WO2017067422A1 - Pyrimidine phenyl carbazoline derivative, and organic light-emitting diode device therefor - Google Patents

Abstract

The present invention relates to an organic compound as shown in formula (I), said compound being an organic phosphorescent light-emitting material. Carbazoline is bonded to an aromatic ring, the organic compound has good solubility in alcohol solvents, and the pyrimidine skeleton in the molecule is also an alcohol-soluble group. The structure of the compound has a carbazoline structure, and the compound therefore has a high triplet state and electron mobility, and acts as a blue phosphorescent host and electron transport material. In addition, the compound is soluble in alcohol solvents, facilitating purification etc., and may also act as an inkjet printing OLED material.

Description

Aromatic heterocyclic derivative and organic light emitting diode device using the same Technical field

The present invention relates to an aromatic heterocyclic derivative and an organic light emitting diode (OLED) device, and more particularly to an aromatic heterocyclic derivative having high luminous efficiency due to high triplet energy and electron transporting performance. And an OLED device using the aromatic heterocyclic derivative.

Background technique

In recent years, organic electroluminescent devices have been extensively researched and developed. In the basic structure of such a light-emitting element, a layer containing a light-emitting substance is interposed between a pair of electrodes, and by applying a voltage to the element, light emission from the light-emitting substance can be obtained.

Since such light-emitting elements are self-illuminating elements, they have advantages in terms of high pixel visibility and elimination of backlighting requirements with respect to liquid crystal displays, and thus are considered to be suitable for flat panel display elements, for example. Light-emitting elements are also advantageous because they are thin and lightweight. Very high speed response is one of the features of this component.

Further, since such a light-emitting element can be formed in the form of a film, planar light emission can be provided. Therefore, an element having a large area can be easily formed. This is a feature that is difficult to obtain using a point light source typified by an incandescent lamp and an LED or a linear light source typified by a fluorescent lamp. Therefore, the light-emitting element also has a large potential as a planar light source or the like applicable to illumination.

The excited state formed by the organic compound may be singlet or triplet. The emission from the singlet excited state (S ^* ) is fluorescence, and the emission from the triplet excited state (T ^* ) is called phosphorescence. Further, it is considered that the statistical generation ratio in the light-emitting element is S ^* :T ^* =1:3. In the compound which converted the energy of the singlet excited state into light emission, no emission from the triplet excited state was observed at room temperature, and only emission from the singlet excited state was observed. Therefore, it is considered that the internal quantum efficiency of a light-emitting element using a fluorescent compound has a theoretical limit of 25% based on a ratio of S ^* to T ^* of 1:3. Therefore, organic electrophosphorescent materials are recently attracting a class of materials, organic electroluminescent materials with high luminous efficiency and luminescent brightness, which utilize the method of introducing heavy metal atoms to utilize the originally forbidden triplet transition at room temperature. Thus, the internal quantum efficiency theory can reach 100%, which is four times that of a single fluorescent material (1, Cao Y., Parker ID, Heeger J., Nature, 1999, 397: 414-417.2, Wohlgenann M., et al. Nature, 2001, 409: 494-497.). Most of the heavy metal atoms commonly used in organic electrophosphorescent materials are transition metals. Among them, ruthenium is the most widely used and most studied. This is because metal ruthenium complexes have high efficiency, strong phosphorescence at room temperature, and can pass through ligands. The adjustment of the structure adjusts the wavelength of the illumination such that the color of the electroluminescent device covers the entire visible region. Therefore, designing and synthesizing new and highly efficient metal ruthenium complexes is of great significance for the development of phosphorescent materials.

However, the efficiency of the dopant is drastically reduced due to the quenching phenomenon, and thus exists for the light-emitting layer of the dopant having no host. limit. Therefore, it is desirable to form a layer of luminescent material by a dopant and a host having higher thermal stability and triplet energy.

In an OLED device comprising a phosphorescent compound, holes from the anode and electrons from the cathode are combined at the body of the layer of luminescent material. The single-state exciton of the host undergoes an energy level transition to the singlet or triplet level of the dopant, and an energy level transition from the triplet exciton of the host to the triplet level of the dopant occurs. The excitons that transition to the singlet state of the dopant again transition to the triplet level of the dopant. The exciton of the triplet level of the dopant transitions to the ground state, causing the luminescent layer to emit light.

To achieve a high-level transition of the transition to the dopant, the triplet energy of the bulk should be greater than the triplet energy of the dopant. When the triplet energy level of the body is smaller than the triplet energy of the dopant, a reverse transition from the dopant to the bulk energy occurs, thereby reducing the luminous efficiency.

CBP, which is widely used in the main body, has a triplet level of 2.6 eV, a maximum energy level of about -6.3 eV, and a lowest energy level of about -2.8 eV. Therefore, using the triplet level 2.8eV, the highest level -5.8eV and the lowest level -3.0eV blue dopant FCNIr, the energy level reverse transition from dopant to host occurs, resulting in reduced luminous efficiency. In particular, the occurrence of a decrease in luminous efficiency is more remarkable under low temperature conditions.

Pyrimidine structure As an electron-withdrawing group, bipolar host materials and electronic materials can be designed with high triplet state and electron transport capability. Idemitsu Trading Co., Ltd. has been engaged in the development of main materials and electronic materials for pyrimidine series, and has developed some materials. A (refer to patent US 20040086745) B (reference patent US20140151647)

A level (HOMO-5.71, LUMO-2.16, singlet 3.55eV, triplet 2.90eV) B level (HOMO-6.13, LUMO-2.62, singlet 3.51eV, triplet 2.65eV) two structures slightly different There is a big difference between the triplet and the HOMO. The electron transport energy can reach 10 ^-6 , indicating the presence of pyrimidine groups and enhancing the electron transport ability. Although the triplet level is high, HOMO is less than -6.0eV, which does not effectively block holes. Although B can effectively block holes, the triplet level is a bit low and can only be used as the main material of red and green light.

Summary of the invention

The present invention relates to an aromatic heterocyclic derivative and an OLED device using a phosphorescent compound which substantially solve one or more problems due to limitations and disadvantages of the prior art.

SUMMARY OF THE INVENTION An object of the present invention is to provide a phosphorescent compound which has high triplet energy and electron transporting properties and can be used as a host of a phosphorescent device and an electron transporting material.

Another object of the present invention is to provide an OLED device having higher luminous efficiency. The structure of oxazoline is similar to that of carbazole, because the structure has a pyridine structure, the triplet state is higher than that of carbazole, the triplet state of the same structural material is also high, and the electron mobility is also greatly enhanced (Chil Won Lee and Jun Yeob Lee, Adv. Mater. 2013, 25, 5450–5454). In order to meet the requirements of blue phosphorescent materials in terms of triplet state, electron mobility, etc., it is a good choice to introduce oxazoline groups into the structure.

An aromatic heterocyclic compound represented by the formula (I),

Wherein R1 to R5 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a C1-C4 substituted or unsubstituted phenyl group or biphenyl,

Ar3, Ar4 are each independently a C1-C4 substituted or unsubstituted oxazoline, carbazole or hydrogen; and at least one is an oxazoline, an oxazole or an oxazoline is linked through a 9-position nitrogen atom,

One of the four positions 1, 2, 3, and 4 of the oxazoline ring is a nitrogen atom, which constitutes the four isomers of the oxazoline:

Ar5 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aromatic group of C6-C40, a substituted or unsubstituted heterocyclic aromatic group,

A3 and a4 each independently represent a C1-C4 substituted or unsubstituted phenylene group, and j, k each independently represent 0 or 1, and the hetero atom of the heteroaryl group is N, O, S.

Preferably, wherein R1 is hydrogen or benzene, biphenyl, R2 to R5 represent hydrogen, j, k represents 0, and Ar5 represents a substituted or unsubstituted phenyl or biphenyl group.

The organic compound is represented by the following formula (II):

Wherein R6 to R8 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group of C6-C40, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted fused ring aryl group; , substituted or unsubstituted fused ring heteroaryl.

Ar6, Ar7 represents hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or not Substituted aryl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthothiophene, oxazoline, pyridine, phenanthroline substituted or unsubstituted heterocyclic ring An aryl group; an oxazoline is linked by a 9-position nitrogen atom,

One of the four positions 1, 2, 3, and 4 of the oxazoline ring is a nitrogen atom, which constitutes the four isomers of the oxazoline:

A6 and a7 each independently represent a substituted or unsubstituted phenylene group, and m, n each independently represent 0 or 1.

Preferably, R1 is hydrogen or benzene, R2 to R5, R6, R8 represent hydrogen, j, k m, n represents 0, Ar6, Ar7 represents hydrogen, and R7 is unsubstituted or substituted with 1-4 carbon atoms, phenyl Phenyl, naphthyl, anthracenyl, fluorenyl, aryl, heterocyclic aryl.

Preferably, Ar3 and Ar4 are each independently an oxazoline, a hydrogen atom, or a carbazole, and at least one of them is an oxazoline.

The organic compound is represented by the following formula:

Wherein R9 and R10 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a C1-C4 substituted or unsubstituted phenyl group or biphenyl.

Preferably, R1 is hydrogen or benzene, R2 to R5, R6, R8 to R10 represent hydrogen, j, n represents 0, Ar3 is oxazoline, Ar7 represents hydrogen, and R7 is unsubstituted or substituted with 1-4 carbon atoms. A heterocyclic aryl group, a biphenyl group, a naphthyl group, an anthracenyl group, a spirofluorenyl group, and a C6-C20 group.

As the structure described in the general formula of the patent, the following structure is exemplified, but the present invention is not limited to the following structure.

The examples cited in this patent are only listed in the scope of patent claims, but the patents are not limited to the present examples, as long as the structures satisfying the claims are within the scope of the patent.

An organic light emitting diode device comprising: a first electrode; a second electrode opposite to the first electrode; a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer comprises any one of the above organic compounds .

The material of the light-emitting layer includes a host and a dopant, and the above-described organic compound serves as a host material.

The host material is a blue phosphorescent host material.

The device is a display device and a lighting device.

The compound we designed is mainly the structure of the pyrimidine skeleton, and the structure of the two compounds A and B indicated in the background art is improved. When the HOMO is less than -6.0 eV, the triplet level needs to be increased. Oxazolines are similar structures to carbazole and have the properties of carbazole, but the triplet and electron transport properties are stronger than carbazole. We replaced the carbazole structure in the above structure with an oxazoline structure to obtain a list of heterocyclic derivatives. The obtained oxazoline derivative still has a pyrimidine skeleton and an oxazoline structure, and the oxazoline is bonded through the nitrogen atom at the 9-position, and the molecular weight does not largely change. The oxazoline has good solubility in an alcohol solvent, and it is bonded to the aromatic ring to maintain this property. In addition, there is a pyrimidine skeleton in the molecule, which is also a group soluble in alcohol. The carbazole group is a rigid group, and the obtained A and B structures have low solubility, which is not favorable for purification.

The structure designed by this patent has an oxazoline structure, is soluble in an alcohol solvent, and is convenient for purification. It is easily soluble in alcohol solvents and can be used as an inkjet printing OLED material.

DRAWINGS

Figure 1 shows the nuclear magnetic properties of compound 3,

Figure 2, the nuclear magnetic field of compound 4,

Figure 3 shows the nuclear magnetic field of the first body,

Figure 4 shows the nuclear magnetic field of the second body,

Figure 5 shows the nuclear magnetic field of the fourth body.

detailed description

Example 1. Preparation of the first body

Synthesis of Compound 1: 3,5-Dibromobenzaldehyde was lithiated from 1,3,5-tribromobenzene to give a white solid (CN100366703).

Synthesis of Compound 3:

To 1000 mL of ethanol, 50.8 g of 3,5-dibromobenzaldehyde and 37.8 g of acetylbiphenyl were added, and the mixture was stirred at room temperature, and 14.2 g of a 70 ml aqueous solution was added dropwise thereto, and the mixture was stirred at room temperature for 2 hours, and the reaction was stopped by TLC.

The obtained product was washed repeatedly with water and ethanol to give 81 g of pale yellow solid, yield 98%. Nuclear magnetics are shown in Figure 1.

Synthesis of Compound 4:

In 1000 L of absolute ethanol, the 81 G product obtained in the previous step, 30 G of benzamidine hydrochloride, 15 G of sodium hydroxide was added, stirred, and refluxed overnight. A large amount of solid was obtained, which was filtered, washed with water and washed with ethanol to give a white solid. 50 G, 60% yield was obtained. Nuclear magnetics are shown in Figure 2.

Synthesis of the first host material:

A 1 L four-necked flask was charged with 800 ML DMF, and 46 G of compound 4, 50 G of 1-oxazoline, copper powder, potassium carbonate was added, and the mixture was stirred under nitrogen for 30 minutes, and the temperature was refluxed. No intermediates were present in the 24 hour TLC assay, the reaction was stopped and filtered. The obtained solution was poured into water, a solid was precipitated, filtered, and purified by toluene to give a 40 g product. Nuclear magnetics are shown in Figure 3.

Example 2: Preparation of second body

Synthesis of Compound 1 : 3,5-Dibromobenzaldehyde was lithiated from 1,3,5-tribromobenzene to give a white solid.

Synthesis of Compound 3:

To 1000 mL of ethanol, 50.8 g of 3,5-dibromobenzaldehyde and 37.8 g of acetylbiphenyl were added, and the mixture was stirred at room temperature, and 14.2 g of a 70 ml aqueous solution was added dropwise thereto, and the mixture was stirred at room temperature for 2 hours, and the reaction was stopped by TLC.

The obtained product was washed repeatedly with water and ethanol to give 81 g of pale yellow solid, yield 98%. Nuclear magnetics are shown in Figure 1.

Synthesis of Compound 4:

In 1000 L of absolute ethanol, the 81 G product obtained in the previous step, 30 G of benzamidine hydrochloride, 15 G of sodium hydroxide was added, stirred, and refluxed overnight. A large amount of solid was obtained, which was filtered, washed with water and washed with ethanol to give a white solid. 50 G, 60% yield was obtained. Nuclear magnetics are shown in Figure 2.

Synthesis of the second host material:

A 1 L four-necked flask was charged with 800 ML DMF, and 46 G of compound 4, 50 G of 3-oxazoline, copper powder, potassium carbonate, and nitrogen gas were stirred for 30 minutes, and the temperature was refluxed. No intermediates were present in the 24 hour TLC assay, the reaction was stopped and filtered. The obtained solution was poured into water, a solid was precipitated, filtered, and purified by toluene to give 50 g product. Nuclear magnetics are shown in Figure 4.

Example 3, third body synthesis

The δ-oxazoline was used as a reactant to obtain a compound to obtain a third host material.

Example 4

Using 9,9-dimethyl acridine as a reactant, a compound was obtained to obtain a fourth host material. Nuclear magnetic map 5.

Example 5: Synthesis of the fifth subject

Synthesis of Compound 1 : 3,5-Dibromobenzaldehyde was lithiated from 1,3,5-tribromobenzene to give a white solid.

Synthesis of Compound 6:

50.8 g of 3,5-dibromobenzaldehyde and 27.8 g of 2-acetylpyridine were added to 1000 mL of ethanol, and the mixture was stirred at room temperature, and 14.2 g of a 70 ml aqueous solution was added dropwise thereto, and the mixture was stirred at room temperature for 2 hours, and the reaction was stopped by TLC.

The obtained product was washed repeatedly with water and ethanol to obtain 61 g of pale yellow solid, yield 98%.

Synthesis of Compound 7:

In 1000 L of absolute ethanol, the 61 G product obtained in the previous step, 30 G of benzamidine hydrochloride, 15 G of sodium hydroxide was added, stirred, and refluxed overnight. A large amount of solid was obtained, which was filtered, washed with water and washed with ethanol to give a white solid. 50 G, 65% yield was obtained. Compound 7 was identified by analysis of FD-MS 467.15.

Synthesis of the fifth host material:

A 1 L four-necked flask was charged with 800 ML DMF, and 46 G of compound 7, 50 G of 1-oxazoline, copper powder, potassium carbonate was added, and the mixture was stirred under nitrogen for 30 minutes, and the temperature was refluxed. No intermediates were present in the 24 hour TLC assay, the reaction was stopped and filtered. The obtained solution was poured into water, a solid was precipitated, filtered, and purified by toluene to give a 40 g product. The fifth host compound was identified by analysis of 641.71 of FD-MS.

Example 6 Synthesis of the sixth body

Synthesis of Compound 8:

Compound 8 was synthesized according to the synthesis process of the second host except that the amount of the oxazoline substance was half, and the compound 8 was obtained as a pale yellow solid in a yield of 65%.

Sixth main body synthesis:

According to the synthesis process of the second main body, the amount of the carbazole was 1.3 times that of the compound 8, and the reaction was carried out for 24 hours, and the column was purified to obtain a white solid, which was determined to be the target product by FD-MS.

The ultraviolet absorption spectrum and the photoluminescence spectrum of the materials of the first to sixth host materials prepared by the above-described synthesis examples and the comparative examples represented by the following chemical formulas at a low temperature (for example, 77 K) according to the method of the present invention were measured, and the results thereof were measured. In the table below.

Comparative example

Table 1:

	UV(nm)	PL(nm)	Energy level (eV)	LUMO (eV)	HOMO(eV)	Triplet level (eV)
Comparative example	365	425	3.51	-2.62	-6.13	2.65
Example 1	358	443	3.47	-2.78	-6.25	2.95
Example 2	363	424	3.43	-2.85	-6.28	2.94
Example 3	360	434	3.50	-2.75	-6.25	2.95
Example 4	355	424	3.46	-2.20	-5.66	2.93
Example 5	355	429	3.53	-2.87	-6.30	2.92
Example 6	355	432	3.43	-2.77	-6.20	2.93

It can be seen from Table 1 that the main body to the main body six or three linear states are higher than 2.92 eV, which can meet the requirements of the main body of the blue phosphorescent material. Compared with the comparative example, the introduction of oxazoline increased the triplet state, and the ratio of HOMO and LUMO decreased, indicating that the electron absorption of oxazoline was obvious. The main body five introduces an electron-withdrawing substituent pyridine, HOMO, LUMO is also greatly reduced, and the triplet state is relatively small. In the fourth embodiment, the introduction group is an acridine structure, which is an electron-donating group, and the LUMO and HOMO are significantly increased, and the electron transport performance is lowered.

A production example of an organic light emitting diode using a blue phosphorescent compound formed of the above first to sixth host materials and a material of a comparative example as a blue host will be described below.

The ITO substrate was patterned to have a light-emitting area of 3 mm X 3 mm, and then washed. After the ITO substrate was placed in a vacuum chamber, the bottom pressure was set to 1×10 ^-6 Torr. Then, on the ITO for forming the anode, HATCN having a thickness of about 50 angstroms was formed for the hole injection layer, and NPD having a thickness of about 550 angstroms was formed for the hole transport layer to form a TAPC having a thickness of about 100 angstroms. In the hole injection layer, a second host material having a thickness of about 300 angstroms and a FCNIr having a doping concentration of about 15% were formed for the light-emitting layer. Then, TmPyPb having a thickness of 400 angstroms was formed for the electron transport layer, LiF having a thickness of about 5 angstroms was formed for the electron injection layer, and an Al layer cathode of 1,100 angstroms was formed. Then, a packaging process is performed using a UV curable encapsulant and a moisture absorbent to form a light emitting diode.

TmPyPb:

Comparative example

An organic light emitting diode was fabricated in the same manner as in Production Example 1, except that the comparative example main body was used as the light emitting body.

As shown in Table 2, it was confirmed that the organic light-emitting diodes manufactured according to Production Examples 1, 2, 3, 5, and 6 exhibited luminous efficiency, quantum efficiency, and use when displaying the same level of color coordinates as compared with the comparative examples. Improvement in life. In particular, the service life of the organic light emitting diode is greatly improved. Example 4 introduction of acridine increased the transport of holes, thus the starting voltage ratio Lower, the system has a stronger ability to transport holes, the positive and negative charge transfer is not balanced, the life and efficiency are affected, and the performance of the main body is less than that of the introduction of oxazoline. The system introduces oxazoline, the electron-deficient properties of oxazoline are manifested, electron transport and injection are improved, and efficiency and lifetime are also significantly improved.

As described above, the method of the present invention produces a blue phosphorescent compound having high triplet energy, and uses the blue phosphorescent compound as a main body of the light emitting layer of the organic light emitting diode, thereby promoting energy in the light emitting layer Transfer and improve the blue emission efficiency and lifetime of the organic light-emitting layer.

While the embodiments of the present invention have been described by reference to the various embodiments of the invention, it will be understood that those skilled in the art may have many other modifications and embodiments that fall within the scope of the principles of the disclosure. More specifically, various variations and modifications are possible in the component parts and/or arrangement of the subject combination arrangement in the scope of the disclosure, the drawings and the appended claims. Alternative uses will also be apparent to those skilled in the art, in addition to variations and modifications in the component parts and/or arrangement.

Claims (10)

1. An aromatic heterocyclic compound represented by the formula (I),

   

   Wherein R1 to R5 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a C1-C4 substituted or unsubstituted phenyl group or biphenyl,

   Ar3, Ar4 are each independently a C1-C4 substituted or unsubstituted oxazoline, carbazole or hydrogen; and at least one is an oxazoline, an oxazole or an oxazoline is linked through a 9-position nitrogen atom,

   Ar5 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl or heteroaryl group of C6-C40,

   A3 and a4 each independently represent a C1-C4 substituted or unsubstituted phenylene group, and j, k each independently represent 0 or 1, and the hetero atom in the heteroaryl group is N, O, S.
2. The aromatic heterocyclic compound according to claim 1, wherein R1 is hydrogen or benzene, biphenyl, R2 to R5 represent hydrogen, j, k represents 0, and Ar5 represents a substituted or unsubstituted phenyl or biphenyl group.
3. The aromatic heterocyclic compound according to claim 1, which is represented by the following formula (II):

   

   Wherein R6 to R8 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl or heteroaryl group of C6-C40 or a fused ring aryl group or a fused ring heteroaryl group,

   Ar6, Ar7 represents hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or not Substituted aryl, substituted or unsubstituted Benzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthothiophene, oxazoline, pyridine, phenanthroline substituted or unsubstituted heterocyclic aryl; oxazoline is passed through the 9-position nitrogen Atom to link,

   A6 and a7 each independently represent a substituted or unsubstituted phenylene group, and m, n each independently represent 0 or 1.
4. The aromatic heterocyclic compound according to claim 3, wherein R1 is hydrogen or benzene, R2 to R5, R6 and R8 represent hydrogen, j, km, n represents 0, Ar6, Ar7 represents hydrogen, and R7 is unsubstituted or - 4 carbon-substituted phenyl, biphenyl, naphthyl, anthracenyl, fluorenyl, aryl, heteroaryl.
5. The aromatic heterocyclic compound according to claim 4, wherein Ar3 is one of an oxazoline, an Ar4 oxazoline, a hydrogen atom, or a carbazole.
6. The aromatic heterocyclic compound according to claim 3, which is represented by the following general formula (III):

   

   Wherein R9 and R10 each independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, a C1-C4 substituted or unsubstituted phenyl group or biphenyl.
7. The aromatic heterocyclic compound according to claim 6, wherein R1 is hydrogen or benzene, R2 to R5, R6, R8 to R10 represent hydrogen, j, n represents 0, Ar3 is an oxazoline, Ar7 represents hydrogen, and R7 is unsubstituted. Or a phenyl group substituted with 1 to 4 carbon atoms, a biphenyl group, a naphthyl group, an anthracenyl group, a spirofluorenyl group, and a C6-C20 heterocyclic aryl group.
8. The aromatic heterocyclic compound according to claim 1, which has the following structure:

   

   

   

   

   

   

   

   
9. An organic light emitting diode device comprising: a first electrode; a second electrode opposite to the first electrode; a light emitting layer between the first electrode and the second electrode, wherein the light emitting layer comprises the claims 1-8 Any organic compound.
10. The OLED device of claim 9, wherein the material of the luminescent layer comprises a body and a dopant, the organic compound according to any one of claims 1-8 as a blue phosphorescent host material and an electron transporting material, The device is a display device and a lighting device.

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