KR20170095724A - red organic-inorganic composite light emitting material and method for preparing the same - Google Patents

Abstract

The present invention relates to a red organic-inorganic composite light emitting material and a method of preparing the red organic-inorganic composite light emitting material. The purpose of the present invention is to provide the red organic-inorganic composite light emitting material which has a higher luminance than a light emitting material of an existing organic metal coordination polymer, and enables excitation in a UV region and a blue region, and the method of preparing the red organic-inorganic composite light emitting material. The present invention provides the red organic-inorganic composite light emitting material having a composition of chemical formula 1, [(A_(x1),R_(x2))(L)_y(X)]_n, and the method of preparing the red organic-inorganic composite light emitting material. In chemical formula 1, A includes one or metal ions or metal compounds thereof selected from the group consisting of a monovalent metal ion selected from Li, Na or K, a divalent metal ion selected from Mg, Ca, Sr, Ba or Zn, a trivalent metal ion selected from Al or La, and a tetravalent metal ion selected from Zr or Ti; R includes one selected from Eu or an Eu compound; L includes one selected from aromatic compounds having at least two carboxylic acid groups; X includes one or more selected from phenanthroline and derivatives thereof; x1 is 0 <= x1 < 2; x2 is 0 < x2 <= 2; a sum of x1 and x2 is 0 < x_1+x_2 <= 2; y is 2 or 3; and n is any one integer selected from integers equal to or greater than 1.

Description

[0001] The present invention relates to a red organic-inorganic composite light emitting material and a method for preparing the same,

The present invention relates to a red organic-inorganic composite light-emitting material and a method of manufacturing the same, and more particularly, to a red organic-inorganic composite light-emitting material having a higher luminance than that of a conventional organometallic coordination polymer, And a method for producing the same.

Metal-organic coordination polymer is a porous organic-inorganic hybrid material having high surface area and molecular / nano-sized pores, and can be used as a gas storage material, an adsorbent, a sensor, a membrane, a functional thin film, a drug delivery material, , And the like.

This is a crucial parameter for designing novel organometallic compounds and their properties, such as reaction temperature, solvent, additives for controlling the structure, and pH.

 In addition, most metal cations, including a wide range of species, transition metals, rare earths, lanthanides, alkalis, alkaline earth metals and actinide metals, can be combined with various organic linker molecules to form a new structure framework. It is possible to control the properties according to the coordination environment which varies depending on the proper combination of metal ion and organic linker in the metal organic coordination polymer, the various geometrical structure according to the bonding type, and the flexibility of the skeleton structure.

However, most of them have been studied as gas storage materials, and there have been few studies on the light emitting materials using them. Accordingly, it is necessary to study the organometallic coordination polymer of a luminescent material which emits light by excitation in the UV region and the blue region and has high brightness.

According to Korean Unexamined Patent Publication No. 10-2014-0059982 entitled &quot; Moisture Sensitive Phosphor, a Method for its Preparation, and a Reversible Moisture Detection Sensor Including a Moisture Sensitive Phosphor &quot;, moisture sensitivity A method of producing a europium-phenanthroline complex as a phosphor, a process for producing the europium-phenanthroline complex, and a process for producing the europium-phenanthroline complex as a water-sensitive fluorescent substance, wherein the water- The present invention relates to a moisture detecting sensor, wherein the moisture-sensitive fluorescent substance has a europium complex represented by the following formula.

Wherein X is selected from the group consisting of _{-CH 3, -CH 2 CH 3,} -CH (CH 3) 2, -CF 3, -CF 2 CF 3, or -CF ₂ CF ₃ CF _3.

The patent discloses a method for preparing a europium-phenanthroline complex as a moisture-sensitive fluorescent substance capable of measuring moisture, and a method for measuring a change in fluorescence of a water-sensitive fluorescent substance. In general, a process for preparing a europium- However, the europium-phenanthroline complex itself is made of a molecular material, but the present invention is different from the synthesis of a coordination polymeric fluorescent substance that can be used as an LED.

Korean Patent Publication No. 10-2014-0059982

The present invention has been completed in accordance with a demand for research on organometallic coordination polymers of a light emitting material which emits light by excitation in the UV region and a blue region and has a high luminance, A compound having a high luminance and capable of being excited in a UV region and a blue region, and a method for producing the same.

The present invention relates to a red organic-inorganic composite light-emitting material and a method for producing the same, and provides a red organic-inorganic composite light-emitting material having a composition represented by the following general formula (1).

[Chemical Formula 1]

[(A _x1 , R _x2 ) (L) _y (X)] _n

In Formula 1, A is a monovalent metal ion selected from Li, Na, or K, or a bivalent metal ion selected from Mg, Ca, Sr, Ba, or Zn or a trivalent metal ion selected from Al or La, or Zr or Ti And R is at least one selected from the group consisting of Eu and Eu compounds, L is at least one selected from the group consisting of an aromatic group having at least two carboxylic acid groups And X is at least one selected from the group consisting of phenanthroline and its derivatives, x1 is 0? X1 <2, x2 is 0 <x2? 2, The sum of x1 and x2 is 0 < x _{1 +} x ₂ ? 2, y is 2 or 3, and n is any integer selected from an integer of 1 or more.

Further, it is also possible to use at least one selected from monovalent to tetravalent metal ions or metal compounds thereof, one selected from Eu or Eu compounds, one selected from aromatic compounds having at least two carboxylic acid groups, A step of weighing at least one raw material selected from troline and its derivatives, mixing the weighed raw materials in a solvent of 50 ml to 100 ml and uniformly mixing to prepare a mixture, and mixing the mixture at 90 to 210 ° C A compound represented by the following general formula (1): &quot; (1) &quot;

[Chemical Formula 1]

[(A _x1 , R _x2 ) (L) _y (X)] _n

In Formula 1, A is a monovalent metal ion selected from Li, Na, or K, or a bivalent metal ion selected from Mg, Ca, Sr, Ba, or Zn or a trivalent metal ion selected from Al or La, or Zr or Ti And R is at least one selected from the group consisting of Eu and Eu compounds, L is at least one selected from the group consisting of an aromatic group having at least two carboxylic acid groups And X is at least one selected from the group consisting of phenanthroline and its derivatives, x1 is 0? X1 <2, x2 is 0 <x2? 2, The sum of x1 and x2 is 0 < x _{1 +} x ₂ ? 2, y is 2 or 3, and n is any integer selected from an integer of 1 or more.

INDUSTRIAL APPLICABILITY The red organic electroluminescent compound of the present invention is a material capable of exciting in the UV and blue regions and having a higher luminance than the light emitting material of the conventional organometallic coordination polymer. This is because the range of color implementation is free, the half width is as narrow as 15 nm or less, and can be excited not only in UV but also in the blue region, so that it has a considerable effect as a light emitting material for LED.

1 shows a PL spectrum graph and an SEM image according to the present invention.
2 is an emission spectrum graph according to the present invention.
FIGS. 3 and 4 show excitation spectra of organometallic coordination polymers according to the present invention (X-axis shows the wavelength and Y-axis shows the emission intensity).
Fig. 5 shows the emission spectra of Figs. 3 to 4 (the X-axis shows the wavelength and the Y-axis shows the emission intensity).
FIG. 6 is a graph _showing the emission of an organometallic coordination polymer synthesized by changing A in Formula 1 according to the present invention to Al ₂ (SO ₄ ) ₃ , TiO ₂ , Zn (NO ₃ ) ₂ , Bi ₂ O ₃ and MnCO ₃ in addition to yttrium Is a graph showing the wavelength spectrum.
FIG. 7 is a graph _{showing the relationship} between the EDS of an organometallic coordination polymer synthesized by changing A in Formula 1 according to the present invention to Al ₂ (SO ₄ ) ₃ , TiO ₂ , Zn (NO ₃ ) ₂ , Bi ₂ O ₃ , Graph.
FIGS. 8 to 10 are images showing a single crystal structure of an organometallic coordination polymer according to the present invention, which is an image of a single crystal for one material, an image of the vicinity of one metal, two metals, and crystal structure 8, 9, and 10 show that [(Y _0.5 , Eu _0.5 ) 4,4'-oxybis (benzoic acid) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline)] n.
11 is a graph showing excitation and emission spectra according to Example 10 of the present invention.
12 is a graph showing excitation and emission spectra according to Example 11 of the present invention.
13 is a graph showing excitation and emission spectra according to Example 12 of the present invention.
14 is a graph showing excitation and emission spectra according to Example 13 of the present invention.
15 is a graph showing excitation and emission spectra according to Example 14 of the present invention.
16 is a graph showing the emission spectrum according to Examples 15-17 of the present invention.
17 is a graph showing excitation and emission spectra according to Example 18 of the present invention.
18 is a graph showing excitation and emission spectra according to Example 19 of the present invention.
19 is a graph showing excitation and emission spectra according to Example 20 of the present invention.

The present invention will be described in detail below, and the following embodiments are for illustrative purposes only and the present invention is not necessarily limited thereto.

The present invention relates to a red organic-inorganic composite light-emitting material for UV and blue LEDs and a method for producing the same.

First, the red organic-inorganic composite light-emitting material according to the present invention is excited by UV and blue regions of 350 to 450 nm as a light emitting material of an organometallic coordination polymer and exhibits an emission wavelength of 600 to 630 nm and has a half width of 15 nm or less Emitting organic light-emitting material.

Specifically, according to one embodiment of the present invention, the red organic-inorganic composite light-emitting material is based on a structure in which Eu ^{3 +} is added as an activator, and is an organic / inorganic composite light-

[Chemical Formula 1]

[(A _x1 , _Rx2 ) (L) _y (X)] _n

In Formula 1, A is a monovalent metal ion selected from Li, Na, or K, or a bivalent metal ion selected from Mg, Ca, Sr, Ba, or Zn or a trivalent metal ion selected from Al or La, or Zr or Ti And at least one metal ion selected from the group consisting of tetravalent metal ions,

R comprises one species selected from Eu or Eu compounds,

L comprises one kind selected from aromatic compounds having at least two carboxylic acid groups,

X includes at least one selected from phenanthroline and derivatives thereof,

x1 is 0? x1 <2, x2 is 0 <x2? 2, and the sum of x1 and x2 is 0 < x _{1 +} x ₂ ? 2,

y is 2 or 3, and n is any integer selected from an integer of 1 or more.

If the value is out of the range of x ₁ , x ₂ , or y, even if the synthesis is not performed properly or synthesis is performed, the light emission and luminance characteristics are poor.

The metal compound of Formula 1 may be, for example, ZnO, Y ₂ O ₃ , La ₂ O ₃ , Gd ₂ O ₃ , Al ₂ (SO ₄ ) ₃ , TiO ₂ , Zn (NO ₃ ) ₂ , Bi ₂ O ₃ or MnCO ₃ However, the scope of the present invention is not limited to the above examples.

As the Eu compound which can be used as R in the above formula (1), Eu, at least one metal ion and an oxide, or a metal oxide containing Eu may be used.

Specific examples of the Eu compound include ZnO: Eu, Y ₂ O ₃ : Eu, La ₂ O ₃ : Eu or Eu (NO ₃ ) ₃ .xH ₂ O, and Eu (NO ₃ ) ₃ In xH ₂ O, x is an integer selected from 1 to 6.

When Eu or Eu compounds are used, Eu characteristic peaks are obtained, which has a narrow half width of red and can be reproduced in high color when used in an LED.

The L in Formula 1 may be one kind selected from aromatic compounds having at least two carboxylic acid groups, for example, the following Formulas 2 to 8 may be used, but the scope of the present invention is not limited thereto .

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

X in Formula 1 may be at least one selected from phenanthroline and its derivatives. For example, compounds represented by the following Chemical Formulas 9 to 12 may be used, Is not limited.

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

R ₁ to R ₁₀ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _1-60 heterocyclic group containing at least one of N, O and S, and Q is N or CH.

As an example of the R ₁ to R ₁₀ More particularly, R ₁ is hydrogen (H), a cyano group (-CN) or a methyl group (CH ₃₎ and, R ₂ to R ₇ is a hydrogen (H), each independently , R ₈ is hydrogen (H) or methoxy (-OCH _3), R ₉ is hydrogen (H), C ₁ ~ C ₆ alkyl, phenyl, _{(phenyl), nC 1 ~ C} 6 alkyl phenyl (nC ₁ ~ C ₆ alkylphenyl, dimethylphenyl, trimethylphenyl, diethylphenyl, triethylphenyl, n-nitrophenyl, n-aminophenyl, n- sulfonyl phenyl (n-sulfonylphenyl), disulfonic sulfonyl phenyl (disulfonylphenyl, nC ₁ ~ C ₆ alkoxyphenyl _{(nC 1 ~ C 6 alkoxyphenyl)} , dimethoxyphenyl (dimethoxyphenyl, diethoxyphenylsilyl (diethoxyphenyl), n- pyridyl wherein R ₁₀ is selected from the group consisting of hydrogen (H), a C ₁ -C ₆ alkyl group, a phenyl (phenyl) group, a phenyl group, ) or nC ₁ ~ C ₆ alkyl phenyl (nC ₁ ~ C ₆ alkylphenyl) in You can use that option.

The C ₁ ~ C ₆ alkoxy are methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy is oxy, n is an integer of any one selected from 2 to 4, the o-, m-, p- it means.

More specifically, for example, the phenanthroline and derivatives thereof that can be used in the present invention may be at least one compound selected from the following formulas (13) to (28).

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

(25)

(26)

(27)

(28)

Use of such phenanthroline and its derivatives is effective in improving luminance compared to the case of not using phenanthroline and its derivatives.

In Formula 1, A _x1 , R _x2 X1 is 0? X1 <2, x2 is 0 <x2? 2, and the sum of x1 and x2 is 0 < x _{1 +} x _{2 &} lt _{; /} = ₂ , wherein a configuration including both A _x1 and R _x2 or a configuration including only R _x2 is A _the luminance is improved as compared with the configuration including only _x1 , and the advantage is obtained by reducing the unit cost by using less rare earth metal, and A _x1 alone can not exhibit luminescence characteristics.

The red orbasin composite light-emitting material of the present invention according to the above Formula 1 is characterized in that [Y _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3- ] Phenanthroline)] n [(Y _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3- f] [1,10] phenanthroline)] n [(Al _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [ _{phenanthroline)] n, [(Ti 0.5} , Eu 0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline)] n, _{[(Zn 0.5, Eu 0.5)} (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] _{phenanthroline)] n, [(Bi 0.5} , Eu 0.5 ] (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline] n, [(Mn _0.5 , Eu _0.5 ) (Y ₂ O ₃ : Eu) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] _{phenanthroline)] n, [(La 2} O 3: Eu) (4,4 ' - oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline )] n, [(Gd ₂ O _3: Eu) (4,4'- oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [ 1,10] _{phenanthroline)] n, [(La 2} O 3: Eu) ( Rick terephthalic Acid)) ₃ (2,3-dicyano-pyrazino [2,3-f] [1,10] phenanthroline Troll _{Lin)] n, [(Y 2} O 3: Eu) (4,4'- oxybis (benzoic _{acid)) 3 (tetrapyrido [3,2-} a: 2', 3'-c: 3'', 2 3'-j] phenazine)] n, [(Y _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (Pyrazino [2,3- f] [1,10] phenanthroline) _{0.5 (1,10-phenanthroline) 0.5] n, [(Y} 0.5, Eu 0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrido [ 2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline) _0.5 (pyrazino [2,3-f] [1,10] phenanthroline) _{0.5; n, [(Y 0.5, Eu} 0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline) _0.5 (3-methyl-pyrazino [ 2,3-f] [1,10] _{phenanthroline) 0.5] n, [Eu (} 1,3,5- tris (4-carboxyphenyl) benzene) ₃ (pyrido [2 ', 3': 5, 6] pyrazino [2,3-f] [1,10] phenanthroline)] n, [Eu (4,4'- oxybis (benzoic _{acid)) 3 (dipyrido [3,2-} a: 2', 3'-c] phenzine)] n or [Eu ( 4,4'-oxybis (benzoic acid)) ₃ (11-methoxydipyrido [3,2-a: 2 ', 3'-c] phenazine]] n is a preferable example.

FIG. 3 is a graph showing the results of measurement of the specific surface area of [(Y _0.5 , Eu _0.5 ) 4,4'-oxybis (benzoic acid) ₃ (pyrazino [2,3- f] [1,10] phenanthroline] 4 shows the excitation spectrum, and FIG. 4 shows the spectra of [(Y _0.5 , Eu _0.5 ) 4,4'-oxybis (benzoic acid) ₃ (pyrido [2 ', 3': 5,6] pyrazino [ 3-f] [1,10] phenanthroline) depicts the excitation spectrum of the n, 11 is _{[(Y 2 O 3: Eu} ) (4,4'- oxybis (benzoic acid)) ₃ (pyrimidin Figure [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline) will showing the excitation and emission spectra of n, 12 is [(La ₂ O ₃ : Eu] (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3- f] [1,10] phenanthroline] 13 shows the excitation and emission spectrum of [(Gd ₂ O ₃ : Eu) (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3' pyrazino [2,3-f] [1,10] phenanthroline) will showing the excitation and emission spectra of n, 14 is _{[(La 2 O 3: Eu} ) ( Rick terephthalic Acid)) ₃ ( 2,3-dicyanopyrazino [2,3-f] [l, 10] I depicts the excitation and emission spectra of the trawl Lin)] n, 15 is _{[(Y 2 O 3: Eu} ) (4,4'- oxybis (benzoic _{acid)) 3 (tetrapyrido [3,2-} a: 2 ', 3'-j] phenazine)] n and FIG. 16 shows the excitation and emission spectra of [(Y _0.5 , Eu _0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] _{phenanthroline)] n, [(Y 0.5} , Eu 0.5) (4, 4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline) _0.5 (pyrazino [2,3 -f] [1,10] _{phenanthroline) 0.5] n, [(Y} 0.5, Eu 0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1, 1] phenanthroline) _0.5 (3-methylpyrazino [2,3-f] [1,10] phenanthroline) _0.5 ] n, FIG. 18 shows the emission spectrum of [Eu 19 shows an excitation and emission spectrum of [Eu (4,4'-benzoic acid)] ₃ (dipyrido [3,2-a: 2 ', 3'-c] phenzine)] n, oxybis (benzoic _{acid)) 3 (11-methoxydipyrido [} 3,2-a: 2 ', 3'-c] phenazine)] n of excitation and emission's It shows a spectrum.

As shown in the drawings, the red organic-inorganic composite light-emitting material according to the present invention is excited by UV and blue regions of 350 to 450 nm and shows an emission wavelength of 600 to 630 nm. Emitting material used for LEDs.

In the method for producing a red organic-inorganic composite light-emitting material of the present invention,

First, at least one selected from monovalent to tetravalent metal ions or metal compounds thereof, one selected from Eu or Eu compounds, one selected from aromatic compounds having at least two carboxylic acid groups, Weighing at least one raw material selected from troline and its derivatives,

The weighed raw materials are mixed in a solvent such as 50 ml to 100 ml of water (H ₂ O), propanol, ethanol, methanol, dimethylformamide (DMF) or dimethylacetamide (DMA) Comprising the steps of:

And a step of synthesizing the mixture at a temperature of from 90 to 210 ° C to prepare a red organic-inorganic hybrid light-emitting material having a composition represented by the following formula (1).

[Chemical Formula 1]

[(A _x1 , _Rx2 ) (L) _y (X)] _n

In Formula 1, A is a monovalent metal ion selected from Li, Na, or K, or a bivalent metal ion selected from Mg, Ca, Sr, Ba, or Zn or a trivalent metal ion selected from Al or La, or Zr or Ti And R is at least one selected from the group consisting of Eu and Eu compounds, L is at least one selected from the group consisting of an aromatic group having at least two carboxylic acid groups And X is at least one selected from the group consisting of phenanthroline and its derivatives, x1 is 0? X1 <2, x2 is 0 <x2? 2, the sum of x1 and x2 is 0 <x ≤2 ₁₊ x _2, y is 2 or 3, n is an integer selected from an integer of 1 or more.

At least one selected from the above monovalent to tetravalent metal ions or metal compounds thereof and at least one member selected from Eu or Eu compounds and at least one aromatic compound having at least two carboxylic acid groups, At least one selected from the group consisting of leucine and its derivatives can be weighed in a ratio of 0.01 to 0.19 mol, 0.1 to 0.19 mol, 0.01 to 0.6 mol, and 0.01 to 0.2 mol, respectively.

If it is out of the above range, it can not be synthesized properly or if it is synthesized, the luminance of the material is not good and unreacted material is produced, which is not economical.

In addition, when the single crystal image is confirmed, the aromatic compound having at least two carboxylic acid groups in one metal is coordinated to three times, and the phenanthroline and its derivatives are coordinated in the same ratio. A proper luminescent material can not be synthesized.

When each of the weighed raw materials is mixed with a solvent, it can be synthesized at a temperature of 90 to 210 ° C. If the synthesis is carried out at a temperature lower than 90 ° C., a red organic compound light emitting material is not formed. The luminance of the red light-emitting composite light-emitting material is lowered.

Such a production method is shown in Scheme 1 as follows.

[Reaction Scheme 1]

As shown in Reaction Scheme 1, the red orbasin composite light-emitting material of the present invention is doped with a cationic metal at a portion A, and thus the electron-transport effect and the crystallinity of the skeleton structure are different from those of the conventional metal-organic skeleton doped with Eu only to R There is an advantage that the light emitting property can be improved by using it for an LED or the like.

The red organic-inorganic hybrid luminescent material having the formula (1) prepared by the above method has an emission wavelength of 600 to 630 nm for the excitation light in the UV and blue regions and has a narrow half width and a high luminance of 15 nm The characteristics of the light emitting material are shown.

Hereinafter, the present invention will be described in detail with reference to examples and comparative examples.

Example

Example  One

(NO ₃ ) ₃ .6H ₂ O compound of 0.1 mol ratio, Eu (NO ₃ ) ₃ .5H ₂ O compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, (13) was weighed and 50 ml of the weighed raw material was added to water (H ₂ O), and the mixture was uniformly mixed. Then, the mixture was mixed with 150 organic-inorganic composite light-emitting material of the organic metal coordination polymer having ℃ Scheme 1 below by combining the composition at a temperature of _{[(Y 0. 5, Eu 0} . 5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [ 2,3-f] [1,10] phenanthroline)] n.

[Reaction Scheme 1]

As shown in FIG. 1, the organometallic coordination polymer prepared by this method exhibits a red emission characteristic of about 614.1 nm at near UV and a narrow half width of 12.4 nm. That is, it is understood that the phosphor is a red light emitting material for a LED having a narrow half width and a high brightness as compared with a conventional phosphor.

Example  2

Was prepared in the same manner as in Example 1, except that it was synthesized at a temperature of 170 占 폚.

Example  3

Was prepared in the same manner as in Example 1, except that it was synthesized at 190 ° C.

Example  4

(NO ₃ ) ₃ .6H ₂ O compound of 0.1 mol ratio, Eu (NO ₃ ) ₃ .5H ₂ O compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, (H ₂ O) was prepared by weighing the pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline It was placed uniformly mixing 50 ml and then combining the mixture at 150 ℃ temperature organic-inorganic composite light-emitting material of the organic metal coordination polymer _{[(Y 0. 5, Eu 0} . 5) (4,4'- oxybis (benzoic acid )) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline]] n.

Example  5

0.1 mol ratio of the _{Al 2 (SO 4) 3,} 0.1 mol ratio of Eu (NO _{3) 3} · 4,4'- oxybis pyrazino of (acid), 0.2 mol ratio of the compound 5H ₂ O, 0.2 mol ratio [ 2,3-f] [1,10] phenanthroline (Formula 13) was weighed, and 50 ml of the weighed raw material was added to water (H ₂ O), and the mixture was uniformly mixed. (Al _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline of organic metal coordination polymer )] n.

Example  6

0.1 mol of the ratio of TiO _2, 0.1 mol ratio _{Eu (NO 3) 3 · 5H} 2 O compound, 0.2 mol ratio of the 4,4'-oxybis (benzoic acid), 0.2 mol of the non-pyrazino [2,3-f ] [1,10] phenanthroline (Formula 13) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O) and uniformly mixed. Then, the mixture was synthesized at a temperature of 150 ° C. to obtain an organometallic coordination polymer (Ti _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline] Respectively.

Example  7

(NO ₃ ) ₂ in 0.1 mol ratio, Eu (NO ₃ ) ₃ .5H ₂ O compound in 0.1 mol ratio, 4,4'-oxybis (benzoic acid) in 0.2 mol ratio, pyrazino [2 , 3-f] [1,10] phenanthroline (Formula 13) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O), and the mixture was uniformly mixed. (Zn _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline), an organometallic coordination polymer- ] n.

Example  8

0.1 mole ratio of Bi ₂ O ₃ , 0.1 mole ratio of Eu (NO ₃ ) ₃ .5H ₂ O compound, 0.2 mole ratio of 4,4'-oxybis (benzoic acid), 0.2 mole ratio of pyrazino [2,3 -f] [1,10] phenanthroline (Formula 13) were weighed, 50 ml of the weighed raw materials were added to water (H ₂ O), and the mixture was homogeneously mixed. (Bi _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline)] n .

Example  9

0.1 mol ratio of MnCO _3, 0.1 mol ratio of _{Eu (NO 3) 3 · 5H} 2 O compound, 0.2 mol ratio of the 4,4'-oxybis (benzoic acid), 0.2 mol of the non-pyrazino [2,3-f ] [1,10] phenanthroline (Formula 13) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O) and uniformly mixed. Then, the mixture was synthesized at a temperature of 150 ° C. to obtain an organometallic coordination polymer the organic-inorganic composite light-emitting material _{[(Mn 0.5, Eu 0.5)} (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline) preparing a n Respectively.

Example  10

(Y ₂ O ₃ : Eu ^{3 +} compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, pyrido [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline (Formula 17) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O), and the mixture was uniformly mixed. (Y ₂ O ₃ : Eu) (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline)] n.

Example  11

0.1 mol ratio of La ₂ O ^_3: Eu ₃ ⁺ compound, 0.2 mol ratio of the 4,4'-oxybis (benzoic acid), 0.2 mol of the non-pyrido also [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline (Formula 17) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O), and the mixture was uniformly mixed. (La ₂ O ₃ : Eu) (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline)] n.

Example  12

0.1 mol ratio of Gd ₂ O ^_3: Eu ₃ ⁺ compound, 0.2 mol ratio of the 4,4'-oxybis (benzoic acid), 0.2 mol of the non-pyrido also [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline (Formula 17) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O), and the mixture was uniformly mixed. (Gd ₂ O ₃ : Eu) (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2 , 3-f] [1,10] phenanthroline)] n.

Example  13

0.1 mol of a non-La ₂ O ^_3: Eu ₃ ⁺ compound, 0.2 mol terephthalic rigs Acid (Formula V) of the non-, 0.2 mol pyrazino [2,3-f] of the ratio [1,10] phenanthroline -2 , And 3-dicarbonitrile (Formula 14) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O) and uniformly mixed. Then, the mixture was synthesized at a temperature of 150 ° C to obtain the organometallic coordination polymer complex light emitting materials _{[(La 2 O 3: Eu} ) ( Rick terephthalic Acid)) ₃ (pyrazino [2,3-f] [1,10] - phenanthroline-2,3-carbonitrile Preparation of n Respectively.

Example  14

₃ : 2 ', 3'-c: 3''of Y ₂ O ₃ : Eu compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, tetrapyrido [ , 2''-h: 2''', 3''-j] phenazine (Formula 28) were weighed, and 50 ml of the weighed raw material was added to water (H ₂ O) organic-inorganic composite material of the light emitting synthesized organometallic coordination polymer temperature at 150 ℃ _{[(Y 2 O 3: Eu} ) (4,4'- oxybis (benzoic _{acid)) 3 (tetrapyrido [3,2-} a: 2', 3'-c: 3'', 2''-h: 2''', 3''-j] phenazine)] n.

Example  15

(NO ₃ ) ₃ .6H ₂ O compound of 0.1 mol ratio, Eu (NO ₃ ) ₃ .5H ₂ O compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, (17) and 1,10-phenanthroline of formula (16) in a ratio of 0.1 mol are added to a solution of the pyrido [2 ', 3': 5,6] pyrazino [2,3- ) Were weighed, and 50 ml of the weighed raw materials were mixed in water (H ₂ O) and mixed uniformly. Then, the mixture was synthesized at a temperature of 150 ° C to obtain an organometallic coordination polymer organic / inorganic hybrid fluorescent material _{[(Y 0. 5, Eu 0} . 5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline) _0.5 (1,10 Phenanthroline) _{0. 5} ] n was prepared.

Example  16

(NO ₃ ) ₃ .6H ₂ O compound of 0.1 mol ratio, Eu (NO ₃ ) ₃ 5H ₂ O compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, 2,3-f] [1, 10] phenanthroline (Formula 17) and 0.1 mole ratio of pyridino [2,3-f] [1, , 10] phenanthroline (Formula 13) was weighed, and 50 ml of the weighed raw material was added to water (H ₂ O) and uniformly mixed. Then, the mixture was synthesized at 150 ° C. to prepare organic organic-inorganic composite light-emitting material of the metal coordination polymer _{[(Y 0. 5, Eu 0} 5.) (4,4'- oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3-f] [1,10] phenanthroline) _0.5 (pyrazino [2,3-f] [1,10] phenanthroline) _0.5 ] n.

Example  17

(NO ₃ ) ₃ .6H ₂ O compound of 0.1 mol ratio, Eu (NO ₃ ) ₃ .5H ₂ O compound of 0.1 mol ratio, 4,4'-oxybis (benzoic acid) of 0.2 mol ratio, 2,3-f] [1,10] phenanthroline (Formula 17) and 0.1 mol ratio of 3-methylpyrazino [2,3- f] [1,10] phenanthroline (Formula 15) were weighed, and 50 ml of the weighed raw materials were added to water (H ₂ O) and mixed uniformly. The mixture was then synthesized at 150 ° C., 1-inorganic composite light-emitting material of the organic metal coordination polymer having the composition _{[(Y 0. 5, Eu 0} . 5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1 , 10] phenanthroline) _0.5 (3-methylpyrazino [2,3-f] [1,10] phenanthroline) _0.5 ] n.

Example  18

(2 ', 3': 5, 2 ', 3', 5'-bipyridyl) of 0.1 mol ratio of Eu (NO ₃ ) ₃ .5H ₂ O compound, 0.2 mol ratio of 1,3,5- 6] pyrazino [2,3-f] [1,10] phenanthroline (Formula 17) was weighed and 50 ml of the weighed raw material was added to water (H ₂ O) (1, 3, 5-tris (4-carboxyphenyl) benzene) ₃ (pyrido [2 ', 3' : 5,6] pyrazino [2,3-f] [1,10] phenanthroline)] n.

Example  19

A solution of 0.1 mol of Eu (NO ₃ ) ₃ .5H ₂ O compound, 0.2 mol of 4,4'-oxybis (benzoic acid), 0.2 mol of dipyrido [3,2-a: ] phenzine (Formula 18) were weighed, and 50 ml of the weighed raw material was added to water (H ₂ O) and uniformly mixed. Then, the mixture was synthesized at a temperature of 150 ° C. to obtain an organometallic coordination polymer- Eu (4,4'-oxybis (benzoic acid)) ₃ (dipyrido [3,2-a: 2 ', 3'-c] phenzine)] n.

Example 20

A solution of 11-methoxydipyrido [3,2-a: 2 ', 3', 2'-bipyridyl] of 0.1 molar ratio of Eu (NO ₃ ) ₃ .5H ₂ O compound, 0.2 molar ratio of 4,4'- -c] phenazine (Chemical Formula 19) were weighed, and 50 ml of the weighed raw material was added to water (H ₂ O) and uniformly mixed. Then, the mixture was synthesized at a temperature of 150 ° C. to obtain an organic- The material [Eu (4,4'-oxybisan)] ₃ (11-methoxydipyrido [3,2-a: 2 ', 3'-c] phenazine)] n was prepared.

Comparative Example

Comparative Example  One

Was prepared in the same manner as in Example 1, except that it was synthesized at 210 ° C.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit and scope of the invention as defined in the appended claims. There will be.

Claims (21)

1. A red emitting organic light emitting material having a composition represented by the following formula (1).
[Chemical Formula 1]
[(A _x1 , _Rx2 ) (L) _y (X)] _n
In Formula 1, A is a monovalent metal ion selected from Li, Na, or K, or a bivalent metal ion selected from Mg, Ca, Sr, Ba, or Zn or a trivalent metal ion selected from Al or La, or Zr or Ti And at least one metal ion selected from the group consisting of tetravalent metal ions,
R comprises one species selected from Eu or Eu compounds,
L comprises one kind selected from aromatic compounds having at least two carboxylic acid groups,
X includes at least one selected from phenanthroline and derivatives thereof,
x1 is 0? x1 <2, x2 is 0 <x2? 2, and the sum of x1 and x2 is 0 < x _{1 +} x ₂ ? 2,
y is 2 or 3, and n is any integer selected from an integer of 1 or more. The method according to claim 1,
The metal compound is ZnO, Y ₂ O ₃ , La ₂ O ₃ , Gd ₂ O ₃ , Al ₂ (SO ₄ ) ₃ , TiO ₂ , Zn (NO ₃ ) ₂ , Bi ₂ O ₃ or MnCO ₃ And a metal complex compound selected from the group consisting of a metal complex compound and a metal complex compound. The method according to claim 1,
Eu compound is a metal compound containing Eu and at least one kind of metal ion and oxide or Eu. The method of claim 3,
Eu compound is _{ZnO: Eu, Y 2 O 3} : Eu, La 2 O 3: Eu or Eu (NO _{3) 3} · is one selected from xH ₂ O, x in the _{Eu (NO 3) 3 · xH} 2 O Is an integer selected from 1 to 6. The method according to claim 1,
L represents a group selected from the following formulas (2) to (8).
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

The method according to claim 1,
X is at least one selected from the following formulas (9) to (12).
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

R ₁ to R ₁₀ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _1-60 heterocyclic group containing at least one of N, O and S, and Q is N or CH. The method according to claim 6,
Wherein R ₁ is hydrogen (H), a cyano group (-CN) or a methyl group (CH ₃₎ and, R ₂ to R ₇ are each independently hydrogen (H), an amino group (-NH _2), a methyl group (CH ₃₎ or phenyl (phenyl), and, R ₈ is hydrogen (H) or methoxy (-OCH ₃₎ and, R ₉ is hydrogen (H), C ₁ ~ C ₆ alkyl, phenyl, (phenyl), nC ₁ ~ C ₆ alkyl phenyl (nC ₁ to C ₆ alkylphenyl), dimethylphenyl, trimethylphenyl, diethylphenyl, triethylphenyl, n-nitrophenyl, n-aminophenyl n-aminophenyl), n- sulfonyl phenyl (n-sulfonylphenyl), disulfonic sulfonyl phenyl (disulfonylphenyl, nC ₁ ~ C ₆ alkoxyphenyl _{(nC 1 ~ C 6 alkoxyphenyl)} , dimethoxyphenyl (dimethoxyphenyl, diethoxyphenylsilyl (diethoxyphenyl) n-pyridyl, pyrimidyl, furfuryl, naphthalenyl or pyrenyl, R ₁₀ is hydrogen (H), C ₁ -C ₆ Alkyl group, phenyl or nC ₁ to C ₆ alkylphenyl (nC ₁ to C ₆ alkylphenyl) C ₁ -C ₆ alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy, n is any integer selected from 2 to 4, o-, m-, and p-, respectively. The method according to claim 6,
X is at least one selected from the following formulas (13) to (27).
[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

(25)

(26)

(27)

The method according to claim 1,
X is a group represented by the following formula (28).
(28)

The method according to claim 1,
The above-mentioned formula (1) can be prepared by reacting [(Y _0.5 , Eu _0.5 ) 4,4'-oxybis (benzoic acid)] ₃ (pyrazino [2,3- f] [1,10] phenanthroline] _0.5 , Eu _0.5 ) (4,4'-oxybis (benzoic acid)) ₃ (pyrido [2 ', 3': 5,6] pyrazino [2,3- f] [1,10] phenanthroline) _{] n, [(Al 0.5,} Eu 0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] phenanthroline)] n, [(Ti _0.5 , Eu _0.5) (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] _{phenanthroline)] n, [(Zn 0.5} , Eu 0.5) (4, 4,4'-oxybis (benzoic acid)) ₃ (pyrazino [2,3-f] [1,10] _{phenanthroline)] n, [(Bi 0.5} , Eu 0.5) (4,4'- oxybis (benzoic acid )) ₃ (pyrazino [2,3-f] [1,10] phenanthroline)] n or _{[(Mn 0.5, Eu 0.5)} (4,4'- oxybis (benzoic acid)) ₃ (pyrazino [ 2,3-f] [1,10] phenanthroline)] n. The method according to claim 1,
Wherein the red organic-inorganic hybrid light-emitting material having the composition represented by the general formula (1) has a half width of 15 nm or less. In order to produce the red organic-inorganic composite light-emitting material according to claim 1,
At least one member selected from the group consisting of monovalent to tetravalent metal ions or metal compounds thereof and at least one member selected from Eu or Eu compounds and at least one aromatic compound having at least two carboxylic acid groups and at least one member selected from the group consisting of phenanthroline And a derivative thereof;
Mixing the weighed raw materials in a solvent of 50 ml to 100 ml and uniformly mixing to prepare a mixture;
And a step of synthesizing the mixture at a temperature of from 90 to 210 ° C. 2. The method for producing a red organic-inorganic hybrid light emitting material according to claim 1,
[Chemical Formula 1]
[(A _x1 , _Rx2 ) (L) _y (X)] _n
In Formula 1, A is a monovalent metal ion selected from Li, Na, or K, or a bivalent metal ion selected from Mg, Ca, Sr, Ba, or Zn or a trivalent metal ion selected from Al or La, or Zr or Ti And at least one metal ion selected from the group consisting of tetravalent metal ions,
R comprises one species selected from Eu or Eu compounds,
L comprises one kind selected from aromatic compounds having at least two carboxylic acid groups,
X includes at least one selected from phenanthroline and derivatives thereof,
x1 is 0? x1 <2, x2 is 0 <x2? 2, and the sum of x1 and x2 is 0 < x _{1 +} x ₂ ? 2,
y is 2 or 3, and n is any integer selected from an integer of 1 or more. 13. The method of claim 12,
At least one selected from the group consisting of monovalent to tetravalent metal ions or metal compounds thereof in an amount of 0.01 to 0.19 mol and Eu or Eu compounds in a proportion of 0.1 to 0.19 mol, A method for producing a red organic-inorganic hybrid light emitting material characterized by comprising weighing one kind of aromatic compound having at least two acid groups and one or more kinds of raw materials selected from phenanthroline and derivatives thereof in a ratio of 0.01 to 0.2 mol . 13. The method of claim 12,
Wherein the solvent is at least one selected from the group consisting of H ₂ O, propanol, ethanol, methanol, dimethylformamide (DMF), and dimethylacetamide (DMA). 13. The method of claim 12,
The metal compound is ZnO, Y ₂ O ₃ , La ₂ O ₃ , Gd ₂ O ₃ , Al ₂ (SO ₄ ) ₃ , TiO ₂ , Zn (NO ₃ ) ₂ , Bi ₂ O ₃ or MnCO ₃ Wherein the light-emitting layer is formed on the substrate. 13. The method of claim 12,
Eu compound is _{ZnO: Eu, Y 2 O 3} : Eu, La 2 O 3: Eu or Eu (NO _{3) 3} · is one selected from xH ₂ O, x in the _{Eu (NO 3) 3 · xH} 2 O Is an integer selected from 1 to 6. 13. The method of claim 12,
And L is at least one selected from the following formulas (2) to (8).
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

13. The method of claim 12,
X is at least one selected from the following formulas (9) to (12).
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

R ₁ to R ₁₀ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _1-60 heterocyclic group containing at least one of N, O and S, and Q is N or CH. 19. The method of claim 18,
Wherein R ₁ is hydrogen (H), cyano (-CN) or methyl (CH ₃ ), R ₂ to R ₇ are each independently hydrogen (H) and R ₈ is hydrogen (H) or methoxy OCH ₃₎ and, R ₉ is hydrogen _{(H), C 1 ~ C} 6 alkyl, phenyl, _{(phenyl), nC 1 ~ C} 6 alkyl phenyl _{(nC 1 ~ C 6 alkylphenyl)} , dimethylphenyl (dimethylphenyl), trimethylphenyl ( trimethylphenyl, diethylphenyl, triethylphenyl, n-nitrophenyl, n-aminophenyl, n-sulfonylphenyl, disulfonyl phenyl (disulfonylphenyl, nC ₁ ~ C ₆ alkoxyphenyl _{(nC 1 ~ C 6 alkoxyphenyl)} , dimethoxyphenyl (dimethoxyphenyl, diethoxyphenylsilyl (diethoxyphenyl), pyridyl n- (n-pyridyl), Premier dill (pyrimidyl), peppers Wherein R ₁₀ is selected from the group consisting of hydrogen (H), a C ₁ -C ₆ alkyl group, phenyl or nC ₁ to C ₆ alkylphenyl (nC ₁ - C ₆ alkylphenyl) may be selected from the C ₁ ~ C ₆ alkoxy is methoxy And n is an integer of 2 to 4, and is o-, m-, or p-. The organic or inorganic composite according to claim 1, A method for producing a light emitting material. 19. The method of claim 18,
X is at least one selected from the following formulas (13) to (27).
[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

(25)

(26)

(27)

13. The method of claim 12,
X is a group represented by the following formula (28).
(28)

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