JP2008144129A - Compound for organic el and organic el device - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound for an organic EL having a host material and a light-emitting dopant as a light-emitting layer to enable high efficiency and long life of light-emission. <P>SOLUTION: This compound for an organic EL comprises a polymer molecule including a light-emitting molecule and molecules represented by formulas (1), (2) and (3) as constituent units. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an organic EL device used for a display, a display light source, and the like. Specifically, the present invention relates to an organic EL compound suitably used for a coating type organic EL device and an organic EL device using the same.

  In recent years, the development of organic electroluminescence devices (organic EL devices) using organic electroluminescence elements (organic EL elements) has been accelerated as spontaneous emission type displays replacing liquid crystal displays. As such an organic EL device and a manufacturing method thereof, techniques such as Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4 are known.

  By the way, conventionally, in an organic EL device (organic EL device), there is a technique that uses a host material and a light emitting dopant as a material structure of a light emitting layer in order to increase the efficiency of light emission, change the light emission color, and extend the lifetime. Are known. Such a technique is particularly frequently used in a device in which an organic material in an organic EL device is arranged by a vapor deposition method, and is formed by using an inkjet method (droplet discharge method) or a spin coating method. In a coating type organic EL device of a polymer material to be filmed, it is not so often used.

Here, the meaning / features of the above-mentioned “host material and light-emitting dopant” are described below.
(1) The host material is a material that can flow both holes and electrons.
(2) In an organic EL device that does not use a light emitting dopant in the light emitting layer, light emission from the host material is observed, but when the light emitting dopant and the host material are used in combination, light emission from the host material is almost observed. The light emitting dopant mainly emits light.
(3) The spectrum of EL emission observed in an organic EL device using a host material and a light emitting dopant in combination is fluorescence or phosphorescence at the emission center in the light emitting dopant. The luminescence center mentioned here refers to a part of the luminescent dopant, means an organic molecular skeleton capable of emitting strong fluorescence / phosphorescence, and means a partial skeleton whose emission waveform is substantially determined by this part.
JP 2000-323276 A JP 2002-536492 A Japanese Unexamined Patent Publication No. 63-264692 JP 2003-40845 A

The reason why the technique of using a host material and a light-emitting dopant in combination in the above-described polymer material-coated organic EL device has not been used so much is considered to be due to the following causes (problems).
(1) When a mixed solution of a host and a light emitting dopant is applied, a phenomenon in which the light emitting dopant bleeds is observed. In general, when a mixed solution of low molecular weight material is applied / dried in a polymer, a phenomenon that the low molecular weight material appears on the surface layer or segregates in the coating film during drying is observed. to cause.
(2) The function of trapping holes and electrons of the light emitting dopant material is low. This is remarkable when the host is a conjugated polymer. In the case of a conjugated polymer, since holes and electrons flow preferentially in the host polymer molecule, it is expected that the light-emitting dopant does not easily trap holes and electrons.
(3) Development of luminescent dopant materials was delayed. This is because, for the above two reasons, in the field of polymer-coated organic EL devices, the host + light-emitting dopant system was less effective than the vapor deposition type EL (low molecular EL), so the development of the material Seems to have been delayed.

  The present invention has been made in view of the above circumstances, and provides a compound for organic EL that functions as a light-emitting dopant in a light-emitting layer, particularly as a material for forming a light-emitting layer that enables higher efficiency and longer life of light emission. In addition, an object of the present invention is to provide an organic EL device using the same. Specifically, the compound for organic EL and the organic EL device of the present invention are to provide an organic EL device that emits light in an emission color region determined by a light emitting molecule and has improved luminous efficiency and luminance half-life.

As a result of intensive studies to achieve the above object, the present inventor has obtained the following knowledge.
The following solutions can be taken for the problem shown in (1) above.
-By increasing the molecular weight of the luminescent dopant, it is possible to prevent the luminescent dopant from bleeding during coating / drying. The entire dopant is preferably π-conjugated (including general π-conjugated as well as conjugated with an N atom interposed), but in a coating type organic EL, it is necessary to dissolve in an appropriate solvent. Therefore, depending on the design, a high molecular weight can be achieved with a non-conjugated linking group with an appropriate molecular weight.

Moreover, the following solutions can be taken with respect to the problem shown in said (2).
-When increasing the molecular weight in the solution (1) above, the function of the dopant is improved by incorporating a functional group capable of preferentially trapping holes or electrons into the luminescent dopant molecule as a molecular design policy. . In particular, the function as a dopant is improved by incorporating a functional group having a hole trapping function into the molecule.
-It is preferable that the luminescent center in a dopant and the functional group which has a hole trap function are connected by (pi) conjugation. This is because π-conjugation provides the same effect as the emission center directly hole trapped.
As a guideline for improving the hole trapping property, it is the IP (ionization potential) value of the host material, and it should be easily oxidized to the same level or more as the host material.
As a result of further research on the basis of such knowledge, the present inventor completed the present invention.

That is, the compound for organic EL of the present invention is a compound for organic EL as a luminescent material used in an organic EL device, and a luminescent molecule that determines the luminescent color of the luminescent material, and the following formulas (1) to ( It consists of a polymer molecule having a molecule represented by 4) as a constituent unit.

（ただし、Ｒはアルキル基、アリール基、又はアルキルアリール基を表す。）

(However, R represents an alkyl group, an aryl group, or an alkylaryl group.)

（ただし、Ｒ’は水素、アルキル基、又はアルキルアリール基を表す。）

(However, R ′ represents hydrogen, an alkyl group, or an alkylaryl group.)

Moreover, in the said compound for organic EL, it is preferable that the said light emitting molecule | numerator consists of 1 type selected from the molecule | numerator shown by following formula (5)-Formula (7).

In the polymer molecule, the light emitting molecule represented by the formula (5) functions as a molecular unit that emits yellow light in the organic EL device, and the light emitting molecule represented by the formula (6) functions as a molecular unit that emits yellow light in the organic EL device. The light emitting molecule represented by the formula (7) functions as a molecular unit that emits green light in the organic EL device.
Moreover, what is shown in Formula (1) functions as a hole trap unit, and Formulas (2) and (3) function as a connecting unit for increasing the molecular weight. Further, the one shown in the formula (2) also functions as an electron trap unit, and has a function of controlling the amount of electrons flowing in the light emitting layer while being minute. Moreover, what is shown in Formula (4) is a functional group for preventing the molecular end from becoming a halogen element.

  Since the polymer molecule can trap holes, the polymer molecule traps the holes flowing in the light emitting layer by using the polymer molecule in the light emitting layer of the organic EL device. Generate. Then, this cation traps the electrons flowing in the light emitting layer, whereby recombination occurs in the polymer molecule, and the light emitting unit (light emitting molecule) is a molecule such as the above formula (5) to formula (7). The unit emits EL.

Here, the above “recombination” means that the molecule at the emission center is excited by the holes and electrons trapped by the polymer molecule.
That is, energy released in the process of relaxation from the “excited state” to the “ground state” is observed as EL light emission.
Under such a configuration, by using the polymer molecule in an organic EL device, it is possible to obtain particularly high-efficiency and long-lived light emission, that is, light emission in an emission color region determined by the light-emitting molecule.

（ただし、Ａは下記式（９）〜（１１）で示される基から選択された一種を表し、Ｒはアルキル基、アリール基、又はアルキルアリール基を表し、Ｒ’は水素、アルキル基、又はアルキルアリール基を表す。また、ｍ，ｎ，ｐはそれぞれ１以上の整数を表し、ｑ，ｂは０以上の整数を表す。ｒは１以上の整数を表す。） Moreover, in the said compound for organic EL, it is preferable that a polymer molecule is what is shown by following formula (8).

(However, A represents one selected from the groups represented by the following formulas (9) to (11), R represents an alkyl group, an aryl group, or an alkylaryl group, and R ′ represents hydrogen, an alkyl group, or Represents an alkylaryl group, m, n and p each represents an integer of 1 or more, q and b represent an integer of 0 or more, and r represents an integer of 1 or more.)

As described above, by using the polymer molecule in an organic EL device, light emission with high efficiency and long life can be obtained.
In the above formula (8), r represents an oligomer unit constituting the polymer molecule (meaning the lowest unit composed of formula (7) to formula (9) and formula (1) to formula (4)). Is an integer representing the degree of polymerization.
In the above formula (8), q = 0 is desirable. However, depending on the solvent type of the coating ink, the solubility may be lowered if there is no structural unit represented by formula (3), or the solubility may be increased depending on the value of r. Since it worsens, it may become an integer of q = 1-4.

In the organic EL compound, in the oligomer unit represented by the formula (8), the integer m representing the number of units represented by A is preferably 1 or 2. Further, when there are two or more emission centers in the dopant molecule, adverse effects such as concentration quenching occur, so m = 1 is more preferable.
The oligomer configured in this way means r = 1 in the above formula (8).
A sufficient EL emission luminance can be obtained by the molecular design of the oligomer as described above.

In the organic EL compound, in the oligomer unit represented by the formula (8), an integer n representing the number of units represented by the formula (1) which is a unit having a hole trap function is 2 or more. Is preferred.
With such a molecular design of the oligomer unit, sufficient EL emission luminance can be obtained.

Further, in the compound for organic EL, in the oligomer unit represented by the above formula (8), in the above formula (2), which is a unit that functions as a connecting unit for increasing the molecular weight and has a function as an electron trap. The integer p representing the number of units shown is preferably 1 to 4.
Such molecular design of the oligomer unit makes it possible to improve the solubility in a solvent. In addition, the flow of electrons can be controlled, and the light emission efficiency can be optimized.

In the organic EL compound, in the structure of the oligomer unit represented by the formula (8), at least one unit represented by the A and the unit represented by the formula (1) is directly connected. Is preferred. This is because the coupling between the unit represented by A and the unit represented by the formula (1) has a great influence on the fluorescence waveform, that is, the EL waveform.
Specifically, when the group represented by the above formula (9) is used as the unit represented by the above A, there are two direct bonds between the formula (9) and the formula (1) in order to obtain yellow light emission. It is preferable. This is because when there is only one direct bond between the formula (9) and the formula (1), yellowish green is exhibited, and when it is 0, blue green is exhibited.
In addition, when the group represented by the above formula (10) is used as the unit represented by A, at least one direct bond between the formula (10) and the formula (1) exists in order to obtain yellow light emission. It is preferable.
Further, when the group represented by the above formula (11) is used as the unit represented by the above A, at least one direct bond between the formula (11) and the formula (1) exists in order to obtain green light emission. It is preferable.

By such a molecular design of the oligomer unit, the hole trapping property can be improved, and the light emission efficiency and the luminance half-life can be improved.
In the organic EL compound, in the structure of the oligomer unit represented by the formula (8), an integer representing the number of units represented by the formula (4) which is a functional group for preventing the molecular terminal from being a halogen. b is preferably 2.

Moreover, the organic EL device of the present invention uses the above-mentioned compound for organic EL.
A favorable organic EL device can be obtained by using the above-mentioned compound for organic EL.
Moreover, in the said organic EL device, it is preferable to use the said compound for organic EL for a light emitting layer.
By using the compound for organic EL in the light emitting layer, it becomes possible to draw out the characteristics of the material, and it is possible to obtain a device having good light emission efficiency and luminance half-life characteristics.

Moreover, in the said organic EL device, it is preferable to use said organic EL compound as a light emitting dopant material in the light emitting layer.
Here, the light emitting layer means a portion (layer) that emits EL when a voltage is applied to the organic EL device and a current flows. In the case of a coating type organic EL, the material constituting the light emitting layer is usually usually only one type. In addition to electron / hole injection / transport, it has three functions of EL emission.

The light emitting dopant is a name used in the light emitting layer and used when the light emitting function is used as a main purpose among the above three functions. At that time, an organic material mainly used for the function of injecting / transporting holes and electrons is also used at the same time, and the material is called a host material.
By using the above organic EL compound as a light-emitting dopant material in the light-emitting layer, it becomes possible to extract the characteristics of the material, and to obtain a device having a function of yellow light emission and excellent emission efficiency and luminance half-life characteristics. It becomes possible.

In the organic EL device, the light emitting layer is formed of the light emitting dopant material and the host material,
The light-emitting dopant and the host material in the light-emitting layer are in such a ratio that the k value in weight% represented by the following formula (12) is 0.5 wt% or more and 10.0 wt% or less. It is preferably contained.
k = (a / (b + c)) × 100 (12)
(However, a in the above formula (12) is a weight occupied by units composed of light emitting molecules such as the above formulas (5) to (7) in the above light emitting dopant material, and b is a light emitting dopant used. (Weight of material, c is the weight of host material used.)

  In general, since the light emitting site in the light emitting dopant (the light emitting molecule in the light emitting dopant material) has a strong fluorescence intensity, if the light emitting dopant can efficiently trap electrons and holes in the device (element), the above k It is said that EL light can be emitted even when the value is about 0.1% by weight. However, if the amount is too small, the host material may emit light due to insufficient energy transfer or insufficient trapping of electrons and holes. Therefore, the lower limit of the k value is set to 0.5% by weight. Is preferable. In addition, it is difficult to specify the upper limit value, and the upper limit value may be 20% by weight to 30% by weight only for developing the light emitting function of the luminescent dopant. However, if the addition amount is excessive, concentration quenching is sufficient. EL light emission cannot be obtained. Therefore, it is preferable that the practical upper limit considering the luminous efficiency is 10% by weight.

In the organic EL device, the light emitting layer is formed of the light emitting dopant material and the host material, and the host material has at least one material skeleton selected from fluorene, arylamine, and anthracene. It is preferably a homopolymer or a copolymer polymer.
The host material is desired to have a property of transporting holes and electrons satisfactorily as its performance. In addition, the energy gap between HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in the molecular orbitals is based on the units (light emitting molecules) represented by the above formulas (5) to (7) in the polymer molecules. Is also desired to be large. Furthermore, it is desired that the vacuum level of LUMO (lowest unoccupied molecular orbital) is higher than that of the polymer represented by the above formula (8).
By satisfying such performance, both holes and electrons are favorably injected from the host material into the light emitting dopant, and the light emission efficiency and lifetime are improved.

In the organic EL device, it is preferable that at least one hole injection layer or hole transport layer is provided between the light emitting layer and the anode.
In this way, the hole injection property into the light emitting layer is further improved, and the light emission efficiency is improved.

The HOMO (maximum occupied molecular orbital) can be measured using a photoelectron spectrometer (AC-1) manufactured by Riken Keiki Co., Ltd.
The energy gap between HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) can be measured using the thin film absorption spectrum of the host material used. The absorption edge at a long wavelength is used as an energy gap. Further, the LUMO vacuum level can be easily determined from the HOMO vacuum level and the HOMO-LUMO gap.

In the organic EL device, it is preferable that the light emitting layer is manufactured by being applied by a spin coat method or a droplet discharge method.
As described above, the organic EL device has good luminous efficiency and luminance half-life characteristics because the above-mentioned organic EL compound is applied by spin coating or droplet discharge method to produce a light emitting layer. It becomes.
Here, since the compound for organic EL is an oligomer or a polymer molecule, the compatibility with the polymer of the host material is good. Accordingly, the host material and the light emitting dopant material can be uniformly dispersed in the light emitting layer.
In addition, since the compound for organic EL has a large molecular weight, part or all of the organic EL compound is decomposed at the time of vapor deposition, and the characteristics of the obtained organic EL device are impaired.

Hereinafter, the present invention will be described in detail.
First, 1st Embodiment of the compound for organic EL of this invention is described based on the synthesis example.

（ただし、合成反応上での理論値として、ｍ＝１，ｎ＝４，ｐ＝４，ｑ＝０，ｂ＝２，ｒ＝１であり、分子量ＭＷ＝２８５７である。） [First Embodiment]
(Compound for organic EL)
As 1st Embodiment of the compound for organic EL of this invention, the polymer molecule shown to following formula (13) was produced by the synthesis method based on the following synthesis examples.

(However, as theoretical values in the synthesis reaction, m = 1, n = 4, p = 4, q = 0, b = 2, r = 1, and molecular weight MW = 2857.)

<Synthesis Example 1>
3,10-dibromo-7,14-diphenylacenaphtho [1,2-k] fluoranthene (isomer: 3,11-dibromo-7,14-diphenylacenaphtho [1,2-k] fluoranthene) (intermediate) ) Was synthesized by the synthesis method shown in FIG. 1 as follows.
First, 5 g of 7,14-diphenylacenaphtho [1,2-k] fluoranthene was introduced into a 300 cm ³ Schlenk tube in the atmosphere.
Next, 50 cm ³ of chloroform was added thereto as a solvent and dissolved by heating at 60 ° C. Further, 50 cm ³ of dimethylformamide (DMF) was added thereto as a solvent. After cooling to 40 ° C., 3.9 g of N-bromosuccinimide (NBS) was added in 4 portions over 3 hours. After the addition, the mixture was heated at 50 ° C. for 1 hour, and then left to stir at room temperature for 10 hours.
After the reaction, the mixture was washed and separated with chloroform / water using a separatory funnel. Impurities were removed by silica gel chromatography and reprecipitation. The developing solvent for silica gel chromatography was toluene: hexane = 1: 3, and reprecipitation was performed with dichloromethane / hexane.
As a result, 3.2 g (yield 48.2%) of a yellowish white solid was obtained.

<Synthesis Example 2>
2-Bromo-9,9-di-n-octylfluorenyl-7-boronic acid was synthesized by the synthesis method shown in FIG.
First, the Schlenk tube 200 cm ³ was purged with Ar, 2,7-dibromo-9,9-di -n- octylfluorene 4g (7.3E-3mol), and was with sodium dried solution THF100cm ³ was added was . The solution was cooled to -70 ° C. Thereto was added 4.9 cm ³ of a 1.5 mol / l n-butyllithium hexane solution and left for 1 hour. While maintaining cooling, 1.1 g (7.5E-3 mol) of triethyl boronate was added and reacted for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. An appropriate amount of magnesium sulfate was added to the separated THF solution to remove water. After removing magnesium sulfate using a filter paper, hexane was added to precipitate the target product. Purification was performed by a reprecipitation method. As the solvent, THF and hexane were used.

<Synthesis Example 3>
1- (4-Bromobenzyl) -4-phenylboronic acid was synthesized by the synthesis method shown in FIG. 3 as follows.
First, the Schlenk tube 200 cm ³ was purged with Ar, 4,4'-bis-bromophenyl methane 5g (1.5E-2mol), and was with sodium dried solution THF50cm ³ was added were. The solution was then cooled to -70 ° C. Thereto was added 10.2 cm ³ (1.5E-2 mol) of a 1.5 mol / l n-butyllithium hexane solution and left for 1 hour. Next, 2.2 g (1.5E-2 mol) of triethyl boronate was added while the cooling state was maintained, and the reaction was performed for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. Subsequently, an appropriate amount of magnesium sulfate was added to the separated THF solution to remove moisture. After removing magnesium sulfate using filter paper, the solvent was removed using an evaporator.
As a result, 4 g of a transparent viscous material was obtained. In this state, it was used for the next reaction.

<Synthesis Example 4>
The EL material (EL material 1), that is, the organic EL compound according to the first embodiment of the present invention was synthesized by the synthesis route shown in FIG.
First, in an Ar-substituted 300 cm ³ Schlenk tube, 0.5 g (7.86E-4 mol) of diphenylacenaphtho [1,2-k] fluoranthene derivative synthesized earlier (Synthesis Example 1), 4-bromodiphenylamine 0. 78 g (3.14E-3 mol) was added, and then 100 cm ³ of dry xylene was added thereto and heated to 130 ° C.
Next, 0.1 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ), 0.3 g of t-butoxypotassium, and 0.1 g of tris-t-butylphosphine were added thereto, and the oil bath was set at 140 ° C. Reacted for hours. After 5 hours, the temperature was cooled to 80 ° C., 25 cm ^{3 of} ethanol and 50 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto, and the mixture was stirred for 15 minutes.
Then, 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid (Synthesis Example 2) 1.6 g (3.14E-3 mol), tetrakistriphenylphosphine palladium complex (Pd (PPh _{3 4} ) 0.1 g was added and reacted for another 4 hours. After 4 hours, 0.19 g (1.57E-3 mol) of commercially available phenylboronic acid was further added and reacted for 4 hours. During the reaction, a small amount of Ar continued to flow to prevent oxygen and water contamination.
After the reaction, air was bubbled into the reaction solution for 30 minutes under heating. Next, after cooling the reaction solution to room temperature, it was transferred to a 1 liter separatory funnel and subjected to toluene extraction and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation. Xylene was used as a developing solvent for silica gel chromatography. The solvent used for reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 0.6 g (yield 27%) of a red-orange solid was obtained. (However, the molecular weight was calculated as 2857.)

（ただし、合成反応上での理論値として、ｍ＝１，ｎ＝４，ｐ＝４，ｑ＝２，ｂ＝２，ｒ＝１であり、分子量ＭＷ＝３１９０である。） [Second Embodiment]
(Compound for organic EL)
As a second embodiment of the compound for organic EL of the present invention, a polymer molecule represented by the following formula (14) was prepared by a synthesis method based on the following synthesis example.

(However, as theoretical values in the synthesis reaction, m = 1, n = 4, p = 4, q = 2, b = 2, r = 1, and molecular weight MW = 3190.)

<Synthesis Example 5>
The EL material (EL material 2) represented by the above formula (14) was synthesized by the synthesis route shown in FIG.
First, in an Ar-substituted 300 cm ³ Schlenk tube, 0.5 g (7.86E-4 mol) of diphenylacenaphtho [1,2-k] fluoranthene derivative synthesized earlier (Synthesis Example 1), 4-bromodiphenylamine 0. 78 g (3.14E-3 mol) was added, and then 100 cm ³ of dry xylene was added thereto and heated to 130 ° C.
Next, 0.1 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ), 0.3 g of t-butoxypotassium, and 0.1 g of tris-t-butylphosphine were added thereto, and the oil bath was set at 140 ° C. Reacted for hours. After 5 hours, the temperature was cooled to 80 ° C., 25 cm ^{3 of} ethanol and 50 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto, and the mixture was stirred for 15 minutes.
Thereafter, 0.46 g (1.57E-3 mol) of 1- (4-bromobenzyl) -4-phenylboronic acid (Synthesis Example 3) and 0.1 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) were added. In addition, the reaction was further continued for 4 hours. Four hours later, 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid (Synthesis Example 2) 1.61 g (3.14E-3 mol), tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) 0.1 g was added and reacted for 4 hours. Subsequently, 0.19 g (1.57E-3 mol) of commercially available phenylboronic acid was added and reacted for another 5 hours. During the reaction, a small amount of Ar continued to flow to prevent oxygen and water contamination.
After the reaction, air was bubbled into the reaction solution for 30 minutes under heating. Next, the reaction solution was cooled to room temperature, transferred to a 1 liter separatory funnel, extracted with toluene, and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation. Xylene was used as a developing solvent for silica gel chromatography. The solvent used for reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 0.6 g (yield 24%) of a red solid was obtained. (However, the molecular weight was calculated as 3190.)

（ただし、合成反応上での理論値として、ｐ＝１５０である。） Next, a host material for EL was synthesized and produced as follows.
First, as the host 1, a polymer molecule represented by the following formula (15) was produced by a synthesis method based on the following synthesis example.

(However, the theoretical value in the synthesis reaction is p = 150.)

<Synthesis Example 6>
As an EL host material (host 1), polyfluorene represented by the above formula (15) was synthesized as follows based on the synthesis method shown in FIG.
First, 5 g (9.7E-3 mol) of 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid synthesized by the synthesis method shown above in an Ar-substituted 200 cm ³ Schlenk tube. ), And commercially available phenylboronic acid 0.008 g (6.6E-5 mol) and bromobenzene 0.01 g (6.6E-5 mol) were metered in. Thereto, distilled ethanol 50 cm ^3, was added to produce a solution of distilled toluene 100 cm ^3. Further, 0.56 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and 30 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto and reacted at 80 ° C. for 10 hours.
After the reaction, the reaction solution was cooled to room temperature, transferred to a 1 liter separatory funnel and subjected to toluene extraction, and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for the reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 2 g of white solid (yield: 52% as a recovered amount) was obtained.

（ただし、合成反応上での理論値として、ｐ＝３，ｎ＝１，ｒ＝５０である。） Next, as the host 2, a polymer molecule represented by the following formula (16) was produced by a synthesis method based on the following synthesis example.

(However, as theoretical values in the synthesis reaction, p = 3, n = 1, and r = 50.)

<Synthesis Example 7>
Based on the synthesis method shown in FIG. 7, a copolymer of fluorene and triphenylamine represented by the above formula (16) was synthesized as an EL host material (host 2) as follows.
First, 5 g (9.7E-3 mol) of 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid synthesized by the synthesis method shown above in an Ar-substituted 200 cm ³ Schlenk tube. ), 4-bromo-triphenylaminoboronic acid 1.2 g (3.2E-3 mol), and commercially available phenylboronic acid 0.008 g (6.6E-5 mol), bromobenzene 0.01 g (6.6E-5 mol) ) Was weighed in. Thereto, distilled ethanol 50 cm ^3, was added to produce a solution of distilled toluene 100 cm ^3. Further, 0.56 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and 30 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto and reacted at 80 ° C. for 5 hours.
After the reaction, the reaction solution was cooled to room temperature, transferred to a 1 liter separatory funnel and subjected to toluene extraction, and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for the reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 1.5 g of a white solid (yield: 33% as a recovered amount) was obtained.

（ただし、合成反応上での理論値として、ｐ＝３，ｎ＝１，ａ＝１，ｒ＝５０である。） Next, a polymer molecule represented by the following formula (17) was produced as a host 3 by a synthesis method based on the following synthesis example.

(However, as theoretical values in the synthesis reaction, p = 3, n = 1, a = 1, and r = 50.)

<Synthesis Example 8>
Based on the raw material synthesis method shown in FIG. 8 and the host material synthesis method shown in FIG. 9, a copolymer of fluorene, triphenylamine and anthracene represented by the above formula (17) is used as the EL host material (host 3). This was synthesized as follows.

(Raw material synthesis: Synthesis of 9-bromoanthrace-10yl-boronic acid)
First, the Schlenk tube 200 cm ³ was purged with Ar, was dispersed solution 9,10-dibromo-anthracene 2g (5.9E-3mol), and by addition of sodium THF50cm ³ drying. The solution was then cooled to -70 ° C. Thereto was added 4 cm ³ (5.9E-3 mol) of a 1.5 mol / l n-butyllithium hexane solution and left for 1 hour. While maintaining the cooled state, 0.87 g (5.9E-3 mol) of triethyl boronate was added and reacted for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, 100 cm ^{3 of} THF was added and completely dissolved, and then neutralized with a saturated aqueous sodium carbonate solution so that the pH became 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. An appropriate amount of magnesium sulfate was added to the separated THF solution to remove water. After removing magnesium sulfate using a filter paper, the solvent was removed using an evaporator, and hexane was added to precipitate the target product.
Purification was performed by a reprecipitation method. Moreover, THF and hexane were used as the solvent.
As a result, 1 g (yield 56%) of a pale yellowish white (colored light green) solid was obtained.

(Synthesis of host material)
First, 5 g (9.7E-3 mol) of 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid synthesized by the synthesis method shown above in an Ar-substituted 200 cm ³ Schlenk tube. ), 4-bromo-triphenylaminoboronic acid 1.2 g (3.2E-3 mol), 9-bromoanthrace-10 yl-boronic acid 0.96 g (3.2E-3 mol), and commercially available phenylboronic acid 0.008 g (6.6E-5 mol) and 0.01 g (6.6E-5 mol) of bromobenzene were metered in. Thereto, distilled ethanol 50 cm ^3, was added to produce a solution of distilled toluene 100 cm ^3. Further, 0.7 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and 30 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto and reacted at 80 ° C. for 5 hours.
After 5 hours, 0.2 g (1.65E-3 mol) of phenylboronic acid was added, and the mixture was further reacted for 1 hour. After 1 hour, the reaction solution was cooled to room temperature, transferred to a 1 liter separatory funnel, extracted with toluene, and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 2.1 g of a pale yellowish white solid was obtained (41% yield as the recovered amount).

  The EL materials 1 and 2 thus synthesized and produced (the compound for organic EL of the present invention) are used as light emitting dopant materials, and the EL host materials (hosts 1, 2 and 3) are described later. By mixing at an appropriate ratio, a material for forming a light emitting layer in an organic EL device can be obtained.

For each of the above syntheses, the following documents were referenced.
(Synthetic Reference)
Polymers for Advanced Technologies, 15 (5), 266-269; 2004
Eur. Pat. Appl., 1298117, 02 Apr 2003
Helvetica Chimica Acta, 85 (7), 2195-2213; 2002
Organometallics, 20 (24), 5162-5170; 2001
Journal of Organic Chemistry, 69 (3), 987-990; 2004
Journal of Organic Chemistry, 62 (3), 530-537; 1997
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 22B (3), 225-9; 1983

(Organic EL device)
Next, an embodiment of the organic EL device of the present invention will be described with reference to FIG.
In FIG. 10, reference numeral 100 denotes an organic EL device. The organic EL device 100 includes a light-transmitting anode (first electrode) 102 and a cathode (second electrode) 105 on a light-transmitting substrate 101. A functional layer is provided between the anode 102 and the cathode 105. The functional layer is configured by laminating a hole injection / transport layer 103 and a light emitting layer 104. The organic EL device 100 having such a configuration is a bottom emission method in which light emitted from the light emitting layer 104 is emitted from the translucent substrate 101 side.

  The substrate 101 is configured by forming a driving element made of a TFT element and various wirings on a transparent substrate such as a glass substrate, and an insulating layer and a planarizing film are formed on the driving elements and various wirings. An anode 102 is formed therethrough. The anode 102 is formed by patterning for each pixel region formed on the substrate 101, and is connected to a driving element made of a TFT element, the above-described various wirings, and the like, and is composed of ITO in this embodiment. .

  The hole injection / transport layer 103 transports holes injected from the anode 102 to the light emitting layer 104, and is formed of 3,4-polyethylenedioxythiophene / polystyrene sulfonic acid (PEDOT / PSS). is there. The light emitting layer 104 is formed of a material for forming a light emitting layer containing the organic EL compound of the present invention, and is a yellow light emitting layer whose emission wavelength band corresponds to yellow. Based on such a configuration, the organic EL device 100 displays yellow as a whole.

  The cathode 105 is formed so as to cover all the pixel regions, and is formed by sequentially stacking a LiF layer, a Ca layer, and an Al layer from the light emitting layer 104 side. On the cathode 105, a sealing material 200 for bonding the sealing substrate 201 is formed. The sealing material 200 is made of a thermosetting resin or an ultraviolet curable resin.

  Next, an example of a method for manufacturing the organic EL device 100 having such a configuration will be described. This manufacturing method includes an anode forming step, a substrate processing step (plasma processing step), a hole injection / transport layer forming step, a light emitting layer forming step, a cathode forming step, and a sealing step.

[Anode formation process]
A transparent substrate (not shown) made of glass or the like was prepared, and a thin film transistor (TFT) element (not shown) and various wirings were formed on the transparent substrate by a known method. Further, after forming an interlayer insulating layer and a planarizing film, indium tin oxide (ITO) is formed on the entire surface by sputtering or vapor deposition, and this is patterned for each pixel by photolithography to form pixel electrodes (anodes). ) 102 was obtained. Note that the pixel electrode 102 may be a light-transmitting conductive material, and may be formed using indium zinc oxide or the like in addition to ITO.

[Substrate processing process]
The glass substrate on which the anode (pixel electrode) 102 was formed was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol, and then pulled up from boiling ethanol and dried. Next, this transparent electrode surface was subjected to oxygen plasma treatment at atmospheric pressure to modify the substrate surface to be hydrophilic, and then the substrate was set on a spin coat holder in the atmosphere.

[Hole injection / transport layer formation process]
Next, as a material for forming a hole injecting / transporting layer, H.P. C. An aqueous dispersion of PEDOT / PSS (1: 2.5 by weight) (BAYTRON (registered trademark) P), a Starck product, was spin-coated in air, and then 30 minutes at 100 ° C. under nitrogen. Drying was performed to form a hole injection / transport layer 103. The film thickness after drying was 50 nm.

[Light emitting layer forming step]
As a material for forming the light emitting layer 104, EL materials 1 and 2 (light emitting dopant material), which are the compounds for organic EL of the present invention produced in the above embodiment, and EL host materials 1, 2, and 3 (host material) are used. The material which becomes is produced. The formation materials obtained by combining these EL materials 1 and 2 (light-emitting dopant material) and EL host materials 1, 2, and 3 (host material) are shown in Table 1 below as examples 1 to examples. 6. Further, for comparison, the forming materials made only of the EL host materials 1, 2, 3 (host materials) are referred to as Comparative Examples 1 to 3.
Then, the EL materials 1, 2 (light emitting dopant material) and the EL host materials 1, 2, 3 (host material) are mixed in an appropriate ratio, and further dissolved in a solvent to form a solution (ink). The solution was formed into a film with a thickness of, for example, 100 nm on the surface of the hole injection / transport layer 103 by a spin coating method to form the light emitting layer 104. At this time, after coating film formation, drying was performed at 100 ° C. for 30 minutes under nitrogen. In addition, when the above solution was formed, the hole injection / transport layer 103 was not compatible.
In addition, it can also form into a film by the droplet discharge method (inkjet method) using said solution instead of a spin coat method.

[Cathode formation process]
After the formation of the light emitting layer 104, the vacuum reach was 10 ⁻⁷ to 10 ⁻⁸ Torr using a vacuum deposition apparatus, and LiF was deposited to 1 nm, Ca was 5 nm, and Al was 200 nm in this order to form the cathode 105.
[Sealing process]
Finally, in the sealing step, a sealing material 200 made of a thermosetting resin or an ultraviolet curable resin was applied to the entire surface of the cathode 105 to form a sealing layer. Further, a sealing substrate 201 was attached on the sealing layer (sealing material 200). This sealing step is preferably performed in an inert gas atmosphere such as nitrogen, argon, or helium.

In this way, the organic EL device 100 shown in FIG. 10 is obtained.
In the organic EL device 100, the light emitting layer 104 formed using the organic EL compound of the present invention described above has superior light emission characteristics (luminance) and reliability (luminance half-life) from the experimental results described below. Therefore, the light emission is more efficient and has a longer life than the conventional one.

(Examples 1-6, Comparative Examples 1-3)
As described above, the materials shown in Table 1 below were used as the material for forming the light emitting layer 104.

Here, in Example 1, (EL material 1) represented by the above formula (13) and (host 1) represented by the above formula (15) were used at a mixing ratio (weight ratio) of 1: 7.2. This was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed by the spin coat method as mentioned above, and the organic EL device as an example product was obtained.
In Example 2, (EL material 2) represented by the above formula (14) and (host 1) represented by the above formula (15) were used at a mixing ratio (weight ratio) of 1: 6.5. Was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 3, (EL material 1) represented by the above formula (13) and (host 2) represented by the above formula (16) were used at a mixing ratio (weight ratio) of 1: 7.2. Was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 4, (EL material 2) represented by the above formula (14) and (host 2) represented by the above formula (16) were used at a mixing ratio (weight ratio) of 1: 6.5. Was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 5, (EL material 1) represented by the above formula (13) and (host 3) represented by the above formula (17) were used at a mixing ratio (weight ratio) of 1: 7.2. Was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 6, (EL material 2) represented by the above formula (14) and (host 3) represented by the above formula (17) were used at a mixing ratio (weight ratio) of 1: 6.5. Was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.

In Comparative Example 1, only (Host 1) represented by the above formula (15) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.
In Comparative Example 2, only (Host 2) represented by the above formula (16) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.
In Comparative Example 3, only (Host 3) represented by the above formula (17) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.

(Device evaluation)
A voltage was applied to each of the above organic EL devices so that a current of DC 100 mA / cm ² flowed through the light emitting layer 104 to emit light.
The EL waveforms are shown in FIGS. 11 shows the EL waveforms of Examples 1, 3, and 5, and FIG. 12 shows the EL waveforms of Examples 2, 4, and 6. 13 shows the EL waveform of Comparative Example 1, FIG. 14 shows the EL waveform of Comparative Example 2, and FIG. 15 shows the EL waveform of Comparative Example 3.

Further, the chromaticity, luminance, and luminance half-life (time until the luminance is reduced to half of the initial luminance) were measured, and the results are also shown in Table 1 above.
In Example 1, the applied voltage for obtaining the current was 6.0V.
Similarly, in Example 2, the applied voltage is 5.9 V, in Example 3, the applied voltage is 6.1 V, in Example 4, the applied voltage is 6.0 V, and in Example 5, the applied voltage is 5.8 V. In Example 6, the applied voltage was 5.8 V, in Comparative Example 1, the applied voltage was 6.0 V, in Comparative Example 2, the applied voltage was 5.8 V, and in Comparative Example 3, the applied voltage was 5.7 V. It was.

  From the above results, the organic EL device in which the light emitting layer 104 is formed using the organic EL compound according to the first embodiment and the second embodiment of the present invention has a luminance and luminance half-life as compared with the comparative product. Therefore, it was confirmed that the light emitting characteristics (luminance) and reliability (luminance half-life) were excellent.

（ただし、合成反応上での理論値として、ｍ＝１，ｎ＝２，ｐ＝４，ｑ＝０，ｂ＝２，ｒ＝１であり、分子量ＭＷ＝２７２２である。） [Third Embodiment]
(Compound for organic EL)
As 3rd Embodiment of the compound for organic EL of this invention, the polymer molecule shown to following formula (18) was produced by the synthesis method based on the following synthesis examples.

(However, as theoretical values in the synthesis reaction, m = 1, n = 2, p = 4, q = 0, b = 2, r = 1, and molecular weight MW = 2722.)

<Synthesis Example 9>
A perylene derivative (intermediate) was synthesized by the synthesis method shown in FIG. 16 as follows.
First, 150 cm ³ of dimethylformamide (DMF) dried as a solvent is put into a 500 cm ³ Schlenk tube substituted with Ar, to which 17.18 g (6.45E-2 mol) of Ni (COD) ₂ is added. , 2′-bipyridine (10.08 g, 6.45E-2 mol) and cyclooctadiene (3 cm ³ ) were added, and the mixture was heated at 70 ° C. for 0.5 hour. 0.5 hours later, 10 g (3.23E-2 mol) of 5,6-dibromoacenaphthylene and 9.23 g (3.23E-2 mol) of 1,8-dibromonaphthalene were added thereto and reacted at 90 ° C. It was.
After 5 hours of reaction, the reaction solution was cooled to room temperature and 30 cm ³ added thereto methanol 50 cm ³ of 10% aqueous hydrochloric acid. The precipitate was collected by filtration and washed with sufficient water and methanol.
The filtrate was dissolved in 300 cm ³ of chloroform, and the target product was separated using silica gel. Hexane and toluene were used as developing solvents.
Further purification was carried out by reprecipitation using dichloromethane and hexane.
As a result, 1.5 g (yield 16.8%) of a dark red solid was obtained. Moreover, MS ⁺ : 276 was confirmed.

<Synthesis Example 10>
Bisbromophenyl-benzoindenoperylene was synthesized by the synthesis method shown in FIG. 17 as follows.
First, an Ar-substituted 100 cm ³ Schlenk tube was charged with 1.29 g (4.67E-3 mol) of the perylene intermediate synthesized earlier and 2 g of 1,3-bis-4-bromophenyl-isobenzofuran (4.67E-3 mol). ), And 50 cm ³ of distilled and dried xylene were added and reacted at 130 ° C. for 20 hours.
After the reaction, the mixture was allowed to cool and the precipitated intermediate product was filtered off. The filtered product was washed with 300 cm ³ of heated chloroform, and then the target intermediate was recovered.
As a result, 1.5 g (yield 45%) of a yellow solid as an intermediate was obtained.
Next, 1.5 g of the above intermediate was put into a 300 cm ³ flask, 150 cm ³ of acetic acid was put therein, and heated at 130 ° C. for 1 hour. After heating, the temperature was lowered to 100 ° C., and then 20 cm ^{3 of} 48% HBr aqueous solution was added. After heating for 30 minutes, water was added to recover the solid content.
After the solid content was sufficiently washed with distilled water and methanol, the target product was separated and purified by silica gel chromatography and reprecipitation.
As a result, 0.8 g (yield 54%) of a red solid was obtained. In addition, MS ^{++ 1} : 684 was confirmed.

<Synthesis Example 11>
2-Bromo-9,9-di-n-octylfluorenyl-7-boronic acid was synthesized by the synthesis method shown in FIG. 18 as follows.
First, the Schlenk tube 200 cm ³ was purged with Ar, 2,7-dibromo-9,9-di -n- octylfluorene 4g (7.3E-3mol), and was with sodium dried solution THF100cm ³ was added was . The solution was cooled to -70 ° C. Thereto was added 4.9 cm ³ of a 1.5 mol / l n-butyllithium hexane solution and left for 1 hour. While maintaining cooling, 1.1 g (7.5E-3 mol) of triethyl boronate was added and reacted for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. An appropriate amount of magnesium sulfate was added to the separated THF solution to remove water. After removing magnesium sulfate using a filter paper, hexane was added to precipitate the target product. Purification was performed by a reprecipitation method. As the solvent, THF and hexane were used.

<Synthesis Example 12>
4-Bromo-triphenylaminoboronic acid was synthesized by the synthesis method shown in FIG. 19 as follows.
First, a commercially available 4,4′-dibromo-triphenylamine 4 g (9.9E-3 mol) and sodium-dried THF 100 cm ³ were added to an Ar-substituted 200 cm ³ Schlenk tube to obtain a solution. The solution was then cooled to -70 ° C. Thereto, 9.9 cm ³ (1.48E-2 mol) of a 1.5 mol / l n-butyllithium hexane solution was added and left for 1 hour. Next, 1.9 g (1.3E-2 mol) of triethyl boronate was added while maintaining the cooling state, and the reaction was allowed to proceed for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. Subsequently, an appropriate amount of magnesium sulfate was added to the separated THF solution to remove moisture. After removing magnesium sulfate using a filter paper, hexane was added to precipitate the target product. Purification was performed by a reprecipitation method. Moreover, THF and hexane were used as the solvent.
As a result, 1.4 g (yield 40%) of a white (colored light green) solid was obtained.

<Synthesis Example 13>
1- (4-Bromobenzyl) -4-phenylboronic acid was synthesized by the synthesis method shown in FIG. 20 as follows.
First, the Schlenk tube 200 cm ³ was purged with Ar, 4,4'-bis-bromophenyl methane 5g (1.5E-2mol), and was with sodium dried solution THF50cm ³ was added were. The solution was then cooled to -70 ° C. Thereto was added 10.2 cm ³ (1.5E-2 mol) of a 1.5 mol / l n-butyllithium hexane solution and left for 1 hour. Next, 2.2 g (1.5E-2 mol) of triethyl boronate was added while the cooling state was maintained, and the reaction was performed for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. Subsequently, an appropriate amount of magnesium sulfate was added to the separated THF solution to remove moisture. After removing magnesium sulfate using filter paper, the solvent was removed using an evaporator.
As a result, 4 g of a transparent viscous material was obtained. In this state, it was used for the next reaction.

<Synthesis Example 14>
The third embodiment of the EL material (EL material 3) represented by the above formula (18), that is, the organic EL compound of the present invention was synthesized by the synthesis route shown in FIG.
First, an Ar-substituted 200 cm ³ Schlenk tube was synthesized (Synthesis Example 1) 0.5 g (7.28E-4 mol) of the indenoperylene derivative and 0.54 g of 4-bromo-triphenylaminoboronic acid (1 .46E-3mol) was charged, then distillation of ethanol 50 cm ³ thereto was a solution by adding distilled toluene 100 cm ^3.
Next, 0.06 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and 30 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto, and the mixture was heated at 80 ° C. After 1 hour, 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid 1.5 g (2.91E-3 mol), tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) 0.06 g was added and reacted for 5 hours.
Subsequently, 0.18 g (1.46E-3 mol) of commercially available phenylboronic acid was added and reacted for another 5 hours. After the reaction, air was bubbled into the reaction solution for 30 minutes under heating. Next, after cooling the reaction solution to room temperature, it was transferred to a 1 liter separatory funnel and extracted with toluene, and washed thoroughly with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 0.5 g (yield 25%) of a red solid was obtained. (However, the molecular weight was calculated as 2722.)

（ただし、合成反応上での理論値として、ｍ＝１，ｎ＝２，ｐ＝４，ｑ＝２，ｂ＝２，ｒ＝１であり、分子量ＭＷ＝３０５４である。） [Fourth Embodiment]
As a fourth embodiment of the compound for organic EL of the present invention, a polymer molecule represented by the following formula (19) was produced by a synthesis method based on the following synthesis example.

(However, as theoretical values in the synthesis reaction, m = 1, n = 2, p = 4, q = 2, b = 2, r = 1, and molecular weight MW = 3054.)

<Synthesis Example 15>
The EL material (EL material 4) represented by the above formula (19) was synthesized by the synthesis route shown in FIG.
First, an Ar-substituted 200 cm ³ Schlenk tube was charged with 0.5 g (7.28E-4 mol) of the previously synthesized indenoperylene derivative and 0.54 g (1.46E-3 mol) of 4-bromo-triphenylaminoboronic acid. was charged, then distillation of ethanol 50 cm ³ thereto was a solution by adding distilled toluene 100 cm ^3.
Next, 0.06 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and 30 cm ³ of a saturated aqueous solution of sodium carbonate were added thereto, and the mixture was heated at 80 ° C. One hour later, 0.42 g (1.46E-3 mol) of 1- (4-bromobenzyl) -4-phenylboronic acid and 0.06 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) were added and reacted. I let you. Two hours later, further 1.5 g (2.91E-3 mol) of 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid, tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) 0.06 g was added and reacted for 5 hours.
Subsequently, 0.12 g (1.04E-3 mol) of commercially available phenylboronic acid was added and reacted for another 5 hours. After the reaction, air was bubbled into the reaction solution for 30 minutes under heating. Next, after cooling the reaction solution to room temperature, it was transferred to a 1 liter separatory funnel and subjected to toluene extraction and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 0.4 g (yield 18%) of a red solid was obtained. (However, the molecular weight was calculated as 3054.)

In addition, with respect to each of the above-mentioned synthesis, the following documents were referenced (synthesis references)
J. Am. Chem. Soc. 118, 2374-2379 (1996)
Polymers for Advanced Technologies, 15 (5), 266-269; 2004
Eur. Pat. Appl., 1298117, 02 Apr 2003
Helvetica Chimica Acta, 85 (7), 2195-2213; 2002
Organometallics, 20 (24), 5162-5170; 2001
Journal of Organic Chemistry, 69 (3), 987-990; 2004
Journal of Organic Chemistry, 62 (3), 530-537; 1997

(Examples 7-12, Comparative Examples 1-3)
Next, using the thus obtained organic EL compound of the present invention, the light emitting layer 104 of the organic EL device 100 shown in FIG. 10 was formed as follows.
That is, the material shown in Table 2 below was used as a material for forming the light emitting layer 104.

Here, in Example 7, (EL material 3) represented by the above formula (18) and (host 1) represented by the above formula (15) were used at a mixing ratio (weight ratio) of 1: 8.7. This was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed by the spin coat method as mentioned above, and the organic EL device as an example product was obtained.
In Example 8, (EL material 4) represented by the above formula (19) and (host 1) represented by the above formula (15) were used at a mixing ratio (weight ratio) of 1: 7.6. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 9, (EL material 3) represented by the above formula (18) and (host 2) represented by the above formula (16) were used at a mixing ratio (weight ratio) of 1: 8.7. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 10, (EL material 4) represented by the above formula (19) and (host 2) represented by the above formula (16) were used at a mixing ratio (weight ratio) of 1: 7.6. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 11, (EL material 3) represented by the above formula (18) and (host 3) represented by the above formula (17) were used at a mixing ratio (weight ratio) of 1: 8.7. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 12, (EL material 4) represented by the above formula (19) and (host 3) represented by the above formula (17) were used at a mixing ratio (weight ratio) of 1: 7.6. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.

In Comparative Example 1, only (Host 1) represented by the above formula (15) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.
In Comparative Example 2, only (Host 2) represented by the above formula (16) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.
In Comparative Example 3, only (Host 3) represented by the above formula (17) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.

(Device evaluation)
A voltage was applied to each of the above organic EL devices so that a current of DC 100 mA / cm ² flowed through the light emitting layer 104 to emit light.
EL waveforms are shown in FIGS. FIG. 23 shows EL waveforms of Examples 7, 9, and 11, and FIG. 24 shows EL waveforms of Examples 8, 10, and 12. Regarding the comparative example, as described above, FIG. 13 shows the EL waveform of Comparative Example 1, FIG. 14 shows the EL waveform of Comparative Example 2, and FIG. 15 shows the EL waveform of Comparative Example 3.

Further, the chromaticity, luminance, and luminance half-life (time until the luminance was reduced to half of the initial luminance) were measured, and the results are also shown in Table 2 above.
In Example 7, the applied voltage for obtaining the current was 6.1V.
Similarly, the applied voltage is 6.1 V in Example 8, the applied voltage is 5.9 V in Example 9, the applied voltage is 5.9 V in Example 10, and the applied voltage is 5.8 V in Example 11. In Example 12, the applied voltage was 5.8V. Further, as described above, in Comparative Example 1, the applied voltage was 6.0 V, in Comparative Example 2, the applied voltage was 5.8 V, and in Comparative Example 3, the applied voltage was 5.7 V.

  Based on the above results, the organic EL device in which the light emitting layer 104 is formed using the organic EL compound of the third embodiment and the fourth embodiment of the present invention is also more luminosity and luminance half life than the comparative product. Therefore, it was confirmed that the light emitting characteristics (luminance) and reliability (luminance half-life) were excellent.

（ただし、合成反応上での理論値として、ｍ＝１，ｎ＝２，ｐ＝４，ｑ＝０，ｂ＝２，ｒ＝１であり、分子量ＭＷ＝２５７４である。） [Fifth Embodiment]
(Compound for organic EL)
As a fifth embodiment of the organic EL compound of the present invention, a polymer molecule represented by the following formula (20) was produced by a synthesis method based on the following synthesis example.

(However, as theoretical values in the synthesis reaction, m = 1, n = 2, p = 4, q = 0, b = 2, r = 1, and molecular weight MW = 2574.)

<Synthesis Example 16> (Synthesis of alcohol intermediate)
A 5,12-bis-4bromophenyl-tetracene derivative was synthesized by the synthesis method shown in FIG. 25 as follows.
First, Ar-substituted 500 cm ³ Schlenk tube was charged with 2 g (7.7E-3 mol) of 5,12-tetracenequinone and 100 cm ³ of tetrahydrofuran dried for solvent use, and cooled to -78 ° C. (cooled with dry ice). ). Separately, 4.6 g (1.9E-2 mol) of 1,4-dibromobenzene was weighed and added to a 300 cm ³ Schlenk tube. Thereto, 100 cm ³ of dried tetrahydrofuran as a solvent was added, and cooled to −78 ° C. (cooled with dry ice).
After cooling, 11.3 cm ³ of a 1.5 mol / l n-butyllithium hexane solution was added and left for 1 hour. After being allowed to stand, the Li solution was added to the tetracenequinone solution with a dropper while taking care not to touch the atmosphere. The reaction was continued for 3 hours while continuing the cooling with dry ice, and the reaction was allowed to proceed overnight at room temperature after 3 hours. After the reaction, toluene and distilled water were added and washed thoroughly with a separatory funnel. Thereafter, the organic layer was dried with 5 g of magnesium sulfate, and then the solvent was removed with an evaporator.
Purification was performed by silica gel chromatography and reprecipitation. Toluene was used as a developing solvent in silica gel chromatography. Moreover, reprecipitation was performed using dichloromethane and hexane.
As a result, 3.5 g (84% yield) of a white solid was obtained.

<Synthesis Example 17>
5,12-bis-p-bromophenylnaphthacene was synthesized by the synthesis method shown in FIG. 26 as follows.
First, 3.0 g (5.22E-3 mol) of the previously synthesized alcohol intermediate was weighed and introduced into a 300 cm ³ eggplant flask under the atmosphere. Thereto, 150 cm ³ of acetic acid was weighed and introduced as a solvent. Separately, a solution of tin (II) in hydrochloric acid (35%) (tin chloride: hydrochloric acid = 1: 1 (weight ratio)) was prepared, and 20 cm ³ was added to the acetic acid solution of the alcohol intermediate. After reacting at room temperature for 3 hours, toluene was added, and the mixture was sufficiently washed with distilled water using a separatory funnel. After sufficiently washing, the organic layer was dried with 5 g of magnesium sulfate, and then the solvent was removed with an evaporator.
Purification was performed by silica gel chromatography and reprecipitation. As a developing solvent in silica gel chromatography, a mixed solution of toluene and hexane (toluene: hexane = 1: 2) was used. Moreover, reprecipitation was performed using dichloromethane and hexane.
As a result, 2.3 g (yield 82%) of a white solid was obtained.

<Synthesis Example 18>
2-Bromo-9,9-di-n-octylfluorenyl-7-boronic acid was synthesized by the synthesis method shown in FIG. 27 as follows.
First, the Schlenk tube 200 cm ³ was purged with Ar, 2,7-dibromo-9,9-di -n- octylfluorene 4g (7.3E-3mol), and was with sodium dried solution THF100cm ³ was added was . The solution was cooled to -70 ° C. Thereto was added 4.9 cm ³ of a 1.5 mol / l n-butyllithium hexane solution, and the mixture was allowed to stand for 1 hour. While maintaining cooling, 1.1 g (7.5E-3 mol) of triethyl boronate was added and reacted for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. An appropriate amount of magnesium sulfate was added to the separated THF solution to remove water. After removing magnesium sulfate using a filter paper, hexane was added to precipitate the target product.
Purification was performed by a reprecipitation method. As the solvent, THF and hexane were used.

<Synthesis Example 19>
4-Bromo-triphenylaminoboronic acid was synthesized by the synthesis method shown in FIG. 28 as follows.
First, 4 g (9.9E-3 mol) of commercially available 4,4′-dibromo-triphenylamine and 100 cm ³ of THF dried with sodium were added to an Ar-substituted 200 cm ³ Schlenk tube to obtain a solution. The solution was then cooled to -70 ° C. Thereto, 9.9 cm ³ (1.48E-2 mol) of a 1.5 mol / l n-butyllithium hexane solution was added and left for 1 hour. Next, 1.9 g (1.3E-2 mol) of triethyl boronate was added while maintaining the cooling state, and the reaction was allowed to proceed for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. Subsequently, an appropriate amount of magnesium sulfate was added to the separated THF solution to remove moisture. After removing magnesium sulfate using a filter paper, hexane was added to precipitate the target product. Purification was performed by a reprecipitation method. Moreover, THF and hexane were used as the solvent.
As a result, 1.4 g (yield 40%) of a white (colored light green) solid was obtained.

<Synthesis Example 20>
1- (4-Bromobenzyl) -4-phenylboronic acid was synthesized by the synthesis method shown in FIG. 5 as follows.
First, the Schlenk tube 200 cm ³ was purged with Ar, 4,4'-bis-bromophenyl methane 5g (1.5E-2mol), and was with sodium dried solution THF50cm ³ was added were. The solution was then cooled to -70 ° C. Thereto was added 10.2 cm ³ (1.5E-2 mol) of a 1.5 mol / l n-butyllithium hexane solution and left for 1 hour. Next, 2.2 g (1.5E-2 mol) of triethyl boronate was added while keeping the cooling state, and the reaction was performed for 1.5 hours. After the reaction, 5 cm ³ of 40% HCl aqueous solution was added to the reaction solution at 5 ° C. After 1 hour, the solution was neutralized with a saturated aqueous sodium carbonate solution to a pH of 7.
Next, the organic layer (THF layer) was separated using a separatory funnel. Subsequently, an appropriate amount of magnesium sulfate was added to the separated THF solution to remove moisture. After removing magnesium sulfate using filter paper, the solvent was removed using an evaporator.
As a result, 4 g of a transparent viscous material was obtained. In this state, it was used for the next reaction.

<Synthesis Example 21>
The fifth embodiment of the EL material (EL material 5) represented by the above formula (20), that is, the organic EL compound of the present invention was synthesized by the synthesis route shown in FIG.
First, an Ar-substituted 200 cm ³ Schlenk tube was synthesized (Synthesis Example 1) tetracene derivative 0.5 g (9.29E-4 mol), 4-bromo-triphenylaminoboronic acid 0.68 g (1.86E). -3Mol) was charged, then distillation of ethanol 50 cm ³ thereto was a solution by adding distilled toluene 100 cm ^3.
Next, 0.1 cm of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and a saturated aqueous solution of sodium carbonate were added thereto at 30 cm ³ and heated at 80 ° C. After 1 hour, 1.9 g (3.72E-3 mol) of 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid, tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) 0.1 g was added and reacted for 5 hours.
Subsequently, 0.23 g (1.86E-3 mol) of commercially available phenylboronic acid was added and reacted for another 5 hours. After the reaction, air was bubbled into the reaction solution for 30 minutes under heating. Next, after the reaction solution was cooled to room temperature, it was transferred to a 1 liter separatory funnel and subjected to toluene extraction, and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for the reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 0.52 g (yield 22%) of a yellow solid was obtained. (However, the molecular weight was calculated as 2574.)

（ただし、合成反応上での理論値として、ｍ＝１，ｎ＝２，ｐ＝４，ｑ＝２，ｂ＝２，ｒ＝１であり、分子量ＭＷ＝２９０６である。） [Sixth Embodiment]
As a sixth embodiment of the compound for organic EL of the present invention, a polymer molecule represented by the following formula (21) was produced by a synthesis method based on the following synthesis example.

(However, as theoretical values in the synthesis reaction, m = 1, n = 2, p = 4, q = 2, b = 2, r = 1, and molecular weight MW = 2906.)

<Synthesis Example 22>
The EL material (EL material 6) represented by the above formula (21) was synthesized by the synthesis route shown in FIG.
First, an Ar-substituted 200 cm ³ Schlenk tube was synthesized (Synthesis Example 1) 0.5 g (9.29E-4 mol) of a tetracene derivative and 0.68 g (1.86E) of 4-bromo-triphenylaminoboronic acid. -3Mol) was charged, then distillation of ethanol 50 cm ³ thereto was a solution by adding distilled toluene 100 cm ^3.
Next, 0.1 cm of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) and a saturated aqueous solution of sodium carbonate were added thereto at 30 cm ³ and heated at 80 ° C. After 1 hour, 0.54 g (1.86E-3 mol) of 1- (4-bromobenzyl) -4-phenylboronic acid and 0.07 g of tetrakistriphenylphosphine palladium complex (Pd (PPh ₃ ) ₄ ) were added and reacted. I let you. After 2 hours, further, 1.91 g (3.72E-3 mol) of 2-bromo-9,9-di-n-octylfluorenyl-7-boronic acid, hexakistriphenylphosphine palladium complex (Pd (PPh ₃ )) ₄ ) 0.1 g was added and reacted for 5 hours.
Subsequently, 0.23 g (1.86E-3 mol) of commercially available phenylboronic acid was added and reacted for another 5 hours. After the reaction, air was bubbled into the reaction solution for 30 minutes under heating. Next, after the reaction solution was cooled to room temperature, it was transferred to a 1 liter separatory funnel and subjected to toluene extraction, and thoroughly washed with distilled water. The toluene layer in the separatory funnel was sufficiently dried with magnesium sulfate, and then purified using silica gel chromatography and reprecipitation.
The solvent used for the reprecipitation purification is a system using dichloromethane / hexane and a system using dichloromethane / methanol.
As a result, 0.54 g (yield 20%) of a yellow solid was obtained. (However, the molecular weight was calculated as 2906.)

For each of the above syntheses, the following documents were referenced.
(Synthetic Reference)
Polymers for Advanced Technologies, 15 (5), 266-269; 2004
Eur. Pat. Appl., 1298117, 02 Apr 2003
Helvetica Chimica Acta, 85 (7), 2195-2213; 2002
Organometallics, 20 (24), 5162-5170; 2001
Journal of Organic Chemistry, 69 (3), 987-990; 2004
Journal of Organic Chemistry, 62 (3), 530-537; 1997
Journal of the American Chemical Society (1963), 85 (11), 1561-4.

(Examples 13-18, Comparative Examples 1-3)
Next, using the thus obtained organic EL compound of the present invention, the light emitting layer 104 of the organic EL device 100 shown in FIG. 10 was formed as follows.
That is, the materials shown in Table 3 below were used as the material for forming the light emitting layer 104.

Here, in Example 13, (EL material 5) represented by the above formula (20) and (host 1) represented by the above formula (15) were used at a mixing ratio (weight ratio) of 1: 6.35. This was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed by the spin coat method as mentioned above, and the organic EL device as an Example product was obtained.
In Example 14, (EL material 6) represented by the above formula (21) and (host 1) represented by the above formula (15) were used at a mixing ratio (weight ratio) of 1: 5.51, and this was used. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 15, (EL material 5) represented by the above formula (20) and (host 2) represented by the above formula (16) were used at a mixing ratio (weight ratio) of 1: 6.35. Was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 16, (EL material 6) represented by the above formula (21) and (host 2) represented by the above formula (16) were used at a mixing ratio (weight ratio) of 1: 5.51, and this was used. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 17, (EL material 5) represented by the above formula (20) and (host 3) represented by the above formula (17) were used at a mixing ratio (weight ratio) of 1: 6.35. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.
In Example 18, (EL material 6) represented by the above formula (21) and (host 3) represented by the above formula (17) were used at a mixing ratio (weight ratio) of 1: 5.51, and this was used. A solution (ink) having a solid content of 1.5 wt% was obtained by dissolving in chloroform. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as an Example product was obtained.

In Comparative Example 1, only (Host 1) represented by the above formula (15) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.
In Comparative Example 2, only (Host 2) represented by the above formula (16) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.
In Comparative Example 3, only (Host 3) represented by the above formula (17) was used, and this was dissolved in chloroform to obtain a solution (ink) having a solid content of 1.5 wt%. And using this solution (ink), the light emitting layer 104 was formed as mentioned above, and the organic EL device as a comparative example product was obtained.

(Device evaluation)
A voltage was applied to each of the above organic EL devices so that a current of DC 100 mA / cm ² flowed through the light emitting layer 104 to emit light.
The EL waveforms are shown in FIGS. 32 shows the EL waveforms of Examples 13, 15, and 17, and FIG. 33 shows the EL waveforms of Examples 14, 16, and 18. Regarding the comparative example, as described above, FIG. 13 shows the EL waveform of Comparative Example 1, FIG. 14 shows the EL waveform of Comparative Example 2, and FIG. 15 shows the EL waveform of Comparative Example 3.

Further, the chromaticity, luminance, and luminance half-life (time until the luminance is reduced to half of the initial luminance) were measured, and the results are also shown in Table 3 above.
In Example 13, the applied voltage for obtaining the current was 6.3V.
Similarly, the applied voltage is 6.3 V in Example 14, the applied voltage is 6.1 V in Example 15, the applied voltage is 6.1 V in Example 16, and the applied voltage is 5.8 V in Example 17. In Example 18, the applied voltage was 5.8V. Further, as described above, in Comparative Example 1, the applied voltage was 6.0 V, in Comparative Example 2, the applied voltage was 5.8 V, and in Comparative Example 3, the applied voltage was 5.7 V.

From the above results, the organic EL device in which the light emitting layer 104 is formed using the organic EL compound of the fifth embodiment and the sixth embodiment of the present invention also has a luminance and luminance half-life compared to the comparative product. Therefore, it was confirmed that the light emitting characteristics (luminance) and reliability (luminance half-life) were excellent.
Therefore, in the organic EL of the present invention, the vice has higher light emission efficiency and longer life than conventional ones.

6 is a diagram illustrating a synthesis method of Synthesis Example 1. FIG. 6 is a diagram illustrating a synthesis method of Synthesis Example 2. FIG. 6 is a diagram illustrating a synthesis method of Synthesis Example 3. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 4. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 5. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 6. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 7. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 8. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 8. FIG. It is a schematic block diagram of one Embodiment of the organic EL device of this invention. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. 10 is a diagram illustrating a synthesis method of Synthesis Example 9. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 10. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 11. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 12. FIG. 14 is a diagram illustrating a synthesis method of Synthesis Example 13. FIG. 14 is a diagram illustrating a synthesis method of Synthesis Example 14. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 15. FIG. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. 10 is a diagram illustrating a synthesis method of Synthesis Example 16. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 17. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 18. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 19. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 20. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 21. FIG. 10 is a diagram illustrating a synthesis method of Synthesis Example 22. FIG. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit. It is a graph which shows the EL waveform obtained by making an organic EL device light-emit.

Explanation of symbols

  DESCRIPTION OF SYMBOLS 100 ... Organic EL device, 101 ... Translucent substrate, 102 ... Anode (pixel electrode), 103 ... Hole injection / transport layer, 104 ... Light emitting layer, 105 ... Cathode, 200 ... Sealing material, 201 ... Sealing substrate

Claims (14)

A compound for organic EL as a light emitting material used in an organic EL device,
The compound for organic EL which consists of a polymer molecule | numerator which has as a structural unit the luminescent molecule | numerator which determines the luminescent color area | region of the said luminescent material, and the molecule | numerator shown by following formula (1)-Formula (4).

(However, R represents an alkyl group, an aryl group, or an alkylaryl group.)

(However, R ′ represents hydrogen, an alkyl group, or an alkylaryl group.) The compound for organic EL according to claim 1, wherein the light emitting molecule is one selected from molecules represented by the following formulas (5) to (7).

The organic EL compound according to claim 2, wherein the polymer molecule is represented by the following formula (8).

(However, A represents one selected from the groups represented by the following formulas (9) to (11), R represents an alkyl group, an aryl group, or an alkylaryl group, and R ′ represents hydrogen, an alkyl group, or Represents an alkylaryl group, m, n and p each represents an integer of 1 or more, q and b represent an integer of 0 or more, and r represents an integer of 1 or more.)

In the oligomer unit represented by the above formula (8),
4. The organic EL compound according to claim 3, wherein the integer m representing the number of units represented by A, which is a light emitting unit, is 1 or 2.   In the oligomer unit represented by the above formula (8), an integer n representing the number of units represented by the above formula (1), which is a unit having a hole trap function, is 2 or more. The compound for organic EL as described in any one of.   In the oligomer unit represented by the above formula (8), an integer p representing the number of units represented by the above formula (2), which functions as a connecting unit for increasing the molecular weight and has a function as an electron trap, It is 1 thru | or 4, The compound for organic EL as described in any one of Claims 3-5 characterized by the above-mentioned.   In the structure of the oligomer unit represented by the above formula (8), at least one unit of the unit represented by the above A and the unit represented by the above formula (1) is directly connected. The compound for organic EL as described in any one of these.   The organic EL device using the compound for organic EL as described in any one of Claims 1-7.   The organic EL device which used the compound for organic EL as described in any one of Claims 1-7 for the light emitting layer.   The organic EL device which used the compound for organic EL as described in any one of Claims 1-7 as a light emission dopant material in a light emitting layer. The light emitting layer is formed of the light emitting dopant material and the host material,
The light-emitting dopant and the host material in the light-emitting layer are in such a ratio that the k value in weight% represented by the following formula (12) is 0.5 wt% or more and 10.0 wt% or less. The organic EL device according to claim 10, which is contained.
k = (a / (b + c)) × 100 (12)
(However, a in the formula (12) is a weight occupied by the unit composed of the light emitting molecule in the light emitting dopant material, b is a weight of the light emitting dopant material used, and c is used. The weight of the host material.) The light emitting layer is formed of the light emitting dopant material and the host material,
The organic EL device according to claim 10 or 11, wherein the host material is a homopolymer or a copolymer made of at least one material selected from fluorene, arylamine, and anthracene.   The organic EL device according to any one of claims 9 to 12, wherein at least one hole injection layer or hole transport layer is provided between the light emitting layer and the anode.   The organic EL device according to any one of claims 9 to 13, wherein the light emitting layer is formed by applying by a spin coating method or a droplet discharge method.

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