light of a specific wavelength (emitted light) different from this light, and a resin. It is formed from the resin composition for wavelength conversion to contain. Among wavelength conversion materials, organic wavelength conversion materials are superior to inorganic wavelength conversion materials in that they exhibit high wavelength conversion efficiency.
As a wavelength conversion resin composition using such an organic wavelength conversion material, a composition containing a dipyrromethene boron complex compound and a resin has been proposed. For example, Patent Document 1 discloses that as a wavelength converting resin composition for converting incident light into red light, the 1-position, 7-position and 8-position carbon atoms of the s-indacene skeleton are substituted with phenyl groups, and the 2-position. And a wavelength conversion resin composition (Examples 2 and 4) containing a dipyrromethene boron complex compound A-23 in which the carbon atom at the 6-position is unsubstituted and a polycarbonate. In Patent Document 2, as a wavelength converting resin composition for converting wavelength of incident light into red light, the 1-position, 7-position and 8-position carbon atoms of the s-indacene skeleton are substituted with phenyl groups. And a dipyrromethene boron complex compound R-1 to R-9 etc. in which the carbon atom at the 6-position is unsubstituted or substituted with a cyano group and the like, and a silicone resin (Examples 38 to 45) Is described.

JP 2011-241160 A International Publication No. 2016 / 190283A1

  It is important for the wavelength conversion resin composition to maintain a function of converting incident light into outgoing light having a specific wavelength (aggregation of wavelength conversion material / association emission wavelength). However, part of the organic wavelength conversion material is dissolved, compatible or eluted in the resin used together. When the wavelength conversion material is dissolved in the resin, generally, the wavelength of the emitted light wavelength-converted by the wavelength conversion resin composition becomes shorter than the target wavelength. That is, it becomes impossible to convert incident light into outgoing light having a specific wavelength.

In a light emitting device using a wavelength conversion resin composition, the quantum yield generally decreases due to aggregation-induced quenching when the wavelength conversion material is aggregated or in a solid state. Therefore, in the conventional wavelength conversion resin composition, the wavelength conversion material is dissolved in the combined resin, thereby suppressing aggregation of the wavelength conversion material and suppressing a decrease in quantum yield. However, the quantum yield which the conventional wavelength conversion resin composition shows is not enough. In particular, the resin composition for wavelength conversion that converts incident light into red light (light having a wavelength of 600 to 750 nm) has a low quantum yield. Even when the resin compositions for wavelength conversion described in Patent Documents 1 and 2 are used, the quantum yield is not sufficient.
In the present invention, the quantum yield means the ratio of the number of photons emitted as fluorescence to the number of photons absorbed by the wavelength conversion material.

As described above, in order to achieve a high quantum yield, it is important that the wavelength conversion material does not aggregate. However, it is difficult to completely dissolve the wavelength conversion material at a high concentration with respect to a resin that is generally used in combination. That is, the insoluble content of the wavelength conversion material coexists in the mixture of the wavelength conversion material and the resin. When this insoluble matter coexists, it becomes impossible to convert incident light into outgoing light having a specific wavelength. On the other hand, as described above, the wavelength conversion material is present (contained) without being dissolved in the resin in that the incident light is controlled so as to be converted only to the outgoing light having a specific wavelength. A resin composition is desired.
This invention makes it a subject to provide the luminescent resin composition for wavelength conversion and wavelength conversion member which light-emit red light with a high quantum yield. Moreover, this invention makes it a subject to provide the wavelength conversion unit and light emitting element which used the said wavelength conversion member.

  The present inventor uses an organic light emitting compound represented by a specific formula described later as a wavelength conversion material in combination with a nonpolar resin, thereby dispersing the organic light emitting compound in a solid state without dissolving it in the nonpolar resin. The present inventors have found that a wavelength-converting light-emitting resin composition can be prepared, and that red light can be emitted with a high quantum yield when the wavelength-converting light-emitting resin composition is used as a wavelength conversion member. The present invention has been further studied and completed based on these findings.

式（１）中、Ｒ^１１及びＲ^１６は、各々独立に、ハロゲン原子、アルキル基又はシリル基を示す。
Ｒ^１２及びＲ^１５は、各々独立に、下記式（Ａｒ−１）で表わされる基を示す。
Ｒ^１３及びＲ^１４は、各々独立に、水素原子、ハロゲン原子、アルキル基、アリール基、ヘテロ環基、エテニル基、エチニル基、アミノ基、シリル基、アシル基、アルコキシ基、アリールオキシ基、アルキルチオ基又はアリールチオ基を示す。
Ｒ^１７はアリール基を示す。
Ｘ^１及びＸ^２は、各々独立に、ハロゲン原子、アルキル基、アリール基、ヘテロ環基、ヒドロキシ基、アルコキシ基、アリールオキシ基、アルキルチオ基、アリールチオ基、エテニル基又はエチニル基を示す。
ただし、Ｒ^１１〜Ｒ^１７、Ｘ^１及びＸ^２のうち少なくとも１つは、極性を示す部分構造を有する。

式（Ａｒ−１）中、Ｒ^１２１及びＲ^１２２は、各々独立に、ハロゲン原子、アルキル基、アミノ基、シリル基、アルキルチオ基、アリールチオ基、エテニル基若しくはエチニル基、又は、ヒドロキシ基、シアノ基、カルボキシ基、カルボン酸無水物結合、エステル結合、カルボニル結合、−ＳＯ_３−結合、カーボネート結合、ウレタン結合、エーテル結合、ラクトン環構造及びスルトン環構造から選択される、極性を示す部分構造を示す。ｎは０〜４の整数である。＊は式（１）中のピロール環を形成する炭素原子との結合部を示す。 That is, the subject of this invention was achieved by the following means.
<1> A wavelength-converting luminescent material comprising at least one organic luminescent compound represented by the following formula (1) and a nonpolar resin, wherein the organic luminescent compound is dispersed in a solid state in the nonpolar resin. Resin composition.

In formula (1), R ¹¹ and R ¹⁶ each independently represent a halogen atom, an alkyl group or a silyl group.
R ¹² and R ¹⁵ each independently represent a group represented by the following formula (Ar-1).
R ¹³ and R ¹⁴ are each independently a hydrogen atom, halogen atom, alkyl group, aryl group, heterocyclic group, ethenyl group, ethynyl group, amino group, silyl group, acyl group, alkoxy group, aryloxy group, alkylthio group. A group or an arylthio group;
R ¹⁷ represents an aryl group.
X ¹ and X ² each independently represent a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a hydroxy group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an ethenyl group or an ethynyl group.
However, at least one of R ^{11 to} R ¹⁷ , X ¹ and X ² has a partial structure exhibiting polarity.

In formula (Ar-1), R ¹²¹ and R ¹²² each independently represent a halogen atom, an alkyl group, an amino group, a silyl group, an alkylthio group, an arylthio group, an ethenyl group or an ethynyl group, or a hydroxy group or a cyano group. , A carboxylic group, a carboxylic acid anhydride bond, an ester bond, a carbonyl bond, a —SO ₃ — bond, a carbonate bond, a urethane bond, an ether bond, a lactone ring structure, and a sultone ring structure. . n is an integer of 0-4. * A bond part with the carbon atom which forms the pyrrole ring in Formula (1) is shown.

<2> A partial structure having polarity, which at least one of R ^{11 to} R ¹⁷ , X ¹ and X ² has, is a hydroxy group, a cyano group, a carboxy group, a carboxylic acid anhydride bond, an ester bond, a carbonyl bond, − The light emitting resin composition for wavelength conversion according to <1>, which is a partial structure selected from an SO ₃ -bond, a carbonate bond, a urethane bond, an ether bond, a lactone ring structure, and a sultone ring structure.
<3> The light-emitting resin composition for wavelength conversion according to <1> or <2>, wherein the nonpolar resin is a silicone resin.
<4> The luminescent resin composition for wavelength conversion according to any one of <1> to <3>, wherein R ¹³ and R ¹⁴ each represent an alkyl group.
<5> The luminescent resin composition for wavelength conversion according to any one of <1> to <4>, wherein R ¹¹ , R ¹³ , R ^14, and R ¹⁶ are all alkyl groups.
<6> A wavelength conversion member having a wavelength conversion part made of the wavelength conversion luminescent resin composition according to any one of <1> to <5>.
<7> The wavelength conversion member according to <6>, wherein the wavelength conversion unit is a wavelength conversion layer.
<8> A wavelength conversion unit having a light source and the wavelength conversion member according to <6> or <7>.
<9> The wavelength conversion unit according to <8>, wherein the light source is a light emitting diode.
<10> The wavelength conversion unit according to <8> or <9>, which converts incident light into emitted light having a wavelength of 600 to 750 nm.
<11> A light emitting device having the wavelength conversion member according to <6> or <7>.

  When the wavelength-converting light-emitting resin composition of the present invention is used for a wavelength conversion member, it can emit red light obtained by wavelength-converting incident light with a high quantum yield. Moreover, the wavelength conversion member, wavelength conversion unit, and light emitting element of the present invention can emit red light with high quantum yield.

In the present specification, unless otherwise specified, the double bond may be either E-type or Z-type in the molecule, or a mixture thereof.
When there are a plurality of substituents, linking groups, ligands, etc. (hereinafter referred to as substituents, etc.) indicated by a specific symbol or formula, or when a plurality of substituents etc. are specified simultaneously, there is no special notice. As long as each substituent is the same, it may be the same or different. The same applies to the definition of the number of substituents and the like. Further, when a plurality of substituents and the like are adjacent (particularly adjacent), they may be connected to each other to form a ring unless otherwise specified. In addition, unless otherwise specified, a ring such as an alicyclic ring, an aromatic ring, or a heterocyclic ring may be further condensed to form a condensed ring.

  In this specification, about the display of a compound (a complex and a pigment | dye are included), it uses for the meaning containing its salt and its ion besides the compound itself. Moreover, it is the meaning including what changed a part of structure in the range which does not impair the effect of this invention. Furthermore, it is the meaning which may have arbitrary substituents in the range which does not impair the effect of this invention about the compound which does not specify substitution or unsubstituted. The same applies to substituents, linking groups and ligands.

  Moreover, the numerical range represented using "to" in this specification means the range which includes the numerical value described before and behind "to" as a lower limit and an upper limit.

[Light-emitting resin composition for wavelength conversion]
The light-emitting resin composition for wavelength conversion of the present invention contains at least one organic light-emitting compound represented by the following formula (1) and a nonpolar resin. In this wavelength converting luminescent resin composition, the organic luminescent compound is dispersed in a non-polar resin in a solid state.
In the present invention, the organic luminescent compound is dispersed in a solid state in a nonpolar resin means that the organic luminescent compound is dispersed in the nonpolar resin without being dissolved, compatible or eluted (solid dispersion). Product or solid composition). Here, the solid state includes not only an aspect in which the organic light-emitting compound is completely in a solid state but also an aspect in which a part of the organic light-emitting compound is not in a solid state within a range that does not impair the target wavelength conversion function. To do. The range that does not impair the target wavelength conversion function cannot be uniquely determined according to the characteristics or use of the organic light-emitting compound. For example, regarding the wavelength of the light converted by the wavelength converting luminescent resin composition, the wavelength is shortened by about 30 nm with respect to the target wavelength of the emitted light (aggregation / association emission wavelength of the organic luminescent compound). A range is mentioned. In addition, when the organic light emitting compound is colored, the nonpolar resin in the wavelength converting light emitting resin composition (wavelength converting member) is colored in a color different from the color exhibited by itself when visually confirmed. There is no range. Furthermore, it can also be set as the range prescribed | regulated with the evaluation method by the fluorescence spectrum in the Example mentioned later instead of the method by the said short wavelength or coloring.
In addition, in the present invention, the composition means a component concentration within a range where the above-described target wavelength conversion function is not impaired in addition to a mixture having a constant component concentration (each component is uniformly dispersed). Includes fluctuating mixtures.

<Organic Luminescent Compound Represented by Formula (1)>
The organic light-emitting compound contained in the wavelength-converting light-emitting resin composition of the present invention is represented by the following formula (1).

In the formula (1), R ¹¹ and R ¹⁶ each independently represent a halogen atom, an alkyl group or a silyl group.
The halogen atom which can be taken as R ¹¹ and R ¹⁶ has the same meaning as the halogen atom of the substituent group T described later.
Examples of the alkyl group that can be adopted as R ¹¹ and R ¹⁶ include a linear alkyl group, a branched alkyl group, and a cyclic alkyl group. A linear alkyl group or a branched alkyl group is preferable, and a linear alkyl group is preferable. Carbon number of a linear alkyl group or a branched alkyl group becomes like this. Preferably it is 1-36, More preferably, it is 1-18, More preferably, it is 1-12, Most preferably, it is 1-6. Carbon number of a cyclic alkyl group becomes like this. Preferably it is 3-20, More preferably, it is 3-12, More preferably, it is 3-8.
The silyl group that can be employed as R ¹¹ and R ¹⁶ is preferably a silyl group having 0 to 30 carbon atoms, and more preferably a silyl group having 1 to 20 carbon atoms. More preferred is a silyl group in which an alkyl group, aryl group, alkoxy group or aryloxy group is bonded to a silicon atom.

R ¹¹ and R ¹⁶ are preferably an alkyl group, more preferably a linear alkyl group or a branched alkyl group, still more preferably a linear alkyl group having 1 to 6 carbon atoms, and particularly preferably methyl.
R ¹¹ and R ¹⁶ may be the same or different and may have a substituent. The R ¹¹ and the substituent which may be R ¹⁶ optionally has, but not limited to, substituents selected from Substituent Group T described later, or include partial structures of the polar to be described later.

R ¹² and R ¹⁵ each independently represent a group represented by the following formula (Ar-1).
In the organic light emitting compound represented by the above formula (1), R ¹¹ and R ¹⁶ are the above atoms or substituents, and R ¹² and R ¹⁵ have the substituent R ¹²¹ at the 2-position of the benzene ring. The group represented by (Ar-1) exhibits a high quantum yield even when dispersed in a solid state by suppressing the intermolecular interaction of the organic light-emitting compound, as will be described later.

In the formula (Ar-1), * represents a bond part with the carbon atom forming the pyrrole ring in the above formula (1).
R ¹²¹ and R ¹²² each independently represent a halogen atom, an alkyl group, an amino group, a silyl group, an alkylthio group, an arylthio group, an ethenyl group or an ethynyl group. R ¹²¹ and R ¹²² each independently represent a partial structure exhibiting polarity described later, in addition to the halogen atom and the groups described above.
The halogen atom, alkyl group and silyl group which can be adopted as R ¹²¹ and R ^{122 have the same meanings} as the halogen atom, alkyl group and silyl group which can be adopted as R ¹¹ and R ¹⁶ , respectively.
The amino group which can be taken as R ¹²¹ and R ¹²² has the same meaning as the corresponding group in the substituent group T described later.
The alkylthio group that can be adopted as R ¹²¹ and R ¹²² is not particularly limited, but is preferably an alkylthio group having 1 to 30 carbon atoms, more preferably an alkylthio group having 1 to 20 carbon atoms, and further an alkylthio group having 1 to 12 carbon atoms. preferable. When the alkyl part of the alkylthio group is cyclic, the lower limit of the carbon number is 3.
The arylthio group that can be employed as R ¹²¹ and R ¹²² is not particularly limited, but an arylthio group having 6 to 30 carbon atoms is preferable, and an arylthio group having 6 to 26 carbon atoms is more preferable.
The partial structure showing polarity that can be adopted as R ¹²¹ and R ¹²² is synonymous with the partial structure showing polarity that can be adopted by at least one of R ^{11 to} R ¹⁷ , X ^1, and X ² described later.

R ¹²¹ and R ¹²² are each independently preferably a halogen atom, an alkyl group, an amino group, a silyl group or a partial structure showing polarity, more preferably a halogen atom, an alkyl group or a partial structure showing polarity, and further an alkyl group. preferable.

R ¹²¹ and R ¹²² may be the same or different. When n is an integer of 2 or more, the plurality of R ¹²² may be the same or different.
R ¹²¹ and R ¹²² may have a substituent. Although it does not specifically limit as a substituent which ^R121 and ^R122 may have, The substituent selected from the substituent group T mentioned later or the partial structure which shows the polarity mentioned later is mentioned.

In the formula (Ar-1), n is an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 1 or 2.
When n is an integer of 1 or more, the bonding position of R ¹²² is not particularly limited. In the formula (Ar-1), it may be any of the 3rd to 6th positions (the carbon atom to which R ¹²¹ is bonded is the 2nd position) with respect to the carbon atom marked with *. Alternatively, 6-position is preferable, and 6-position, or 4-position and 6-position are more preferable.

R ¹² and R ¹⁵ are preferably each independently a group represented by the following formula (Ar-2).
In the formula (Ar-2), * represents a bond part with the carbon atom forming the pyrrole ring in the above formula (1).
In the organic light emitting compound represented by the above formula (1), R ¹² and R ¹⁵ are represented by the following formula (Ar-2) having substituents R ²²¹ and R ²²² at the 2nd and 6th positions of the benzene ring. When the group is present, a higher quantum yield is exhibited.

In the formula (Ar-2), R ^{221 to} R ²²³ are each independently synonymous with R ¹²¹ in the formula (Ar-1). R ^{221 to} R ²²³ may be the same as or different from each other.
m is an integer of 0 to 3, and 0 or 1 is preferable.
When m is an integer of 1 or more, the bonding position of R ²²³ is not particularly limited. In the formula (Ar-2), it may be any of the 3rd to 5th positions (the carbon atom to which R ²²¹ is bonded is the 2nd position) with respect to the carbon atom marked with *, and the 4th position is preferred. .

In the formula (1), R ¹³ and R ¹⁴ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an ethenyl group, an ethynyl group, an amino group, a silyl group, an acyl group, or an alkoxy group. Represents an aryloxy group, an alkylthio group or an arylthio group.
The halogen atom, alkyl group and silyl group which can be taken as R ¹³ and R ^{14 have the same} meanings as the halogen atom, alkyl group and silyl group which can be taken as R ¹¹ and R ¹⁶ , respectively.

The aryl group that can be adopted as R ¹³ and R ¹⁴ is preferably an aryl group having 6 to 48 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and 6 to 10 Are particularly preferred. As the aryl group, a benzene ring group is preferable.
The heterocyclic group which can be adopted as R ¹³ and R ¹⁴ is preferably a 5- to 7-membered heterocyclic ring. The heterocyclic ring may be a saturated or unsaturated, aromatic or non-aromatic, monocyclic or condensed heterocyclic group. The heterocyclic group is more preferably a heterocyclic group in which the ring-constituting atoms are selected from a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom, and at least one heteroatom of any of a nitrogen atom, an oxygen atom and a sulfur atom. It is. More preferably, it is a 5- or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms.

The amino group, alkylthio group and arylthio group which can be taken as R ¹³ and R ^{14 have the same} meanings as the amino group, alkylthio group and arylthio group which can be taken as R ¹²¹ and R ¹²² , respectively.
The acyl group, alkoxy group, and aryloxy group that can be adopted as R ¹³ and R ¹⁴ are respectively synonymous with the acyl group, alkoxy group, and aryloxy group of the substituent group T described later.

R ¹³ and R ¹⁴ are groups other than hydrogen atoms, that is, halogen atoms, alkyl groups, aryl groups, heterocyclic groups, ethenyl groups, ethynyl groups, amino groups, silyl groups, acyl groups, alkoxy groups, aryloxy groups, An alkylthio group or an arylthio group is preferable, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an amino group, a silyl group, an acyl group, an alkoxy group, an aryloxy group, an alkylthio group or an arylthio group is more preferable, and an alkyl group is further preferable. Among the alkyl groups, a linear alkyl group or a branched alkyl group is preferable, an alkyl group having 1 to 6 carbon atoms is more preferable, and methyl is more preferable.
R ¹³ and R ¹⁴ may be the same or different and may have a substituent. The R ¹³ and R ¹⁴ substituents which may have, but are not limited to, substituents selected from Substituent Group T described later, or include partial structures of the polar to be described later.
R ¹³ and R ¹⁴ may be the same as or different from R ¹¹ or R ^12, and R ¹¹ , R ¹³ , R ¹⁴ and R ¹⁶ are preferably all the same, and may be an alkyl group. More preferably.

In the formula (1), R ¹⁷ represents an aryl group. The aryl group which can be taken as R ¹⁷ is synonymous with the aryl group which can be taken as R ¹³ and R ¹⁴ , and a benzene ring group is preferable.
R ¹⁷ may have a substituent. Examples of the substituent that the R ¹⁷ optionally has, but not limited to, substituents selected from Substituent Group T described later, or include partial structures of the polar to be described later. Examples of the substituent R ¹⁷ has a hydrogen atom, a halogen atom, preferably a partial structure an alkyl group or a polar, hydrogen atom, a fluorine atom, more preferably the partial structure represents an alkyl group or a polar 1 to 4 carbon atoms.

In formula (1), X ¹ and X ² are each independently a halogen atom, alkyl group, aryl group, heterocyclic group, hydroxy group, alkoxy group, aryloxy group, alkylthio group, arylthio group, ethenyl group or ethynyl. Indicates a group.
The halogen atom, alkyl group, aryl group and heterocyclic group which can be taken as X ¹ and X ^{2 have the same} meaning as the halogen atom, alkyl group, aryl group and heterocyclic group which can be taken as R ¹³ and R ¹⁴ .
The alkoxy group, aryloxy group, alkylthio group and arylthio group which can be taken as X ¹ and X ^{2 have the same} meaning as the alkoxy group, aryloxy group, alkylthio group and arylthio group which can be taken as R ¹³ and R ¹⁴ .

X ¹ and X ² are preferably a halogen atom, an alkoxy group or an aryl group, more preferably a halogen atom or an alkoxy group, still more preferably a halogen atom, and particularly preferably a fluorine atom.

X ¹ and X ² may be the same or different and are preferably the same.
X ¹ and X ² may have a substituent. X ¹ and X ² are the substituents which may have, but are not limited to, substituents selected from Substituent Group T described later, or include partial structures of the polar to be described later.
X ¹ and X ² may be connected to each other to form a ring.

In the organic light-emitting compound represented by the above formula (1), at least one of R ^{11 to} R ¹⁷ , X ¹ and X ² has a polar partial structure (polar partial structure). In the present invention, the R ¹¹ is a polar moiety, may not include aspects R ¹¹ is meant embodiments having polar partial structures in a part of the structure, the overall R ¹¹ corresponds to the polarity substructure preferable. The same applies to R ^{12 to} R ¹⁷ , X ¹ and X ² . Thus, in the organic light-emitting compound represented by the above formula (1), each of the above groups that can be adopted as R ^{11 to} R ¹⁷ , X ^1, or X ² has a polar partial structure as a substituent. preferable. When at least one of R ^{11 to} R ¹⁷ , X ¹ and X ² has a polar partial structure, as described later, the dissolution of the organic light-emitting compound represented by the formula (1) in the nonpolar resin is suppressed. While exhibiting high quantum yield.

The total number of polar partial structures possessed by R ^{11 to} R ¹⁷ , X ¹ and X ² is not particularly limited as long as it is at least one, but is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 or 2 preferable.
The group having a polar partial structure may be any of R ^{11 to} R ¹⁷ , X ¹ and X ² , preferably at least one of R ¹² , R ¹⁵ , R ¹⁷ , X ¹ and X ² , and R ¹⁷ , X ¹ and At least one of X ² is more preferred, and R ¹⁷ is still more preferred.

When R ^{11 to} R ¹⁷ , X ¹ and X ² have a polar partial structure, the position at which the polar partial structure is bonded is not particularly limited. R ¹¹ to R ^17, any of the atoms ^{to which X 1} and ^{X 2} forming each group taking respectively ^{(hereinafter,} also referred to as ^{R 11,} etc.) to as long as the polar moiety is attached.
For example, when R ¹⁷ has a polar partial structure, it is preferable that this polar partial structure is bonded to the 2-6 position relative to the bond with the methine carbon atom that bonds the pyrrole ring in formula (1). When R ¹⁷ is a benzene ring, the bonding position of the polar partial structure is preferably the 2-position or the 4-position with respect to the bonding portion with the methine carbon atom, and the 4-position is preferred.

The polar partial structure is not particularly limited as long as it exhibits polarity. The polar partial structure is an atom that forms a partial structure and has a partial structure that has a large difference in electronegativity between two atoms bonded to each other. Specific examples of the polar partial structure include a hydroxy group, a cyano group, a carboxy group, a carboxylic anhydride bond, an ester bond, a carbonyl bond, a —SO ₃ — bond, a carbonate bond, a urethane bond, an ether bond, and a lactone ring structure. And a partial structure selected from sultone ring structures. Among them, preferably indicates an electron-withdrawing, a carboxy group, an ester bond, a carbonyl bond, -SO 3 _- bond, a carbonate bond, a urethane bond is preferred, a carboxyl group or an ester bond.
Among the above partial structures, those expressed as groups form a monovalent group (polar group) by themselves. On the other hand, among the above partial structures, those represented as a bond form a monovalent group (polar group) by combining with a substituent that is not particularly limited, for example, a substituent selected from the substituent group T described later. Moreover, the polar partial structure may have one or two or more of the above bonds.

The carboxylic acid anhydride bond is not particularly limited as long as it is a —CO—O—CO— bond in which the carbonyl carbon becomes a bond with R ¹¹ or the like. Although it does not specifically limit as a polar partial structure (polar group) which has a carboxylic acid anhydride bond, Preferably -C (= O) -OC (= O) -R group is mentioned. Here, although R is not specifically limited, the substituent chosen from the substituent group T mentioned later is mentioned. Among them, the substituent which can be taken as R is preferably an alkyl group (including a cycloalkyl group), an aryl group or a heterocyclic group, and more preferably an alkyl group.
The ester bond is not particularly limited as long as it is a —CO—O— bond in which the carbonyl carbon becomes a bond with R ¹¹ or the like. Although it does not specifically limit as a polar partial structure (polar group) which has an ester bond, Preferably a -C (= O) -OR group is mentioned. R is as described above.

The carbonyl bond is not particularly limited. Although it does not specifically limit as a polar partial structure which has a carbonyl bond, Preferably a -C (= O) -R group is mentioned. R is as described above.
The —SO ₃ — bond is not particularly limited as long as it is a bond in which a sulfur atom becomes a bond with R ¹¹ or the like. The polar partial structure having a —SO ₃ — bond is not particularly limited, but preferably includes a —SO ₃ R group. R is as described above.
The carbonate bond is not particularly limited as long as it is a * —O—C (═O) —O— bond and an oxygen atom marked with * is a bond with R ¹¹ or the like. Although it does not specifically limit as a polar partial structure which has a carbonate bond, Preferably -OC (= O) -O-R group is mentioned. R is as described above.
The urethane bond is not particularly limited as long as it is a * —N (R ^N ) —C (═O) —O— bond, and the oxygen atom marked with * is a bond with R ¹¹ or the like. Although it does not specifically limit as a polar partial structure which has a urethane bond, Preferably -N ( ^RN ) -C (= O) -O-R group is mentioned. ^RN has the same meaning as R above. R is as described above.

  The ether bond is not particularly limited as long as it is an -O- bond (including a cyclic ether bond). Although it does not specifically limit as a polar partial structure which has -O- coupling | bonding, Preferably -O-R group (R is as above-mentioned) is mentioned. Moreover, as a polar partial structure which has a cyclic ether bond, although it does not specifically limit, the structure which consists of various cyclic ether compounds is mentioned, A 5-7 membered ring is preferable. One or more cyclic ether bonds may be contained in the polar partial structure. Examples of such a polar partial structure include a mono- or dioxolane ring structure. The position of the ether bond is not particularly limited, and examples thereof include a 1,3-dioxolane ring and a 1,4-dioxolane ring. The dioxolane ring may have a ring carbon atom replaced with a carbonyl carbon. Examples of such a ring include a 1,3-dioxolan-2-one ring.

The lactone ring structure is not particularly limited as long as it is a structure composed of a cyclic ester, and examples thereof include α-lactone, β-lactone, γ-lactone, and δ-lactone. In the lactone ring structure, it is preferable that the ring-constituting carbon atom (excluding the carbonyl carbon) is a bonding part with R ¹¹ or the like.
The sultone ring structure is not particularly limited as long as it is a structure composed of a cyclic sulfonic acid ester of hydroxysulfonic acid. The sultone ring is preferably a 4- to 7-membered ring, more preferably a 4-membered sultone ring (1,3-propane sultone) or a 7-membered sultone ring.

In the organic light emitting compound represented by the formula (1), adjacent groups may be bonded to each other to form a ring. In the present invention, it is preferable that R ¹¹ and R ¹² , and R ¹⁵ and R ¹⁶ each do not form a ring.

  In the present invention, the organic light-emitting compound represented by the formula (1) is any of these isomers when an isomer such as an optical isomer, a geometric isomer, a bond isomer, or an ionized isomer exists. It may be a mixture of these isomers.

  The organic light emitting compound represented by the formula (1) has a peak wavelength in a wavelength region of 600 to 750 nm. This organic light-emitting compound can emit light by converting the wavelength of incident light, which will be described later, into red light in the above wavelength region.

  The organic light emitting compound represented by the above formula (1) can be synthesized by, for example, Patent Documents 1 and 2, publicly known methods, synthesis examples in Examples, or methods according thereto.

-Substituent group T-
In the present invention, preferred substituents include substituents selected from the following substituent group T.
Further, in the present specification, when only described as a substituent, this substituent group T is referred to. When each group, for example, an alkyl group, is only described, Preferred ranges for the corresponding groups of this substituent group T apply.
Furthermore, in the present specification, when an alkyl group is described separately from a cyclic (cyclo) alkyl group, the alkyl group is used in a sense including a linear alkyl group and a branched alkyl group. On the other hand, when the alkyl group is not described separately from the cyclic alkyl group (when simply described as an alkyl group), and unless otherwise specified, the alkyl group is a linear alkyl group or a branched alkyl group. And cycloalkyl group. The same applies to a compound containing a group (an alkoxy group, an alkylthio group, an alkenyloxy group, etc.) containing a group that can take a cyclic structure (an alkyl group, an alkenyl group, an alkynyl group, etc.) or a group containing a group that can take a cyclic structure. is there. When the group can form a cyclic skeleton, the lower limit of the number of atoms of the group forming the cyclic skeleton is 3 or more regardless of the lower limit of the number of atoms specifically described below for the group that can take this structure, 5 or more is preferable.
In the following description of the substituent group T, for example, in order to clarify a linear or branched group and a cyclic group, such as an alkyl group and a cycloalkyl group, they are described separately. There is also.

Examples of the group included in the substituent group T include the following groups.
An alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12, more preferably 1 to 6), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12), an alkynyl group (preferably 2-20 carbon atoms, more preferably 2-12 carbon atoms, cycloalkyl groups (preferably 3-20 carbon atoms), cycloalkenyl groups (preferably 5-20 carbon atoms), aryl groups (preferably 6-26 carbon atoms). , More preferably 6 to 10), a heterocyclic group (having at least one oxygen atom, sulfur atom or nitrogen atom as a ring-constituting atom, preferably 2 to 20 carbon atoms. A heterocyclic group is more preferred, which includes an aromatic heterocyclic group (heteroaryl group) and an aliphatic heterocyclic group), an alkoxy group (preferably having 1 to 20 carbon atoms, and more preferred). 1 to 12), an alkenyloxy group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12), an alkynyloxy group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12), cycloalkyloxy A group (preferably having 3 to 20 carbon atoms), an aryloxy group (preferably having 6 to 26 carbon atoms, more preferably 6 to 14), a heterocyclic oxy group (preferably having 2 to 20 carbon atoms),

An alkoxycarbonyl group (preferably having 2 to 20 carbon atoms), a cycloalkoxycarbonyl group (preferably having 4 to 20 carbon atoms), an aryloxycarbonyl group (preferably having 6 to 20 carbon atoms), an amino group (preferably having 0 to 0 carbon atoms). 20, (mono- or di-) alkylamino group, (mono- or di-) alkenylamino group, (mono- or di-) alkynylamino group, (mono- or di-) cycloalkylamino group, (mono -Or di-) cycloalkenylamino group, (mono- or di-) arylamino group, (mono- or di-) heterocyclic amino group), sulfamoyl group (preferably having 0 to 20 carbon atoms, alkyl , A cycloalkyl or aryl sulfamoyl group is preferred), an acyl group (preferably having a carbon number of 1-20, more preferably 2-15), Acyloxy group (preferably having 1 to 20 carbon atoms), a carbamoyl group (preferably with 1 to 20 carbon atoms, alkyl, a carbamoyl group of the cycloalkyl or aryl preferable.),

An acylamino group (preferably having 1 to 20 carbon atoms), a sulfonamide group (preferably an alkyl, cycloalkyl or aryl sulfonamide group having 0 to 20 carbon atoms), an alkylthio group (preferably having 1 to 20 carbon atoms). , More preferably 1 to 12), a cycloalkylthio group (preferably 3 to 20 carbon atoms), an arylthio group (preferably 6 to 26 carbon atoms), a heterocyclic thio group (preferably 2 to 20 carbon atoms), alkyl, A cycloalkyl or arylsulfonyl group (preferably having 1 to 20 carbon atoms),

A silyl group (preferably a silyl group having 1 to 20 carbon atoms and substituted with alkyl, aryl, alkoxy and aryloxy), a silyloxy group (preferably having 1 to 20 carbon atoms, alkyl, aryl, alkoxy and aryloxy) Is preferably a silyloxy group substituted with), a hydroxy group, a cyano group, a nitro group, a halogen atom (eg, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom), a carboxy group (—COOH), a phosphonyl group (—PO (OH ₂ ), phosphoryl group (—O—PO (OH) ₂ ), sulfo group (—SO ₃ H), boric acid group, hydroxy group, or mercapto group.

  The substituent selected from the substituent group T is more preferably an alkyl group, alkenyl group, cycloalkyl group, aryl group, heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, alkoxycarbonyl group, cycloalkoxycarbonyl. Group, amino group, acylamino group, cyano group or halogen atom, particularly preferably an alkyl group, alkenyl group, aryl group, heterocyclic group, alkoxy group, alkoxycarbonyl group, amino group, acylamino group or cyano group. .

  Unless otherwise specified, the substituent selected from the substituent group T includes a group formed by combining a plurality of the above groups. For example, when a compound or a substituent includes an alkyl group, an alkenyl group, etc., these may be substituted or unsubstituted. In addition, when an aryl group, a heterocyclic group, and the like are included, they may be monocyclic or condensed, and may be substituted or unsubstituted.

Although the specific example of the organic luminescent compound represented by Formula (1) is shown below, this invention is not limited to these organic luminescent compounds. In the following specific examples, Me represents methyl, Et represents ethyl, and ⁱ Pr represents isopropyl.

The organic light-emitting compound contained in the wavelength-converting light-emitting resin composition of the present invention may be one type or two or more types.
The content of the organic light-emitting compound in the wavelength-converting light-emitting resin composition of the present invention is not particularly limited, and is appropriately determined according to the molar extinction coefficient of the compound, the required quantum yield or absorption intensity, and the like. Is done. For example, the content is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 40 parts by mass, still more preferably 1 to 30 parts by mass with respect to 100 parts by mass of the nonpolar resin described later. ˜20 parts by mass is particularly preferred. In addition, when the luminescent resin composition for wavelength conversion of this invention contains 2 or more types of the said organic luminescent compounds, the said content shall be the total content of each organic luminescent compound.

<Non-polar resin>
The wavelength conversion light-emitting resin composition of the present invention contains a nonpolar resin.
In the present invention, the nonpolar resin includes a low polarity resin in addition to a nonpolar resin having a dipole moment of zero. The nonpolarity and low polarity of the resin are determined in relation to the organic light-emitting compound represented by the above formula (1), particularly the partial structure having the above-mentioned polarity. For example, the nonpolar resin may be one in which the organic light emitting compound represented by the above formula (1) is dispersed in a solid state. Such a nonpolar resin is not particularly limited, and examples thereof include a thermoplastic resin, a thermosetting or photocurable resin, and a resin mixture thereof.
In the present invention, the “nonpolar resin” refers to a nonpolar resin monomer, a nonpolar resin, in addition to the nonpolar resin, when the nonpolar resin is a thermosetting or photocurable resin. The compound (pre-polymerization precursor) which forms the structural component of is included.

  Examples of the nonpolar resin include polyvinyl chloride, polystyrene, fluorinated resin, silicone resin, epoxy silicone resin, silicone elastomer, cyclic olefin copolymer, aliphatic polyolefin resin (for example, polyethylene, polypropylene), or aromatic polyolefin resin. It is done.

Among these, a silicone resin, a silicone elastomer or an aliphatic polyolefin resin is preferable, and a silicone resin or polypropylene is more preferable.
Although it does not specifically limit as a silicone resin, A methyl silicone resin, a dimethyl silicone resin, a methylphenyl silicone resin, a diphenyl silicone resin, etc. are mentioned. Further, the silicone resin may be an addition reaction curable type (thermosetting).

Although the mass average molecular weight of nonpolar resin is not specifically limited, For example, it is good that it is 1,000-100,000.
The nonpolar resin is preferably transparent or translucent (the transmittance of visible light (wavelength 300 to 830 nm) is 50% or more).

  The nonpolar resin contained in the light-emitting resin composition for wavelength conversion of the present invention may be one type or two or more types.

<Additives>
The luminescent resin composition for wavelength conversion of the present invention may contain various additives usually used for luminescent resin compositions for wavelength conversion. Examples of such additives include color tone correction pigments, processing, oxidation and heat stabilizers (antioxidants, phosphorus-based processing stabilizers, etc.), light resistance stabilizers (ultraviolet absorbers, etc.), Silane coupling agents, organic acids, matting agents, radical scavengers, deterioration inhibitors, fillers (eg, silica, glass fiber, glass beads), plasticizers, lubricants, flame retardants (eg, organic halogen compounds) Flame retardant aids, antistatic agents, charge imparting agents, impact resistance improvers, anti-discoloring agents, mold release agents (for example, higher fatty acid esters of mono- or polyhydric alcohols), fluidity improvers, Examples include reactive or non-reactive diluents.

  Specific examples of the various additives include those described in Patent Documents 1 and 2, and these descriptions are preferably incorporated in the present specification. Moreover, content of an additive is not specifically limited, In the range which does not impair the objective of this invention, it determines suitably.

In the light-emitting resin composition for wavelength conversion of the present invention, the organic light-emitting compound represented by the above formula (1) is dispersed in a solid state in the nonpolar resin.
The form of the light-emitting resin composition for wavelength conversion of the present invention is not particularly limited as long as the organic light-emitting compound is in a predetermined dispersion state. For example, the form which contains nonpolar resin and the said organic luminescent compound in a particulate form is mentioned. As another form, the nonpolar resin forms a continuous phase, and the form in which the organic light-emitting compound is dispersed in a solid state. In any form, the wavelength-converting light-emitting resin composition of the present invention can be used as a material for a wavelength conversion member to be described later. In the case where the nonpolar resin forms a continuous phase, the wavelength converting luminescent resin composition is not specified in shape, but is also referred to as a wavelength converting member to be described later.

When the nonpolar resin is a solid, the wavelength-converting light-emitting resin composition of the present invention is a solid dispersion in which a solid organic light-emitting compound is dispersed in a solid nonpolar resin. On the other hand, when the nonpolar resin is liquid or liquid, the wavelength-converting light-emitting resin composition of the present invention includes a liquid composition (suspension) in which a solid organic light-emitting compound is dispersed in a liquid nonpolar resin. Become.
The wavelength-converting light-emitting resin composition of the present invention may contain the diluent (water or solvent, etc.) as long as the organic light-emitting compound is dispersed in the nonpolar resin in a solid state.

The wavelength conversion light-emitting resin composition of the present invention can emit light by converting incident light into red light with a high quantum yield. The quantum yield of the light-emitting resin composition for wavelength conversion of the present invention is the same as the quantum yield of the wavelength conversion member of the present invention.
Although the details of the reason why the light-emitting resin composition for wavelength conversion of the present invention emits red light with a high quantum yield is not yet clear, it is considered as follows.
Below, the action mechanism of each substituent in the organic luminescent compound represented by Formula (1) or a combination thereof will be specifically described. However, these do not perform their function by themselves, but are introduced into the dipyrromethene complex skeleton represented by the formula (1) to form an organic light-emitting compound having a specific chemical structure represented by the formula (1). Form. Thereby, the above-mentioned excellent characteristics are exhibited.
When the organic light-emitting compound having a partial structure exhibiting the above polarity is used in combination with the non-polar resin for the wavelength-converting light-emitting resin composition of the present invention, the affinity of the organic light-emitting compound for the non-polar resin ( (Solubility) can be reduced, and it is considered that dissolution, compatibility or elution in a nonpolar resin can be prevented.
The organic light-emitting compound represented by the formula (1) has a non-aromatic substituent or halogen atom at the 1-position (R ¹¹ ) and the 7-position (R ¹⁶ ) of the s-indacene skeleton, and It has an aryl group at the 8-position (R ⁷ ). It is considered that the organic light-emitting compound of the present invention having a specific substituent in such a specific combination cannot take a planar structure and the interaction between molecules is weakened.
The organic light-emitting compound can be dispersed in a solid state in a nonpolar resin by the partial structure showing the polarity and the combination of the specific substituents, and the wavelength can be reduced when incident light is converted. The emitted light (red light) having the target wavelength can be emitted. Moreover, it is considered that the organic light-emitting compound can suppress aggregation-induced quenching even in a solid state and exhibits a high quantum yield.

<Preparation method of luminescent resin composition for wavelength conversion>
The method for producing the wavelength conversion luminescent resin composition of the present invention is not particularly limited, and examples thereof include the following (Method A) and (Method B).

(Method A) A method comprising a step of melt-mixing a composition containing at least one organic luminescent compound represented by formula (1) and a nonpolar resin. For example, a nonpolar resin represented by formula (1) And a method of melt-mixing the organic light-emitting compound as needed. Here, the dispersion of the organic light-emitting compound in the nonpolar resin is synonymous with the above-described “the organic light-emitting compound is dispersed in a solid state in the nonpolar resin” (hereinafter, (Method B)). The same applies to.)
Examples of the method for dispersing the organic light-emitting compound represented by the formula (1) in the nonpolar resin include a melt blending method and a mixing method with a nonpolar resin powder.
The melt blending method can be performed by a conventional method. As an apparatus to be used, an apparatus used for melt-blending ordinary rubber or plastic can be used. The melting temperature is preferably set to a temperature at which the nonpolar resin can be melted and below the temperature at which the nonpolar resin begins to thermally decompose, and the temperature is usually 150 ° C. to 450 ° C., preferably 180 ° C. to 400 ° C.

(Method B) A method of curing a composition containing at least one organic light-emitting compound represented by formula (1) and a nonpolar resin monomer and / or a nonpolar resin polymerization precursor. After dispersing the organic light-emitting compound represented by the formula (1) in a thermosetting or photocurable resin monomer and / or a polymerization precursor of a nonpolar resin, the monomer and / or polymerization is performed. A method of polymerizing the precursor is mentioned. Moreover, after suspending the organic luminescent compound represented by Formula (1) in the solution of the said monomer and / or a polymerization precursor, the method of superposing | polymerizing a monomer and / or a polymerization precursor is also mentioned. . Here, suspending the organic light-emitting compound in the solution is synonymous with the above-mentioned “the organic light-emitting compound is dispersed in a solid state in the nonpolar resin”.

  When using the above monomer and / or polymerization precursor as a nonpolar resin, the following method can be used to disperse or suspend the organic light-emitting compound represented by formula (1) in the monomer and / or polymerization precursor. A method is mentioned. When the monomer and / or polymerization precursor is liquid, for example, using a paint shaker, a mixer, or a homogenizer, the organic light emission represented by the formula (1) in the liquid of the monomer and / or polymerization precursor is used. And a method of dispersing or suspending the active compound. When the monomer and / or polymerization precursor is solid, for example, using a ball mill, a sand mill, or the like, the organic light emission represented by the formula (1) on the monomer and / or polymerization precursor powder. And a method of dispersing or suspending the active compound.

The polymerization method in (Method B) is not particularly limited, and may be thermal polymerization or photopolymerization.
Thermal polymerization can be performed by a conventional method. As a thermal polymerization method, for example, there is a method in which a catalyst is added to a mixture of a thermosetting resin monomer and / or polymerization precursor and an organic light emitting compound represented by the formula (1) as necessary, and the mixture is heated. Can be mentioned. Examples of the thermal polymerization method and its conditions, as well as the catalyst used and the amount used thereof, include the method described in Patent Document 1, and the description of Patent Document 1 is preferably incorporated herein.

  Photopolymerization can be performed by a conventional method. As the photopolymerization method, for example, a photopolymerization initiator is added to the mixture of the monomer and / or polymerization precursor of the photocurable resin and the organic light-emitting compound represented by the formula (1) as necessary, Next, there is a method of irradiating with light. Examples of the photopolymerization method and the conditions thereof, as well as the polymerization initiator used and the amount used thereof, include the method described in Patent Document 1, and the description of Patent Document 1 is preferably incorporated herein.

  When the nonpolar resin is a silicone resin, a method of polymerizing by addition curing reaction is preferable. The addition curing reaction of silicone resin can also be performed by a conventional method. For example, the polymerization is preferably performed by a hydrosilylation reaction between an organosiloxane having a polymerizable reactive group (for example, an alkenyl group) and a hydrogensiloxane having a hydrogen atom bonded to a silicon atom. The conditions for the hydrosilylation reaction are not particularly limited, and examples include conditions of heating to room temperature or higher, for example, 50 to 200 ° C. in the presence of an addition reaction catalyst (for example, platinum) if desired.

The organic solvent used in the above (Method B) is not particularly limited, and examples thereof include hydrocarbon solvents, ketone solvents, halogenated hydrocarbon solvents, ester solvents, alcohol solvents, ether solvents, N, N-dimethylformamide, N, Examples include polar solvents such as N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethylimidazolidinone, and dimethyl sulfoxide.
The organic solvent may be used alone or in combination.

  Examples of the method for removing the organic solvent include a method in which the mixed organic solvent solution is heated to a temperature not lower than the boiling point of the organic solvent and not higher than the decomposition temperature of the nonpolar resin and the organic light emitting compound represented by the formula (1). At this time, it can also be removed under reduced pressure (less than atmospheric pressure).

[Wavelength conversion member]
If the wavelength conversion member of this invention has a wavelength conversion part which consists of the luminescent resin composition for wavelength conversion of this invention, the shape, a dimension, etc. will not be specifically limited, It sets suitably according to a use etc. Is done. For example, the shape of the wavelength conversion member and the wavelength conversion part of the present invention includes a film shape, a plate shape (for example, a sheet shape, a filter shape, a disk shape), a lens shape, a fiber shape, and an optical waveguide shape, respectively. .
The wavelength conversion member of the present invention is one preferred embodiment that is plate-shaped. In this case, the wavelength conversion member (also referred to as a wavelength conversion filter) of the present invention only has to have a wavelength conversion layer made of the light-emitting resin composition for wavelength conversion of the present invention as a wavelength conversion part, and is laminated with a substrate. It may be a body. Although the thickness of a wavelength conversion layer is not specifically limited, For example, 10-3000 micrometers is preferable and 30-2000 micrometers is more preferable.

  Examples of the substrate include a glass substrate or a polymer substrate. Examples of the glass substrate include soda-lime glass, barium-strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium-borosilicate glass, and quartz glass substrates. Examples of the polymer substrate include substrates made of polymers such as polycarbonate, acrylic resin, polyethylene terephthalate, polyether sulfide, and polysulfone.

  The wavelength conversion member of the present invention may have a constituent member other than the substrate. Such a constituent member is not particularly limited as long as it is usually used for a wavelength conversion member, and examples thereof include a protective film (film).

The wavelength conversion member of the present invention can emit light by converting incident light into red light with a high quantum yield. Therefore, the wavelength conversion member of this invention can be used suitably for the wavelength conversion unit or light emitting element mentioned later.
The quantum yield of the wavelength conversion member of the present invention is preferably 0.2 or more, more preferably 0.25 or more, and further preferably 0.3 or more. The upper limit of the quantum yield is not particularly limited, but is generally 1.0 or less. In the present invention, the quantum yield can be measured using a commercially available quantum yield measuring apparatus, for example, an absolute PL (photoluminescence) quantum yield measuring apparatus: C9920-02 (manufactured by Hamamatsu Photonics). Can be measured using.

The wavelength conversion member of the present invention is produced by molding the wavelength conversion light-emitting resin composition of the present invention into a predetermined shape.
The molding method is not particularly limited, and a molding method performed in a hot-melt state such as injection molding, the wavelength-converting light-emitting resin composition of the present invention is melted (the organic light-emitting compound is in a solid state in a nonpolar resin) After) spin coating method, roll coating method, bar coating method, Langmuir-Blodgett method, casting method, dipping method, screen printing method, bubble jet (registered trademark) method, ink jet method, vapor deposition method And a film forming method such as an electric field method.
Further, when the nonpolar resin is a thermosetting or photocurable resin, a composition in which a monomer and / or a polymerization precursor of the nonpolar resin and an organic light emitting compound represented by the formula (1) are mixed. It is also possible to apply the above-mentioned method in which a mold is filled, or a film is formed by the above-described film-forming method and polymerized by light or heat.

[Wavelength conversion unit]
The wavelength conversion unit of this invention has a light source and the wavelength conversion member of this invention mentioned above.
As a structure of the wavelength conversion unit of the present invention, a conventionally known structure can be applied without particular limitation. The arrangement of the light source and the wavelength conversion member is not particularly limited, and the light source and the wavelength conversion member may be arranged in contact with each other, or are arranged in a separated state or in a state of interposing another member. Also good.

The light source is not particularly limited. For example, an incandescent lamp, a metal halide lamp, an HID lamp (High Intensity Discharge Lamp), a xenon lamp, a sodium lamp, a mercury lamp, a fluorescent lamp, a cold cathode tube, cathodoluminescence, Slow electron beam tube, light emitting diode [eg, GaP (red, green), GaP _x As _(1-x) (red, orange, yellow: 0 <x <1), Al _x Ga _(1-x) As (red : 0 <x <1), GaAs (red), SiC (blue), GaN (blue), ZnS, ZnSe], electroluminescence (for example, inorganic EL or organic EL using a ZnS matrix and a luminescent center), laser ( For example, the He-Ne laser, CO ₂ laser, Ar, Kr, He-Cd laser, an excimer Za, a gas laser of the nitrogen laser, a ruby laser, yttrium - aluminum - garnet (YAG) laser, solid state laser glass laser, dye laser, semiconductor laser), can be exemplified sunlight.
The light source is preferably a light emitting diode, electroluminescence or semiconductor laser, and more preferably a light emitting diode.

As the light emitting diode, a semiconductor light emitting element having a light emitting layer capable of emitting a light emission wavelength capable of exciting the organic light emitting compound represented by the formula (1) is preferable. Examples of such a semiconductor light emitting element include those having the above semiconductor. As a semiconductor other than the above-described semiconductor, a nitride semiconductor (In _x Al _y Ga _(1-xy) , which can emit light with a short wavelength capable of efficiently exciting the organic light-emitting compound represented by the formula (1 ₎ , 0 ≦ X, 0 ≦ Y, X + Y ≦ 1) are preferred. Examples of the semiconductor structure include a homostructure, a heterostructure, or a double heterostructure having a MIS (Metal-Insulator-Silicon) junction, a PIN junction, a pn junction, and the like. Various emission wavelengths can be selected depending on the material of the semiconductor layer or the mixed crystal degree thereof. Moreover, it can also be set as the single quantum well structure or the multiple quantum well structure which formed the semiconductor active layer in the thin film which produces a quantum effect.

  In the case where white light is emitted from the light emitting device of the present invention, which will be described later, in consideration of the complementary color relationship with the emission wavelength from the organic light emitting compound represented by the formula (1) or the deterioration of the nonpolar resin, The emission wavelength (excitation wavelength) is preferably 200 to 550 nm. In order to further improve the excitation and emission efficiency of the light source and the organic light emitting compound represented by the formula (1), the emission wavelength is more preferably 300 to 500 nm. The light emitting diode is usually placed on a substrate having a patterned metal such as copper foil. Here, examples of the substrate material include insulating organic compounds or inorganic compounds (for example, glass and ceramics). As the organic compound, various polymer materials (for example, epoxy resin, acrylic resin) can be used. The shape of the substrate is not particularly limited, and various shapes such as a plate shape, a cup shape, and a porous plate shape can be selected.

Although the said semiconductor laser is not specifically limited, The thing by the following mechanisms is preferable. That is, a semiconductor is pn-junctioned, a forward bias is applied thereto, minority carriers at a high energy level are injected, and electrons flowing into the p-type region are introduced into positive holes and electrons flowing into the n-type region. Recombines holes with electrons. As a result, there is a mechanism in which electrons are transitioned from a high energy level to a low energy level and photons corresponding to the energy difference are emitted.
Examples of the material for the semiconductor laser include group IV elements such as germanium and silicon, and direct transition type III-V and II-VI group compounds not involving lattice vibration such as GaAs and InP. These materials may be not only a binary system but also a multi-element system such as a ternary system, a quaternary system, and a quinary system. Further, the laminated structure may be a double hetero structure provided with a clad layer, or may be composed of a lower clad, an active layer, and an upper clad. Furthermore, a multi quantum well structure may be applied.

  The wavelength conversion unit of the present invention may include a color filter and adjust the color purity as desired. The color filter is not particularly limited as long as it is usually used. Examples of pigments used in color filters include perylene pigments, lake pigments, azo pigments, quinacridone pigments, anthraquinone pigments, anthracene pigments, isoindoline pigments, isoindolinone pigments, phthalocyanine pigments, triphenylmethane basic dyes, and indanthrone. Various pigments such as pigments, indophenol pigments, cyanine pigments, dioxazine pigments, a mixture of two or more of these pigments, and a mixture of the pigment or pigment mixture and a binder resin (in a dissolved or dispersed solid state) Thing).

The wavelength conversion unit of the present invention includes the wavelength conversion member of the present invention, and emits incident light from a light source, preferably incident light in the above-described wavelength region, in red (wavelength 600 to 750 nm) with high quantum yield. The light can be emitted after being converted to. The quantum yield is as described above. Therefore, the wavelength conversion unit of this invention can be used suitably for the light emitting element of this invention mentioned later.
The wavelength conversion unit of the present invention can be produced by a known method.

[Light emitting element]
The light emitting device of the present invention has the wavelength conversion member of the present invention, preferably the wavelength conversion unit of the present invention. This light emitting element should just have the said member or unit, and is set to a suitable shape thru | or a dimension according to a use etc.
Although it does not specifically limit as a structure of the light emitting element of this invention, Each following structure is mentioned.
Specific configurations include, for example, a light source / wavelength conversion member, a light source / translucent substrate / wavelength conversion member, a light source / wavelength conversion member / translucent substrate, and a light source / translucent substrate / wavelength conversion member / translucency. Substrate, light source / wavelength conversion member / color filter, light source / translucent substrate / wavelength conversion member / color filter, light source / wavelength conversion member / translucent substrate / color filter, light source / translucent substrate / wavelength conversion member / Examples of the structure include a light-transmitting substrate / color filter, a light source / translucent substrate / wavelength conversion member / color filter / light-transmitting substrate, and a light source / wavelength conversion member / color filter / light-transmitting substrate.

  The said translucent board | substrate means the board | substrate which can permeate | transmit visible light 50% or more, Specifically, it is synonymous with the base material which the said wavelength conversion member may have. The color filter is also synonymous with the color filter that the wavelength conversion member may have. The shapes of the light-transmitting substrate and the color filter are not particularly limited, and may be a plate shape or a lens shape.

The light-emitting element of the present invention can be used for various applications, and preferably includes display devices such as various displays, lighting devices, and the like.
The display device is not particularly limited, and examples thereof include various displays, traffic signals, traffic display devices, liquid crystal backlights, liquid crystal front lights, and field sequential liquid crystal displays. The lighting device is not particularly limited, and examples thereof include a general lighting device (equipment), a local lighting device, and an interior lighting device.

  The light-emitting element of the present invention can be manufactured by sequentially stacking the components used in the above-described configuration, and can also be manufactured by bonding the components. The stacking order of the components is not particularly limited.

  Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited thereto.

The organic light emitting compounds and comparative compounds (1) to (9) used in Examples and Comparative Examples are shown below. In the following compounds, Me represents methyl, Et represents ethyl, and ^t Bu represents tert-butyl.

  Comparative compounds (1) to (4) are the pyromethene boron complex compounds A-8, A-25, A-26 and A-1 described in Patent Document 1, respectively. Comparative compound (5) is compound G-202 described in Patent Document 2, Comparative compound (8) is the compound described in paragraph [0146] of Patent Document 2, and Comparative compound (9) is described in Patent Document 2. The described compound R-1 (paragraph [0211]).

Hereinafter, a method for synthesizing the organic light-emitting compound used in each example will be described in detail, but the starting material, the dye intermediate, and the synthesis route are not limited thereto.
In the present invention, room temperature means 25 ° C.

Synthesis Example 1: Synthesis of organic light-emitting compound F-1 <Synthesis of compound (1-A)>
Compound (1-A) was synthesized based on the following scheme.
In the following scheme, Et represents ethyl and ⁱ Pr represents isopropyl.

In a 100 mL three-necked flask, 1.07 g of ethyl terephthalaldehyde and 50 mL of dichloromethane were introduced under a nitrogen atmosphere and stirred at room temperature. Thereto, 1.14 g of 2,4-dimethylpyrrole was added dropwise with water cooling, and then 5 drops of trifluoroacetic acid were added, followed by further stirring at room temperature for 1 hour. Thereto, 2.94 g of chloranil was added while cooling with water, and the mixture was further stirred at room temperature for 1 hour, and then 5.43 g of isopropylethylamine (N ⁱ Pr ₂ Et) was added dropwise, followed by stirring at room temperature for 30 minutes. Subsequently, 8.29 mL of boron trifluoride diethyl ether complex was added dropwise to the obtained liquid while cooling with water, and the mixture was stirred at room temperature for 1 hour.
Distilled water (100 mL) was added to the resulting reaction solution, and the extracted and separated organic layer was pre-dried with anhydrous sodium sulfate and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) and then recrystallized from methanol to obtain 1.02 g of compound (1-A).
Compound (1-A) was identified by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.
ESI-MS: [M−H] ⁻ = 395

<Synthesis of Organic Luminescent Compound F-1>
Based on the following scheme, an organic light-emitting compound F-1 was synthesized.
In the following scheme, Et represents ethyl.

2.63 g of compound (1-A) and 60 mL of 1,1,1,3,3,3-hexafluoro-2-propanol were introduced into a 300 mL three-necked flask and stirred at room temperature. N-iodosuccinimide (NIS) 3.60g was added there, and it stirred at room temperature for 1.5 hours. After concentrating the reaction solution under reduced pressure, 50 mL of an aqueous sodium thiosulfate solution (dissolved in 10 g of sodium thiosulfate) and 100 mL of methylene chloride were added, followed by extraction and liquid separation to obtain an organic layer. The organic layer was pre-dried with anhydrous sodium sulfate and concentrated under reduced pressure. By recrystallizing this crude product with ethanol, 3.27 g of compound (1-B) was obtained.
Next, 503 mg of compound (1-B), 1000 mg of 2,4,6-trimethylphenylboronic acid, 1152.2 mg of cesium fluoride, and 26 mL of methoxycyclopentane were introduced into a 100 mL three-necked flask and stirred at room temperature. After degassing under reduced pressure, a nitrogen atmosphere was established. Here, SPhos Pd G3 ((2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl) [2- (2′-amino-1,1′-biphenyl)] palladium (II) methanesulfonate, manufactured by Aldrich) 322 mg was added and heated to reflux for 1 hour. A saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (100 mL) were added to the resulting reaction solution, and the organic layer obtained by extraction and liquid separation was preliminarily dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography (TLC) (developing solvent: hexane / ethyl acetate) and then recrystallized from methylene chloride and methanol to obtain 325 mg of organic light-emitting compound F-1. .
Organic luminescent compound F-1 was identified by ESI-MS. The results are shown below.
ESI-MS: [M−H] ⁻ = 631

Synthesis Example 2: Synthesis of organic luminescent compound F-3 Synthesis of organic luminescent compound F-1 except that terephthalaldehyde acid was used in place of ethyl terephthalaldehyde acid in the synthesis of organic luminescent compound F-1. In the same manner, an organic light-emitting compound F-3 was synthesized. The obtained compound was identified by ESI-MS.
ESI-MS: [M−H] ⁻ = 603

Synthesis Example 3: Synthesis of organic light-emitting compound F-2 In the synthesis of organic light-emitting compound F-1, 4-formylbenzonitrile was used instead of ethyl terephthalaldehyde, and 2,4,6-trimethylphenylboronic acid was further used. An organic light-emitting compound F-2 was synthesized in the same manner as the synthesis of the organic light-emitting compound F-1, except that 2-methylphenylboronic acid was used instead. The obtained compound was identified by ESI-MS.
ESI-MS: [M−H] ⁻ = 528

Synthesis Example 4: Synthesis of organic luminescent compound F-9 In the synthesis of organic luminescent compound F-1, 4-methoxybenzaldehyde was used instead of ethyl terephthalaldehyde, and 2,4,6-trimethylphenylboronic acid was further converted. Instead, organic light emitting compound F-9 was synthesized in the same manner as the synthesis of organic light emitting compound F-1, except that 2,6-dimethylphenylboronic acid was used. The obtained compound was identified by ESI-MS.
ESI-MS: [M−H] ⁻ = 561

Synthesis example 5: Synthesis | combination of organic luminescent compound F-7 Based on the following scheme, the organic luminescent compound F-7 was synthesize | combined.

In the synthesis of compound (1-A), except that 2,3,5,6-tetrafluorobenzaldehyde was used instead of ethyl terephthalaldehyde, the above compound was synthesized in the same manner as in the synthesis of compound (1-A). (5-A) was synthesized.
Next, 100 mg of the compound (5-A) was measured in a 50 mL flask, dissolved in 3 mL of methylene chloride, 64 mg of aluminum trichloride was added thereto, and the mixture was heated to reflux for 30 minutes. Thereafter, 1 mL of 2-methoxyethanol was added to the reaction solution returned to room temperature, and the mixture was further reacted for 30 minutes. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and then the crude product was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) and then recrystallized from methanol / methylene chloride to obtain organic luminescent compound F-7. 40 mg was obtained. The obtained compound was identified by ESI-MS.
ESI-MS: [M−H] ⁻ = 743

[Preparation of luminescent resin composition for wavelength conversion and wavelength conversion member]
Example 1
<Production of wavelength-converting luminescent resin composition and film-shaped wavelength conversion member>
1 g of liquid A and 1 g of liquid B of silicone resin (KER-2500, two-component mixed addition curing type, manufactured by Shin-Etsu Chemical Co., Ltd.) are mixed, and then 20 mg of organic light-emitting compound F-1 (100 parts by mass of nonpolar resin) In addition, the mixture was mixed at 2000 rpm (rotation per minute) with a rotation / revolution mixer (Shinky Corporation, Awatori Rentaro), and degassed at 2200 rpm. The obtained mixed liquid (organic light-emitting compound F-1 was dispersed in a solid state in a nonpolar resin) was spin-coated on a glass plate at 3000 rpm, and heated at 150 ° C. for 2 hours to cure. I let you. In this way, a wavelength conversion luminescent resin composition (film-shaped wavelength conversion member) was produced. The thickness of the obtained wavelength conversion layer was 105 μm.

Examples 2-4, 6 and Comparative Examples 1-9
In Example 1, a wavelength-converting luminescent resin composition was obtained in the same manner as in Example 1, except that the organic luminescent compound or the comparative compound shown in Table 1 below was used instead of the organic luminescent compound F-1. (Film-shaped wavelength conversion member) was produced.

Example 5
10 g of thermoplastic polypropylene resin and 100 mg of organic luminescent compound F-1 (1 part by mass with respect to 100 parts by mass of nonpolar resin) were put into a lab plast mill and melt-kneaded at 200 ° C. for 10 minutes (organic light emission) The active compound F-1 was dispersed in a nonpolar resin in a solid state.) The obtained wavelength conversion light-emitting resin composition was sandwiched between two iron plates kept at 190 ° C. and heated for 5 minutes, and then pressed at a pressure of 5 to 10 mPa while cooling the iron plate. In this way, a film-like wavelength conversion member was produced. The thickness of the obtained wavelength conversion layer was 32 μm.

[Evaluation of Wavelength Conversion Luminescent Resin Composition and Film Wavelength Conversion Member]
About the produced wavelength conversion luminescent resin composition and film-form wavelength conversion member, the following characteristic was evaluated and the result was shown in Table 1.

<Evaluation of dispersion state>
About the produced wavelength conversion member, the dispersion state (solubility to nonpolar resin) of an organic light emitting compound or a comparative compound was confirmed.
Evaluation is performed on the specimen obtained by cutting the continuous phase (film) of the produced wavelength conversion member into 15 mm × 15 mm, using an absolute PL quantum yield measuring device: C9920-02 (manufactured by Hamamatsu Photonics), and the fluorescence spectrum is measured. It was measured. In the obtained spectrum, the peak intensity of the maximum emission wavelength (aggregation / association emission wavelength) in the dispersed state of the organic light emitting compound or the comparative compound and the maximum emission wavelength in the dissolved state (shorter than the above aggregation / association emission wavelength). The peak intensity of the peak wavelength was determined and determined as the maximum emission wavelength intensity in the dispersed state and the maximum emission wavelength intensity in the dissolved state, respectively. The ratio of the maximum emission wavelength intensity in the dissolved state to the maximum emission wavelength intensity in the dispersed state [the maximum emission wavelength intensity in the dissolved state / the maximum emission wavelength intensity in the dispersed state] was calculated.
Which of the following evaluation ranks included the calculated intensity ratio was determined.
In this test, when the evaluation is “A” and “B”, it indicates that the organic light-emitting compound is well dispersed in the nonpolar resin (silicone resin or polypropylene resin) in the solid state.
A: Less than 0.5 B: 0.5 or more, less than 1.0 C: 1.0 or more

<Measurement of quantum yield>
About the powder of the synthesized organic luminescent compound, the quantum yield was measured using an absolute PL quantum yield measuring apparatus: C9920-02 (manufactured by Hamamatsu Photonics). The excitation wavelength was a wavelength shorter by 50 nm than the maximum absorption wavelength of the organic light-emitting compound or comparative compound contained in each wavelength conversion member (in each example and comparative example, it was in the range of 300 to 500 nm). .
Which of the following evaluation ranks included the measured quantum yield was determined.
In this test, a quantum yield of practically required is an evaluation rank C or higher.
A: 0.30 or more B: 0.25 or more, less than 0.30 C: 0.20 or more, less than 0.25 D: 0.15 or more, less than 0.20 E: Less than 0.15

<Evaluation of wavelength conversion performance (emitted light)>
405 nm light was incident on each of the prepared wavelength conversion members, and the maximum emission wavelength of the emitted light was observed. The emitted light having the maximum emission wavelength of 600 to 750 nm was “red light”, and the emitted light having the wavelength of 495 to 570 nm was “green light”.

From the results in Table 1, the following can be understood.
Comparative Examples 1 to 9 using Comparative Compounds (1) to (9) that do not satisfy at least one of R ¹¹ , R ¹² , R ¹⁵ , R ¹⁶ and R ^{17 in} the above formula (1) defined in the present invention In both cases, the quantum yield was low, and it was confirmed that the comparative compound was dissolved in the silicone resin. Moreover, the light-emitting resin composition for wavelength conversion (wavelength conversion member) of Comparative Examples 4 to 8 emits light other than red light as main light emission. In Comparative Examples 1 to 3 and 9, although the emitted light is red light, the quantum yield is low. From these things, it turns out that the light-emitting resin composition for wavelength conversion (wavelength conversion member) of Comparative Examples 1 to 9 cannot convert the wavelength of emitted light into red light with high quantum efficiency.
Although the comparative compounds (2), (3) and (9) have a partial structure showing polarity, they do not satisfy R ¹¹ , R ¹² , R ¹⁵ and R ¹⁶ in the formula (1), so that they are solid. Although it was dispersed in a state, it did not show a sufficient quantum yield (Comparative Examples 2, 3 and 9). Comparative compounds that do not have polar partial structures and do not satisfy R ¹¹ , R ¹² , and R ^{15 to} R ¹⁷ all have low quantum yields despite being dissolved in nonpolar resins. (Comparative Examples 1, 4-8).

  On the other hand, the luminescent resin composition for wavelength conversion containing the organic luminescent compound represented by the formula (1) and a nonpolar resin, wherein the organic luminescent compound is dispersed in a solid state in the polar resin. (Wavelength conversion member) can emit the emitted light obtained by converting the wavelength of incident light into red light with high quantum yield (Examples 1 to 6). Thus, the organic light-emitting compound represented by the formula (1) can be dispersed in a solid state without being dissolved in a nonpolar resin, and the wavelength-converting light-emitting resin composition ( Wavelength conversion member) can be produced.

[Preparation and Evaluation of Wavelength Conversion Unit and Light-Emitting Element]
Examples 7-12
Using each wavelength conversion member produced in Examples 1 to 6 and a purple LED (model number: PS2N-UFLE, manufactured by Prolight Opto), the wavelength conversion unit and the light emitting element of Examples 7 to 12 were produced, respectively. . About the manufactured light emitting element, when the quantum yield was measured like the said <measurement of a quantum yield>, the same excellent result as Examples 1-6 was obtained in all.

  By Examples 1-6 and 7-12, even if the organic luminescent compound represented by said Formula (1) is disperse | distributing in a solid state, the luminescent resin composition for wavelength conversion which light-emits red light with a high quantum yield. And a wavelength conversion member can be prepared. Moreover, when this wavelength conversion light-emitting resin composition or wavelength conversion member is used, a wavelength conversion unit and a light-emitting element capable of emitting red light obtained by wavelength-converting incident light with a high quantum yield can be manufactured.

Claims (11)

A wavelength-converting luminescent resin comprising at least one organic luminescent compound represented by the following formula (1) and a nonpolar resin, wherein the organic luminescent compound is dispersed in a solid state in the nonpolar resin. Composition.

In formula (1), R ¹¹ and R ¹⁶ each independently represent a halogen atom, an alkyl group or a silyl group.
R ¹² and R ¹⁵ each independently represent a group represented by the following formula (Ar-1).
R ¹³ and R ¹⁴ are each independently a hydrogen atom, halogen atom, alkyl group, aryl group, heterocyclic group, ethenyl group, ethynyl group, amino group, silyl group, acyl group, alkoxy group, aryloxy group, alkylthio group. A group or an arylthio group;
R ¹⁷ represents an aryl group.
X ¹ and X ² each independently represent a halogen atom, an alkyl group, an aryl group, a heterocyclic group, a hydroxy group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an ethenyl group or an ethynyl group.
However, at least one of R ^{11 to} R ¹⁷ , X ¹ and X ² has a partial structure exhibiting polarity.

In formula (Ar-1), R ¹²¹ and R ¹²² each independently represent a halogen atom, an alkyl group, an amino group, a silyl group, an alkylthio group, an arylthio group, an ethenyl group or an ethynyl group, or a hydroxy group or a cyano group. , A carboxylic group, a carboxylic acid anhydride bond, an ester bond, a carbonyl bond, a —SO ₃ — bond, a carbonate bond, a urethane bond, an ether bond, a lactone ring structure, and a sultone ring structure. . n is an integer of 0-4. * Represents a bond part with the carbon atom forming the pyrrole ring in the formula (1). The partial structure showing the polarity of at least one of R ^{11 to} R ¹⁷ , X ¹ and X ² is a hydroxy group, a cyano group, a carboxy group, a carboxylic anhydride bond, an ester bond, a carbonyl bond, —SO ₃ —. The light-emitting resin composition for wavelength conversion according to claim 1, which is a partial structure selected from a bond, a carbonate bond, a urethane bond, an ether bond, a lactone ring structure and a sultone ring structure.   The luminescent resin composition for wavelength conversion according to claim 1 or 2, wherein the nonpolar resin is a silicone resin. The luminescent resin composition for wavelength conversion according to any one of claims 1 to 3, wherein each of R ¹³ and R ¹⁴ represents an alkyl group. The R ¹¹ , R ¹³ , R ^14, and R ¹⁶ are all alkyl groups, The wavelength-converting luminescent resin composition according to claim 1.   The wavelength conversion member which has a wavelength conversion part which consists of a luminescent resin composition for wavelength conversion of any one of Claims 1-5.   The wavelength conversion member according to claim 6, wherein the wavelength conversion unit is a wavelength conversion layer.   The wavelength conversion unit which has a light source and the wavelength conversion member of Claim 6 or 7.   The wavelength conversion unit according to claim 8, wherein the light source is a light emitting diode.   The wavelength conversion unit according to claim 8 or 9, which converts incident light into emitted light having a wavelength of 600 to 750 nm.   The light emitting element which has a wavelength conversion member of Claim 6 or 7.