JP6214026B2 - ORGANIC LIGHT EMITTING MATERIAL, ORGANIC LIGHT EMITTING MATERIAL MANUFACTURING METHOD, AND ORGANIC LIGHT EMITTING DEVICE - Google Patents

Description

  The present invention relates to an organic light emitting material, a method for producing the organic light emitting material, and an organic light emitting element. In particular, when a film is formed, an organic light-emitting material excellent in horizontal orientation and the like (hereinafter sometimes referred to as an oriented light-emitting material), a method for producing such an organic light-emitting material, and such an organic light-emitting material The present invention relates to an organic light emitting device using as a host material or an electron transport material.

Conventionally, as an attempt to improve the light emission efficiency of an organic electroluminescence device (organic EL device), it has been proposed to use phosphorescence instead of fluorescence.
That is, in the light emitting layer of the organic EL element, a high amount of phosphorescent light emitting material is included with respect to the main component host material, and high emission efficiency is achieved by mainly using the excited triplet state of the phosphorescent light emitting material. Expected to be. This is because when an electron and a hole are recombined in an organic EL element, an excited singlet state and an excited triplet state having different spin multiplicity are generated at a ratio of 1: 3. Because.
Therefore, when using fluorescence that is light emission when returning from the excited singlet state to the ground state, only about 25% of the exciton (100%) can be used, whereas the excited triplet state is changed to the ground state. When using phosphorescence, which is light emission when returning, many excitons can be used. That is, by causing intersystem crossing, it can be changed to an exciton that emits phosphorescence, so that the excited singlet state changes to an excited triplet state, and 100% of the exciton can be used. Improvement in luminous efficiency is expected.

Thus, in order to improve the light emission efficiency in this way, an organic EL element having a light emitting layer formed by doping a carbazole compound as a host material and doping a phosphorescent iridium complex material has been proposed (for example, patents). Reference 1).
More specifically, it is an organic EL device in which an anode, a light emitting layer containing a phosphorescent iridium complex material, an electron transport layer made of an organic compound, and a cathode are sequentially stacked, An organic EL device comprising an iridium complex material in a range of 0.5 to 8% by weight using a carbazole compound as a host material.
As a typical phosphorescent iridium complex material, tris (2-phenylpyridine) iridium (hereinafter sometimes referred to as Ir (PPY) ₃ ) represented by the following formula (A) is disclosed. Yes.

In addition, a phosphorescent organometallic complex having a predetermined structure and a light-emitting element containing the same in a light-emitting layer have been proposed in order to improve the light-emitting characteristics and the lifetime of the element (for example, see Patent Document 2).
More specifically, β-dicarbonyl at the end of the long carbon chain represented by the following formula (B) and two 2-phenylpyridine molecules are coordinated to a platinum atom or the like, and the carbon chain There has been proposed a light-emitting element (organic EL element) in which β-dicarbonyl at the other end is a phosphorescent organometallic complex having a similar coordination structure and is contained in a light-emitting layer.

On the other hand, a high-efficiency, long-life organic light-emitting device using a predetermined fluorine-containing triphenylamine compound as a dopant material and a predetermined host material has been proposed (for example, see Patent Document 3). .
More specifically, a fluorine-containing triphenylamine compound represented by the following formula (C) is used as a dopant material in the light emitting layer, and a fluorene compound represented by the following formula (D) or (E) is used as a host material. It is an organic light emitting element characterized by using.

JP 2001-313178 A (Claims etc.) JP 2007-277170 A (Claims etc.) Japanese Patent No. 4311707 (claims, etc.)

However, both the phosphorescent iridium complex material disclosed in Patent Document 1 and the phosphorescent organometallic complex disclosed in Patent Document 2 have insufficient horizontal orientation when formed into films, respectively. Since the transition moments are not uniform, there has been a problem that a phosphorescent light emitting device having high luminance cannot be obtained yet.
In addition, when the phosphorescent iridium complex material disclosed in Patent Document 1 and the phosphorescent organometallic complex disclosed in Patent Document 2 are used in the light emitting layer of the organic EL element, respectively, as host materials There was also a problem that the range of addition amount that can be blended with the carbazole compound was narrow.

Furthermore, the fluorine-containing triphenylamine compound disclosed in Patent Document 3 is used as a dopant material, and there has been a problem that the light emission efficiency is still low.
In addition, the organic light-emitting material disclosed in Patent Document 3 must use a predetermined fluorene compound as a host material, which increases the cost of the resulting organic light-emitting material and is disadvantageous economically. It was seen.
In addition, when the methyl group is introduced into the para position of the terminal phenyl group as in the organic light-emitting material disclosed in Patent Document 3, the amorphous property of the thin film made of organic molecules tends to be remarkably lowered. Although it is suitable for use as a host material, it has been conventionally considered disadvantageous for use as a host material.

Therefore, in view of the circumstances as described above, the present inventors show good horizontal orientation and the like when a film is formed by introducing a predetermined donor-acceptor structure in the molecule. When used as a host material of a light emitting material, a relatively high current value can be obtained even when a low voltage is applied, and a high external quantum efficiency (EQE) can be obtained. The present invention has been completed by finding that exciton blocking characteristics can be obtained.
That is, an object of the present invention is to enable an organic light-emitting material exhibiting good horizontal orientation, an efficient manufacturing method of such an organic light-emitting material, and a low-voltage drive using such an organic light-emitting material. An organic light emitting device is provided.

According to the present invention, a carbazolyl group represented by the following general formula (1) has an electron acceptor tetrafluoroarylene structure at a central site and an electron donor arylene group at both ends thereof. , have a donor-acceptor-type molecular structure comprising, and, characterized in that a value within the range of -0.5 to 0.2 orders parameters calculated from the anisotropy of the extinction coefficient The organic light-emitting material is provided, and the above-described problems can be solved.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom. )

That is, by having a donor-acceptor type molecular structure in the molecule, excellent horizontal orientation and the like can be obtained when the film is formed.
Therefore, when such an organic light emitting material is used as a host material in a light emitting layer of an organic EL element (phosphorescent light emitting element), a relatively high current value can be obtained even when a low voltage is applied. Can obtain high external quantum efficiency (EQE) even in a low current density region.
In addition, carbazolyl groups present at both ends are considered to improve the amorphous properties, respectively, and such an organic light-emitting material can effectively suppress crystallization of the host material as a whole, Even if the blending amount is relatively wide, it is possible to obtain an effect that the mixture can be uniformly mixed and dispersed.
Moreover, when such an organic light emitting material is used as an electron transport material in the electron transport layer of an organic EL element, the exciton generated in the light emitting layer can be prevented from moving, and a high exciton blocking effect can be obtained. Can do.
In addition, by restricting the predetermined substituents to hydrogen atoms in this way, it becomes easier to produce, and as a result, an organic light-emitting material with low cost and stable characteristics can be obtained.
Furthermore, by defining and configuring the order parameters in this way, it is possible to quantitatively manage the horizontality of the organic light emitting material. As a result, when a predetermined organic light emitting element is configured, it is driven at a low voltage. It is possible to achieve a long life and efficiency.
The donor-acceptor type molecular structure is basically composed of an electron donor carbazolyl group, an electron acceptor tetrafluoroarylene structure, and an electron donor carbazolyl group, which are sequentially arranged. A carbazolyl group linked to the end of the donor arylene group can be considered as one electron donor structure.
That is, it can be considered that an arylene group including an electron donor carbazolyl group, an electron acceptor tetrafluoroarylene structure, and an arylene group including an electron donor carbazolyl group are sequentially arranged.

Further, in configuring the organic light emitting material of the present invention, in a three-dimensional space composed of XYZ axes, when the angle formed by the Z axis that is the vertical axis and the virtual axis direction of the molecules of the organic light emitting material is θ, The horizontal angle (θ2) represented by ( 90 ° −θ) is preferably set to a value of 31 ° or less.
By defining the horizontal angle in this way, the horizontality of the organic light emitting material can be managed quantitatively. As a result, when a predetermined organic light emitting element is configured, a low voltage is applied. However, since a relatively high current value can be obtained, it is possible to extend the life and efficiency.

Further, in constituting the organic light emitting material of the present invention, the electron mobility is preferably 1 × 10 ⁻⁸ cm ² / V · s or more at an electric field strength of 1.0 × 10 ⁶ V / cm.
By configuring in this way, the organic light emitting material has an excellent electron transporting ability. Therefore, when a predetermined organic light emitting element is configured, it is possible to drive at a low voltage, thereby extending the life and efficiency. Can be planned.

In constituting the organic light emitting material of the present invention, the triplet energy is preferably 2.0 eV or more.
By comprising in this way, the exciton blocking characteristic of organic luminescent material becomes higher, and it can be used conveniently also as a host material and an electron transport material.
In the present invention, the triplet energy means an energy difference between the lowest excited triplet state and the ground state.

Moreover, another aspect of the present invention is represented by the following general formula (1), and an electron acceptor tetrafluoroarylene structure is formed in the central portion, and both ends thereof are bonded via an electron donor arylene group. possess a carbazolyl group, respectively, a donor-acceptor-type molecular structure comprising, and a value in the range of -0.5 to 0.2 orders parameters calculated from the anisotropy of the extinction coefficient A first step of preparing an aryl halide comprising 1,4-dihalogenated tetrafluoroarylene, and a carbazolylphenylboronic acid ester having substituents R ^{1 to} R ^2. A first boronic acid ester and a second boronic acid ester each comprising a carbazolylphenyl boronic acid ester having substituents R ^{3 to} R ⁴ are prepared. After the two steps, the halogen at one terminal of the aryl halide and the first boronic ester are cross-coupled by the action of a palladium catalyst and a base nucleophile, the other terminal of the other aryl halide And a third step of cross-coupling the halogen and the second boronic acid ester by the action of a palladium catalyst and a base nucleophilic species.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom. )

By carrying out like this, when forming into a film, the predetermined organic luminescent material excellent in horizontal orientation etc. can be manufactured efficiently.
Therefore, when such an organic light-emitting material is used as a host material of a light-emitting layer in an organic EL element, a relatively high current value can be obtained even when a low voltage is applied. However, high external quantum efficiency (EQE) can be obtained. Moreover, when it uses as an electron transport material of an electron carrying layer, a high exciton blocking effect can be acquired.
When the types of the substituents R ^{1 to} R ^{2 and} the types of the substituents R ^{3 to} R ⁴ are different, that is, an organic light-emitting material having an asymmetric structure, or the types of the substituents R ^{1 to} R ² and When the types of the substituents R ^{3 to} R ⁴ are the same, that is, even if the organic light emitting material has a symmetric structure, it can be efficiently produced, for example, in two steps.

In carrying out the method for producing an organic light-emitting material of the present invention, in the third step, the first boronic ester and the second boronic ester are added dropwise to the aryl halide while cross-cups are added. It is preferable to ring.
When implemented in this way, even when the activity of the boronic acid ester is short, fresh boronic acid ester is always supplied by dripping. Therefore, the boronic acid ester is effectively used for cross-coupling. A predetermined organic light-emitting material can be efficiently manufactured, both symmetrically and asymmetrically.
That is, by carrying out in this way, a predetermined boronic acid ester can be effectively reacted even with an aryl halide considered to have a strong electron acceptor property and a very low reactivity such as Suzuki coupling. The yield of the predetermined organic light emitting material can be dramatically improved.

Still another embodiment of the present invention is represented by the following general formula (1 ′), wherein an electron acceptor tetrafluoroarylene structure is formed at the central portion, and an electron donor arylene group is interposed at both ends thereof. Te, possess a carbazolyl group, respectively, a donor-acceptor-type molecular structure comprising, and, within the range of -0.5 to 0.2 orders parameters calculated from the anisotropy of the extinction coefficient And a first step of preparing an aryl halide comprising 1,4-dihalogenated tetrafluoroarylene, and substituents R ^{1 to} R ² or substituents R ^{3 to} R ^4. A second step of preparing a boronic acid ester comprising a carbazolylphenylboronic acid ester having an aryl halide, an aryl halide, and a boronic acid ester; By the action, the method of manufacturing the organic light-emitting material, characterized in that it comprises a third step of cross-coupling, a.

(In the general formula (1 ′), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom. )

By carrying out in this way, even when the activity life of the boronic acid ester is short, a fresh boronic acid ester is always supplied by dripping, so the boronic acid ester is effectively used for cross-coupling. Thus, a symmetrical organic light emitting material can be efficiently produced.
That is, a predetermined boronic acid ester can be effectively reacted even with an aryl halide considered to have a strong electron acceptor property and extremely low reactivity, and the yield of a predetermined organic light emitting material can be drastically increased. Can be improved.

Moreover, when implementing the manufacturing method of the organic luminescent material of this invention, it is preferable to make it cross-couple in 3rd process, dripping boronic acid ester with respect to aryl halide.
When implemented in this way, even when the activity of the boronic acid ester is short, fresh boronic acid ester is always supplied by dripping. Therefore, the boronic acid ester is effectively used for cross-coupling. A predetermined organic light emitting material can be efficiently manufactured.
That is, by carrying out in this way, a predetermined boronic acid ester can be effectively reacted even with an aryl halide considered to have a strong electron acceptor property and a very low reactivity such as Suzuki coupling. The yield of the predetermined organic light emitting material can be dramatically improved.

Further, another aspect of the present invention is represented by the following general formula (1): an electron acceptor tetrafluoroarylene structure at a central site, and an electron donor arylene group at both ends thereof. , possess a carbazolyl group, respectively, a donor-acceptor-type molecular structure comprising, and, within a range of -0.5 to 0.2 orders parameters calculated from the anisotropy of the extinction coefficient An organic light-emitting element comprising a light-emitting layer formed by using the organic light-emitting material described above as a host material and a dopant material added thereto.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom. )

  With such a configuration, an organic light emitting device that can obtain a relatively high current value even when a low voltage is applied, and that can obtain a high external quantum efficiency (EQE) even in a low current density region. Can be obtained.

Further, another aspect of the present invention is represented by the following general formula (1): an electron acceptor tetrafluoroarylene structure at a central site, and an electron donor arylene group at both ends thereof. , possess a carbazolyl group, respectively, a donor-acceptor-type molecular structure comprising, and, within a range of -0.5 to 0.2 orders parameters calculated from the anisotropy of the extinction coefficient An organic light emitting device comprising an electron transport layer including the organic light emitting material as an electron transport material.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom. )

  By comprising in this way, the said electron transport material can block | prevent the movement of the exciton produced | generated within the light emitting layer efficiently, and can obtain the high exciton blocking effect.

FIGS. 1A to 1F are diagrams for explaining the effect of introducing a donor / acceptor structure in a horizontally oriented organic light emitting material. FIGS. 2A to 2B are views for explaining the alignment state in the non-horizontal alignment organic light emitting material (CBP). FIG. 3 is a diagram for explaining the relationship between the anisotropy of the extinction coefficient (k) and the wavelength (λ) of the horizontally oriented organic light emitting material (Example 1). FIG. 4 is a diagram for explaining the relationship between the electric field and the electron mobility of the horizontally oriented organic light emitting material (Example 1) and the non-horizontal oriented organic light emitting material (Comparative Example 1). FIGS. 5A to 5D are emission spectra for measuring triplet energy of a horizontally oriented organic light emitting material (Example 1). FIGS. 6A to 6B are cross-sectional views of basic organic EL elements. FIG. 7 is a JV plot of an organic EL device using a horizontally oriented organic light emitting material (Example 1) and a non-horizontal oriented organic light emitting material (mCP) as host materials. FIG. 8 illustrates the relationship between the external quantum efficiency and the current density of an organic EL device using a horizontally oriented organic light emitting material (Example 1) and another organic light emitting material (Alq3) as an electron transport material. FIG. FIG. 9 is an NMR chart of a horizontally oriented organic light emitting material (Example 1). FIG. 10 is an FT-IR chart of a horizontally oriented organic light emitting material (Example 1). FIG. 11A is an ultraviolet absorption spectrum of the horizontally oriented organic light emitting material (Example 1), and FIG. 11B is a fluorescence emission spectrum of the horizontally oriented organic light emitting material (Example 1). is there. FIG. 12 (a) shows the current density and the external in the case where a device is configured by including a horizontally oriented organic light emitting material (Example 1) in the light emitting layer as a host material and in the electron transport layer as an electron transport material. FIG. 12B is a diagram for explaining the relationship between the quantum efficiency and the relationship between the applied voltage and the current density when the device is configured.

[First Embodiment]
A first embodiment of the present invention is represented by the following general formula (1), and an electron acceptor tetrafluoroarylene structure is formed at a central site, and both ends thereof are bonded via an electron donor arylene group. It is an organic light emitting material characterized by having a donor-acceptor type molecular structure each containing a carbazolyl group.

(In the general formula (1), the substituents R ^{1 to} R ⁴ and a to h are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon. An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or an amino group.)

  Hereinafter, the aspect of the organic light-emitting material according to the first embodiment of the present invention will be specifically described with reference to the drawings as appropriate.

1. Basic Structure The organic light-emitting material according to the first embodiment is a compound represented by the above general formula (1), and includes an electron acceptor tetrafluoroarylene structure at a central site, and electron donor properties at both ends thereof. Each of which contains a carbazolyl group via the arylene group.
That is, by having a predetermined donor-acceptor type molecular structure in the molecule of the organic light emitting material as a basic structure, the horizontal orientation of the molecule when the film is formed can be remarkably improved.

The donor-acceptor molecular structure of the present invention will be described more specifically with reference to FIGS. 1A to 1F. The organic light-emitting material 10 of the present invention shown in FIG. In addition, when having a predetermined donor-acceptor type molecular structure 10 ′ (10a, 10b, 10a), when arranged in layers in the vertical direction, as shown in FIG. 1 (d), a benzene-perfluorobenzene type This causes the stacking phenomenon.
More specifically, assuming a plurality of molecules positioned in the vertical direction, as shown on the left side of the arrow in FIG. 1 (c), an arylene group (10a, 10a ′) having a donor property of a lower molecule, As shown in FIG. 1 (d), the electron acceptor tetrafluoroarylene structure (10b) of the molecule is close to each other, and the one arylene structure is relatively separated in the horizontal direction, and is electrically attracted in the vertical direction. It becomes a relationship. Accordingly, as shown on the right side of the arrow in FIG. 1C, the upper molecules are easily arranged in the horizontal direction due to the influence of the lower molecules already formed in the horizontal direction.
Furthermore, as shown on the left side of the arrow in FIG. 1 (e), when assuming a plurality of molecules positioned in the vertical direction and assuming that a plurality of upper molecules exist, donor properties can be obtained even between a plurality of upper molecules. It is presumed that the arylene group having the above and the electron acceptor tetrafluoroarylene structure of the upper molecule are close to each other and are layered.
Then, as shown on the right side of the arrow in FIG. 1 (e), such a layered molecule composed of a plurality of molecules is easier to arrange in the horizontal direction, and once aligned in the horizontal direction, It becomes difficult to move.
Therefore, when an organic light-emitting material having a donor-acceptor type molecular structure having horizontal orientation is used as a host material, the molecule 10 having the donor-acceptor type molecular structure 10 ′ is easily fixed and arranged in the horizontal direction. As shown in FIG. 1 (f), it can be concluded that even when a dopant material or the like is present, the dopant material or the like is also easily arranged in the horizontal direction, so that the movement of charges between molecules becomes smooth.

Although not shown, the organic light emitting material as the host material not only defines itself, but also regulates the molecular arrangement of the dopant material contained in the light emitting layer to some extent, and improves the horizontal orientation of these materials together. It is estimated that
Therefore, when the organic light emitting material as the host material of the present invention is excited to emit light, the light emission traveling direction is aligned in a predetermined direction (the normal direction of the thin film), that is, the transition moment is aligned. Therefore, it is estimated that even higher emission luminance can be stably obtained even in the low current density region.

In contrast, 4,4′-dicarbazolyl-1,1′biphenyl, which is a non-horizontal organic light-emitting material whose structural formula is shown in FIG. (Hereinafter sometimes referred to as CBP) has a biphenylene structure 30 'in the molecule, but is not a predetermined donor-acceptor type molecular structure. Therefore, the above-described benzene-perfluorobenzene type interaction does not exist, and a plurality of molecules 30 are randomly oriented as shown in FIG.
Therefore, when a non-horizontal alignment organic light-emitting material is used as a host material, even if a plurality of molecules are arranged in the horizontal direction once due to the dopant material or the like, the fixability in the vertical direction or the horizontal direction is Since it is insufficient, a case of moving in the vertical direction is sufficiently assumed.
That is, it is presumed that it is difficult to obtain sufficient charge mobility because the movement of charge between molecules is not as smooth as that of molecules having horizontal orientation.

2. Type Specific examples of the compound represented by the general formula (1) include compounds represented by the following formulas (3) to (7).
The compounds 1,4-bis {4- (9H-carbazol-9-yl) phenyl} -2,3 represented by the following formula (3), wherein the substituents R ^{1 to} R ⁴ are each a hydrogen atom: , 5,6-tetrafluorobenzene (hereinafter sometimes referred to as CPFP) is more preferred.
This is because the compound represented by the following formula (3) is easier to produce, and as a result, an organic light-emitting material having low cost and stable characteristics can be obtained.

3. Horizontal orientation 1 (order parameter (S))
Further, as described above, the organic light emitting material represented by the general formula (1) is arranged in the horizontal direction with respect to the surface of the base material when the film is formed on the base material, that is, good horizontal orientation. It can be said that it shows sex.
Here, it can be judged based on the order parameter (S) whether or not the organic light emitting material represented by the general formula (1) is arranged in the horizontal direction with respect to the substrate surface.
That is, as shown in FIG. 3, the extinction coefficient (ko, ke) is actually measured with an ellipsometer, and then the order parameter can be calculated based on the equation (1) shown in Example 1 described later. .
And if this order parameter is a value within the range of -0.5 to -0.1, it can be said that the organic light emitting materials are arranged substantially in the horizontal direction.
More specifically, when the order parameter exceeds -0.1, the horizontal orientation is insufficient, while when the order parameter is -0.5, it means that the orientation is completely horizontal. doing.
Therefore, the order parameter is more preferably a value in the range of −0.5 to −0.2, and even more preferably a value in the range of −0.5 to −0.22.

4). Horizontal orientation 2 (Horizontal angle (θ2))
Furthermore, the horizontal orientation of the organic light emitting material can be determined based on the horizontal angle (θ2) calculated from the order parameter (S).
That is, in accordance with the formula (1) shown in Example 1 described later, as shown in FIG. 1B, in the three-dimensional space composed of the XYZ axes, the Z axis that is the vertical axis and the molecules of the organic light emitting material The angle (θ) formed by the virtual axis direction can be calculated.
When an organic thin film made of an organic light emitting material is formed on the substrate, as shown in FIG. 1B, the horizontal angle (θ2) that is an angle formed by the virtual axis direction of the molecule of the organic light emitting material is ( 90 ° −θ), the horizontal orientation of the organic light emitting material can be determined based on the horizontal angle.
More specifically, if the horizontal angle is 31 ° or less, it can be determined that the organic light-emitting materials as the host material are arranged substantially in the horizontal direction.
However, if the horizontal angle is excessively small, the types of usable organic light emitting materials may be excessively limited.
Therefore, the horizontal angle is preferably set to a value within the range of 1 to 27 °, and the horizontal angle is further preferably set to a value within the range of 15 to 26 °.

5. Weight average molecular weight Moreover, it is preferable to make the weight average molecular weight of the organic luminescent material which has horizontal orientation into the value within the range of 400-1000.
This is because when the weight average molecular weight is less than 400, the heat resistance and durability may be significantly reduced. On the other hand, when the weight average molecular weight exceeds 1000, it may be difficult to uniformly disperse the predetermined guest material when the horizontally oriented molecule is used as a host material. .
Therefore, the weight average molecular weight of the organic light-emitting material having horizontal orientation is more preferably set to a value within the range of 410 to 800, and further preferably set to a value within the range of 420 to 600.
In addition, this weight average molecular weight can be measured by the gel permeation chromatography (GPC) method by polystyrene particle conversion, for example.

6). Electron mobility It is preferable that the electron mobility in the electric field intensity | strength of 1.0 * 10 < ⁶ > V / cm of the organic luminescent material which has horizontal orientation is 1 * 10 < ^-8 > cm < ² > / V * s or more.
This is because if the electron mobility is 1 × 10 ⁻⁸ cm ² / V · s or more, the organic light-emitting material has a high electron transporting property. This is because, when configured, high external quantum efficiency can be obtained even when a low voltage is applied.
In the present invention, the electron mobility can be measured by creating an electronic-only device.
More specifically, the relationship between the electric field and the mobility can be obtained by creating a predetermined electronic-only device and fitting with a Pool-Frenkel equation.
Here, FIG. 4 shows characteristic curves C and D in which the value of the electric field is taken on the horizontal axis and the electron mobility of the organic light emitting material is taken on the vertical axis.
The characteristic curve C is a curve obtained by taking the electron mobility of the organic light emitting material (CPFP) represented by the formula (3) of the present invention, and high electron mobility is obtained at any electric field value. .
For example, in an electric field of 1.0 × 10 ⁶ V / cm, the electron mobility of CPFP is 5.0 × 10 ⁻⁸ cm ² / V · s.
On the other hand, the characteristic curve D is a curve that takes the electron mobility of CBP that is generally used as a host material in an organic light emitting device, but the electron mobility is lower than CPFP at any electric field value. For example, in an electric field of 1.0 × 10 ⁶ V / cm, the electron mobility of CBP is 1.9 × 10 ⁻¹⁰ cm ² / V · s.
That is, in an electric field of 1.0 × 10 ⁶ V / cm, CPFP has a value two digits higher than that of CBP.
The reason for this is that, as described above, CPFP has a high horizontal orientation and, as shown in FIG. 1 (f), molecules are aligned in the device, so it is compared with CBP having a low molecular orientation. It is understood that this is because the mobility of electrons has increased.
Therefore, it is understood that the organic light-emitting material excellent in horizontal alignment of the present invention has excellent electron mobility as compared with the non-horizontal alignment organic light-emitting material.
In general, several methods such as the Time Of Flight method (TOF method) are known as methods for measuring the electron mobility of organic materials, but it is preferable to create and measure an electron-only device. .
This is because in the case of the TOF method, the film state to be measured becomes a relatively thick film, and the orientation may change.
That is, if it is the method of producing an electronic only device, since the electron mobility in a thin film state can be measured, the orientation of an organic material can fully be considered.
Moreover, the specific measuring method of electron mobility is described in an Example.

7). Hole mobility The hole mobility at an electric field strength of 1.0 × 10 ⁶ V / cm of the organic light emitting material having horizontal orientation is preferably 1 × 10 ⁻³ cm ² / V · s or more.
This is because if the hole mobility is 1 × 10 ⁻³ cm ² / V · s or more, the organic light-emitting material has high hole transportability, so that it can be used as a host material for organic light emission. This is because when the element is configured, high external quantum efficiency can be obtained even when a low voltage is applied.
In addition, the hole mobility is preferably measured by creating a hole-only device, similarly to the electron mobility.
Here, although not shown, the hole mobility was measured using a hole-only device in the same manner as the electron mobility. As a result, in an electric field of 1.0 × 10 ⁶ V / cm, the hole mobility of CPFP Is 2.1 × 10 ⁻³ cm ² / V · s, and the hole mobility of CBP is 9.9 × 10 ⁻⁴ cm ² / V · s.
That is, in an electric field of 1.0 × 10 ⁶ V / cm, CPFP has a hole mobility that is twice as high as CBP.
Therefore, it is understood that the organic light-emitting material having excellent horizontal alignment of the present invention is superior to the non-horizontal alignment organic light-emitting material in terms of hole mobility.
In addition, the specific measuring method of hole mobility is described in an Example.

8). Triplet energy Moreover, it is preferable that the triplet energy of the organic light-emitting material having horizontal orientation is 2.0 eV or more.
This is because, if the triplet energy of the organic light emitting material is 2.0 eV or more, when the organic light emitting material is used as a host material in an organic light emitting element, it exhibits an excellent triplet energy confinement effect and is high. This is because the external quantum efficiency can be obtained.
Furthermore, when the organic light-emitting material constitutes an electron transport layer of an organic light-emitting element as an electron transport material, a high exciton blocking effect is obtained, so that external quantum efficiency can be improved.
If the triplet energy of the organic light emitting material is 2.0 eV or more, it means that the organic light emitting material has a wide energy gap, and an organic light emitting device that emits red to blue light can be configured.
On the other hand, when the triplet energy of the organic light emitting material is less than 2.0 eV, when an organic light emitting device is configured using the organic light emitting material as a host, exciton energy generated in the light emitting layer is consumed by the host itself. , Since it does not move to the guest material, light emission may not occur.
However, if the triplet energy is excessively high, the types of organic light-emitting materials that can be used may be limited.
Therefore, the triplet energy is preferably set to a value in the range of 2.1 to 3.0 eV, and the triplet energy is more preferably set to a value of 2.2 to 2.9 eV.
Here, the triplet energy of the organic light emitting material CPFP represented by the formula (3) is 2.43 eV.
On the other hand, the triplet energy of CBP generally used as a host material in an organic light emitting device is 2.55 eV.
That is, from the viewpoint of triplet energy, the triplet energy of CPFP is lower than that of CBP.
However, it is well predicted that the triplet energy will be lowered when the biphenyl moiety is simply changed to the triphenyl moiety by extending the conjugated system in order to impart horizontal alignment to CBP that is non-horizontal alignment. However, CPFP has a donor-acceptor structure having a fluorine atom at the center of the molecule. Since the molecule is twisted by the fluorine atom, the conjugated system is broken, and the triplet energy is reduced. It is estimated that it did not decrease greatly.
Therefore, since the organic light-emitting material having horizontal orientation of the present invention has a relatively high triplet energy, as described later, when an organic light-emitting element is configured, it can be used as a host material or an electron transport material. Can also be used.
The triplet energy of the organic light emitting material is calculated from the maximum wavelength of the phosphorescence spectrum by measuring the light emission spectrum of the organic light emitting material at an extremely low temperature of 5K.
More specifically, as shown in FIGS. 5A to 5D, a thin-film device is created using FIr6 and CPFP, and from the obtained three types of emission spectra, from the phosphorescence spectrum of CPFP. Calculated.
That is, as shown by the characteristic curve E in FIGS. 5 (a) and 5 (b), first, fluorescence emission of the excited CPFP is observed, and then, in FIGS. 5 (a) and 5 (c). As shown in the characteristic curve F, phosphorescence emission of the excited FIr6 is observed, and finally, as shown in the characteristic curve G in FIGS. 5A and 5D, CPFP phosphorescence is observed. The triplet energy is calculated from the maximum wavelength in the phosphorescence spectrum of the CPFP.
Moreover, the specific measuring method of triplet energy is described in an Example.

[Second Embodiment]
The second embodiment of the present invention is represented by the general formula (1), and has an electron acceptor tetrafluoroarylene structure at the central portion and an electron donor arylene group at both ends thereof, respectively. A first step of preparing an aryl halide comprising 1,4-dihalogenated tetrafluoroarylene, a method for producing an organic light-emitting material having a donor-acceptor type molecular structure comprising a carbazolyl group, and a substituent A ^first boronic acid ester composed of carbazolylphenyl boronic acid ester having R ^{1 to} R ² and a ^second boronic acid ester composed of carbazolyl phenyl boronic acid ester having substituents R ^{3 to} R ⁴ , respectively. A palladium catalyst and a salt, the second step of preparing, the halogen at one end of the aryl halide, and the first boronic ester; After the cross-coupling by the action of the group nucleophile, the halogen at the other end of the aryl halide and the second boronic ester are cross-coupled by the action of the palladium catalyst and the base nucleophile. A third step of ringing, and a method for producing an organic light-emitting material.
Hereinafter, the manufacturing method of the predetermined | prescribed organic luminescent material which is the 2nd Embodiment of this invention is demonstrated concretely, referring drawings suitably.

1. Scheme In the scheme, the aryl halide prepared in the first step and the second step and the boronic ester are cross-coupled by the action of a palladium catalyst and a base nucleophile, respectively, and the above-described general formula (1) is used. It is a manufacturing method which obtains the organic luminescent material represented.
That is, by using the Suzuki-Miyaura coupling method (SMC method) for cross-coupling an organoboron compound and an aryl halide to obtain an asymmetric biaryl by the action of a palladium catalyst and a base nucleophile, the above-described method is used. The organic light emitting material represented by the general formula (1) has an advantage that it can be produced efficiently in a short time.

2. First Step The first step is a step of preparing a tetrafluoroaryl halide comprising 1,4-dihalogenated 2,3,5,6-tetrafluoroarylene prior to cross coupling.
That is, as the predetermined tetrafluoroaryl halide, 1,4-dibromo-2,3,5,6-tetrafluorobenzene, 1,4-dichloro-2,3,5,6-tetrafluorobenzene, 1,4 -Preparation of at least one of diiodo-2,3,5,6-tetrafluorobenzene and the like.
Such an aryl halide can be produced according to a known synthesis method, or a commercially available product can be used as it is.

3. Second Step The second step is a step of preparing a predetermined boronic ester prior to cross coupling.
In other words, the substituents R ¹ to R first boronate ester consisting carbazolylphenyl boronic acid ester having ² (substituents R ¹ to R ² are the same contents as the general formula (1).), and substituents R ³ to R ⁴ carbazolyl boronic acid ester having a (substituent R ³ to R ⁴ is a general formula (1) the same content as.) each prepared becomes second boronate ester from It is a process to do.
Therefore, in order to obtain an organic light-emitting material having an asymmetric structure, the substituents R ^{3 to} R ⁴ must be different from the substituents R ^{1 to} R ^2. The substituents R ^{3 to} R ⁴ in a given boronic acid ester must be the same as the substituents R ^{1 to} R ² (the same applies to the substituents a to d and the substituents ef). ). That is, in order to obtain an organic light-emitting material having a symmetric structure, either the first boronate ester or the second boronate ester is prepared and cross-coupled with the aryl halide as described later. .
More specifically, as the predetermined boronic acid ester, 9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole, 3 , 6-Dimethyl-9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole, 3-methyl-9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole, 9- (3-methyl-4- (4,4,5,5-tetra Methyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole, 9- (2-methyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 2-yl) phenyl) -9H-carbazol It is preferred to prepare at least one equal.
Such a boronic ester can be produced according to a known synthesis method, or a commercially available product can be used as it is.
Moreover, the boronic acid corresponding to the above-mentioned boronic acid ester can also be used as a precursor.

4). Third Step As shown in the reaction formula (1) and the reaction formula (2), the third step is an aryl halide represented by the formula (8) prepared in the first step and the second step, respectively (the symbol X is Br, Cl or I) and the prescribed boronic acid ester represented by formula (9) and formula (10) are sequentially cross-coupled by the action of a palladium catalyst and a base nucleophile, respectively, This is a step of forming an organic light emitting material represented by (1).

Here, in the third step, the predetermined boronic acid ester represented by the formula (9) and the formula (10) is dropped to the aryl halide represented by the formula (8), and the cross coupling is sequentially performed. It is preferable to make it.
The reason for this is that the activity of a given boronic acid ester tends to decrease in the reaction vessel. This is because the yield can be improved.
More specifically, a predetermined boronic acid ester can be effectively reacted with an aryl halide, which has a strong electron acceptor property and is generally considered to have a very low reactivity, and a predetermined organic light emission. The yield of the material can be dramatically improved. For example, when batch treatment is performed without dropping, the yield of about 1% can be improved to a yield of 50% or more when boronic ester is dropped and reacted. confirmed.
An example of suitable conditions when a predetermined boronic acid ester is dropped and reacted with a predetermined aryl halide is shown below.
Reaction temperature: 20-80 ° C
Dropping time: 5 to 36 hours Dropping speed: 0.05 to 0.4 molar equivalent / hour

In addition, when the organic luminescent material represented by the general formula (1) has an asymmetric structure with respect to the carbazolyl group composed of the substituents R ^{1 to} R ² and the carbazolyl group composed of the substituents R ^{3 to} R ⁴ , the reaction formula As shown in (1) and reaction formula (2), one boronic ester represented by formula (9) or formula (10) is first subjected to a cross-coupling reaction, and then the other boronic ester is cross-coupled. A ring reaction is performed, and a cross-coupling reaction is basically performed in two steps.
On the other hand, when the organic light emitting material represented by the general formula (1) has a symmetric structure with respect to the carbazolyl group composed of the substituents R ^{1 to} R ² and the carbazolyl group composed of the substituents R ^{3 to} R ⁴ , As in the modified example, the cross-coupling reaction may be basically generated in one step using any one of the predetermined boronic acid esters represented by the formula (9) and the formula (10).

5. Modified Example A modified example of the production method is represented by the general formula (1 ′), and an electron acceptor tetrafluoroarylene structure is formed at the central portion, and an electron donor arylene group is interposed at both ends thereof. And a method for producing an organic light-emitting material having a symmetric structure having a donor-acceptor type molecular structure each containing a dicarbazolyl group.
Then, a first step of preparing an aryl halide comprising 1,4-dihalogenated tetrafluoroarylene, and a boron comprising a carbazolyl group-containing boronic acid ester having substituents R ^{1 to} R ² or substituents R ^{3 to} R ⁴ A method for producing an organic light-emitting material, comprising: a second step of preparing an acid ester; and a third step of cross-coupling an aryl halide and a boronic ester by the action of a palladium catalyst and a base nucleophile. is there.
That is, by implementing in this way, a symmetrical organic luminescent material can be manufactured efficiently.
Further, by dropping a predetermined boronic acid ester to the aryl halide, a fresh boronic ester is always supplied even when the boronic acid ester has a short active period. The reactivity with respect to can be improved.
Therefore, according to the dropping method, a highly active boronic acid ester can be used to efficiently produce cross coupling, and a symmetrical organic light-emitting material can be produced in a very short time.

[Third Embodiment]
The third embodiment of the present invention is represented by the general formula (1), and an electron acceptor tetrafluoroarylene structure is formed at the central portion, and an electron donor arylene group is provided at both ends thereof. An organic light-emitting device comprising a light-emitting layer formed by blending a dopant material with an organic light-emitting material having a donor-acceptor type molecular structure containing a carbazolyl group as a host material.
A light emitting device comprising a light emitting layer or a plurality of organic thin film layers including a light emitting layer between a pair of electrodes consisting of an anode and a cathode, wherein the light emitting layer is a dopant material and a host material as a main component As an organic light-emitting device comprising the organic light-emitting material of the first embodiment.
Hereinafter, the organic light emitting material of the first embodiment, which is the third embodiment of the present invention, will be specifically described with reference to the drawings as appropriate, focusing on the organic light emitting device (organic EL device) when used as a host material. Explained.

1. Basic Configuration An organic light-emitting device of the present invention, for example, a typical organic EL device 110, as shown in FIG. 6 (a), has an anode 102 made of a transparent conductive material on a transparent substrate 101 such as glass or plastic, A hole transport layer 103 made of a predetermined organic compound, a light emitting layer 104 made of a predetermined organic compound, an exciton blocking layer 105 made of a predetermined organic compound, an electron transport layer 106 made of a predetermined organic compound, and a metal material A cathode 107 is stacked.
That is, the organic EL element 110 is configured using such a multilayer structure as a basic configuration, and high-luminance phosphorescence can be emitted by recombination with electrons and holes respectively injected from the electrodes.

2. Light-Emitting Layer The light-emitting layer contains a dopant material with respect to the host material together with the organic light-emitting material (host material) of the first embodiment.
Here, the type of the dopant material is not particularly limited, but high brightness phosphorescence can be obtained more stably and over a long period of time even in a relatively low current density region. It is preferable to use a complex compound or one of them.
Whether or not phosphorescence is emitted can be determined by, for example, the emission lifetime of the phosphorescent material using a streak camera (C4334, manufactured by Hamamatsu Photonics Co., Ltd.).
That is, as shown in FIG. 5 (a), when the emission spectrum of phosphorescence is measured and the predetermined emission intensity (Log ₁₀ (number of photons)) persists in the order of μsec or more, the obtained emission is phosphorescence. It can be judged that there is.

Here, FIG. 7 shows the relationship between the current density and voltage (JV characteristics) in the case where the light emitting layer includes CPFP represented by the above formula (3) as a host material and constitutes a device. To do.
Here, FIG. 7 shows characteristic curves H and I taking the applied voltage on the horizontal axis and the current density obtained on the vertical axis.
The characteristic curve H is a characteristic curve when CPFP of the present invention is used as a host material, and the characteristic curve I uses mCP represented by the following formula (G) which is generally used as a host material. It is a characteristic curve in the case.
The characteristic curve H has a higher current density than the characteristic curve I even when a low voltage is applied. In other words, in order to obtain the same current density, it can be seen that CPFP may be a lower voltage than mCP.
More specifically, it can be seen that CPFP requires 5.6V, while mCP requires 6V to obtain a current density of 10 mA / cm ² .
Therefore, it is understood that the organic light emitting material having the horizontal alignment property of the present invention is useful as a host material.

Further, specific examples of dopant materials such as iridium complex compounds will be shown while comparing with emission colors.
That is, as an iridium complex compound for extracting blue phosphorescence, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C ^{2 ′} ] iridium (III) tetrakis (1-pyrazolyl) borate, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C ^{2 ′} ] iridium (III) picolinate, bis {2- [3 ′, 5′-bis (trifluoromethyl) phenyl] pyridinato-N, C ^{2 ′} } iridium (III) picolinate, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C ^{2 ′} ] iridium (III) acetylacetonate, and the like.

As iridium complex compounds for extracting green phosphorescence, tris (2-phenylpyridinato-N, C ^{2 ′} ) iridium (III), bis (2-phenylpyridinato-N, C ^{2 ′} ) Iridium (III) acetylacetonate, bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate, bis (benzo [h] quinolinato) iridium (III) acetylacetonate, tris (benzo [ h] quinolinato) iridium (III) and the like.

Further, as an iridium complex compound for taking out yellow phosphorescence, bis (2-phenylpyridinato-N, C ^{2 ′} ) (2- (3- (2-oxo-2H-chromenyl)) pyridinato-N, C ^{4 ′} ) iridium (III), bis (2,4-diphenyl-1,3-oxazolate-N, C ^{2 ′} ) iridium (III) acetylacetonate, bis [2- (4′-perfluorophenylphenyl) Pyridinato] iridium (III) acetylacetonate, bis (2-phenylbenzothiazolate-N, C ^{2 ′} ) iridium (III) acetylacetonate, (acetylacetonato) bis [2,3-bis (4-fluoro Phenyl) -5-methylpyrazinato] iridium (III), (acetylacetonato) bis {2- (4-methoxyphenyl) -3,5-dimethylpyrazinato} i Examples include lithium (III).

As iridium complex compounds for extracting orange phosphorescence, tris (2-phenylquinolinato-N, C ^{2 ′} ) iridium (III), bis (2-phenylquinolinato-N, C ^{2 ′} ) iridium ( III) Acetylacetonate, (acetylacetonato) bis (3,5-dimethyl-2-phenylpyrazinato) iridium (III), (acetylacetonato) bis (5-isopropyl-3-methyl-2-phenylpyra) Zinato) iridium (III) and the like.

Furthermore, as an iridium complex compound for extracting red phosphorescence, bis [2- (2′-benzo [4,5-α] thienyl) pyridinato-N, C ^{3 ′} ] iridium (III) acetylacetonate, Bis (1-phenylisoquinolinato-N, C ^{2 ′} ) iridium (III) acetylacetonate, (acetylacetonato) bis [2,3-bis (4-fluorophenyl) quinoxalinato] iridium (III), (acetyl Acetonato) bis (2,3,5-triphenylpyrazinato) iridium (III), (dipivaloylmethanato) bis (2,3,5-triphenylpyrazinato) iridium (III) and the like It is done.

Examples of the platinum complex compound include bis (2-phenylpyridinato-N, C ^{2 ′} ) platinum (II), (2-phenylpyridinato-N, C ^{2 ′} ) platinum (II) acetylacetonate, (N, N′-bis (salicylidene) ethylenediaminato-N, N ′, O, O ′) platinum (II), (tetraphenylporfinato-N, N ′, N ″, N ″ ″) platinum One type of (II) or a combination of two or more types is preferred.

Moreover, it is preferable to make the compounding quantity of dopant material into the value within the range of 0.1-20 weight% with respect to the quantity (100 weight%) of the whole luminescent material which consists of dopant material and host material.
The reason for this is that when the blending amount of the dopant material is less than 0.1% by weight, the emission luminance may be remarkably lowered.
On the other hand, when the compounding amount of the dopant material exceeds 20% by weight, it may be difficult to uniformly disperse or easily crystallize with respect to a predetermined host material. .
Therefore, the blending amount of the dopant material is more preferably set to a value within the range of 1 to 10% by weight, and further to a value within the range of 2 to 8% by weight with respect to the total amount of the light emitting material. preferable.

Moreover, it is preferable to make the weight average molecular weight of dopant material into the value within the range of 400-1000.
This is because when the weight average molecular weight is less than 400, the heat resistance and durability may be significantly reduced. On the other hand, when the weight average molecular weight exceeds 1000, it may be difficult to uniformly disperse the predetermined host material.
Accordingly, the weight average molecular weight of the dopant material is more preferably set to a value within the range of 410 to 800, and further preferably set to a value within the range of 420 to 600.
In addition, this weight average molecular weight can be measured by the gel permeation chromatography (GPC) method by polystyrene particle conversion, for example.

  In addition, it is also preferable to add a material that assists electron transport to the light emitting layer. Examples of such electron transport auxiliary materials include triazole derivatives, oxazole derivatives, polycyclic compounds, heteropolycyclic compounds such as bathocuproine, oxadiazole derivatives, fluorenone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, anthraquinones. Dimethane derivatives, anthrone derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, acid anhydrides of aromatic ring tetracarboxylic acids such as naphthalenetetracarboxylic acid or perylenetetracarboxylic acid, phthalocyanine derivatives, 8-quinolinol derivatives One or two or more of metal complexes, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole or benzothiazole as a ligand, organosilane derivatives, iridium complexes, etc. Like a combination of.

3. Anode As the anode, a metal material or a metal oxide material having a relatively large work function, more specifically, 4 eV or more is used.
As such a metal material, for example, at least one of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like is preferable.
The thickness of the anode is usually preferably set to a value in the range of 300 to 3000 angstroms.

4). Cathode For the cathode, a material having a relatively small work function, more specifically, a metal material or metal oxide material of less than 4 eV is used.
As such a metal material, for example, lithium, barium, aluminum, magnesium, indium, silver, or an alloy thereof is preferable.
And it is preferable to make the thickness of a cathode into the value within the range of 100-5000 Angstrom normally.
In addition, if either one of the anode or the cathode described above is transparent or semi-transparent such as indium tin oxide (ITO), predetermined phosphorescence can be extracted to the outside.

5. Electron Transport Layer As shown in FIG. 6A, the electron transport layer includes at least the light emitting layer 104, the anode 102, the cathode 107, and an exciton blocking layer 105 described later, and an electron transport layer at a predetermined position. 106 is preferably provided.
Here, examples of the electron transport material to be blended in the electron transport layer include, for example, triazole derivatives, oxazole derivatives, polycyclic compounds, heteropolycyclic compounds such as bathocuproine, oxadiazole derivatives, fluorenone derivatives, diphenylquinone derivatives, thiols. Pyrandioxide derivatives, anthraquinone dimethane derivatives, anthrone derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, acid anhydrides of carbocyclic aromatic tetracarboxylic acids such as naphthalenetetracarboxylic acid or perylenetetracarboxylic acid, phthalocyanine derivatives , 8-quinolinol derivative metal complexes, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole or benzothiazole ligands, organic silane derivatives, iridium complexes, etc. Include combinations of the above German or two.

6). Exciton blocking layer Moreover, it is preferable to provide the exciton blocking layer 105 as shown to Fig.6 (a).
This is because by providing the exciton blocking layer 105 in this manner, the light emission efficiency can be increased and the lifetime of the organic EL element can be extended.
Here, the exciton blocking layer 105 can be provided by using the above-described electron transporting material, and is preferably a mixed layer in which two or more kinds of electron transporting materials are mixed and stacked by co-evaporation or the like. .
The electron transport material contained in the exciton blocking layer preferably has an ionization potential greater than that of the light emitting layer.

7). Other Configurations Although not shown, the periphery of the display area of the organic EL element is sealed with epoxy resin, acrylic resin, or the like, and a predetermined member in order to eliminate the influence of moisture and enhance durability. Preferably it is.
An inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil is preferably injected into the gap between the display area of the organic EL element and the predetermined member.
On the other hand, in order to eliminate the influence of moisture, it is also preferable to make the gap a vacuum or to enclose a hygroscopic compound in the gap.

8. Luminescence quantum yield (Φ)
Moreover, it is preferable to make the light emission quantum yield ((PHI)) measured about the organic luminescent material as a host material into the value within the range of 30-80%.
This is because when the emission quantum yield becomes a value of less than 30%, the emission luminance of the phosphorescence obtained may be lowered, or it may be difficult to extract the polarization component.
On the other hand, when the light emission quantum yield exceeds 80%, the types of usable organic light emitting materials may be excessively limited.
Therefore, it is more preferable to set the emission quantum yield measured using the organic light emitting material as the host material to a value in the range of 40 to 75%, and further to a value in the range of 50 to 70%. preferable.
In addition, the light emission quantum yield measured using the organic luminescent material as a host material can be measured according to the method described in the Example mentioned later.

9. External quantum efficiency (EQE)
Further, an external quantum efficiency (EQE) measured when a predetermined organic EL element is configured using an organic light emitting material as a host material is a current density of 0.0005 to 10 mA / cm ² . In the range, it is preferable to set the value within a range of 4 to 20%.
This is because when the external quantum efficiency is less than 4%, the obtained light emission luminance may be excessively lowered.
On the other hand, when the external quantum efficiency is excessively high, for example, a value exceeding 20%, the types of usable dopant materials may be excessively limited.
Therefore, the external quantum efficiency measured using the organic light emitting material as the host material is more preferably set to a value within the range of 4.5 to 18% within a predetermined current density range, More preferably, the value is within the range.
In addition, the external quantum efficiency measured using the organic luminescent material as a host material can be measured according to the method described in the Example mentioned later.

[Fourth Embodiment]
The fourth embodiment of the present invention is represented by the general formula (1), and has an electron acceptor tetrafluoroarylene structure at the central portion and an electron donor arylene group at both ends thereof, respectively. An organic light emitting device comprising an electron transporting layer including an organic light emitting material having a donor-acceptor type molecular structure containing a carbazolyl group as an electron transporting material.
Hereinafter, an organic light-emitting device using the organic light-emitting material of the first embodiment as an electron transport material will be described with reference to the drawings as appropriate, focusing on differences from the contents described in the third embodiment of the present invention. Explained.

1. Basic Configuration An organic light-emitting device of the present invention, for example, a typical organic EL device 111 includes an anode 102 made of a transparent conductive material on a transparent substrate 101 such as glass or plastic, as shown in FIG. A hole transport layer 103 made of a predetermined organic compound, a light emitting layer 104 made of a predetermined organic compound, an electron transport layer 106 made of a predetermined organic compound, and a cathode 107 made of a metal material are laminated.
That is, the organic EL element 111 is configured using such a multilayer structure as a basic configuration, and high-luminance phosphorescence can be emitted by recombination with electrons and holes respectively injected from the electrodes.

2. Light-Emitting Layer The light-emitting layer contains a dopant material for the host material together with the host material.
The host material that is the main component of the light emitting layer is not particularly limited, and is a polyphenylene compound, polyfluorene compound, polythiophene compound, polyphenylene vinylene compound, polycarbazole compound, polypyrrole compound, polyacetylene compound, polyaniline compound, polyaniline compound, One kind alone or a combination of two or more kinds such as an oxadiazole compound may be mentioned.

  More specifically, for example, 4,4′-dicarbazolyl-1,1′biphenyl (CBP) represented by the following formula (F) or N, N-dicarbazole-3 represented by the following formula (G) , 5-benzene, or tris (8-quinolinolato) aluminum represented by the following formula (H).

3. Electron Transport Layer Further, as shown in FIG. 6B, at least the light emitting layer 104, the anode 102, the cathode 107, and the electron transport layer 106 are provided at predetermined positions.
Here, as an electron transport material mix | blended with an electron carrying layer, the organic luminescent material of 1st Embodiment is contained, It is characterized by the above-mentioned.
This is because the organic light-emitting material having horizontal orientation of the donor-acceptor type represented by the general formula (1) has a relatively long molecular structure and is twisted by four fluorine atoms at the acceptor site. This is because the structure has a relatively high triplet energy and can contribute to the improvement of the external quantum efficiency of the organic light-emitting device as an electron transport material.

More specifically, FIG. 8 illustrates the relationship between the current density and the external quantum efficiency in the case where the device includes a CPFP represented by the above formula (3) as an electron transport material. To do.
Here, FIG. 8 shows characteristic curves J and K in which the horizontal axis represents current density and the vertical axis represents external quantum efficiency.
The characteristic curve J is a curve when CPFP of the present invention is used as an electron transport material, and the characteristic curve K is expressed by the above formula (H) generally used as an electron transport material. It is a curve at the time of using.
In the characteristic curve J, when CPFP is used for the electron transport layer, although the EQE tends to slightly decrease as the current density increases, a stable high external quantum efficiency is obtained at a low current density. Understood.
This is because CPFP has a relatively high triplet energy, and excitons generated in the light emitting layer are less consumed in the electron transport layer. In other words, it can be said that it has excellent exciton blocking properties.
On the other hand, since the carrier balance is insufficient, it is considered that the EQE tends to slightly decrease as the current density increases.
On the other hand, it is understood that the characteristic curve K has a tendency to improve the external quantum efficiency when the current density is high, but the external quantum efficiency is not sufficiently obtained in the low current density region.
The reason for this is that Alq3 has a high charge mobility and excellent carrier balance, so although the EQE tends to improve at a high current density, the triplet energy is not as large as 2.0 eV. Therefore, it is considered that a high EQE cannot be obtained when the current density is low.
That is, since the organic light-emitting material having horizontal orientation of the present invention has a relatively high triplet energy, it can be used as an electron transport material and has high exciton blocking characteristics. Thus, it can be said that the exciton blocking layer can be omitted and it is economically advantageous.
However, since the carrier balance is still insufficient, it can be said that the luminous efficiency can be further improved by improving the carrier balance.

4). Other Configurations It is also preferable to form the organic light emitting device by including the organic light emitting material of the present invention as a host material of the light emitting layer and also including it in the electron transport layer as an electron transport material.
More specifically, FIG. 12A shows a case in which a device including CPFP represented by the above-described formula (3) as a host material in a light emitting layer and an electron transporting material as an electron transport material is configured. The relationship between the current density and the external quantum efficiency is shown, and FIG. 12B shows the relationship between the applied voltage and the current density when the device is configured.
Here, FIG. 12A shows a characteristic curve L in which the horizontal axis represents current density and the vertical axis represents external quantum efficiency. FIG. 12B shows a characteristic curve M in which the horizontal axis represents the applied voltage and the vertical axis represents the current density.
That is, according to the figure, CPFP has a relatively high triplet energy and exciton blocking characteristics, so that it is possible to configure one device using CPFP as a host material and an electron transport material. It is understood that
In this case, since one evaporation source can be reduced when configuring the device, it can contribute to simplification of the device structure.

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

[Example 1]
1. Production of Organic Luminescent Material First, 1,4-bis {4- (9H-carbazol-9-yl) represented by the formula (3) from 1,4-dibromo-2,3,5,6-tetrafluorobenzene ) Phenyl} -2,3,5,6-tetrafluorobenzene was synthesized.
That is, after storing 1,4-dibromo-2,3,5,6-tetrafluorobenzene (commercial product, 616 mg 2 mmol) as a raw material compound in a container equipped with a dropping device and a stirrer, the nitrogen atmosphere was changed to tetrakis. After degassing by adding (triphenylphosphine) palladium (0) (200 mg, 0.17 mmol), potassium carbonate (2540 mg, 18.4 mmol), 50 ml of tetrahydrofuran (THF), and 12 ml of water. And heated to 60 ° C.
9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole (synthetic product, 1477 mg, 4 mmol) was then added to 10 ml of THF. A liquid material obtained by dissolving and degassing was added dropwise over 12 hours, and the mixture was further heated and stirred at 60 ° C. for 3 days to obtain a reaction solution.
Then, the solvent is evaporated to dryness (evaporation) from the obtained reaction solution, and the resulting residual solid is collected by filtration. Further, the residual solid is dissolved in dichloromethane, and the solution is washed with water and saturated brine. After drying with magnesium sulfate, the solvent was evaporated to dryness and further residual solid was collected by filtration.
Finally, the obtained solid residue is purified by silica gel column chromatography and recrystallized using dichloromethane / hexane to give 1,4-bis { 4- (9H-carbazol-9-yl) phenyl} -2,3,5,6-tetrafluorobenzene (CPFP, 923 mg, 1.46 mmol, 73% yield) was obtained.

2. Thin film formation using organic light-emitting material A thin film (thickness: 50 nm) made of the organic light-emitting material (CPFP) is formed on a silicon substrate (size: 10 mm × 10 mm × 0.7 mm) by using a vacuum deposition method. did.
In addition, as vapor deposition conditions, it is as follows.
Film forming device: E-180-S with ultra-precise alignment mechanism (manufactured by ALS Technology Co., Ltd.)
Film forming speed: 1.0 cm / sec.
Film forming pressure: 2.0 × 10 ⁻⁴ Pa
Film forming time: 9.3 minutes

3. Evaluation of organic luminescent material (1) Evaluation of order parameter (S) Substrate using an ellipsometer (M-2000 manufactured by JA Woollam Co., Ltd.) for a thin film of organic luminescent material (CPFP) obtained on a silicon substrate. The amplitude ratio and the phase difference (Psi and Delta) were measured as changes in the polarization state of the polarized light incident at different angles with respect to. Based on these values, an assumed optical model is constructed, fitting is performed so that the mean square error between the two is minimized, an extinction coefficient is calculated, and the following equation (1) is applied. Thus, the order parameter (S) was obtained. The obtained results are shown in Table 1.
The construction of the optical model, the fitting for minimizing the mean square error between the optical model and the actual measurement value, etc. were performed using WASE32 (manufactured by JA Woollam Co., Ltd.) which is software for ellipsometry data analysis.

Here, in Equation (1), the symbol k is an extinction coefficient, and the subscripts o and e are extinction coefficients in the xy direction (plane direction) and the z direction (vertical direction) with respect to the substrate, respectively. It shows that. And the extinction coefficient (k) of the obtained organic luminescent material (CPFP) can be measured using the ellipsometer mentioned above. FIG. 3 shows the obtained extinction coefficient chart on the vertical axis and the wavelength on the horizontal axis.
In addition, in Formula (1), (theta) means the angle which the Z axis | shaft which is a perpendicular axis, and the virtual axis direction of the molecule | numerator of an organic light emitting material make in the three-dimensional space which consists of an XYZ axis.

(2) Horizontal orientation evaluation Further, from the value of the order parameter (S) described above, an angle (θ) formed by the Z axis that is the vertical axis and the virtual axis direction of the molecule of the organic light emitting material is calculated. As an index of horizontal orientation, an angle formed by the substrate and the virtual molecular axis direction of the organic light emitting material (CPFP), that is, a horizontal angle (θ2 = 90 ° −θ) was calculated. The obtained results are shown in Table 1.

(3) NMR
NMR (nuclear magnetic resonance) of the obtained organic light emitting material (CPFP) was measured using JNM-EPC400 (manufactured by JEOL) in a state dissolved in deuterated chloroform solvent. The obtained NMR chart is shown in FIG.

(4) FT-IR
The FT-IR chart of the obtained organic light emitting material (CPFP) was measured by KBr tablet method using FT / IR-6100 (manufactured by JASCO). The obtained FT-IR chart is shown in FIG.

(5) Light absorption wavelength spectrum and emission peak The light absorption wavelength spectrum of the obtained organic light emitting material (CPFP) was measured using UV-2550 (manufactured by Shimadzu Corporation) which is an ultraviolet-visible spectrophotometer.
Further, the emission intensity (fluorescence emission spectrum) in the obtained organic light emitting material (CPFP) was measured using a spectrofluorometer FP-6500 (manufactured by JASCO).
The obtained light absorption wavelength spectrum is shown in FIG. 11 (a), and the obtained fluorescence emission spectrum is shown in FIG. 11 (b).

(6) Luminescence quantum yield Using the absolute PL quantum yield measuring device C9920 (manufactured by Hamamatsu Photonics Co., Ltd.), the luminescence quantum yield at a predetermined wavelength (337 nm) is obtained for the obtained thin film of the organic light emitting material (CPFP). The rate (internal quantum efficiency) was measured. The obtained results are shown in Table 1.

(7) Electron mobility and hole mobility Using the obtained organic light emitting material (CPFP), the following electron-only device and hole-only device were prepared, and the relationship between voltage and current density was obtained.
Next, the relationship between the electric field and the mobility was derived from the relationship between the voltage and the current density by fitting with the following Poole-Frenkel formulas (2) to (3). FIG. 4 shows the relationship between the obtained electric field and electron mobility, and Table 1 shows the electron mobility and hole mobility at an electric field of 1 × 10 ⁶ V / cm.
(Configuration of electronic only device)
ITO (100 nm) / BCP (10 nm) / CPFP (150 nm) / LiF (0.5 nm) / Al (80 nm)
That is, a glass substrate (12 mm long × 12 mm wide × 1 mm thick) on which an indium tin oxide film having a thickness of 100 nm was deposited was prepared as an anode.
In addition, 9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP, 10 nm) as a hole blocking layer, CPFP vapor deposition layer (150 nm) as an electron transport layer, and LiF as an electron injection material While depositing a vapor deposition layer (0.5 nm) and an Al vapor deposition layer (80 nm) as a cathode, respectively, and connecting a power supply, it was set as the electronic only device.
(Hall-only device configuration)
ITO (100 nm) / MoO ₃ (0.8 nm) / CPFP (250 nm) / MoO ₃ (10 nm) / Al (80 nm)
Similarly, a glass substrate (12 mm long × 12 mm wide × 1 mm thick) on which an indium tin oxide film having a thickness of 100 nm was deposited was prepared as an anode.
On top of that, molybdenum oxide (VI) MoO ₃ (0.8 nm) as a hole injection material, CPFP vapor deposition layer (250 nm) as a hole transport layer, and MoO ₃ vapor deposition layer (10 nm) as an electron blocking layer. And as a cathode, while depositing Al vapor deposition layer (80 nm), respectively, and connected the power supply, it was set as the hole only device.
In addition, as vapor deposition conditions, it is as follows.
Film forming device: E-180-S with ultra-precise alignment mechanism (manufactured by ALS Technology Co., Ltd.)
Film-forming speed: 1.0cm / sec
Film forming pressure: 2.0 × 10 ⁻⁴ Pa

J = μ ₀ ε ₀ εV ² L ⁻³ exp (βV ^0.5 ) (2)

μ = μ ₀ exp (βV ^0.5 ) (3)

(8) Triplet energy The triplet energy of the obtained organic light emitting material (CPFP) was calculated from the peak top of phosphorescence emission.
More specifically, the emission spectrum of a thin film doped with 6 wt% of phosphorescent dopant IR6 in CPFP was measured with a streak camera (Hamamatsu Photonics Co., Ltd.) when excited with a 337 nm nitrogen laser under 5K conditions. ), C4334), and measured in nanosecond order, subnanosecond order, and microsecond order, respectively, and converts the peak top wavelength into triplet energy (eV) for the long-lived emission observed in the microorder. Was calculated.
The obtained emission spectra are shown in FIGS. 5 (a) to (d), and the triplet energy values obtained are shown in Table 1.

(9) JV characteristics The following organic EL elements were constructed using the obtained organic light emitting material (CPFP) as a host material. Next, J-V characteristics (current density VS voltage) were measured. The obtained JV characteristic curve is shown as line H in FIG.
(Configuration of organic EL element)
ITO (100 nm) / TPD (50 nm) / 6 wt% Ir (ppy) ₃ CPFP (20 nm) / TPBi (50 nm) / LiF (0.5 nm) / Al (100 nm)
That is, a glass substrate (12 mm long × 12 mm wide × 1 mm thick) on which an indium tin oxide film having a thickness of 100 nm was deposited was prepared as an anode.
On top of that, N, N′-bis (3-methylphenyl) -N, N′-bis (phenyl) -benzidine vapor deposition layer (TPD, 50 nm) is used as a hole transport layer, and Ir (ppy) is used as a light emitting layer. ) CPFP vapor-deposited layer (20 nm) containing ₃ at a concentration of 6% by weight, and 2,2 ′, 2 ″-(1,3,5-benztolyl) -tris (1-phenyl-1) as an electron transport layer -H-benzimidazole) vapor-deposited layer (TPBi, 50 nm), LiF vapor-deposited layer (0.5 nm) as an electron injection layer, and Al vapor-deposited layer (100 nm) as a cathode, respectively, and connected to a power source Thus, an organic EL element was obtained.
In addition, as vapor deposition conditions, it is as follows.
Film forming device: E-180-S with ultra-precise alignment mechanism (manufactured by ALS Technology Co., Ltd.)
Film forming speed: 1.0 Å / sec (dopant: 0.06 Å / sec)
Film forming pressure: 2.0 × 10 ⁻⁴ Pa

(10) External quantum efficiency The following organic EL element was comprised using the obtained organic light emitting material (CPFP) as an electron transport material. The external quantum efficiency was then measured. The obtained external quantum efficiency is shown in FIG.
(Configuration of organic EL element).
ITO (100 nm) / NPD (50 nm) / 6 wt% Ir (ppy) ₃ mCP (20 nm) / CPFP (50 nm) / MgAg (100 nm) / Ag (20 nm)
That is, a glass substrate (12 mm long × 12 mm wide × 1 mm thick) on which an indium tin oxide film having a thickness of 100 nm was deposited was prepared as an anode.
On top of that, N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine vapor deposition layer (NPD, 50 nm) is used as a hole transport layer, and Ir (ppy) ₃ is 6 weights as a light emitting layer. A mCP vapor deposition layer (20 nm) containing at a concentration of%, a CPFP vapor deposition layer (50 nm) as an electron transport layer, and a MgAg vapor deposition layer (100 nm) and an Ag vapor deposition layer (20 nm) as a cathode, respectively, A power source was connected to obtain an organic EL element.
The vapor deposition conditions are as described above.

(11) Application example The obtained organic light emitting material (CPFP) is used as a host material and an electron transport material to constitute the following organic EL device, and then the JV characteristics (current density VS voltage) and external quantum Efficiency was measured. FIG. 12A shows the obtained external quantum efficiency, and FIG. 12B shows the obtained JV characteristic.
(Configuration of organic EL element)
ITO (100 nm) / NPD (50 nm) / 6 wt% Ir (ppy) ₃ CPFP (20 nm) / CPFP (50 nm) / MgAg (100 nm) / Ag (20 nm)
That is, a glass substrate (12 mm long × 12 mm wide × 1 mm thick) on which an indium tin oxide film having a thickness of 100 nm was deposited was prepared as an anode.
On top of that, N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine vapor deposition layer (NPD, 50 nm) is used as a hole transport layer, and Ir (ppy) ₃ is 6 weights as a light emitting layer. A CPFP vapor deposition layer (20 nm) containing at a concentration of%, a CPFP vapor deposition layer (50 nm) as an electron transport layer, and a MgAg vapor deposition layer (100 nm) and an Ag vapor deposition layer (20 nm) as a cathode, respectively, A power source was connected to obtain an organic EL element.
The vapor deposition conditions are as described above.

[Comparative Example 1]
As the organic light emitting material having non-horizontal orientation, 4,4′-di (N-carbazolyl) biphenyl (CBP) represented by the above formula (F) is used, and the order parameter (S) The results obtained are shown in Table 1.

[Comparative Example 2]
As an organic light-emitting material having non-horizontal orientation, 4,4′-di (N-carbazolyl) triphenyl (hereinafter sometimes referred to as CBTP) represented by the following formula (I) was used, and the same as in Example 1. Table 1 shows the results obtained by evaluating the order parameters (S) and the like.

As described above in detail, according to the present invention, when a film is formed, an organic light-emitting material exhibiting excellent horizontal orientation and the like, an efficient method for producing such an organic light-emitting material, and such an organic An organic light emitting device including a light emitting material can be obtained.
In addition, since the organic light-emitting material has relatively high electron mobility and triplet energy, when used as a host material, it can be expected to have a triplet energy confinement effect, and can be used as an electron transport material. In that case, it is expected to exhibit excellent exciton blocking properties.
Further, according to the method for producing an organic light-emitting material of the present invention, in particular, in the third step, a predetermined boronic ester is dropped with respect to the aryl halide while being cross-coupled. The acid ester can be used as fresh, and the reaction yield can be dramatically improved even for aryl halides which are usually said to have low reactivity.

10: Horizontal alignment material (molecule of host material)
10 ': Donor-acceptor type molecular structure 12: Substrate (glass substrate)
20: Dopant material 30: Non-horizontal orientation host material (molecule of host material)
110, 111: Organic EL element 101: Transparent substrate 102: Anode 103: Hole transport layer 104: Light emitting layer 105: Exciton blocking layer 106: Electron transport layer 107: Cathode

Claims (11)

A donor represented by the following general formula (1), comprising: an electron acceptor tetrafluoroarylene structure at a central site; and a carbazolyl group at each end via an electron donor arylene group. -It has an acceptor type molecular structure,
An organic light-emitting material characterized in that the order parameter calculated from the anisotropy of the extinction coefficient is a value in the range of -0.5 to -0.2.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom.)   The organic light-emitting material according to claim 1, wherein the order parameter is set to a value within a range of -0.5 to -0.22. In a three-dimensional space composed of XYZ axes, a horizontal angle (θ2) represented by ( 90 ° −θ), where θ is an angle formed by the Z axis that is the vertical axis and the virtual axis direction of the molecule of the organic light emitting material. The organic light-emitting material according to claim 1, wherein the value is 31 ° or less. The electron mobility is 1 × 10 ⁻⁸ cm ² / V · s or more at an electric field strength of 1.0 × 10 ⁶ V / cm, according to claim 1. Organic light emitting material.   Triplet energy is 2.0 eV or more, The organic luminescent material as described in any one of Claims 1-4 characterized by the above-mentioned. A donor represented by the following general formula (1), comprising: an electron acceptor tetrafluoroarylene structure at a central site; and a carbazolyl group at each end via an electron donor arylene group. An organic light-emitting material manufacturing method having an acceptor type molecular structure and an order parameter calculated from the anisotropy of the extinction coefficient in a range of -0.5 to -0.2; ,
A first step of preparing an aryl halide comprising 1,4-dihalogenated tetrafluoroarylene;
The first boronic acid ester consisting carbazolylphenyl boronic acid ester having a substituent R ¹ to R ^2, and substituents R ³ to R comprising ^{4-carbazolylphenyl} boronic acid ester with a second boronic acid ester A second step of preparing each,
After the halogen at one end of the aryl halide and the first boronic ester are cross-coupled by the action of a palladium catalyst and a base nucleophile, the other end of the aryl halide is A third step of cross-coupling the halogen and the second boronic acid ester by the action of a palladium catalyst and a base nucleophile;
A method for producing an organic light-emitting material comprising:

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom.)   The said 3rd process WHEREIN: The said 1st boronate ester and the said 2nd boronate ester are made to cross-couple, dripping with respect to the said aryl halide, respectively. The manufacturing method of organic luminescent material. It is represented by the following general formula (1 ′), and includes an electron-accepting tetrafluoroarylene structure at a central site and a carbazolyl group at each end via an electron-donating arylene group. This is a method for producing an organic light-emitting material having a donor-acceptor type molecular structure and having an order parameter calculated from the anisotropy of the extinction coefficient within a range of -0.5 to -0.2. And
A first step of preparing an aryl halide comprising 1,4-dihalogenated tetrafluoroarylene;
A second step of preparing a boronic acid ester comprising a carbazolylphenyl boronic acid ester having substituents R ^{1 to} R ² or substituents R ^{3 to} R ⁴ ;
A third step in which the aryl halide and the boronic ester are cross-coupled by the action of a palladium catalyst and a base nucleophile;
A method for producing an organic light-emitting material comprising:

(In the general formula (1 ′), each of the substituents R ^{1 to} R ² (or R ^{3 to} R ⁴ ) and a to d (or e to h) is a hydrogen atom.)   9. The method for producing an organic light emitting material according to claim 8, wherein in the third step, the boronic acid ester is cross-coupled to the aryl halide while dropping. A donor represented by the following general formula (1), comprising: an electron acceptor tetrafluoroarylene structure at a central site; and a carbazolyl group at each end via an electron donor arylene group. An organic light emitting material having an acceptor type molecular structure and having an order parameter calculated from the anisotropy of the extinction coefficient within a range of -0.5 to -0.2 is used as a host material, An organic light emitting device comprising a light emitting layer containing a dopant material.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom.) A donor represented by the following general formula (1), comprising an electron acceptor tetrafluoroarylene structure at a central portion and a carbazolyl group at each end via an electron donor arylene group -An organic light-emitting material having an acceptor type molecular structure and having an order parameter calculated from the anisotropy of the extinction coefficient within a range of -0.5 to -0.2 is included as an electron transport material. An organic light emitting device comprising an electron transport layer.

(In the general formula (1), each of the substituents R ^{1 to} R ⁴ and a to h is a hydrogen atom.)

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